ShareFile, Levitate co-founder Jesse Lipson: Trust yourself
From bootstrapping through acquisition, Lipson advises balancing conventional wisdom with entrepreneurial spirit.
Last updated June 7, 2023
There’s a lot of advice and conventional wisdom out there for startup founders. But one of my favorite pieces of advice is more of a reminder: trust the entrepreneurial spirit that got you in the game in the first place. Perhaps appropriate from a would-be philosophy professor turned 2x startup founder.
Self-taught programmer, developer, and designer Jesse Lipson founded Sharefile in 2005 as a cloud-based answer to clunky FTP sites. He sold the company to Citrix in 2011 for almost $100 million, having bootstrapped the company—no outside funding—until it was acquired. In 2017, he founded Levitate, an AI-driven platform that helps businesses stay close to their customers. There, he delved into fundraising—they raised $14 million in Series C in 2023, and boasts more than 3,000 small business customers.