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.