Old Problem or New Problem?
When to Listen to Others, and When to Listen to Yourself You’re a first-time founder. Whatever face you... Read more
Tolerate vs Celebrate
Cultural Decay Takes Root in One Excuse Culture is more about what you tolerate than what you celebrate.... Read more
You’re Not Telepathic
It’s remarkable how many of my founders believe in telepathy. They assume truncated messages in Slack and offhand... Read more
What Has To Be True?
The Best Founders Don’t Move Forward. They Work Backward. Most founders put one foot in front of the... Read more
The AI CEO: Two Tensions
The same conversation keeps finding me — in Nashville, Ottawa, Glasgow, Lisbon, and most recently, at SXSW in Austin. “How... Read more
Bad Actors Look Like Good Actors Until They Don’t
If you work long enough, date enough people, have enough friends, live long enough, you learn an uncomfortable... Read more
Building Great Engineering Teams on a Startup Budget (5-10 people)
I was at a gathering of CTOs last week, talking about the antipatterns that make a brittle engineering... Read more
Landing the Plane
You’re a founder. The company you’ve built with love and sleepless nights , the dream that eclipsed relationships, family,... Read more
Is the Founder Coachable?
More startups die from suicide than homicide… We work with a great number of venture capital firms. Successful... Read more
Founders: Don’t Get Fired
One of the quiet heartbreaks of startup life is when a founder is fired from their own company.... Read more
Waiting Is Not Leading
A startup CEO sits in a particularly passionate leadership team meeting. The debate is heated but respectful. Two... Read more
Instant Code ≠ Instant Company: How Established Startups Can Compete in the AI Era
Imagine the scene: a solo founder, perhaps fueled by caffeine, dictates ideas to an advanced AI. Code materializes... Read more
User Manual
It was 2021. One of my CEOs pinged me with a request. He asked if I would get... Read more
Who Has a Voice, and Who Has a Vote?
In the early days of startup life, decision-making tends to feel straightforward. That might seem counterintuitive — after all, the... Read more
Are You a Prosecutor or a Problem-Solver?
The Power of a Good Question “He who asks a question is a fool for five minutes; he... Read more