Episode 2

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Published on:

5th Aug 2025

I Racked Up $250K in Debt Chasing Vanity Growth!

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?

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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.