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  • Writer's pictureCreative Return


Updated: May 28, 2023

Jason VandeBoom has bucked the Silicon Valley trend of raising money wildly and living to “fail fast”. Jason is the founder and CEO of ActiveCampaign. He recently raised a $100,000,000 Series B financing for his company, but unlike so many software entrepreneurs, he has been building his same business for over 15 years.

In this episode, Jason shares with us why he chose a measured approach to grow ActiveCampaign. For him, valuation figures do not correlate with validation.

Instead, the customer experience is his North Star, so much so that he still reads customer reviews to keep his finger on the pulse of the company. Jason and his service-minded approach to business is truly inspiring. We loved having him on the show. Be sure to tune in.



  • ActiveCampaign’s unusual approach to raising capital and why they did it ‘slowly’.

  • Why Jason does not regret the steady, measured growth of ActiveCampaign.

  • The role that Jason’s fine art background has played in the company building.

  • ActiveCampaign’s team composition and annual revenue.

  • Why customer usage is a metric more important than valuation to Jason.

  • Jason’s take on investor relationships and the importance of ‘backchanneling’.

  • Find out why a lot of optionality is so vital to Jason and how it relates to capital raising.

  • How ActiveCampaign’s investors have dealt with giving a timeframe.

  • Learn how Jason is handling culture with a rapidly expanding company.

  • Scaling yourself: What Jason is doing to grow as a founder as the company grows.

  • Lessons Jason learned from raising capital and moving through the discomfort.

  • Jason’s advice for entrepreneurs: Try to create a path that’s yours and yours alone.

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