Episode 1

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Published on:

3rd Dec 2025

The Phone Call That Ended My Startup

Two shutdowns. Two completely different emotional realities. One founder who lived both.

In this episode of Round Two, host Jaclyn Siu sits down with Helena Fogarty — co-founder of Backable and host of Inside the Round — to talk about the moments that force founders to confront the truth: sometimes the math or the market doesn’t give you a choice.

Helena shares the inside story of:

  • The last-minute reversal from her lead angel investor
  • Calling her co-founder to say “We’re done”
  • Taking over as CEO of a CPG brand already in freefall
  • How a rebrand destroyed a $2M grocery business
  • What she’s learned about raising, shutting down, and starting again

This conversation pulls back the curtain on the emotional, operational, and financial realities of startup shutdowns — and what it takes to rebuild with clarity.

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.

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✨ Episode Highlights

00:00 Why Round Two Exists

01:11 Meet Helena Fogarty

01:53 The Apparel Startup & Angel Investor Reversal

14:06 The Phone Call: “Hey… We’re Done.”

20:27 Founder Grief, Identity & Collapse

21:07 The Unexpected CEO Offer

24:12 Walking Into a Failing CPG Brand

25:30 How a Rebrand Destroyed a $2M Business

37:41 How to Shut Down a Company Elegantly

46:28 Why Failure Makes Better Founders

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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.