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Founder Breakups Are Real. So Why Don’t We Plan for Them?*

Everyone reading this knows someone whose marriage ended. Those endings aren’t always kind. And when things turn adversarial,... 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

What the Fuck Does It Mean to Have an AI Strategy?*

Unless you’ve been dodging your board entirely, they’ve already asked you, “What’s your AI strategy?” And they’re not... Read more

Manifesto: Power Law Is for VCs, Not Founders

Founders are inventors. They create extraordinary things — products that captivate us, entertain us, enrich us, transport us, and even... Read more

“Founder Mode” Is a Dangerous Red Herring

Love the conversation. Disagree with the implied conclusion. I won’t summarize Paul Graham’s essay on founder vs. manager... Read more

R.O.S. Return on Safety

When do employees share opinions freely? When do they call attention to system frailties? When do they jump... Read more

You Might Want to Sit This One Out

In 2022, a massive correction began in the startup ecosystem. Rising interest rates led to plummeting startup valuations... Read more

How to Raise Early-Stage Capital in Any Market

Raising early-stage capital is easy, right? It must be. It seems virtually every other tech-related article to grace my screen... Read more

Management Debt Series: Learn How To Deliver Feedback

It's been said time and again that people don't quit jobs; they quit managers. And why do they... Read more

From Founder / CEO Client To General Partner, Why I’m Joining Enjoy The Work

In early 2017, I was feeling pretty on top of the world. I had left my role as... Read more

Management Debt Series: Learn How To Run a @#$#@ Meeting

There are two separate paths to startup success. The first and far more celebrated path is the one... Read more

Does Everyone Know What We’re Supposed To Do Next? An Introduction To Internal Communications For Startup Founders.

When you start a company, your job is to sell a vision. Then you have to go build... Read more