Round Two

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.

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]

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

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/]

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]