How Did You Learn That?
Mastery Is a Team Sport (It Always Has Been)
“How Did You Learn That?”
I’ve been thinking a lot about this question lately. I just did a live Q&A on the subject yesterday (Wed, Jan 28 2026). We are doing these live sessions monthly now. Look for them in your future feeds.
I don’t think a lot of people stop and ask, “How Did I Learn That?” It’s a valuable question to reflect on as part of my Learn It, Do It, Coach It framework.
When you unwind the tape on your own personal life, your career, or the careers of history’s most iconic founders, clear “learning patterns” emerge:
The best learning is never solo. It’s social. It’s communal. It’s collective intelligence.
Solo learning is valuable as well but it’s more about personal reading, research, and gritty figuring it out. Being inside your own head.
The real powerful learning happens, however, when you are surrounded by really smart people with diverse viewpoints all focused on solving a common problem.
Small teams/groups of these people provide extremely powerful collective learning. These people are typically formed from your mentors, your colleagues, and your networked communities.
Making sure you spend time with all three segments of “learning potential energy” is critical time to carve out of your regular calendar. As they say, “All work and no pontification makes Jack a dull boy!” (Or something like that 😉)
Mastery Has Always Followed the Same Arc:
Apprentice → Journeyman → Expert → Master
If you strip away the modern labels and look across history, learning in every domain has typically followed the same structure:
Apprentice: You watch others.
Michelangelo apprenticed under Ghirlandaio.
Every Renaissance workshop functioned as a collective learning engine.Or Medical school students in year 2.
Journeyman: You do the work alongside the experts.
Blacksmiths, carpenters, and stone masons all traveled town to town to work together on real problems.Expert: Once you’ve “journeyed” enough, you begin to contribute your own ideas and people begin to view you as an expert in your craft.
Experts continually learn through exchanges and critiques with other experts.Master: Here you become a master by teaching others your expertise. You give back to your community that taught you.
Mastery of anything has always followed this arc. The lone genius concept is rare and the probability of anyone becoming a lone genius is not advised.
Behind every “genius” is a collective network of intelligent peers.
Silicon Valley Example #1: Jobs & Wozniak
The myth: Steve Jobs was a lone visionary.
The reality: Apple was born out of collective intelligence.
Jobs learned product taste from California counterculture and Xerox PARC.
Woz learned electronics from the Homebrew Computer Club - one of the greatest communities of peer learning in tech history.
Neither would have built Apple alone.
Their genius was in the collision of perspectives from design to engineering, to culture, to collective networks, to storytelling the “why” of the design.
Silicon Valley Example #2: Andy Grove’s “Managerial Leverage”
Andy Grove (ex-CEO Intel) didn’t invent modern Silicon Valley-style management in isolation.
He synthesized it from:
Observing Bill Hewlett and David Packard
Learning from Intel’s earliest manufacturing leaders
Absorbing lessons from mentors and peers during Intel’s turbulent early years
“As a middle manager, you are in effect a chief executive of an organization yourself… As a micro CEO, you can improve your own and your group’s performance and productivity, whether or not the rest of the company follows suit.”
It turns out that the one-on-one is not only a fundamental element in the manager/employee relationship, but perhaps the best source for organizational knowledge that a manager can get. In my experience, managers who don’t have one-on-ones understand very little about what’s happening in their organizations.
The best operators are aggregators of wisdom and share it broadly 1:1 and with their small teams.
Silicon Valley Example #3: The PayPal Mafia
People talk about the PayPal Mafia like some magical convergence of future founders and investors.
But what made them powerful wasn’t individual brilliance, it was collective apprenticeship.
Together they:
Debated ideas
Critiqued each other
Shared failures
Swapped frameworks
Built confidence loops
Reid Hoffman has repeatedly said the greatest accelerant in his career was learning directly from Peter Thiel, Max Levchin, and Elon Musk in deeply intellectual, sometimes uncomfortable, conversations.
The community was the curriculum.
Silicon Valley Example #4: Netflix in the Early Days
My story. People assume Netflix succeeded because of superior software or logistics.
Not even close to the truth. We didn’t have superior anything. But we were some of the best collective learners and translated this learning into DVD community intelligence and product delivery.
We had postal engineers, mathematicians, supply chain veterans, filmmakers, and technologists all exchanging perspectives of how best to deliver entertainment to people’s living rooms.
Our breakthrough in the Disc Inventory Management System wasn’t the product of one person. It was the outcome of dozens of conversations, debates, whiteboard sessions, and shared learning loops.
Our recommendation engine? Same story.
Built not by a solo genius but by “the guild”. We were the modern workshop of experts learning from each other and focused on delivering a great product to our customers.
Collective intelligence was our moat.
Silicon Valley Example #5: OpenAI and the “Lab Model”
OpenAI’s, and now others like Anthropic and even Gemini, breakthroughs didn’t come from isolated research.
They came from:
Open collaboration
Cross-disciplinary teams
Shared insights
Collective problem solving
Iteration in public view
The entire AI ecosystem today is built on shared research, shared models, and shared lessons, just like the old European guild system.
The future of learning loops back to the past:
Communities learning together.
So back to my main point and my original question:
How Did You Ever Learn Anything?
Your own path probably mirrors the same historical patterns
Think about the best things you know:
A financial system
A negotiation tactic
A forecasting model
A pattern for managing risk
A way to coach or build teams
A way to read a room
A way to influence a CEO or board
It’s almost always:
Someone showed you
Someone challenged you
Someone told you a story
Someone pushed you to think differently
Someone asked a question you didn’t know the answer to
You learned by being in conversation with smart people and talking and listening and observing a lot.
The Two Hardest (And Most Powerful) Phrases to Achieve Mastery
If mastery and collective intelligence are the goal, there are 2 phrases that will help get you there faster. Usually, they are the hardest phrases to say out loud.
1. “I Don’t Know.”
Michelangelo/Einstein/Grove/Bezos/Buffet/every great Master said it during their own learning.
Other “leaders” (I won’t name names) - never say the words “I Don’t Know”… they try to fake it until they make it.
Great leaders aren’t afraid of not knowing.
They are afraid of not learning something new.
2. “Can You Help Me?”
This is the call that activates your network.
It is the fastest path to someone else’s 20 years of expertise.
Bill Campbell, the Trillion Dollar Coach, lived by this simple humility to ask people:
“What do you think?”
He learned from them.
They learned from him.
So If Mastery Comes From a Community, Then Build/Invest In Your Community
Every CFO, COO, founder, or operator I’ve coached who accelerated most quickly shared one habit:
They talked to more people, about more things, more often.
They said “I Don’t Know” and “Can You Help”… A LOT!
They intentionally constructed what I call a Personal Knowledge Network - a modern version of the medieval workshop or learning lab.
Mentors
Peers
Cross-functional partners
Experts outside their domain
People 10 years ahead
People 10 years behind
People who think differently
People who ask harder questions than they do
This is how you compress decades of learning into months.
Because you’re not learning alone.
You’re learning through and with others.
Just like every master has always done.
Oh yeah, one last thing. Once you become a Master you must Pay It Forward. Find an Apprentice and keep the loop alive!
Footnotes - More reading on Andy Grove: one of my Best Ofs.
