The fear of leaving money on the table

I got an urgent message from a founder who was two days away from closing on the sale of her business – and she was getting cold feet.

She was desperate to talk through whether this was actually a good deal for her – or whether she should walk away.

When this founder got in touch, she said she’d spent the previous day reading all the resources on our website, and she wished she’d found it months earlier.

But here she was, nearing the finish line on her acquisition, and she wasn’t 100% sure she should go through with it.

What was holding her up? Whether she could get MORE for the business. 

She was questioning, was this actually a good deal, or could she do better?

I want to unpack a few things here, and share the advice I gave her, but first, here’s a brief look at this business.

This company was a marketing agency, with about $1 million in revenue, and $400,000 in EBITDA. It was on a growth trajectory, not crazy growth but solid growth, at about 10% year-over-year. 

The owner had two W-2 employees, plus a few contractors. And about 50% of their revenue came from a specific type of client. 

On the plus side, those client contracts were long-term; they went through 2028. But the founder felt that because of circumstances outside her control, it was likely many of those clients would not renew, which could mean a significant drop in revenue.

Her deal was a 2x EBITDA multiple. With her EBITDA at $400,000, the offer came in at $800,000.

That multiple was the sticking point for the seller. She’d realized the multiple was low, and now that she was nearing the finish line, she was wondering whether she should back out and try to sell the agency for more.

Here’s how I helped her think through it.

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First, I asked, what were the TERMS of the deal? How would that $800,000 be paid?

And she responded with something that’s pretty unusual for agency acquisitions, even at this relatively small size: That $800,000, would be paid, all up front, in cash.

Now, 2x EBITDA *is* low for an agency multiple. Our advisor partners tell us that this year, agencies of this size  typically sell for between two-and-a-half to 5x EBITDA. So 2x is definitely on the low end

But many agency sales include a heavy earn-out. It’s unusual to see all cash up front. 

This is where the *terms of the deal* really matter. 

When we hear about what a company sold for, we often hear the top-line number. But what’s left out of that conversation is the terms of the deal. 

Sometimes some of the money is held back and paid out over time through an earn-out, or a seller’s note, and sometimes it’s contingent upon hitting certain performance metrics.

Earn-outs – or really any payments that aren’t up front – are risky. Many founders never see all of that money. So having all the cash paid up front makes this deal significantly stronger.

Another quick note on deal terms…

This was a bootstrapped company, but for deals where the company raised venture capital, that top-line number is often even more complex. VC-backed founders only take home part of the payout, sometimes they walk away without much at all, because other parties owned equity in the business.

What’s relevant from a financial perspective for the owner is how much money you will actually take home. 

In this case, for a bootstrapped founder who owns 100% of the business and is selling for all cash up front, that’s $800,000 in her bank account, less any fees for a lawyer and taxes. In this case, she didn’t have an advisor or broker, which meant she didn’t have those fees – but this is also why she was calling me at the last second.

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Now, is it possible that this founder might have gotten better offers if she’d run a full process? 

Would she walk away with more if she had several buyers interested, rather than selling to the first buyer who knocked on her door?

Absolutely. Having more buyers in the pool is one of the best ways to drive up your sale price.

But was it likely that another buyer would beat $800,000 cash up front? Maybe not. Agency deals haven’t been particularly strong in 2025, and most founders aren’t seeing a lot of cash up front.

While I do usually think it’s smart to run a full process, so you have more interest and more leverage, backing out at this point could cost her this cash deal. And there’s no guarantee another buyer would come back with anything better.

This is where some founders fall into a trap.

It makes sense to do your best to sell for as much as possible, after all the effort you’ve put into building your business. 

But don’t make the mistake of always thinking there’s a better deal ahead – or you might miss the good or great deal right in front of you.

This reminds me of the work of Gretchen Rubin, an author who writes on happiness. She says most people fall into two buckets: they’re either a satisfier, or a maximizer.

Satisfiers do their research and then make a decision once their criteria are met. That doesn’t mean they settle, but they find what they need, and move on.

Maximizers are intent on making the absolute best decision. So even if they have a great option, they’ll keep looking at other possibilities. They’ll gather more and more information, until they finally know they’re making the optimal choice.

Now, it’s almost unfair to use this framework with selling your business, because it’s such a high stakes opportunity. 

But I do think it helps us understand that after a point, it can *hurt* you to overthink, especially if it leads you to pass on a life-changing deal, in pursuit of something better.

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The other big piece that comes into play is your personal circumstances: where you are in your career, what kind of financial impact this could have on you and your family, and what your goals are with the sale.

This founder told me she was 28, and she had dreams of starting other businesses. She and her partner were planning to have a family, and she envisioned herself running companies that were more lifestyle friendly, working fewer hours than she did with the agency. 

She already had some money in the bank, so this wouldn’t be her first financial win, but it would certainly be a meaningful addition to her nest egg. Her age is on her side here, too, because if she invests this money now, at 28, it could grow significantly over time.

So really, the only thing holding her back, was whether she was leaving money on the table.

What would you tell her?

My advice, was that she should take the deal. Though our conversation wasn’t quite that black and white. I prefer for founders I talk with to arrive at a conclusion on their own, armed with the insight we discuss, because there’s always nuance to these decisions.

But no deal is perfect. This one, is pretty darn good. The outcome is aligned with her goals, and going through with it puts the pieces in place for the seller to move on in the way she wants to.

Something better could *always* be out there. And of course I’d never want a founder to sell a business for less than it’s worth.

But always waiting for something greener to come along can blind us to opportunities that are right in front of us. 

Sometimes it makes sense to take a good deal, instead of waiting for the perfect one.

If you have feedback to share, or there’s another angle to this story I should have mentioned, I always love hearing from you. You can email me at alexis@TheyGotAcquired.com. Or leave us a review on Spotify or Apple.

Recording this podcast is a weird exercise of talking to myself in my home office, so I always appreciate reminders that someone’s listening.

Thanks for being here, and I’ll see you next time.