In this podcast episode, three-time founder and startup advocate Jaclyn Siu sits down with Tim He, a founder whose journey defies every expectation and embraces every contradiction.Tim went from failing the same entrepreneurship class he helped write, to TA’ing 30+ courses, to starting a company mostly because he couldn’t get a traditional job. His story blends humor, humility, and hard-won lessons about identity, readiness, co-founder dynamics, and building before you believe you're qualified.About Our GuestTim He is a founder and longtime TA of his university’s entrepreneurship program, where he helped design midterms, shape curriculum, and teach hundreds of students—despite never being admitted to the business school himself. Tim later founded his first company while still in college, navigating co-founder selection, team dynamics, early traction, burnout, and the emotional cost of choosing friendship over a company.In this episode, we cover:How a chance encounter at a mall job led Tim into entrepreneurshipTA’ing dozens of classes while failing the very course he helped writeThe question his mentor used to determine whether someone is “ready” to start a companyStarting a company out of necessity—and surviving the emotional and operational chaos that followedRecruiting co-founders, navigating breakups, and learning when to let goHow insecurity and confidence collide in early-stage buildingListen now to hear a founder story shaped by contradictions, hard pivots, and the kind of lessons you can only learn by doing.About Round TwoRound Two, hosted by Jaclyn Siu, rewrites the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts.Looking for guidance during your own transition?Starcycle supports founders in closing chapters and opening new ones—with empathy and clarity. Starting at $299. Tailored to your needs. No hidden fees.Get started today at starcycle.ai

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