Tony Hsieh passed away in December 2020 in a house fire. As the details come out, hopefully his life will also help entrepreneurs find their work/life/play balance.

I never met Tony but his impact and legacy are profound. The DailyMail recently published details about the accident that took his life.

"Shoe magnate Tony Hsieh's drug abuse was growing fast at the time of his death, has learned exclusively. And friends fear that his use of the laughing gas nitrous oxide and his love of candles could have caused the fire that killed him. 'In recent months the nitrous oxide had become as important to Tony as his alcohol,' one close colleague said. 'And Grey Goose vodka was his best friend.'"

Reading the article, I couldn’t help but think of a passage in my third book The 10-Year Overnight Success – An Entrepreneur’s Manifesto: How WatchMojo Built the Most Valuable Brand on YouTube (proceeds will go to the newly formed WatchMojo Foundation). It’s really lonely being an entrepreneur, Tony was known for saying “if half of the marriages end in divorce, and half of married people are unhappy, I don’t like those odds.” Statistically, sure, I get that… but I will just add that having a supportive spouse is probably the most under-rated ingredient for having success as an entrepreneur. Remember that line “Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t.” That doesn’t mean any of those years are easy.

Of Vice And Men

For creative and driven people, vices are as much about being happy as they are about tuning out the pressures of stress of our daily lives.

These days a lot of entertainers and businesspeople take great care of themselves and put their health first. Similarly to athletes, many realize that a balanced lifestyle can add many productive years to their career. That said, way too many turn to vices both for creativity and for escapism. For some it’s harmless, for others it’s not.

In April 2013, Business Insider ran a story about an L.A. based entrepreneur named Jody Sherman who took his own life. His company, Ecomom, experienced financial difficulties and shut down a few short weeks following his passing. 

To be crystal clear, there’s nothing to suggest that Sherman experienced any substance abuse, and the motivation as to why he took his own life can’t be confirmed as he left no letter explaining why he did what he did. However it’s suspected that Sherman couldn’t cope with the pressures of running a startup, and it’s thought he took his own life as a result of the challenges and expectations that come with starting a business and trying to meet investor expectations. While it’s important for people to be honest and candid with others, it’s even more important to be candid with oneself.

When reading about Sherman, I thought a lot about depression, addiction, abuse, and excess of all kinds. Saturday Night Live writer Fred Wolf stated that, “no one goes to Hollywood for the right reasons,” citing rough childhoods, abusive personalities, a need for attention etc. Similarly, these types of people who venture into business tend to do so to achieve success, power, respect, or even fame and wealth. While there may be hints of altruism, there can be a lot of unhealthy motivations too. 

Entrepreneurship is hard. We read about the successes, but we rarely hear about the failures. It may very well be easier to win the lottery than to get rich by starting a business. I don’t know anyone who has experienced success without having faced their fair share of adversity. Indeed, when we read about the successes, we oversimplify them and skip through the more challenging parts, but we also don’t read about perpetual failures. We’re conditioned to think that eventually, after a series of setbacks, even the Washington Generals will eventually prevail against the Harlem Globetrotters. 

The famous Greek philosopher Plato argued that an ideal society consisted of three classes of people: producers (craftsmen, farmers, artisans, etc.), auxiliaries (warriors), and guardians (rulers). In a world where everyone thinks they are meant to be an entrepreneur, this leaves things in a state of disarray. According to his logic, I had no business starting a business in my early twenties.

Recently, we have seen startup founders encouraged to fail fast and move on to their next iteration, in turn creating a culture of celebrating failure. Truth be told, I was torn on the movement. For one, I don’t think that success is an inevitable outcome. For every singular success story, there are countless failures. That’s just plain reality. Misleading individuals to believe that failure will eventually lead to success is disingenuous. That said, when people ask about WatchMojo,  I tell them that, we ran out of ways to fail. But that’s mostly out of modesty, since even when we were a money-losing insolvent operation we had a lot to brag about. At the time, I was urging people not to necessarily fail fast and pivot, but rather to think long and hard about a given opportunity and stick to it instead of jumping on a fad and moving on quickly. I also felt that too many people were drawn to entrepreneurship when they had no real business (or interest) in doing so. Entrepreneurship isn’t an elitist club, but rather it’s for those who can handle pain, rejection, and overcoming self-doubt. If you end up caring more about what others think of you than what you’re trying to accomplish, then you’re bound to let their negativity drag you down into a dark abyss.

When you finished a day’s worth of meetings which were capped off with one rejection after another, I wish I could tell you that I (and other entrepreneurs) would hit the gym, sip on some herbal tea, meditate, and sit around comparing yoga stances. The reality is different. Many of us turn to vicesbe it drinking, smoking, drugs, or engaging in risky or deviant sexual behavior. 

I’m fortunate that I kept my drinking to a somewhat reasonable level. I never woke up needing a drink, rarely drank before the evening, and never woke up thinking I couldn’t go to work that day. But hearing recovering alcoholic actor Rob Lowe talk about those who can’t simply have just one drink, I’d be lying if I said I didn’t know what he was talking about. 

I’ve never had just a drink. But thankfully, I’ve also never found myself in Alec Baldwin’s shoes, driving around with Sauvignon Blanc in a fountain cup with some ice, getting pulled over by a cop while thinking, guess it’s just another Monday. Growing up in Montreal also didn’t help matter much. For one, it’s the smoky ashtray of Canada. Secondly, the legal drinking is age is eighteen so most people from drinking habits early on. And third, drinking during a business lunch is commonplace here. 

In America it’s different. Sure, you watch Mad Men and think that people have triple martini lunches—and no doubt in some circles they do—but by and large, lunches were pretty dry and having more than a drink makes you stand out. One time, in July 2010 I met Podell for lunch at Aleo on West 20th street and Fifth Avenue. He was running late so I ordered a beer, and over the course of a very long lunch I had two glasses of red wine. It was nothing scandalous, but when I met him again at the Next New Networks’ office, he gave me a good ribbing. When their office manager greeted me and asked if I wanted coffee or water, Podell proceeded to shout out, “get him a glass of wine!” 

That’s when I thought, I fucking love this guy, and meant it. 

However in the evenings, New York turns into spring break but one where everyone can afford the drinks. All of the drinks, and then some. While such behavior is expected with entertainers, it’s accepted and par for the course in the business world too. Conferences let the taps flow freely at the end of the day in order to retain attendees, and drinking is the lubricant that greases the wheels in sales. 

Despite everything, I was fairly tame. I would also only smoke at social gatherings, never tried serious drugs, and was too in love with my wife to want the hassle or drama that came with cheating. But to hang out with fellow entrepreneurs and executives is like participating in the deviance Olympics. 

Spending an ungodly amount of time in airports also doesn’t help, especially if you think that planes will fall from the sky each time you’re waiting to get on one. 

“Want another drink?” 


“Shall we make it a double for an extra few dollars?” 

“Why not?” 

The soundtrack of an airport bar.

Yet if you asked anyone at the company, my family, or people I got to know in the industry, they’d tell you that I was an optimistic and happy individual. And, for all intents and purposes, I was. Yet the fact remains that from the very first day I launched WatchMojo to even now, there’s a tendency to feel depressed and alone. Entrepreneurship is often a solitary venture, and I was fortunate to have Christine by my side, but it often felt like I was trying to find my way out of a darkened maze. 

To write this book and not at least address this would have been dishonest.

Note: Proceeds of my books go to the newly formed WatchMojo Foundation, which support many causes including mental health and suicide prevention.