Round Two

About Round Two

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.

Publisher

Jaclyn Siu

Category

business · education · technology

Language

en

Explicit

No

First episode

9 Jul 2025

Latest episode

4 May 2026

Latest episodes

10 episodes in the feed.

1. 

   4 May 2026

   Killing What You Built to Save It

   In this episode, three-time founder and startup advocate Jaclyn Siu sits down with Andrew Bennett, a self-described "person number six" at Provide, now Head of Small Business at Fifth Third Bank. The conversation covers betting on your best friends, knowing when to blow up what you've built, and what actually makes an exit work. Andrew's path to fintech ran through minor league baseball diamonds and college dugouts. He spent most of his twenties coaching before packing his life into two suitcases and flying one-way to San Francisco to join two childhood friends building a small business lending startup. What followed was a decade of pivots, near-death moments, and ultimately an acquisition that he calls the best of both worlds. About Our Guest Andrew Bennett is Head of Small Business at Fifth Third Bank, where he leads the evolved business originally built at Provide, originally a healthcare-focused fintech lender. Before fintech, Andrew spent years coaching baseball at the high school and college level, a background he credits with teaching him more about building teams than he expected. In this episode, we cover: How a baseball coaching career became unlikely preparation for building a company Why focus and not product was the real unlock for Provide's early survival The cultural cost of pivoting when your team is split between two visions Why your acquisition insight matters as much as your product insight The mindset shift from startup operator to leader inside a large organization What small business owners and venture-backed founders actually have in common Listen now for a founder-adjacent story full of hard pivots, shared delusion, and the kind of luck that only shows up after years of hard work. 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. Schedule your onboarding call today.

2. 

   17 Dec 2025

   Teaching Class With Zero Qualifications

   In this podcast episode, three-time founder and startup advocate Jaclyn Siu sits down with Tim He (https://www.linkedin.com/in/timhe2000/), 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 entrepreneurship TA’ing dozens of classes while failing the very course he helped write The question his mentor used to determine whether someone is “ready” to start a company Starting a company out of necessity—and surviving the emotional and operational chaos that followed Recruiting co-founders, navigating breakups, and learning when to let go How 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 (http://starcycle.ai)

3. 

   3 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 (https://www.linkedin.com/in/helenafogarty/) — co-founder of Backable (https://backableco.com/) and host of Inside the Round (https://bamboo-x.com/blog/tag/podcasts)— 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. Need help navigating a winddown? Starcycle (https://starcycle.ai/) 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 (https://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

4. 

   20 Nov 2025

   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 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 (https://starcycle.ai/). Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.ai (https://starcycle.ai/)

5. 

   16 Sept 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 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 (https://starcycle.ai/). Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.ai (https://starcycle.ai)

6. 

   2 Sept 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 (https://starcycle.ai/). Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.a (https://starcycle.ai/)

7. 

   19 Aug 2025

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

   In this episode, three-time founder and startup advocate Jaclyn Siu (https://www.linkedin.com/in/jaclynsiu/) sits down with Izayah “Zay” Powell (https://www.linkedin.com/in/izayahpowell/), Founder & COO of VidCade, to unpack why the best entrepreneurs treat failure like data—not defeat. About our guest Isaiah 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 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 (https://starcycle.ai/). Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.a (https://starcycle.ai/)

8. 

   5 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 (https://www.openforge.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 (https://www.linkedin.com/in/pateljason/) 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? Discover Starcycle (https://starcycle.ai/). Wind-down plans start at $299, tailored to your needs, with no hidden fees. Get started today at starcycle.ai (https://starcycle.ai/)

9. 

   11 Jul 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 in How shutting down a company impacted his identity and mental health Reframing entrepreneurship as problem-solving rather than personal validation “Start With One” — a powerful framework for founders feeling lost or stuck Teaching the next generation of builders how to grow confidence and take meaningful first steps What 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 (https://starcycle.ai/). We support founders in closing chapters and opening new ones—with empathy and clarity.

10. 

    9 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!