For me, somewhere around kilometer twenty of an ultra trail race, something happens that almost nobody talks about at the start line. Your legs are still moving. Your heart rate is manageable. Nothing is acutely wrong. But a fog rolls in that is harder to describe than pain, a slow erosion of the parts of you that decide things. You stop talking to the people around you. You stop eating on schedule. You stop checking the clock. The race becomes smaller, then smaller, until the only thing in it is the next ten meters, then the next step. This is the moment when runners win or quit, and the difference between them is almost never fitness. It is whether they recognized what was happening early enough to do something about it.

I have come to learn that mid-market M&A deals are often won and lost in the same way. Not on valuation, not on terms, not on the brilliance of the structure. On whether the people in the deal recognize fatigue early enough to adjust. The parallel between ultra running and an M&A process is not a metaphor I am throwing out loosely as a means of having some “roll your eyes worthy” LinkedIn post. It is the most accurate frame I've found for what actually happens inside a six-to-nine month transaction, and it has changed how I run deals.

By our internal numbers, the average mid-market M&A transaction consumes between four hundred and eight hundred hours of human time from kickoff to close, depending on complexity. That is the equivalent of a project's worth of work running in parallel with everyone's actual job, on a compressed timeline, under emotional stakes that most participants have never experienced before. It is, quite literally, an endurance event. And like every endurance event, it is governed less by capacity than by pacing.

The three fatigues

Most people, when they hear the phrase deal fatigue, picture exhaustion. Long hours, late nights, too many calls, falling asleep on your desk like they show in many a Wall Street movie. That is one part of it, and it is the least dangerous part. What I have watched create insurmountable deal problems is generally not the physical tiredness. Rather, it is the slow degradation of two other systems that nobody pays attention to until they fail.

Physical.

This is the visible layer. Diligence requests that arrive faster than the founder's team can answer them. Weekend calls that erode the recovery time the body actually needs to function. The cumulative effect of running a company at the same time as running a process. Founders almost always underestimate this, because they have spent twenty years running their company at high intensity and assume a deal is just one more thing on top. It is not. It is a second full time job layered on the first, and the body keeps score. It gets exacerbated by family life, lifestyle, and all the demands a founder has on their time outside of work, none of which subside while the deal is in motion. By month four of most processes, I can see it in the founder's face on a Teams call. A flatness around the eyes that was not there at kickoff.

Emotional.

This is the layer that surprises people. A deal is an emotional event before it is a financial one. The buyer's questions feel like accusations. The lawyer's redline feels like distrust. The accountant's adjustment to working capital feels like theft. None of these things are personal, but all of them feel personal, because what the founder is being asked to do is hand over the thing they have built to people who have known it for six weeks. Emotional fatigue compounds quietly. The founder becomes less willing to give ground, more sensitive to perceived slights, more likely to read malice into mundane process. By the time it becomes visible, it has usually been building for months.

Psychological.

This is the most dangerous layer, and the one almost nobody names. Psychological fatigue is the slow erosion of the founder's ability to make good decisions. The signs are subtle. A founder who used to respond to LOI feedback in twenty-four hours now takes a week. A founder who used to read documents thoroughly now skims. A founder who used to push back on questionable provisions now signs them. This is not laziness. It is cognitive load failure. The founder has been making hundreds of small decisions a week for months, and the executive function is depleted. The deals that die at the eleventh hour for reasons that look irrational are almost always deals where psychological fatigue is very present.

Deal fatigue does not arrive. It accumulates. By the time anyone names it, it has usually been compounding for ninety to one hundred and twenty days.

Why mid-market is the breeding ground

Large cap deals have armies. A nine-figure transaction has dedicated diligence teams, in house M&A counsel, integration officers, and a CEO whose job description includes managing transactions. The work is enormous, but it is distributed. Micro cap deals, on the other end, are usually fast and clean. A couple of advisors, a small lawyer's bill, a transaction that closes in ninety days because the complexity does not justify more.

Mid-market is the worst of both worlds. The deals are complex enough to require the full apparatus of a real transaction, full diligence, structured purchase agreements, working capital mechanics, escrow, reps and warranties, the whole architecture, but the company does not have the bench to absorb it. The founder is the CEO and sometimes the CFO and the head of HR and the keeper of the customer relationships. There is no integration officer. There is no in house counsel. The deal team is the founder plus one or two leadership members plus the external advisors, and that team is also running the business. The gap between what the process demands and what the company can actually supply is widest in the mid-market, and that gap is where deal fatigue lives in earnest.

The buyer feels it too. Mid-market buyers are often running multiple processes in parallel, working with debt providers who require their own data rooms, and managing internal investment committees who want updates the buyer does not yet have answers for. The advisors in the middle, including us, are absorbing the friction between both sides while running their own portfolio of mandates. Everyone in a mid-market deal is being pressed. Everyone is operating on incomplete recovery. And almost nobody is talking about it.

The ultra runner's protocol, applied

Here is what ultra runners actually do, not metaphorically but operationally, and how each translates to running a deal.

Pacing.

Ultra runners do not run at one speed. They run a deliberate negative split, holding back early so they have something left for the back third. The deals I have seen close cleanly do the same thing. The first sixty days of a process should not be the most intense, with all nighters and weekends being worked. Those will come. They should be the most organized. Diligence schedules, data room population, response timelines, all of it sequenced so the team is not in a sprint when the deal is in a marathon. The deals that die because of deal fatigue in months five and six almost always burned too hot in months one and two. Pace is critical.

Nutrition.

In an ultra, you eat before you are hungry and drink before you are thirsty. By the time you feel either, you are already too far behind to catch up. The deal equivalent is structured recovery. Founders need real time off the process, not weekends responding to data requests, actual recovery, built into the cadence from day one. The advisors who push back hardest on this are usually the advisors who lose deals in month seven. Recovery is not a luxury. It is fuel. It is about understanding your limits and when you need the time to recover. I encourage clients to disconnect, to protect their sleep, to keep a consistent pace. I have been known to suggest a weekend at a spa hotel, a long bath, an afternoon with nothing on the calendar, a short stint away to simply rest. The small rituals that return a person to themselves matter more in a deal than anyone wants to admit. Recovery is what keeps the momentum going.

The dark stretch.

Every ultra has a section, usually between sixty and eighty percent of the way through, where everything inside you wants to stop. Experienced ultra runners know this stretch is coming and have a protocol for it. They shorten their thinking horizon. They eat. They walk if they need to. They do not make any major decisions in the dark stretch, because they know their judgment is impaired. Deals have the same stretch. It usually arrives somewhere around the SPA negotiation, when diligence is mostly complete, the excitement of the early process is gone, and the close is still six to eight weeks away. The single most useful thing I do for clients in this stretch is tell them in advance that it is coming, and that they should not make any irreversible decisions during it. They need to focus on their objectives for doing the deal in the first place, and dig deep. The dark stretch always ends. The deal does not have to.

The crew.

Ultra runners have crews. People who hand them water at aid stations, who tell them their pace is good, who keep them honest when they want to quit. The crew is not optional. It is the difference between finishing and not. Founders in deal processes almost always under build their crew. They tell their spouse not to worry. They keep their leadership team in the dark. They lean on the advisor and nobody else, because they think they can carry it themselves. The strongest deal teams I have worked with are the ones where the founder has three or four people who know exactly where the deal stands and whose only job is to keep the founder upright. A spouse who knows when to stop asking how it went. A close friend who will pick up the phone at ten on a Tuesday night. A leadership team member who will quietly hold the line on operations so the founder can give the deal its due.

Coda

Deal fatigue is not overcome by the strongest party in the room. It is overcome by the party that recognized the signs of fatigue first and adjusted to it. The buyer who reads the founder's flatness on a Tuesday call and gives them a week of breathing room before sending the next round of comments. The advisor who notices the lawyer's redlines are getting sharper than the situation warrants and calls a pause. The founder who recognizes the dark stretch when they are in it and refuses to renegotiate a clause they would have accepted six weeks earlier.

The general mechanics of an M&A deal are knowable. The terms are negotiable. The price, eventually, is the price. What is not knowable in advance, and what almost nobody trains for, is the endurance event sitting underneath all of it. The deals that close cleanly are the deals where someone in the room understood that, and ran the process the way an experienced ultra runner runs a long trail race. With respect for the distance, attention to the signals, and a protocol for the dark stretch.

Recognize the fatigue early. Adjust before you have to. Finish the race (or deal).

Reece Tomlinson is the founder and CEO of RWT Capital and the author of Uncommon Capital.

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