Herringbone Digital Blog

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, […]

I’ve been part of dozens of agency M&A deals — on both sides of the table. And if there’s one thing I’ve learned, it’s that seller’s remorse is real. Even when the money clears, even when the deal goes smoothly, many founders look back and say: “I wish I’d done a few things differently.” The […]

If you’ve never sold a business before, it’s easy to picture the finish line like this: you sign the papers, money hits your account, and you ride off into the sunset. Sometimes that’s true. But in most cases — especially in agency M&A — life after the sale is a transition, not a vacation. And […]

When people talk about selling their agency, the conversation almost always starts with numbers — valuation, multiples, EBITDA, earnouts. But here’s something I’ve learned after years of M&A work: the success or failure of most acquisitions isn’t determined by the financials. It’s determined by cultural fit. You can negotiate deal terms. You can structure earnouts. […]

Let’s talk about one of the most misunderstood (and emotionally charged) parts of any deal: negotiation. Most agency owners approach a negotiation thinking it’s all about one number — the price. But that’s exactly where most sellers go wrong. In reality, the purchase price is just one part of the deal. The structure — how […]

Few words in M&A trigger as much emotion as “earnout.” If you’ve ever talked to someone who sold their agency, chances are you’ve heard horror stories: “We never got our earnout.”“They changed the rules after closing.”“It was just a way to shortchange us.” And I get it. I’ve been on both sides of earnouts — […]