This one is a bit different than my recent pieces. It is less about the mechanics of a mid-market M&A deal and more about what being a founder is really about... why we pursue the entrepreneurial journey in the first place. And maybe, more broadly, what this whole strange pursuit we call life is even about.

There is a book I love called Chasing Daylight by Eugene O'Kelly, the former CEO of KPMG. The outward premise is harrowing, and it was a deeply emotional read for me: in his mid-fifties, O'Kelly was diagnosed with a terminal brain cancer and given months to live. It is a masterpiece on learning to seize the moment, and I recommend it to anyone. But the thing that stayed with me was his pursuit of what he called Perfect Days from the moment he was diagnosed.

A Perfect Day, in his telling, was not a flawless twenty-four-hour period. Rather, it was a day built around the pursuit and collection of Perfect Moments. He broke the idea down into a handful of ingredients: a collection of hyper-focused moments rather than a blur of hours, absolute presence and total engagement with whatever was happening right now, a simplicity rooted in nature that stripped away corporate luxury in favour of things as plain as being outside, spontaneity over scheduling because the best moments were rarely planned, and finally a deep relational clarity... intentional, one-on-one time with the people he loved.

During the final three months of his life, O'Kelly estimated he had lived more Perfect Days than he had in the previous several decades as a high-powered global CEO.

To me, his realisation of the number of Perfect Moments he had lived is both beautiful and heartbreaking. Beautiful because he found it at all. Heartbreaking because he could have had so many more of those moments with the people he loved. In the book he describes the long hours, the back-breaking international travel, the relentless willingness to grind it out at work... none of it that different from most of the founders I know. Or, if I am honest, even from myself. And maybe some of us are simply wired this way. Or maybe it is the adversity many founders lived through in their formative years that leaves them unable to switch off, because psychological safety was never something we knew... but I digress.

All of which raises a question I keep coming back to. For a founder who has built a company worth enough to sell, retire, and live extraordinarily well on their own terms... why is the potential for that life so rarely seen for what it is? These are people who sit within reach of something 99.99% of the planet never will experience (substantial wealth, freedom and living on their terms). They could sell the business tomorrow and fund a life full of Perfect Moments, hopefully for many years to come, often with plenty left over to give to the causes they care about. And yet most founders shy away from the conversation entirely.

They treat the business as their legacy, a permanent fixture in their life, almost as if it will be waiting for them on the other side when they pass away. They choose the meeting, the grind, the trench over time with their kids, their grandkids, the epic trip with old friends, the generational property their great-grandchildren might one day gather at. Somewhere along the way they lose sight of why they worked so hard in the first place, and of what those years could unlock for them and their families. They choose what feels safe over the unknown of selling and actually living the life they were building toward.

Years ago we had a client who sold his manufacturing company begrudgingly, essentially because his wife was insisting on it. He fought us the whole way, putting up roadblock after roadblock to keep the deal from closing. At one point he demanded a transaction value well above market, which we managed to reach only by stacking on a series of vendor notes (including a ten-year VTB, which I would not recommend to anyone) and earn-outs. The structure left him with effectively no grounds to walk away... facing his wife, evidently, was the worse outcome. He was also one of the harder-working, more intense founders I have worked with, the kind who insisted on early-morning and late-night calls on a near-daily basis, weekends included. We once spent an hour on the phone with him on Christmas... something I would not do today, but at the time I was building RWT and we needed the deal to close. The headline transaction value came in just over $20m. The trouble is, the company had been worth somewhere between $12m and $15m for the previous five years. Once you account for all the contingent mechanisms we used to get above $20m, which was his condition for selling at all; the cash he actually walked away with on close was roughly what he would have received in a clean sale two or three years earlier. He held out, took on years of additional structure and risk, and bought himself almost nothing... except the time he lost getting there.

I share this because of what happened next. Within three months of closing, this same client told me that selling the business he had built from the ground up was the best thing he had ever done, and that he only wished he had done it years sooner. He was a visibly lighter, more relaxed man. Suddenly there was a home in California, a beautiful travel trailer he was taking to sites all over North America, and, most importantly, far more time with his adult children... the ones he had admitted growing distant from in the years spent building the company. He had started to taste the Perfect Day dividend that only selling well makes possible (or, I suppose, winning the lottery.).

So when I hear a founder with a company worth north of $15m tell me they need a few more years of growth before they will sell, I find myself asking the same quiet question. What will actually change? If you get $17m instead of $15m, what in your life is materially different? The honest answer, almost always, is nothing... nothing except the time you cannot get back, the moments with your family you will not get to have, and the Perfect Days you will never live. And to add insult to injury…the vast majority of these founders don’t actually grow their company during that period. They just prolong the status quo.

We have worked with clients who insist they cannot sell unless they hit a certain transaction value, the client above being one of them. More often than not, that number is tied to ego, to some number they have in their brain that signals they were a success, to a quiet desire to outdo other founders who have already sold. But as a woman who sells and buys businesses for a living, what I can tell you is that the only outcome worth weighing is what the sale means for the Perfect Days you intend to live. A client once told me the difference between selling for $10m and selling for $50m is that you can afford three Ferraris instead of one. But you cannot drive three Ferraris at once... so is there any real difference in the life you actually live? From everything I have seen, every client we have sold their business for many millions of dollars…the answer is zero.

There is a saying that life is a series of blinks. I did not really understand what it meant until I started watching my own children grow. Life moves fast. Building a business is an exciting, gratifying, rollercoaster of an adventure... but it is a conduit to something greater, and I would encourage any founder reading this to hold that in mind as they think about what comes next.

Reece Tomlinson is the founder and CEO of RWT Capital Corp. a boutique M&A advisory firm with offices in Kelowna, Vancouver and Calgary. Over 130+ mandates across 16+ countries, she has advised founders on the sale, acquisition, and capital strategies of mid-market businesses. She writes Uncommon Capital on the human side of M&A.

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