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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