Jason Cohen Built Two Unicorns. Here’s The Only AI Startup He’d Build in 2026

This post is auto-generated from a public YouTube interview for personal study notes. It is not an endorsement. The transcript is machine-derived and may contain errors; refer to the original video for accuracy.

About this video

AI is everywhere. Every pitch deck has it. Every budget mentions it. But if you were starting a company today, what would you actually build?

Jason Cohen has built two billion-dollar companies — WP Engine and Smart Bear. I asked him how he’d approach AI in 2026 if he were starting from scratch.

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About Me: I’m Rob Walling. I’ve been building, growing, and acquiring SaaS companies for nearly two decades.

I’ve started six companies (five of them bootstrapped) and exited multiple times, most notably selling Drip in 2016.

I’ve invested in over 200 startups, and my focus is on helping founders build multimillion-dollar companies without the pressure of the traditional "unicorn or bust" venture capital model.

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