Look for any podcast host, guest or anyone
Showing episodes and shows of

Jaclyn Siu

Shows

Round Two
Round TwoTeaching Class With Zero QualificationsIn 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 GuestTim He is a founder and longtime TA of his university’s entrepreneurship program, where he hel...
2025-12-1742 minRound Two
Round TwoThe Phone Call That Ended My StartupTwo 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 grocer...
2025-12-0355 minInside Startup Funding
Inside Startup FundingNavigating the Emotional Toll of Startup Shutdowns - Jaclyn Siu of StarcycleIn this conversation, Jacyln Siu of Starcycle shares her journey from growing up in Hong Kong to becoming a successful entrepreneur in the U.S. She discusses the emotional challenges of shutting down startups, the importance of community and networking, and how these experiences shaped her new venture, Starcycle. The conversation emphasizes resilience, learning from failure, and the significance of building supportive relationships in the entrepreneurial journey.   00:00 From Hong Kong to Entrepreneurship 02:54 The Journey of Learning and Adapting 06:02 The Pain of Shutdowns and Lessons Learned 08:50 The Birth of Star Cycle 12:01 Navigating t...
2025-11-251h 27Round Two
Round TwoThe Things Founders Don’t Say Out Loud: A Bonus Round Two TalkBefore 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...
2025-11-2011 minRound Two
Round TwoWhy This VC Says Failure Is the Best Founder EducationIn 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...
2025-09-1630 minRound Two
Round TwoWhen 5x Ad Costs Erase All Your Startup WinsIn 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 GuestDave 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...
2025-09-0234 minRound Two
Round TwoNo Plan, No Problem? The Scrappy Startup Playbook That Actually WorkedIn 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...
2025-08-1946 minRound Two
Round TwoI 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...
2025-08-0645 minRound Two
Round TwoI 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 iden...
2025-07-1134 minRound Two
Round TwoRound Two - Launching July 2025When 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...
2025-07-0900 minGiant Robots Smashing Into Other Giant Robots
Giant Robots Smashing Into Other Giant Robots529: How AI Transforms Small Business OperationsHost Victoria Guido chats with Jaclyn Siu, the co-founder of Starcycle, an AI platform designed as a COO for small businesses. First, Jaclyn describes her entrepreneurial journey and what led her to Starcycle, detailing her earlier ventures, such as helping to scale a men's styling app and a software platform for authenticating high-end art. Her ultimate goal is to make the tools and experiences typically reserved for startup founders accessible to small business owners, who comprise most of the global business ecosystem. She outlines how Starcycle supports crucial phases in a business’s lifecycle—start-up, sale, or shut...
2024-06-1340 minOn The Up & Up
On The Up & Up2: From a 10 year hiatus from the startup world to becoming a 3x founder | Jaclyn SiuStay in touch & up-to-date via our social: https://linkin.bio/ontheupandup-io -- Hey there Risers and Thrivers! I’m really excited to introduce you to Jaclyn Siu, who is a 3x founder, mentor, educator, and angel investor with deep expertise in the culture, creative, and tech industry. With over 12 years of experience as a growth operator and brand marketer across three continents, she has spearheaded disruptive innovative campaigns and brands for the likes of JAY-Z and Rihanna. Together, we’re going to explore:   Her return to entrepreneurship after a 10 year hiatus...
2023-11-2248 minThe Costume Plot
The Costume Plot55: Kindred with costume designer Jaclyn BannerWe're so excited to be joined by costume designer Jaclyn Banner to chat all about her work designing FX on Hulu's new show Kindred, based on the book by Octavia E. Butler. Jaclyn gives us all the behind the scenes tidbits on selecting fabrics, working closely with actors in fittings, and her path to costume design. Follow Jaclyn!Jaclyn's websiteInstagramFollow along with the visual analysis via these links! Instagram, Pinterest Questions? Comments? Suggestions for future episodes? Email thecostumeplot@gmail.com. Follow us: Jojo Siu on IG...
2023-01-271h 03Kuilei Courageous Conversations
Kuilei Courageous ConversationsWhere Are They Now? Striving for her Highest with Strength, Resiliency, Compassion, and Love (Social Work Degree)Send us a textWhat a way to close out this semester with an awesome AWESOME interview with Malia Ishimura.  In this episode, Malia talks openly about her challenges and successes along her educational journey as a returning adult.  Her selflessness can be witnessed in her position as a  Social Worker assisting youth and families.  Below is just a part of her "Mahalo List" that includes people and programs she wanted to thank.  "To bloom where I am planted."Please enjoy and share widely.LaVache Scanlan, Sarah Akina, Ana Bravo, Jennifer Brown...
2021-04-2745 min