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Long-form insights from Guild members.

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Can we please kill the solo founder myth?

You know the story. One person, one garage, one glowing screen. They wrote every line of code, drew every logo, answered every support ticket, and slept on the floor until, one day, they walked out a billionaire. Alone. It’s the most repeated story in all of startup culture, and it’s the one almost nobody stops to check.Well, I’m checking it. And it’s garbage.Here’s what makes this the right moment to say so. The myth just got a new spin. The old version was the lone genius in the garage.… Read more

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Insight Aug 13, 2026

Scale Anxiety

Something that happens a lot in my conversations with early stage founders are questions about what’s going to happen later. “How will we compete with Google?” “What happens if we get to 10,000 users and customer support can’t support them?” “What if the cost of onboarding a new customer is too high?I’d like to say that entrepreneurs are in the imagination business. It’s what we do. We imagine a world that is different than the one around us, and we figure out how to bring that world into being.… Read more

Insight Jul 17, 2026

Stop Looking For a Technical Cofounder

I’ve been the technical cofounder. I’ve been the guy on the other side of the table getting pitched by the less-technical founder. I’ve been the guy who said yes and regretted it, and the guy who said no and watched the venture die anyway, and the guy who said no and watched it succeed without me. Thirty ventures in, I’ve been on every side of this thing there is to be on.… Read more

Insight Jun 5, 2026

The Death of the Product Manager and the Rise of the Build Team

I’ve had a lot of conversations over the past year about jobs in the digital economy.More specifically, I’ve had conversations about the jobs involved in creating software, building products, and growing businesses. And one thing has become increasingly clear: the landscape we’re operating in is shifting beneath our feet.Not gradually. Not predictably.Quickly. Shockingly.… Read more

Insight Apr 18, 2026

The Thing We Forgot

Here’s the deal with capitalism. Somewhere along the way, we forgot what it was actually for.Not the recent interpretation of capitalism, either. Not the one where the M&A crowd assembled thelion’s share of the American economy into a handful of Game of Thrones houses dominated by a handful of ten-figure oligarchs defended by law and custom and societal malaise. Before any of that.… Read more

Insight Mar 27, 2026

The Unicorn Industrial Complex

There is a machine out there. It hums along, invisible to most people who feed it, and it has been running so long that the people inside it have stopped asking what it actually makes.Call it the Unicorn Industrial Complex.… Read more