Round Two

Jaclyn Siu

0.0 (0)
ENTREPRENEURSHIP

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.

12/17/2025

Teaching Class With Zero Qualifications

In this podcast episode, three-time founder and startup advocate Jaclyn Siu sits down with Tim He, a founder whose journey defies every expectation and embraces every contradiction. Tim went from failing the same entrepreneurship class he helped write, to TA’ing 30+ courses, to starting a company mostly because he couldn’t get a traditional job. His story blends humor, humility, and hard-won lessons about identity, readiness, co-founder dynamics, and building before you believe you're qualified. About Our Guest Tim He is a founder and longtime TA of his university’s entrepreneurship program, where he helped design midterms, shape curriculum, and teach hundreds of students—despite never being admitted to the business school himself. Tim later founded his first company while still in college, navigating co-founder selection, team dynamics, early traction, burnout, and the emotional cost of choosing friendship over a company. In this episode, we cover: How a chance encounter at a mall job led Tim into entrepreneurshipTA’ing dozens of classes while failing the very course he helped writeThe question his mentor used to determine whether someone is “ready” to start a companyStarting a company out of necessity—and surviving the emotional and operational chaos that followedRecruiting co-founders, navigating breakups, and learning when to let goHow insecurity and confidence collide in early-stage building Listen now to hear a founder story shaped by contradictions, hard pivots, and the kind of lessons you can only learn by doing. About Round Two Round Two, hosted by Jaclyn Siu, rewrites the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts. Looking for guidance during your own transition? Starcycle supports founders in closing chapters and opening new ones—with empathy and clarity. Starting at $299. Tailored to your needs. No hidden fees. Get started today at starcycle.ai

43 min
12/03/2025

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 investorCalling her co-founder to say “We’re done”Taking over as CEO of a CPG brand already in freefallHow a rebrand destroyed a $2M grocery businessWhat 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 TwoRound Two, hosted by Jaclyn Siu, rewrites the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts and join the conversation. Need help navigating a winddown? Starcycle helps founders close their companies with confidence. We handle every part of your wind-down with precision, from filings and final taxes to investor and customer communications. With transparent pricing and human guidance at every step, we make closure easy and help you move forward with clarity. Get started today at starcycle.ai ✨ 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

55 min
11/20/2025 · BONUS

The Things Founders Don’t Say Out Loud: A Bonus Round Two Talk

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 successWhat happens when your leadership identity starts to crumbleHow to lead and let go with empathyThe power of community, honesty, and healing after failure About Round TwoRound 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

11 min
09/16/2025

Why This VC Says Failure Is the Best Founder Education

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 valueThe “regret minimization” framework for making tough decisionsWhat it means to lead with radical ownershipWhy early hires should be “general athletes,” not just domain expertsThe importance of transparency with investors and boardsHow 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 TwoRound 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

30 min
09/02/2025

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. 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.a

35 min
08/19/2025

No Plan, No Problem? The Scrappy Startup Playbook That Actually Worked

In this episode, three-time founder and startup advocate Jaclyn Siu sits down with Izayah “Zay” Powell, Founder & COO of VidCade, to unpack why the best entrepreneurs treat failure like data—not defeat. About our guestIsaiah grew up with an immigrant mother in New York City, parlayed campus fashion shows into sponsorship deals, helped spark the NCAA name-image-likeness revolution, and now runs a VC-backed gaming startup that’s redefining social play. In this episode, we cover:“Failing correctly.” Zay explains why “situations—failure—are never going away,” and why learning beats avoiding risk.Data over drama. The scariest outcome isn’t failure; it’s failure with no lessons attached.Mental health & ego management. How student-athlete setbacks forged Zay’s resilience and mindset for high-stakes fundraising.Cold-outreach courage. From sliding into investor inboxes to converting rejections into momentum.Building an all-weather team. Why co-founder chemistry and “people in your corner” matter more than credentials.Reframing the narrative. Jaclyn’s insight that “if you’re not failing, you’re doing something wrong” and what that means for founders everywhere. Listen now to explore the realities of entrepreneurship—where setbacks become stepping-stones and honest stories fuel powerful comebacks. About Round TwoRound 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.a

46 min
08/05/2025

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 guestJason 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 coverThe “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 itA five-step framework for stress-testing new ideas: market size, purchasing power, liquidity, and more before you commit to the next pivotRebounding 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 TwoRound 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

46 min
07/11/2025

I Applied to Y Combinator 7 Times. Then I Shut the Company Down.

In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses resilience, reinvention, and redefining failure with Daniel Ahmadizadeh, founder and CEO of Time. About Our Guest: Daniel Ahmadizadeh is an entrepreneur, educator, and seven-time Y Combinator applicant turned founder. Daniel’s journey spans teaching at Stanford and Columbia, consulting for early-stage founders, and navigating the emotional terrain of shutting down his YC-backed company. In this episode, we cover: Why Daniel applied to Y Combinator seven times — and what happened when he finally got inHow shutting down a company impacted his identity and mental healthReframing entrepreneurship as problem-solving rather than personal validation“Start With One” — a powerful framework for founders feeling lost or stuckTeaching the next generation of builders how to grow confidence and take meaningful first stepsWhat Daniel is doing differently this time around 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 online. Looking for guidance during your own entrepreneurial transition? Discover Starcycle. We support founders in closing chapters and opening new ones—with empathy and clarity.

34 min
TRAILER

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!

1 min

TRAILER

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!

07/09/2025

•

1 min

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.

Creator

Jaclyn Siu
Years Active

2K
Episodes

9
Rating

Clean
Copyright

© Copyright 2025 Jaclyn Siu
Show Website

Round Two