Surviving Vulture Capitalists, Dot-Com Crashes, and the AI Shift w/ David S. Rose

For today's episode, I sit down with David S. Rose, legendary angel investor and founder of Gust, to hear how he's built, lost, and rebuilt companies across five decades of tech.

We cover the moment a vulture VC tried to blackmail him during a down round, and why he refused to fold. David walks through how he called their bluff, filed Chapter 11, and came out owning the company.

Then we dive into his dot-com rise and crash: patents valued at $100M, a $50M investment consortium, offices in Europe, an acquisition of a Branson company. Two weeks before closing, it all fell apart.

David shares his father's "alligator trap" wisdom about knowing when to let go, and breaks down the investing framework he's used across 100+ angel investments. If you've ever wondered what separates founders who survive from those who don't, this is the conversation.