Post #12 of 24 – Why Cultural Fit Matters More Than You Think

December 9, 2025

Filed under: Uncategorized — herringbone @ 7:31 pm

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. You can model synergies.

But you can’t negotiate culture.

What “cultural fit” really means in M&A
Cultural fit is the alignment of values, decision-making styles, communication, and priorities between buyer and seller.

In practical terms, it shows up in questions like:

– How are employees treated and developed?

– Who makes the decisions and how fast are they made?

– What does leadership look like day to day?

If those things don’t align, friction shows up immediately — and it spreads fast.

What happens when it’s missing, I’ve seen great agencies lose their soul after being acquired by the wrong partner.

❌ Founders become frustrated because the new owners impose rigid systems.
❌ Employees feel lost as their culture of creativity turns into one of reporting and control.
❌ Clients sense the shift, and relationships start to erode.
Financially, those deals look fine on paper. Operationally, they struggle.

What happens when it’s right. When cultures align, it’s magic.

✔️ The buyer brings resources, process, and stability.
✔️ The seller brings energy, relationships, and deep client understanding.
✔️ Together, they scale faster than either side could alone.
✔️ The founder feels proud watching their team thrive with new opportunities.
✔️ The buyer gets what they paid for — and more.

How to test for cultural fit
– Spend real time with the buyer before signing the LOI.
– Ask about their post-acquisition track record — how do they integrate other teams?
-Talk to other founders who’ve sold to them.
-Observe how they treat people who aren’t in the negotiation room.

Trust your gut. Culture doesn’t show up in a spreadsheet, but you’ll feel it in every conversation.

When you sell your agency, you’re not just selling assets — you’re handing over your legacy, your team, and your reputation.

So don’t chase only the highest price.

Chase the right partner.

Because when the culture fits, everything else falls into place.

Contact us if you’re and agency owner and have considered selling or joining something bigger.

Post #11 of 24 – Common Negotiation Traps (and How to Avoid Them)

December 2, 2025

Filed under: Uncategorized — herringbone @ 4:05 pm

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 that price is paid, under what terms, and with what obligations — often matters far more.

Here are a few common traps I see sellers fall into again and again:

1️⃣ Focusing only on the headline number.

A $10M offer sounds better than $8M… until you realize $4M of it is an earnout tied to performance metrics you don’t control.
Always ask: What’s guaranteed vs. what’s contingent?
A lower price with cleaner terms often beats a higher price full of conditions.

2️⃣ Assuming the first LOI is final.

The LOI (Letter of Intent) feels like a finish line — but it’s actually the starting line.
Everything that follows — due diligence, final agreements, working capital adjustments — can change the economics of the deal.
Smart sellers keep some flexibility and don’t emotionally “bank” the LOI number too early.

3️⃣ Ignoring working capital.

This one surprises a lot of founders.
Buyers expect a certain amount of working capital (cash, AR, prepaid expenses) to remain in the business at closing. If you haven’t planned for that, it can reduce your actual cash proceeds by hundreds of thousands.
Don’t find that out the week before closing.

4️⃣ Negotiating emotionally.

Selling your agency is personal — you built it. But emotion clouds judgment.
I’ve seen founders walk away from great offers because they felt “disrespected,” and others accept poor deals because they just wanted it over with.
Take a breath, get advice, and remember: this is a business transaction.

5️⃣ Not understanding post-closing obligations.

Non-competes, transition periods, consulting agreements — these can all shape what your life looks like after closing.
Don’t just focus on the check. Think about what you’ll actually be doing 3, 6, 12 months later.

Here’s my advice: don’t negotiate to win — negotiate to align.
Because when alignment is strong, both sides walk away happy, and the business you built continues to thrive.

Contact us if you’re and agency owner and have considered selling or joining something bigger.