For the first three years of Hennessey Digital, Jason Hennessey was the business. He knew every client. He touched every deliverable. He was the closer, the strategist, and the quality control system. Revenue grew, but it grew at the speed of one person.
Then Jason made a decision that changed the trajectory of the agency: he brought in a COO.
That COO recruited a CFO and a CTO. Within a year, revenue went from $4M to $8M.
The Constraint Founders Don’t See
Most agency founders are so deep in the day-to-day that they can’t see the pattern clearly. They’re the best practitioner in the building. They know the work better than anyone, and because they’re capable of doing everything, they do everything.
This creates what Jason calls the “lifestyle business” trap. The agency grows, but it grows at the founder’s capacity. Every decision, every client relationship, and every strategic initiative runs through one person. The ceiling isn’t the market. It’s the founder.
The counterintuitive truth is that the most capable founders are often the biggest constraints on their own businesses. Their competence becomes a bottleneck because they can’t let go of the work on which they built their reputation.
What Changes When You Add Leadership
The COO hire at Hennessey Digital didn’t just add another pair of hands. It changed the operating model of the business.
With a COO managing operations, Jason could focus on the activities that only he could do: business development, strategic partnerships, and vision-setting. The CFO brought financial discipline and forecasting capability that a bootstrapped agency rarely develops. The CTO invested in the technology stack that would support the next phase of growth.
The doubling of revenue wasn’t about working harder. It was about removing the structural constraint that prevented the existing team from performing at its potential.
Why This Is Hard to Do Alone
Here’s the challenge for standalone agencies: the leadership talent that can drive this kind of transformation is expensive and hard to find. A qualified COO or CFO commands a salary that’s difficult to justify when you’re running a $4M agency with thin margins. The hire feels risky because the payoff isn’t immediate and the cost is certain.
Inside a portfolio, this calculus changes. The platform can support recruiting. The financial structure can absorb the investment period. And the track record of similar hires across other portfolio companies provides confidence that the strategy works.
Multiple agencies in the Herringbone portfolio have gone through this same transition. The specifics vary, but the pattern is consistent: adding the right leadership talent unlocks a growth curve that the founder couldn’t achieve alone.
The Lesson for Every Agency Founder
Jason’s story isn’t unique to his circumstances. Every founder will eventually face the same choice: continue doing everything themselves and accept the growth ceiling that creates, or invest in the leadership team that can scale the business beyond their personal capacity.
The timing of that investment matters. Make it too early, and the agency can’t support the cost. Make it too late, and the founder burns out, key employees leave, or the market window closes.
The portfolio model exists in part to help founders make this transition at the right time, with the right support, and with the confidence that comes from seeing it work for peers in similar situations.
If you’re the founder who does everything and you’re wondering whether you’re the engine or the brake, that question is worth exploring.