Round Two

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. Andrew's path to fintech ran through minor league baseball diamonds a...

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 less...

Two shutdowns. Two completely different emotional realities. One founder who lived both. In this episode of Round Two, host Jaclyn Siu sits down with Helena Fogarty — co-founder of Backable and host of I nside 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. Helena shares the inside story of: The last-minut...

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. 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 pla...

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. About Our Guest: 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 bui...

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 . About Our Guest Dave Rosen is a seasoned entrepreneur and operator with over two decades of leadership experience in video games, media, and technology. As the former CEO of Wimo Games, Dave led teams through...

In this episode, three-time founder and startup advocate Jaclyn Siu sits down with I zayah “Zay” Powell , Founder & COO of VidCade, to unpack why the best entrepreneurs treat failure like data—not defeat. About our guest Isaiah grew up with an immigrant mother in New York City, parlayed campus fashion shows into sponsorship deals, helped spark the NCAA name-image-likeness revolution, and now r...

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 about what happens when big dreams slam into hard reality—and how you build your way back. About our guest Jason Patel bootstrapped his first ed-tech startup, survived a quarter-m...

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. About Our Guest: Daniel Ahmadizadeh is an entrepreneur, educator, and seven-time Y Combinator applicant turned founder. Daniel’s journey spans teaching at Stanford and Columbia, consulting for early-stage founders, a...

When one of my startups shut down, I couldn’t talk about it. I shrugged. I changed the subject. I avoided the story, even though that chapter shaped me more than any success ever did. I’ve learned that people WANT to hear that story. So I gathered up some of the most inspiring founders who have walked the same path I have and invited them to share THEIR stories with you. Round Two is the podcast I...