All essays
The complete archive, newest first.
The one thing no book can teach you is how to chart your own course.
July 16, 2026
A great company and a great venture investment are not always the same thing.
July 7, 2026 · Full series
How awareness of your own stories, fears, and attachments changes the way you live and work.
June 29, 2026 · Full series
Science fiction as a way to stretch your imagination about what the future could become.
March 30, 2026 · Full series
Where investment frameworks meet the messier realities of people, markets, and competitive advantage.
March 16, 2026 · Full series
A reading guide to the practical work of running a company: people, product, sales, and growth.
February 2, 2026 · Full series
Eight books on power, technology, human possibility, and absurdity—and what I learned by leaving more room for silence.
January 29, 2026
What the experience of building a company reveals that a polished success story leaves out.
October 27, 2025 · Full series
What founders’ lives reveal about judgment, ambition, and the circumstances behind extraordinary companies.
October 21, 2025 · Full series
Turning forty, questioning inherited milestones, and wondering why success has to feel so hard.
October 14, 2025
How capital, government, counterculture, and personal ambition helped create Silicon Valley.
September 29, 2025 · Full series
Before choosing investments, examine how you think: bias, probability, persuasion, and the limits of your own models.
September 22, 2025 · Full series
A self-directed curriculum for understanding the ideas, people, and businesses behind venture capital.
September 18, 2025 · Full series
Your tools are getting more powerful. What if the real constraint is the programming you don’t know you’re running?
June 30, 2025
The choices shaping your life include the ones you don’t realize you’re making.
June 17, 2025
If the “right” answer is obvious, what are your references actually telling you?
June 10, 2025
The perspective you would offer someone else in a crisis may be the one you need yourself.
June 5, 2025
What looks like failure depends on where you end the story.
April 7, 2025
Are you choosing a partner who fits your values—or one who reassures you about who you are?
March 25, 2025
The person you’re firing isn’t the only one whose judgment deserves scrutiny.
February 13, 2025
Six books that changed how I think about power, leadership, food, masculinity, and holding ourselves back.
January 23, 2025
The products, habits, and changes in perspective that meaningfully improved my life in 2024.
January 21, 2025
How distribution dependence, fixed commitments, and fear narrowed Teespring’s room to maneuver.
January 6, 2025
Start with how you want life to feel, then leave room to change how you get there.
January 3, 2025
A weekly pause to compare what you meant to do with what you actually did—and notice the gap.
December 23, 2024
What riding in a Waymo made me reconsider about the cars, streets, and rules we take for granted.
December 22, 2024
What 127 rejections and a company’s closure taught me about fundability, persistence, and the meaning of failure.
November 25, 2024
An inside perspective on Forward’s ambition—and the operational and financial realities of reinventing healthcare.
November 14, 2024
What ten days of meditation revealed about anxiety, attention, and the limits of thinking your way to understanding.
October 15, 2024
When the desire to be wanted masquerades as care for someone else.
August 14, 2024
What building a nutrition company changed about my understanding of food, health, and what actually deserves our attention.
August 2, 2024
What moving to Miami and back taught me about the difference between an appealing destination and a life that fits.
July 15, 2024
An experiment in publishing unfinished thinking instead of letting perfectionism keep it in drafts.
July 10, 2024
What paying attention during a squat can teach you about working with your body instead of imposing a plan on it.
March 2, 2024
What our reactions to gym selfies reveal about vulnerability, judgment, and our own insecurities.
February 4, 2024
Why insight is not the same as lasting change—and other misconceptions about psychedelic therapy.
July 12, 2023
After comparing 163 protein powders, which differences deserve your attention—and which probably don’t?
June 6, 2023
What calorie and macronutrient totals leave out about the food you actually eat.
April 25, 2023
Loving a place, outgrowing a chapter, and letting go of the identity attached to it.
November 23, 2022
What game designers understand about helping people succeed without telling them every move to make.
October 30, 2022
Design the conditions that make your goal achievable, even when the process looks unconventional.
June 1, 2022
Define the outcomes you need before writing the job description or deciding whom to interview.
May 25, 2022
How speculative demand for tokens can obscure whether anyone actually wants the underlying product.
May 12, 2022
Five intentions for 2022: making room for creation, connection, and letting go.
January 3, 2022
The changes that most improved my everyday life in 2021, from practical conveniences to personal growth.
January 2, 2022
Before hiring someone to coordinate your executives, ask why your executives need that coordination.
September 6, 2021
An unlikely outcome does not make a probabilistic forecast wrong.
December 5, 2016
Early impressions of virtual reality: the promise of presence and the friction between a compelling demo and everyday use.
July 20, 2016
A 2016 look at how Tesla’s software and sales model could change the economics of owning a car.
April 15, 2016
Why the sellers you attract can determine a marketplace’s direction more than the tactics used to acquire buyers.
March 9, 2016
When the activities that fill your day crowd out the ones that make your life feel worthwhile.
December 29, 2015
How to account for seller acquisition costs without losing sight of what each marketplace transaction earns.
October 23, 2015
Why music streaming’s economics depend on the bargaining power of labels, artists, and distributors.
May 27, 2015
Moving beyond your job description to understand what the company actually needs to succeed.
May 4, 2015
A beautiful model of the company at scale is little help if you ignore what could kill it next month.
April 15, 2015
When investors ask for network effects, are they describing your business—or repeating what they want to hear?
July 24, 2014
What customer cohorts can tell you about retention, product-market fit, and whether growth is sustainable.
June 17, 2014
What Facebook’s purchase of Oculus suggested about technology companies competing for control of our attention.
March 28, 2014