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.
Podcast Overview
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.
Language
🇺🇲
Publishing Since
7/9/2025
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Recent Episodes
May 4, 2026
Killing What You Built to Save It
<p>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.</p><p>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.</p><p><strong>About Our Guest</strong> 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.</p><p><strong>In this episode, we cover:</strong></p><ul><li>How a baseball coaching career became unlikely preparation for building a company</li><li>Why focus and not product was the real unlock for Provide's early survival</li><li>The cultural cost of pivoting when your team is split between two visions</li><li>Why your acquisition insight matters as much as your product insight</li><li>The mindset shift from startup operator to leader inside a large organization</li><li>What small business owners and venture-backed founders actually have in common</li></ul><br/><p>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.</p><p><strong>About Round Two</strong></p><p>Round Two, hosted by Jaclyn Siu, rewrites the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts.</p><p><strong>Looking for guidance during your own transition?</strong></p><p>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.</p>
December 17, 2025
Teaching Class With Zero Qualifications
<p>In this podcast episode, three-time founder and startup advocate Jaclyn Siu sits down with <a href="https://www.linkedin.com/in/timhe2000/" rel="noopener noreferrer" target="_blank">Tim He</a>, a founder whose journey defies every expectation and embraces every contradiction.</p><p>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.</p><p><strong>About Our Guest</strong></p><p>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.</p><p><strong>In this episode, we cover:</strong></p><ul><li>How a chance encounter at a mall job led Tim into entrepreneurship</li><li>TA’ing dozens of classes while failing the very course he helped write</li><li>The question his mentor used to determine whether someone is “ready” to start a company</li><li>Starting a company out of necessity—and surviving the emotional and operational chaos that followed</li><li>Recruiting co-founders, navigating breakups, and learning when to let go</li><li>How insecurity and confidence collide in early-stage building</li></ul><br/><p>Listen now to hear a founder story shaped by contradictions, hard pivots, and the kind of lessons you can only learn by doing.</p><p><strong>About Round Two</strong></p><p>Round Two, hosted by Jaclyn Siu, rewrites the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts.</p><p>Looking for guidance during your own transition?</p><p>Starcycle supports founders in closing chapters and opening new ones—with empathy and clarity. Starting at $299. Tailored to your needs. No hidden fees.</p><p>Get started today at <a href="http://starcycle.ai" rel="noopener noreferrer" target="_blank">starcycle.ai</a></p>
December 3, 2025
The Phone Call That Ended My Startup
<p>Two shutdowns. Two completely different emotional realities. One founder who lived both.</p><p>In this episode of Round Two, host Jaclyn Siu sits down with <a href="https://www.linkedin.com/in/helenafogarty/" rel="noopener noreferrer" target="_blank">Helena Fogarty</a> — co-founder of <a href="https://backableco.com/" rel="noopener noreferrer" target="_blank">Backable</a> and host of I<a href="https://bamboo-x.com/blog/tag/podcasts" rel="noopener noreferrer" target="_blank">nside the Round </a>— to talk about the moments that force founders to confront the truth: sometimes the math or the market doesn’t give you a choice.</p><p>Helena shares the inside story of:</p><ul><li>The last-minute reversal from her lead angel investor</li><li>Calling her co-founder to say “We’re done”</li><li>Taking over as CEO of a CPG brand already in freefall</li><li>How a rebrand destroyed a $2M grocery business</li><li>What she’s learned about raising, shutting down, and starting again</li></ul><br/><p>This conversation pulls back the curtain on the emotional, operational, and financial realities of startup shutdowns — and what it takes to rebuild with clarity.</p><h4>About Round Two</h4><p>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.</p><p>Need help navigating a winddown?</p><p><a href="https://starcycle.ai/" rel="noopener noreferrer" target="_blank">Starcycle</a> helps founders close their companies with confidence. </p><p>We handle every part of your wind-down with precision, from filings and final taxes to investor and customer communications.</p><p>With transparent pricing and human guidance at every step, we make closure easy and help you move forward with clarity.</p><p>Get started today at <a href="https://starcycle.ai/" rel="noopener noreferrer" target="_blank">starcycle.ai</a></p><p>✨ Episode Highlights</p><p>00:00 Why Round Two Exists </p><p>01:11 Meet Helena Fogarty </p><p>01:53 The Apparel Startup & Angel Investor Reversal </p><p>14:06 The Phone Call: “Hey… We’re Done.” </p><p>20:27 Founder Grief, Identity & Collapse </p><p>21:07 The Unexpected CEO Offer </p><p>24:12 Walking Into a Failing CPG Brand </p><p>25:30 How a Rebrand Destroyed a $2M Business </p><p>37:41 How to Shut Down a Company Elegantly </p><p>46:28 Why Failure Makes Better Founders </p>
10 total episodes available
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