Round Two
Round Two
Podcast Description
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.
Podcast Insights
Content Themes
The podcast centers around themes of startup setbacks, resilience, and personal reinvention. Episodes feature in-depth discussions on topics like redefining failure, emotional well-being in entrepreneurship, and actionable frameworks for recovery. For instance, the episode with Daniel Ahmadizadeh discusses his experiences applying to Y Combinator multiple times and how he reframed entrepreneurship as a problem-solving venture.
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.
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.
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