The Inner Game of Entrepreneurship
Here are my favorite passages of 2025 (Part 1)
đ Happy holidays! Consider gifting Tao of Founders to an entrepreneur you love â¤ď¸
On Failure & Resilience
The Stockdale Paradox: holding high and low expectations simultaneously.
Soldier James Stockdale observed that the most optimistic prisoners often fared the worst. Outstanding founders believe their success is inevitable, while expectingâeven relishingâfailures along the way.
âFailure is not something that happens at one point in time. Failure is a door. To me failing feels like stepping out of a room, and into a new one. There is continuity with failure; the end of something always means the start of something else.â
Anything worth doing requires doing things wrong first to learn to do them correctly eventually.
âJust because something doesnât do what you planned it to do doesnât mean itâs useless.â
Post-it notes, microwaves, Viagra, Play-Dohâmany modern inventions were initially intended to solve another problem. Edison was keen to challenge his own flawed assumptions.
You overestimate how bad failure will feel and how long it will hurt.
People systematically overestimate the intensity and duration of negative emotions from bad outcomes. Founders who understand this can take bigger risks knowing recovery is faster than anticipated.
On Identity & Purpose
âI am also all of what Iâve lost.â
Paul Van Doren reflected on outliving his wife, friends, and business partners. Your success wonât shield you from loss. What remains isnât just what you builtâbut who you became in the process.
âImagine you are building a Jenga tower: the higher you stack expectations, the more unstable your identity becomes as a whole.â
The higher the expectations you place on yourself, the harder it becomes to experience satisfaction in who you are at this moment.
âNo dream is as great as the person you might become by remaining true to it.â
The best goals center on becoming, not doing or having. The most rewarding aspects of reaching your goal lie in your chance at improving, each step of the way.
âHow you climb a mountain is more important than reaching the top.â
â Yvon Chouinard
This philosophy shaped Patagoniaâs most consequential decisions, from choosing ethical manufacturing partners to rejecting shortcuts that boost short-term profits.
â Read more
love this one: "âFailure is not something that happens at one point in time. Failure is a door. To me failing feels like stepping out of a room, and into a new one. There is continuity with failure; the end of something always means the start of something else.â"