[Podcast] Inside the Agency Acquisition: Why Hennessey Digital Joined Herringbone
If you’ve ever wondered “Would I ever sell my agency?”, this week’s episode of the Deep Specialization™ Podcast is a must-listen.
I sat down with Jason Hennessey, founder of Hennessey Digital, and Raj Ramanan, CEO of Herringbone Digital, for a candid conversation about:
- Building an agency with 10-year staying power
- Saying no to multiple offers and yes to the right one
- Private equity that’s actually founder-first
- The real playbook for communicating a sale to your team and clients
- Why verticalization isn’t just a strategy, it’s the future
Jason opens up about what made this deal different, and Raj shares the thesis behind what Herringbone is building: a PE-backed model designed for agency founders, not against them.
This isn’t theory. It’s real numbers, real people, and real leadership.
If you’re serious about scaling and staying true to your values, this episode will give you clarity and insight most people never get until it’s too late.
Know an agency owner who's been weighing exit options? Forward this along. They'll thank you.
🎧 Listen to the episode now:
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–CQ
