🧬 From VC to Operator: The Career Move Nobody Recommended | Caleb Appleton (Part 3/4)

In this episode of The Biotech Startups Podcast, we explore Partner at Bison Ventures, Caleb Appleton's journey from venture capital to operations and back again. Caleb shares his experience joining Innovation Endeavors during its spinout from Eric Schmidt's family office, where minimal structure forced him to rapidly master sourcing, diligence, and thesis-building—including a cold email that landed a multibillion-dollar investment in Eikon Therapeutics. Grappling with whether he could truly operate rather than just advise, Caleb left venture in 2020 to join TuneIn during a pandemic crisis, managing a $50 million turnaround after canceled sports leagues devastated subscriptions. He repositioned the company away from unsustainable NFL deals toward ad-supported radio and premium news content, achieving profitability while learning the immediate feedback loops and difficult pivots that operating demands. These hard-won lessons in execution and empathy for founders ultimately led him back to venture, joining Bison Ventures in 2023 as a more complete investor.