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