Bootstrapped to nearly $100M exit to Citrix; Jesse Lipson; knowing when to ignore the “smart” advisors vs. just building

Jesse Lipson initially thought he would become a philosophy professor — until he took a job with a startup that changed his career path. After founding his first company Sharefile in 2005, he sold it to Citrix in late 2011 for almost $100M. And in October 2017 he established Levitate, which helps relationship-based businesses keep in touch with clients in a more personal and authentic way.

This entrepreneur offers a few insights from his career to date:

• Acquisitions are a rollercoaster. Deals can take months to finalize and it’s important to maintain focus while they’re ongoing.

• Do the hard work. Attracting customers doesn’t happen overnight, so be prepared to go the extra mile.

• Be data-driven. The benefits of testing and measuring everything outweigh the costs.