From a reluctant turn in school theater to founding Northpond Ventures, Mike Rubin has kept returning to the same question: how do you make yourself useful?

After a decade helping Chegg scale, John Fillmore returned to the oldest problem in higher education: how to make a classroom feel more like the work waiting outside it.
Sara Leoni is the founder and CEO of Ziplines Education, a Bay Area career accelerator that partners with 30-plus universities to deliver industry-recognized certificate programs in fields like AI, project management, and digital marketing. A former Division I softball player at UNLV and ex-CEO of the $50M course-materials company Rafter, she raised a $6.4M Series A in 2023-2024 to help close the digital skills gap and has helped more than 20,000 adult learners retool their careers. She frames learning as a zipline: intimidating, exhilarating, and continuous, with a clear start and a clear landing.