Herringbone Digital Blog

When most agency owners hear the words “due diligence,” their first thought is: “Oh no — this is where the fun ends.” And to be fair, diligence can be intense. It’s the part of the process where the buyer starts verifying everything you’ve told them — from your financials to your operations, contracts, people, and […]

If I could give agency owners just one metric to obsess over, it wouldn’t be revenue, it wouldn’t be headcount, and it wouldn’t even be profit. It would be client retention. Here’s why: I’ve seen it play out in real deals. Two agencies with the same $5M in revenue can command completely different valuations. One […]

Let’s be honest — most agency owners don’t start their business because they love bookkeeping. Numbers feel like a back-office chore, something you review once a year at tax time. But here’s the truth: to a buyer, your financials are the foundation of the business.  When a buyer looks at your numbers, they aren’t just […]

One of the first questions agency owners ask me is: “How do I know if I’m ready to sell?” It’s a fair question — but the answer isn’t always as simple as revenue or profit. Readiness is about much more than the numbers.Here are some of the key questions I encourage owners to ask themselves: […]

In the previous post, we talked about some of the items that can lead to higher (or lower) multiples. In this post, I wanted to dive a little deeper into 3 that really matter. . I call it the Triangle of Value. Why does this triangle matter? Because together, these three create predictable cashflow. And […]

Ever wonder why one agency sells for 2× EBITDA while another gets 8×? Here’s why: buyers don’t just look at your revenue. They look at the quality of that revenue. Factors that influence valuation include: I’ve seen two agencies, both doing $5M in revenue, sell for wildly different prices. One had sticky clients, strong margins, […]

Not all buyers are created equal — and knowing who’s across the table matters as much as the price they’re offering. Here are the big categories: Each has different goals: The same agency could get very different offers depending on the buyer type. Which means you need to think beyond “the multiple” and ask: What […]

Selling your agency isn’t one conversation — it’s a journey. A typical deal flows like this: #️⃣ Initial Outreach – a buyer expresses interest (or you decide to explore options). #️⃣ Intro Conversations – light discussions about fit, strategy, and goals. #️⃣ Letter of Intent (LOI) – a non-binding document that outlines headline terms. #️⃣ […]

Most agency owners hear “M&A” and think: 👉 Complicated Wall Street stuff 👉 Billion-dollar deals splashed in the headlines 👉 Not relevant to a 20-person shop in Austin or Denver Here’s the reality: M&A simply means a transfer of ownership. That could be one founder buying out another, a strategic buyer rolling you into their […]

How did private equity find me?” That’s one of the most common questions I get from agency owners. Here’s the process I use (and I suspect most other buyers aren’t too different): Step 1: Define the ideal candidate Here, we set the criteria for agencies that we want to acquire – industry focus, products offered, […]