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 built Clear Talent (acquired by Patreon), and now supports other founders through venture and talent advising at The General Partnership.

In this episode, we cover:

• Why failure is a powerful teacher—and how to extract its value
• The “regret minimization” framework for making tough decisions
• What it means to lead with radical ownership
• Why early hires should be “general athletes,” not just domain experts
• The importance of transparency with investors and boards
• How to stay steady through volatility and learn from each round

Listen now to explore the realities of entrepreneurship—where setbacks become stepping stones, and honest stories lead to powerful comebacks.

About Round Two

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

Looking for guidance during your own entrepreneurial transition?

Discover Starcycle. Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.ai

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 moments of high growth, painful pivots, and ultimately, the difficult decision to wind down. His candid reflections highlight not only the practical side of startup leadership but also the emotional weight of navigating setbacks.

In this episode, we cover:

• Why failure is impermanence, not identity — and why that distinction matters for every founder.
• The role of timing and luck in startup success, and why even strong metrics can’t always save you.
• How external shifts (like rising ad costs) can unravel solid business models overnight.
• The human cost of pivoting, including layoffs, morale shifts, and leadership trade-offs.
• Why runway is time — and time is the greatest gift a founder can give themselves.
• How radical transparency with teams and investors builds resilience, even through shutdowns.
• Naming and escaping the “shame spiral” that often traps founders facing failure.
• Why resilience is ultimately about perspective, community, and remembering that failure is temporal.

Listen now to explore the realities of entrepreneurship—where setbacks become stepping stones, and honest stories lead to powerful comebacks.

About Round Two

Round Two, hosted by Jaclyn Siu, is dedicated to rewriting the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts and join the conversation.

Looking for guidance during your own entrepreneurial transition?

Discover Starcycle. Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.a

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.

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 runs a VC-backed gaming startup that’s redefining social play.

In this episode, we cover:

• “Failing correctly.” Zay explains why “situations—failure—are never going away,” and why learning beats avoiding risk.
• Data over drama. The scariest outcome isn’t failure; it’s failure with no lessons attached.
• Mental health & ego management. How student-athlete setbacks forged Zay’s resilience and mindset for high-stakes fundraising.
• Cold-outreach courage. From sliding into investor inboxes to converting rejections into momentum.
• Building an all-weather team. Why co-founder chemistry and “people in your corner” matter more than credentials.
• Reframing the narrative. Jaclyn’s insight that “if you’re not failing, you’re doing something wrong” and what that means for founders everywhere.

Listen now to explore the realities of entrepreneurship—where setbacks become stepping-stones and honest stories fuel powerful comebacks.

About Round Two

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

Looking for guidance during your own entrepreneurial transition?

Discover Starcycle. Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.a

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-million-dollar debt spiral, turned the company around to a strategic exit, and is now building Open Forge AI to help B2B marketing teams create content that wins in an AI-search world. His super-power? Relentless grit.

In this episode we cover

• The “performative founder” trap: why chasing vanity VC metrics nearly sank Jason’s first company
• $250K in credit-card debt & the turnaround playbook: how under-pricing for growth backfired and what finally reversed the slide
• “Building something people didn’t want”—the classic product-market-fit mistake and how to avoid it
• A five-step framework for stress-testing new ideas: market size, purchasing power, liquidity, and more before you commit to the next pivot
• Rebounding from a blown-out knee while in a top accelerator—and why physical setbacks mirror startup failures

Listen now to hear how raw failures become rocket fuel for smarter, saner comebacks.

About Round Two

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

Looking for guidance during your own entrepreneurial transition?

Discover Starcycle. Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.ai

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, and navigating the emotional terrain of shutting down his YC-backed company.

In this episode, we cover:

• Why Daniel applied to Y Combinator seven times — and what happened when he finally got in
• How shutting down a company impacted his identity and mental health
• Reframing entrepreneurship as problem-solving rather than personal validation
• “Start With One” — a powerful framework for founders feeling lost or stuck
• Teaching the next generation of builders how to grow confidence and take meaningful first steps
• What Daniel is doing differently this time around

Listen now to explore the realities of entrepreneurship—where setbacks become stepping stones, and honest stories lead to powerful comebacks.

About Round Two:

Round Two, hosted by Jaclyn Siu, is dedicated to rewriting the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts and join the conversation online.

Looking for guidance during your own entrepreneurial transition?

Discover Starcycle. We support founders in closing chapters and opening new ones—with empathy and clarity.

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 wish I had back then. A place where founders talk about the moments that broke them — and how they found the courage, clarity, and grit to build again.

Each episode spotlights a different founder who’s faced failure and still chose to come back stronger.

Because the real magic happens in Round Two!