Post #14 of 24 – The Top 3 Seller Regrets (and How to Avoid Them)

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 good news? You can avoid most of those regrets — if you know what they are.

1️⃣ “I wish I had started preparing earlier.”
Most founders underestimate how long it takes to get truly “sale ready.”
They get that first call from a buyer, feel flattered, and think, “Sure, we can talk. ”Then they realize they don’t have clean financials, their contracts are outdated, or key metrics aren’t tracked.

The result? They either have to rush, or accept a lower price.

Preparation isn’t just about spreadsheets — it’s about telling a confident, data-backed story about your business.
Start 12–24 months before you think you need to. You’ll thank yourself later.

2️⃣ “I wish I had been clearer about my role post-sale.”
So many founders get to closing day without fully understanding what their life will look like after the deal.

Are you expected to stay for six months? A year? Indefinitely? Who makes decisions now?

Those details matter — a lot.

When expectations aren’t aligned, frustration builds fast.
– The buyer feels like the founder is disengaged.
– The founder feels like they’ve lost controly
– Clarity upfront prevents resentment later.

3️⃣ “I wish I had understood the deal terms better.”
This one is huge. Many sellers get fixated on the top-line number and overlook the fine print.

Things like working capital adjustments, earnout conditions, and non-compete clauses can dramatically affect what you actually walk away with.

If you don’t fully understand every term in your LOI or purchase agreement, ask questions. Bring in advisors who do this every day. A good lawyer or M&A advisor doesn’t just protect you legally — they protect your economics and your sanity.

Selling your agency can be one of the most rewarding moments of your
career.

But it’s also complex, emotional, and easy to underestimate. So be prepared and pay attention to the details

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