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 Guest

Tim 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 entrepreneurship
• TA’ing dozens of classes while failing the very course he helped write
• The question his mentor used to determine whether someone is “ready” to start a company
• Starting a company out of necessity—and surviving the emotional and operational chaos that followed
• Recruiting co-founders, navigating breakups, and learning when to let go
• How insecurity and confidence collide in early-stage building

About Round Two

Round Two, hosted by Jaclyn Siu, rewrites the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts.

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