Send us Fan MailWhat happens when two Cuban-American brothers from a Miami farm get snowed in at college and can't get a decent pizza delivered? They build one of the largest car-sharing platforms in North America — and that's just the beginning.In this episode of Startup Wins, Brandon sits down with Matthew Vega-Sanz, the twin co-founder and CEO of Gail, the world's most advanced AI for financial services. Matthew's story is one of the most jaw-dropping founder journeys you'll hear: a Babson College dropout who launched a peer-to-peer car-sharing app that hit the top 100 in the App Store within 7 days, watched COVID kill it overnight, pivoted into insurtech, scaled that business to nearly $50M ARR, exited in 2024, and is now back building what he believes will be his generational company.What makes Matthew different isn't just the résumé — it's the mindset. A self-described average student with above-average work ethic, he'll tell you straight up that reading obsessively, dreaming irrationally big, and staying maniacally focused on the customer are the real reasons he's still standing while most startups aren't.In this conversation, we get into:The snowstorm that accidentally launched a startup empireHow emailing 532 investors with almost nothing in the bank led to their first yes — and the exact email strategy that workedWhy Matthew believes fintech is the most important form of defense tech in the world right nowThe one thing that keeps him up at night (hint: it's not competition)Gail's bold vision — from Miami strip malls to powering financial services across the solar systemWhy Miami might actually be a competitive advantage over Silicon ValleyMatthew's personal "happy routine" for staying mentally sharp when entrepreneurship gets brutalThis episode is part founder playbook, part love letter to Miami, and part wake-up call for anyone sleeping on the future of AI in financial services. If you've ever wondered what relentless looks like in human form, meet Matthew Vega-Sanz.🎙️ Connect with Matthew: LinkedIn 🌐 Learn more about Gail: meetgale.comDon't forget to subscribe, leave a review, and share this episode with someone who needs to hear that the only way out is through. (Audio) Startup Wins on Apple PodcastsStartup Wins on LinkedInStartup Wins on SpotifyHosted by Brandon Na, Managing General Partner of Good Peoples Ventures