After firm’s $50M sale, co-founder was done with startups. Then AI pulled him back in.

Santiago Jaramillo has been the subject of – or at least mentioned in – 44 articles in the Indianapolis Business Journal, including several columns he wrote about entrepreneurism. The stories largely appeared between 2013 and 2021, while he was building, running and exiting two Indianapolis-area tech companies. After the second firm, known as Emplify, was acquired for $50 million in 2021, Jaramillo had a severe case of burnout. He went on an extended sabbatical, planning to forego any future forays into founding startups.   Then ChatGPT dropped. Suddenly entrepreneurs and executives had widespread access to artificial intelligence tools, and Jaramillo quickly saw their potential for transforming businesses and the workflows of their employees. The pull eventually proved too great. Jaramillo co-founded a firm named Pragmatico to help companies make the leap into AI in a way that sticks. In this week’s podcast, Jaramillo takes us on his entrepreneurial journey, which began in Colombia, South America, where he narrowly avoided a kidnapping. His career took turns through Florida, Indiana and Australia before settling back in the Hoosier state. Jaramillo also discusses why he decided to get back in the game, the reasons why many firms have trouble adopting AI and why the technology shouldn’t be set loose without human judgement as a guide.