Most people who want to buy a business never succeed. And not for the reasons you might think.

It’s not money. It’s not a shortage of good businesses. For some, it might be not putting in the required effort. But even those who are qualified and dedicated to the acquisition journey often fall short.

What stops them is the lack of confidence.

I look at confidence in acquisitions from two perspectives.

The first is deal confidence. Do I have the skills required to navigate the acquisition process and correctly determine if a deal is right for me?

The second is ownership confidence. Do I have the skills required to successfully run, grow, and lead the business I want to buy?

Deal confidence takes time and takes reps. Few people start the acquisition process feeling highly confident in their ability to make good decisions. On average, it takes looking at about a thousand deals to close your first. Part of that reason is there’s a huge learning curve that is built over time by putting in reps, and digging deep into deals. Each deal you look at, you learn from. Your confidence grows. It gets easier. But it’s uncomfortable in the beginning because it requires you to move forward with a high amount of uncertainty.

You’re more ready to own than you think

Ownership confidence is something most qualified buyers should have on day 1, but often don’t have because they aren’t looking at their future business in the right way.

I bought a laundromat without spending a day in the laundry business. My wife didn’t even like me doing laundry at home.

I didn’t really care that what I bought was a laundromat. I ran a marketing agency for over 10 years with the first few focused solely on marketing for local businesses. I wanted to buy a business in an industry where marketing was weak and that didn’t require my full-time effort.

I stumbled upon a laundromat that looked interesting. Solid profits. No advertising. No website. No Google listing.

And the more I explored laundromats, the more I saw that wasn’t an isolated case. It was systemic to the industry. That was the industry-wide signal I was looking for.

I wasn’t confident in my knowledge of laundromats. But I was confident that the marketing gap was real and that I knew how to fix it.

Most people look at a solid business in an unfamiliar industry and immediately dismiss it. That’s usually the wrong move.

Sure, there are some industries where having direct experience is critical. But in most, the experience required to manage the business day-to-day doesn’t have to come from you. It needs to be there, but it can come from others like existing employees or operators you trust.

Instead, I like to think about how a buyer can come into a successful business, fix whatever is broken (and even most successful businesses have something broken), and get an immediate bump in profit and cash flow.

Maybe you have marketing experience. Or maybe it’s sales, customer service, operations, process development, team building, strategy. Whatever superpower you bring into acquisitions, first and foremost find a business to buy where that will lift an already profitable company.

I worked with a buyer named David, thirteen years in corporate sales management. Despite having no manufacturing experience, he bought a manufacturing company. The production side of the business was managed by a long-time employee who wasn’t going anywhere. What the company lacked was a well-run sales team.

The outgoing owner was a good salesperson, but not a great sales leader. He was driving sales because “nobody else could do it.” Fortunately, he had others on the team to handle the ongoing customer relationships. Without that, the owner dependence might have been high enough to make the business unsustainable after he left.

David came in, relied on the key employee to keep production going, and spent the first six months focused on building out a world-class sales team. Profit grew by 18%, well above the 6% average growth over the prior three years.

I see this time and time again. The buyers most ready to be owners are the ones most convinced they aren’t. They convince themselves they can’t take over a specific business because of what they lack, versus tapping into the strengths that made them the successful person they are in the first place.

Where ready buyers freeze

I worked with an engineer a while back. Jennifer. Brilliant, deeply experienced, great with people. She also had a habit of overthinking, and that’s what got her.

She found a deal that fit her buy box perfectly. Around $3 million. Right industry, right size, right location, right financials. She knew it was a good fit, and so did I.

She did everything correctly at the start. Found the listing, called the broker, signed the NDA, got the CIM. We went through it together and it looked good.

Then she slowed way down.

She wanted to know more before she’d submit the LOI. How involved was the owner? Were the key employees going to stay on? A few line items in the financials nagged at her. All fair questions. But every one of them gets answered in due diligence, which happens after the offer, not before it. I told her to put in the LOI based on what she knew. It’s non-binding. It’s how you earn the right to ask those exact questions.

But she wanted answers first.

She was ready to own. That part was never in question. What she didn’t have was confidence in the deal itself, and she was trying to build it from the wrong side of the offer.

You never get all the answers up front

Here’s what Jennifer misunderstood, just like most buyers. The information you need to feel fully confident in a deal isn’t available to you when you’re writing an offer. It comes in later after you’ve earned the right to see it.

Let’s walk through a typical Main Street deal process.

It starts with the listing. Public, anonymous, a few lines of description and a rough financial picture. Enough to decide whether it’s worth a closer look. That’s it.

You sign an NDA and get the CIM. Now you see more. A basic one gives you the business name, the location, real financials with the add-backs laid out. A good one goes further: company history, an org chart, a customer breakdown with any concentration risk, monthly financials going back a few years. But that’s usually all you get before you have to make an offer. Maybe a short call with the owner or broker on top of it. That’s what everyone is working with.

It’s like buying a house. You make an offer, it gets accepted, and you still don’t know everything about the place. That’s what the inspection contingency is for. You assume what you’ve been told is true, you make your offer contingent on verifying it, and if the inspection turns up something, you renegotiate or walk. A business deal works the same way. The LOI is non-binding. It gives you the right to dig in.

Once your offer is accepted, everything is fair game. Bank statements, tax returns, payroll, invoices, sales data, the lease. You might be able to sit down with key employees. You can ask for just about anything the business has. That doesn’t mean you’ll get all of it, and that’s useful too. If a seller won’t hand something over, that tells you something. A delay in diligence is its own kind of answer.

So all those questions Jennifer wanted answered before she’d make an offer, how involved the owner was, whether the employees would stay, the line items that nagged at her, those were diligence questions. The offer is what unlocks the answers. The confidence she was waiting for was sitting on the other side of the move she wouldn’t make - the LOI.

Why qualified buyers don’t close

Jennifer held her ground and asked for a call with the owner before she’d submit. The broker was happy to set it up. But while they worked out the timing, another buyer put in an offer. It got accepted. The deal closed a few months later, with someone else’s name on it.

She was ready to own. She lost the deal anyway. She went looking for certainty too early, and the answers she wanted were sitting in diligence. All she had to do was sign a non-binding LOI.

This is pretty common. Qualified buyers often move too slowly and don’t make enough offers. If you’re slow and you’re not putting in offers, you’re not going to close. Obviously.

I get this can be challenging. Buyers believe they need to feel certain before making an offer. But the acquisition process isn’t designed to do that. Certainty gets built over time during a deal, not all at once up front.

If you’re qualified, get going

For me, a qualified buyer is someone who has the financial capacity to close a deal, a reasonable timeline, and the right experience.

If that’s the case, the next steps are simple. Get into a deal.

Be confident that the experience you bring - your superpower, what made you the success you are - will allow you to achieve that same level of success as an owner.

Don’t be held back by not being confident in a deal up front. If you even remotely think a deal could be a good fit, move forward. Each step allows you to be more confident it’s the right deal, or the wrong deal.

Best case scenario, you find the perfect business. Worst case, you gain valuable lessons that will help you going forward and spend a little time doing so.

Don’t remain on the sidelines waiting for a high degree of confidence that will never come without taking action.

Review deals. Make offers. Get under contract. Believe in yourself and you’ll get across the finish line.

If this was helpful, pass it along to someone looking to buy a business.

I write On Owning for people buying, selling, and growing businesses. Subscribe if that’s you.

And if you’d rather not go it alone, that’s what I do. I work with a small number of buyers through their deals, helping them figure out what’s worth pursuing and what isn’t, while they stay in control. Working on a deal now? Reply and tell me about it.

Six reasons qualified buyers haven’t closed a deal. None of them are deal quality.

If you’ve spent at least a few months searching for an acquisition, you’ve probably told yourself the right deal hasn’t surfaced. You’re learning. You’re running the numbers. You review listings, sign NDAs, talk to brokers. You tell yourself you’ll know the right one when you see it, but so far every deal has had an issue.

That self-description is hard to argue with from the inside. It defends the months you’ve spent searching and lets you keep the dream alive. The work feels real because it is real. Listings get read. Spreadsheets get built. Questions get asked.

But the buyers I’ve watched close deals realized they needed to do a lot more.

They protected hours just like they were training for a marathon. They submitted offers even if they didn’t feel ready. They broke down the acquisition process into stages instead of trying to swallow it whole.

They engaged seriously with listed deals so brokers took them seriously and brought them deals later. They hired pros rather than trying to become every expert themselves. They negotiated terms when price felt stuck instead of walking.

I’ve worked on over 200 transactions on both sides of the table, and I’ve watched qualified buyers stall in the same six places.

The work you really need to do is figuring out your stall and breaking it.

Why hobby hours don’t close deals

It takes 600 to 1,000 hours of focused work to close one deal. Some people are faster, some are slower, but the range is real.

Run the math. If you want to close in twelve months, that’s 11 to 19 hours a week, every week. Below that floor, the math doesn’t work.

Buyers who treat acquisition like a hobby, fitting it around their job and life when there’s time, never get the reps in. They look at a listing here and there. They sign an NDA every now and then. They run a quick screen on a deal and move on. The hours never compound. Neither does the pattern recognition that comes from doing the work in volume.

Buyers who close deals treat it as a part-time job. For some, full-time. They build routines around it, schedule the time, and follow the schedule. Not hobby hours. Marathon training.

If acquisition is bumping up against everything else in your calendar and losing, you have a calendar problem. Block the hours. Defend them.

Confidence is built inside deals

One buyer had everything lined up. Corporate finance background, $300K saved, 8 months of active research. She could walk you through EBITDA math without pausing. She found 3 businesses that looked perfect.

The first had an owner who wanted to stay on for 18 months post-close. The second had a lease renewal coming up in 8 months. The third had a key employee she wasn’t sure about.

Each time, she stepped back. Kept searching.

Six months later, she was still searching.

None of those issues were fatal. All three were manageable, the kind of thing you negotiate through in due diligence or structure around in the LOI. But she didn’t know that yet, because she’d never been inside a deal. The confidence you need to evaluate those issues clearly only comes from real deal experience.

Another buyer submitted an LOI 5 months into his search. He told me he was maybe 60% sure. We talked through what he didn’t know and which stages of due diligence would answer those questions. He submitted anyway.

He didn’t close that one. Due diligence surfaced customer concentration he couldn’t get comfortable with. But three months later he was in a second deal, asking sharper questions, moving faster, knowing what he needed to see. He closed 4 months after that.

Confidence is built inside deals, not before them.

Overwhelm is a feeling, not a fact

The pattern is easy to recognize.

“I don’t know where to start.”

“There’s so much to learn.”

“I can’t tell a good deal from a bad one.”

“I don’t want to overpay.”

When you’re screening listings, you don’t need to get hung up on how to structure the deal or line up financing. You’re answering one question. Does this business pass your buy-box?

When you’re structuring the deal, you don’t need to obsess over every detail of due diligence. You’re working out terms that make sense for both sides.

Buyers who get paralyzed about every step of the acquisition process never get a deal done. Every question surfaces another question. Good deals pass by while they’re still deciding if they’re ready to engage with one.

Buyers who close solve the problem in front of them. They are confident in their ability to solve future problems once they get there.

Overwhelm is a feeling. The work is simpler than it looks. One problem at a time, in order.

The deals are there

Most acquisitions close through brokers. Axial’s 2025 survey of independent sponsor buyers found 93.8% sourced their deals through sell-side intermediaries. BizBuySell tracked 9,586 small businesses closed on its platform alone in 2025. There’s no shortage of listed deals.

But pocket deals, those represented by a broker but not listed publicly, are real at the higher end of the lower middle market. Above roughly $5 million in enterprise value, a meaningful share of transactions never hit a listing platform. A broker quietly shows a deal to two or three buyers they already know and trust.

Two things put a buyer on that short list. The first is financial qualification. Can you actually close at the price the broker is going to ask? The second is whether you can close on a timely basis. Brokers gauge that by watching how you work. They notice when you return calls within hours, sign NDAs and actually review the CIM, ask sharp questions, submit offers that aren’t shots in the dark, and walk through diligence cleanly even when the deal doesn’t close.

That short-list position is built on the listed deals you engage with, long before you close one. The work you do on listings is what makes you the buyer a broker thinks of when a pocket deal needs a quick, qualified take.

The deals are there. They come through brokers, and they reach buyers brokers trust to close.

The problem was never deal availability.

Who, not how

One buyer I worked with was a corporate finance VP in his mid-40s, highly qualified. He spent eight months learning everything he could about acquisitions and took some action as well. Reviewed a handful of listings, signed a few NDAs. He could discuss deal points with surprising fluency for someone who’d never done a deal.

He still hadn’t submitted an offer. Every time he got close to a listing he liked, a new question he just “had to answer” would stop him.

“I need to better understand reps and warranties before I make an offer.”

“I need to dig into tax structuring.”

The learning felt like doing work. From the outside, it really wasn’t.

Another buyer with a similar background spent their first eight months not only learning about M&A but taking REAL action. As soon as he found a deal he really liked, he brought in the people he needed to get an offer on the table. He hired a CPA experienced with acquisitions and a seasoned M&A attorney. And I introduced him to an SBA banker who I worked with previously on a similar deal.

He closed in nine months. His CPA caught two add-back issues during due diligence that would have cost him $80,000. His attorney negotiated indemnification caps the seller’s counsel was going to push past. His banker structured the SBA loan to leave working capital for the first 90 days.

You will never analyze financials like a CFO who’s done it for twenty years. You will never structure a deal like an M&A advisor who’s done hundreds. You will never draft a purchase agreement like an attorney who’s drafted a thousand. You don’t have to.

Your job is to run and close the deal. Find the pros who can take care of the things you’re not an expert in.

Who, not how.

Walking over price kills good deals

A buyer I worked with was looking at a business doing $800,000 in EBITDA. The seller wanted 5.2x. The buyer thought it should be 4.5x. He’d run the math against industry averages and decided the asking price was too rich.

The business had what every buyer claims they want. Recurring revenue. Loyal, long-tenured employees. A management layer below the owner. Good customer concentration. EBITDA up every year for the last six. The owner was retiring on a clear timeline and willing to stay 6 to 12 months for handoff.

He almost walked at 5.2x. We negotiated terms. He came up to 4.9x. In exchange, he got a meaningful seller note at favorable rates and a working-capital target that protected him through the transition. The seller felt respected and accepted. The buyer paid a higher multiple than he’d originally targeted, but his cash-at-close didn’t change much.

That was three years ago. EBITDA is up 35%. He’s paid down most of the seller note. He has the freedom he bought the business to get.

He almost walked over a $560,000 difference on purchase price. Three years later, the equity he’s built dwarfs that number.

Better businesses deserve higher multiples. The multiple is a proxy for risk. A lower-risk business earns a higher number. When price feels stuck, negotiate the structure. Walking over price kills more good deals than it saves you from bad ones.

The work you’ve been missing

The work you’ve been doing is real. The hours of learning. The listings reviewed. The questions you’ve taken to your CPA. The conversations with friends who’ve bought. None of that was wasted.

It was just incomplete.

Closed deals come from different work. The offers you didn’t submit. The brokers who didn’t yet think of you for a pocket deal. The terms you didn’t negotiate when price felt stuck. That’s the work.

Six patterns. One of them is yours. Maybe two.

Read back through. Mark the one that hit. Then break it.

That’s the work you’ve been missing.

If you’ve been searching for months without closing, reply and tell me which pattern you recognized. I read every reply.

If a friend is searching, share this with them. It’s the playbook I wish every buyer had in their first month.

Subscribe for next week’s piece on the seventh problem this one doesn’t address. What happens to your confidence the week after you close.