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.
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Contact path
Public web form
Booking probability
26%
Guest openness
Selective
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Signup to Generate a PitchJoin 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 hosted by Jaclyn Siu. The show has published 10 episodes to date.
Recent episodes include "Killing What You Built to Save It" (4 May 2026, 48 minutes), "Teaching Class With Zero Qualifications" (17 December 2025, 43 minutes), and "The Phone Call That Ended My Startup" (3 December 2025, 55 minutes).
Round Two publishes roughly every two weeks, with episodes averaging 35 minutes across 10 episodes.
Booking probability for Round Two is 26%, and the host is rated Selective on guests. Round Two requires a Pod Score of 80 or higher. Round Two's contact route on record: public web form.
The strongest fits for Round Two are Business & Management Consulting. Round Two has a business audience.
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.
Episode #3
<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...
Episode #2
<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...
Episode #1
<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...
Episode #6
<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...
Episode #5
<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...
Episode #4
<p>In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses failure, pivots, and the human cost of resilience in startups with Dave Rosen, former CEO of Wimo Games.</p><p>About Our...
Episode #3
<p>In this episode, three-time founder and startup advocate Jaclyn Siu sits down with Izayah “Zay” Powell, Founder & COO of VidCade, to unpack why the best entrepreneurs treat failure like data—not defeat.</p><h4>About...
Episode #2
<p>In this episode of Round Two: From Setback to Comeback, three-time founder and Starcycle CEO Jaclyn Siu sits down with Jason Patel, Founder & CEO of Open Forge AI and previously Founder of Transizion, to talk frankly...
Episode #1
<p>In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses resilience, reinvention, and redefining failure with Daniel Ahmadizadeh, founder and CEO of Time.</p><p>About Our...
Round Two
<p>When one of my startups shut down, I couldn’t talk about it.</p><p>I shrugged. I changed the subject. I avoided the story, even though that chapter shaped me more than any success ever did.</p><p>I’ve learned that...
Recent guests on Round Two. Study who booked and why before you pitch.
Director of the FRAME Alternatives Laboratory, University of Minnesota
founder and marketing leader, Open Forge AI
Backable
The General Partnership
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