trailer

trailer
Published on:

9th Jul 2025

Round Two - Launching July 2025

When one of my startups shut down, I couldn’t talk about it.

I shrugged. I changed the subject. I avoided the story, even though that chapter shaped me more than any success ever did.

I’ve learned that people WANT to hear that story. So I gathered up some of the most inspiring founders who have walked the same path I have and invited them to share THEIR stories with you.

Round Two is the podcast I wish I had back then. A place where founders talk about the moments that broke them — and how they found the courage, clarity, and grit to build again.

Each episode spotlights a different founder who’s faced failure and still chose to come back stronger.

Because the real magic happens in Round Two!

Show artwork for Round Two

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

Profile picture for Jaclyn Siu

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.