Winners Welcome Podcast, Episode 9 with Charles Yoo-Naut, Founder and CEO of Rain.

Charles Yoo-Naut didn’t set out to rebuild global payments. He was trying to fix a wire transfer.

In 2021, Charles and his co-founder were building SignAndWire, a simple tool to help founders raise money without cobbling together DocuSign and a bank wire. Then they tried to actually move the money. What should have been straightforward turned out to be slow, expensive, and dependent on a web of banking infrastructure that hadn’t meaningfully changed in decades. That friction became the thesis for Rain.

Charles is a two-time founder who sold his first company, Playbook HR, to Intuit in 2015 after saving $50K at Microsoft to bet on himself. He spent four and a half years inside Intuit learning how to ship products and lead teams before leaving in 2019, refreshed and ready to take a bigger swing. The company he eventually built, Rain, is now a $2 billion stablecoin payments infrastructure platform that has raised over $300 million, secured Visa Principal Member status, and scaled from under 20 people to over 120 in a single year.

In this episode, Charles breaks down the idea maze philosophy that led to Rain, the Christmas Day USDC transfer that made the opportunity clear, what it took to become one of the few non-bank Visa Principal Members in the world, and how Rain raised three rounds in 12 calendar months by building a business that didn’t need to ask.

This episode is brought to you by Gunderson Dettmer, the number one law firm in venture capital globally. #PoweredByGunderson

Watch the full episode on YouTube and subscribe to Winners Welcome for more conversations with founders, operators, and investors building what’s next.

About The Winners Welcome Podcast

The Winners Welcome Podcast brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.

About Harlem Capital

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.

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