I built my first company at twenty-one, installing LCD and plasma displays into big box stores and bank branches across the country. By thirty-five I’d flexed into fifty employees, three kids born inside of three years, and a business that from the outside looked like the best thing that had ever happened to me.

From the inside, I’m not sure I could have told you how I felt. I just knew I was exhausted, physically, emotionally, spiritually.

My parents had immigrated from the UK in the 1970s, and my father worked the way a lot of first-generation entrepreneurs work: constantly, and mostly somewhere else. He built a good life for us. I don’t think he was ever really home for it. I made myself a promise as a kid that if I ever had children, I’d be the father who was actually there, not just present for the big moments, but for the ordinary Tuesday ones. And then I built a business that made that promise almost impossible to keep.

The wake-up call, when it came, didn’t come from a business review. It came from my mother’s hospital room. In the spring before she died, I sat with her for three days while she said the things you only get to say once. I’d spent years telling myself I’d make more time for the people who mattered as soon as the business could run without me. Sitting there, it was obvious how much of that time I’d already spent believing a lie, that the business needed me more than my wife did (we divorced not long after), more than my mother did, more than my kids did, more than I needed myself.

I didn’t know yet how to fix any of it. What I knew was that I needed someone I trusted to help me carry a company I could no longer carry alone, and that’s when Brad Chitty came into the picture, first as a consultant, then, within eight months, as my CEO and a shareholder in the business we’d built. Brad had been a CTO at Bell Gateways before this, the kind of person who reads a balance sheet before he reads a room, calm where I run hot. The first time he really looked at how I was running things, he said something like: this is brilliant, how the hell are you doing this on your own?

“

You’re not going back there, Simon!

I didn’t have an answer. Letting him actually run it was harder than I expected. I remember the day he caught me heading into the warehouse to do engineering work I no longer needed to be doing. He put a hand on my shoulder and said, “You’re not going back there, Simon!” My first reaction was something close to anger, it’s my company, and my second reaction, a few seconds later, was relief. He was right. As long as I stayed the guy fixing things on the floor, nothing he was trying to build upstairs could take hold.

I got on a plane to Boston that same day, for a hospital project I was designing on the other side of that decision, and somewhere over Lake Ontario it actually landed: I had just let go of something I’d been sure only I could hold. Nothing fell apart. If anything, everything got lighter.

That was the beginning of understanding something I now spend my working life trying to get other owners to see before it costs them what it nearly cost me: the tighter you hold a business, the smaller its future gets, including the parts of your own life that were supposed to be the point of building it.

A few years after Brad became CEO, we grew fast enough to attract real interest, including from an American M&A firm that invited the two of us to a boardroom in a hotel in Toronto to “talk strategy.”

It wasn’t a strategy conversation. It was a sales process, aimed entirely at us, and it worked. By the time we left that room, we’d committed to a $10,000 USD cheque due the very next day just to get the process started, and we wrote it. That cheque got cashed.

“

It felt exactly like what it was: a high-stakes timeshare pitch wearing a suit.

I’ve always made decisions fast, it’s a strength most days and a liability on others. Brad isn’t built that way. He’d been a CTO at Bell Gateways before he ever worked with me, and the man makes calculated, numbers-first decisions for a living. Watching him get swept up in that room the same way I did told me everything about how good those tactics were, and none of it made either of us feel better once we were back outside it. It felt exactly like what it was: a high-stakes timeshare pitch wearing a suit, run on two people who hadn’t been given a single fact yet about what our own business was actually worth.

Realizing it fast didn’t make getting out of it easy. We had a real fight on our hands to unwind the commitment to sell, it cost us the $10,000 and weeks we didn’t get back. What it also did was force us to get serious: we found the right advice, got strategic about what our business was actually worth and who should be at the table, and years later sold it properly, through a broker who developed a bidding strategy we have perfected today.

The fact that it got as far as it did still bothers me more than almost anything else in this story, that two people who’d built and run a real company for over a decade could be talked into signing away momentum on it inside a single meeting, before either of us had a real number in hand. That’s the moment I trace Freedom For Founders back to, more than any other. Not the exit. Not the warehouse. This one. Because it’s the moment I understood the danger isn’t only the pressure in the room. It’s the buyer on the other side of the table who does this for a living and knows exactly how to outmaneuver an owner who doesn’t, or the moment that shows up uninvited and forces a decision before you’re ready: a death, a divorce, a disease, a distress, a dispute. Any one of those can leave an owner vulnerable enough to sign something they’d never sign with a clear head and time to think.

I ended up selling that business at thirty-nine, the sale I mentioned a chapter ago, done right this time, years after that boardroom in Toronto. I wasn’t ready to retire, not even close, but the offer let me take my fifteen years of investment off the table on my own terms, with a clear head, and no risk, I didn’t look back.

What surprised me wasn’t the money. It was what came after it. I went from running a fifty-person operation to driving a cube van for Hope House in Guelph, delivering food and, on one particular day, a donation of diapers to a group of young mothers who reacted like I’d handed them something priceless. I remember standing in that parking lot in tears. I hadn’t cried at a boardroom table in fifteen years of business. It took delivering diapers out of a borrowed van to get there.

“

There is more of you on the other side of that business than you think there is inside it.

Most owners build an identity as tightly wound around their business as their equity is. I did too. What I didn’t expect was how much more significance I’d find on the other side of it, first as a volunteer, eventually as chairman of that same organization’s board, advocating for people the system usually looks past. It taught me something I now say to almost every owner I work with: the fear of what you’ll do with yourself after you sell is real, and it is almost always wrong. There is more of you on the other side of that business than you think there is inside it.

Put those three things next to each other and the shape of this company becomes obvious. I know what it costs to hold a business too tightly for too long. I know how close two careful, capable people can come to signing away years of work in a single high-pressure afternoon, armed with nothing but someone else’s urgency. And I know that the life waiting on the other side of a sale, done right, is better than almost any owner braces themselves for.

Freedom For Founders exists to make sure no founder has to learn any of that the way we did, by accident, under pressure, or too late to change the outcome. The Discovery Program exists specifically because of that boardroom in Toronto: so that by the time anyone puts a number or a deadline in front of you, you already have your own and you clearly understand your options. The 100% guarantee exists because I know exactly what it feels like to be asked to commit before you’re ready, and I never want anyone walking out of a meeting with us the way Brad and I walked out of that one.

Here’s the part of this story I don’t tell as often, and probably the part that matters most.

People in my industry have given this moment a marketing name, the Silver Tsunami, the Two Trillion Dollar Exit. Language built for a conference stage, all opportunity and no weight. I don’t use those terms. I call it a crisis, because that’s what it looks like once you’ve sat across from as many owners as I have.

We’ve connected with thousands of owners across Canada by now, and the pattern repeats itself often enough that I trust it. Owners who are too busy, too stubborn, too proud, too independent, and often too embarrassed to get real help, because they picked up the tools to build a business but were never taught how to run one. Many can’t read their own financial statements. Almost none of them have a real plan for how to exit. And plenty are slow to hand anyone the real numbers, including us, until they’ve run out of runway to fix what those numbers would show. Multiply that across a country full of owners aging out at the same time, and what you get isn’t a tailwind. It’s a crisis, and I’m not going to soften the word just to make it sound more fundable.

I don’t think I get to fix that by being the one person doing the work. I actually think trying to be that person is the exact mistake this whole company was built to warn owners against, the idea that nothing important can happen unless you personally hold every piece of it.

My father worked hard enough, for long enough, that I worked for him to see him. I promised myself I’d be different with my own kids, and by their account I’ve mostly kept that promise, my three kids and their friends call me “Father Greatness,” which is a ridiculous title I have never once asked anyone to stop using. What I didn’t expect is how much I’d want to extend that same instinct past my own family. The team I’ve built is a collective, an on purpose group of young entrepreneurial advisors and seasoned owners working together. Because a firm that’s all experience with no future focus, or all youth with no scar tissue, doesn’t serve owners well either. I’m training the advisors coming up behind me to sit across from a founder someday and do everything I do, including the parts that took me two bad decades to learn, without needing me in the room to do it. I hope you have the pleasure of meeting them and learning from them, as they will learn from you, two (2) experts with one common goal, setting you free.

I want to be blunt about why: I’m not interested in being indispensable. I spent a large part of my life being exactly that to a company that was slowly costing me my health, my marriage, and my time with the people I loved, and I’ve got a cashed $10,000 cheque and a fight I didn’t want as proof of what it costs to face a moment like that without the right people in your corner. I don’t want my name to be the ceiling on how many owners this company can actually help. I want there to be enough advisors who carry this the way Brad once carried me and my company that I finally admitted I couldn’t carry alone, so the crisis becomes something we actually make a dent in, not something I personally attended to one founder at a time until I ran out of years.

If I ever get to a point where I have nothing left to prove, I know exactly what I’d do with my time: more of this, more mentoring young people, building futures, setting founders free, so family and friends can experience living the life they worked so hard to achieve.

“

I believe I’m saving lives. Not just metaphorically.

But I don’t think I need to wait for that point to say the truest thing I know about this work: I believe I’m saving lives. Not just metaphorically. I’ve watched what an unplanned exit does to a marriage, a body, a family, and I’ve watched what a well-planned one gives back. It’s also not only about the owner selling, it matters enormously to me and to us who buys, whether the company lands with someone who sees the employees and the community it sits inside as part of what they’re taking on, not just the cash flow on a spreadsheet. Ninety-one percent (91.2%) of the companies in this country have somewhere between one and nineteen employees and turn over less than ten million dollars a year in Revenue. That’s the real market I work in, not the boardrooms, the real one, and moving that many owners toward a good ending instead of a rushed one is slow, emotional, really hard work.

It is also, without question, the most satisfying work I’ve ever done. Setting an owner free, properly, on their own terms, with a buyer who’s going to take care of what they built, alongside advisors I’ve had a hand in shaping, who’ve learned to choose empathy over economics the way I eventually did: that’s the mission, and it is entirely personal. I got out. I want that to be true for a lot more people than just me, and I don’t want it to require me personally to still be true twenty years from now. That’s my legacy.