Selling Your Agency? Lessons from Hennessey Digital & Herringbone
Corey Quinn
Founder, Deep Specialization™
Jason Hennessey and Raj Ramanan share a candid conversation on building an agency with staying power, saying no to offers, and why verticalization is the future.
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
Frequently Asked Questions
What made Jason Hennessey say no to multiple offers before eventually saying yes to one?
A distinct difference in that specific deal, discussed directly in the episode, that separated it from the other offers he'd previously turned down while building Hennessey Digital.
What does "private equity that's actually founder-first" mean, according to Raj Ramanan?
A PE-backed model built specifically for agency founders rather than against them, the core thesis behind what Herringbone Digital is building as an alternative to more typical private equity approaches.
Why does communicating a sale to your team and clients require a real playbook?
Because how a sale gets communicated internally and externally can shape trust and continuity through the transition, a topic covered directly in the episode as part of the real, practical realities of an agency sale.
Why is verticalization described as "the future," not just a strategy?
Because it's framed as a fundamental direction the agency world is heading toward, not simply one tactical option among many, a perspective shared by both guests based on their own experience building specialized agencies.
Who is this episode most relevant for?
Agency owners who've been weighing exit options or wondering whether they'd ever sell, offering real numbers, real people, and real leadership insight rather than theoretical advice about agency exits.
About Corey Quinn
Founder, Deep Specialization™
Corey helps founder-led agencies scale through Deep Specialization™ and programmatic M&A. Former CMO of Scorpion ($20M to $200M). Author of "Anyone, Not Everyone."
