Herringbone Digital Blog

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 […]

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 […]

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 […]

I’ve posted about this before. But it’s so important, it’s worth posting again.But after years of working on both sides of agency M&A, I’ve noticed one simple truth: Every valuable agency sits on three legs — retention, growth, and profitability. I call it the Triangle of Value. 1️⃣ Retention – The FoundationIf you only focus […]

One of the most common questions I get from agency founders is:“When’s the best time to sell?” They’re trying to time the market — like investors watching stock charts. And it’s an understandable instinct. You want to sell when valuations are high, demand is strong, and buyers are eager. But here’s the reality: timing the […]

This is my favorite topic and one that I have been speaking about. If you’re an agency owner, chances are the phrase “private equity” triggers one of two reactions: 💭 “They’re ruthless — they’ll gut my company for profits.”💭 “They only care about spreadsheets, not people.” It’s one of the most persistent misconceptions I hear […]

When a buyer offers you a big number for your agency, it’s tempting to think: “That’s it — I’ve won.” But in M&A, the highest price doesn’t always mean the best deal. In fact, I’ve seen plenty of founders who took the “biggest offer” and later regretted it — while others who accepted slightly lower […]

Let’s bust one of the biggest myths in the agency world: “M&A is for billion-dollar companies — not for small to mid-sized agencies like mine.” I hear this all the time. Founders assume M&A means Wall Street suits, billion dollar valuations, 1000-page contracts, and corporate jargon. But here’s the truth: most M&A activity actually happens […]

When most agency owners start talking to buyers, they treat it like an interview — with them in the hot seat. But as a buyer, I enjoy it when sellers grill me. It shows (a) they are a serious seller and (b) they are an educated seller. Because selling your agency isn’t just a financial […]

A successful acquisition doesn’t end on closing day.In fact — that’s when the real work begins. The way you manage the transition period after a sale can determine whether the deal is remembered as a success or a slow-motion train wreck. Because here’s the truth: the ink may be dry, but your people, your clients, […]