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Bye Stripe, on to the Next Adventure

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I sold my bootstrapped startup to Stripe and I’ve worked for them for a couple of years. It’s an amazing company. I learned a tremendous amount and worked with some amazing people. However, the pull to build something new—especially with the massive improvements in AL/ML—was too strong, and I’ve decided to move on and build another technology company.

I’m going to blog about the lessons I’ve learned from Stripe—both good and bad—in the coming weeks.

I’m looking forward to the constant challenges that building and running a startup brings (including doing this with multiple young kids). Working in BigTech is intellectually stimulating, but does not provide the sort of opportunities for building character and forming the whole person that a startup does (at least, for how I’m wired).

I’ve missed the fear and excitement of doing something unproven that will probably fail. Feeling like a beginner in learning a new discipline or skill. The creativity of figuring out how to solve a problem you didn’t know existed yesterday (or an hour ago). Building a startup doesn’t let any part of you remain stagnant, and I love that experience, even if it’s challenging and at times stressful.

What’s next?

I don’t know exactly. I’ve found a co-founder that I’m thrilled to partner with. We know we want to build a B2B SaaS product in a large market. My co-founder has been doing deep AI/ML work for the last decade, so we want leverage his experience to create a 10x improvement in a key workflow to gain a foothold in whatever space we decide to tackle.

Our thesis is that there will be few "AI/ML companies". In most cases, AI/ML will be sprinkled in across a traditional SaaS stack (you can see this happening now).

However, we think that building a company from the ground up using AI-enabled tools will enable you to build companies in an entirely new way. Instagram had 13 people and sold for $1B; Warp had ~70 people and reached a 1.7B valuation. And this was done without AI-enabled tools powering the internal aspects of the business.

What could be accomplished if you build the entire business operations with AI in mind?

GitHub Copilot + ChatGPT has increased my productivity massively; we want to see how much we can do with a small navy-seal-like team coupled with AI tooling.

No idea

… but we don’t have an idea yet. We are 100% in the idea-hunting mode: if you have an interesting product idea, or some workflow you hate and can’t believe no one has fixed yet, we’d love to chat.

Reach out at