What Nobody Tells You About Exits (I Learned It the Hard Way)

I have sold over 75 businesses and closed more than nine figures in transactions. But that is not how this story starts.

It starts with me selling my first company and realizing, much later, that I had no idea what I was doing.

A buyer reached out. Asked how much I wanted. I named a number out of thin air.

No valuation. No competitive process. No leverage. No real understanding of how exits work.

I thought I had won. I got every dollar promised to me. But it took years to understand what that exit cost.

The Business That Built a Tool to Survive Itself

Before I ever sold a company for someone else, I was trying to build one of my own.

An ecommerce supplement business. Growing fast. Over nine figures in revenue in our best year. Twenty-six employees. A warehouse with thousands of shipments going out the door.

But supplements are a brutal business. Inventory has to be bought months in advance. Ad costs can change overnight. Cash is always tied up in spend or in stock. We always seemed to be cash poor.

So I built a tool to fix it. A SaaS reporting platform called OfferProphet. It sat behind the customer-facing front end of my ecommerce business and showed me the truth about profitability. Not the revenue number. The real number.

OfferProphet helped me understand the business. But it did not give me my life back.

I was working longer hours than ever. Chasing stability that never quite arrived. Telling myself that once things smoothed out, I would finally slow down. Instead, I was disappearing at home.

One Saturday, hiking in northern New Mexico with my boys, my youngest son Aiden looked up at me and asked: "Dad, why can't we do more hiking?"

I said: "Son, Daddy has to work to pay for everything."

I knew exactly what I was becoming. My father was a Colonel in the Army. He provided for us. I barely saw him growing up. And there I was, repeating the same pattern.

That is when selling OfferProphet stopped being a business idea. It became personal.

My First Exit

The buyer who reached out was not random. They were a strategic company already operating in the same performance marketing space. A company that today goes by Sticky.io.

Brian, the CEO, sent a simple message: "How much do you want for it?"

I had never been approached by a buyer before. I did not ask for time. I did not get a valuation. I did not contact a broker for their opinion.

I thought about it for a moment and named a number. A number I had pulled from instinct.

At the time it felt audaciously high. What I did not understand was that I had just made the most costly mistake in the entire process. I had given away my price without any market research. I was talking to exactly one buyer. I had no leverage, no competition, and no context for what the market would pay.

I was negotiating blind. The buyer across the table was not. Acquisitions were their job. They had done this dozens of times.

We went back and forth on price. Then we negotiated on terms. And the terms are where my real risk showed up. The deal was not all cash at closing. Payments were spread over time. All seller financing. I was exhausted by then. I just wanted it done.

I told myself what a lot of founders tell themselves in that moment: I just want this over.

And that feeling of relief replaced leverage without me even realizing it.

What the Win Really Cost

Here is something I have never shared publicly before.

I sold a negative cashflow SaaS startup, barely 16 months old, with five or six customers. I got mid-six figures for it. It had cost me about forty thousand dollars to build.

By most measures, that was a remarkable outcome.

But the deal was all seller financed. For two years, I checked my bank account every month wondering whether the wire was coming. The anxiety of "what if they stop paying" did not go away until the final payment cleared.

What I did not understand then was what I lost by not understanding the market. I had built something a strategic buyer wanted badly enough to call me directly. That is a rare position of leverage. I had no idea how to use it.

I could have gotten a better deal. Without question. But the exit gave me something more valuable than a higher multiple. It gave me my life back. I changed everything. Brought my boys home and started homeschooling them. Got more time with my sons than I had had in years.

That experience taught me something I did not have words for at the time: it is much harder to build a truly passive business than it is to sell a business and invest the proceeds in passive cash-flow-producing assets. And once you understand that, exits start to look completely different.

What I Discovered on the Other Side of the Table

After selling OfferProphet, I started asking the questions I should have asked before.

Why did the buyer negotiate price before terms? How did they know exactly how to structure the deal while I had no idea? Why did they seem calm while I was anxious and just relieved it was over?

I started talking to experienced brokers. Not casually. Deeply. About how M&A in the internet and technology space worked.

Those conversations changed everything.

These brokers told me there were thousands of buyers actively looking for businesses like the ones I had built. Private equity firms. Strategic acquirers. Search fund operators. Family offices. Not hypothetically. Actively.

I remember thinking: where was this market? How did I not know it existed?

And that is when I understood something fundamental about exits. Exits are not about finding a buyer. They are about accessing a market. And once you understand the market, leverage, structure, and outcomes start to make sense.

I had stumbled into my exit. I had not engineered it.

Where Deals Break

Most founders think deals fall apart because a buyer got cold feet.

After watching hundreds of transactions and managing more than 75 deals with my hands directly on them, I can tell you that is almost never what kills an exit.

Deals break after the LOI. During diligence. When the business has not changed, but risk becomes visible.

I had a client selling an ecommerce business. Strong brand. Clean financials. Healthy EBITDA. Signed LOI. Months of diligence. Financing approved. Lawyers aligned. Closing scheduled for a Friday.

At the last minute, the sellers pushed for more money. Not unreasonable. Just one extra earn-out adjustment.

That single decision moved the closing from Friday to Monday.

Monday morning, new tariffs on China were announced. The lender got nervous about inventory exposure. They pulled financing. A deal that was scheduled to close that Friday collapsed over a weekend. Nothing about the business had changed. The only thing that changed was timing.

Momentum protects deals. For internet-focused businesses, time is risk. The longer a deal stays open, the more external risk it absorbs.

I had another deal, an eleven-and-a-half-million-dollar ecommerce transaction. Profits had dipped in the final months before closing. Normal seasonal advertising fluctuations. Nothing structural. But the buyer came back demanding a retrade. The sellers were ready to give up millions just to save the deal.

But we had multiple offers. We had real buyer demand. I told the buyer my clients were prepared to walk and move forward with the next offer. I meant it. The buyer backed down. We conceded some value but protected the majority of the deal. It closed.

Whoever understands the deal structure best, and is willing to walk, controls the outcome.

The Decisions That Kill Deals Quietly

Deals do not die because of buyers or lenders. They die because of sellers.

I have walked away from clients who hid cash sales off the books. Who manipulated inventory purchases to reduce their tax burden. Who ran excessive personal expenses through the business in ways that look intentional to a buyer even when they were done out of ignorance.

Buyers see this immediately. Lenders sniff it out. No amount of storytelling repairs broken financial trust.

Fewer than one in twelve businesses that go to market ever sell. In internet and technology specifically, the odds are often worse.

The deals that close are not always the biggest. They are the ones where risk is understood, expectations are aligned, and momentum is protected all the way to the wire.

What the 27 Factors Mean

When that first buyer asked me how much I wanted for OfferProphet, I thought selling a business came down to one thing: price.

It was not until much later that I learned there are 27 different factors that go into valuing and selling a business properly.

Things like market demand. Buyer psychology. Risk concentration. Growth trajectory. Transferability. Financing availability. Customer retention. Owner dependency. Recurring revenue quality.

Twenty-seven factors. I knew none of them on my first exit.

Every experienced acquirer knows all of them. When a founder sells without understanding what a buyer is evaluating, they are walking into a room where the other person has read the manual and they have not.

How I Engineered a Different Approach

Most exits leave too much to chance. Buyer financing. Lender confidence. Seller expectations. Momentum.

The traditional process puts a business on the market, hopes buyers appear, waits for an LOI, and then hopes nothing spooks the deal in the diligence window.

In that model, nobody owns certainty.

I stopped asking who the buyer would be. I started asking what would have to be true for this business to close.

That question changes everything about how you approach an exit.

Before I take a business to market, I want to understand buyer financing first. Not hypothetically. Specifically. Can this business support acquisition debt? How much leverage will a lender allow? What risks will kill the deal at the lender level before the buyer even gets nervous?

When sellers understand early what cash at closing realistically looks like, what portion might be seller financing, whether rolled equity is part of the structure, their decisions become calmer. Panic goes down. The probability of a retrade disappears.

My average listing attracts around 97 buyers per deal. More than half of my closed deals have had multiple competing offers. That competition does not come from hype. It comes from preparation.

What Exits Change

After enough exits, you notice something most people do not talk about.

Yes, the money matters. Of course it does.

But it is rarely what founders focus on most after the wire hits.

I have watched founders close deals and do things they had not done in years. One retired to France after decades in the same business. Another stepped away from daily operations entirely and started mentoring younger founders. Others did not retire at all. They reinvested, built again, moved into roles with less pressure.

Different outcomes. Same experience.

The documents are signed. The wire hits. Everyone congratulates each other. And then the founder goes quiet.

Not because they are unhappy. Because for the first time in years, the noise stops.

The Delay That Costs the Most

Most founders do not plan an exit. They delay it.

They tell themselves: I will think about it next year. Once revenue is a little higher. After this next growth phase.

And then years go by. And the business becomes their identity. What I have learned, both personally and professionally, is that exits get harder the longer you delay them. Not financially. Emotionally. The longer a business defines your daily life, the harder it is to imagine what comes after.

Exits do not reward urgency. They reward preparation. That is the part nobody tells you until it is too late to act on it.

Where to Start

If you are a founder who is thinking about an exit, next month or several years from now, the best time to start understanding what your business is worth is right now.

Not because you are ready to sell. Because the 27 factors buyers evaluate are things you can improve. Owner dependency. Financial documentation. Recurring revenue structure. Customer concentration. All of these can be addressed with time and intention.

Exits that happen by design outperform exits that happen by accident. Every time.

I do free valuations at natelind.com. The intake form takes less than two minutes. What you get back is a real picture of where your business stands and what would move the number before you go to market.

Frequently Asked Questions

What is the biggest mistake founders make when selling a business?

The biggest mistake is entering a sale without a competitive process. Most founders sell to the first buyer who expresses serious interest. When there is only one buyer, they set the terms. Price gets anchored without market validation. Structure gets worse because the seller has no alternative. The result is leaving significant value on the table without knowing it.

Why do deals fall apart after the LOI is signed?

Most deals break after the LOI because the business changes during the diligence window, undisclosed issues surface under scrutiny, or the seller panics and destroys momentum. For internet and technology businesses specifically, time is risk. The longer a deal stays open, the more surface area there is for external factors, lender sentiment, ad cost changes, or market events to derail the process.

What is the relief trap in a business sale?

The relief trap is the moment a founder decides they just want the deal done. Relief replaces negotiating position without the seller realizing it. The buyer senses the shift and uses it to renegotiate structure: lower cash at closing, longer seller note, earn-out contingencies. It is the most expensive emotion in an exit. Fear makes you cautious. Relief makes you careless.

How do exits change a founder's life beyond the financial outcome?

The financial outcome is rarely what founders focus on most after closing. The dominant experience is the noise stopping. For founders who have been running a business for a decade or longer, exits create space that did not exist before. Time with family. Ability to recalibrate. Freedom to choose what comes next. The money represents those options.

What does it mean to negotiate blind when selling a business?

Negotiating blind means entering a sale without knowing the market value of what you are selling, who else would want it, or what comparable businesses have sold for. Most first-time sellers negotiate blind. They have one buyer, a number pulled from intuition, and no competitive process to validate demand or pressure terms. The buyer, who has done this many times, has enormous structural advantage.

How long does it typically take to sell a business?

From engagement to close, most transactions take six to nine months. Getting to a signed LOI typically takes around five months. From LOI to wire is another three to four months. The tighter the process, the less surface area for something to go wrong in the diligence window.

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What Nobody Tells You About Exits (I Learned It the Hard Way)