Inside Rain: Three Rounds, Ten Months, $250M Series C

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 info@harlem.capital or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.