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"If you're making a good decision, it will usually feel liberating; if you're making a bad decision, it will usually feel constraining."

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.

Key topics covered:

• Innovation Endeavors Spinout: Joining during the transition from Eric Schmidt's family office and thriving without structured investment processes
• Operator vs. Advisor Identity: Wrestling with self-doubt about execution ability and deciding to leave venture for operational experience
• TuneIn Pandemic Turnaround: Managing a $50M business crisis when COVID-19 canceled sports leagues that drove subscriptions
• Strategic Repositioning: Eliminating unsustainable NFL deals and doubling down on ad-supported radio and premium news content for profitability
• Return to Venture Capital: Joining Bison Ventures with newfound operator empathy and understanding of execution challenges

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Subscribe to the Podcast:Apple: https://podcasts.apple.com/us/podcast/the-biotech-startups-podcast/id1679591994Spotify: https://open.spotify.com/show/2PSL162R2s0zOwU5913Zv4Youtube: https://www.youtube.com/@thebiotechstartupspodcast Website: https://www.thebiotechstartupspodcast.com/ 
Find our guest, Caleb Appleton at these links: LinkedIn: https://www.linkedin.com/in/caleb-appleton-86563484/Website: https://www.bison.vc/ Find our host, Jon Chee, at these links: LinkedIn: https://www.linkedin.com/in/jonchee
Learn more about Excedr:LinkedIn: https://www.linkedin.com/company/excedr/ Website: https://www.excedr.com
Intro & Outro Songs Created by OkKyojin, Owned by Excedr:Website: https://flow.page/kyojin 
Resources & Articles:Innovation Endeavors and the Super Evolution Thesis: https://www.innovationendeavors.com/aboutImpact of COVID-19 on Sports Broadcasting: https://en.wikipedia.org/wiki/Impact_of_the_COVID-19_pandemic_on_American_sports_broadcastingVenture Capital Careers: Work, Salary, and Exit Opportunities: https://mergersandinquisitions.com/venture-capital-careers/​Companies, Universities, & People mentioned:Innovation Endeavors: https://www.innovationendeavors.comBain & Company: https://www.bain.comVicarious Surgical: https://www.vicarioussurgical.comEikon Therapeutics: https://www.eikontherapeutics.com Bison Ventures: https://www.bison.vc Sequoia Capital: https://www.sequoiacap.com 
Eric Schmidt: https://www.linkedin.com/in/eric-e-schmidtDror Berman: https://www.vcsheet.com/who/dror-berman
Timestamps: 00:00 Intro02:06 Joining Innovation Endeavors and early venture lessons05:29 Navigating a fund spinout and defining the "Super Evolution" thesis07:10 Baptism by fire: scope, imposter syndrome, and advice for getting into venture10:11 First investments: Vicarious Surgical and a cold email into Eikon Therapeutics10:43 Leaving venture to test himself as an operator and applying to Stanford GSB in 202013:01 Walking away at the term sheet stage from his own startup idea15:50 Understanding TuneIn's business model and the impact of canceled sports20:15 Rethinking strategy: from "NFL cocaine" to sustainable, news‑driven subscriptions25:09 Hard pivots, breaking inertia, and identity attachment in entrepreneurship27:23 Returning to venture and joining Bison Ventures29:48 OutroThe Biotech Startups Podcast gives you a front-row seat to the business and science of building a biotech. Hosted by Jon Chee, CEO of Excedr, the show features honest conversations with founders, execs, and investors about their work, their companies, and how they got there. From scientific breakthroughs to startup lessons, each episode explores what it really takes to grow a life science company—from pre-seed to IPO.