For Starters Season 2 Finale: Jes Lipson On Finding Product-Market Fit (Twice)

Just like that, we have reached the season finale of For Starters Season 2, where host Anil Chawla (with the help of sponsor Robinson Bradshaw) has introduced us to 10 entrepreneurs and guided them on a walk-through of the creation of their startups through the point they reached product-market fit.

Our 10th and final guest is a familiar name to GrepBeat readers: serial entrepreneur Jes Lipson. His current startup is Levitate, a software that helps relationship-oriented businesses stay top-of-mind with their clients and potential clients. Not only did Lipson grow up around his father’s pharmaceutical market research business, but he is also known for having one of the most successful bootstrapped software exits in the region with his previous startup ShareFile, which was acquired by Citrix.

Listen to this week’s episode to hear about Lipson’s process with both of his startups and how this made him the entrepreneur he is today,

Episode highlights:

  • When making the jump to create Levitate after ShareFile’s success, Lipson said that by keeping a list of possible business ideas, it allowed him to have a few options for what he wanted to work on next. Choosing between which one to pursue was one of the hardest parts, he said: “It’s a pretty important choice to make as an entrepreneur. Whatever you choose, you’re going to be spending a lot of time and a lot of money.” (12:40)
  • Lipson said that when trying to understand how he could help businesses on the relationship side of things, he decided to ask businesses firsthand what struggles they were facing: “I just asked them, ‘Hey, what are your top couple of problems as a business?’ without prompting them anything, to see first of all if they came up with anything different than what I had, or also, did anything match.” (19:54)
  • Although Lipson said he was opposed to adding templates to Levitate because they can take away the personalization aspect, he decided that since customers themselves were asking for this change, he would implement it: “I realized that we weren’t going to get the active use if we didn’t create some industry-specific content for them to send, and so that was the next project for us.” (38:30)

To hear more about Lipson’s work with transitioning from ShareFile to Levitate and experience the Season 2 finale of For Starters, listen below! We could not be able to make any of this possible without our sponsor Robinson Bradshaw!