Standing Still Won't Get You There: Leverage the Outsider Advantage to Become an Insider w/ Brian Requarth, co-Founder of VivaReal and Latitud

Host Ian Hathaway interviews Brian Requarth, co-founder of VivaReal and Latitud, about building one of Latin America's leading real estate marketplaces and later creating a founder support system for the next generation of entrepreneurs in the region. Brian traces his path from Sebastopol, California, to Bogotá, Colombia, where a one-way trip became six years, a language school helped pay the bills, and a chance meeting in an immigration office led to his first co-founder. He explains how the 2008 financial crisis pushed him to rethink the business, why Brazil became the market for VivaReal, and what it took to build a company through cold calls, investor rejection, bootstrapping, and $87 in the bank. They cover scaling VivaReal from a scrappy startup to more than 500 employees, learning the CEO job in real time, stepping back from the role for family, negotiating the Zap merger, and selling the company to OLX for roughly $550 million. Brian also discusses the post-exit search for purpose, the origins of Latitud, why founders need community earlier than they usually get it, the rise of globally ambitious Latin American founders, San Francisco's role in accelerating learning, and how outsiders can turn their perspective into an advantage.   Show Notes:   (06:05) Teaching English And Meeting A Co-Founder In Immigration (11:00) Pivoting After The 2008 Financial Crisis (12:05) Engineering Serendipity (15:00) Cold Calling Brazil And Bootstrapping VivaReal (18:15) Scaling From Startup To 500 Employees (19:10) Learning Fast As A First-Time CEO (21:20) Stepping Back From The CEO Role (24:30) Negotiating The Zap Merger (28:00) Lessons From A $550M Exit (30:30) The Origins Of Latitud (36:45) Latin American Founders Building Globally (39:15) San Francisco And The Velocity Of Learning (42:15) Latin America's Founder Mindset Shift (47:10) Beyond The Bio with Brian Requarth     ✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC ✅ Guests: Brian Requarth - Co-Founder, VivaReal & Latitud   Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2026, Bridge Five Ventures, LLC, All rights reserved.   Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.