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

Before Season Two of Round Two begins, we’re revisiting an unfiltered conversation with host Jaclyn Siu and fellow founder Jason about the parts of entrepreneurship that don’t make the highlight reel.

We kept the mics hot while they unpacked the emotional side of leadership—how it feels to shut down a company, the quiet grief behind layoffs, and the shame founders carry when things don’t go as planned. Together, they reflect on what failure can teach us, how to build healthier definitions of success, and why we need more honest spaces to talk about the “in between.”

This bonus episode from Season One of Round Two is warming us up for Season Two with reflective dialogue between two founders who’ve lived it.

In this episode:

• Why founders struggle to separate self-worth from startup success
• What happens when your leadership identity starts to crumble
• How to lead and let go with empathy
• The power of community, honesty, and healing after failure

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?

Discover Starcycle. Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.ai

In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses resilience, risk, and reframing failure with Rockman Ha, Head of Network & Ecosystem at The General Partnership.

About Our Guest:

Rockman Ha is a multi-time founder who’s helped scale companies from seed to acquisition. After early roles at MongoDB and Meta, he co-founded the viral social app Peach, later built Clear Talent (acquired by Patreon), and now supports other founders through venture and talent advising at The General Partnership.

In this episode, we cover:

• Why failure is a powerful teacher—and how to extract its value
• The “regret minimization” framework for making tough decisions
• What it means to lead with radical ownership
• Why early hires should be “general athletes,” not just domain experts
• The importance of transparency with investors and boards
• How to stay steady through volatility and learn from each round

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, 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?

Discover Starcycle. Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.ai