ShareFile, Levitate co-founder Jesse Lipson: Trust yourself

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.

In this episode of the Sit Down Startup podcast, Lipson opens up about his founder experience, including:

• Acquisitions—these are a rollercoaster. Deals can take months to finalize, but it’s important to stay focused on the business and your customers.
• Do the hard work—no surprise to hardworking founders, but attracting customers doesn’t happen overnight. Being prepared to go the extra mile to improve the product or dig deeper into customer pain points.
• Be data-driven—it can be time-consuming and expensive to test and measure, but it’s hard to understate the value of this data, which includes consumer insights and feedback.

“Finding the balance between taking feedback and staying true to your vision is one of the hardest things entrepreneurs have to do.” Jesse Lipson, 2x co-founder of Levitate and ShareFile

A key takeaway from the episode is knowing when to ignore “smart” advisors in favor of pursuing your own path. Lipson recalls facing skepticism from experienced advisors who, at times, questioned his business strategy. Still, Lipson remained committed to building the product in his vision and growing a customer base, even when it went against conventional wisdom. It’s a delicate balance to strike, and you don’t want to miss how Lipson navigated his inner and outer critics.