Episode 4

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Published on:

2nd Sep 2025

When 5x Ad Costs Erase All Your Startup Wins

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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About the Podcast

Round Two
From Setback to Comeback
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.

About your host

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Jaclyn Siu

Jaclyn Siu is an entrepreneur, investor, and mentor dedicated to supporting founders at every stage, particularly the challenging ones. Named one of NYC’s Top 50 Underrepresented Founders, she’s built award-winning brands at the intersection of culture and technology, partnering with influential figures like JAY-Z, Rihanna, and acclaimed artists Daniel Arsham and Hajime Sorayama. Jaclyn regularly shares insights on entrepreneurship and innovation at institutions like NYU Stern and Parsons.

As the founder of Starcycle, Jaclyn combines logistical expertise with deep empathy, guiding entrepreneurs through the complex, often-overlooked process of closing businesses thoughtfully and respectfully. She believes every ending is the seed for a new beginning—and she’s here to help founders navigate that transformation with clarity and compassion.