- 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.
1h 33m - Feb 26, 2026 - Inside the 7-Year Deal That Built Nolita w/ Eric Hadar
For today's episode, I sit down with Eric Hadar, CEO of Allied Partners, to hear how he built one of New York's most formidable real estate empires.
We cover his $700M acquisition of Citigroup Tower and what that deal taught him about how institutions really think. Eric breaks down why Wall Street's misaligned incentives can actually create rare windows of opportunity for long-term builders willing to be patient.
Then we dive into the seven-year saga of 285 Lafayette, the project where Eric literally coined the term "Nolita" and came within one week of losing everything. He walks through the near-death moments of that deal and how he managed to pull it back from the edge.
If you've ever felt like you're one bad month away from failure, this conversation is a powerful reminder that luck has a way of finding the people who refuse to leave the arena. Eric is living proof.
1h 29m - Jan 8, 2026
