Round Two

Join Jaclyn Siu, 3x founder and advocate for embracing entrepreneurship’s toughest moments, for honest conversations about failing forward. Each episode pulls back the curtain on startup life—the good, the gut-wrenching, and the unspoken—to help founders everywhere reclaim their stories, reinvent their identities, and rediscover their power.

Round Two is a business podcast hosted by Jaclyn Siu, with 10 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Jaclyn Siu hosts Round Two, a business show with 10 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #3

  Killing What You Built to Save It

  May 4, 202648 minS2

  <p>In this episode, three-time founder and startup advocate Jaclyn Siu sits down with Andrew Bennett, a self-described "person number six" at Provide, now Head of Small Business at Fifth Third Bank. The conversation covers betting on your best friends, knowing when to blow up what you've built, and what actually makes an exit work.</p><p>Andrew's path to fintech ran through minor league baseball diamonds and college dugouts. He spent most of his twenties coaching before packing his life into two suitcases and flying one-way to San Francisco to join two childhood friends building a small business lending...

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  Episode #2

  Teaching Class With Zero Qualifications

  Dec 17, 202543 minS2

  <p>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.</p><p>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.</p><p>About Our Guest</p><p>Tim He is a founder and longtime TA of his university’s entrepreneurship program, where he hel...

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  Episode #1

  The Phone Call That Ended My Startup

  Dec 3, 202555 minS2

  <p>Two shutdowns. Two completely different emotional realities. One founder who lived both.</p><p>In this episode of Round Two, host Jaclyn Siu sits down with Helena Fogarty — co-founder of Backable and host of Inside the Round — to talk about the moments that force founders to confront the truth: sometimes the math or the market doesn’t give you a choice.</p><p>Helena shares the inside story of:</p>The last-minute reversal from her lead angel investorCalling her co-founder to say “We’re done”Taking over as CEO of a CPG brand already in freefallHow a rebrand destroyed a $2M grocer...

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  Episode #6

  The Things Founders Don’t Say Out Loud: A Bonus Round Two Talk

  Nov 20, 202511 minS1

  <p>Before Season Two of Round Two begins, we’re revisiting an unfiltered conversation with host Jaclyn Siu and fellow founder Jason about the parts of entrepreneurship that don’t make the highlight reel.</p><p>We kept the mics hot while they unpacked the emotional side of leadership—how it feels to shut down a company, the quiet grief behind layoffs, and the shame founders carry when things don’t go as planned. Together, they reflect on what failure can teach us, how to build healthier definitions of success, and why we need more honest spaces to talk about the “in...

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  Episode #5

  Why This VC Says Failure Is the Best Founder Education

  Sep 16, 202530 minS1

  <p>In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses resilience, risk, and reframing failure with Rockman Ha, Head of Network & Ecosystem at The General Partnership.</p><p>About Our Guest:</p><p>Rockman Ha is a multi-time founder who’s helped scale companies from seed to acquisition. After early roles at MongoDB and Meta, he co-founded the viral social app Peach, later built Clear Talent (acquired by Patreon), and now supports other founders through venture and talent advising at The General Partnership.</p><p>In this episode, we cover:</p>Why failure is a powerful teacher—and...

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