Podcast: Embed
What does it take to grow a digital marketing agency from nothing to $20M in revenue, and then exit successfully?
On the 7 Figure Agency Podcast, Josh Nelson sat down with Jason Hennessey, founder of Hennessey Digital, to unpack his journey. From stumbling into SEO while running a DJ business to becoming a thought leader in legal marketing, Jason shares hard-earned lessons on specialization, scaling, and preparing for a strategic exit.
Accidental Beginnings in SEO
Jason didn’t set out to start an agency. While running a DJ business in college, he built his own website and taught himself SEO. Years later, a speaking engagement on SEO unexpectedly opened doors with attorneys in the audience, many of whom became his first clients.
That single presentation sparked what would grow into a multimillion-dollar agency focused on the legal niche.
Why Choosing a Niche Matters
Rather than spreading himself thin across multiple industries, Jason leaned into the legal vertical. Attorneys introduced him to peers, invited him to conferences, and referred business. Over time, Hennessey Digital became synonymous with legal SEO.
The takeaway? Authority comes from focus. By becoming world-class in one niche, you can dominate faster than by chasing opportunities everywhere.
Premium Pricing and Case Studies
Jason made an intentional decision early on: instead of undercharging, he priced his services at a premium to ensure he had the resources to deliver real results.
This allowed him to:
- Create powerful case studies that became proof points for future clients.
- Set a new market standard (competitors even thanked him for raising the bar).
- Attract clients willing to invest in growth rather than bargain-shop.
Authority Building Through Content and Branding
To accelerate growth, Jason leaned into authority marketing:
- Speaking engagements at legal industry events
- Publishing a book (“Law Firm SEO”), which generated leads and positioned him as the expert
- Consistent personal branding that drove inbound leads
This approach meant Hennessey Digital never had to rely heavily on cold outreach. Most clients came inbound, pre-sold on Jason’s expertise.
Scaling With the Right Team
As the agency hit $3M+ in revenue, Jason realized he couldn’t do it alone. He brought in a COO, CFO, and salespeople. He also engaged Cameron Herold as a coach, which helped double revenue from $4M to $8M in just one year.
Key lesson: hire leaders and delegate. Freeing himself from day-to-day tasks allowed Jason to focus on vision, branding, and strategic growth.
Preparing for Exit
By the time Hennessey Digital hit $20M in annual revenue, Jason began planning for a potential exit. The focus shifted from rapid growth to profitability, since EBITDA drives valuation.
When the right private equity partner approached, the fit aligned on three priorities:
- Clients
- Team
- Founder goals
Jason sold to Herringbone Digital but stayed actively involved as CEO and board member. Instead of “cashing out and walking away,” he gained access to more capital and resources to keep building.
Jason’s Advice for Agency Owners
Jason’s biggest lessons include:
- Specialize in a niche to dominate faster
- Charge enough to deliver real results
- Invest in authority building (book, speaking, personal brand)
- Delegate and hire leaders so you can scale
- Focus on profitability if you want to position for an exit
And his daily mantra? “Wake up and take two actions that create a future that wouldn’t exist otherwise.”
Conclusion
Jason Hennessey’s story is proof that with focus, authority, and smart scaling, an agency can go far beyond expectations. Whether you’re aiming for $2M, $10M, or preparing for a sale, his journey offers a roadmap.
👉 Watch the full conversation with Jason here: https://youtube.com/live/7JCJQzkUX00
