On a blustery May afternoon in 1954, Roger Bannister, a full-time medical student who trained on his lunch breaks, lined up on a track in Oxford. For decades, the four-minute mile had stood as the ultimate barrier in middle-distance running. Coaches, physicians, and sportswriters alike suggested it might be beyond human capacity. Yet Bannister, pacing himself to the second and leaning into the final straight, crossed the line at 3 minutes 59.4 seconds.

The world erupted. Within six weeks, an Australian, John Landy, bettered Bannister’s mark. Within a few years, a dozen others had done the same. It is tempting to conclude that the barrier had been “all in the mind” and that, once one man broke it, the floodgates opened.

But that is only part of the story. Seventy years later, in a world of far better tracks, shoes, nutrition, and sports science, fewer than 1,500 runners have ever accomplished what Bannister did that day. Seeing that it was possible didn’t make it universally attainable. It still required extraordinary physiology, relentless preparation, and favorable conditions.

That distinction — between possible and personally achievable — is crucial for business owners considering a transition. Again and again in my decades of advising entrepreneurs on mergers and acquisitions, I’ve seen the lure of the record-setting deal skew expectations. A single headline-grabbing multiple or a friend’s tale of a “once-in-a-lifetime” structure becomes the benchmark to beat. It’s as if every owner approaching a transaction expects to run their own four-minute mile.

Owners who let that kind of comparison drive their decisions often stumble over the same four misreads. Each has a parallel in the way an athlete can misjudge the challenge ahead.

The Market Misread

In most sectors, businesses are valued as a multiple of EBITDA, yet that figure is not as uniform as the shorthand suggests. Buyers pay premium multiples for companies whose cash flow is predictable and transferable: diverse customers, low key-person risk, good systems, clean books, and resilient margins. Businesses lacking those attributes trade at discounts — sometimes steep ones.

An owner who focuses on an “industry average” multiple or on the outlier paid for a better-positioned competitor is like a runner who trains for a flat, calm, sea-level oval only to discover the championship race is at altitude with a headwind and two hilly turns. The course conditions matter, and so do the unique features of each enterprise.



The strongest sellers know where their business sits on that spectrum and either improve its fundamentals in advance or accept that the market will price accordingly.

The Headline Misread

There is a well-worn investment-banking story about an owner who turned down reasonable bids for years, then finally got an offer that thrilled him. As he walked the buyer through his plant, he kept saying, “This is far better than any other price I’ve seen.” The buyer smiled and replied, “We haven’t discussed the structure yet.”



Many owners learn the hard way that what looks like a record price in a press release can be far less attractive once it is parsed into earn-outs, deferred payments, contingent notes, and performance claw-backs. All-cash at closing at a middling multiple can often beat a headline number that depends on future events the seller cannot control.

Bannister’s achievement was defined by the stopwatch, not by the newspaper headlines the next day. Business owners need to be equally clear-eyed about what counts — net proceeds and timing — rather than bask in the ego lift of a nominal price.

The Datapoint Misread

Human nature favors single points of “proof.” One extraordinary year becomes the assumed run-rate. One peer’s outsize multiple becomes the baseline expectation. One friend’s favorable deal terms become the demand at the table.

But valuation and structure are never dictated by anecdotes. They rest on sustained performance, business risk, and strategic fit for a particular buyer. Over-reliance on cherry-picked comparisons can undercut credibility, which is one of a seller’s most important assets in negotiation.