Aileen Lee coined the term “Unicorn” in 2013 to designate startups valued at a “billion” dollars. For personal perspective and context, Intuit in 1993 was the 4th largest software IPO ever with an IPO price of $300M valuation. Netflix went public in 2002 at the same $300M IPO valuation.

Aileen’s original post (for history sake) is here: Welcome To The Unicorn Club

And her follow up here: Follow Up Post - 10 yrs later

Tl;dr: It’s now time to unpack “trillions.” This is another long post. I “write things down” so that when we fast forward 5-10 years, we have a place to remember “where we were” vs. what appears to be in the future state of “normal.”

Here’s the top level summary of this post:

For the last 20 years, the U.S. economy has been shaped by 3 major trillion-dollar capital injections into our economy in the forms of:

• 2008-2012 Defensive Capital: mortgage crisis - great recession; $3-$4 Trillion

• 2012-2020 Financial Engineering Capital: ZIRP near 0% interest rates; $2-$3 Trillion

• 2020-2021 Consumer Liquidity Capital: Covid: $4-$5 Trillion; March 2020 Cares Act (PPP Loans of +$2 Trillion; America Rescue Plan of $2 Trillion in March 2021)

• 2025-Today AI Infrastructure Capital: $2-$3 Trillion (so far!); Goldman predicts over $7 Trillion from 2026-2031 for the continued buildout of data centers, chip fabs, energy grids and nuclear, cloud hyper-scaler infrastructure; robotics

We are once again rewiring our economy with trillions of dollars. Like the past trillion dollar cycles, we need to recognize the significant impacts of such capital deployment cycles on:

• company valuations

• labor markets

• business models

• operating models

• competitive advantage itself

Bottom line: capital cycles like this require CEOs and CFOs to re-evaluate their strategies to ensure their products, GTM motions, and R&D models continue to be aligned with their customers and competitive offerings.

LEARNING FROM HISTORY

History is an important teacher. Over the last 20 years, the U.S. economy has gone through one of the greatest capital deployment experiments in modern history.

When I started my career, “billions” was the term that caused most to pay attention.

Today it’s “trillions.”

We had zero trillion companies in June 2018. I’m excluding the oil company anomalies of PetroChina and Saudi Arabia Aramco.

Apple became our very first trillion dollar company in August 2018, quickly followed by Amazon in September 2018.

Microsoft was #3 in 2019 followed by #4 Alphabet (Google) in January 2020.

We only had these 4 when Covid hit in early 2020, and it wasn’t until June 2021 when the “T-Club” then quickly added two more - #5 Meta (Facebook) and then #6 Tesla in October 2021.

It wasn’t until May of 2023 when we added #7 Nvidia.

Today, we have 14 companies in our T-Club with 12 of the 14 being technology companies and the other 2 being Berkshire Hathaway and Eli Lilly.

How did we get here? My take? Two main sources. The US government injected trillions into into our financial system in addition to Mid-East Oil money being injected into the US.

Let’s walk through the last three major “Trillion Dollar Capital Cycles.”

Cycle #1 (2008–2009): The Financial System Rescue: $3-$4 Trillion

“Too Big To Fail”

The first major modern trillion-dollar intervention arrived during the housing collapse and global financial crisis.

The U.S. financial system was on the brink:

• Lehman Brothers collapsed

• Bear Stearns disappeared

• AIG (largest insurance company) nearly imploded

• major banks froze lending

• housing prices cratered

• consumer confidence collapsed

The government response was unprecedented injecting in the range of $3-$4 trillion of new dollars into our economy.

From Google search:

Between 2008 and 2012, the U.S. government and Federal Reserve injected trillions of dollars into the economy to fight the financial crisis. This included $443.5 billion disbursed through the Treasury’s Troubled Asset Relief Program (TARP) and roughly $2.3 trillion from the Federal Reserve’s first two rounds of Quantitative Easing (QE1 and QE2), plus massive emergency lending facilities. [1, 2, 3, 4]

Major Capital Injections and Programs (2008–2012)

• TARP (2008–2010): Authorized at $700 billion and later reduced to $475 billion, final total disbursements reached $443.5 billion. It injected capital into banks ($250 billion), AIG ($70 billion), the auto industry ($82 billion), and foreclosure prevention ($46 billion). [1, 2]

• QE1 (Nov 2008 – Mar 2010): The Federal Reserve pumped roughly $1.75 trillion into the economy by purchasing mortgage-backed securities, agency debt, and long-term Treasuries. [1, 2]

• QE2 (Nov 2010 – Jun 2011): The Federal Reserve injected an additional $600 billion by buying long-term U.S. Treasury securities. [1, 2]

• QE3 (Announced Sept 2012): Began an open-ended purchase of $40 billion per month in mortgage-backed securities, scaling up further into 2013. [1, 2]

• Federal Reserve Emergency Lending: Beyond QE, specialized Fed liquidity and lending facilities peaked at over $1 trillion in emergency short-term credit extended to financial institutions. [1]

This cycle was fundamentally Defensive Capital with a clear goal of US Economy survival to prevent systemic collapse, save the banking system, and restore consumer confidence.

This era taught markets something critical: the Federal Reserve would intervene aggressively when systemic risk appeared. This realization permanently changed investor psychology with respect to debt and equity.

Risk pricing changed forever.

Cycle #2 (2012–2020): ZIRP - The Zero Interest Rate Policy Era; $2-$3 Trillion

“Cheap Money Changes Everything”

After the financial crisis, interest rates effectively went to zero for nearly a decade. This wasn’t just monetary policy; it became “the new normal” and we all became a bit numb to a new operating environment.

Money became almost free. “Cash is trash” became a mantra.

What Happened?

• venture capital exploded

• SaaS valuations soared

• growth was prioritized over profits

• private equity leveraged aggressively

• tech hiring accelerated

• asset prices inflated across nearly every category

This 8 year period normalized:

• cash burn

• perpetual fundraising

• revenue multiples detached from fundamentals

• aggressive expansion strategies

The Fed balance sheet expanded from under $1T pre-crisis to roughly $4.5T+ pre- COVID and then ballooned to nearly $9 Trillion (doubling in 2 years). Today, the Fed’s balance sheet is just under $7 Trillion.

Here’s the Fed’s balance sheet expansion from 2004 to today, i.e. the last 20+ years:

Here’s our US National Debt:

What I’m calling cycle #2 (2012-2020) is best defined as:

Financial Engineering Capital.

Our economic system wasn’t just being stabilized anymore. It was being amplified.

What It Created

An entire generation of founders and operators grew up believing:

• capital would always be available

• fundraising solved operational problems

• growth outranked efficiency

• interest rates would remain structurally low forever

Then COVID arrived.

Cycle #3 (2020–2022): The Pandemic Super Stimulus: $4-$5 Trillion

“The Fastest Trillion-Dollar Injection in History”

COVID triggered one of the largest and fastest economic interventions ever attempted. Governments worldwide effectively decided:

“We will freeze the economy… and replace the lost demand ourselves.”

Resulting in a historic stimulus of epic proportions.

U.S. Response Included:

• CARES Act

• PPP loans

• direct stimulus checks

• enhanced unemployment

• business relief programs

• additional Fed expansion

• emergency liquidity programs

Approximate U.S. Totals:

Depending on methodology:

• $5T–$7T+ direct and indirect support

And globally? Far higher.

This cycle can best be defined as:

Consumer Liquidity Capital.

Unlike 2008, where the stimulus went to save our banks and key enterprises “too big to fail companies,” this money went directly into households and businesses.

Consumers suddenly had:

• cash

• low rates

• surging asset markets

Then our supply chains broke, including container ships being “stuck on the water” and Taiwan chip fab fires.

The economy overheated and inflation exploded.

The Result

We created:

• the fastest hiring cycle in decades

• historic wage inflation

• supply chain chaos

• speculative asset bubbles

• crypto mania

• meme stock behavior

• AI funding acceleration

• and eventually, the fastest rate hiking cycle in modern history, finally coming off the near-zero interest rate policies

From Google search:

Key Financial Insights

• The Velocity of Borrowing: The pandemic response was unprecedented in its speed. The federal government borrowed more money in the single 12-month span of 2020 (+$4.3 trillion) than it did during the first three full years of the Great Recession combined (2008 to 2010 added $3.5 trillion). [1, 2, 3]

• Debt-to-GDP Structural Shift: The 2008 crisis marked the point where the national debt began expanding rapidly compared to the economy. However, the massive 2020 spending packages pushed the total national debt to surpass 100% of the entire U.S. Gross Domestic Product (GDP) for the first time since World War II. [1, 2, 3, 4]

• Long-Term Compound Effect: These consecutive crisis interventions created a permanent upward trajectory for federal borrowing. Fueled heavily by the structural deficits left behind by these packages and rising interest rates, the total national debt has grown to $39.7 trillion.

2025 - 2030: Our Next Trillion Dollar Economic Cycle: Estimate ~$7 Trillion

The AI Infrastructure Buildout; Our Modern-Day Industrial Revolution

That was a lot of “setup” and I likely buried the lede (yes, “lede” is really spelled that way — look it up!), but I felt like the history was important, and I’ve never actually written it down that way... so now I have.

This is the cycle most people are still trying to fully understand. Unlike prior cycles, this cycle isn’t about government stimulus and not driven by consumers or banks.

This cycle is best defined as:

AI Infrastructure Capital

Goldmans’s estimated $7 trillion that will be spent by 2031 now has context to our above government stimuli.

Real cash is coming from public and private companies and is being invested into:

• AI data centers

• GPU chips

• memory chips

• semiconductor fabs

• energy grids

• nuclear

• cooling systems

• networking infrastructure

• sovereign AI initiatives

• robotics

• and all kinds of ecosystem supporting systems and services

Listening to CNBC, it seems that nearly every week companies are announcing plans to increase capital expenditures by billions.

Those of you who can add fast... that’s nearly $1 trillion from just this list of 7 already committed as of today.

Here’s the point: cash is not trash in this cycle. This capital is creating actual, physical industrial manufacturing and labor demand.

Specifically, with huge investments and employment in:

• construction

• power generation

• real estate

• skilled labor

• engineering

• chip manufacturing

• energy and water infrastructure

• utilities

• and many more areas including regional revitalization that supports these investments

I’m personally very bullish. If I zoom out and compare this cycle to the last 3 cycles, I believe this will become our most economically transformative cycle yet. Rather than being an “injection of cash” to “save the economy,” we are finally investing massively in real assets.

JUST IN: SpaceX’s new Terafab image has hit my “feed” since hitting publish. Here it is for perspective to bring this all together.

• 100 Million Sq feet…with size comparisons in the image

• $16B initial build cost

• Up to $120B total buildout cost (next 3-5 years)

I feel it’s important to “document the assumptions” and put a marker in the ground of “this was what was said in 2026” when we look back on this post in a few years.

This last image is the real stunner and brings home the new investment era we are in and how far behind our future demand people like Elon and all those who invest in SpaceX and Nvidia and others think we are and what we truly need in terms of compute power.

Why This Matters for CFOs and CEOs

Let’s call the next era the AI Acceleration Capital Cycle - I repeat $7 Trillion is likely to be invested over the next 5 years on Ai infrastructure builds alone.

Trillion-dollar investments have become the new normal. They are reshaping our technology industry currently and will flow to reshaping nearly every other industry post 2030. The ripple effects and how our economy and society inflects as a result will be fascinating to watch.

When industries, companies, economies, and societies are reshaped, we must respond with new ways of thinking vs. our old ways of thinking and deciding.

The companies that succeeded during the 2012-2020 period following the housing crisis and the Great Recession made strategic bets based on the prevailing economic conditions and the era of zero-interest-rate policy (ZIRP) stimulus, while many others dismissed those conditions as unsustainable and argued they couldn't last.

During the pandemic, many naysayers argued that the world had been permanently changed and that global economies were headed for collapse. Yet within a year, in 2021, the global economy experienced one of the fastest V-shaped recoveries on record, thanks in large part to the trillions of dollars in fiscal and monetary stimulus injected into the worldwide economy. The ones who recognized this and played the new hands being dealt were the winners, while others who expected the world to go back to the “way it was” were the losers.

Today and tomorrow, we are the same “bet making” inflection point. The facts are clear. Another massive injection of “trillions of dollars” is now being invested into our economy. The buildouts will take longer (physical manufacturing and supply chain changes always take longer than fiscal stimulus) and will be healthier and more sustainable for our future.

This also means the world over the next 5 years will be different. We will have to take these facts into account for our respective long-range strategic planning, headcount planning, and our own capital investments into our companies.

We can no longer wonder whether we should start using AI Agents or whether our Engineer and Product Development departments should be using AI. We must challenge our peer leaders to “How Much AI Are You Using?” (maybe on a % basis of overall efforts), and then ask each what their % of AI will be in 6 months, 12 months, 18 months, and so on.

These assumptions must then tie back to our overall company planning and link to less headcount hired (This is wholly different than firing. I don’t believe that will happen. We just won’t hire as many new coding engineers).

We must also layer in spending on new AI-based software and agentic systems into our future plans.

A critical shift over the next few years will be adopting a new way of thinking: analyzing Return on Compute (ROC) instead of relying solely on our historical focus on Return on Investment (ROI). This is a mindset we all need to begin embracing immediately. (Next week's post will take a deeper dive into this concept.)

Specifically, this means we need a new tracking metric on “Token Economics” vs. historical “Unit Economics.”

More on all that in next week’s post.

Final Thoughts

I’m betting historians will look back at the 2000-2025 period and conclude:

The defining economic force of this 25-year era was not technology alone.

It was the repeated deployment of trillion-dollar capital cycles that continuously rewired the economy underneath us.

Technology + Capital will be our most powerful era ever.

The upcoming 2025-2050 era will be as unrecognizable as how today we wonder, “how the hell did we operate and live before PCs, Software, and Mobile Phones?” (Otherwise known as the 1950-1980s Era).

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You are the leader of a fast growing startup. You’ve just been acquired by a larger unicorn or public company 10x your size.

You wake up one morning shortly after and realize your personal operating model has shifted virtually overnight and the new operating model is literally suffocating you.

YOU: Faster > Higher Quality > More Agile

vs.

THEM: Slower > Risk-Averse > Lower Quality

Knowing how to survive and thrive being the “acquiree” is core wisdom that only comes from having “been there done that.” Few have written about it.

So, I’m writing this to try to help any current or future readers be prepared for what lies ahead and move beyond the classic questions of reactive “integration” and into the more proactive focus of continuing to compound your leadership value inside your new, much larger (and slower) organization.

This post is a practical playbook for how to take on a new change agent role inside the new company, and specifically, how to improve your new parent’s systems without triggering its antibodies. This post will also hopefully help you mentally survive your new reality.

Big companies aren’t usually slow and risk-averse by nature. It’s a learned response to threats thwarted because they’re dumb or lazy.

They’re slow because over time, they slowly optimized for:

• Reward over risk

• Quality over agility

• Auditability and compliance

• Public survivability

The very traits that made them successful as a smaller, younger startup have been replaced with predictable and rational risk reduction designed into most every process so that no single mistake can become a headline, regulator inquiry, or career-ending incident.

Risk aversion starts taking over for continuous and agile product and process quality.

But, if you (as the new found acquisition-child) show up with vocal high energy antics of,

“Your processes are broken and slow, and I’m here to fix it,”

you will either get politely ignored or actively neutralized.

Your job is not to “disrupt the parent.”

Your job is to upgrade the parent’s operating system in a way the parent can safely accept.

This acceptable upgradeability is the definition of being a change agent.

Your New Change Agent Posture: “Respect the Intent. Upgrade the Solution.”

This requires a hard personal mind shift by you, the younger, more agile, faster-thinking leader inside your larger, slower parent.

Some clear lessons learned:

• Don’t attack the process… simply hold a mirror up to it

• Align and protect on what the process is solving for

• Then (and only then) start modernizing it slowly to make the solution higher quality and faster, with the same acceptable risk.

Don’t ever forget: most legacy processes inside big companies were created by smart people, under real constraints, after a real scar.

Your success depends on honoring that history while re-rating the risk and rewriting the method.

Which brings me to a new framing that I just discussed with a client and is worthy of a broader post since more people need to hear this, and which I’m now turning into a new operating playbook for surviving your first 180 days of being acquired.

I’m looking at you Brex (Capital One), Metronome (Stripe), and Manus (Meta)!

If you are leader or know somebody in these orgs, you may want to hit the SHARE button now!

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Your 180 Day Leadership Change Agent PlayBook

I made up a few headlines along the way, “Islands of Safety” style, with my client so we would both remember and encapsulate the conversation:

Mirror Method

Re-Rating Risk/Quality

Make the Process Owner A Champion

Now, I’m writing this down as not only a summary for my client, but a post for all of you.

1) Mirror Method:

Hold up the mirror (without blame)

Describe the current workflow exactly as it is, in neutral language:

• The Steps

• The Handoffs

• The Cycle Times

• The Bottlenecks and Friction Points

• The Failure points

Step 1 Deliverable: A One-Page “Process Map + Friction Report” (facts only).

2) SOLVE-FOR:

Now align or remind what the current process is actually solving for.

Every process has (or had) a purpose. It was usually born out of:

• Compliance

• Risk Reduction (or avoidance altogether)

• Cost Control

• Quality Assurance

• Customer Protection

• Brand protection

• Fraud Prevention

• ______ [Insert Yours Here]

Your goal is to get the owner or the group of process owners to say out loud:

“This is what we are protecting.”

And

“This is what we are solving for.”

Note: It’s highly likely they’ve forgotten and haven’t looked through this lens in a few years. Especially when you hear the phrase, “This is how it’s always been done.”

Step 2 Deliverable: A Clear “Solve-For Statement”

3) Re-Rate the Risk & Quality Level

This is where change becomes rational instead of personal.

Ask:

• Has the risk environment changed since this was built?

  • (E.g., was this process built to avoid a $100K error when we were a $10M company while we are not a $100M company with processes that avoid $100K risks?)

• Are we guarding against a 2017 risk with a 2026 tax?

• What is the impact of our processes on our current customers (those who actually use these processes?)

• Have our potential failure modes changed (AI, cloud, privacy, speed, competitive cycle time)?

• Are we delivering an acceptable level of quality for today’s customer?

• Are we delivering an acceptable level of quality for ourselves?

Step 3 Deliverables:

1. “Risk Reset” — updated risk assumptions + updated acceptable level of risk.

2. “Quality Reset” — re-rate the desired level of quality the process outputs.

4) Make the current owner the champion of the upgrade

This is the Jedi Master leadership move. Make it their idea… not yours.

“These aren’t the droids you’re looking for!”

The process owner (often the creator of the process) doesn’t want to lose:

• control

• status

• narrative

• safety

So don’t take it away from them or make them defensive.

Instead, make them more of a champion and give them the upgrade as a win:

• “You built the right protection.”

• “The world has changed.”

• “Let’s modernize the process and improve our acceptable level of risk or our desired output quality level.”

• “You invented this and should lead this. I can help you bring quick-win pilots + proof.”

• “Together we can roll out the changes into the larger production system once we’ve proven it.”

Step 4 Deliverable: Owner-Led Change with You as the Change-Agent “Force”

Let’s Get Specific On The 180-Day Plan

Earn permission → deliver proof → create pull

If your goal is to improve the parent, you have to sequence your influence properly.

Day 1 is not “change day.”

Day 1 is trust day.

Below is the operating plan I recommend for the first six months.

Days 0–30: Earn Trust Without Losing Your Edge

Your goals

• Establish credibility without sounding like a threat

• Learn the parent’s “immune system”

• Build a map of who owns what (and why)

What to do

1. Run a Listening Tour (15–25 meetings)

   • Ask: “What’s working?” “What’s breaking?” “What scares you?” “What’s politically untouchable?”

   • Capture language. Big orgs run on vocabulary, not logic.

2. Create an “Owner Map”

   • Every important process has an owner, a shadow owner, and a veto holder.

   • Find all three.

3. Identify the “3 Process Tolls”
   These are the recurring pain points that slow execution:

   • approvals

   • procurement / vendor onboarding

   • security / compliance gates

     Pick the ones everyone complains about (but no one fixes).

4. Ship one “Respect Signal”

   • Publish a short note to key stakeholders:

     • what you heard

     • what you’re not going to break

     • what you want to learn next

     This calms their immune system.

What NOT to do

1. Don’t call anything “broken”

2. Don’t propose a rewrite

3. Don’t “announce efficiency” (it reads like layoffs)

Output of Days 0–30: A prioritized list of friction points + a trust foundation.

Days 31–60: Pick Your Wedge (and Choose a Battle You Can Win)

Your goals

• Select one change wedge with high ROI and low political cost

• Avoid “enterprise-wide” anything

• Design a pilot that preserves risk posture

The wedge criteria (use this checklist)

Choose a process that is:

• high frequency (happens weekly or daily)

• low existential risk (won’t trigger panic if tested)

• cross-functional pain (multiple teams want it improved)

• measurable (cycle time, error rate, cost, satisfaction)

Design the pilot using “Safe Change”

Your pilot must:

• keep the same solve-for intent (risk, compliance, quality)

• reduce cycle time or rework

• add visibility / auditability (big-company comfort)

• include rollback (a safety net)

Output of Days 31–60: One pilot charter, co-owned with the process owner.

Days 61–90: Deliver Proof (Not PowerPoints)

Your goals

• Build undeniable evidence

• Create internal advocates

• Make your solution feel inevitable

The “3 Proofs” to deliver

1. Proof of speed

   • cycle time reduction

2. Proof of safety

   • fewer errors / better controls / audit trail

3. Proof of adoption

   • users prefer it (internal NPS or satisfaction score)

4. The change-agent move: show the owner as the hero

In every update:

• Lead with the owner’s name

• Give them the microphone

• Make it clear you’re enabling their win

Output of Days 61–90: A measurable pilot win + a reference story.

Days 91–120: Scale Through Champions (Not Org Charts)

Your goals

• Expand adoption without triggering immune response

• Build a network of “process champions”

• Turn the pilot into a reusable template

What to do

1. Create a “Replicable Playbook”

   • one-page: problem, solve-for, pilot design, metrics, rollout steps

2. Start a Process Champions Group

   • 6–10 influential operators across functions

   • meet bi-weekly

   • agenda: remove blockers, share wins, pick next pilots

3. Adopt the “Pull, not Push” rule

   • Don’t force rollout.

   • Create enough success that other teams request it.

Output of Days 91–120: A second and third team adopting the model voluntarily.

Days 121–180: Institutionalize the Method (and Protect It)

Your goals

• Make the new way “the way we do things here”

• Create governance that doesn’t kill speed

• Ensure your work survives reorgs and leadership changes

What to institutionalize

1. A Shared “Solve-For Registry”

For major processes, document:

• What it’s solving for

• Risk rating assumptions

• Last review date

• Owner + backup owner

2. A Quarterly “Risk Reset” Cadence

Once per quarter:

• Review top processes

• Re-rate risk assumptions

• Decide whether controls are still appropriate

3. A Standard Pilot Mechanism

Every improvement proposal must include:

• Pilot scope

• Success metrics

• Failure metrics

• Rollback plan

4. A “Do Not Break” List

Some things stay slow because they must.

Codify what you will not optimize.

Output of Days 121–180: A durable system that keeps improving even when you’re not in the room.

The Change Agent’s Rules of Engagement

Here are the behaviors that separate “useful acquired leader” from “rejected transplant.”

1) Never attack the past — only update the assumptions

You are not smarter than the scars.

You are simply operating in a different era.

2) Translate startup speed into enterprise safety

Enterprise leaders don’t hate speed.

They hate unbounded risk.

Bring speed with guardrails.

3) Use language like an insider, not a critic

Words matter:

• “upgrade” beats “replace”

• “pilot” beats “rollout”

• “risk reset” beats “your process is outdated”

• “audit trail” beats “trust me”

4) Win through making others look good

Change in a large company is a status game.

If your success requires someone else to lose face, you will lose.

5) Pick fewer battles — and win them visibly

A single visible win buys you political capital.

Capital spent on ten small fights produces ten small enemies.

Try these:

1) “Solve-For Statements”

Most process fights aren’t about the process.

They’re about disagreement on what it’s solving for and at what risk or quality

Start by having everyone around the table write 2 sentences:

“This process exists to reduce risk and protect _______ from _______”

“This process makes sure we achieve this minimum range _____ of quality output.”

2) “Risk and Quality Resets”

If a process hasn’t been re-rated in years, it’s probably overpaying for old risk.

• A quarterly “Risk Reset” is the simplest re-framing I know.

• A quarterly “Quality Check” on the processes output.

• A quarterly “Customer Satisfaction” score of the process (quick two-question survey) makes sure the owners of the process aren’t living in the ivory tower of the systemic fortress they built.

3) “Make the Owner the Hero”

If your improvement requires someone to lose face, your improvement won’t ship.

Make your improvement idea… their idea. Lead with the vision of a future improved state they can help design and launch.

Your New Leadership Role Post-Acquisition

After acquisition, your title might stay the same but your leadership role will likely have to change.

You are no longer just building your product or scaling your team inside of a small startup.

You are now building confidence, improvement adoption, and operational trust inside a bigger system.

If you do it well, you become the acquired leader every parent wants:

• the one who speeds up execution

• improves quality

• reduces risk

• and makes the whole organization smarter

If you do it poorly, you become that problem child:

• “they don’t understand how things work here.”

• “they don’t listen and are reckless.”

• “those Silicon Valley people don’t understand big business.”

Your Call to Action

• Pick one process (and only one) this week that frustrates everyone post-acquisition. You might want to start with low-hanging fruit, such as an easy-to-pick winner with the operational staff. But definitely start with the highest priority: one large, winning process with the executive leadership team (the CEO, COO, CFO).

• Write the two “Solve-For” sentences.

• Run a 30-minute Risk Reset with the current owner.

• Design a quick-win pilot that improves speed and adds safety at near-zero risk to the larger system.

• Make the process owner the hero and encourage them to expand the pilot into a larger production run.

FINAL SUMMARY OF YOUR 180-Day PLAYBOOK FOR ACQUIRED LEADERS:

In 2026, M&A will be the default outcome for far more startups than IPO.

The standard question is good but not great: “How Well Will We Integrate?”

The better question is:

“Will we compound inside the parent OR get absorbed and slowed into irrelevance?”

Here’s the 180-day playbook I coach for acquired leaders:

✅ Days 0–30: Earn trust (listening tour, owner map, identify 3 process blockers)

✅ Days 31–60: Pick a wedge (high frequency, measurable, low political cost)

✅ Days 61–90: Deliver proof (speed + safety + adoption)

✅ Days 91–120: Scale through champions (pull, not push)

✅ Days 121–180: Institutionalize (solve-for database + quarterly risk resets + pilot-to-production runs)

Using the following methodologies:

1. Hold the mirror up (facts, not blame)

2. Align on what the process is solving for

3. Re-rate the risk and the quality (the world has changed; have our internal processes kept up?)

4. Make the process owner the champion of the upgrade

Big companies don’t hate speed. They just have forgotten how to run faster.

They hate risk and have forgotten how to operate higher on the risk curve and not operate so safely. Many times they will also choose lower risk over higher quality.

Your Change Agent Goal is to bring speed and quality with acceptable guardrails.

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To be clear, an executive offsite should not be a retreat and should not be a “get out of the office and talk big ideas” exercise… though I’ve seen and experienced these a lot.

Think of the offsite you are trying to plan and execute as a designed leadership system for:

• Aligning the executive team

• Making the hardest decisions of the year

• Establishing accountability and ownership that can cascade down to the entire company.

• Team relationship-building time

Let’s break it down.

IMPORTANT: You must not be the smartest person in the room. You must not design and execute the offsite just to tell everyone else in the room what to do and how to do it.

You are the Chief Architect and Chief Moderator (or you need to hire someone to play this role).

Your job is to:

• Frame the best strategic questions

• Moderate team tension

• Make sure every executive/team member contributes

• Convert discussion into decisions

• Leave no ambiguity about future direction

• Assign ownership and accountability

If you haven’t “defined the why” of the offsite and if you haven’t communicated clearly the purpose and expected outcomes of the time you are asking everyone to spend, then STOP. DO NOT PRESS GO. CANCEL the date and RESCHEDULE IT until you have this “why” or “purpose.”

Here are some examples:

1. Reality Alignment

   • Current situational analysis (both internally and externally)

   • Where we were, where we are, and where we need to go

2. Strategic Focus

   • Decide what we will do and what we will explicitly not do

   • Review/recommit or edit the company or the team’s current strategy

3. Decision Ownership

   • Document who owns which outcomes. “Outcomes” is the key word here... I didn’t say “initiatives” or “project ownership.” I chose the word “outcomes” for a reason: the expectation and why that result is so critical.

4. Execution Architecture

   • Translate strategy into priorities (P0, P1, P2) and how this team will measure success (i.e., metrics and KPIs)

   • Identify key dependencies and gaps for efficiently executing

   • Reaffirm the right people are on the right problems. (Ask: Is our org/team structure working well and are optimal to achieve our stated priorities and outcomes?)

5. Leadership Trust & Team Cohesion

   • Lean on the 5 Dysfunctions of a Team (Pat Lencioni) to ensure this key framework

     • Establish trust, vulnerability, and respect (this is why offsites have icebreakers)

     • Create a respectful environment for challenge

     • Make sure the challenge doesn’t turn personal or antagonistic

     • Drive team commitment to capabilities, dependencies, and milestone timing

The offsite must be designed to materially advance all five.

Now that we have a blueprint, it’s time for the pre-work.

Non-negotiable rule: no executive shows up “cold.”

Required Pre-Reads (Distributed 3-5 Days Prior)

• CEO framing memo (no more than 3 pages)

• Company scorecard (key metrics, board/investor commitments, team culture promises)

• Market & competitive snapshot

• Org health and talent risks

Great pre-wiring questions:

• What decisions must be made at this offsite?

• What risks or internal tensions need to surface?

• Create a T-chart for 90 days after the offsite: Success (left) vs. Failure (right)

End the memo with:

“Come prepared with a clear point of view. Be prepared to challenge assumptions (both your own and assumptions of others).”

The CEO Opening Script (Day 1 – Morning)

Purpose of the Opening
Set psychological safety and accountability.

Recommended Structure (20–30 minutes)

1. Why We Are Here

• Why this moment matters

• What is at stake if we get this wrong

• How this year or quarter differs from prior years or quarters

2. How We Will Work Together

Explicitly define behaviors:

• Challenging vs comfort

• Disagree in the room not outside it

• We must align and compromise on desired outcomes before we leave this offsite

• Phones/laptops down, active engagement up

3. What I Expect From Each of You

Be direct:

• Lead with data. If your POV is opinion based, say so.

• Speak from your function and the company

• Name risks early

• Own decisions once made

4. What We Will Produce (Clear Outputs)

• Clear strategic priorities (3–5 max)

• Defined success metrics

• Date based milestones

• Decision ownership

• Messaging for the company

DAY 1: Current Situation Analysis and Strategic Choices

Morning: State of the Business (Alignment First)

• CEO overview (high-level only)

• CFO / COO operational reality snapshot

• Market & competitive reality

• What surprised us this year?

CEO Role:
Moderate, synthesize, stop rabbit holes.

Midday: Strategic Tensions & Hard Truths

• What’s at risk?

• Where are we over-invested?

• Where are we under-invested?

• What would kill our plan?

CEO Tool:
Ask Powerful Questions, not statements.

Afternoon: Strategy Options & Tradeoffs

• Strategic themes for next 12–24 months

• Growth bets vs core execution

• Build / buy / partner decisions

• What we are saying “no” to

CEO Role:
Force prioritization.
Do not allow “and.”

Late Afternoon: Leadership Reflection Session

• What does this strategy demand from us as leaders?

• Where are we misaligned as a team?

• What behaviors must change?

This session should not be optional. The deeper you can go, the better. One of my favorite sessions was when we all took turns focusing on each exec, one at a time, and the rest of the room would go around and verbally tell the exec what they want “more of” (their strengths) and also what they want “less of” (their weaknesses).

Evening: Social + Bonding (Non-Strategic)

• Group dinner

• Informal setting

• No slides, no business debates

CEO Rule:
Be human. Be present. Model vulnerability.

DAY 2: Decisions, Execution, and Alignment

Morning: Decision Finalization

• Lock strategic priorities

• Confirm success metrics

• Assign single-point ownership

No “we.”
Only names.

Midday: Operating Model & Resources

• Org implications

• Capital allocation

• Talent gaps

• Execution risks

CEO Role:
Ensure strategy and structure align.

Afternoon: Cascading the Strategy

• What does this mean for:

  • Executives

  • Managers

  • Individual contributors

• What changes Monday morning?

• What stays the same?

Final Session: Alignment Check

Ask each executive:

• What decision are you now fully aligned behind?

• What will you personally communicate?

• What concerns remain and are now owned?

Strategy Dies Without Translation

CEO + Exec Team Communication Stack

1. Executive Alignment Memo (Within 48 Hours)

• Decisions made

• Priorities locked

• Ownership confirmed

2. All-Company Strategy Narrative (Within 7 Days)

Should include:

• Why now

• What’s changing

• What’s not changing

• How success will be measured

3. Manager Enablement Session

• Talking points

• FAQs

• What questions to expect

• What not to speculate on

4. Ongoing Reinforcement

• Quarterly updates

• Scorecard visibility

• Leadership consistency

• Over-presenting

• Avoiding conflict

• Letting dominant voices win

• Ending without clear decisions

• Failing to follow up

Remember: The quality of your strategy is capped by the quality of your moderation.

Your executive offsite is one of the highest leverage moments of the year.

Done right, it:

• Aligns leaders

• Sharpens focus

• Accelerates execution

• Builds trust that survives crisis

Done poorly, it:

• Creates false consensus

• Creates silos

• Erodes confidence

Design the room.
Design the questions.
Design the outcomes.

That’s the job.

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That was June 2024. We are now here. July 2026.

My first post began with one of my key philosophies, “Read It; Learn It; Do It; Teach It.”

This 100th post will dive into my coaching practice.

I began my actual coaching practice in late 2019, shortly before Covid. While I had been mentoring and advising for several years prior to that, this time I had a specific client who wanted dedicated 1:1 time. They wanted to pay me for my time. I leaned in.

For full transparency, I’ve never been formally trained as a “coach.” Never been certified with such places like CTI (Coaches Training Institute) or others. I had certainly been exposed to coaches throughout my career so at least I had a mental framework.

I began by interviewing about a half dozen CEO coaches who I respected highly to find out how they did it. After the 6th interview or so, I decided my practice had to be different. To be honest, I continue to have a very difficult relationship with the actual word “coach.” While I completely understood great coaching from a sports context (I belonged to several sports teams as I grew up), business coaches seemed to me to be more theoretical and academic vs practical and operational. Many coaches had never held the actual role of the person they were coaching.

As a CFO coach, I knew I wanted to be different. Having been the CFO “player,” I wanted to make the transition to the “coach” who had been on the field. The person who had been in my client’s shoes, made the mistakes they were about to make, and encouraged them for the successful initiatives they were embarking on.

To be that type of coach, I decided early on I had to know as much about my client as I possibly could as well as critical details of their executive peers, their CEO, and specific board members. To understand all of that, I needed more time. I needed a “Rhythm and a Rigor” with my clients. That means speaking to them at least once every 2 weeks, and ideally every week, so I can stay connected to them and the stories happening inside their companies and their departments.

A few years ago, I took this concept even further, and I began offering “Quick Hits” - quick texts and/or phone calls in the moment when my clients needed somebody like me vs. making them wait for their next “session” in a week or two. By then, their problem would likely have gone stale.

“Always On” coaching became a thing for my clients, as we used these “Quick Hits” to weave in the longer term leadership and career roadmapping that my weekly or bi-weekly deep-dive, 1-2 hour sessions focus on. “Solutioning the Now and Architecting the Future.” Hmmm…I like that phrasing. I may have to turn that into it’s own future post!

Consistently, my clients and colleagues would ask me how my practice scales. Fair question since I coach scaling, and I coach my clients and my colleagues to challenge any/all assumptions and especially challenge my ideas, frameworks, and playbooks. I was very transparent, and my answer for a few years was, “I’m not sure how this 1:1 experience with you ‘scales’,” and then gave many reasons why. The conversation would usually conclude with “You should write a book!” to which I’d reply I’ve had friends and colleagues write books and it’s an arduous 12-18 month “process” (besides, I see books as being more “old school” in today’s Instagram, Youtube, and AI world).

By 2024, I decided I could take a step toward scaling. I could definitely write and publish 1 article per week based on my frameworks and playbooks I coach. Maybe someday I could then stitch together several dozen of these publications into some sort of “book” or other. So, I researched the best publishing platform, began to structure my material by “themes,” and I launched my first post in June of 2024. That was 2 years ago.

So here we are on Substack, 100 posts later. Milestone #1 achieved. I now have a better idea of how I’m going to scale this practice and am developing several more “product” offerings, including a better way to access all my “best of” material and how to gather it in small groups to go really deep in a 1:Many vs 1:1 environment…stay tuned!

Now, 5+ years into my coaching practice, I continue to pattern match what I have learned about coaching and want to share with you what I believe are 6 “Coaching Zones” that show up in my coaching practice.

The 6 Coaching Zones

Sports metaphor: Fundamentals + drills.
This is skill-building. The person lacks the mental model, vocabulary, or reps.

My job as coach

• Diagnose the gap (knowledge vs. judgment vs. reps)

• Teach the concept simply

• Give a practice drill and a few ways to self-correct

Definition of done

• They can explain it back in their own words

• They can apply it to their current situation

• They leave with a “next rep” assignment

Powerful questions

• “What part is fuzzy: the concept, the steps, or the confidence?”

• “Where have you seen this done well before?”

• “If you had to teach this to someone else tomorrow, what would you say?”

Sports metaphor: Film room.
This is sharpening, not building from scratch.

My job as coach

• Separate signal from noise

• Improve the signal (pattern), logic, and structure

• Be direct and specific

Definition of done

• A tighter argument

• A cleaner narrative

• Clearer assumptions and implications

Powerful questions

• “What do you want the audience to believe after this?”

• “What’s the one sentence you’re trying to prove?”

• “Where will a skeptic push back first?”

Sports metaphor: Whiteboard + play design.
This is collaborative building. My client has a direction, but needs structure.

My job as coach

• Turn rough vision into clear strategy, structure, sequence and playbook execution

• Create constraints (scope, time, audience)

• Convert “ideas” into an executable plan

Definition of done

• A draft, outline, or plan

• Clear owners and next steps

• A timeline that matches reality

Powerful questions

• “What are we solving for - speed, quality, risk reduction, or alignment?”

• “What’s in / out of scope?”

• “What must be true for this to work?”

Sports metaphor: Scrimmage.
This is rehearsal under pressure. It’s about timing, confidence, and recovery.

My job as coach

• Create a realistic simulation

• Interrupt with targeted feedback

• Run it again until the reps stick

Definition of done

• A stronger opening

• Cleaner transitions

• Better answers to predictable questions

• Calmer cadence under heat

Powerful questions

• “Where do you feel least confident?”

• “What question are you hoping they don’t ask?”

• “What’s your one-slide / one-sentence anchor?”

Sports metaphor: Game-day leadership.
This is not about being right. It’s about leading the room to action.

My job as coach

• Map stakeholders and incentives

• Choose the right channel and sequence

• Script the message for the appropriate audience. Define, Align, Decide.

Definition of done

• A stakeholder map

• A message that matches the audience

• A playbook for execution sequencing (who/what first, who/what last)

• A strategy for objection handling

Powerful questions

• “What do they care about more than your proposal?”

• “What’s the cost of doing nothing for them?”

• “What’s the smallest ‘yes’ you need first?”

Sports metaphor: Conditioning + statistical analysis.
This is where coaching stops being talk and allows everyone to see reality and is the foundation for next session’s feedback and improvement.

Most “coaching” fails here because it’s too detailed. Too hard.

Think of Steph Curry and his 4 hours of shooting practice per day with the computer analyzing his techniques and his outcomes.

Or Scottie Scheffler or Bryson DeChambeau on the driving range with their actual coach analyzing all their swings and outcomes.

My job as coach

• Turn game time execution into the next game plan

• Push my client for going from good to great

• Challenge and fine tune/polish

Definition of done

• A scoreboard (what we’ll measure)

• A follow-up loop (“when do we review?”)

Powerful questions

• “What did you learn?

• “What can we improve?”

• “How do you want me to hold you accountable to this improvement plan?”

My Coaching Contract (feel free to steal this for your staff 1:1s)

At the start of any 1:1 session, ask:

1. Which zone are you in today?

2. What does “good” look like by the end of this conversation?

3. Do you want high-direct feedback, or more brainstorming?

4. What’s the next rep… and when do we review it?

This one minute prevents 30 minutes of misalignment.

Coaches Reminder

The goal of coaching isn’t to sound smart.

The goal is to help someone perform better. To hold up a mirror, create more confidence, and establish a clear path from thinking to doing. From good to great.

So next time a client or a direct report shows up with a “can you help me…” request…

Don’t start with answers.

Start with which zone are you in.

More on Picking a Zone: An Example

Most leaders “coach” the same way every time. They default to advice.

But your direct report (or client) isn’t always asking for advice. They’re asking for a specific kind of help. When you mismatch the coaching mode, you create friction:

• You teach when they wanted feedback.

• You critique when they wanted co-creation.

• You talk strategy when they needed reps.

More Powerful Questions To Help Coach

“Do you want Fundamentals?”

“Do you want Film Room Review?

“Do you want Game Planning and Whiteboard/Chalkboarding”?

“Do you want to Scrimmage”

“Or is it Game Time?” (P.S. what did the Scoreboard show after your last game?)

Coaching is a sport.

• Sometimes you’re a skills coach.

• Sometimes you’re the Offensive Coordinator drawing up plays.

• Sometimes you’re the assistant running drills.

• Sometimes you’re the head coach managing the clock.

Same coach. Different zone.

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And just like the Olympics, there are clear lessons to be learned that we can transfer from sports to business.

The World Cup games so far are giving us a perfect case study of talent vs team.

Nearly every game, the focus begins with the superstars - Lionel Messi (Argentina), Cristiano Ronaldo (Portugal), Christian Pulisic (USA), and Erling Haaland (Norway).

Each team has one - and no more than two - of these superstars, but we are witnessing very different results from the overall teams.

Yes, you need star players; those people who can make the play in the moment. But the superstars who need the team system bent around their preferred style usually end up losing.

The successful teams have successful superstars with teammates who know how to play to the superstar’s strengths. We’ve seen a lot of crosses into Haaland due to his physical stature and his remarkable heading ability. Messi’s teammates seem to be psychic at knowing where he will be before they pass it to him.

Just as in the World Cup matches, there’s also a noticeable rhythm and rigor in winning companies. For the World Cup, the teams that keep their spacing, make sharp and quick passes, and keep trusting their teammates to be in the proper position when they pass to that space, well, they score and win.

The opposite is also painfully true.

Case in point is Portugal’s Ronaldo. He is one of the best players ever. But, at 41 years of age and playing Spain, the best defensive team in the world, Ronaldo no longer has the quick bursts of speed to get past the defense. His current style (due mainly to his age) is to try to find the right space and hope his teammates can thread the defensive needle to allow him to touch the ball in a very tight space. Spain’s defensive style of play requires physical talent Ronaldo no longer has. Quite frankly, and this is a hard thing to say, he should not have been on the field for the Spain match if Portugal wanted to win. Or, better, Portugal should have put another faster attacker on the front line and changed their positional structure if they wanted to keep their superstar on the field.

We all saw this in the first two games that the USA played. We saw how their belief translated to their play on the field that carried them in their exciting wins. We then witnessed what happens when the same team clearly believed they were outmatched, almost from the original kickoff against Belgium. The power of belief, or in this case non-belief, was stunning to witness.

Then there was Cabo Verde.

Cabo Verde may be the best leadership story of the tournament. They did not have Argentina’s history, global brand, or superstar roster. But, they had structure, courage, and enough belief to push the defending champions into extra time before losing 3–2. They answered back twice in the final minutes when most everyone had counted them out and forced Argentina to literally survive a match.

Both England’s win over Mexico and the USA’s win over Bosnia-Herzgovenia are great leadership examples because their matches didn’t stay clean.

Both teams went up early. Both of their opponents fought back. Both teams received red cards and were forced to go down to 10 players.

Both games immediately became less about the original plan and all about adjustment, resilience, and collective discipline.

The larger lesson was that both teams had to change how they played once the conditions changed. They had to defend differently, communicate differently, manage the clock differently, and survive the uncomfortable parts of the match.

That is exactly what happens inside companies. The original plan almost never survives contact with the market, the customer, the competitor, the board, or the cash forecast. Great leaders do not fall in love with the plan; they stay committed to the scoreboard and adjust the shape of the team in real time.

Companies have penalty-kick moments. They come in the form of making a critical contract pricing call or wholesale pricing changes… or the layoff or reorg decisions, the acquisition offer, the board forecast reset, the “do we keep funding this product?” decision.

Companies find out very quickly whether your team has practiced its “penalty kicks.”

The Argentinas of the business world simply know they can win even when the pressure is extremely high. They focus and execute and simply believe they will win.

Argentina’s 0-2 comeback against Egypt was extremely impressive. They could have folded after their superstar Messi missed a penalty kick, but they stayed connected and scored two quick goals in the last 15 minutes of the match and then stunned Egypt with the final winning goal right before the end of regulation time.

Brazil is out. Portugal is out. USA is out. Canada is out. They all had their stars. Brazil and Portugal had an extremely strong historical reputations. USA and Canada had media narratives of home field advantage and “this could be the year.”

But, these reputations and narratives didn’t track their oppositions’ runners or defend their opponents’ transitions, and they certainly didn’t “finish” their chances in front of the goal or make the amazing goalie saves.

Same goes for companies.

Companies that have raised too much money, hired too many impressive resumes, or become too proud of their own narrative often eventually have executional staying power problems. Brand helps these companies recruit. History and media hype earns short term attention. Prior wins create confidence.

But reputation and narratives do not execute. The team does. The customer still decides. The market still decides. The scoreboard tells the final scores at the end of each round.

France (a perennial powerhouse) beat Paraguay 1-0. It was not a masterpiece. It was a grind, and many said the play on the pitch was ugly and disjointed. But France figured it out in the end and won a hard fought victory.

As a leader, this is a key lesson to remember: not every quarter is going to be elegant. Not every product launch is clean. The operating plan never unfolds with perfect assumptions. Sometimes the job is to simply move forward. Stabilize the extremely upset customer. Close the financing. Protect the cash. Ship the release. Make the decision. Great teams don’t focus on style points. They simply focus on wins and continuous improvement.

Final Business Lesson: The Scoreboard Defines Winning

A great company or team meeting is not the scoreboard. A great org chart/roster is not the scoreboard. The loudest voice in the room is not the scoreboard. The founder’s preferences, the CFO’s model, the COO’s processes, or the Sales Leader’s favorite Go-To-Market motion are not the scoreboard.

The scoreboard is the team’s shared goal whether it be revenue, margin, customer trust, product quality, or whatever metric that actually defines the match or the round you are trying to win.

How are we trying to win?

How much time do we have left?

What zone or team structure are we in?

Is everyone playing their position properly?

Do we need to sub anybody out?

Are we playing to our strengths?

Are we exploiting our opponent’s weaknesses?

Who Will Win?

We’ll all know in a few weeks, but I’m certain the teams that advance will be the ones that combine their talent, trust, belief, positioning, discipline, and execution under pressure.

Your company and your team are no different.

In the end, few people will remember the exact player who scored the goals.

But they will remember the team who won the match.

And even if you lose the match, like Cabo Verde, you can win the hearts of others who may have never heard of you by playing like a team and leaving it all on the field (“pitch”).

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I’ll focus this post on financial and operational leaders (CFOs and COOs) attempting to apply “Purpose”.

CFOs in particular are usually starved for time, buried in details, trapped in deadlines, and rewarded for today’s precision vs tomorrow’s purpose. At least that’s the conversation I have a lot with my clients.

It’s time to write about, and hopefully you can specifically apply, a few “purpose frameworks” and offer a few purpose playbooks required for CFO leadership.

But how do we operationalize “Purpose”?

My take? In the operational world of leadership, we need to design systems with purpose and through these same systems, lead with purpose.

Purpose tells you what matters and what doesn’t.

Purpose tells your team why their work matters.

Purpose (when designed properly) can tell people what to say yes to, what to say no to, what to escalate, what to ignore, and what values, behaviors, and operating standards are non-negotiable.

Let’s think about the opposite. Leading without purpose? When finance teams lead without purpose, we become reporting factories, budget police, and the machine that closes-the-books.

We end up as very capable people doing technically correct work while also feeling disconnected from the actual purpose of the business.

The best CFOs I’ve worked with, and many whom I have coached, eventually learn how to apply purpose at multiple levels and significantly elevate their leadership and their teams impact.

When you double click into these exceptional teams, the pattern that emerges is these teams are better at operationalizing the company’s and their departments purpose.

As a result of thinking about all this, I’ve come up with 5 Purpose Zones as a framework for operationalizing purpose.

The 5 Purpose Zones of CFO Leadership

Zone 1: Your Personal Purpose as a Leader

Before you define the purpose of the finance function, start with yourself.

Why do you lead? This is not your title, your work history, or your capability stack.

One of my colleagues a long time ago in a galaxy far away, got up in front of a few hundred people at our company all hands and asked one simple question to the entire employee base. It was unscripted. It was powerful.

“What Is Your Why?”

Specifically:

• Why are you here? At this company?

• What can you offer to your team? To your company?

• What do you want your team, CEO, and board to feel when you walk into the room?

• What leadership values do you exist to create?

For many CFOs, the answer is some version of this:

“I am here to create clarity, confidence, discipline, and better decisions.”

That’s a purpose with a leadership promise. That’s something your team can start to feel.

Your personal purpose becomes especially important under pressure.

Pressure reveals your true character and what you actually believe, what you will do, how you lead, and what people will remember.

They say, the true character of a person and a team is revealed only under pressure.

If your leadership purpose is not clear to you, then your behavior under pressure will likely default to emotion, ego, or fear.

Don’t go there.

Instead start here:

Write your own sentence. Try this template:

My leadership purpose is to __________ for __________ by __________.

Example:

My leadership purpose is to create clarity and confidence for the company by turning ambiguity into decisions, discipline, and action.

Now we’re getting somewhere.

Zone 2: The Purpose of the CFO Function

What is the finance function actually here to do?

Make sure you don’t answer this too narrowly.

I’ve heard narrow answers like:

• close the books

• build the budget

• report the numbers

• manage cash

• keep the company compliant

While all true, this purpose is way too narrow and not a world-class finance purpose.

My personal deeper purpose of finance?

Finance exists to help the company make higher quality + higher velocity decisions with limited resources to make the best risk-adjusted resource bets.

Now finance is no longer just the department that measures the business.

Finance becomes the function that helps design the business. Dare I say architect of the business model?

• Finance becomes the translator between strategy and execution.

• Finance drives to create the best insight to properly allocate scarce resources.

• Finance becomes the system that converts assumptions into decisions, decisions into investments, and investments into learning.

Now we are talking! Sounds more strategic. Sounds like there are a lot of focusing activities we could unpack underneath THAT foundation of purpose.

You’ve heard me say before that the best CFOs should think like the internal VC of the business.

This is exactly why and how purpose needs to show up.

• You are not merely approving spend.

• You are underwriting investment theses.

• You are not just reporting variance.

• You are helping the company understand whether the original purpose of the spend is being achieved.

• You are not just protecting cash.

• You are buying time, optionality, and strategic freedom.

Now we are really talking about operationalizing purpose!

Zone 3: The Purpose of Each Team Inside Finance

This is where most CFOs stop too early. They define purpose for themselves or maybe take the extra step at a department offsite for the finance team more broadly.

But have you driven your leadership team to translate purpose all the way down to the sub-team level? Down to the staff level?

As I’ve said before, everyone should be an owner of their area of expertise. Each should have a product they deliver to their customers. Today, I’m saying very clearly to deliver your finance product with a clear purpose.

Specific Examples:

FP&A purpose:

To help leaders make faster and better decisions.

Accounting purpose:

To create the timely, trusted source of truth.

Payroll purpose:

To protect one of the company’s most sacred promises to be paid on time and accurately.

Accounts Payable purpose:

To balance trust, control, vendor relations, and cash discipline.

Procurement purpose:

To make smart spending easier and bad spending harder.

Treasury purpose:

To preserve cash reserve flexibility and to extend strategic runway.

Finance Systems purpose:

To create clean data, faster workflows, and better operating leverage.

The finance team is no longer just processing.

We are now on a mission with a higher purpose.

As the CFO leader, your 1:1s now improve.

Your finance team’s onboarding for new hires now gets more focused.

6 months later, these same new hires can now connect with their performance reviews in much more tangible ways.

6 months after this, the quality of the products the finance team produces continues to increase.

One of the biggest mistakes in leadership is assuming people automatically understand the importance of their work.

My experience? Most of the times they don’t. As a leader, you must constantly connect the dots and remind them of the importance of their work.

Zone 4: Applying Purpose To Decisions

The decisions playbook.

A purpose-driven CFO uses purpose to improve decisions.

• Every major spend request.

• Every new hire.

• Every system implementation.

• Every budget increase.

• Every termination

• Every re-org.

• Every strategic bet.

All of it should be tested through purpose.

Powerful Questions?

• What is the purpose of this investment?

Not the description or the vendor pitch. Not the political argument or the pie in the sky opportunity.

The Purpose? = What Are We Trying To Make True?

This one question eliminates an amazing amount of bad thinking.

Because many teams ask for money with a specific activity in mind, not with the ultimate purpose in mind.

• “We need this hire.”

• “We need this tool.”

• “We need this vendor.”

• “We need this spend.”

Maybe. But Why?

For what purpose?

• To accelerate what?

• To de-risk what?

• To improve what?

• To protect what?

• To learn what?

• To unlock what?

If the purpose is weak, fuzzy, or disconnected from strategy, the investment should probably die.

Hard stop.

I’d encourage every CFO leader to add these 5 Purpose Questions into their decision process:

1. What are we really solving for?

2. How does this support our strategy?

3. What must be true for this to achieve its purpose?

4. What happens if we do nothing?

5. What signals or milestones will tell us the purpose is actually being achieved?

That last one matters a lot.

Because purpose statements without a success signal (dare I say metrics or milestones) becomes operational theater.

Purpose must be measurable enough to guide action.

It doesn’t need to be a perfect measurement. It only needs to be a directionally useful measurement.

Zone 5: Purpose in Communication, Expectations, and Culture

The final zone is where purpose can make a company-wide impact.

Because purpose is not what you wrote down with that fill in the blank exercise.

Purpose is what your team repeatedly hears, sees, and experiences.

Purpose only matters when it becomes part of the operating rhythm.

It must show up in:

• your hiring language

• your onboarding

• your team meetings

• your planning process

• your decision memos

• your 1:1s

• your performance reviews

• your praise

• your corrections

• your storytelling

This is also where my “Lead With Expectations” matters.

If your team’s purpose is to create trusted truth, then define what that means.

If your team’s purpose is to help leaders make better decisions sooner, then define what great looks like.

If your role is to create clarity and confidence, then your communication had better do exactly that.

Great CFO leadership requires both.

This is also where your communication style matters the most.

If you know the purpose of your message, you stop overloading people with details.

• You lead with the Headline.

• You start with Why this matters

• And What Tradeoffs are real

• The Risk that needs to be understood

• The Actions that must come next

Now we’ve connected Purpose to also sharpening your communications!

It makes your message cleaner because you know what the message is for.

And that matters a lot in finance, where details are both our superpower and our kryptonite.

The CFO Purpose Playbook

Here is the 7-step playbook I’d use if I were coaching a CFO team tomorrow:

1. Write your personal leadership purpose in one sentence.

What do you exist to create as a leader?

2. Write the purpose of the finance function in one sentence.

Not activities. Actual purpose.

3. Require every finance leader on your team to write a purpose statement for their sub-function.

FP&A, Accounting, Payroll, Procurement, Systems, Treasury, Tax, IR, whoever sits in your org.

4. Start your next planning cycle with purpose before numbers.

Before you get to

• What we spent last year or last quarter.

• Headcount templates.

• Metrics and benchmark tabs

Define and literally Write Down:

5. Add purpose language to every major investment decision.

Every ask should include:

• purpose

• strategic rationale

• critical assumptions

• signals of success (and failure); metrics; milestones

• owner

6. Use purpose to define expectations.

What does “great” look like if we actually live our purpose?

What’s unacceptable?

What behaviors support the purpose?

What behaviors destroy our defined purpose?

7. Repeat it 7 times, 7 different ways.

Because if you only said it once, you probably didn’t really say it.

Final Thoughts:

A CFO and finance team without purpose becomes reactive to the business.

A CFO with purpose architects the business.

Purpose is what turns finance from a control function into a leadership influence and impact.

Purpose turns your team from processors into partners.

Purpose uses reporting to influence.

Purpose shifts budgeting into strategic resource allocation.

Purpose is what gives all the details a point.

I can’t resist I have to include my favorite movie scene on “Have a Point!”:. Don’t let your finance team be Dell Griffith!

Purpose is the structural bridge between strategy and execution.

Purpose should be your operating system.

If this resonates, and you are committed and coachable and want to design and run your own Leadership Purpose Playbook all the way through to a clear leadership roadmap, I’d be glad to work with you or your team at your next offiste.

This is exactly the kind of hands-on coaching and operating work I do with founders and executive leaders. You can reach me at www.benchboard.com.

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I always answer carefully and humbly knowing that parenting overall is extremely humbling. Every child and every family is different. Every stage of development is different. Parenting is the one thing learned more in real time than could ever be taught, advised, or learned in a book.

But when people press me and say, “I get that… but c’mon Jim… give me your ‘Best Ofs’ for parenting.” I always come back to the same idea. P.S. I just had this conversation with a client last week.

MAKE THEM CURIOUS!

That’s it. Not smarter. Not more polished. Not more impressive. Not a 1-dimensional superstar in something. Not more obedient or compliant.

Just Make Them More Curious.

I fundamentally believe curiosity is the passion engine underneath almost everything else that matters in life. Well, that and confidence. But I’ve written previously here how confidence comes 2nd or 3rd. Belief and Curiosity are likely #1 and #2!

• Curious kids learn faster

• Curious kids ask better questions

• Curious kids become better problem solvers

• Curious kids are more willing to explore, test, fail, adjust, and try, try again

• Curious kids recover faster

• Fill in your own blank here

Today, we are learning that Curiosity matters even more now than it used to.

We are moving into a world where information is abundant. Knowledge is instantly accessible. Expertise, at least the historic and static kind, is a few questions away from your latest AI friend.

In that world, one of the greatest advantages won’t be having all the answers. AI will have all the answers.

But I believe AI will never be able to have the one superpower Humans have always had and has propelled our existence as a species.

Our human superpower is curiosity, exploration, invention. Building new things and technologies from historical knowledge and expertise.

So, if there was one thing I would highly recommend to teach your kids and I surely plan on teaching my own grandkids in roughly 10 years (hopefully not until then!) it will be:

• How to investigate

• How to ask better questions

• How to experiment and explore

• How to improve

• How to create new understanding from new tools

When I was a kid, one of my favorite books was “The Way Things Work” full of pictures and explanations but then encouraging me to build my own.

Curiosity is a habit. Help your kids build that habit of curiosity from the very earliest of ages. Here’s the thing. You don’t grow out of being curious. This is a stage-agnostic life habit.

Try not to fall into the parenting trap of defaulting to statements or being the “Answer Man”. “Hey Daddy, How Do I Do This?” Or, “Hey Daddy, How Does This Work?”

If you always give them the answer, you risk creating dependency. It teaches your child to wait for your answer instead of discovering the answers themselves. You may be subconsciously teaching them to look to authority before trying something on their own and failure (ahem… clears throat… Learning!)

So the advice I gave my client - they pressed me for it after all:

• Talk to your children a lot

• Ask them how things work

• Ask them to guess

• Ask them what they think is going on

• And what they would try next

• Make it a game. Play the game with them

• Let them be wrong!

Be careful to not interrupt that process too quickly with “No, not that way”. As hard as that is as a parent.

After all, we were once curious and then somewhere along the line (about the age of 12 or 13 I remember), the human brain switches to “I’ve figured everything in life out”.

As we progress into adulthood, this is more comfortable so we rely more on what we’ve already figured out and less and less on staying curious.

Which leads to defaulting to statements and answers instead of questions. Then we become a parent and our communication habits become a habit of speaking with our children.

So when asked “Hey Daddy?”, we show them. We solve for them. We correct them…thinking we are helping… and we are… just not as effectively. I believe in helping them solve things for themselves with various curiosity techniques.

Curiosity starts at the kitchen table or in the car, or driving your kids to school or to practice. They are a captive audience after all! On a walk or a hike. Watching a game together. Or better, playing a game together.

So when they ask you that next question, pause, and ask them a a question back. Try to teach your kid the world is something to engage with, not just receive.

Teach them confusion is not failure. It’s just part of the learning process.

Questions and curiosity are not weakness. Rather, they are the capabilities required for tomorrow’s world.

Bottom line: More than ever, we need to teach the next generation to be willing to ask questions, say “I don’t know”, and how to ask better questions.

If you can do this, I’m convinced this is a critical life skill and of course career skill and leadership skill.

Here’s the amazing thing that happens when you try this “Curiosity Thing”.

You get to see a world through your children’s eyes. You then start remembering your own childhood and when you first learned the same thing.

It’s fascinating to watch what they do. To watch how they think. To watch where they get stuck.

Now you can assist and ask more questions… but please resist “taking over” and “showing and telling”.

Your mission (should you choose to accept it) is to not raise kids who are dependent on you or the nearest expert in the room.

Your goal is to raise kids who believe they can enter a new problem, ask good questions, test a few ideas, and learn their way forward.

I fundamentally believe this will lead to the confidence of “I can figure anything out” and that confidence will compound for life as long as they stay curious.

OK. THAT WAS PARENTING. P.S. THIS WORKS WITH YOUR TEAMS TOO!

Helping your new hires be curious is critical. Encourage your emerging leaders to be curious! It works with anyone you are trying to develop instead of just manage.

The best leaders do not just hand out answers. They build people who know how to critically think and encourage them to bring curious solutions to new problems.

They create environments where questions are welcomed, exploration is safe, and learning is part of the operating system.

That is not only how you build stronger children, it’s how you build stronger teams. And today’s children are tomorrow’s teams.

Stay Curious My Friends

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Why eliminating 1:1s is one of the most dangerous ideas in startup culture and how to run them at the highest level

There is a new narrative spreading across startups:

“1:1s are a waste of time.”

Sometimes it’s framed more elegantly:

“In founder mode, you don’t need 1:1s.”

This is not founder mode. This is leadership malpractice.

The Real Problem Isn’t 1:1s

Bad 1:1s are everywhere.

• Unprepared

• Status-driven

• Manager-dominated

• No decisions

• No follow-through

The obvious conclusion? “Let’s just eliminate them.”

WRONG!

The issue isn’t the meeting.

What Breaks When You Remove 1:1s

When you stop consistent 1:1s, five things quietly degrade:

• Trust

• Context

• Feedback

• Risk

• Alignment

If you don’t want or need these 5 attributes in your company’s culture… then YES, you don’t need 1:1s.

You are shuddering at the thought of not having these core cultural elements? GOOD.

I’m a big fan of Raw Signal - Melissa Shapiro and Jonathan Nightingale’s newsletter. We are fellow Mozillians. They write way better than I do… so take it from them!

“I Really Don’t Have Anything This Week”

There is no shortcut to the long game. Raw Signal goes on to say:

Bill Campbell Also Weighs In:

He didn’t over-engineer it. He simplified it.

5 words on a whiteboard. For every 1:1. Simple.

• Both people come prepared

• Each writes down the 5 things that matter

• Overlap becomes the agenda

• Conversation goes deep

No templates. No theater. Just signal.

There is no one right way to run a 1:1.

But you must have them! Hard stop.

Real operators know:

1:1s must flex based on:

• the function

• the role

• the maturity of the employee

• the pressure of the business

So, as I try to do, I’m going to try to compile everything I’ve ever practiced, read, learned into an operating system.

The Cook’s PlayBooks 1:1 Operating System

Axis 1: Who Leads?

Report-Led (Default for Most Teams)

Used by:

• Product

• Engineering

• Marketing

• Ops

• People

Why it works:

• surfaces real issues

• empowers ownership

• builds leadership capacity

• enables upward feedback

Principle:
👉 The 1:1 exists for the report, not the manager

Manager-Led (When Performance Is Measured Precisely)

Used by:

• Finance

• Sales

• Customer Success

• Recruiting

• People Ops

Why it works:

• tight alignment to targets

• faster course correction

• clear performance expectations

Principle:
👉 The 1:1 is a performance acceleration tool

Axis 2: Structure Level

Unstructured (Exploration Mode)

Best for:

• senior talent

• creative functions

• early-stage ambiguity

Unstructured does NOT mean unprepared.

Agendas create safety.

Especially for:

• introverts

• new hires

• underrepresented team members

Structured (Execution Mode)

Best for:

• quota-driven teams

• scaling orgs

• high-accountability environments

But structure must include:

• space for concerns

• space for development

• space for feedback

Otherwise it becomes mechanical.

The Design Insight

Most companies or people teams try to force one model. Don’t do that.

Great teams and companies flex across all four quadrants:

Unstructured vs Structured

Report-Led vs Manager-Led

So, there’s your design starting point.

Your Questions Are Your Leverage Point

This is where most 1:1s fail. Not scheduling. Not structure.

Questions.

Specifically, bad questions:

• “How’s everything going?”

• “Any updates?”

• “Anything I can help with?”

These produce:

• Nothing-burger answers

• No data

• Zero Insight

• Time wasted

Powerful 1:1 Questions?

For Product Teams:

• What decision were you unsure about this week?

• What question did you get that you couldn’t answer?

• What do you need from me before next week?

For Marketing Teams:

• What’s stressing you out right now?

• What’s blocking progress?

• What feedback do you have for me?

For Engineering Teams:

• What’s on your agenda?

• What haven’t we talked about?

• What would make your job easier?

For Sales Teams:

• What are you doing well?

• What do you want to improve?

• What patterns are you seeing?

For Finance Teams

• What systems are working well?

• Have you explored AI Agents since we last talked?

• What have you learned?

• How is the “Product” you are delivering going?

• How does your “Customer” like your “Product”?

Never Cancel Your 1:1s

Back to Melissa and Jonathan (RawSignal) - “I really don’t have anything this week.”

DON’T THINK THIS. DON’T DO THIS.

Canceling 1:1s sends a signal:

• “You are not a priority.”

• Consistency builds trust.

• Inconsistency destroys it.

  ---

Two More Rules Worth Highlighting

1. Ask These Every Time

“Is there anything you need me to communicate to the rest of the organization?”

“Is there a risk in the company you are seeing that isn’t being addressed?

“Are there any negative cultural issues that you are hearing?”

2. Double Up on New Hires

Meet 2x per week for the first month.

Why?

• Alignment is built

• Culture is learned

• Expectations are set and bad habits are prevented

The Cook’s 1:1 Operating System (Final Form)

Every great 1:1 does five things:

1. Builds trust

2. Transfers context

3. Surfaces risk

4. Develops judgment

5. Aligns execution

If it’s not doing these five things…

👉 It’s broken.

The CFO / COO Insight

1:1s are not just leadership tools.

They are: Early warning systems

Before issues show up in:

• forecasts

• dashboards

• board decks

They show up in:

• Culture

• Execution

• Confidence

Cook’s PlayBooks Bottom Line

If you believe 1:1s are a waste of time:

You don’t have a time problem.

You have a leadership design problem.

The 1:1 is not a meeting.

It’s the single most important leadership alignment tool for companies.

Five words.

One real conversation.

Every week.

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Is there what I call “biased accountability” in your company?

The problem is when leaders stop evaluating performance or a key decision based on what the role (or decision) requires and start evaluating it based on how they feel about the person performing the role or decision.

This kind of personality bias cuts both ways.

Sometimes an under-performer gets protected because the CEO likes them, has history with them, or feels personally loyal to them.

Sometimes a strong performer gets questioned, sidelined, or pushed out because they are less politically smooth, less familiar, less flattering, or simply not part of the inner circle.

In either case, this usually doesn’t end well and could have been diagnosed much earlier.

One of the most important coaching tools I use with CEOs and leadership teams is the headline of this post.

Take the personalities out of the problem.

When emotions, relationships, history, and personal bias are clouding judgment, the solution is not more debate about the person.

The solution is to temporarily erase the person’s name and face off the board.

• No name

• No face

• No history

• No friendships

• No frustrations

• No narrative

Just the role.

• Just the work

• Just the scorecard

• Just the capabilities required

• Just the behaviors desired

Until a leadership team can define success and failure independent of the individual, they are usually not making a leadership decision.

They are making a loyalty decision, an emotional decision, or a political decision.

When Bias Enters the Equation

Bias shows up disguised as reasonableness.

Have you heard these phrases before?

• “But they’ve been with us since the beginning.”

• “She’s a good person.”

• “He works really hard.”

• “She’s loyal.”

• “He’s not that bad.”

• “The team likes him.”

• “She just needs more time.”

• “I’ve never really connected with her.”

• “He’s too intense.”

• “She’s not my style.”

• “I don’t know, something feels off.”

These are all personality filters and not performance standards.

As I began writing this post, I was focused on only one side of the performance equation (the non-performer) but as I put words on paper, I realize that personality filters affect both low performers and high performers.

Most of us have seen the weak performers protected who should otherwise be moved out of critical roles.

These same personality filters also punish strong performers who may not fit someone else’s (let’s say the CEO’s?) preferred style but are delivering exactly what the business needs.

This is where great leaders separate themselves from just good ones.

Good leaders manage around personalities.

Great leaders define the job so clearly that personalities become secondary.

The Hidden Forms of Bias Leaders Bring into Accountability Decisions

There are several common biases that contaminate talent decisions:

1. Relationship bias

A leader is personally close to the person, so they unconsciously lower the standard.

2. Loyalty bias

The person was there in the early days, survived hard times, or “took a chance on us,” so their current performance is evaluated through the lens of past contribution.

3. Style bias

A leader prefers a certain communication style, personality type, or presence, and mistakes familiarity for effectiveness.

4. Recency bias

A recent miss or recent win gets overweighted while the broader pattern gets ignored.

5. Conflict avoidance bias

The leader knows a hard call is needed but avoids it because the conversation will be uncomfortable.

6. Narrative bias

An old story about someone becomes fixed: “high potential,” “not strategic,” “solid but limited,” “not leadership material,” even when the evidence has changed.

7. Political bias

The decision gets influenced by alliances, optics, or who will be upset if the truth is confronted.

Every one of these biases creates drag on organizational performance.

And the higher the role, the more expensive this political bias becomes.

My Framework: Take the Personalities Out of the Problem

When I coach leaders through this, I ask them to move into a “definition world” vs a “political world”.

Where the role is defined first with absolute clarity without names, personal history, or recent past history.

Step 1: Define the role based on the success required

Using the powerful questions framework:

What does success look like over the next 12 months?

• What outcomes must this role produce?

• What goals must be hit?

• What metrics matter most?

• What milestones must be reached and by when?

• What decisions must this person be able to make?

• What level of leadership is required for the company’s next stage?

• What cross-functional influence must this role carry?

• What part of the business breaks if this seat is weak?

Step 2: Define failure just as clearly (note - right side/left side simple T-Charts work well here)

This is where many leadership teams are weak with any “problem”.

They can describe what they wish would happen, but they fail to clearly define what “unacceptable” looks like.

Defining Failure:

• What misses are no longer acceptable?

• What behaviors are unacceptable (damaging trust; slowing execution)?

• Are there areas in the organization overcompensating for this role?

• What repeated patterns are putting the business at risk?

• What is the cost of not fixing this role?

The first step of awareness is writing it down and staring at it.

Step 3: Separate outcomes from effort

Yes, effort matters. Character matters. Intent matters.

Ultimately, however, RESULTS MATTER!

A lot of leaders get trapped here because they admire the person’s work ethic, values, or commitment.

The question is not whether the person is trying hard. The question is whether the role (notice how I didn’t say “person”) is delivering the required results.

Bottom line: Is this role winning? Is this team winning? Are they progressing to a winning state or regressing to losing state?

Step 4: Define the required behaviors and capabilities

Every role should have a capabilities and behaviors required profile.

Both the WHAT needs to get done and the HOW it needs to get done. Bonus points if you can throw in WHEN.

Powerful Questions

• Can this person lead through ambiguity?

• Can they attract talent, build a team, not just do the work themselves?

• Can they operate cross-functionally - influence their peers?

• Can they make hard calls?

• Can they earn trust at the board level?

• Can they scale from startup hustle into system leadership?

• Can they build systems, not just rescue problems?

• Can they go from functional expertise to company wide leadership?

The issue is not always performance in the narrow sense. Much of what I describe above is “stage fit”. The company has outgrown the old version of the role and requires a new version of the role. “What got you here isn’t what it takes to get us there.”

Stage fit can only be handled well if leaders are honest enough to define it, actually see it, admit it, and have a good framework to communicate it.

Step 5: Build the scorecard

Create a scorecard with:

• Success outcomes

• Failure risks

• Goals

• Metrics

• Milestones

• Required behaviors

• Required capabilities

Now stare at the scorecard instead of the person.

That’s it.

When I’ve had clients do this exercise, our conversation becomes much more objective, role-based, non-biased, and a lot of the previously mentioned biases and emotional fog clears.

Step 6: Now (and only now) Ask The Ultimate Questions

Once the role is clear, then and only then, start asking the original questions:

• Do we have the right person for this?

• If this seat were empty today, would we hire this same person into it?

• Do we need to go get the best person in the market for this role?

• Is there somebody else in our organization who maps more closely to these attributes?

These questions force honesty without starting from personality.

They bring leaders back to accountability.

Is your CEO or executive leader asking the above questions without doing the scorecard work? Partner with them and make sure this work gets done and to avoid the biases if these questions start being answered without doing the work.

What CEOs and Leaders Often Get Wrong

Many CEOs think they are being kind when they protect an under-performer they know personally.

Their blindspot is these leaders are usually transferring the pain to everyone else.

The exec team feels it. The strongest performers resent it.

The company reorganizes itself around the weakness.

What happens next? Have you seen this?

• Standards erode

• Trust erodes

• Culture erodes

Eventually the CEO or the leader loses credibility because people conclude that accountability is not real. It is biased.

The reverse is also true.

When a CEO or leader develops a negative bias against a strong performer, the company also suffers.

Don’t Confuse Discomfort With Dysfunction

• Sometimes the person is too direct/blunt

• Sometimes they are not politically elegant

• Sometimes they are not easy and don’t just “get along”

• Sometimes they are simply saying the truth faster than others want to hear it

But they are delivering the outcomes, modeling the right standards, and carrying the real weight of the role, the leadership team has to be careful not to confuse discomfort with dysfunction.

Not Just A “People Issue”. An Operating Issue

When leaders fail to take personalities out of the problem, they make compromised talent decisions.

Compromised talent decisions quickly become compromised operational execution.

What happens next, we all recognize:

• Strategy slows down

• Decision quality declines

• Standards and equitable fairness goes out the window

• Politics rise

• Performance culture weakens

The best companies do not eliminate humanity from leadership.

They eliminate avoidable bias from role evaluation.

Back to the Role Scorecard:

The next time you are struggling with a person decision, try this exercise:

1. Write the role as if nobody is in it.

2. Describe the next 12 to 24 months of success.

3. List the outcomes, metrics, milestones, behaviors, and capabilities required.

Then ask yourself:

Would I confidently match this person to this scorecard?

Your job is not to protect your personal biases or narratives.

Your job is to solve for the role.

• Do you need to coach the person?

• Does it mean the role scope is just too much?

• Dividing and conquering everything the person is trying to do?

• It may mean replacing them.

But your leadership requirement is the same:

Great leadership is not about who you like. It is about what the role requires.

The key questions are:

WRAPPING IT ALL UP

The next time you are stuck on a difficult people decision, do this:

1. Erase the person’s face, name, vision in your head

2. Write up “the seat”

3. Define winning

4. Failure

5. Key metric and milestones required

6. Behaviors

7. Leadership capabilities

Now put the person back into this scorecard and map the answers to the person.

That is what I mean when I say, “Take the personalities out of the problem”.

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Gaining “Trust” and Credibility is a large part of an executive’s “Work”.

Trust can and will erode silently, gradually, then suddenly if you don’t work at it.

There’s no trust dashboard. No KPI. No red alert. Trust is the stuff of relationships.

Don’t pay attention to those relationships and one day… you’re out. Fired.

Those of you who know me or read a lot of my stuff, you know I love scorecards… so of course it’s time to create one. I’ve never seen it before so I just built it.

The CEO Trust Scorecard (1–10)

1–4: Low Trust (“You’re Replaceable”)

This is what I call fragile trust.

You’re in the role. But you’re not trusted in the role to make the calls or to help guide the team through a crisis.

What it looks like:

• You’re brought in late to key decisions

• Your data is questioned or re-checked

• The CEO goes around you to others

• You’re executing… not influencing

• You play it safe and avoid hard direct conversations and play the political soft line

What the CEO is thinking (but not saying):

• “I’m not sure I can rely on them.”

• “I need to double-check everything.”

• “They’re not scaling or creating influence in the org.”

Why you might be fired:

• Not because you failed…

• But because someone else feels like an upgrade/safer bet

At this level, you’re likely not seen as a strategic thinker (looking around corners) or someone willing to make the hard calls or take some good size bets (i.e. risk).

5–7: “Vanilla Trust” (You’re Doing the Job)

This is where I think most start up executives live. If I’m honest and now scoring myself with a scorecard I never built for myself, this was likely my own score for several years of my career.

I was competent. Reliable. Solid. But I was not indispensable.

What it looks like:

• I delivered what was asked

• I ran my finance and other functions well

• I was included in most but not all discussions

• I occasionally pushed back… but only when it felt safe

• I managed risk, but I rarely thought about shaping the company’s strategic direction

What my CEOs were likely thinking:

• “Jim is good.”

• “Jim does what he says he’ll do.”

• “I can count on Jim… for anything finance and ops related.”

Why I was fired:

• I wasn’t replaced for doing something wrong

• I was replaced for someone who could perceptively do more

I don’t believe my CEOs were ever worried about me.

But they were also not betting the company on me and many times in my early career they were double checking even my “strong recommendations” with others.

8–10: Required Trust (“I Can’t Run This Without You”)

This is where my role truly changed. I was no longer just an operator, maintainer, optimizer.

I was my CEO’s true thought partner, force multiplier, consigliere, and risk manager.

What it looked like:

• I was one of the CEO’s first calls and pulled into decisions early and many times in the CEO’s own “working sessions” before the CEO has a clearly formed view

• We pressure-tested each other

• We brought hard truths to each other before they become problems

• We connected strategy, structure, and execution in our decision making

• We simplified complexity into clear decisions

• We helped each other see around corners

Your CEO needs to be thinking:

• “I trust their judgment.”

• “They make me better.”

• “I don’t want to make big decisions without them.”

Why you might be fired:

• Almost never for performance

• Only if trust is broken (integrity, transparency, alignment)

At this level, you’re not just trusted. You are required.

TRUST REQUIREMENTS

Trust is not built on:

• Being liked

• Being agreeable

• Being busy

Trust is built on:

• Judgment under pressure

• Consistency over time

• Saying the hard thing early

• Being right… when it matters most

The CEO Question You Should Be Asking

If you want to calibrate your real score, ask yourself:

“What would my CEO say is the #1 reason I might get fired?”

If you don’t know the answer, it’s time to find out and build that courageous question/line of thinking into your CEO relationship over time.

How to Move Up the Curve

Moving from 5–7 to 8+ isn’t about working harder.

It’s about shifting how you think about your role and your influence:

• It’s about full ownership of your role

• It’s about approaching your executive relationship from a “Partner First” mentality

• It’s about taking on more and more of the business architect vision

And most importantly:

From protecting yourself → protecting the company

Final Thought:

Every CEO’s score isn’t objective. It’s more subjective and how they “feel”.

1. Close the Reliability Gap (No Misses)

• Hit every commitment - deadlines, numbers, follow-ups

• If something slips, communicate early (never late)

• “No Surprises”

2. Clean Up Your Data + Narrative

• Ensure your numbers are accurate, reconciled, and defensible

• Create key insights with clear, simple narratives

• Anticipate the first 3 questions the CEO, Board, Investors will ask

3. Answer the Question Asked

Many low-trust operators:

• Overcomplicate with details

• Go off-topic and down irrelevant rabbit holes

• Or avoid direct answers

Instead:

• Be confident and credible with your POV (Point of View)

• Lead with the answer

• Then support it and be willing to change it

4. Eliminate “Shadow Doubt”

If your CEO is going to someone else for validation…

Fix it by:

• Pre-aligning before meetings

• Sharing your POV and various options early and often

• Bring the benchmarked data the “other person” will likely have

5. Show You Understand the Business (Not Just Your Function)

• Constantly try to connect the business strategy to the organizational structure to the people executing the work

• Are we structured correctly to achieve our results?

• Are we performing at a high level?

• What could we invest in or de-invest in to make our strategy hum?

6. Say the Hard Thing Early

This is the fastest way to gain trust.

• Call out risks before they are obvious

• Challenge assumptions respectfully

• Don’t wait for “perfect data”

7. Reduce your CEO’s Decision Load

Your job is not to add information or more issues.

It’s to create clarity and remove issue.

• Simplify complex decisions into 2–3 clear choices

• Frame trade-offs explicitly

• Make decisions easier, not heavier

A Simple Weekly Practice

If you want to actively manage your trust score:

Keep a journal note (weekly?)

1. Where did I increase trust this week?

2. Where did I create doubt?

3. What hard thing did I say early?

4. What decision did I help simplify?

5. What is my CEO struggling with where I can help?

I promised an actual CEO-CFO Trust Scorecard. If you really want it, trust me! Just kidding. But c’mon, seriously become a paid subscriber. You’ve already read enough value here over the last dozen or so posts. I’m betting this will be the best paid content you see this month?

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Below are the 10 CEO Trust Attributes and Scoring System with actual action items.

Read more

Before you continue reading on - I know you came for this week's post, but if last week's piece on the private public company is still sitting with you, come continue the conversation live next Wednesday:

Think of the last bad outcome or result from your team or your company.

Did the conversation go like this?

• “We shouldn’t have done that.”

• “That was a bad call.”

• “Who approved this?”

This is one of the most expensive and worse leadership habits inside a scaling startup.

WHY? Because it teaches your team a dangerous lesson: judge the decision ONLY by the OUTCOME.

WHEN that happens, you don’t get better future decisions, you get worse, safer decisions. Political decisions. Slow decisions. Cover-your-ass decisions.

Today’s playbook is about decision science in our sport called business.

If you can remember one thing about creating your own decision making system it’s my headline to never forget to DIVIDE & CONQUER the decision.

Do this by installing two key decision separations. When you do, you’ll find, like I did, that your decisions as a team are instantly upgraded.

Playbook 1: Separate Decisions from their Outcomes

Playbook 2: Separate Decision Control vs Decision Concern

If you can do those two things consistently, you/your team/your company will operate better under pressure, faster during ambiguity, and you’ll implement a dramatically better decision learning system.

The Key Framework: Treat Decisions Like Bets

Playbook #1: Separate Decisions vs Outcomes

There’s a name for confusing a decision with its outcome: “Resulting”. I first heard this term from Annie Duke (world class poker player) in her brilliant book - Thinking in Bets.

RESULTING is the dangerous and expensive belief that:

• A good outcome proves a good decision

• A bad outcome proves a bad decision

In real life, outcomes are a messy mix of:

• Decision Quality

• Execution Quality

• Decision Timing

• Luck; Randomness

• External Events

• Competitor Actions

• Market Moods/Swings

• “Unknown Unknowns”

So if you want a company that learns, you need a new decision culture that constantly reminds your team(s):

The Decision / Outcome Matrix (Use this in your next leadership meeting)

1) Good decision → Good outcome - CODIFY IT; Earned Reward

Celebrate, but don’t over learn. Still make sure your decision didn’t have a luck component.

If not, then codify the decision recipe so the org learns and makes similar type decisions in the future.

2) Good decision → Bad outcome = UNLUCKY; Bad Luck

This was a high-probability and high-quality bet that didn’t pay off this time. You were unlucky and unfortunately hit the low probability outcome (assuming you took a “low probability risk”).

This is where great companies and great teams and great decision systems are made.

Protect the decision-maker. Study the assumptions. Improve the model and the next bet.

Key Focus for this Box - If you do nothing else, do this:

Make Box #2 (Bad Luck) psychologically safe and operationally useful.

Box #2 is where the best leaders play the long game.

3) Bad decision → Good outcome: LUCKY or DUMB LUCK

The most dangerous box. It creates false confidence and repeatable mistakes.

Be the courageous one and call out this truth. Use this post if you have to.

Otherwise, your team, your company, or even you will repeat the bad decision and next time you will not likely be lucky.

4) Bad decision → Bad outcome: DECISION PENALTY BOX; Deserved Failure

Fix the process and hold the person accountable. Since it’s Stanley Cup hockey season, do they get a 2 minute minor? or a 5 minute major? in your company’s version of the “penalty box”.

Annie Duke Quotes: I’m including these quotes from her book because a) my brain loves and remembers quotes and b) they are plain great quotes.

Annie Duke on probabilistic thinking:

A CFO/COO Operator’s Rule

Decisions are leading indicators. Outcomes are lagging indicators.

If you want better outcomes, improve your decision system:

• How are your decisions framed?

• Who owns them?

• Are Assumptions written down?

• Are Confidence and Risks scored?

• How will we course correct the next decision?

The “Time-Stamped Decision” Habit

Here’s how you stop the hindsight machine.

Before the decision, capture a simple time-stamped record:

• What we know (facts)

• What we believe (assumptions)

• Options considered (options)

• What would change our mind (metrics that would prove we are wrong)

• Success (metrics to increase your bet or double down)

• Kill Criteria (metrics to cut, pivot, or stop)

• Confidence score (0–10)

• Risk score (Probability × Severity - my Risk Equation)

• Review Dates (the actual dates when we’ll revisit this “Time Stamped Decision Record”)

The Aha here? You are reviewing a decision scorecard, not the emotional memory of the room.

Playbook #2: Separate Control from Concern

Now let’s layer in the second Divide & Conquer Playbook.

Being able to separate the things you can control vs the things you can’t helps keep you and your team’s sanity.

It’s a good time for the famous Serenity Prayer quote

Most exec teams carry a mostly invisible mental backpack full of everything they’re worried about.

The problem isn’t the concerns inside their heads

The problem is not having the Courage to change the things you can Control.

The CFO / COO Operator Rule:

Your time and attention are scarce resources. I’ve argued in past posts that TIME is your most valuable resource.

So treat your time and attention with the value it deserves:

• Control = where can you take direct action?

• Influence = where can you influence others to shape the outcome you want

• Concern (Risk) = where you can’t change it, but you should monitor it

If you don’t separate these, you get:

• Endless meetings

• Performance issues

• Reactive leadership

• Sloppy decisions made to relieve anxiety but don’t solve the core/root problems

• A culture of emotional volatility masquerading as urgency

The “3D” Control vs. Concern Playbook:

1. DO

2. DRIVE

3. DETECT

Use this simple “3D” language:

1) DO (Control)

Things you can directly change.

• Pricing

• Hiring

• Product Features

• Vendor selection

• Cash Runway Decisions

• Operational Systems and Process

Output: a decision + owner + due date

2) DRIVE (Influence)

Things you can’t do alone, but you can influence.

• Sales Execution

• Customer Retention Behaviors

• Manager Performance

• Cross-Functional Accountability

• Board or Investor Narratives

Output: a plan + coaching loop + metrics

3) DETECT (Concern; Risks)

Things you can’t control, but must monitor.

• Interest Rates

• Competitor Behavior

• Regulatory Shifts

• Platform Risk

• GeoPolitical Events

• Stock Market Downturns

Output: a dashboard + thresholds + pre-wired response decisions

If I sound like a broken record, this is why I’ve written about this so many times in the past. Maybe, just maybe, you’ll remember it this time! Just kidding. But seriously…

Don’t just model scenarios. Pre-wire the responses.

“Decide the future vs. Forecasting it.”

Why These Two Separations Belong Together

When you confuse decisions with outcomes, you create FEAR.

When you confuse control with concern, you create CHAOS.

Fear + chaos produces the same result every time:

• Slower Decisions

• Worse Accountability

• Less Innovation and Experimentation

• Less Learning

• More Politics

“6 Powerful Questions” to Run With Your Team

Use these the next time a decision goes sideways:

1. Was this a good decision with a bad outcome OR a bad decision with a lucky outcome?

2. What were our assumptions when we made the decision?

3. Which assumptions were wrong? Which assumptions were reasonable?

4. What did we fail to measure soon enough?

5. What is in our control, what can we influence, and what is simply uncontrollable risk?

6. Would we make a similar improved decision today with upgraded assumptions and learning and higher probabilities of success?

These questions are how you build a world class decision system.

A New CFO/COO Decision Cultural Standard?

If you want one sentence to operationalize all of this, it’s this:

We don’t incentive or punish people for outcomes alone.

And

We expect our leaders to have ownership and be accountable to these 4 factors:

• Decision Quality

• Execution Quality

• Learning Speed

• Transparency of Assumptions

Bonus points: Rip up your current performance review system and build your next performance management cycle around these ownership and accountability concepts.

A Simple Challenge This Week

Run a 30-minute Decision Review on one recent “bad decision” (ahem… clears throat… produced a disappointing outcome).

2 Rules For Your 30-minute Decision Review

1. We can only evaluate the decision at the time it was made… not today in hindsight.

2. We must scorecard the decision assumptions, probabilities, and risks.

3. We must then be clear if we should edit/improve the decision and make it or not make it again.

If you post-mortem decisions like this going forward, you will:

• Eliminate Blame and Finger Pointing

• Create More Truth

• Course Correct Faster

• Eliminate Uncertainty With the Next Decision

• Create Stronger Team Trust

If you read this far - here’s your reward. You likely haven’t seen this. So I found it for you and stored it here. For those interested in brain science + biology - this is a very good talk. I highly encourage you to invest the 1 hr.

Easter Egg… minute 24… she even talks about the 2015 Seahawks vs Patriots SuperBowl… and Pete Carroll’s 1 yd line call where after the outcome (interception). All pundits declared this the worst play call in Super Bowl history.

Annie explicitly walks through this classic example of “Resulting” where the the stats showed a 1% probability of being intercepted. This play was on 2nd down with only 1 timeout left, the Seahawks were down by 4 pts (so they couldn’t kick a FG) and were on the 1 yd line. This 1% bad outcome, 2nd down pass play, was a 99% 3 step decision of saving time if the ball was incomplete and still allowing 2 running plays on 3rd and 4th down as needed.

Minute 1:02 (1 hr 2 minutes) - Annie’s insights on Impostor Syndrome and Trusted Groups is also incredibly valuable.

Contact me if you want to go deep on this topic and workshop with me over a few months in designing and executing your company’s Decision System!

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For my entire career and the entire history of Venture Capital, the IPO was the defining financial milestone for private companies.

It was the moment. It was the “graduation event” for private companies. We received “Tombstone Trophies”. We rang the bell. We started doing interviews on CNBC.

Over the last 10 years (from roughly 2015 to today), a massive amount of new money has entered the private company ecosystem (VCs and PEs) which has “slowly then suddenly” fundamentally changed the private company “market” of startups.

In the late 90s, the average time a celebrated IPO company was private before it filed to go public was 4 years.

By the late 2000s, private companies were “staying private longer” and the average was 8 years.

By 2015, the average public company was private for 12 years.

Today, I don’t even track the metric anymore as there simply has been a dearth of actual IPOs over the last 10 years.

But if I had to estimate it, we are approaching 15 years of being private before “going public”.

In terms of money raised at IPO and the market capitalization of companies IPO’ing over the same period? Here’s the data:

Many of today’s greatest companies already went public.

They just “became public” in the private market.

SpaceX.
Stripe.
OpenAI.
Anthropic.
Databricks.
And several others still marching toward the now magical trillion-dollar potential.

On CNBC and other media outlets, these companies and others are talked about as if they are already public.

These companies have already raised capital at scales larger than any IPO in history.

Not millions or billions of funds raised… but now 10s of billions.

Recently, we are now hearing $100s of billions in financing activities for these “private” companies.

Historically, the IPO was where institutional capital filled the scaling requirements.

Today, institutional capital has gone private.

The Private Market Became the New Public Market

Look closely at the cap tables of these late-stage private companies.

They don’t resemble “venture-backed startups.”

They resemble public companies.

Analyzing these cap tables you’ll find:

• Sovereign wealth funds

• Pension funds

• Mutual funds

• Hedge funds

• Family offices

• Cross-over investors

• Large institutional asset managers

• Massive secondary markets

• Structured liquidity programs

• And increasingly… retail participation

A vast majority of the retail participation is wrapped neatly in modern cap table packaging called SPVs (Special Purpose Vehicles).

AngelList helped normalize this structure years ago, but now the entire ecosystem has evolved around democratized private-company access.

Retail investors are already participating without the IPO.

A Distinction Without a Difference?

Historically, the IPO served several purposes:

1. An IPO Was The Source For Large Amounts of Capital

Already happening privately.

2. IPOs Created Liquidity

Secondary markets now accomplish much of this. True real-time liquidity, however, can only be found in public markets.

3. IPOs Institutionalized Ownership

This has largely already been accomplished a year before the actual IPO today.

4. IPOs Expanded Investor Access

Increasingly happening through SPVs and private access platforms.

5. IPOs Established Market Price Discovery

Private rounds now happen frequently enough to continuously reprice elite companies.

The old IPO process is no longer the beginning of institutional ownership.

Of these Top 5 IPO reasons today, only real liquidity - ability to buy and sell real-time is the reason to IPO.

Healthier? More Stable?

It can be argued that this private market evolution may actually be healthier for companies.

Giant late-stage private rounds eliminated one of the most dysfunctional aspects of historical IPOs:

The real price-discovery and volatility of first-day pricing pops and lock-up period declines.

For years, Wall Street celebrated IPO “success” when a stock exploded 40%, 60%, or 100% on day one.

But let’s call those IPO pops what they really were: Massive underpricing in the private markets.

Today’s IPOs are more likely to see their day 1 or week 1 prices decline significantly from their private values. The IPO “pop” has been mostly unseen in recent years.

Today’s mega-private rounds operate differently.

The capital is raised:

• Behind closed doors

• With (theoretically) better price discovery

• Across multiple rounds

• With (theoretically) sophisticated investors

• With structured governance

• And with far less speculative day-one frenzy (though speculative VC/PE Frenzy!)

Combined with controlled secondary liquidity, companies can scale with dramatically less volatility.

Cash Liquidity and funding stability creates better long-term execution environments.

The Rise of the “Private Public Company”

We are now witnessing the emergence of an entirely new category:

The Private-Public Company

These companies have:

• Hundreds of shareholders

• Institutional governance

• Massive valuations

• Global brands

• Mature financial systems

• Sophisticated reporting

• Deep liquidity ecosystems

• Structured employee liquidity

• And broad investor participation

Yet they remain technically “private.”

Why?

Staying private is no longer a disadvantage. It’s actually a huge ADVANTAGE!

They avoid:

• Quarterly earnings circus dynamics

• Activist pressure

• Quarterly short-term-ism

• Daily retail volatility

• Excessive public disclosure requirements

• And public market narrative swings

Meanwhile, they still have access to enormous pools of capital that only existed publicly historically.

The Old IPO Was a 1 Day Event; The New IPO Is Multi-Qtr/Year Process

Today, “The IPO” is unfolding continuously over years through progressive private capitalization.

The actual public listing may soon become little more than:

• A liquidity expansion event

• An index inclusion mechanism

• A regulatory and governance transition

• A simple PR and branding milestone

Economically?

The new and expanded private markets have already treated these companies as public long ago.

The real question is no longer: “When will these companies IPO?”

The real question is: “What does ‘public’ even mean anymore?”

Private Company Facts:

• Massive institutions already own the shares

• Retail investors already participate indirectly

• Continuous price discovery exists

• Secondary liquidity exists

• And tens of billions have already been raised…

A.K.A = “The IPO already happened”

The Data Tells the Story

For most of modern venture capital history, companies simply did not stay private long enough — or become large enough — to resemble today’s mega-unicorns.

That’s what makes today’s private company valuations so historically different and why it’s clear today’s largest private companies are “Already Public.”

The Historical IPO Model (1995–2025)

AHA Insight #1: Multiple private companies are now worth more than nearly every historical IPO ever created.

The historic private company financing ladder looked like this:

Seed → VC Rounds → IPO → Scale

The new model increasingly looks like:

Seed → VC Rounds → Growth Equity → Sovereign Funds → Crossover Funds → Secondary Markets → Mega Private Rounds → Why IPO?

AHA Insight #2: The private market has clearly now swallowed stages of company development that historically belonged to the public market.

For complete historical context and perspective, in 1999:

• $1B IPO’s Valuations were almost unheard of.

• $5B IPO’s Valuations was extraordinary.

• $10B+ IPOs, especially technology companies, barely existed.

In the 1990s, a $1B IPO Valuation for a Tech Company was extremely rare.

I believe only 3 companies achieved it [Netscape 1995 ($2.9 Billion); Yahoo ($1.0B 1996; Ebay 1998 ($1.9B)].

Priceline kicked off the Dot Com Bubble/Bust in March 1999 when they hit a never heard of before $10 Billion valuation after the 1st day of IPO Trading.

VA Linux was the poster child of Dot Com Boom/Bust in December 1999 with their $9B of Market Cap on their IPO, achieving the largest 1st day percent gain ever (700% 1st day Pop); IPO Price = $30 per share; Opening trade = $300 per share; Intra-day high $400 per share; 1st day close = $240 per share.

Today’s Private Company Perspective (2026):

Daily and weekly, we are hearing these kinds of valuations of still private companies:

• OpenAI $800 Billion

• Anthropic $900B - $1.5 Trillion

• SpaceX $1.5+ Trillion

• Stripe $200 Billion

• DataBricks $125 Billion

• XAI (formerly Twitter) $60-80 Billion

Private Companies? No, these are “Virtual Public Companies.”

My own personal stories and tracking I’ve done that nearly everyone doesn’t know or has long forgotten.

These stats will blow your mind. I encourage you to take your time in this section.

I recently spoke to a Stanford GSB (MBA) class and shared the stats below. Several asked “Really?” I had to say “Yes, REALLY!”

Intuit: March 1993 IPO

• 1st day IPO Price $20 per share

• $300 Million Market Cap at IPO Pricing (today, companies can’t go public unless they are worth more than $1B+ in the public markets)

• Total Shares Sold to Public = 1.75M shares (Jim, are you sure that’s not a typo? Nope - take a close look at my “Tombstone” pic at the very top of this post)

• Cash Raised at IPO or roughly $35 million after all fees/greenshoes. (IPO Price $20 per share x 1.7M shares)

• $400 Million Market Cap after IPO 1st Day Close ($33 per share; +33%) - there are hundreds of private companies valued at this level today

• “4th largest Software IPO Ever” - Headlines in these things called “Newspapers” in 1993 - (no internet, no browsers, no smartphones) - I still have the framed San Jose Mercury News article

• Today’s Intuit Market Cap 2026 = $115 Billion

• 400x Market Cap Increase since IPO Pricing

Amazon: May 1997 IPO

• 1st Day IPO Price $18 per share

• $425 Million Market Cap at IPO Pricing

• Total Shares Sold to Public = 3 million shares

• Cash Raised at IPO of roughly $50 million

• $550 Million Market Cap after IPO 1st Day Close ($23 per share; + 30%)

• Today’s Market Cap 2026 = $2.9 Trillion (with a “T”)

• 6,825x Market Cap Increase since IPO Pricing

Netflix: May 2022 IPO

• 1st Day IPO Price = $15 Per share

• $300 Million Market Cap at IPO Pricing

• Total Shares Sold to Public = 5.5 million shares

• Cash Raised at IPO of roughly $75 million

• ~$350 Million Market Cap after IPO 1st Day Close ($17 per share; +15%)

• Today’s Market Cap 2026 = $375 Billion

• +1000x Market Cap Increase vs IPO Pricing

Google: August 2004 IPO

• 1st Day IPO Price: $85 per share (Dutch Auction style - labeled a “failed IPO” at the time) - initial S-1 Pricing of $150 per share

• $25 Billion Market Cap at IPO Pricing

• Total Shares Sold to Public was about 20 million shares

• Cash Raised at IPO was roughly $1.7 Billion

• $30 Billion Market Cap after IPO 1st Day Close ($100 a share; +15%)

• Today’s Market Cap = $4.8 Trillion

• 200x Market Cap Increase since IPO Pricing

Facebook (Meta): May 2012 IPO

• 1st Day IPO Price = $38 per share

• $100 Billion Market Cap at IPO (absolutely unheard of at the time - crazy several called it)

• Zero 1st Day Pop. Stock closed where it was Priced after going up 20% intra-day and then falling by the close

• 420 million shares sold to public at IPO

• $16 Billion of IPO Proceeds (again, crazy and unheard of - see the others above for just how “crazy?”)

• Far and away the largest Tech IPO of the time

• Today’s Market Cap = $1.6 Trillion

• 16x Market Cap Increase since IPO Pricing

My take? Facebook was the “come to Jesus” moment for private markets and started the mental narrative of “If FB is worth this much, THEN my portfolio company is worth $Y…” and so the VCs and founders started pricing their private rounds this way.

Our financial markets have clearly evolved but our IPO Language or perspective hasn’t caught up yet.

The next generation of iconic companies may never experience the traditional IPO cycle the way prior generations did.

Because they are “already public” - they just don’t have a ticker symbol whose trades post real-time on the Nasdaq or NYSE.

CFO Guidance for the “Private Public Company”

Your first shift is psychological.

Many executive teams still describe themselves internally as:

• “A startup”

• “Early stage”

• Or “private”

But if your cap table includes:

• Sovereign wealth funds

• Crossover investors

• Mutual funds

• Pension funds

• Secondaries

• Tender programs

• And hundreds or even thousands of employee shareholders…

…you are already functioning inside the public capital markets ecosystem.

The CFO must become the architect of that transition long before the ticker symbol arrives.

1. Build Public Company Financial Discipline Early

The best private mega-companies now operate with public-company rigor years before IPO.

That means:

• Faster monthly closes

• Better forecasting accuracy

• Clean audits readiness

• Proper internal control and security/privacy controls

• Public company investor-grade metrics

• Operational rigor

The finance organization can no longer function as a reactive reporting team.

Once your valuation crosses $50B–$100B, the market assumes institutional maturity whether or not your systems are ready.

2. Design a Long-Term Liquidity Strategy

Historically, the IPO solved liquidity. Today, liquidity is continuous.

Employees, early investors, and executives increasingly expect:

• Structured liquidity windows including secondary programs and tender offers

• RSU type compensation opportunities.

This highlights the CFO responsibility of shareholder and stakeholder relations and doing so without destabilizing ownership structure or culture.

3. Build an Investor Relations Function Before You Need One

Many mega-private companies now manage dozens of sophisticated institutional investors.

Most still lack a true investor relations infrastructure.

This will come back to bite you. Once large institutions enter the cap table:

• Communication cadence matters more than ever

• Narrative consistency is critical

• Governance maturity matters

• Guidance and Expectation management becomes a strategic requirement

The modern CFO must increasingly function as:

• Company translator

• Financial storyteller

• Market educator

Even while technically “private.”

4. Operate With Public Market Transparency Internally

One of the biggest risks in hyper-scale private companies is informational asymmetry.

Employees often hold enormous paper wealth but operate with very little understanding of:

• Liquidity timing

• Valuation mechanics

• Dilution

• Tax implications

• Or secondary market realities

This can create bad actor relationships who step in to try take advantage of the private company investor relations weaknesses.

Anthropic just a few days ago dropped a bomb on this very topic

5. Don’t Confuse Valuation With Durability

This may be the most important lesson of all. Never forget that a CFO’s role is to be the counterbalance to the valuation enthusiasm and to ensure the company can grow into its valuation in a reasonable way.

Private market valuations can now reach extraordinary levels before a company fully proves long-term durability.

That creates enormous pressure on CFOs to separate market enthusiasm from business model and operational model realities.

Because eventually, market valuation fundamentals always matter long term

Final Thought

The modern CFO is no longer preparing companies merely for IPO.

Increasingly, they are managing companies that already function like public institutions while still operating inside private-market structures.

That is a completely new leadership challenge.

And the CFOs who master this transition early will become some of the most important architects of the next generation of iconic companies.

“The CFO Playbook for the Rise of the Private Public Company”

If you thought “IPO Readiness” was a “process” you did 18 months prior to your planned IPO, it’s time to reframe being “IPO Ready” in this new Private Company environment.

Become a paid member of this Substack to get access to my upcoming limited seat webinar (I do these monthly). We’ll have a deep conversation on this topic how to become “public ready” while remaining private.

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• How mid-to-late-stage private finance teams need to begin mirroring public company finance organizations much earlier than they thought.

• Secondary liquidity program design - the “public market” inside private companies.

• Tender offers and employee liquidity structures

• SPV ecosystem implications

• Governance evolution before IPO (Security, Privacy, Audit, Compensation, Board)

• The rise of crossover VC investors and how it has created this new environment

• The emerging role of private-market IR (Investor Relations)

• The new CFO skillset required to manage “private-public” companies

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A few prompts and it will produce:

• clear narrative

• structured logic

• smart suggestions

• persuasive language

• even “expert” positioning

While really powerful, the idea AI will take over for everything human is deeply flawed.

AI can’t “stand and deliver”. Well, not until we get Elon’s robot world, and I’m going to strongly argue not even then. It’s not just physically standing or delivering. Humans require human interaction. Once we begin to understand this part of human nature, we can start to visualize where AI’s place in our future world will be… and what it specifically won’t be.

Today’s AI can’t walk into the room with you. It can’t read the room. The tension. The power dynamics. Humans do this in real-time very well. Our DNA is embedded with flight or fight responses that trigger actual emotions. AI doesn’t have emotion. It’s simply generating text on a screen for you.

AI is woefully incomplete in the human influence department. It doesn’t have and will likely never have an “emotional LLM” or “cultural LLM”. Think critically now if you find yourself reactively arguing with me while you read. Ask yourself, where will the LLM “get that data”? Who will code it? Even if some AI tried, do you think THAT version of the “emotions” or the “culture” will be accurate and accepted?

For me, I’ve come to the conclusion this future AI will never be better than humans emotionally or culturally. I’m also convinced I won’t be able to use it to win an argument with my wife! I’ll put that human up against any other human or machine!

Who will train it to slow down at the precise moment? Or to use silence as a strategic influence pause? Maybe AI can be programmed as a video avatar with a screen sitting at a chair and attempt to be better than the humans in the room. But I’ll take the other side of that bet.

My thesis: Your human delivery is required.

The “LLM Illusion”

What we think AI gives us:

“AI can give me the best preparation, the best plans, and if I have that, the outcome will be great.”

Sorry, but again, it’s time to think critically. The human game of life is played on the field, in the heat of the battle, in the moment… not in the “film room”(AI is awesome in the film room!)

Currently, AI mostly only produces words on a page on a screen near you. AI is therefore only potential energy. Your leadership and human delivery is required to deliver the proper kinetic “influence energy”.

AI can help you write the negotiation. You will have to stand and deliver that negotiation.

AI can draft the hard feedback follow up email… but I would strongly recommend against attempting AI delivering that feedback to your direct report.

You still have to be the human in the room delivering the hard feedback with all the required clarity, humanity, and control.

AI can outline the board narrative and even help you create the next board deck.

But it can’t “Lead Your Board”. You still have to hold the room when the questions start rapid firing and the emotions start running hot.

Mind the Gap! The Gap Between Knowing and Doing

Most executive outcomes aren’t decided by only who had the best analysis and thinking.

Real-time execution and performance under pressure when “AI plans hitting the real world” or “shit-hitting-fan decisions” will always be required by a human… in my thesis world.

Leadership and company success will continue to be decided by who performs the best under pressure by:

• Communicating clear thinking

• Communicating with the right timing

• Adapting to live feedback in the moment

• Aligning the room to a shared desired outcome

• Leading the room through and out of the next rabbit hole

This is your job as a leader. AI can’t deliver executive presence or gravitas.

EXAMPLE:

You can absolutely use AI to learn world-class tactics such as being a world class negotiator. At least it can teach it to you on paper… not much different than your undergrad, grad, or masters programs.

When I prompt an LLM to teach me to be a world class negotiator, AI will generate:

• Anchoring strategies

• BATNA framing (best alternative to negotiated agreement)

• Concession planning

• “If/then” trade packages

• Phrasing/scripting for push back

• Objection handling

Great scripts! Thank you AI.

But you are the actor who has to perform the script. Remember, “All the World’s a Stage” and “One Man Leader in their time plays many parts… their acts being seven stages” (ok I butchered Shakespeare to make my point).

“A poor player who struts and frets his hour upon the stage and then is heard no more. It’s a tale told by an idiot… full of sound and fury… signifying nothing.”

In our real world, our scripts break at the sound of the first whistle on the real-life playing world.

Game On!

What matters in the required moment of leadership delivery determines whether you will be a great player (or that shakespearean poor player) since your humanity can deliver what AI can’t:

• the pause

• the pace

• the tone

• the micro-conversation adjustments

• the moment you decide to stop talking

• the moment you decide to ask a question instead of making a point

• the moment you realize the real decision isn’t the one being discussed

• swimming the conversation back to your Islands of Safety

That’s why I titled this post: Your Delivery Is Required. You, the human need to “Stand and Deliver.”

The Room Is a Live System

Meetings aren’t AI documents. They’re living systems.

Every room has:

• hierarchy

• fear

• ego

• incentives

• hidden agendas

• unspoken tradeoffs

AI doesn’t feel or hasn’t been coded for any emotions. Your personal BLM (brain language model) is coded for that.

Which means your edge is not your ability to write. It’s your ability to operate, moderate, and influence. To lead others to find a solution.

To orchestra conduct the room.

Your New Job: Use AI for Drafting. Train Humans for Delivery.

So, here’s my thought model for the week.

Stop treating AI like a replacement for your communication.

• leadership presence

• delivery timing

• calm and clear communications

• room moderation

• strategic set of choices and your Point of View Persuasion

• keeping the room on track for the meetings goals

Our next technology and leadership era won’t reward the best AI prompters.

It will reward the leaders who can take the great content and deliver it under pressure.

A Simple Framework: “Draft (AI) and Deliver (Human)”

Here’s a practical way to think about AI in leadership communication:

1) Draft (AI helps a lot)

• structure

• options

• language

• scenarios

• story-lines

• rebuttals

2) Deliver (human required)

• voice

• pacing

• silence

• presence

• calibration

• empathy

• authority

• reading the room

If you want outcomes, you need both.

The Delivery Playbook

Three tools:

1) Silence is a lever

Most leaders talk themselves out of leverage. The best ones can sit in silence and let the other person fill it. AI doesn’t have a model for that reflex. You do.

Once you’ve made an impact… stop talking. The last “S” in my SECS talk framework.

2) Powerful Questions beat perfect statements

The room usually doesn’t need more words.

It needs the right questions:

• “What problem are we actually trying to solve?”

• “What would have to be true for you to say yes?”

• “What risk are you trying to avoid?”

• “What decision are we really making right now?”

Questions are how you steer and influence the room.

3) Moderation is a superpower

The leader who can moderate a room is the best influencer.

You’ve seen the masters of this, right? Yes, they are using forms of #1 and #2 above. They are constantly scanning the room for who is talking too much. Who is too silent. They are respectfully asking the domineering “voice” in the room to “hear from others”.

Then they steer the room to shared meeting goal/outcome.

Great moderators are the best room readers. They pull the room out of rabbit holes, framing, pacing, translate, and steer the conversation toward the desired shared outcome.

They use key playbooks like my “T-Chart” moderator model or the simple “post-it-notes” on the whiteboard exercise to get people out of their heads and out in the open. Then they astutely point out where the group is aligned and where there is a gap.

They then ask more powerful questions and guide to fill the gaps.

As a leader, take some reps at being a better and better moderator and you will find your leadership influence rise among your peers and your team.

The Bottom Line

AI is definitely awesome on cleaning up writing, researching facts, and creating structured thinking.

But it’s only “thinking” and writing. It’s not actively doing. Leadership is about doing. It’s about influencing. It’s about getting others to follow and take action with you.

Human talents.

Your delivery is required. AI will remain your all-star back room analyst or play caller but you have to run the plays!

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Alex Wu of CFO Advisors and the Stanford Graduate School of Business did the majority of the work here and it’s amazing. Thank you Jeff Epstein (Bessemer) for introducing us. We hit it off quickly resulting in the need to collaborate on this incredibly important startup success topic of “Value Creation” vs “Value Capture”.

Silicon Valley was born from the whole concept of Value Creation while historically struggling in Capturing the Value. Our goal is to combine both into a valuable framework for you to put into your startups practice - starting tomorrow.

EXECUTIVE SUMMARY:

Enterprise AI investment has now crossed $30 billion annually while MIT research continues to show that 95% of implementations produce no measurable return as of yet.

Nobody is arguing AI has created tremendous value in terms of productivity since it burst into the mainstream in late 2022/early 2023. The focus in early 2026 has clearly turned to AI Agents vs Generative AI as the starting point for not just being able to create or generate value but to start capturing it agentically - doing the work that humans would otherwise be doing.

The questions many boards are now starting to ask:

This is the gap between value creation (the original ARR purchase or Free Trial) and value capture (creating a sticky product that won’t churn in 12 months).

This may be the most under-diagnosed risk in venture-backed startups today. Not just getting companies to buy your product but getting them to use it, evangelize it to others, and happy to pay you on the next annual billing cycle.

In this playbook we’ll discuss:

• The distinction between value creation and value capture, and why most startups have it backwards

• How SpaceX, Netflix, and Intercom each organized around a single value creation metric

• A four-step process for finding your value creation metric

• Six most common failure modes

• Why this is the most important yet least discussed tool in a CFO’s toolkit

The AI Success Paradox

Your AI startup feels unstoppable. Inbound leads overflow your CRM. Sales is closing enterprise deals faster than you can hire CSMs. The hockey stick you promised investors is finally here!

The board celebrates every quarter. Record revenue. Record growth. Record valuations. You close your Series B six months after your A before the bulk of customers have even reached a single renewal. You’re crushing it.

Except you start to notice some conflicting signals.

Opt-out cancellations spike at 60 days… but new logos more than compensate. Usage-based credits burn at half the projected rate and implementation timelines stretch from weeks to months. The cracks are there, but who has time to notice?

Investors don’t ask about it. They’re too busy competing to lead your next round. Internally, all these warning signs get rationalized away. After all, if revenue is growing then your product must be driving value… right?

But MIT’s recent study reveals the shocking truth: despite $30-40 billion in enterprise AI investment, 95% of implementations created no measurable return.

The researchers found that most AI pilots collapsed into “brittle workflows”: systems that couldn’t retain feedback, adapt to context, or improve over time.

Initial excitement, zero lasting impact.

These facts beg the obvious albeit uncomfortable questions:

If 95% of enterprise AI deployments aren’t working, what’s actually driving your ARR?

Are your customers buying genuine product value?

OR

Are enterprise budgets simply throwing their cash at the spaghetti wall of innovation hope in a desperate attempt to show AI progress to their own boards and make their “adoption goals”?

The two can look identical on a revenue graph, right up until renewal.

But hey, the ARR graph looks great.

Value Creation vs Value Capture

Every business does two things though we rarely talk about them this way or separate the activity motions clearly:

1. Creates value for customers

2. Captures a portion of that value as revenue

Here’s what Alex and I have witnessed time and time again in our respective careers and networks:

Value Creation is the actual impact you have on your customers. Solving problems, delivering convenience, expanding what’s possible. It’s imperfect, it’s messy, it’s debatable. Your product might solve multiple problems, serve different segments differently, or create value in ways you never intended. There’s no universal formula. That discomfort makes CFOs and board members search for cleaner metrics of customer engagement, customer journeys, and customer storytelling.

Value Capture is what you extract in return. Revenue, ARR, NRR, ACV. It’s perfect, it’s clean, it’s indisputable. Every investor expects these numbers, every board deck leads with them, every startup benchmarks against the same standards. For all its precision, though, value capture only measures extraction. Not whether you’ve earned it.

Most companies have this backwards. They obsess over value capture while hoping value creation happens automatically. They optimize pricing and packaging while the actual foundation erodes beneath them.

The bottom line logic is simple and one we want to strongly emphasize:

The best companies figured this out early. They built their entire operating model around a single value creation metric and let revenue follow:

• SpaceX doesn’t measure success by revenue per launch. They measure cost per ton to orbit. When Musk started, that number was $50,000. Today it’s under $2,000. That 25x improvement didn’t happen by accident, it was the direct result of obsessing over reusable rockets, vertical integration, and simplified designs. The contracts, the revenue, and the valuation are all downstream of that one number.

• Netflix obsesses over hours watched, now over 2 billion daily worldwide. That single metric pushed them toward binge-worthy originals, personalized recommendations, and seamless device switching. Crucially, when engagement drops, they see value destruction happening in real time, long before it ever shows up in subscriber numbers.

• Intercom could measure seats sold or messages sent. Instead they track support cases resolved and time to resolution. Every major product decision from automated workflows, AI-powered responses, to proactive help features flows from that metric. The revenue follows because the outcome is real.

Pricing, packaging, and expansion are all levers you pull to capture value. But they only work if the value is actually there.

Like Newton’s laws of physics, this is a foundational law in business: in the long run, value capture cannot exceed value creation. You can extract more than you create for a while through pricing power, switching costs, or investor subsidies. But the gap always closes.

As I have said many times, “Mind the Gap!”

Customers will find the alternative. Competitors who create more value will take more share. The startups that confused a rising tide of enterprise AI budgets for product-market fit discover, at renewal, that their product value is built on sand.

Finding Your North Star: How to Measure Value Creation

So how do you actually find it? Most founders overcomplicate this. They convene offsite workshops, hire consultants, build dashboards with dozens of KPIs, and still can’t answer the basic question: what changes in your customer’s world when your product works? What stories do your customers tell about your product?

I just wrote a post on building a Customer Operating System to answer just such questions.

Below is our suggested four-step process. If you can answer all four honestly, you’ll have your metric. If you can’t, you’ll know exactly where the gap is.

Step 1: Name the Job

What is your customer hiring your product to do?

• Not what your product does. What changes in your customer’s life when it works.

• The job should be stable even if your product disappears tomorrow. Someone else would still need to get it done.

Intercom’s customers aren’t hiring a “messaging platform.” They’re hiring Intercom to make customer problems go away quickly. The job exists whether Intercom exists or not.

Step 2 : Define Done

How does your customer know the job is complete?

• What would your customer measure, even informally, to know this worked?

• The answer should be something they’d track even if they weren’t paying you.

• Beware activity-based metrics. “They logged in”. HINT: MAUs is not DONE!

A support leader doesn’t celebrate messages sent or tickets opened.

They celebrate cases resolved. That’s the finish line.

Step 3: Identify the Unit of Value

What is the smallest discrete outcome your product delivers that the customer would pay for one more of?

• Strip away packaging, pricing tiers, and bundled features. What is the single indivisible unit of value?

• For SpaceX it’s a kilogram delivered to orbit. For Netflix it’s an hour of attention held. For a payroll company it’s an employee paid correctly and on time.

The unit is a resolved support case. Not a seat. Not a message. Not a conversation started.

A case that ended with the customer’s problem actually solved.

Step 4: Stress-Test Your Metric

Can this metric be gamed, inflated, or improved while the customer gets worse off?

• The customer test: Would your customer independently celebrate if this number improved? If only your team cares, it’s an internal metric, not a value metric.

• The corruption test: Could this number go up while the customer experience goes down? If yes, you have the wrong metric. (Example: “bot deflection rate” can hit 80% by looping customers through help articles that never actually solve the problem.)

“Messages sent” fails the corruption test immediately. More messages could mean worse support, not better.

“Cases resolved” passes: if that number goes up and resolution time goes down, customers are unambiguously better off.

The Six Ways Founders Get This Wrong

1. Defaulting to revenue. Revenue is a lagging indicator that can mask value destruction for quarters before it surfaces.

2. Choosing vanity or “activity” metrics. Total registered users. App downloads. Reports generated. These look impressive and say nothing about whether a customer’s life improved. The tell: a metric that goes up regardless of whether the product is working.

3. Confusing your output with their outcome. Features shipped, tickets closed, emails sent. These measure what your company produced, not what your customer experienced. If only your team celebrates when the number goes up, it’s the wrong metric.

4. Making it too complicated. If your team can’t remember the metric or explain it to a new hire, it will quietly stop influencing decisions. Complexity is how north stars die in practice.

5. Picking something you can’t influence. A metric too far downstream from daily decisions creates learned helplessness. The metric should feel one level out of reach, ambitious but traceable back to daily work.

6. Never updating it. The mistake isn’t changing your value metric as the business evolves. The mistake is pretending it still works when it doesn’t. The right metric at seed stage can become actively misleading at Series B.

The Metric That Matters

Most companies just chase revenue as their north star metric, and 90% of them still fail. The generational breakouts chase something different: a single measure of value creation that captures whether their product is actually changing the customer’s world.

SpaceX bent the cost curve of space access. Netflix reshaped how two billion hours of human attention get spent every day. Neither happened by accident. Each company identified its value creation metric early and organized every operational decision around inflecting it.

This is perhaps the most important and least discussed tool in a CFO’s toolkit.

Value creation doesn’t show up on a P&L. It’s messy, imperfect, and endlessly debatable. That’s exactly why most finance leaders avoid it. But the founders and CFOs who find their value creation metric and organize the entire company around inflecting it build businesses where retention, expansion, and pricing power all become downstream consequences of a problem being solved. Revenue stops being something you chase and starts becoming something that’s inevitable.

Here’s a great quote from a recent panel talk Roelof just gave on this subject:

“Value delivery should come before value capture, and entrepreneurs should focus on creating something useful before thinking about the business side of things.” — Roelof Botha - Sequoia Capital

Roelof had several observations during his talk that illuminate the tension between value creation and capture, especially in early vs later stages.

• In the podcast “Sequoia’s Crucible Moment”, Botha emphasizes that in the early days of a startup, there needs to be heavier weight on value creation over value capture. Build something compelling; make something people want so badly they can’t stop using it. Without that, value capture strategies (pricing, monetization) will be hollow.

• He warns against premature monetization or over-focus on capturing margin before the product and customer foundation is strong. Early capture can undercut growth, reduce user adoption, and limit the size of the pie. (This emerges in his commentary about startups tempted to chase metrics or revenue too early rather than product/market fit.)

• He also stresses long term value creation as a discipline - not just in features or product, but in culture, operating metrics, durability. From his position, a start-up that scales to be one of the “500 most valuable technology companies” is not just one with strong value capture; it’s got to have enduring value creation that customers, markets, ecosystems love.

Scaling Trade-offs

Here are typical trade-offs and how a company should evolve its balance of value creation vs value capture:

Common Failure Modes

1. Value creation without capture: you build something people love (or large usage) but your business model is weak, margins are negative with no clear path. Often seen in high burn, low conversion, or when costs don’t scale with usage.

2. Value capture without value creation: early monetization can drive revenue but if the product doesn’t retain customers, or usage drops, or competitive substitutes emerge, it unravels. Think hard about what you deliver.

3. Over-optimizing capture at the expense of creation leads to incremental improvements rather than breakthrough innovation; you may win short term but lose long term.

4. Misaligned incentives inside the company (e.g. a sales-driven culture pushing pricing up even though product defects or customer dissatisfaction are ignored) that degrade value creation.

Framework for Founders / CFOs / COOs

To operationalize the balance, here are tools and questions:

1. Map the value creation levers: What are the biggest contributors to creating value (product features, service quality, user experience, data, network effects)?

2. Map the value capture levers: What are your monetization & cost levers? Pricing, tiering, margins, cost of acquisition, churn, upsell/cross-sell.

3. Measure unit economics early: even when revenue is small, understand the cost to serve, lifetime value (LTV), churn & retention. These indicate whether capture is viable.

4. Run scenarios of scaling: what happens if you double users but halve monetization per user? Or if you raise prices / shrink features? What are the elasticity & risk trade-offs?

5. Align culture and incentives: reward value creation early (product, engineering, customer success) as well as capture later (sales, finance).

Conclusion

Scaling to a billion-dollar company is not just about aggressive monetization or fundraising. It’s a dance between creating something deeply valuable, and capturing enough of that value to sustain growth, fund the team, creating investor returns, and funding future moats.

Founders who understand when to balance Value Creation and Value Capture are the ones who build legendary companies.

Alex and I also played with AI to create this graphic for this post if you want to use it in your next exec staff or all hands offsite.

If you want to bring either of us or both of us in to speak to your company more deeply on this subject, we are simple LinkedIn message away.

Connect with me

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For startup and growth-stage CFOs, board reporting is typically overcomplicated. It becomes a bloated packet of status updates, data dumps, or a defensive exercise in proving the business is under control.

You walk into the boardroom prepared to defend every slide, row and column. Ten minutes in, the conversation goes off track as board members latch onto minor details, chase rabbit holes, and the clock runs out before you’ve touched the strategic decisions that matter most. Many times you never even touched on strategy in your board deck.

To lead your board effectively, you need to flip the script. It’s critical to structure your board communications on lessons learned and a focus on the future (where you were, where you are, and where you are going). You must control the narrative with a clear point of view and lead your board like any other team. Here is my breakdown of best board practices including what to report, how often to report it, and how to communicate clearly.

8 Best Practices for Board Reporting

The best board reporting comes from being intentional about what you include, rather than simply adding more. These eight practices will help you simplify your reporting, lead with clarity, and keep board conversations focused on decisions.

1. Frame board reporting as a decision-making tool vs. update

One of the most common mistakes in board reporting is assuming the goal is simply to keep directors informed. Yes, the board needs visibility into the business, but reporting should do more than provide status updates. Its real job is to help the board understand the current state of the company in service of a bigger question: what should happen next?

The job of your reporting isn’t to show off what you’ve accomplished but instead, it’s to create context that helps them make good decisions with you. It should show whether the company did what it said it would do and whether the business is performing against plan.

From there, the conversation should move quickly to the future and cover what is changing, what risks are emerging, what decisions need to be made, and where the board can help. The board pack should not read like a retrospective but rather a decision-making tool.

2. Lead the board with a clear point of view

Boards often ask for more. More numbers, more slides, more detail, more comparisons. That does not always mean more information is more helpful.

A useful principle here is that boards need a point of view to react to, not a blank page to fill in. When leadership teams come into a board meeting asking, “What do you think we should do?” they often create confusion. Directors pattern-match from other companies, offer advice based on incomplete context, and generate a flood of opinions that may not fit the business model, market, or stage.

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2 weeks ago I posted the following on LinkedIn. It quickly received nearly 3,000 impressions. Suffice it to say it hit a chord. So, I’m going to expand on this concept here on Substack.

Easter Egg: there’s entertainment in this post… don’t miss the Monty Python and Eminem videos. Who says finance is boring!

I’ve been writing on this consistent theme for awhile here on Substack. Here are some of my previous posts on this subject:

THE WRONG QUESTIONS; FIX YOUR FINANCE STACK FIRST

Every CFO I know is asking some version of the same wrong questions right now:

“Where do I get started with AI in my finance team?”

“What should my AI strategy be for finance?”

The real problem is not where or how to start with AI.

The real problem is to make sure you have the proper data structure before you even think about applying AI to it.

Let me guess. Your finance and overall company data is still too fragmented, unstructured, mislabeled, delayed, or manually patched together. The data you need is still trapped across disconnected systems.

Adding AI on top of that? OOF! Welcome to AI giving you bad answers faster with it’s classic hallucinatory confidence, telling you how smart you are… all with awesome formatting!

So let me say this clearly again: There are 3 main problems in finance and company data today:

1. Data Model Problems (ie - not actually having the right “data model”)

2. Data Integrity Problems (ie - not syncing data consistently and accurately into your data model)

3. Data Observability Problems (ie - not mapping where the data lives so you can extract it into your data model)

Start Up There ^^^^……. Hard Stop.

CFO as Chief Data Officer as Chief Architect

The next generation of great CFOs will need to put on their best Chief Product Officer Hat.

The best Chief Product Officers I know do the following things very consistently:

• Create clear roadmaps of their customer’s journey

• Focus relentlessly on customer requirements

• Define those into key product feature requirements

• Design simple, structured product steps to “aha moments”

• Innovate, measure, and course correct or “experiment, track, and refine”

For CFOs, start thinking of your finance teams data as your “Product”.

You are the owner of this product and you need to focus relentlessly on your “Customer”.

So don’t fall into the FOMO trap of experimenting with AI by running pilots, demos, and experiments against data that was never structured to support machine learning in the first place.

Your new demo might look impressive for the first ten minutes. But look out below when you double click or your CEO or Board asks the next level question.

Your awesome AI now failed. Actually it wasn’t your AI… it was your data architecture.

CFO As Architect

This is where your role and your mindset now has to change.

We CFOs have been historically asked to own the outputs of numbers. To close the books, to forecast the future based on the close, to prepare the board deck to communicate both the actuals and the plan, to track variances, and to be the safeguarder of company assets.

That’s all still true but not enough for the future CFO.

You are now no longer the CFOs who say ERP!

You are now the architects who say “AI” (for bonus points pronounce the “I” as “eee” to match Monty Python below!

The best future CFOs will now have to own the information architecture behind these outputs.

Architects ask different classes of questions:

• Where does this number originate?

• What system owns the truth?

• Which definitions are standardized and which are tribal knowledge?

• Where does my staff “fix” the data manually each month?

• Which sets of data insights are actually reusable data products versus one-off spreadsheet heroics?

• What context and assumptions should accompany the raw data?

Yes, you have to quickly layer AI on top of your data architecture. But AI needs to be at the tail end of the Strategy > Structure > Execution loop.

Your data design and your data model are your strategy and structure, and they must come first before you layer on AI to execute.

So let’s get down to specific steps to make this happen.

Step 1: Hire a data engineer onto your finance team

All great Product Managers partner or hire an engineer on their staff.

It’s time for you as the Chief Product Manager of Finance to hire this engineer on your team.

Call the role whatever you want:

• Finance AI Specialist

• Finance Systems Integrator

• Finance Data Architect

• Finance Engineering Lead

I care less about the title and more about the vision and mission.

I’ve laid out the vision above. Your mission (if you choose to accept it) is to architect the finance data environment so that the AI machines can actually be useful.

The person in your new role is not there to build vanity dashboards or to simply automate the manual. This new role needs to design and build the foundation of your future finance team value:

• Map the data model

• Define system ownership

• Clean up broken data flows

• Create structured context across disconnected systems

• Reduce manual interventions and reconciliations

• Design the connective tissue across ERP, CRM, billing, payroll, HRIS, procurement, data warehouse, and planning systems

• Build the cross checks to make sure your new data model stays clean and connected over time, not just every time you go to clean it up

Hint: You may need more than 1 role for this function and you must now start rationalizing the ROI of such roles or you and your team will be architected out of the value such data and insights created by somebody else in the org.

Step 2: Build and Maintain Your Finance Data Stack

Think in layers:

Layer 1: Source Systems (ERP, CRM, Billing)

Layer 2: Data Model Layer (standardized definitions)

Layer 3: Integrity Layer (clean, reconciled, trusted)

Layer 4: Observability Layer (alerts, anomalies, monitoring)

Layer 5: AI Layer (only now does AI work)

Step 3: Act Like the Product Owner You Now Are

Your finance data is now “the product” and you own it with clear customers.

That means:

• SLAs to Customers

• Bug fixes and Version controls

• Continuous feature improvements

• Customer Listening Tours

3 Root Cause Failures:

It’s critically important to predict root cause failure analysis. All great operators and product managers think to the future in order to work backwards to today. And they think in terms of success and failure at each point in time. So if the above was all about how to succeed, the below will be your warning signs for failure and where specifically to look for the weakest chains in your new data model architecture.

In the end, most AI failures inside finance trace back to one of the three root causes:

1. A data model problem

This means the information itself is not structured well enough to support reliable output.

Where to look:

• Inconsistent chart of accounts mapping

• Revenue definitions changing by team

• Fragmented contract data (data context living in multiple systems or the context doesn’t “live” at all and was never captured)

• Inconsistent time periods or naming conventions

• Weak dimensional modeling in your data warehouse

As I write the above, I’m now thinking to myself that AI could possibly be used to uncover the anomalies above?

2. A Data Integrity Problem

• Poor master data hygiene

• Customer records that do not reconcile across systems

• Missing contextual metadata (key assumptions, relational data)

• Manually maintained spreadsheets acting as shadow systems

3. A Data Observability Problem

This means the data may exist, but you cannot reliably monitor, trust, or explain what is happening to it over time.

Examples:

• Broken pipelines nobody notices for days

• Silent field changes upstream

• Delayed refreshes

• Unexplained metric movements

• Failed syncs between systems

• No alerts when data quality degrades

• No audit trail for how a number changed

• No confidence scoring on inputs

In this case, the issue is not merely that data is messy.

The issue is that the mess is invisible until a board meeting, a forecast miss, or an audit surprise forces it into the light.

Please, please, please never forget and always remember:

Trust in finance is built not just on correct numbers.

It is built on 3 pillars:

• Accuracy

• Consistency

• Timeliness

While Confidence and Credibility is built on:

• The Insights and Value Add You Bring to the Numbers

Build a Finance MCP for Proper Data Context

AI does not only need properly structured data. It needs context.

It needs structured access to how your business defines customers, contracts, revenue recognition logic, headcount categories, departmental ownership, approval rules, scenario assumptions, historical exceptions, and policy boundaries.

To make this crystal clear: “Data Tables” are awesome but tables are NOT CONTEXT!

Excel rows don’t product reasoning.

Capturing insights is not truly understanding.

You need to build a clean context layer across your finance data and systems so that the AI can retrieve the right definitions, relationships, and rules in the right way at the right time.

The headline here?

You must design and build context into your data architecture.

Maintain the context. Provide access controls.

You must be able to drill down and eliminate any AI hallucinations or confidence masking the inaccuracy it might produce.

The future finance stack must be able to use Layer 5 (AI) to produce the Accurate, Consistent, and Timely Data of which we speak!

As Eminem so classically rapped, “This is your moment… you own it!” Your leadership moment. Your systems moment. “You get one shot. You better never let it go. Once in a lifetime.”

The future CFO will architect the company’s financial intelligence layer.

5 questions every CFO should ask right now.

If I were sitting in your seat this quarter, I would start here:

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Convenience wins. Every time.

While most other companies are competing on “better features”, “higher power”, “speeds and feeds”, and even “lower price”, the surprising winner is the one with the most convenience. Hard stop.

The company that removes friction, simplifies effort, and fits naturally into how people already live and work almost always wins every category.

Convenience has been the David against the Goliaths again and again. The companies I’ve been involved with - Intuit, Netflix, and Mozilla Firefox - could root the reason for their success in convenience.

Quicken vs. the Checkbook Register

In the early 1990s at Intuit, we weren’t trying to “revolutionize finance” at first.

We were solving a painfully mundane problem.

Balancing a checkbook is annoying. Manually. With a pencil on paper. Yes, this was once a “thing”.

People were manually writing transactions into paper registers, doing math by hand and trying to make their chicken scratch equal their bank balances. Quicken’s promise that launched its now $100B+ enterprise value didn’t try to make people wealthier. It didn’t optimize their portfolios. It didn’t promise alpha.

It was simply more convenient than pen and paper to track your spending and to reconcile your bank account.

• Faster

• Easier

• More accurate

• Automatically reconciled

That was it for the first few years. That’s all customers could absorb in the early days of desktop computers and software.

In fact, the marketing tag line for several years was simply “Fast and Easy”… printed on every software box, every end cap aisle marketing brochure.

QuickBooks was launched a few years after I joined Intuit. QuickBooks was aimed at small businesses and the financial statements they need to produce for taxes and bank loans. QuickBooks - the very first accounting software product ever to perform the classic “Double Entry” accounting for you. Every other product required you to use the software to make an income statement entry, a balance sheet entry and do actual accounting! (Albeit with a piece of computer software now).

QuickBooks’ convenience? No double entry accounting.

We merged with TurboTax a few years after that. TurboTax’s huge convenience = 1 question at a time. Sure there were 200 questions but we built the % progress bar and showed your tax refund (or amounts owed) as each question was answered. We produced very detailed experts for each question embedded into the question on the screen.

TurboTax’s Convenience? Your Tax Expert came to you, asked you questions, and you answered them the same way you answered the human tax expert. You just did it a lot faster and easier now. Every other tax software product of the day (and this is hard to believe but true) literally mimicked the painful 1040 Form on the computer screen, small fonts and all, no line spacing. Nearly unreadable.

Convenience doesn’t just win customers, it creates new habits and rabid evangelical type customers.

Evangelical customers create moats.

Netflix vs. Blockbuster: No Late Fees, No Car Keys

Blockbuster didn’t lose because DVDs-by-mail was awesome and worked. Though both were true. We were told we were crazy after all and “That Will Never Work”.

Blockbuster lost because Netflix was simply more convenient. Going to a store was a hassle and late fees created lots of friction and angry customers.

At Netflix, we removed friction everywhere:

• No driving

• No parking

• No lines

• No “out of stock” movies

• No late fees

• Movies show up in your living room. Movies go back.

• Repeat.

Blockbuster optimized stores and made nearly all their profits on the candy and popcorn sales near the register and a huge amount on “Late Fees”.

Netflix optimized our customers’ time, their efforts, and the predictability of which next movie they were going to watch vs “let’s drive to Blockbuster and pick out a movie.”

Netflix’s real moat wasn’t our envelope operations.

It was our software-driven convenience. Our inventory management systems, recommendation engine, and operational logistics intelligence that all worked together to make the customer experience both effortless (convenient) and joyful.

Convenience isn’t always obvious and doesn’t always look flashy. Most times, convenience is hard coded into the operational excellence behind the scenes.

Firefox vs. Internet Explorer: Faster (speed), Easier (tabs), Trust (more secure and not Microsoft)

At Mozilla, Firefox didn’t win because we were “open source.” We won the early days of the browser wars because Firefox was simply faster and easier to use, and we could be trusted.

Tabbed browsing meant fewer windows. Faster performance meant less waiting. Better security meant less anxiety.

People didn’t wake up one day in 2004 wanting a new browser, but when they saw it and used it, it simply worked they way they worked. The web was less painful to navigate, and it was fun.

Many times convenience isn’t just about speed or ease of use, sometimes it’s about cognitive load. Firefox reduced mental friction at internet scale with all sorts of easier ways to search (built in search box) or bookmarks or our “Awesome Bar” - where when you started typing into the URL bar, Firefox would help you predict what you were looking for and show you drop downs of options.

Airbnb: Convenience Beats Hotels

Hotels optimized physical locations and fancy buildings. Airbnb optimized simply finding a local place to stay and staying in the comfort of a nice clean home of somebody else.

Search, click, book. Pictures of the place. Reviews from others. Several choices for any given location. Often cheaper and allowed consumers to quickly choose and visualize their stay from so many aspects.

The best AirBnb homeowners became personal concierges offering local activity ideas and places to eat and shop.

What started as convenient couch surfing turned into a much more convenient way to remove friction from discovering new places, trusting the place before you booked, and the convenience of the pre and post transaction experience with the homeowner.

Uber → Waymo: Removing the Last Step

Uber didn’t win because it was a better limo service.

It won because:

• No phone calls

• No cash

• No guessing when the car would arrive

• No explaining directions

Massively convenient.

One tap. The car came to you on whatever street corner you were on. The ultimate inconvenience. Uber launched a whole new industry of “Company/Product Comes To You”.

Waymo is simply the next logical extension:

Remove the remaining friction of the driver and potential bad interactions.

The arc of each evolving “better product” is clear:

Each generation removes another layer of friction.

Pattern Matching:

Across every example, the winning company asked better questions:

• What step can we remove?

• What decision can we pre-make?

• What uncertainty can we eliminate?

• How do we create a “wow experience” at each step of our customer interaction?

Amazon: Convenience as a Religion

If there is one company that turned convenience into a foundational operating principle, it’s Amazon.

In my early days of e-commerce, most in the industry would rattle off the new industry rested on 3 pillars.

• Selection

• Price

• Convenience

Every time this was said, I would express “Wrong order”. Convenience is too far away and should be #1, and Price is a distant last place.

Amazon didn’t win because it was the cheapest. Others were just as cheap.

It didn’t win because it had the best-looking website. Not even close. Its websites for the first 10 years were downright ugly.

It didn’t even win because it had the most selection or the cheapest price. It had neither for the first 10 years.

Amazon won because it made buying things unbelievably convenient.

• One-click ordering.

• Saved addresses and payment methods.

• Amazon Prime (the original SaaS; Shipping as a Subscription).

• Relentless focus on delivery speed.

• Clear, predictable return of orders.

Every Amazon decision was filtered through a single question:

“How do we make this easier and faster for the customer?”

Jeff Bezos famously described Amazon as being “customer-obsessed.” What that really meant in practice was friction-obsessed. For Amazon this meant identifying and eliminating every small inconvenience that stood between the customers intent and the order button and the “wow” emotion when the product showed up way earlier than expected.

Prime: Buying Time, Not Shipping

Amazon Prime wasn’t a loyalty program. It was a convenience subscription.

By pre-paying for shipping, customers removed the mental tax of asking, “Is this worth the shipping cost?” The decision friction disappeared. Ordering became default behavior.

Prime didn’t just increase order frequency. It rewired our consumer psychology.

Convenience isn’t just about speed; it’s about removing decisions.

Amazon’s Operational Logistics Moat:

Like Netflix, Amazon’s greatest advantage remains mostly invisible.

• Warehouses positioned close to demand.

• Software that predicts what you’ll likely buy and accessorize the thing you bought.

• Logistics systems that continuously optimize routes, inventory placement, and last-mile delivery.

Customers experience convenience.

Amazon made huge investments that other penny pinching e-commerce thought was crazy. Amazon spent arguably over $100B over the last 20 years to hide the incredibly complex warehouse and shipping logistics.

That trade of absorbing operational complexity so customers don’t have to experience it is the defining pattern of every category winner.

The Amazon Lesson for Leaders

Amazon proves my “Convenience Manifesto”.

Convenience isn’t a feature. Convenience is a system.

It shows up in:

• Product design

• Supply chain decisions

• Pricing models

• Return policies

• Internal metrics

• Capital investments

Most companies ask, “Is this efficient for us?”

Amazon asks, “Is this easy for the customer?”

And then they build the operations required to make that answer “yes.”

The Leadership Lesson

If you are a founder, CEO, CFO, or product leader, ask yourself:

• Where are we asking customers to work too hard?

• Where are we pushing complexity onto them instead of absorbing it internally?

• What are we optimizing for internally that makes life harder for our customer?

Ask Your Product and Engineering Teams

• Are we designed around convenience?

• Are we faster and easier at every customer interaction?

• How do we remove friction?

• Are we creating Aha! and Wow! Customer moments?

Silicon Valley history is remarkably consistent on my convenience point:

Pick your company. Pick your product. Pick your era.

Convenience always wins. Convenience is king.

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I’ve posted a video at the bottom of this post. Scott and Tom are discussing how we approached customers from day 1. Scott/Tom have story told this dozens of times to every new hire face to face for several years in the early days. I will never forget being one of those new hires at the age of 25 and with only a few other new hires in the room listening to these same origin stories and critical customer lessons.

I’m paying forward these lessons today to any founder or exec team so at a minimum somebody someday even many years in the future will discover these critical lessons and to make sure they are not forgotten.

I hope you read how I recommend turning these lessons into a Customer Comes First Operating System, but at a minimum, I hope you simply watch the Scott/Tom video. P.s.: I have several more of these on different topics stored on my YouTube Channel

My post today will take these customers lessons a layer deeper and suggest a new “Customer Operating System” to help turn “Customers Come First” from a high level slogan to actual company activities at all levels of the employee and leadership base.

I’ve never seen these lessons fail when applied. I brought these “customer first” techniques to Netflix and Mozilla and coach them when I can in every other startup I’ve interacted with.

I strongly believe that almost every successful company who has navigated from startup to unicorn has the foundations of being very close to their customer. I also strongly believe the opposite is true. Technology first companies or companies that state “customers don’t know what they want” and “we know better than our customer” are bound for the killing fields of Silicon Valley.

At the core of what I’m now calling the “Customer Operating System” are 3 simple words and 2 key sentences.

Customers Come First.

If it’s good for the customer, it’s good for the business.

If it’s not good for the customer, it will eventually break the business.

Thank you Captain Obvious!

But I remain surprised how often the core of the company problem is not being close enough to your customer. I’ve come to the conclusion that many don’t know how.

This simple concept is therefore worthy of a post but also worthy of my attempt to create an actual repeatable customer operating system.

Why Startups Lose Customer Touchpoints As They Scale

The classic phrase gradually, silently, and then suddenly applies here:

• New layers of management appear.

• Product becomes technology roadmap driven instead of customer requirement driven.

• Actual customer conversations get replaced by internal naval gazing operating metrics and dashboards.

• And the most dangerous I hear? “We know what our customers want.”

The Best Customer Focused Companies?

• Design customer touchpoint rituals at every product stage

• Talk about the Customer Journey constantly

• Think and communicate “Customer 1st” not only to the company but most importantly to the customer whenever issues arise

• Create extremely valuable Customer Communities

The Powerful Questions To Ask Your Team Today

Three Questions

Using my Powerful Questions Framework, every leadership team should revisit these 3 questions quarterly:

1. How close are we really to our customers?

Evidence-based, not belief-based. When was the last time the CEO and the Exec Team actually spoke to customer(s)?

2. Who owns our customer engagement?

If the answer is “everyone,” then the answer is actually “no one.”

3. What are our customer-backed rituals?

What do we actually DO to prove we are close to our customers? Specifically. Go ahead, I’m listening.

Cook’s Customer Operating System:

5 Customer Sub-Systems

Below are the actual customer rituals we used at Intuit, plus two cultural programs that became legendary. These forced every employee, regardless of title, to stay connected to real customers using the product in the real world. I participated in each one of these and they imprinted “customer” on my personal startup DNA.

1) Follow Me Home (FMH)

The most powerful customer-learning mechanism I’ve ever experienced.

We (as in the entire company of 400 people) went to actual customer homes of those using our actual product (Quicken and QuickBooks at the time). The FMH system required us to only watch quietly and take detailed notes to pass back to our product and engineering teams.

We were not allowed to help the customer as they struggled through various parts of the product as they used it in the “real world”.

Every employee was also required to be a “phone customer service rep” for 1 week a year (no internet or email service existed back then).

The product/engineer teams then prioritized the “customer requirements” for the next product version after pattern matching over a few hundred customer interactions over a very short period of time. FMH produced decades of product improvements because it revealed friction customers didn’t even know how to articulate.

You may not be able to actually visit your customer’s homes or even have a customer support department but the framing of figuring out how to communicate 1:1 with customers is something I highly encourage you to figure out. Get creative.

2) The National Sales Tour: “Everyone Sells for a Week”

Every year, we sent every employee, yes, every single one of us to a major city of their choice (requirement was you had to stay with a friend or family member - to save the company money).

We all went into the major software stores of the day (Comp USA, Babbages, Egghead, etc) to speak to the store managers and to rearrange the boxes on the shelves to make Quicken, QuickBooks, and TurboTax front and center and to watch how customers bought the product. We were all sales reps for the week and were armed with key scripts and marketing materials from our sales and marketing departments.

Today, there may not be a “store” but the concept remains the same of having every employee at all levels (especially the execs) attend “Sales Calls.”

While FMH (Follow-Me-Home) taught us where the real “bugs” were in the product post sale, our National Sales Tour taught us what the roadblocks were to customers actually buying the product.

3) Customer Journey Mapping: With a Real Owner

At Intuit, we defined and operationalized the original “customer journey.”

We built cross-functional customer journey maps showing:

• How customers discovered the product

• How they decide to buy

• What they did next on each screen

• Where they get stuck and were creating product friction

• What they told their friends and family about

Intuit made exec team leaders accountable for owning the customer journey from the Sales Department linking to the Marketing Department linking to the Engineering/Product Department and linking to the Customer Service and Support Department.

There was no way for finger-pointing and department siloing to occur. We even designed joint compensation incentive programs cross functionally. We made sure the cross functional leaders (Head of Product + Head of Engineering + Head of Marketing) spoke as 1 voice and appeared “on stage” together at all hands meeting. I have strong memories of 2, 3, and sometimes 4 execs on stage in front of the company talking about how they work together with their customer at the first set of operational hand-offs.

We published weekly and monthly reports and led all quarterly offsites and QBRs (quarterly business reviews) starting and ending with the customer journey.

4) Customer Community

In the early-mid 90s, Intuit didn’t have the internet, websites, or customer community software platforms. We were shipping our product on floppy discs and CDs after all. Our version of “customer communities” required in-person observations and structured programs.

Today, companies have a massively more scalable tool called the world-wide-web and still aren’t using this powerful tool very well.

A Customer Community is much more than a support forum or a feature request list.

A Great Customer Community?

• A digital town square for customer feedback

• Real-time focus groups

• Product walk throughs and tutorials ideally created by other customers who are incentivized to share how they use your product

• Customer “tips and tricks” treasure chest of data. Customers love learning from other customers.

• Roll your own idea here

The value of a great customer community is not passive content published to customers or quarterly surveys of these communities. It’s the unfiltered real-time conversations that are happening daily.

When customers talk to each other and to the company, three powerful things happen:

1. You hear their language… not yours.
   This shapes your messaging and positioning far more effectively than any marketing brainstorm ever could.

2. You see their real workflows, hacks, and workarounds.
   Those product gaps? Yes those. Those friction points. Yes those. Those contextual nuances that are hard to replicate in a “survey.”

3. You get the “long tail” truth.
   Customers tell your support team or sales team one thing. They tell other customers the real thing.

Yes, dig for this and you will strike gold.

Customer Communities Are Your Strategic Weapon

1. Customers learn from each other faster than they ever will from your marketing or sales messaging or your customer engagement team.

You will achieve true ROI in lower customer support costs, increased organic product marketing and faster customer onboarding.

2. Company leaders need to be customer moderators vs product broadcasters.

When executives including CFOs and COOs quietly monitor ongoing discussions, they gain:

• Raw behavioral insights

• Feature prioritization signals

• Patterns of frustration

• Patterns of delight

• Real customer vocabulary

• Early warning indicators of churn

These insights feed back into your Strategy–Structure–Execution system with clarity and precision.

3. A Customer Community is the ultimate customer research engine.

No incentives needed. No artificial environments. Customers simply talk and you listen.

The natural conversations that happen in a healthy Customer Community are more valuable than any paid research study, and if you listen deeply you will hear:

• What customers wish the product did

• What they ignore

• What they brag about

• What they teach each other

• What they fear

• What they struggle with

• What they’ve hacked together that you should build natively

Hint Hint: The Seeds of Your Future Product Roadmap Begin Here!

CFO + COO Role in Customer Community Design

Open your checkbook and allocate your $ to creating this Customer Community.

If you want to be a key architect of the business, then invest in it, design it, build it, and create your new customer insights engine.

Now you can turn this customer data into customer insights and into customer decisions. Data > Insights > Actions - your new Customer Operating System.

5) Customer Conferences

In the early to mid 90s and still existing today, there were only big annual conferences that all companies attended (Comdex, CES, others).

Today, the big companies (Salesforce, Oracle, Apples WWDC, etc) hold their own huge customer conferences. Take a page out of their book and invest in your own smaller annual customer conference. Bill.com, Netsuite, Twilio and many others all used this very valuable customer playbook with huge ROIs.

Very few startups invest in bringing their customers together early enough. But those that do are building powerful communities extremely quickly. Key examples are the recent conferences from the Operators Guild that Casey and Molly and team are running, Rillet (Nicholas and Stephen), Campfire (John G), Runway (Siqi), and the a16z demo events that Ivan Makarov is running extremely successfully.

A Customer Conference

For decades, the world’s most iconic companies have built empires around this idea:

• Salesforce → Dreamforce

• Oracle → Oracle World

• Apple → WWDC

• Google → I/O

• Microsoft → Ignite / Build

These events aren’t as much “marketing events,” they’re other customer community events where customers, partners, and company employees all:

• Teach each other

• Share success stories

• Reveal pain points

• Build a deeper community network

• Strengthen brand identity and culture

• Drive roadmap influence

Startups often assume they’re “too small” for a customer conference.

Sorry, that’s just wrong and penny wise-pound foolish type thinking.

You’re never too small to bring your customers together.

In fact, the smaller you are, the more critical it is.

Why Customer Conferences Matter; Especially for Startups

1. Customers Learn from Each Other

This is the magic.

Customers learn 100x faster from each other than they do from you.

They share:

• Workflows

• Hacks

• Best practices

• Integrations

• Creative solutions

• How they’ve structured their teams

• How they drive ROI with your product

These are insights you cannot manufacture internally.

2. Employees See the Customers They Work For

• This ignites a new customer first culture inside your team.

• Your engineers talk to real customers. You can’t get this anywhere else.

• Product managers receive live feedback.

• Customer Engagement takes learnings from 1-3 intense days to prioritize their next quarter’s initiatives.

• Executive Leadership hears the truth without filters.

• Everyone is reconnected to Company Purpose and Customer Impact.

3. You Get Gold-Like Customer and Product Insight

No survey can match the quality of insights gained from:

• Roundtables

• Q&A sessions

• Product demos

• Roadmap previews

• Customer story panels

• 1:1 customer conversations

Your company walks away with a validated roadmap, a clear prioritization reset, and a renewed sense of direction.

How to Build a Startup-Scale Customer Conference

You don’t need Moscone Center.

You need intentionality.

Start small:

• 5-10 customers

• Local venue

• One-day format

• 2–3 customer-led sessions

• 1 roadmap keynote

• 3 hands-on breakouts

• A simple “Ask Me Anything” with founders and product leaders

This is the mini-version of Dreamforce; the startup edition.

Over time, scale it into:

• 25-50 Customers

• Regional Customer Groups

• Quarterly customer meetups

• A flagship annual customer summit

You’re not building a 1-off event.

You’re building a customer-powered learning ecosystem.

Why CFOs and COOs Must Champion Customer Conferences

This is not a marketing initiative nor a sales effort. This is a company investment.

CFOs + COOs are the lead investors: The ROI?

• De-Risk the Product Roadmap

• Operationalize learnings into next quarter’s and/or next year’s planning

A Customer Conference pays for itself 10x. You’ll see it in:

• Renewal rates

• Upsell opportunities

• Product improvements

• Reduced churn

• Market positioning

• Community formation

• Brand trust

• Employee engagement

Trust the ROI: These events are one of the few “high-cost line items” that is actually a multiplier, not an expense.

How CFOs and COOs Can Help Architect the Customer Operating System

Lead with my Strategy–Structure–Execution philosophy. Remember, you sit at this unique intersection of all three.

I can’t tell you how many times I still see customer data being silo’d and filtered inside a startup and even a later stage company.

Product sees one part of the customer journey.

Sales sees another and many times blames Marketing.

Engineering finger points at Sales for selling something we haven’t built.

Onboarding and Customer Engagement sees a whole other side of the customer.

And the leaders and their departments are not talking to each other with a customer first mentality.

As an operator, a CFOs or a COO, you see the full system. You see:

• Customer Pipeline Issues

• Customer Onboarding Friction

• Customer Churn Signals

• Customer Recurring Revenue and Expansion Patterns

• Customer Value Creation

• Customer Value Capture

• Customer Value Destruction

I’ll continue to shout that the CFO/COO is the natural operating architect for the company and it all starts and ends with building the internal operating system from a Customer First Philosophy.

You will know when you get it right and will certainly know when you get it wrong. You can feel the customer heartbeat of the company and build that into higher quality and higher velocity decisions. You can drive company alignment from the customer backwards to operational ownership.

These five programs alone can create a moat most competitors never build.

QUARTERLY CUSTOMER JOURNEY SCORECARD: CFO/COO LED

Try to do this at least every quarter, certainly no later than every 6 months. Leadership should ask these questions:

The 12-Question Cook’s PlayBooks Journey Review

1. Where are we losing customers?

2. Where are customers teaching each other?

3. What are our customer’s biggest friction points?

4. What do Follow-Me-Home Customer Sessions reveal?

5. Top 3 things we learned from our Customer Community?

6. What did customers say at the conference?

7. What is the #1 avoidable loss reason?

8. What is our fastest-growing workflow?

9. Who are our best customers and why?

10. Who are our worst customers and why?

11. What are we overbuilding/underbuilding?

12. What is our #1 single most important customer insight this quarter?

Build Your Customer Moat: Get Started Today

Moats built around the customer and their loyalty is something that AI and competitors can’t copy.

Competitors can try to compete with product features or pricing but a strong loyal customer base who knows they are getting what they pay for is more valuable than any product or pricing sleight of hand.

The greatest companies ever built truly understand this and the ones that fail, failed to ever understand being this close to the customer.

So, copy/paste the above and start building your own Customer Operating System starting today.

SPEAKER / KEYNOTE OPPORTUNITY: Book Me To Talk About This.

If you want me to personally come in to deliver this keynote at your next company all-hands or leadership team offsite, contact me. Yes, it’s that important!

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Naturally, they focus on more precise models and create systems and subsystems to try to design for accuracy. They can’t wait to perform their month end Plan vs Actual to see how accurate their forecast was and then to build a new model.

Houston, we have a problem! That’s an ode to just launching Artemis to the Moon and sending humans around it for the first time in 50+ years.

The best FP&A teams are not about that. You and your team will crash and burn on landing with that mental model.

Your FP&A team should be designing for agility… not accuracy.

It’s time to design a decision-response system.

The Best Finance Teams

The best finance teams are intellectually honest about one thing:

All forecasts are wrong.

The best FP&A professionals know that forecasting with multiple variables is the equivalent of gambling. Being highly accurate in a multi-variable model is not statistically possible.

Unless you are a very late-stage or quarter-to-quarter public company, designing for decision agility is what your high growth scaling startup needs from your team.

Most of you already know your forecast is highly sensitive to overall market conditions, industry or customer surprises, government policy changes, and even natural disaster or mass internet outages.

Look at what happened to your forecast in just the last 30 days with the Iran conflict.

The top 1% of finance leaders design a decision-response system knowing their forecasts are going to be wrong.

They don’t just plan the future, they create scenario planning and they pre-wire the next set of decisions to keep driving their key metrics toward the overall goals.

They build these pre-wired decisions into their FP&A “system” and build the “next decisions” into their next forecast model along with the detailed assumptions.

Planning Three Steps Ahead Is Table Stakes

Every great CFO, VP of Finance, or FP&A leader knows the mantra:

“We need to plan three steps ahead.”

So we build:

• Base / Upside / Downside scenarios

• Sensitivity tables

• Waterfalls and bridges

• Probability-weighted forecasts

These are all great work products from the great FP&A teams to be able to see into the future better.

My key question?

“What do we need to DO in the future vs SEE in the future?”

Seeing more accurately into the future stops one step too early and keeps your FP&A team from being more influential in driving strategic future decisions.

Start incorporating a new decision-response system into your financial models. In the past I’ve called this pre-wiring the future decisions and summarized it as “course correcting”. It’s all the same concept.

Decision-Based FP&A

A forecast without a decision is just a prediction.

If you want to be an elite FP&A team, please start treating forecasting as THE INPUT…NOT THE OUTPUT.

Start asking a different question for each forecasted scenario… for each line/variable/assumption in your forecast.

“If this scenario becomes true, what decision do we make?”

“If this line item executes beyond it’s maximum expected outcome range, what is our next decision for that line item?”

“If it’s below the minimum expected range?”

Now code both the line item or scenario assumptions and the “next decisions” for that line item into the actual model. Go ahead, I’ll wait. I hope you tagged that row/cell data with the proper notes and narratives.

As your FP&A team’s leader, coach them to make the shift from:

• Forecasting the future to Deciding the future

• Planning scenarios to Pre-wiring responses

• Predicting outcomes to Designing course correcting actions

Pre-Wiring Decisions: What It Really Means

Pre-wiring means you don’t wait for a variance to show up before acting.

You decide in advance:

• What actions you will take

• Who owns the decision

• When you will move

• How much to increase or decrease your inputs or investments

• What tradeoffs you will accept

Do I need to say it again? Ok fine. The… forecast… will… be… wrong.

You may as well decide now (as in today) what to do WHEN the forecast will be wrong vs waiting for that future day.

Examples:

• If product or engineering misses their next product launch milestone date, pause those sales reps tied directly to that product. You can’t sell what isn’t in market after all.

• If you are within 6 months of cash runway and the VC you’ve been courting for 3 months passes, and it’s late October (with Thanksgiving and Christmas breaks coming up where the VCs start signing off), you freeze new hires until you have a signed term sheet.

• If the new marketing campaign doesn’t create your MQLs (marketing qualified leads) for 2 straight months, you execute campaign B or campaign C… you don’t keep hoping the original campaign will start working.

• By the way, with fewer MQLs for 2 months, you need to now pause your new hire SDRs (sales development reps) since your current SDRs are starting to surf Instagram more and more on the clock.

• Roll your own. Pick your line item. Create your ranges of Bad, Good, Great.

• Now create the “response decision” if the actuals fall below bad or rise above your great range.

This is no longer a forecast. It’s not even a “Financial Plan”. You’ve now created a “Financial Decision System”. You lead and influence the strategic future decisions of how we’ll respond when the actuals are significantly off the last set of assumptions.

Coach Your Teams To Stop Asking:

• “Did we hit the forecast?”

Coach Them To Start Asking:

• “Did we respond correctly when we didn’t?”

That’s a fundamentally different financial operating model.

FP&A as Decision Architecture

Old model:

• Build the plan

• Track variance

• Explain what happened

Modern model:

• Model scenarios

• Attach decisions to each scenario

• Create response plan triggers before the actuals come in

This is FP&A decision architecture. The finance team becomes:

• The designer of this decision system

• Focused on navigating against the uncontrollable variables

• You are now your executive peers decision co-pilot to their function

The outcome of operating this way?

• Your company is more agile

• Your decisions are higher quality

• The data drives the decision

• No more opinions or hope

• Reduces emotional debate of “just a little longer”

• Prevents reactive leadership

Your CEOs and Boards will quickly start finally understanding your finance team’s value.

So here’s my reframing thesis I’ll leave you with:

Are you forecasting the future OR are you helping to decide it?

Because planning without pre-decisions is just optimism with spreadsheets.

And FP&A without pre-wired response plans is today’s incomplete decision system.

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If you are one of my CFO Readers, you will want to keep this playbook. If you are another C-Level Exec or a VP or Director trying to influence one, I recommend you talk to your CFO about using some of the techniques and language below.

Let’s start with a key thought model on decision making - the decisions that created your plan and the decisions you now need to make as a result of your 1st quarter’s plan vs actuals:

“Good decisions aren’t about certainty. They’re about confidence, clarity, and the ability to course-correct the decision.”

Every operator I’ve ever coached - CEO/founder, COO, or CFO have all eventually hit the same wall. I absolutely hit this wall early in my career.

We don’t have a consistent way to properly size the downside of risk vs the upside of reward.

So we rely on our instincts, experience, opinions, or we manipulate the data to support our internal biases.

We lack a repeatable system to evaluate the trade-offs that truly determines the quality of our decisions.

Today’s post goes deep into how I’ve learned to size risk vs. reward using the core components of the Decision Making Series I wrote about over a year ago.

My readers know I’ve been working on these frameworks and playbooks as I try to communicate and influence how to be a better decision maker. I’ve introduced concepts such as the Risk Equation, Confidence Scoring, and the Powerful Questions Framework.

After 30 years operating inside Intuit, Netflix, and Mozilla, and now coaching dozens of CFOs and founders, I can confidently say:

CFOs need to learn to influence more. Influence requires their ability to quantify and plan for uncertainty and to communicate this ability effectively.

In order to consistently influence and establish high credibility, I recommend communicating to your peers in the form of a “decision system”.

Let’s unpack some of my own consistent coaching on “decision systems”:

1. Decision Quality = Understanding the Range of Outcomes

Don’t make decisions based on a single predicted outcome. I used to do this early in my career. Our revenue plan is $X. Our cash at the end of the year will be $Y. Then you learn you will never be 100% accurate of X or Y, leaving you to have to explain a variance on why the numbers weren’t X or Y.

Then you learn that wasn’t the point at all. A range of X and a range of Y was good enough to determine success. Below that range was bad and above that range was good.

So start make decisions based on ranges of outcomes… not X or Y.

1. Best Case

2. Base Case

3. Worst Case

Or

1. Minimum

2. Expected Value

3. Maximum

Take your pick, but that’s only the starting point.

The key is to attach specific assumptions, key metrics, and critical timelines to each case.

2. This is where the Risk Equation enters the system

Risk = Probability × Severity

I’ve seen seasoned leaders focus only on the severity part of the equation on both ends of the severity spectrum.

“Even if this is bad, how bad could this be?”

“Wow, the bad outcome could kill us.”

Great operators don’t focus on these extremes of severity. Neither are useful without equally focusing on the probability of the severity.

Probability Analysis is critical in decision making. Example:

“There’s a 1 in 1,000,000 chance the outcome that kills us happens.”

Or

There’s a 1 out of 2 chance (50% probability) of the negative outcome that, while not very severe, will significantly slow us down and set us back.

Elite Operators? They also add Frequency of the Probability to the mix. The 1 in a million chance that only is capable of happening every 10 years is very different from the 1 in 10 chance of a bad outcome whose potential frequency is daily/weekly/monthly.

Here’s my Risk Matrix

To size decisions intelligently and to help influence the room of the “true risk”, I will pull out a simple 2×2 matrix learned from my time with my Security and DevOps teams of the past.

Axis 1: Severity of Risk

(Low → High)

Axis 2: Probability of Risk

(Low → High)

Note: I’ve included the optional Frequency into the Probability axis, since a more frequent chance of risk increases its probability of occurring.

Low Severity / Low Probability

Green Light

Your job? Move fast. Execute cleanly. Remove friction.

These are the “don’t overthink it” decisions.

Quadrant 2: High Severity / High Probability

Red Light

This is where capacity planning, cash runway, and execution sequencing matter most.

3. Bringing Confidence Scores Into the System

One of the most powerful habits you can develop—as a CFO, COO, or CEO—is tagging every assumption with a confidence score.

I use a simple scale:

• High Confidence (70–100%): Supported by data, customer evidence, or repeated patterns

• Medium (40–70%): Directionally informed but incomplete

• Low (<40%): Opinion, hypothesis, or early signal

Now combine this with your risk–reward matrix:

High Risk/Reward decisions with low-confidence assumptions deserve caution, not enthusiasm.

Low Risk/Reward decisions with low-confidence assumptions deserve to die immediately. These decisions either aren’t really “decisions” or even if you succeed in something low reward with low risk… you are likely to ask “So What?”

Confidence scoring forces intellectual honesty.

It forces personal beliefs into a score (a.k.a “data”).

Teams stop arguing opinions and start comparing assumptions.

4. The 5 Powerful Questions That Size Risk Properly

Here are five questions to either include in an executive/board briefing or to ask depending on what seat/role you are in.

1. What must be true for the upside to happen?

List the assumptions. Score their confidence.

2. What is the cost of being wrong?

Financial, operational, reputational.

3. What is the earliest signal that tells us we’re wrong?

Pre-mortem thinking. And when will we first see this signal?

4. How reversible is the decision?

The Bezos “one-way vs two-way door” thinking.

5. What is our cheap test?

Every big decision can and should be tested with a small, fast, low cost experiment to prove the underlying assumptions.

Just asking these five questions will elevate your decision quality by 2-3x. Keep asking powerful questions and you can compound your decision quality even more.

Let’s also Size the Risk: Here are 4 categories to score:

1. Financial Risk
   Cash burn, capex, margin impact, downtime.

2. Execution Risk
   Sequence, velocity, team capacity, cross-functional complexity.

3. Customer Risk
   Retention, experience, support burden, product-market fit.

4. Reputation Risk
   Brand trust, board confidence, stakeholder alignment.

Elite CFOs score all four. How many is your team scoring?

Now let’s talk about the REWARD side of the house. Risk is so negative after all!

Sizing Reward: Start With Strategic Fit

Many startup execs and teams mistakenly judge reward by financial upside alone.

Bad idea.

The best evaluate reward across five dimensions:

1. Strategic Alignment
   (Does it support our strategy, structure, and execution system?)

2. Financial Impact
   (Revenue, margin, cost savings, cash runway)

3. Customer Impact
   (Does it improve the customer journey or customer community experience?)

4. Organizational Impact
   (Does it improve or strain team capacity, hiring, or leadership bandwidth?)

5. Long-Term Advantage
   (Does it build a moat? Capability? Optionality?)

This is where 90% of decisions go wrong.

The reward is not aligned to the strategy. Hard stop.

Bright shiny objects often become the exciting but silent killers of focus and execution.

Summary of My Decision System:

1. Write Down The Decision We’re Making

Make it clear, simple, specific, measurable with documented assumptions. It’s amazing what “Writing It Down” does for clarity.

2. Communicate Your Clear Strategic Thesis for Making the Decision

Your point of view. Your narrative. Your 1st Principles. The “Why”.

3. The Reward (Sized)

Strategic, financial, customer, organizational, long-term.

4. The Risks (Sized)

Probability × Severity + Confidence Scores

Financial Risk, Execution Risk, Customer Risk, Reputational/Brand Risk

5. Range of Outcomes

Best / Base / Worst case with timelines.

6. Early Warning Indicators

Signals we monitor.

7. Make The Recommendation

What we should do, Why, and When. Using all the above as core elements of your recommendation.

Your goal is to build your CFO influence, confidence, and credibility. You certainly have more data than anyone else in the org. It’s time to put it to work in a consistent systemic way such as my example of a decision and communication system above.

Closing Thought

The quality of your decision making system determines the quality of your outcomes.

Good companies rely on intuition.

Great companies rely on decision architecture.

I also love these decision quotes:

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