The Truth About Tech Exits No One Talks About | with David Siegel (Audio)

Is tech really the fast track to wealth — or just a story we tell ourselves? In this episode of Resilient Riches, Yair Klyman sits down with David Siegel, former CEO / President of Meetup, Investopedia, and Seeking Alpha, for an honest, no-fantasy conversation about what building wealth in tech actually looks like. David has led multiple high-growth tech companies, experienced two exits, and made some very real (and costly) mistakes along the way. In this conversation, he breaks down the myths most people believe about tech success — and what he wishes more founders, operators, and professionals understood before chasing the next big opportunity. We cover: Why a huge exit doesn't necessarily mean personal wealth The hidden danger of raising too much capital too early Salary vs. equity — and how to think about the tradeoffs at different life stages How dilution quietly erodes ownership over time What really drives strong acquisition outcomes (hint: it starts years earlier) Why many people feel lost after an exit — and how to avoid that trap How to build wealth without burning out your health, family, or identity This episode isn't about hype, hustle culture, or startup mythology. It's about structure, timing, ownership, values — and making decisions you can live with long after the headlines fade. If you're in tech, thinking about getting into tech, or trying to understand how wealth, work, and life actually fit together, this conversation will give you clarity most people don't talk about publicly. 🎧 New episode of Resilient Riches — out now.