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Ten years ago I was living in Taipei as a postdoc at ASIAA. Early the following year I left to try my luck in the field of data science, which involved studying, taking on side projects to build a portfolio, and applying for jobs. Ultimately, I took a job in the field of online education. Since then I've worked with three different companies to create courses focused on artificial intelligence and machine learning that serve thousands of learners worldwide. In this talk I will include a brief summary of my work in astronomy followed by stories and learnings from my transition into the world of silicon valley ed-tech companies.