The one thing no book can teach you is how to chart your own course.
A great company and a great venture investment are not always the same thing.
Where investment frameworks meet the messier realities of people, markets, and competitive advantage.
A reading guide to the practical work of running a company: people, product, sales, and growth.
What the experience of building a company reveals that a polished success story leaves out.
What founders’ lives reveal about judgment, ambition, and the circumstances behind extraordinary companies.
How capital, government, counterculture, and personal ambition helped create Silicon Valley.
If the “right” answer is obvious, what are your references actually telling you?
The person you’re firing isn’t the only one whose judgment deserves scrutiny.
How distribution dependence, fixed commitments, and fear narrowed Teespring’s room to maneuver.
A weekly pause to compare what you meant to do with what you actually did—and notice the gap.
What 127 rejections and a company’s closure taught me about fundability, persistence, and the meaning of failure.
An inside perspective on Forward’s ambition—and the operational and financial realities of reinventing healthcare.
What game designers understand about helping people succeed without telling them every move to make.
Design the conditions that make your goal achievable, even when the process looks unconventional.
Define the outcomes you need before writing the job description or deciding whom to interview.
Before hiring someone to coordinate your executives, ask why your executives need that coordination.
Why the sellers you attract can determine a marketplace’s direction more than the tactics used to acquire buyers.
How to account for seller acquisition costs without losing sight of what each marketplace transaction earns.
Moving beyond your job description to understand what the company actually needs to succeed.
A beautiful model of the company at scale is little help if you ignore what could kill it next month.
When investors ask for network effects, are they describing your business—or repeating what they want to hear?
What customer cohorts can tell you about retention, product-market fit, and whether growth is sustainable.