Epsilon Theory Podcast The Intentional Investor #35: Devin Anderson
Aug 20, 2025
Devin Anderson, CEO and co-founder of Convexitas, shares his extensive experience in startups and financial institutions. He recounts his early tech career in high school and pivotal lessons from the 2008 financial crisis. The discussion dives into the complexities of risk management, the challenges of creating a business during the pandemic, and the transformation of banking models. From light-hearted anecdotes to deep financial insights, Anderson emphasizes the importance of innovation in navigating today's investment landscape.
AI Snips
Chapters
Transcript
Episode notes
Early Internet Startup Recruit
- Devin Anderson fixed a computer lab issue in high school and was recruited by a local dial-up internet startup, Stargate.
- He worked there through the dot-com era, then to Lycos, gaining deep early-web operational experience.
Stargate Bankruptcy And Timesheet Scandal
- Stargate bought a software firm that had timesheet fraud and then faced collapsing revenue as the dot-com bubble burst.
- The company negotiated forbearances, entered bankruptcy, and its assets were sold in pieces — a hard lesson on leverage.
Default Timing Matters
- If you're borrowing from banks, be the first to default, not the last, to preserve negotiating leverage.
- Waiting to negotiate until you're the last asset leaves banks eager to seize assets, destroying equity value.