The Entrepreneur and Mental Health (Part 1): My Journey

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The Entrepreneur and Mental Health (Part 1): My Journey In The Trenches

Generally speaking, the average person is not fully aware of the emotional toll that entrepreneurship (or any other type of leadership, for that matter) can take. This could be due to the fact that most leaders tend to be uncomfortable with the idea of vulnerability, and instead choose to “shield” their stakeholders from the inevitable worries, doubts, and hesitations that they feel on a regular basis. Perhaps it could be due to the fact that the average person is so focused on the rewards of leadership (high compensation, decision making authority, and so on), that they ignore the price that leaders often have to pay to attain those rewards. Or perhaps the average person doesn’t particularly care: Why feel sympathy for the CEO (of all people) when their own roles are characterized by stress, uncertainty, low wages, or other worries?

Regardless of the reason why, and without delegitimizing any of the very real challenges that come with non-leadership roles, the fact is this: Nobody knows what it’s like to be a CEO or Entrepreneur unless you’ve been one. Full stop, no exceptions. Not the employees, not the management team, not the Board, and not the investors (unless individual Board members or investors have been Entrepreneurs or CEOs themselves). There’s a very practical implication of all of this: It’s lonely at the top.

This was certainly my experience as both an Entrepreneur and CEO over the past 10 years, and has been the experience of countless others. Throughout my tenure as a CEO, I came to learn that very few people could relate to the personal and professional challenges that I was constantly juggling, including my friends, family, and spouse (through no fault of their own, and in spite of their best efforts).

Though it’s come a long way over recent years, our collective degree of understanding, awareness and discussion surrounding issues of mental health is still sorely lacking. In my opinion, this is especially true of the mental health of Entrepreneurs and CEOs. This could be because leaders are expected to always be the unshakeable hand at the wheel regardless of the challenges that inevitably arise. It could be because stress, loneliness and pressure are viewed as “part of the job” for leaders. Or it could be because the depiction of Entrepreneurs and CEOs in the media don’t exactly paint them as characters worthy of genuine sympathy and understanding.

My own mental health journey as an Entrepreneur has taught me things that can’t be learned in a textbook. In sharing my story (and the associated lessons) with you, my hope is that, if you’re a leader experiencing feelings similar to those which I felt, you’ll feel less alone and learn from the things that worked and didn’t work for me. If you’re a leader who is not experiencing any of these difficulties, then I hope I can play some small role in keeping you in that healthy and balanced place.

In this blog post, I provide you with a brief summary of my own mental health journey as a leader. My goal isn’t to provide you with an exhaustive account of my journey, but rather to simply discuss it publicly. After all, if I don’t do my own part to contribute to the discussion around the worries, thoughts, and fears that Entrepreneurs and CEOs face, what right do I have to lament that it isn’t being discussed enough more broadly? This will be my only blog post solely about me. It will be the less practical of my two posts on mental health, but one which I hope you agree is still worth reading nonetheless.

In Part 2 of this series on mental health, I get much more tactical, and provide you with a list of the lessons that I’ve learned to deal with (or prevent, as much as possible) the mental health toll that entrepreneurship (or leadership, or success) can take.

Before I begin, let me speak to those readers (presumably those who have never been an Entrepreneur or a CEO) who, at this point, may be rolling their eyes, preparing to sarcastically play their tiny violins in sorrow for all of the powerful, well-compensated, and privileged CEOs and their attendant problems:

  1. You don’t understand. You can’t understand. I don’t (and can’t) blame you for not understanding
  2. Although this is written for the CEO, I invite you to read it nonetheless, and take this opportunity to better understand what your boss, CEO, friend or family member may be dealing with right now.


I became an entrepreneur in 2012, the same year that I graduated from Harvard Business School with my MBA. During my second year at Harvard, I raised a small private equity fund to help me search for, acquire, and subsequently operate a single privately-held business in North America. By 2013 I had found the business that I wanted to buy, and on January 8th, 2014, I completed the purchase of the company, making me the 27-year-old CEO of a multi-million-dollar private enterprise. Prior to my tenure as a CEO, I hadn’t managed as much as a secretary in my entire career. I was an Analyst working in Private Equity, with my excel responsibilities (read: a lot) far more important than my people management responsibilities (read: none).

Like so many entrepreneurs, the pressure that I put on myself to succeed was enormous: After all, I raised money from investors to help me buy the business, and the unfortunate reality of having investors is that at some point, they need their money back. What’s more, because I viewed these investors as people who truly believed in me (and who made a financial commitment to me to reflect that belief), I felt a tremendous personal burden to them. Because my “mandate” was effectively to buy a company, run it for a number of years, and subsequently sell it, I also managed to convince myself that my entrepreneurial journey was an incredibly binary one: Either I would make money for my investors, or I wouldn’t. In this way, success and failure felt to me like a very black & white proposition, with no grey in between. In light of my “mandate”, I told myself that I had approximately 5 years to either succeed or fail. On my first day on the job as CEO, as somebody who had never managed as much as a lemonade stand in my entire life, deep in my gut I often felt like failure was the more likely of the two outcomes.

The weight of this fear of failure, compounding daily for my ~7 years as CEO, grew to weigh on me considerably, though in many ways I was never really consciously aware of it. This was particularly true for me, because candidly, I had never really failed at any material undertaking (personal, professional, or academic) in my entire life at that point. This might sound arrogant of me to say, but it was objectively true. Somehow, the fear of failure is much worse for people who have never truly experienced failure in their lives.

From the outside looking in, everything looked great: In my first 5 years as CEO, we doubled both revenue & headcount, and achieved a 14% compound annual revenue growth rate. We were ranked as one of Canada’s 500 fastest growing companies between 2014-2017. We were ranked as one of Canada’s best places to work for 4 consecutive years between 2017 – 2020. I had a 100% CEO approval rating on We had roughly tripled employee engagement since we started measuring it in 2015. And yet, internally, for some reason I never allowed myself to feel the weight of those accomplishments. I foolishly told myself that CEOs must always be even-keeled, never getting too high and never getting too low. Later, my therapist illuminated for me that what I had actually been doing was allowing myself to feel all of the lows, but never allowing myself to feel any of the highs. Behind all of the growth, company success, and external awards, over my 7 years as CEO I felt all of the emotions below at different times. Sometimes they were felt at a conscious level, though most of the time I’d classify these thoughts and emotions as mostly subconscious. Only now, after having sold the company, do I have the clarity to say that each of these were very real struggles for me:

  • Imposter Syndrome: This is loosely defined as “a collection of feelings of inadequacy that persist despite evident success[1]. Particularly in my first few years as a CEO, when I had less confidence in my abilities, I couldn’t help but regularly feel like a bit of an imposter: What business did I have being a CEO given my age and complete lack of experience? Many of the things that the business was requiring of me were things that I had no experience in dealing with. Plus, I made more than my share of mistakes. I took all of those mistakes as evidence that I didn’t know what I was doing (and of course, paradoxically, I never took stock of all of my accomplishments as evidence that I did know what I was doing).
  • A “Ticking Clock”: As somebody who had investors (though of course not all entrepreneurs do), I managed to convince myself that I only had approximately 5 years to improve the company’s financial and operational standing before selling it, as a 5-year investment hold period is generally considered to be a loose rule of thumb in the private equity ecosystem. Each day that passed without overwhelming evidence of success felt to me like another day closer to potential failure. As mentioned above, for me, failure was an incredibly frightening potential outcome.
  • Treading Water Instead of Swimming: Though the company that I acquired had plenty of merits (otherwise I wouldn’t have made the biggest bet of my entire life in purchasing it), it had plenty of problems too, that in my view had to be addressed before we could pursue truly sustainable growth. Of course, fixing these problems took longer and costed more than I had originally anticipated. In my specific case, we spent years doing work that felt more like untying a giant knot than making true, forward-looking progress. Another way to look at it was to equate it to the difference between treading water and swimming forward. As somebody who based (and, if I’m being honest, still bases) a lot of their personal self-worth around the concept of achievement, this was more difficult for me than you might imagine. My inherent need to achieve felt like it went unsatisfied for years, as my goal had never been to simply tread water, but to always swim forwards at an ever-increasing rate of speed.
  • Feelings of Wanting to Quit: I had never quit anything of real substance in my entire life. Most CEOs and Entrepreneurs don’t get to where they are by being people who easily give up on difficult tasks. And yet, there were days, weeks, and in some cases even months where I felt like giving up. This didn’t necessarily mean outright quitting for me, though sometimes it did. “Giving up” could have meant selling the company at a discount before it was truly ready to be sold. Or hiring in a new CEO to allow me to play more of a “passive owner” role. In any case, just the thought of quitting created a huge degree of cognitive dissonance for me: For substantially my entire life, I viewed myself as a walking example of somebody who could persevere through literally anything. And yet, suddenly, I was having thoughts of quitting and doing something else. This cognitive dissonance (essentially having thoughts that seem to be in direct conflict with each other) can take a large mental toll, even if you’re not explicitly aware of it.
  • Trying to Pursue “Balance”, but Ending up Feeling More Tired: Many mentors of mine gave me wise advice about company leadership being a marathon, and not a sprint, and to adjust my behaviors accordingly. More specifically, they’d encourage me to find time for exercise, family, and other personal interests. Whenever I did (misguidedly) try to pursue balance in my life, strangely what often resulted was me feeling a greater sense of exhaustion. Instead of pursuing a more sustainable lifestyle, like any good type-A overachiever I simply just tried to do more, and justified it to myself in the name of “balance”: I tried to exercise 5 times/week at 6:30am. I tried to be home in time for dinner every night. I’d try to never work on weekends. I started meditating daily. Of course, the result of all of this was that my pursuit of “balance” (or, more specifically, my own foolish way of trying to pursue it) actually made me feel more tired. I was simply just trying to cram more into any given 24-hour period.

In late 2018, myself and my management team saw an opportunity to partner with a Private Equity firm, which would have seen us sell a majority stake in the company to them. Privately, I thought that this was finally my opportunity to succeed, and to bring this journey of relentless stress to an end with a successful outcome for both myself and my investors. Moreover, we thought that the Private Equity firm could legitimately help to further grow the business, thus benefitting my management team and employees. After many months of exhaustive due diligence, and a few conversations where my wife & I would discuss what we’d do with our newfound freedom, the transaction fell apart in its late stages. I dedicated myself to this transaction for almost a full year of my life, and suddenly had nothing to show for it, other than a business that was now in a state of stagnation as it hadn’t received much of my time or attention during that period. Suddenly, the prospect of failure for me increased.

Of course, I convinced myself that a CEO should be steely, unmoved, and impervious to disappointment. Literally the next day, I went back to work and actually begin instituting several major changes in the business in response to some of the potential issues that the buyer identified throughout the course of their due diligence process.

What I didn’t realize though, was that the transaction falling through was the straw that finally broke my back: Years of relentless stress, no self-care, no sense of balance, my refusal to ask others for help, a compounding fear of failure, and dealing with problem after problem (as they say, “shit rolls uphill”) had finally taken its toll on me. A few months later, I was diagnosed with burnout. Though I had always thought that burnout was nothing more than a synonym for being tired, I came to learn that it was a real clinical diagnosis that required treatment.

As I began that treatment, learning more about how to make my entrepreneurial journey a more sustainable one, the universe had other plans: Enter 2020. I had barely begun my recovery, when suddenly I was responsible for leading a company through a once-in-a-multi-generation global crisis. We had to lay people off. We had to close our office. We had cash flow concerns for the first time ever. We instituted salary reductions for everybody in the company, including myself and my management team, who took the largest reduction of anybody. Worse, like so many other parents, both my wife (who held a demanding job at the time) and myself were forced to both work from home, and simultaneously watch over our active daughter of 18 months, without any external help. Me being me, my only response was to do more: I began giving my employees daily email updates. I began doing weekly Q&A sessions where I’d had to answer questions about the company’s survival for the first time. I had weekly calls with my Board to keep them updated on the state of the company. I met with my CFO every morning to review our working capital position.

What I didn’t realize was that I was building all of these new responsibilities on top of a shaky personal foundation of burnout, and a complete absence of self-care and balance. As a result, my burnout evolved into something else: Around May or so, I was diagnosed with anxiety and depression. I was having trouble sleeping. I found myself on medication to regulate my mood. I was having a hard time having simple conversations with my employees that I never would have thought twice about in the past. However, the worst thing of all for me was simply receiving the diagnosis – it shook me to my core. I simply couldn’t wrap my head around the fact that I, of all people, was depressed and anxious. It went against literally every ideal that I had had of myself. I never imagined, not just in my lifetime but within many lifetimes, that I was somebody who could fall victim to anxiety and/or depression. Suddenly, my current reality was now in stark contrast to the ideals that I had held of myself for substantially my entire life.

As I’ll discuss further in Part 2 of this blog post, I ended up stepping away from my role as CEO in July of 2020 after almost 7 years at the helm, to focus my energy on my own personal recovery. I felt like I couldn’t be the leader that the company needed me to be until I was in a better mental headspace. We were fortunate in that only a few months later the company was successfully sold to a larger industry competitor, finally giving myself and my investors the win that I had been dreaming about since the day I raised my small Private Equity fund in Business School in 2012.

Though I’ve made many strides since that point, mental health is still something that I work on and deal with every day. I am no longer dealing with depression, but am still dealing with anxiety, and am still taking medication to help me deal with it. It’s worth noting here that the sale of my company, and the financial windfall that resulted, was not the thing that expedited (or even aided in) my recovery. In fact, studies have shown that selling your business is actually more likely to make you depressed, not less. Instead, it has been a thoughtful, deliberate, and concerted effort focused on self-care that has been my most important recovery tool.

Though the journey has been very difficult, I’ve come to see a silver lining: Based on the mistakes that I made, I’ve learned so much about what I could have done (or, more accurately, should have done) to prevent me from getting to that difficult spot in the first place.

Sharing these lessons with you is what I attempt to do in Part 2 of this post.


If you’re interested in learning more:

The Hard Thing About Hard Things, written by Ben Horowitz, co-founder of venture capital firm Andreesen Horowitz, is perhaps the only business book that I’ve ever read that accurately depicts what it’s truly like to be a CEO. In my opinion, it’s required reading for all current and aspiring entrepreneurs and company leaders. Though Ben’s tenure as CEO of Opsware was ultimately extremely successful, this first-hand account of his journey shows that what you see on the outside (of both a company and an individual) isn’t always representative of what’s happening on the inside.

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