Jason Hennessey: Selling an SEO Agency to Private Equity

Are you hiring for senior Search Market talent? Let's chat: https://www.searchforhire.com/contact/ Jason Hennessey built Hennessey Digital for over a decade, then sold it to private equity, and stayed. In today's episode, I go behind the scenes of the deal with Jason: the two-year run-up, getting EBITDA from break-even margins to $4.7M in a single year, why he spent more time negotiating the LOI than anything else, and how he called six founders who'd sold to PE and asked each one the same question: "How did you get screwed over?" Jason is still CEO of Hennessey Digital, now part of Herringbone Digital (the Trinity Hunt-backed platform) that acquired $25M in EBITDA in its first year and sits at roughly $110M top line today. He's also on the buy side now, and shares exactly what he looks for in the agencies they acquire. What you'll learn: – The moment to pivot from lifestyle business to sellable asset – What actually changes in the business when you decide to sell – How to structure an earnout so you don't leave growth on the table – Why clean financials are where most deals die, and how to avoid it – How a personal brand earned Jason a higher multiple – The communication playbook for telling your team, your clients, and the market Connect with Jason Hennessey:   / jhennessey   Connect with Josh Peacock:   / joshpeacock-searchforhire   Work with Search for Hire: 📞 Book a call with Josh: https://www.searchforhire.com/contact/ Timestamps 0:00 – Intro 1:49 – The deal: Trinity Hunt, Herringbone Digital, and staying on as CEO 4:01 – The pivot to sellable asset at $3.5M 7:04 – Building to sell vs. building to grow 8:52 – Getting EBITDA to $4.7M 10:56 – The earnout that made it work 13:40 – Advice from 6 founders who sold to PE 15:10 – Why the LOI matters more than the purchase agreement 16:03 – Where most agency deals die 18:17 – How a personal brand earned a higher multiple 21:12 – Telling the team, the clients, and the world 27:09 – Resolving the $150K clause dispute 29:26 – What Jason looks for in agencies now 32:48 – SEO, AI search, and where the industry is heading 37:22 – YPO, business coaches, and why every CEO needs a "no person" 40:27 – The cold email that changed everything 44:10 – From cleaning houses with mum to this 46:16 – What's next for Jason Hennessey 48:18 – Work with Search for Hire