

56. How a College Basketball Player Became an Ed Tech Founder with the Co-Founder & COO of Learn to Win, Sasha Seymore
Sasha Seymore is a co-founder and the COO of Learn to Win, an education technology company based in Redwood City, California, that improves training and onboarding for commercial enterprises, the Department of Defense, and athletic teams and programs. Sasha is also a reserve intelligence officer for the US Navy serving with the Defense Innovation Unit (DIU), helping the U.S. military make faster use of emerging commercial technologies.
Prior to Learn to Win, Sasha worked as a consultant for McKinsey & Company and played professional basketball in Europe. Sasha received an MBA from Stanford as a Knight-Hennessey scholar, an MA from Queen's University Belfast as a George Mitchell Scholar, and a BA from the University of North Carolina, where he was a Morehead-Cain Scholar, Senior Class President, and Scholar-Athlete of the Year on the men's basketball team. Sasha serves on the National Leadership Council for the Positive Coaching Alliance and was named to the 2022 Forbes 30 under 30 list in Education.
Sasha joins Brendan to discuss:
- How he balances his career in the Navy Reserves with being a startup founder
- How Learn to Win was born from his experience playing college basketball
- The nuances between the military, startups, and careers at larger companies
- His advice for getting the most out of your career post-military
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