Four startups. All four exited. Combined enterprise value north of $100 million.
I could stop there and let it sound clean. It was not clean.
That number hides the starts and stops, the pivots that did not work, and the ideas that never became more than an idea. It also hides a few that are still just an LLC and a website.
AI has made those first steps almost too easy, and if I am being honest, many of mine are sitting right there, waiting on me.
The number itself feels big to me. It is also small, even tiny, next to what some of my mentors and partners have built. So here is what I actually think it means.
Across all of it, the wins and the false starts both, the throughline was never the outcome. It was the people. And the journey, the effort, and the willingness to fail.
Authentic, trustworthy, reliable leaders who cared more about the customer and the team than about reaching an exit. Leaders who leaned on a network that did not look like a cap table. Investors, yes. But also peers, mentors, vendors, customers, and family.
In my experience, the outcome tends to follow when you get that part right. Not always. The 50+ unused domains and dozens of LLCs doing nothing remind me of that. But often enough that I have stopped calling it luck.
So here is the Chip Chat, said plainly:
Be real. Treat people well. The ride is the part you actually get to keep.