I recently sat with a client who had built a business that generates hundreds of millions of dollars in annual revenue. By any measure, he had won. It throws off tens of millions in profit each year and is worth hundreds of millions of dollars. And yet, when I asked him how it felt, he told me he was always worried it could all be taken from him at any moment.

I found this remarkable. Here was a man who had built something wildly successful, and the thing that haunted him was the notion that it might vanish. But the longer I sat with it, the less remarkable it seemed. He was not an outlier. He was describing something that nearly every serious business owner carries, something I struggle with myself, and something almost no business owner can name.

Like you, I have paid for my "success" in blood, sweat, tears and a lot of sleepless nights. I started RWT at a desk in the condo I was renting nearly ten years ago... a desk just wide enough to fit one monitor, where I would spend twelve to sixteen hours a day until, years later, I could finally afford to rent an office. The challenge with starting up an investment banking firm is that it takes a track record to get clients, yet you cannot get clients without the track record... so starting out is very precarious. For nearly three years straight I kept up a mixture of crazy long hours, seven days a week, and a ruthless travel schedule that continues to this day. (I am probably one of the biggest consumers of Sephora under eye patches in the country, thanks to the gruelling early starts flying from the West Coast to Toronto.) But more than the hours, there was the year I almost lost the business. I did not have enough clients in the hopper, interest rates spiked in 2023 and many M&A deals collapsed overnight, and things went south... In fact, I had to sell real estate I had intended to hold for many years to come, simply to keep my team employed, and borrow money to pay the bills. All of it to get to where I am now. Like you, I built up the habits that support this grind of a lifestyle, and even though some may look at me from the outside and call it success, what it took to get here is the scar I carry, and those habits are ingrained in me. These habits can make you a success, but they have downfalls too... what Robin Sharma calls the dark side of genius.1 They can lead to messy private lives where happiness is never really achieved.

Building a business to the point that it is worth millions of dollars is genuinely hard, and very few people ever do it. According to Verne Harnish's Scaling Up (a great book if you haven't read it), fewer than 5% of companies will ever exceed $1M in annual revenue, and only about one in ten of those will ever cross $10M.2 Run that through the arithmetic of an exit... a 20% EBITDA margin and a 5x multiple... and it means that fewer than half of one percent of companies, roughly one in 250, will ever sell for $10M or more.

At RWT Capital, this echelon of owners, the ones who accomplish the absurdly challenging feat, is the world we live in. We tend to look at transactions around that $10M mark and beyond, which means I spend my days with the owners who have made it there... the ones who put in the blood, the sweat and the years required to build something of real size. Every one of them carries the scars. And scars, by definition, are the mark of a cost that was paid.

Some of that cost is easy to name, because every owner can point to it. It is the year you nearly lost everything when things did not go to plan. It is the countless hours worked for almost no money just to keep the doors open. It is the personal guarantee on millions in debt, or the mortgage you put back on your house to make payroll. Less obviously, it is the kids' games you missed because the hours had to be worked, the weekends and friendships you gave up because you could not yet afford to hire the help, and the pastimes and hobbies you once loved that quietly fell away as the business grew. It is the employee you poured everything into who left without warning and left you with a big hole in your team. It is the supplier who raised prices overnight after years of loyalty. Every owner I have worked with has their own version of this list, and no one is immune.

To survive it, you had to build a level of resilience and optimism that people who have never owned a business simply cannot relate to. The belief that next quarter will be the turning point is a real and necessary state of mind... and it often carries you through many, many quarters before it finally comes true. This is the only way through the chasm of building, and there is no way around it.

But there is a deeper cost underneath all of that, and it is harder to see. It is the inability to truly switch off. It is a work ethic so relentless that even at rest you are like a stallion standing in the barn, muscles ready to run at the smallest signal. Most profoundly, it is the inability to be present, because for as long as you own the business it will, in some way, grip you. Its success has become your focus, and somewhere along the way it may have become your identity.

And here is the cruel part. The struggle becomes addicting. The ups and the downs, the wins and the losses, add an intensity to life that is almost impossible to replicate and almost impossible to explain to someone who has never felt it.

So you can own your business... but the real question is whether the business owns you.

Ask yourself... how many vacations have you been on where you brought your computer along, or checked in with your team when you should have been present? How many family dinners have you sat through, physically present but mentally replaying a problem at work you are dealing with? I know I have... I have made a habit of going to Hawaii every winter, and each time I swear I won't do any work... yet each time I invariably do. Then go deeper and ask yourself: what do you do for fun? Most business owners I speak with have a hard time answering that one in earnest... even the things they once loved to do can get clouded by the business.

In my experience, this is exactly why so many owners of companies worth millions struggle so badly with the idea of selling. They are chained to the thing they built. And the only way to break the chain is to sell... to convert the years into the actual gains, and to be free of the weight, real or imagined, that you have carried on your back for so long. But breaking that chain asks something hard of you. It asks you to give up a part of yourself... perhaps the part you believe defines you.

This is not always the easiest thing to read. Even though I advise business owners on this very topic, I too have a hard time when I am reminded that the company, and being its CEO, is not actually my identity. It is a surface-level identity, not the real me. And yet there are times when I catch myself thinking this life is actually really great, so why would I ever want to change it? Yes, the demands are relentless, and yes, I have a hard time switching off, but being a business owner is exciting, powerful and, if I am honest, good for the ego. Why would I need any more than that?

It is easy to think that because you own the business you have freedom, but the reality is far from it. Every one of us business owners is chained to the company, whether we realise it or not.

This is the struggle, and it clouds everything. You stop seeing the forest for the trees. You lose sight of the fact that you are holding a business worth millions, an asset that could change your life and your family's life forever, because the patterns you built to survive are so deeply set in you that any other life feels unimaginable. The gate to the cage is standing open... and still you cannot picture walking through it.

Almost every owner I have worked with has told me the same thing after selling. They wish they had sold earlier. Only one did not say this... he broke his non-compete, landed in a very substantial lawsuit, and I would strongly advise against following his example. The rest described the sale as the best thing that ever happened to them. They were finally free to live, to become the people they wanted to be, to have adventures, to be present.

The smartest owners see it before they sell. They recognize that there is a forest behind the trees... that the business is not the destination but the unlock button for a far better existence. They understand that the traits they forged to build the company were a necessity for that season of life, but they no longer need to be ruled by them. They are allowed to be grander than the struggle. They are allowed to live bigger, on their own terms, with many millions of dollars at their disposal. They can be fully intentional with what they want out of life.

Being able to see this struggle is where it all begins.

If you are reading this, you are likely aware that the struggle has a cost. But you are likely just as aware that the opportunity, for a better and more intentional life, is sitting right there in front of you. And if you have come this far, you are already doing something that few business owners ever do... thinking with intentionality about your future, and about what an unlocked business could mean for you, your family and your legacy. That is what the rest of this book is for. Naming the struggle is only the first step. Everything that follows is about how you actually walk through the open gate.

Reece Tomlinson is the Founder and CEO of RWT Capital Corp. and the Author of Uncommon Capital.

Footnotes

1. Robin Sharma, The 5AM Club: Own Your Morning, Elevate Your Life, HarperCollins, 2018. Sharma introduces "the dark side of genius" through his character the Spellbinder: every human gift carries a downside, and the very quality that makes a person exceptional in one area can make them a misfit in another, which is why many great performers have messy private lives. ↩
2. Verne Harnish, Scaling Up: How a Few Companies Make It... and Why the Rest Don't (Rockefeller Habits 2.0), Gazelles Inc., 2014. Harnish estimates that of roughly 28 million US firms, about 4% ever exceed $1M in annual revenue, and only about one in ten of those (roughly 0.4% of all companies) ever reach $10M. The same figure is cited widely, including by Compass Point, which puts the share of US companies reaching $10M+ at about 0.4%. Note that these estimates use a denominator of all US firms, including sole proprietors and non-employer businesses, which pulls the percentages down. Studies that look only at established small businesses report higher rates. The JPMorgan Chase Institute, for example, found that roughly 9% of small businesses in its sample reached $1M in revenue within five years. ↩

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