Brian York left Colombia when he was two weeks old, adopted by a US family and didn’t come back until 2009. Although he grew up south of Boston, Brian never forgot his Colombian heritage and always planned to travel back to try to meet his biological family. Most people would probably go on vacation to Colombia to accomplish that mission, but not Brian. Instead, he started several businesses in his birth country (including current venture, Liftit), raised millions of dollars, and began supporting and angel investing in Colombian startups. Brian is now tackling one of Latin America’s most pressing challenges, logistics, and is already operating in almost every major city in the region. Brian has watched the Colombian ecosystem evolve over the past decade and is long on the future of the region. In this episode of Crossing Borders (recorded in Liftit’s Bogota offices), I sat down with Brian to discuss learning from failure, transitioning from the corporate world to startups, starting a business in Latin America, and the Mexican and Colombian investment ecosystems. Check out the rest of this episode to hear from an entrepreneur who exemplifies doing business across borders. “I always knew I didn’t belong behind a desk.” Brian York is a lifelong entrepreneur who started his first business in high school. Ever since, he knew he wanted to own his own company and control how it would grow. Despite spending a few years tethered to a desk as an accountant, it didn’t take long for Brian to make his way to Silicon Valley with his first (of many!) business ideas. Check out the rest of this episode to hear how Brian went from CFO on Chris Sacca’s fund, Lowercase Capital, to becoming a tech entrepreneur in Silicon Valley before his 30th birthday. Learning from first failures Brian’s first tech startup had a $3M runway and still failed...hard. It may have been a rude awakening, but that experience trained Brian to be a faster, smarter, and better entrepreneur. Among the biggest lessons learned: never be a solo founder. It’s just too hard to go it alone. As a serial entrepreneur, Brian knows what it takes to get a company off the ground and raise money in Latin America and the US. Listen to this episode to hear his advice for founders; it’s equally applicable for people on their first business and those who are on their fifth! Initial Traction: Building Liftit on Facebook and Whatsapp Aspiring founders often think they need a lot of money to test their ideas before a business can get off the ground. In this episode, Brian explains how he got the first three customers for his Colombian startup, Liftit, spending just $5 a day. Everyone’s vision for fixing the world can really be boiled to one testable detail, says Brian. Find that detail, build it, and figure out if anyone is willing to pay you before you raise money. Increasingly VCs worldwide expect to see proven traction from entrepreneurs before investing in a startup. Check out this episode to hear Brian explain how he raised $16.5M from across Latin America for a company he originally ran through Whatsapp. Brian York’s current startup, Liftit, is active in all of Latin America’s biggest markets, and it’s growing fast. Brian has faced advantages and disadvantages that few other Latin American founders have seen, yet his advice applies to entrepreneurs across the globe. Tune in to this episode of Crossing Borders to hear how Brian scaled a business across Latin America to solve one of the region’s most entrenched problems: shipping logistics. Show Notes: [1:48] - Nathan introduces Brian [2:08] - Founding Liftit and the business today [3:05] - Why Liftit was founded in Bogota [4:13] - Did you always know you were from Colombia? [5:13] - Brian’s first business at age 15 [9:06] - What pushed you to jump into tech entrepreneurship? [10:40] - Creating the first “Facebook for sports fans” [12:22] - Raising 3M for a business with no business model [13:16] - What to do with zombie companies in LatAm? [14:20] - Lessons learned from first company [16:12] - The next two startups [19:48] - How Brian York has evolved as an entrepreneur [20:58] - How did you choose Liftit? [22:47] - Why outsource development? [23:54] - Why outsource to LatAm? [27:58] - How did you get Liftit started? [30:20] - How did you know it would be a real business? [32:30] - Planning an international expansion [33:40] - Choosing investors [36:00] - Biggest difference raising in Colombia vs. US [38:30] - Differences between Colombia and Mexico [40:20] - Why last-mile delivery in LatAm? [44:30] - How are opportunities for entrepreneurs changing in LatAm? [47:17] - Brian’s advice to his younger self [49:26] - What’s next for Liftit? Resources Mentioned: Brian York on LinkedIn Angel Celis Botto Felipe Betancourt Celis Y Combinator Startup School Liftit Bassin Ventures