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Richard Kerby has worked in investment banking and venture, co-founded Equal Ventures, and just launched Fund I for Field Ventures. Most investors talk about going from zero to one. Kerby focuses on the zero: the months before a founder writes a line of code, when picking the right problem matters more than building fast.In this conversation with Brandon Bryant of Harlem Capital, Kerby explains why Field makes only about 20 investments per fund and talks to every founder every two weeks. He also walks through his service-as-a-software thesis, where AI stops being a tool and starts doing the work itself. Along the way he covers why antiquated industries are the biggest opportunity in AI, why domain expertise now matters more than technical talent, and why Field never votes on deals.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:25 Investing From Inception3:01 Why Founders Should Pump the Brakes5:01 The Case for Concentrated Bets7:18 Founder Check-Ins Every Two Weeks9:19 Service-as-a-Software Explained14:44 Where Voice AI Actually Works17:06 How AI Changed Founder Evaluation21:25 Boutique Firms vs. Multi-Stage Firms27:01 Thesis-Led vs. Founder-Led Investing30:05 Solo GPs and Why Field Doesn't Vote on Deals34:53 Field Ventures 10 Years Out36:42 The Roller Coaster Test38:51 Raising Fund I With Radical Transparency41:27 New York, San Francisco, and BeyondMore on Richard:https://www.linkedin.com/in/richardkerby/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Teddy Solomon dropped out of Stanford at 19 to build Fizz, the anonymous campus social app that's now live on 800 college campuses and closing in on 1,500 by the end of the year. In this episode, Teddy tells Jarrid Tingle the full story: how a COVID-era dorm launch turned into a company that's raised over $40 million, why he personally visited nearly 290 campuses to hand out donuts and win over students one school at a time, and how Fizz recently hit number one overall on Saudi Arabia's App Store, ahead of ChatGPT, Gemini, and TikTok.They get into why Teddy moved his entire team from San Francisco to New York, how Fizz built an ads business without wrecking the user experience, what most companies get wrong about Gen Z, and the one trait Teddy looks for in every hire. This episode is powered by Gunderson Dettmer.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:22 Meet Teddy Solomon, CEO of Fizz1:33 The Origin Story: Building Fizz During COVID4:45 Launch Day at Stanford7:03 Visiting Nearly 300 Campuses (and Getting Chased by Campus Police)10:47 The Moment Fizz Becomes Unstoppable12:23 Finding a Mentor and Handing Over the CEO Role15:33 Should You Drop Out of College to Build a Startup?17:41 Moving the Whole Team From SF to NYC21:29 Building Fizz's Ads Business26:03 Going Global: Hitting #1 in Saudi Arabia30:01 Reputation, Leaderboards, and What Makes Fizz Sticky31:35 What Everyone Gets Wrong About Gen Z34:44 Teddy's Approach to Fundraising37:16 Hiring for Storytelling and Teddy's Superpower40:51 The Long-Term Vision for FizzMore on Teddy:https://www.linkedin.com/in/teddy-solomon-85a183188/More on Jarrid:https://www.linkedin.com/in/jarrid-tingle/The Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Julie Samuels has spent a decade building the connective tissue between New York City's tech industry and its government. As President and CEO of Tech:NYC, she's become one of the most trusted voices bridging Silicon Alley and City Hall, translating policy for founders and founders for policymakers.In this conversation with Jarrid Tingle, Julie traces Tech:NYC's founding story, unpacks the current political dynamics under Governor Hochul and Mayor Mamdani, and makes the case for why New York's tech ecosystem is built differently than San Francisco's. She digs into the city's affordability crisis, the Grid Fellowship program training tech executives in civic literacy, and her philosophy on relationship building that guides everything from local politics to national policy. The conversation closes with her candid takes on congestion pricing, ranked choice voting, and what the next decade of NYC tech could look like.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:05 TechNYC's Founding Story4:15 Liaison Between Tech and Government6:08 Governor Hochul and Empire AI7:14 Mayor Mamdani and the New Political Landscape9:51 The Empathy Behind Political Leadership12:18 New York vs. San Francisco: Why Build Here17:20 What Would Make NYC Even Better for Tech19:37 The Affordability Crisis28:10 The Grid Fellowship32:31 When and How Tech Leaders Should Engage With Government36:58 The Secret to Building Real Relationships40:18 Making Events People Actually Want to Attend43:01 Congestion Pricing and Ranked Choice Voting48:05 Julie's Vision for NYC Tech's Next DecadeMore on Julie:https://www.linkedin.com/in/juliepsamuels/More on Jarrid:https://www.linkedin.com/in/jarrid-tingle/The Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Nihal Mehta co-founded ENIAC Ventures nearly 16 years ago with a $1.5 million fund. Today the firm invests out of a $220 million fund and has become one of New York's most active early-stage backers of AI-native companies. In this episode, Nihal breaks down how he's built an "army of AI agents" using Claude to source deals, screen inbound pitches, and even run diligence on a live term sheet, plus why he believes New York, not San Francisco, is where consumer and enterprise AI applications will be built and won.The conversation also covers how ENIAC has stayed lean and partner-centric since day one, why density of ambition gives New York an edge San Francisco can't replicate, and the philosophy behind Nihal's self-proclaimed "human rolodex," including Pitch and Run, the global founder running community he co-founded, and Human Unicorns, his deep dive into the people behind billion-dollar outcomes.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro0:58 Meet Nihal Mehta (and His Dog, Steve)1:19 From a $1.5M Fund to $220M: How ENIAC Has Evolved4:46 Building an Army of AI Agents Inside a VC Firm6:07 Using Claude to Kill FOMO on Inbound Deals8:06 How Claude Diligenced a Live Term Sheet10:27 What Happened With That Deal12:41 What New York Has That San Francisco Doesn't17:02 Signal vs. Noise: Spotting Real AI Companies19:35 Why New York Is Primed for the AI Application Layer22:39 Becoming a "Human Rolodex"26:04 The Jain Philosophy Behind Giving Without Asking28:20 Pitch and Run: Building Community Through Running33:05 Human Unicorns and the Friends Who Built Billion-Dollar Companies36:36 Reputation, Consistency, and Playing the Long GameMore on Nihal:https://www.linkedin.com/in/nihalmehta/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Ben Sun co-founded Primary Venture Partners in 2015 on a simple, contrarian bet: that New York City was an overlooked startup ecosystem on the edge of an inflection point. A decade later, Primary manages $1.6 billion and Ben serves as Head of R&D, running incubations and new ventures including Altis, a research platform bringing institutional-grade diligence to an industry that has historically lacked it.We talk about his path from founding Community Connect (the parent company of Asian Avenue and BlackPlanet) to angel investing in Coupang and building what became Primary's "industrialized seed" model, complete with in-house recruiting, go-to-market, and AI tooling teams. Ben also shares why deals per partner matters more than fund size, his contrarian take on the "bigger funds mean worse returns" debate, and what he's learned about betting on people over ideas.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:11 Founding Community Connect and Asian Avenue6:05 Meeting Bob Goldhammer and Learning to Bet on People10:26 What VCs Get Wrong About Helping Founders14:41 The Coupon Story and Meeting Bomb Kim21:57 How Ben Met Brad and Founded Primary25:56 Betting Early on New York City28:00 How the Secret Got Out and Competition Increased30:50 Building an Industrialized Seed Market35:06 The Structural Advantage of Scale38:21 How Primary Uses AI Internally41:01 Inside Altis: Bringing Research to Venture48:38 Time Management and Prioritization Lessons53:56 Giving Back and Building the Ecosystem56:46 Hot Take: Why Bigger Funds Don't Mean Worse Returns59:50 Legacy and Building the Firm He Wished He HadMore on Ben:https://www.linkedin.com/in/benjaminsun/More on Jarrid:https://www.linkedin.com/in/jarrid-tingle/The Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Deepak Chhugani is a two-time founder and the CEO of Nuvocargo, the agentic platform powering North American freight end to end. Since raising over $85 million from QED Investors, NFX, and others, Nuvocargo just shipped its biggest launch yet: Nuvo AI, a fully agentic freight execution engine with more than a dozen specialized AI agents running everything from carrier negotiations to invoice auditing.In this episode, Deepak breaks down why Nuvocargo bets on outcomes over tools, how freight brokers are becoming more strategic (not obsolete) as AI takes on repetitive work, and the thinking behind Nuvocargo's first acquisitions. He also gets into his angel investing philosophy, why relationships with other CEOs have shaped how he hires and leads, and what it means to build a true "culture of builders" in the age of AI.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:12 Meet Deepak Chhugani, Founder & CEO of Nuvocargo1:46 What Nuvo AI Is and Why They Built It2:41 Inside the 12 AI Agents Running Freight4:26 Why Outcomes Beat Tools6:00 Pricing in the Age of AI Automation7:25 Keeping Humans in the Loop10:10 Becoming an AI Native Company14:02 Growing Through Acquisitions19:04 Blending Culture After an Acquisition22:03 Raising Capital for a Non-Traditional Model24:59 The Long-Term Data Play in Freight27:20 Hiring and the Future of Research32:34 Why Deepak Angel Invests36:46 Building Real Relationships With Other CEOs41:29 Leadership and Culture in the Age of AIMore on Deepak:https://www.linkedin.com/in/deepakchhugani/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://www.linkedin.com/in/bbryantwsp/https://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Charles Yoo-Naut is the Co-Founder and CTO of Rain, the stablecoin payments infrastructure platform that scaled from a side project to a $2 billion company in under four years. A two-time founder, Charles sold his first company to Intuit in 2015 and spent nearly five years there learning how to ship products at scale before leaving to start the idea maze all over again. The conversation covers why Rain was born out of the realization that money was still stuck in the mainframe era, what it took to secure Visa Principal Member status and unlock 7-day stablecoin settlement, and how Charles raised three rounds in 12 calendar months by letting the business speak for itself.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro0:53 Stanford, Microsoft, and Saving $50K to Start2:47 Selling the First Startup to Intuit4:10 The Idea Maze: How to Pick a Direction and Make Progress6:46 How SignAndWire Started as a Side Project10:47 The Christmas Day USDC Moment That Led to Rain13:02 What It Is Really Like to Found a Company Twice16:44 Why Rain Partnered With Visa and Unlocked 7-Day Settlement21:52 What Stablecoins Are and Why 1% of M2 Is Just the Start27:50 Raising Three Rounds in 12 Months30:56 Scaling From 20 to 120 People and Building a Flat Culture35:21 Acquisitions, AI Strategy, and Building Rain's Full Stack39:23 Why Rain Is Betting on New YorkMore on Charles:https://www.linkedin.com/in/charlesnaut/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Molly Fowler has spent seven years running Dorm Room Fund, a student-led venture fund built out of First Round Capital that has backed over 500 student founders and produced eight unicorns, including an early check into Cursor. In this episode, she breaks down why campus remains one of venture's last true information asymmetry plays, how she finds the builders who are off the grid and already shipping, and what the DRF model actually looks like under the hood.We get into the origins of the fund, how Molly selects and trains a team of 60 student investors each year, why the "braces off" moment for DRF came through the Cursor bet, and how she thinks about backing young founders in the age of AI. She also shares what she's watching for as the fund matures, from LP strategy to alum investing to the next phase of growth.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:03 The Origin and Thesis Behind Dorm Room Fund3:08 Why Tech Shifts Level the Playing Field for Student Founders6:11 How DRF Expanded From Philly to a National Fund8:49 The Structure of DRF's 60-Person Student Investing Team12:33 How DRF Got Into Cursor14:06 The "Braces Off" Moment and What It Meant for the Fund15:19 Recruiting the Best Student Investors in the Country21:04 Finding Off-the-Grid Founders Who Are Already Building26:07 How Molly Trains a Team That Turns Over Every Year30:10 How the LP Narrative Has Evolved Over Time33:16 Why Pre-Seed Is One of Venture's Last Information Asymmetry Plays36:16 What Dorm Room Fund Looks Like in 5 to 10 Years39:55 How Young Founders Are Thinking About AI43:14 ClosingMore on Molly:https://www.linkedin.com/in/molly-fowler/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Today's conversation with Ben Lerer covers what most investors won't say out loud: consensus investing is a bad business. We unpack the AI hype cycle, why New York is positioned to win the application layer era, and how Lerer Hippeau built a $1.4B seed franchise on non-obvious bets. And we go deep on what it actually takes to raise a ninth fund, build real LP partnerships, and stay non-consensus when everyone around you is chasing the same deals.Ben Lerer is the co-founder and Managing Partner of Lerer Hippeau, one of New York's leading seed funds. Over 15 years, the firm has backed more than 450 companies and produced 12 unicorns, 7 IPOs, and over 160 acquisitions.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:02 Ben Lerer's Background and 15 Years Building in New York3:49 New York vs. San Francisco: Where the AI Opportunity Really Is4:36 Hot Take: Is the AI Hype Cycle Over?6:51 Why Application Layer Is New York's Moment8:30 The Cost of Building Has Collapsed. What That Means for Venture.11:45 Why Non-Consensus Bets Win: The LH Investment Philosophy14:24 Portfolio Spotlight: Agodoto and Kaledan18:51 Venture Capital Should Take Risks Nobody Wants to Take20:41 Building a Generational Firm: Ecosystem, Events, and Community24:31 The Fundraising Playbook: LPs, DPI, and the Three Fund Hump27:33 Why Money Is Not Just Money: Quality of Capital Matters31:13 Selling the Future, Not the Past: How LH Raised Fund 936:42 Running LP Relationships Like a Sales Process40:53 Rigor vs. Flexibility: The Thing That Keeps Ben Up at Night41:09 The Jealousy Moment: How Ben Evaluates Deals44:17 How Lerer Hippeau Wins Competitive Deals50:14 Is Consumer Dead? Ben's Honest Take52:18 Portfolio Spotlight: Board (from the founder of Mirror)54:55 Closing ThoughtsMore on Ben:https://www.linkedin.com/in/benlerer/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

In this episode of Winners Welcome, we sit down with Deon Nicholas, founder and CEO of Espa AI, the AI executive assistant built for founders, operators, and anyone trying to achieve more. Before Espa, Deon founded Forethought, where he raised over $115M and became one of the earliest leaders in AI customer service, well before the current AI wave.Deon shares how he first got into AI as a high school intern in 2009, why he believes we're entering a consumer renaissance powered by agentic AI, and what he's seeing now that most people haven't caught onto yet. We also get into how he thinks about talent in the age of AI, the humility-confidence balance every founder needs, what it takes to build a personal brand as a technical founder, and why Espa is designed to make executive-level support accessible to everyone, not just the top 1%.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:08 Raising $115M Pre-AI, Pre-Pandemic1:27 Discovering AI in High School in 20094:00 Building His First AI Learning Tool5:43 From Waterloo to Silicon Valley7:17 Why Customer Service Became the First Big AI Market9:38 Founding Forethought and Winning TechCrunch Disrupt10:40 The Aha Moment Behind Espa and Agentic AI13:38 How Deon Uses Espa Every Day15:51 Going Zero to One Again in a New AI Era17:55 Competitive Programming and the Roots of Grit22:40 How to Recruit World-Class Talent27:55 The Long-Term Vision for Espa30:28 Storytelling, Brand, and Becoming the Face of a Company33:43 Building an Authentic Personal Story as a Founder36:08 Where to Find EspaMore on Deon:https://www.linkedin.com/in/deon-nicholas/Check out Espa AI:https://espa.ai/More on Gabby:https://www.linkedin.com/in/gabriellecazeau/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

In this episode, Aman Mathur joins us to unpack how AI is reshaping the way software gets built. We talk about what’s changed inside Replit as the platform has scaled, why AI agents are lowering the barrier to creation, and what it takes to move from experimenting with prompts to actually shipping real products. The conversation also explores the future of software creation as design, development, and deployment become increasingly compressed into one workflow.Aman Mathur is a product leader at Replit, where he has helped drive the company’s product strategy during a period of rapid growth and major AI breakthroughs. Replit is building an AI-powered platform that helps anyone create and launch software faster, from first-time builders to large enterprise teams, with a broader mission of bringing the next generation of software creators online.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:04 Aman's Background and Replit's Growth2:00 From Education Tool to AI-Powered Platform3:47 Early Days at Replit: What Went Right and Wrong5:11 Who Is Building on Replit Today6:04 From Side Project to Revenue: The New Builder Economy6:40 The Agent Timeline: Agent 1 Through Agent 410:39 The Design Canvas Explained13:01 How the Agent Thinks: Context, Projects, and Outputs14:04 Enterprise Adoption and the Fortune 50016:43 The Pressure of Hypergrowth17:38 Replit's Operating Principles and Culture20:05 The Vision: A Billion Software Creators22:27 Building on Mobile: What's Possible From Your Phone26:22 What's Next for AI Agents in the Next 12 to 18 Months28:26 Advice for Builders: Just StartMore on Aman:https://www.linkedin.com/in/aman-mathur/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Today’s conversation with Mitchell Jones covers what most founders miss: survival comes first. We unpack second-time founder advantages, fundraising psychology, and long-term trust with investors. And we go deep on why AI agents demand a new payments infrastructure.Mitchell Jones is a fintech founder building Lava Payments, a modern payments infrastructure company focused on enabling faster, more flexible capital movement for businesses. Before launching Lava Payments, Mitchell Jones co-founded Lendtable, a fintech platform designed to help employees access capital to participate in employer-sponsored benefit programs.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:00 Mitchell Jones’ Background and Founder Journey2:02 What Mitchell Learned From Building Lendtable6:41 The Three Biggest Founder Lessons From His First Startup8:24 The Pros and Cons of Being a Second-Time Founder13:19 Why Mitchell Is Building Lava and Betting on AI Payments18:57 How Lava Helps AI Companies Track Usage and Monetize20:27 Fundraising Advice: How to Think Like a VC25:17 What Really Gets an Investor to Say Yes29:44 Why Founders Should Pitch Believers, Not Convince Skeptics32:01 Why Trust Comes Before the Transaction35:24 Mitchell on AI Applications, AGI, and the Future of Companies41:18 Great Man Theory and the Future of AI44:40 OutroMore on Mitchell:https://www.linkedin.com/in/mitchell-jones-333559a2More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Today’s conversation with Kate Ryder explores what it takes to build a category-defining company in one of the most complex and regulated industries in the world, healthcare. We discuss scaling Maven into a $1.7B company serving over 28 million members globally, the role of timing, resilience, and storytelling in building generational businesses, and how AI is beginning to transform care delivery, operations, and patient outcomes. Kate Ryder is the Founder and CEO of Maven Clinic, the largest virtual clinic for women’s and family health. Under her leadership, Maven became the first unicorn in its category, partnering with over 2,000 organizations across 175+ countries to support fertility, maternity, pediatrics, and menopause through a modern, digital-first healthcare platform. Our podcast is sponsored by Gunderson Dettmer #PoweredByGunderson More on our guest: https://www.linkedin.com/in/kate-ryder-87474933/ More on our host: https://www.linkedin.com/in/jarrid-tingle/ The Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies. Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome. We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Today’s conversation with Ryan Williams explores what it really takes to modernize a trillion-dollar asset class and build through cycles in one of the most competitive markets in the world. We discuss raising over $100M from top-tier investors, facilitating billions in real estate transactions, and the leadership, conviction, and resilience required to earn trust in private markets. Ryan Williams is the Co-Founder of Cadre, a technology platform that has powered $5B+ in real estate transactions and helped redefine access to institutional-quality investments. He is known for his work at the intersection of fintech and real estate, bringing transparency, liquidity, and data-driven infrastructure to historically opaque markets. Our podcast is sponsored by Gunderson Dettmer #PoweredByGunderson More on our guest:https://www.linkedin.com/in/ryanawilliams1/ More on Brandon:https://harlem.capital/team/brandon-bryant https://www.youtube.com/@Wallstreetpaper https://x.com/wallstreetpaper The Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies. Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome. We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Today’s conversation with KJ Sidberry explores where we are in the AI super cycle and why consumer technology may be entering a new renaissance. We discuss how AI could reshape healthcare, education, play, and storytelling, and what Google Ventures looks for in the next generation of founders. KJ Sidberry is a Partner at Google Ventures (GV), where he focuses on consumer and AI-native companies. Previously an investor at Forerunner Ventures, he’s known for his thoughtful perspectives on technology, culture, and the future of consumer products. Our podcast is sponsored by Gunderson Dettmer #PoweredByGunderson Timestamps: 0:00 Intro + why KJ is one of the top voices in consumer AI 1:52 Why consumer is due for a renaissance 3:28 How AI democratizes access in healthcare and therapy 5:18 AI should make us more human, not less human 8:03 Lessons from Oura Ring and the future of consumer hardware 12:45 Why wearable tech is becoming identity and status 13:42 How AI could transform education 16:56 Personalized learning and better employment outcomes 19:35 Alpha School, AI learning, and new education models 21:39 The future of play: AI toys, companions, and parenting 26:01 Why storytelling may be one of AI’s biggest categories 30:34 What Google Ventures looks for in founders 33:10 How GV supports founders after investing 34:19 Where we are in the AI super cycle 36:45 The behavior changes AI may already be driving 37:26 Why joy and delight matter more than productivity alone 38:31 Founder advice: build with velocity and scratch your own itch 41:40 Outro More on KJ: https://www.linkedin.com/in/kjsid/ More on Brandon: https://harlem.capital/team/brandon-bryant https://www.youtube.com/@Wallstreetpaper https://x.com/wallstreetpaper The Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies. Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome. We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.