What Entrepreneurs Can Learn from Make It Stick
You are constantly teaching yourself things that didn't exist as a job description a year ago: how to read a cap table, how to run a board meeting, how to pitch a category nobody has named yet. Under deadline pressure, the fastest-feeling way to learn any of this is to read the guide twice, watch the webinar again, or skim the same term sheet template until it looks familiar. That familiarity is exactly the trap. It feels like competence because the material has become easy to recognize, but recognizing something and being able to produce it under pressure — in a live negotiation, in front of an investor who just asked a hard question — are different skills, and the easy path only builds the first one.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
0 of 5 selected
The core lessons, applied to you
Recognize the founder's fluency trap
Reading a great article on pricing strategy and nodding along feels like learning pricing. It usually isn't. The fluency illusion is especially dangerous for founders because so much of the input you consume — podcasts, threads, books — is designed to feel immediately clarifying, and that ease has nothing to do with whether you could apply it tomorrow.
A founder preparing for a board meeting reads through last quarter's deck twice the night before, feeling sharper with each pass, then freezes when a board member asks an unscripted question about churn that the deck doesn't directly answer.
Before your next board meeting, close the deck and write out, from memory, the three toughest questions a board member could ask and your answer to each — then check your work against the deck.
Quiz yourself before you check the playbook
Instead of rereading a framework, try to reconstruct it cold and see where it breaks. The gap you find — the part you couldn't recall or apply — is far more valuable than another pass through material you already half-know, because that gap is exactly where the real work is.
A founder about to run their first pricing negotiation rereads a negotiation article twice on the way to the meeting, feels prepared, and then goes blank the moment the buyer pushes back with an objection the article never mentioned.
Before a high-stakes conversation this week, write down from memory the three likely objections and your responses, without looking anything up first.
Space out your learning and mix your problems
Cramming a skill right before you need it — negotiation tactics the morning of a big call, financial modeling the night before a raise — produces a shaky version of that skill that often collapses under real pressure. Skills stick better when you practice them repeatedly over weeks, and when you deliberately mix different kinds of problems — a pricing decision, then a hiring decision, then a churn conversation — rather than mastering one in isolation before touching the next.
A founder spends one intense weekend memorizing investor Q&A before a raise, aces the first pitch on adrenaline, and finds the same answers gone two weeks later at the follow-up meeting.
Instead of one prep session, schedule three short practice sessions spread across the two weeks before your next big pitch or negotiation, mixing in different question types each time.
Connect it to what you already know
The strategies above matter most when you actively link new business knowledge to what you've already lived through — a failed hire last year, a pricing mistake from your last company — rather than treating each new lesson as if it arrived in a vacuum. When a decision goes wrong, treat it as data about a gap in your model, not as proof you're not cut out for this.
Testing yourself before a pitch and spacing that practice over two weeks can conflict with the founder's instinct to keep refining the deck itself right up until the meeting. A practical split: spend early sessions on recall and mixed practice, and save deck polish for the final day, so the skill is solid before the slides are.
Name one thing, honestly
Which recent business skill did you assume you'd learned because the material felt familiar, and how would you find out if you're wrong?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
0 of 3 selected
Run this for seven days
Instead of one prep session, schedule three short practice sessions spread across the two weeks before your next big pitch or negotiation, mixing in different question types each time.