MIT to Millions – AI & Entrepreneurship with 3x Startup Founder & Pilot CEO Jessica McKellar | EP4
Автор: iStart Valley
Загружено: 2025-08-20
Просмотров: 216
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In this episode of iStart Insider, hosts Hannah and Tanvee sit down with Jessica McKeller — founder and CEO of Pilot, the largest startup accounting firm in the U.S. with over $200M in venture capital funding. A three-time startup founder, MIT alum, and former Python teacher for incarcerated students, Jessica shares her unique journey from building software and selling companies to Oracle and Dropbox, to scaling Pilot as a tool to empower small businesses nationwide.
Jessica reflects on everything from early exposure to computers through music, to overcoming imposter syndrome, building strong co-founder relationships, and how she thinks high schoolers can navigate a future shaped by AI. She also opens up about motherhood, the importance of values-driven leadership, and how her time at MIT shaped her approach to entrepreneurship.
Whether you're dreaming of launching your own startup or wondering how to align your career with your values, Jessica’s story is packed with hard-earned insights, honest advice, and big-picture reflections you don’t want to miss.
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