Why Business Owners Sell (Hint: It's Not Always About the Money)

You've probably heard the advice: lead with your best offer, show them the money, make it irresistible.

That advice assumes business owners are selling because they want to maximize dollars. And sometimes that's true. But most of the time, it's not even close. 

We've talked to hundreds of business owners, and we can tell you this with certainty: the reason many people sell their business usually has nothing to do with getting the highest price.

The Baby Boomer Math Everyone Gets Wrong

You've heard about the Silver Tsunami. 

Ten thousand baby boomers turn 65 every day. Baby boomers own approximately 40% of all small businesses in the U.S., and more than 70% of these companies will need to transition ownership in the coming years.

Everyone talks about this like it's a massive buying opportunity. And it is, but not for the reason you think.

The opportunity isn't that these owners want to sell. Most of them don't. The opportunity lies in the fact that they have to figure out what happens next, and most of them haven't thought it through.

According to research from the Exit Planning Institute, only about 30% of business owners have any kind of succession plan. That means 70% are running successful businesses with absolutely no idea what happens when they can't or don't want to run them anymore.

They're not actively looking to sell. They're actively avoiding thinking about it, and that creates an opening for buyers who can help them solve the problem they're pretending doesn't exist.

Why Leading With Money Backfires

So if money isn't the main driver, why do so many searchers lead with financial terms?

Because it feels safer. You can model a financial offer. You can compare multiples. You can build a spreadsheet that proves your offer is fair.

But when you lead with money, you're forcing the owner to think about the transaction as purely financial, and that makes them defensive.

If this is just about money, then they should get the highest possible price, right? So now they're thinking about whether your offer is high enough, whether they should shop it around. and whether someone else might pay more.

You've turned it into a negotiation before you've built any trust.

The better approach is to start with their story - what they built, why it matters, and what they want to see happen next. Once you understand what they actually care about, you can structure an offer that addresses those concerns. The financial terms matter, but they matter in the context of everything else.

The Questions That Open Doors

These are the questions that have led to real conversations, not polite brush-offs:

• "What are you most proud of building here?" This gets them talking about their journey, not defending their asking price. You learn what matters to them emotionally.

• "What would make you feel good about the next chapter for this business?" This frames the conversation around their vision, not your acquisition model. They start thinking about you as someone who might carry on what they built.

• "What concerns you most about eventually transitioning out?" This gives them permission to voice their fears. And once you know what they're worried about, you can address it directly.

• "How do you see your role changing over the next few years?" This one's subtle. It assumes change is coming and asks them to articulate what it might look like. Much less threatening than "Are you thinking about selling?"
  

Notice what these questions have in common. They're about the owner's experience, not your agenda. They invite storytelling, not negotiation.

What This Means For Your Approach

If you're reaching out to business owners hoping to find off-market deals, your entire strategy needs to shift.

Stop treating outreach like you're pitching an investment opportunity. You're starting a conversation about one of the biggest decisions this person will ever make.

That means your first email shouldn't mention valuation or talk about your financial backing. It definitely shouldn't include the phrase "strategic acquisition." Instead, acknowledge what they've built. Show that you've done your homework, and ask a genuine question about their vision for the future.

Here's what that looks like in practice:

• Bad first email: "I'm a well-capitalized searcher looking to acquire businesses in the manufacturing sector with strong EBITDA margins. Would you be open to a conversation about a potential transaction?"

• Good first email: "I came across [Company Name] and was impressed by [specific detail that shows you actually looked at their business]. Building that over [X years] is no small feat. I'm curious, have you thought about what the next chapter looks like for you and the business?"
  

The first email sounds like every other buyer. The second email sounds like a human being who might actually care.

The Action Steps You Can Take Today

Enough theory. Here's what you should actually do:

• Rewrite your outreach. Take whatever email template you're using and remove every piece of financial jargon. Then rewrite it to focus on one primary thing: showing you understand what they've built and asking about their vision for its future. In addition, make it clear why you are a good fit for that business, ideally tying it to your background.

• Research before you reach out. Look at their reviews. Check their about page. See if they're involved in local community stuff. Find one specific thing you can mention that shows you actually looked.

• Ask better questions. Next time you're on a call with an owner, try this: "Before we talk about any of the business details, I'd love to hear your story. How did you end up in this business?" Then shut up and listen. You'll learn more in ten minutes than you would in three due diligence calls.

• Stop competing on price. If you're in a situation where you're bidding against other buyers, you've already lost. The winner in those scenarios is whoever pays the most or whoever the owner already trusts. You can't win on price (someone can always pay more), so don't play that game. Find owners before they're shopping around.

• Build a pipeline of conversations, not a pipeline of targets. Your goal isn't to contact 500 owners this quarter. Your goal is to have 20 real conversations with owners who are in the "considering selling" phase. That's where deals come from.

The Bottom Line

Business owners don't sell because they ran a DCF model and determined it's optimal timing. They sell because they're solving a personal problem. They're figuring out what happens next,  and they're looking for someone who will take care of what they built.

If you can help them solve that problem and are in the market with your offer, the financial terms work themselves out. If you can't, it doesn't matter what you offer. 

And if you're thinking, "This all makes sense, but I'm reaching out to 50 owners a week and I can't do deep research on all of them," you're right. That's where having a system comes in. But that's a topic for another post.

For now, just try this: before you send your next batch of outreach emails, ask yourself one question. "If I received this email about my life's work, would I respond?" If the answer is no, try again.

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