AGENCY GROWTH CLUB
Jason Hennessey (Hennessy Digital ) on Selling an SEO Agency to Private Equity
Guest: Jason Hennessey
Guest: Jason Hennessey
Jason Hennessey did not view the Hennessy Digital transaction as an exit from the work.
He describes it as “selling in”: taking some capital off the table while reinvesting into Herringbone Digital, staying CEO of Hennessy Digital, and helping build a broader platform.
In this Agency Growth Club conversation, Jason explains the operational choices that made Hennessy Digital more sellable, why he prioritised profitability and clean financials, how he researched a potential buyer, the role an earnout played in bringing forward the deal, and why client and team communication mattered after the transaction closed.
The chapter labels and timestamps below are taken from the official YouTube chapter list and cross-checked against the supplied transcript.
Jason frames the transaction as a change in platform, not a retirement. A private-equity group approached Hennessy Digital to help accelerate growth that was already working. He says he took “some chips off the table,” reinvested a meaningful portion into the new platform, remained CEO of Hennessy Digital, and joined a broader effort to improve the product across sister agencies.
The buyer Jason names is Trinity Hunt, with Herringbone Digital as the platform. He says Hennessy Digital was the second acquisition and that the platform focuses across legal, home services, elective medicine, and dental. Those details should be understood as Jason’s account from the recording, not a general endorsement of one transaction structure or buyer model.
“I like to say I didn’t sell out, I sold in.” — Jason Hennessey
Jason’s decision rule was ordered rather than purely financial: any potential deal had to be good for the team first, good for customers second, and good for him third. That order explains why he says some prospective buyers may have offered more money but did not match his views on culture or client outcomes.
Jason says the real decision to build a sellable asset came when Hennessy Digital was around $3.5 million in top-line revenue. His concern was not that entrepreneurship had stopped working; it was that an entrepreneur can become the bottleneck after creating the early momentum. He describes entrepreneurs as good at pressing the “quick start” button but not automatically prepared to scale a business without more capable leaders, systems, and decision-making layers around them.
His answer was expensive on purpose. Jason brought in a COO, then recruited a CFO and CTO, while building layered management, clearer goals, accountability, systems, and processes. He says the business moved from roughly $3.5 million to $8 million in one year after those investments, but he also stresses that rapid growth became uncomfortable at times. At a later stage, he recalls low margins and a possible need to move personal funds to cover a third pay period.
The lesson is not simply “hire executives early.” It is to recognise the point at which founder improvisation becomes an operating risk. Senior leadership costs money before it creates compounding capacity, and Jason’s account makes clear that the transition can temporarily put pressure on cash flow and margins.
Actionable advice: Audit whether the founder remains the operating system. If every material decision, client escalation, hiring choice, or process change still needs one person, the business may be accelerating faster than it is becoming scalable. The right response depends on the agency, but the problem should be named before growth exposes it.
Jason contrasts growth mode with sale preparation. In growth mode, he says, founders often reinvest heavily, prioritise expansion, add capacity ahead of demand, and legitimately seek to reduce taxable profit through business spending. When the company is preparing for a potential transaction, the focus changes: the buyer will care deeply about profitability, repeatability, cash flow, concentration, and whether the numbers survive scrutiny.
Jason describes a two-to-three-year runway as the healthiest way to prepare for a sale because an owner selling under pressure loses leverage. Hennessy Digital’s own process moved more quickly than that after Herringbone/Trinity approached about eight months into the company’s profitability thesis. The general preparation principle and the actual timing of this specific transaction should not be conflated.
In Jason’s account, 2024 became a year of profitability discipline. New hires required a business case. Sponsorships and conference spending were examined more carefully. He even cites changing his own travel habits. He says the resulting EBITDA was roughly $4.7–$4.8 million, a recording-time financial claim presented here as his statement, not as audited advice or a valuation benchmark.
“If you’re selling out of pressure, then you lose all your leverage.” — Jason Hennessey
Jason says his original plan was to continue increasing EBITDA and potentially sell later, once Hennessy Digital had reached a higher target. When the prospective buyer approached earlier, he initially declined because he expected the business to grow further. The offer became more compelling when the parties structured an earnout that could compensate him if the business reached the growth targets he was already pursuing.
This is a useful transaction narrative, but not a generic earnout blueprint. The fairness of an earnout depends on many factors the episode does not attempt to resolve: the definition of performance, control after closing, financing, accounting policy, integration decisions, timing, covenants, and legal drafting. Jason’s point is narrower: the deal made sense because the structure recognised anticipated future growth rather than forcing him to surrender all of that value at the point of sale.
Editorial note: Keep language here anchored to Jason’s earnout experience. Do not state that an earnout automatically protects every founder, or that it should be accepted without independent legal, accounting, and M&A advice.
Jason had heard the standard warnings about private equity, so he sought direct, unfiltered feedback from people who had sold businesses. Through YPO, he contacted six peers who had sold to private equity and asked each one the same blunt question: “How did you get screwed over?” He then used those conversations to identify concerns, clarify expectations, and prepare for negotiation.
One resulting choice was to spend significant time on the letter of intent. Jason says he spent more time negotiating the LOI upfront than many founders might, because it established the expectations that would later flow into the purchase agreement. He also says that, more than a year after closing, his experience with this buyer had matched the commitments he believed were made: the leadership team had not been cut and the business had not been “optimised from a spreadsheet” at the expense of culture.
Jason shares one post-close working-capital anecdote. A clause led to different interpretations of approximately $150,000; he says the group split the difference rather than insisting on its preferred reading. That story describes his buyer’s behaviour in one circumstance. It should not be represented as a standard PE practice or a substitute for careful drafting.
Jason says financial diligence is where many deals first lose momentum. A business can make an impressive opening claim, then look very different when a buyer examines the detail. He gives familiar agency examples: revenue concentrated in a single client; personal expenses embedded in the P&L; large distributions that cannot be clearly explained; or reported margins that need to be normalised before a buyer can judge the real earnings.
Hennessy Digital, he says, had strong counsel, a capable CFO, a good CPA firm, and clean books. He took a salary and a regular monthly distribution rather than making ad hoc withdrawals. His COO also took a central leadership role in assembling the information required during diligence. The importance of the point is not that every buyer will view every expense in the same way; it is that surprise and ambiguity erode trust, shift leverage, and create avoidable friction after an LOI has been signed.
Actionable advice: Establish financial discipline well before a transaction is on the horizon. Separate business and personal spending, understand client concentration, document revenue quality, and make sure finance leaders can answer a buyer’s questions with evidence. Consult qualified accounting and transaction advisers for business-specific preparation.
A visible founder can raise a key-person question: what happens if the buyer acquires the agency and the person associated with its credibility leaves? Jason acknowledges that his public profile could have been treated that way by a buyer interested in replacing him. In this deal, he says the opposite was true because the platform wanted founders to remain in place, add capital and infrastructure around them, and lean into their ability to recruit talent and open acquisition conversations.
Jason says his personal brand increased his multiple in this context. He also says that on the buy side, outreach carrying his name can generate a response where an anonymous M&A message might be ignored. The broader lesson is conditional: a founder brand creates value when the buyer’s strategy includes keeping and using the founder’s relationships, credibility, and ability to execute. It can create risk when the transaction thesis depends on removing that person.
“I think in my case, it actually was a benefit. I ended up getting a higher multiple as a result of building a strong personal brand.” — Jason Hennessey
Jason’s communication approach has two distinct stages. During the process, he limited knowledge of the deal to people who needed to contribute to it: initially a small C-suite group, later the CTO and senior client-service leadership as technology and client-list questions required their involvement. His reason was practical. Deals can fail, and prematurely sharing a possible transaction could create anxiety or confusion across the business.
After closing, Jason did not want the company, clients, or market to hear the story through rumour. He prepared a communications plan, told the leadership group, announced the news to the full team, and explained why he was excited, why he believed the transaction supported growth, and why he was staying. He also set up short calls with almost all clients he could reach personally, and created a video for those he could not reach. Then he announced it publicly through press releases and podcast appearances.
The approach reflects Jason’s personal preference for controlling the narrative openly once the facts were final. It is not a universal communications rule, but it offers a useful distinction: confidentiality may be necessary while an uncertain transaction is live; clarity and directness become more valuable once the transaction is complete.
The platform perspective changed Jason’s travel and industry conversations. Instead of attending legal events solely to win clients, he now also considers which agency owners and teams might strengthen the platform. His first filter is quality of operator and service. Because he has spent nearly two decades in SEO and more than a decade in legal marketing, Jason says he knows which agencies consistently show up as credible contenders in law-firm decisions.
He gives two examples from his own account. Blue Shark Digital brought a complementary mid-market product set alongside upper-market legal work. CJ Advertising brought expertise in television and media buying, plus exceptionally long client relationships. Jason also says industry familiarity helps the M&A team avoid pursuing an agency when his experience raises concerns about service or reputation.
The principle is strategic complementarity, not size alone: products, market segments, delivery capability, client quality, founder commitment, and reputation can all change whether an acquisition improves the platform.
Jason does not describe AI search as the end of SEO. He says the arrival of ChatGPT, Perplexity, Claude, Gemini, and Google AI Overviews initially raised the familiar “is SEO dead?” question. As he and his teams studied the systems, his working view became that core SEO remains the foundation: technical infrastructure, authority, citations, and content still matter, while a further layer needs to be learned through new pattern recognition, testing, tools, and specialist hiring.
Jason uses a 70/30 split as a personal framing for this idea: roughly 70% foundational SEO and 30% new AI-search complexity. The episode does not provide research establishing this as an industry-wide benchmark, so it must be written as Jason’s estimate rather than a universal measurement.
He also makes a commercial case for education. In his view, agencies that do not educate clients on AI search leave a space that another agency can occupy. Hennessy Digital is responding through research, new tools and processes, speaking, webinars, and client education. Jason says clients have reported large cases originating from ChatGPT referrals, which he finds encouraging, but that remains a client-reported outcome in the conversation rather than a general performance guarantee.
Jason calls YPO instrumental because a CEO needs a confidential peer group that can challenge assumptions without internal reporting lines or personal relationships distorting the conversation. He says a group such as YPO, Vistage, or EO can provide a place to discuss business pressure, family issues, leadership decisions, and major transactions with people who have faced comparable situations.
Inside the company, he also values a “no person”—someone senior enough to say an idea is good but not the right priority right now. Jason mentions his COO, Scott, in that role. The point is not to block the founder’s ambition. It is to protect focus, prevent the business from chasing every attractive opportunity, and force a choice about what gets built now versus later.
Jason tells a related story about business coach Cameron Herold. He had watched Herold’s TED Talk years earlier, read his books, and later sent a direct email after Hennessy Digital had grown enough for coaching to feel possible. Herold replied quickly, and Jason says the coach’s advice led to decisions including joining YPO, writing books, and hiring an executive assistant. The transferable lesson is to take action toward credible mentors and turn conversations into specific, accountable follow-through.
Jason says the M&A journey is now a major source of energy: identifying deals, bringing businesses into the platform, integrating them well, and improving what clients receive across the agency group. He says his focus is less about checking another financial target and more about building a bigger, better product for legal-marketing clients.
His stated ambition is to make Hennessy Digital the standard against which legal agencies are measured. This is a forward-looking founder goal, not a performance forecast. The episode closes with Jason considering a future book about the M&A experience, following Josh’s suggestion.
Jason Hennessey is the CEO of Hennessy Digital, a legal-marketing agency. In this episode, he discusses Hennessy Digital joining the Herringbone Digital platform backed by Trinity Hunt, while he remained involved as CEO and reinvested part of his proceeds into the wider platform.
He gathered candid input from six YPO peers who had sold to private equity, then used that feedback to clarify expectations early. Jason says this caused him to negotiate the LOI more carefully, rather than treating it as a lightweight preliminary document.
He means he did not view the transaction as walking away from the agency. Jason says he took some capital off the table, reinvested a portion in the new platform, stayed CEO of Hennessy Digital, and participated in the wider growth strategy.
Clean, credible financials. He highlights the risk of overstated results, personal expenses in the P&L, unclear distributions, and revenue concentration that appears only after an LOI is signed. He says Hennessy Digital’s CFO, CPA, and COO helped keep the books and diligence process organised.
No. During the live process, information remained within a small need-to-know group because deals can fail. After closing, Jason announced the deal to leadership and the wider team, called almost all clients he could reach personally, used a video for other clients, and communicated it publicly.
Jason believes SEO remains foundational to AI-search visibility, while a new layer of testing and learning is needed for GEO and other AI-search systems. He uses a 70/30 split as his personal working estimate, not as a universal industry formula, and argues agencies should educate clients as the search landscape changes.
He frames two to three years as the preferable preparation period for building profitability and protecting leverage. His own deal accelerated after a buyer approached around eight months into the profitability plan, so the advice is a recommended runway, not a description of every deal.
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