On this episode of The Risky Business Podcast, Sam Stone interviews serial entrepreneur and investor Todd Earwood, a man who treats business like a sport—testing over 150 ideas, launching 18 companies, and selling three, including a major exit in 2023. From founding a web video company before YouTube to co-launching a VC fund with over 100 AI investments, Todd shares the bold bets, brutal lessons, and surprising wins from a life spent chasing innovation. He opens up about the time he nearly lost his house while self-funding a startup—only to secure millions in investment just 12 days after receiving a foreclosure letter. This episode is packed with real talk about risk, resilience, and the relentless pursuit of building something meaningful.