After years building something from scratch — the clients, the team, the reputation — the idea of selling raises three fears that keep founders up at night. 1. “I’m going to leave money on the table.” This one’s about preparation, not luck. Buyers pay premiums for clean, predictable businesses. If your financials are a mess, […]
Herringbone Digital Blog
Why the Best Agency Deals Happen Before the Founder Is Ready to Sell
The instinct is always to wait. Revenue is growing. The team is strong. The pipeline is full. Why would you have a conversation about partnership when everything is working? Because that’s exactly when you have the most leverage, the most options, and the clearest thinking. The founders who end up in the worst deals are […]
The CFO Hire That Changed Everything: A Case Study in Agency Growth
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: […]
From Bootstrapped to Backed: Three Agency Growth Stories
June 5, 2026
Every agency has a founding story. A moment when someone decided to bet on themselves. What happens next is rarely a straight line. Hennessey Digital started in a coffee shop in Burbank. Jason Hennessey was building websites and learning SEO before most agencies knew what the acronym stood for. He bootstrapped the business through its […]
The Legal Marketing Landscape: What 500+ Law Firm Relationships Teach You
June 1, 2026
Legal marketing isn’t a niche. It’s a category, and it’s one of the most demanding verticals in digital marketing. The stakes are high. A personal injury attorney’s marketing budget can run into seven figures annually. The cost per lead in competitive metros can exceed $500. And the difference between an agency that understands the legal […]
M&A activity in the digital marketing agency space is accelerating. Here’s why.
May 12, 2026
Here’s what agency owners are seeing. More buyers. More conversations. More transactions closing. I’m fortunate that the investment thesis of Herringbone is unique and so I get to have a lot of conversations with owners (DM if you’d like to learn more about our thesis). But on those conversations, they share with me what they […]
AI Is the Tailwind, Not the Threat: How Smart Agencies Are Adapting
May 9, 2026
The conversation around AI in the agency world has been dominated by fear. Will AI replace agencies? Will clients build in-house? Will the work that sustains a team of 50 be done by a team of 5? These are the wrong questions. The right question is whether your agency will be the one that harnesses […]
Post 24 of 24: A Recap Of The Entire Series
May 5, 2026
Over the past few months, I’ve shared what I’ve learned from helping digital marketing agency founders navigate the complex (and often misunderstood) world of M&A. We’ve covered everything from the fundamentals to the fine print — all with one goal: to help agency owners make smarter, more confident decisions when opportunity knocks. If you missed […]
Post #23 of 24 – Lessons Learned: What Makes the Best M&A Deals Work
April 28, 2026
Over the last few months, I’ve shared what I’ve learned helping agency founders navigate the world of M&A — from valuations and earnouts to culture and post-sale life. But if I had to sum it all up — the deals that work best all share one thing in common: alignment. Not just alignment on price.Alignment […]
Post #22 of 24 – How to Spot a Serious LOI (Letter of Intent)
April 21, 2026
If you’ve ever explored selling your agency, you know how exciting it is to receive that first Letter of Intent (LOI). It feels like validation — someone’s putting numbers on paper and saying,“We want to buy your business.” But here’s the reality: not every LOI is created equal. Some are genuine and actionable.Others are just […]