Practical Founders Podcast

#8: Bootstrapped to $100M Exit with Just One Employee – Jeremy Clarke of WebMerge

Jeremy Clarke created, grew, and sold his software company in a most unusual and successful way:

He grew WebMerge to $5M revenue by just himself for 6 years before hiring his first and only employee, a strategic sales rep. It’s an incredible “bootstrapped unicorn” success story that ultimately was worth $100M when he sold WebMerge in 2019.

WebMerge was an online service that automates document creation to automatically fill in any documents with merged data from any source. WebMerge automatically generates PDF and Microsoft Word documents. Think of it as “mail merge for the web.”

Jeremy’s first employer, Formstack, ultimately acquired WebMerge to bring Jeremy back to the Formstack team and renamed the product to Formstack Documents.

“So I just did an experiment over the years. For six years in a row, I continued to raise prices. Then I finally hit the limit of customers feeling like this is a little too expensive and so I stopped. In the end, the $19 plan was 50 bucks. And our enterprise plan was $99 and now it was $1000 So it went up a lot.”

In this episode, Jeremy explains:

  • How he came up with the idea and pitched it to his employer before building it on his own
  • How he grew revenues to $1M ARR before he quit his day job as a full-time software programmer
  • What it was like to grow a $5M+ ARR SaaS business without  any other employees or Slack groups or constant meetings
  • How many times he raised prices annually before he found the right price
  • How he grew awareness and conversion efficiently by integrating with other apps and appearing in their add-on marketplaces
  • What it was like to sell his company to a private equity (PE) buyer in two phases

WebMerge Company Facts

  • Founded: 2011
  • Software Type: Automated document creation using merged data
  • Funding: Night job for 4 years before he quit when his startup was wildly profitable. No outside funding.
  • Acquisition: Total of $100MSold to private equity buyer that also had just purchased Formstack, his previous employer. First payout of $30M in 2019, second payout of $70M after.
  • Number of Employees: Hired his sole employee after 5 years!
  • Location: Los Angeles area, California


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Greg Head recorded this on episode on August 12, 2022 for the Practical Founders Podcast see all of the episodes.

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