On September 20th, 2017, Hurricane Maria tore through Puerto Rico, leaving a permanent mark on the Caribbean island and its people. Most budding startups shut down operations for up to a few months as the nation recuperated. One company, BrainHi, doubled down after the hurricane, helping doctors and dentists treat more patients by automating the process of taking appointments through their AI technology. I sat down with BrainHi co-founder and CEO, Emmanuel Oquendo to share his story of how BrainHi survived the hurricane to become the first Puerto Rican startup to get into YCombinator. I’m lucky to be able to work with Emmanuel and Israel as we invested while they were in Parallel 18, Puerto Rico’s equity free accelerator. We discuss Emmanuel’s childhood in Puerto Rico, his desire to solve big problems from the island, and how to leverage his experience in Puerto Rico while pitching in Silicon Valley. Check out the rest of the episode for Emmanuel’s advice for startups who want to reach YC from Latin America and how he has grown BrainHi from Puerto Rico to the world. Human capital is everywhere, but resources are not. Emmanuel characterizes Puerto Rico as an island where “people haven’t had it easy, so we try to support each other through the struggles.” He credits this supportive community as a key to BrainHi’s success. Yet many Puerto Ricans, especially those with higher education, end up leaving the island in search of more opportunity in the US. It’s not that the US has better talent, says Emmanuel. It just have more resources. Listen to this episode to hear how Emmanuel came to realize Puerto Rico’s strength while he was working in Boston and how he became obsessed with solving the island’s brain drain problem. More of an evolution than an “aha” moment. BrainHi was not the result of an epiphany that hit Emmanuel one day. After becoming fascinated with AI technology, he began creating custom chatbots and soon found they sold particularly well with one customer niche: doctors. Yet as they participated in Parallel18, Puerto Rico’s government accelerator, Hurricane Maria left the country paralyzed. BrainHi got quickly back on its feet, selling to doctors who need the technology to keep up with demand. Listen to this episode to hear Emmanuel and his team’s inspirational story of getting going again a few days after the hurricane and how BrainHi’s sales-first approach helped them grow in the Hurricane’s aftermath. “It felt like the world exploded.” On a night in San Francisco, surrounded by Puerto Rican entrepreneurs, BrainHi became the first Puerto Rican startup in Y Combinator. After that, it was back-to-back office hours with the accelerator’s entire network. Emmanuel’s advice to startups in YC: ask every question you can think of. No one will tell you how to build your business, but they will answer all your questions.   Check out this episode of Crossing Borders to hear more of Emmanuel’s advice for Y Combinator, including interview strategies and how to pitch to VCs in Silicon Valley if you are from Latin America.   The story of BrainHi, from bootstrapped business to YC graduate, is one that many entrepreneurs dream of. Emmanuel’s passion for combating brain drain in Puerto Rico by helping build the local ecosystem is contagious and his energy has helped drive BrainHi to success. I hope you enjoy this episode of Crossing Borders as much as I did! Show Notes: [1:40] - Nathan introduces Emmanuel [2:07] - Where is BrainHi today? [3:33] - Emmanuel’s childhood in Puerto Rico [4:54] - What problems were you trying to solve in high school? [6:10] - What makes Puerto Rico so special? [8:00] - The education system in PR [9:26] - The decision to leave Puerto Rico [12:10] - How to take advantages of opportunities when they arise [13:36] - What made you decide to go back to PR? [16:08] - Quality of life in Puerto Rico vs. Silicon Valley [17:52] - Why BrainHi? [20:29] - Meeting his co-founder, Israel [22:30] - Bootstrapping the company with just $40K [25:06] - Getting to the first 30 clients [26:50] - Why Parallel18? [28:29] - How Hurricane Maria changed Puerto Rico [31:20] - Raising 100K preseed with friends and family [32:29] - Getting into Y Combinator [34:43] - Preparing for the YC interview [38:20] - How to make the most of YC [40:30] - Making sales in the Bay Area [42:09] - Emmanuel’s advice to his younger self [43:44] - Recommended resources [44:40] - What’s next for BrainHi?   Resources Mentioned: Emmanuel’s cofounder, Israel Figueroa BrainHi Parallel18 Y Combinator Y Combinator YouTube Channel My blog on Y Combinator Startup School   Crossing Borders: Sebastian Vidal Crossing Borders: Abartys Health   Paul Graham Close IO Blog