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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

“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

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

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

Management Debt – The Perilous Cost Of Not Knowing How To Run A Larger Org

I have a neighbor. Name is George. Marine veteran. Early 70s. Built like a mountain carved down into... Read more

Time To Armor Up — A New Era Of Fundraising Is Upon Us

We guide a lot of fundraises. And we see them across a wide spread of geographies, domains, and... Read more

All-In or All-Out

Let me know if this scenario sounds familiar. You’ve hired someone, ramped them, and set them loose. While... Read more

Working With Vs. Working For — A Musing on How Language Shapes a Company’s Culture

To “work with” or to “work for”? That is the question. Or at least, it’s the question I’ve... Read more

Do → Manage → Coach

In the early startup days, life is a blur. You’re involved in everything. You’re doing everything. You’re building... Read more

Return vs. Remote

There are party lines being drawn. Each side is fiercely self-righteous. Their arguments are persuasive and well-considered. The... Read more

Good vs. Bad Board Members

And How to Vet Them Appropriately A productive board of directors is a beautiful thing. It’s an accelerant.... Read more