As Start-Up Chile’s first Executive Director, Jean Boudeguer was one of the first people I met when I arrived in Chile. Jean is actually the only ex-Start-Up Chile Executive Director who had not yet appeared on Crossing Borders! Jean faced unique challenges as Start-Up Chile's first director. He had to build the program, yet didn't have any previous governmental experience. After Start-Up Chile, Jean went on to build two fintech startups, Cumplo, a peer to peer lending business and Clay, an accounting software for Latin America. I sat down with Jean on this episode to discuss how he transitioned from a traditional career as a software engineer to working in the government and finally to becoming an entrepreneur. Jean understands the challenges and benefits of working in the private vs. public sector in Chile and what it's like to build businesses. Check out this episode of Crossing Borders to learn from one of the main actors responsible for helping build up Chile’s entrepreneurial ecosystem. We couldn’t ask too many questions working in government Trying to build a startup organization inside of a government agency means fighting bureaucracy. Jean realized that if he was to move quickly to create the infrastructure for Start-Up Chile, he would not be able to fully follow protocol. Despite receiving plenty of negative feedback, his team blasted forward, “breaking some eggs” along the way, but also paving the way for more agile government processes. Jean learned to strike the balance between moving forward rapidly while not breaking too many rules as he built Start-Up Chile. Find out how these skills helped him as an entrepreneur by tuning in to the rest of the episode. If you want to work in Fintech, get ready for the regulations If you thought working at a startup would be less bureaucratic than the government, Jean would probably push you to think again. As a software engineer directing peer-to-peer lending service, Cumplo, after leaving Start-Up Chile, Jean says he needed to know as much about legal issues as about the tech. Fintech is a highly regulated industry and you won’t get far without a lawyer or two. Learn how Jean was able to transition from Start-Up Chile to directing a four-person startup (and growing it to a team of 60!) in this episode of Crossing Borders. Latin America’s tax system is much more advanced than the US Chile’s tax system has been 100% electronic since the early 2000s. With SII (Chile’s version of the IRS) managing all invoices, tax reconciliation is much easier in Chile, and in many other parts of Latin America, than in the US. Clay, Jean’s second startup, uses these simplified tax systems to provided automated accounting services to startups and small businesses. While Chile's tax system is the most advanced in Latin America, Colombia and Mexico aren't far behind, making them ideal markets for Clay’s expansion. Check out the rest of this episode to hear Jean explain how Latin America’s tax systems help startups manage their capital and taxes more efficiently, and how Clay can automate these processes. Jean has played a big role in helping build one of the central programs in Chile’s startup ecosystem, Start-Up Chile. After going on to develop two fintech startups, he has seen entrepreneurship in Chile from every angle. Check out this episode of Crossing Borders to learn more about fintech in Latin America and about the origin story of Start-Up Chile from its first Executive Director.   Show Notes: [1:18] - Nathan introduces Jean [2:19] - What are the accounting challenges for small businesses? [4:24] - Chile’s advanced e-invoicing system [5:05] - Jean’s life story [6:37] - What did you do before Start-Up Chile? [8:20] - What did family think of working for government? [10:30] - Designing Start-Up Chile from scratch [11:56] - Biggest challenge for the first round? [15:44] - Lessons learned about startups while working in Start-Up Chile [17:52] - Deciding to start a company [20:52] - What did you learn going to government to fintech? [22:50] - Why is P2P lending important in Chile and LatAm [24:09] - How did you decide to launch Clay? [29:03] - How can you scale out of Chile? [30:08] - What kinds of businesses use this? [32:43] - Jean’s advice to his younger self [34:51] - What’s next for Clay? Resources Mentioned: Start-Up Chile Cumplo Clay Technologies Todoist Amir Salihefendic on Crossing Borders Amir’s Twitter Jean's Twitter