Jameson CampAdvising on AI and GTM | 2x Exits

You’re not alone #entrepreneur

23 Oct 2025 · 1 min

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An entrepreneur who sold two companies for $30 million feels like a failure because the acquirers shut them down. Google and OpenAI advances killed the long-tail keyword search model his businesses relied on. He's reframing success as consistent cash flow instead of net worth, and says he's rebuilding alongside anyone else starting from scratch.

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I sold 2 companies for a little over $30 million, sold millions of dollars of workshops and courses, and I still totally feel like a failure all the time. Let me explain why. Okay, so first off, both the businesses I sold are now out of business, right? The acquirers drove them into the ground. Then I watched Google and OpenAI destroy Google Search and long-tail keyword search, which was a huge piece of what I did for a long time. I've been frozen because I feel like every business model that I want to build is going to get eaten by AI super quickly. What I've realized is that feeling rich and feeling successful isn't about net worth as much as it's about sort of the cash flow that's coming in. But I'm still here showing up every day, working on content, working on new businesses, trying new things, going to the gym, even though I've got this complex tear in my meniscus. It's been a ride. So if you're rebuilding or you're building from the beginning, I'm right here with you.