My closest friends and colleagues know I’m a total geek when it comes to poems and Shakespeare. I regularly write poems to my Annual March Madness Pool to describe the craziness of those few weeks a year. Other times, I’ll conjure up a fun poem to simply get it out of my brain.
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Here’s more on the inner workings/easter egg of my brain’s makeup. My Ohio middle school classical English teachers forced us to recite several Shakespeare sonnets in 7th, 8th, and 9th grades. (Here’s to you Ms. Pease and Mrs. Tomasweski.)
I can still recite 3 of these sonnets mostly on cue. Personally, I think it’s a great cocktail party trick. My friends and family, however, just groan - “No, not again.” But if you see me at an upcoming event, you can ask me to perform, and I’ll gladly do it… and I’ll know you read this post!
Today, it’s time to turn one of those recitals into an actual post and connect it to startups.
The 7 Stages of a Startup
Shakespeare once wrote that “All the World’s a Stage” - the 7 Ages of Man.
Infant (At first the infant mewling and puking in the nurse’s arms)
Schoolboy (Then the schoolboy with satchel and shining morning face creeping like snail unwillingly to school)
Lover (Sighing like furnace, with a woeful ballad made to his mistress’ eyebrow)
Soldier (Full of strange oaths and bearded like the pard; jealous in honor; sudden and quick in quarrel; seeking the bubble reputation even in the canon’s mouth)
Justice (In fair round belly with good capon lined; with eyes severe and beard of formal cut; full of wise saws and modern instances)
Lean and Slippered Pantaloon (the 6th age; with spectacles on nose and pouch on side; his youthful hose well saved a world too wide; for his shrunk shank and his big manly voice, turning again toward childish treble, pipes and whistles in his sound)
Sans Everything (last scene of all; 2nd childishness and mere oblivion, sans teeth, sans eyes, sans taste, sans everything)
In startups, we do the same thing… just in stages.
One person (player) in their time plays many parts… if they survive all seven stages.
Our startup acts being 7 stages:
Founding Stage (1-10 employees)
Early Build (10-50 employees)
Product Launch & First Customers (50-150 employees)
Product Market Fit & Scaling Customers (150-500 employees)
Pre-Unicorn & Internal Company Scaling (500-1000+ employees)
Late Stage Unicorn
Public Company
I’ve also added 7 Key Attributes common (but different) to every stage:
People
Systems
Exec. & Team Leadership
Product
GTM (Go To Market)
Board and Investor Management
Culture
Let’s set the stage with the poem I randomly wrote and kept in my “best ofs” from roughly 5 years ago that inspired today’s post. I remember sending it out on email to a handful of colleagues and then moved on. I’m glad I found it again.
Stage 1: The Founding Stage (1–10 employees)
“At first the founder, where anything is possible. Moving fast with no care for scale.”
People: Founders hire Co-founders. No roles, just contribution. Everyone’s doing everything. Nobody does performance reviews. “Founders Mode”. It’s all hands all the time.
Systems: Google Docs and Notion are your ERP. Slack and sleep blur into one. Daily stand-ups. Meetings? Metrics? Nope, just grabbing somebody and getting shit done.
Exec. & Team Leadership: The Founder/CEO is also the COO, CFO, CTO, and Head of Office Snacks. No time or need to plan or strategize and the “leadership team” are the 10 of you.
Product: The core obsession. Everyone touches it. Speed over Quality. Minimum Viable Everything.
GTM (Go To Market): Founder-led sales, if any. Mostly pitching, not process. The first 10 customers are key relationships.
Board & Investor Management: Friends, family, or angels. Light-touch; Starts with trust and belief. No real board. Lots of “advisors” and no professional investors.
Culture: Culture here is everyday small wins. It’s rituals like daily stand-ups, shared meals, and shared accountability. Bonus here if you can continuously cheerlead through the numerous setbacks and roadblocks. Double bonus if you constantly communicate your operating beliefs, values, and why you believe them.
Stage 2: Early Build (10–50 employees)
“And then the whining Founder, with his pitch deck and reality distortion field…”
People: First signs of specialization. Job descriptions appear. Org charts get drawn and redrawn.
Systems: Still scrappy. You duct-tape dozens of tools including Rillet or Campfire or QuickBooks, Slack, Google Drive, Carta, and Notion. Chaos is still a feature, not a bug. Knowledge lives in Slack threads and Notion.
Exec. & Team Leadership: Founders start letting go. First-time exec hires test culture, trust, and control. First Director and VP-level hires stretch the org chart and challenge the culture and other’s egos. Leadership is still reactive here, however.
Product: MVP proves promise. Now it needs iteration, reliability, and usage metrics. Product roadmaps and product priorities are debated daily.
GTM (Go To Market): Hiring first reps. No playbook yet. Nothing is repeatable yet… nor should it be as customer feedback is critical and listening intently to your first customers is required. CAC/LTV doesn’t exist yet.
Board & Investor Management: The “Board” is really just a bunch of advisors, mentors, and early angel investors. Meetings go from social to semi-formal. Founder updates evolve into the first Board decks.
Culture: Culture begins to shift unintentionally. The closer you get to 50 employees, there will be days where you feel, “Wait, I didn’t interview that person?” or “Who is that new person?” Culture now needs to be modeled, not assumed. The newer employees are watching closely and the true seeds of future culture are planted here both positively or negatively.
Playbook Tip: 7x7 - 7 times; 7 different ways: Both verbal and non-verbal (quick actions) on cultural non-negotiables. Define and defend what is sacred to your culture.
Playbook Tip 2: Start an employee onboarding program with storytelling from founders/execs.
Stage 3: Product Launch & First Customers (50–150 employees)
“The passionate evangelist product lover, with a marketing ballad made to their customers’ eyebrows…”
People: You hire managers of speciality department teams. Org complexity spikes. Silos start to form. Org chart complexity begins, and if you aren’t careful, hiring gets out of control and unfocused and undisciplined.
Systems: Homegrown tools begin to break. ERP and CRM systems get implemented often poorly. Finance, HR, and IT are all under invested. It’s hard to shift away from investing everything into Product, Engineering, and GTM.
Exec. & Team Leadership: The exec team gets tested. Weak VPs get exposed. Strong ones are invaluable. Founders and Leadership must begin to delegate or will be viewed as bottlenecks that all other employees talk about but they themselves are mostly blind to. Start investing in internal and external coaching now (not later). Must start investing in performance reviews, promotional leveling definitions (who and why; and why not promoted). First signs of team and cross-functional team conflicts start arising. Clear swim lanes start forming in Product, Engineering, Sales, and Ops.
Product: Scaling infrastructure. Bugs hurt more. Technical debt appears. Customer feedback must be systematized. Feature prioritization becomes political if there is not a feature priority “system”. If you don’t form your customer community and constant customer engagement in this community, you are falling way behind and are introducing significant future risk.
GTM (Go To Market): Repeatable sales motions needed. Start segmenting customers. Funnel metrics become survival tools and must be tracked. CAC/LTV becomes very, very real… especially churn.
Board & Investor Management: Series A brings required structure. Materials are actually read and reviewed. Meetings go from ad hoc to quarterly. Pressure increases. Expectations of strategic clarity, forecasting discipline, and hiring plans. Start your quarterly investor letter now. You will need this rhythm and rigor for future fundraising.
Culture: Stamp out team conflicts quickly. Hire your first head of people or chief people officer and great recruiters.
Playbook Tips: The people team must build the future “cultural scaffolding” or Cultural OS. This includes onboarding, offboarding, leadership principles and training, shared rituals, and key systems to keep people decisions objective not subjective (e.g. performance reviews, leveling/promotion frameworks, PIPs, All Hands Meetings, Semi-Annual or Annual All Company offsites, and Employee Recognition).
Stage 4: Product Market Fit & Scaling Customers (150–500 employees)
“A GTM soldier, full of product promises and building moats…”
People: Culture starts to dilute. Culture risk is highest at this stage. Culture is either cemented long term OR breaks at this stage. Leadership must actively defend the culture. OG (Original employees; old guard) start to feel disoriented and some get passive-aggressive.
Systems: Must rip and replace key systems again. The band-aid systems that got you here simply don’t scale. Systems must be installed to take you to 1500+. ERP, CRMs, HRIS, DevOps, Rev Ops, Ai Agents. Internal and external system architecture is critical now as are the APIs and integration between systems.
Exec. & Team Leadership: Add CPO (Chief Product Officer), CMO (Chief Marketing Officer), and definitely a CFO… and maybe a COO. The CEO must now scale leadership instead of still being in Founders Mode. The next level of leadership and managers are critical here. They are either your flywheel/accelerator or your brake.
Product: Multiple teams, backlogs, roadmaps. User feedback loops must mature. UX and Product Quality are critical. Customer satisfaction is critical.
GTM (Go To Market): Sales/Marketing/CS specialization. CAC discipline and ARR goals drive strategy. Territory mapping begins. Customer cohorts should be started and tracked if you haven’t started yet.
Board & Investor Management: Strong oversight now. Formal board prep processes. Metrics matter. Strategy, not just updates, is critical during board meetings. Regular quarterly investor communications pays off or not doing it creates investor debt.
Culture: Leadership team needs to reinvest going “back on the floor”. Skip levels, AMAs, weekly all-hands, quarterly team offsites. Team and team dynamics are everything at this stage.
Playbook Tip: Start conducting culture pulse surveys (CultureAmp; Lattice) and act and communicate the results both to the whole company and also deep dive with your own department every 6 months.
Stage 5: Pre-Unicorn; Internal Company Scaling (500–1000+ employees)
“And then the justice…” (seasoned leadership team)
People: Employee experience is now a strategic lever. Turnover can kill momentum. People = Culture here.
Systems: Your internal and external tech stacks become either a moat or an anchor.
Exec. & Team Leadership: Exec and leadership teams become a “system” of their own. Ownership and decision rights must be clear. Seasoned execs begin replacing founding/earlier stage execs. Layering and specializing of roles becomes more and more regular. Defined succession planning for key roles should begin.
Product: Often now multi-product. Platform thinking required. Ops scale and technical debt start to collide. Customer community is more important than ever.
GTM (Go To Market): Full go-to-market machine. Growth teams, partner channels, international strategies may emerge. Global/International expansion planning should begin. Partner ecosystems should be created.
Board & Investor Management: Audit prep, comp committees, quarterly investor updates. Board gets assertive. Eyes are always on next fund raise timing. Real governance begins. Being M&A ready and IPO ready starts entering the discussion.
Culture: Many companies take their eye off their cultural programs here. The best companies make sure there are a dozen or so cultural champions embedded throughout the org. Founders + Current Leadership needs to sacredly protect their invested time in continuing to tell the company story and the company success timelines/history of what got the company “here”.
Playbook Tip: Start a Leadership Listening Tour.
Stage 6: Late-Stage Private (Unicorn)
“His youthful cash, well saved, a world too wide…”
People: Complexity = burnout. Systems, career paths, and clarity fight attrition. Talent Succession and Talent Retention now takes center stage.
Systems: Internal controls must now accompany company scaling and compliance. Investor Data Rooms better be in place here… otherwise this system must be installed.
Exec. & Team Leadership: CEO and Exec Leadership team must delegate properly and create clear ownership, decision making, and accountability systems. CEO and Execs need to be as much as 50% external evangelists now. Conferences, press, future investors. Succession plans are clearly in place now. The best companies have world class advisors and coaches for the key executive team members.
Product: Margins, usage, and key feature milestones now dominate roadmap decisions. Innovation tends to slow as ensuring low customer churn is prioritized over “new”. Product “Horizon Planning” needs to begin.
GTM (Go To Market): International expansion, vertical GTMs, and pricing strategy dominate planning. IPO and M&A Planning becomes a separate internal function.
Board & Investor Management: Final phase before IPO. Pre-IPO prep, banker intros, dual-track planning. Strategic M&A. Focus shifts to optics and story shaping. Metrics must be “market-grade”.
Culture: Be careful of internal power dynamics and dysfunctional cross-functional teams which can become a poison to company culture. Ensure there are no rock-star asshole leaders full of ego and politics. Don’t give anyone a hall pass or rationalize away your cultural code because of all star performance. How your team performs is just as important as to what they’ve performed.
Stage 7: Public Company
“Last scene of all…”
People: It’s all about talent at scale. Retention, engagement, and performance systems. Org design now meets shareholder demands. “Say for Pay”. Retention can become an existential crisis.
Systems: Auditable, scalable, secure. Any break breaks trust and breaks share price. 10Qs, 10Ks, SOX, Legal, Public Audits, Quarterly Conference Calls, Security, Privacy… not a lot of room for error.
Exec. & Team Leadership: Focus shifts to investor communication, earnings predictability, and capital allocation. CEO and CFO manage Wall Street as much as they manage their Exec. Team.
Product: Roadmap shaped by public market scrutiny. Product roadmap is a quarterly talking point. Innovation and Margins are constantly trying to be balanced.
GTM (Go To Market): Predictability is the name of the game. DO NOT MISS GUIDANCE! Public metrics dictate what, when, and how you sell. Market expansion and key customer wins and losses get scrutinized by analysts.
Board & Investor Management: Public fiduciary duties. You work for the Board and Wall Street now. Strategic oversight and communications dominate. The job is now all about storytelling, strategy, structure, and execution.
Culture: The public company culture is all about “Integrity Without Compromise”, “Customers Come First”, “Seek the Best”, and “It’s the People”. Your exec actions speak louder than any words here. Every action your leaders take is meticulously watched and stories are told. If you don’t control your own cultural narrative, it’s likely to be created by your large company now on social media.
Final Bow: Play the Right Stage
Don’t use a Stage 5 playbook in Stage 2. Don’t prepare for an IPO when your team hasn’t practiced the equivalent of a quarterly conference call [e.g. QBR (quarterly business review) or “Mock Conference Calls”].
Each stage requires the founder and exec to shift leadership styles, delegation, ownership, and culture. What got you to the current stage is not what’s going to take you to the next stage.
An ounce of prevention is worth a pound of cure. Knowing the next stage is coming and preparing for it is over half the battle. Failing to stay culturally and operationally healthy and/or take your medicine to pay down cultural debt and operational debt will likely cause critical internal issues. Take your medicine and prep for your next stage. Otherwise you will get “sick” in your next stage and require a doctor or a team of doctors to rehabilitate you.
