Entrepreneurship is hard in bad times, tougher in good ones.

“I’ve lost my mind to the game. Like Vincent Van Gogh. He dedicated his life to his craft, & lost his mind. That’s happening to me. But f*ck It. When that belts around my waist & my mother has that mansion... It will be worth it.” -- Conor McGregor

Last week, the use of artificial intelligence in a documentary on Anthony Bourdain led to some ethical discussions about filmmaking. This week would have marked Robin Williams’ 70th birthday. Williams – who had early stage Parkinson’s and struggled with depression and anxiety – died by suicide in 2014. If the news of Bourdain’s death surprised some, Williams’ shocked all.

Having covered depression through the lens of entrepreneurship, it’s clear that mental health’s impact on society will only become more crucial as more young individuals turn to entrepreneurship. Awash in capital, showered with investor interest, buoyed by a strong stock market, investors could care less about the mental health of the entrepreneurs they finance.

We’re hearing a lot about employees being burned out and quitting, but what about the bosses? CEOs face a uniquely challenging reality, but the mental wear and tear on founders is quite different, often times because we lack the support systems that corporations create around high-profile executives.

Like parents, we can’t really show our pain. We’re supposed to keep calm and carry on. Indeed, when leading a team you need to project positivity, setbacks – no, everything – happen for a reason. If only life were that simple. If I break down WatchMojo into 5-year intervals:

  • 2006-10 represented the early, lean, tough years;
  • 2011-15 we found product/market fit and experienced our rocketship years;
  • 2016-20 saw heightened competition, complexity, conflict before finding clarity.

The most recent 5-year period was our best financial years, but arguably the toughest on me mentally. The one constant has been my 100-hour workweeks going back to when I graduated from college. As 2021 signals the beginning of a new phase, it seems like what’s new is old and lately, I find myself frozen when trying to reply to the following types of emails I receive:

  1. a senior executive in my network looking for new challenges, at WatchMojo;
  2. a movie/TV/digital series production someone is asking us to finance/co-produce;
  3. a startup founder seeking financing;
  4. a philanthropic request of some kind.

The Pinnacle of Success is a Lonely Mountain

Incidentally, when my alma mater, the John Molson School of Business at Concordia included me on a list of fifty alumni to follow, I commented that my experience there was “both a source of tremendous positivity but also so much frustration & disappointment for how unjust, political, unfair organizations could be. As such, it prepared me for life!” Business is ten times harder, and the more success you have, the tougher things become on your mental well-being. Exacerbating matters is that the things that capture your success became less pertinent to other events that affect you emotionally, but your success prevents you from sharing the impact of those events.

Some find my candor surprising, but as Thomas Paine once said, “He who dares not to offend cannot be honest.” Be careful what you ask for, for truthfulness is boundaryless. 

The Dog Years of Entrepreneurship

Hold my beer, Costanza.

The first and second years of a dog’s life are equal to 15 and 9 years of a human’s life (with subsequent ones adding 5 each). My third book, The 10-Year Old Overnight Success, chronicled the ten first years of WatchMojo’s existence. The first five were brutally tough, including a meritless lawsuit and running out of money. After breaking-even in 2011, in March 2012 I wrote Get Rich or Die Tryin’ for TechCrunch, with “rich” being a metaphor whatever you chase – wealth, fame, power, success, respect etc.

Compared to the lean 2006-10 era, 2011-15 involved us finding product/market fit and enjoying our rocketship years. By 2016, I could have rode into the sunset and enjoyed the fruits of our labor, but ambition pushed me to chase growth, which was stimulating but draining and punishing psychologically. I’m not complaining, but as I now support the next generation of entrepreneurs, I find myself painting a realistic picture of what to expect in good, bad, and great times: it ain’t for the faint of heart, and with success comes more headaches and heartbreaks.

A Series of Body Blows

Five years ago in 2016, we got hacked. It wasn’t fatal, but it hurt us and made me paranoid. 

In 2017, we recruited four senior executives to professionalize the management bench, aspiring to evolve “from the Montreal Expos to the New York Yankees.” The executives we brought on – Patrick Lauzon as COO, John McCarus as CMO, Matt McDonagh as CRO and David Massė as CFO – were all seasoned veterans who had a ton of industry experience. They helped further develop my co-founders, whom I’d recruited out of school. Lovely lads, but given my Nature and Nurture, I wasn’t comfortable giving orders let alone holding people I viewed more as peers accountable for results. With the media landscape changing and the entertainment industry being over as we knew it, eventually I chose to remove the complexity I’d introduced in my organization and bet on youth, instead. Of the four, only the CFO remains with us. I’m happy to have tried it once but unsure if I’d do it again.

Entrepreneurship is a thankless job

Leading youth is tricky. After a period of massive expansion, I realized that just because you create jobs for young graduates, it doesn’t mean that all of them will excel at, let alone appreciate, the opportunity. That experience was hurtful, because 

a) I forewent personal passion projects and green-lit projects my team wanted to pursue;

b) I punted on investing in external companies to instead create jobs within WatchMojo.

As that involved inexperienced recent graduates, once the unhappy and unappreciative left the company orbit, our culture and operations improved. In the end, I was relieved and learned to hire slow, fire fast. 

I could (and one day will) write a book about the experience, but therein lies the paradox of compensation: older execs want you to pay them for their past glory, younger staff for their possible future contributions. Good luck with that.

An Inclusive Culture

As a good leader, true diversity and inclusion means a meritocracy of ideas, as well as being able to absorb blame for organizational failures while passing credit to other individuals to develop their confidence. This also avoid a political, needlessly tense culture.

But sometimes, you can overdo it. Young recruits didn’t “fetch me coffee or make copies,” they would be given development and production resources, and many would pursue passion projects, with nary economic pressures to return the investment. We were ultimately taking chances on shows and hoping they’d prove to be financially viable over time. Most weren’t. No one got fired. But when you do that at the expense of projects you are more passionate about, there’s bound to be some regret. Exacerbating the frustration is when you see that those people don’t realize how rare that is in an industry where Scott Rudin-level abuse was the norm, and not the exception. But, I digress: lessons learned.

The Insecurities That Drive Us

In 2018, we were pulled into ICM’s efforts to acquire Just for Laughs (one of the company’s that inspired WatchMojo, as a pioneering media & entertainment export out of Montreal). We were in the mix to become part of the ownership group until I found out via press release that we were out. That stung, but it was business, so I didn’t take it personally. I honestly just felt it was a great opportunity to meet ICM Partners’ founding partner Chris Silbermann, Montreal Canadiens owner Geoff Molson, whom as a hardcore Habs fan I may have skewered over the years but as fellow citizen and entrepreneur always gave much credit for being a great fan himself, businessman and community member (Editor’s note: of course, just as I published this, the organization went out and drafted a convicted sex offender in the entry draft).

The silver lining is that had we prevailed, Covid’s impact would have adversely affected our ability to fund its operations throughout the pandemic. Everything happens for a reason.

In 2019, we considered a transaction with Sony Pictures for Crackle.

When in 2020 we considered buying Funny or Die (but ultimately walked away from it), I wondered how much of my interest was in the businesses themselves, and how much of it was fuelled to drive the point home that we had “made it.” I assure you 80% of deals are made out of vanity and ego (20% would be greed).

Expectations and Priorities

In my 2018 article The biggest lesson I learned in 20 years, I discussed that if you’re not enjoying yourself, you only have yourself to blame. Of course, fighting for the freedom of media and expression wears you down. Then in 2019 after non-stop work travel, Seth Rogen sent me to the ER. I tried to learn from those experiences, and as the decade came to an end and WatchMojo capped off its 15th year of operations, my mindset shifted from expectations to gratitude

No More Savior Complex

I wish I could have done more!

In 2020, Covid accentuated that sentiment and I urged my team to acknowledge our good fortune as front line workers and first respondents bore the brunt of things. By year’s end, I was actually in a good spot mentally, happy to lead my team who was able to work from the safety of their home. The pandemic further cemented my own sense of perspective and privilege, pushing me to help as many people and organizations as possible. I love helping others, it’s what I enjoy most. But over time, your inbox becomes overrun with requests for your time:

“Hi Ash, Respectfully requesting 30min zoom over the weekend, plz provide availability so i can send an invite.”

“Hey Ash, Wondering if you have five minutes tomorrow just the two of us, at your convenience? no rush and all good.”

The former wanted me to invest in their idea “on the spot,” and when I had the audacity to divert through my deal team to give it the proper attention, I was called out for not wanting to make the call. The latter was someone who wanted to revisit terms on a possible deal, killing the partnership before it was able to take its first breath of air.

As someone whose mantra is Here to Serve, I began to realize it was a tad too idealistic and our newfound success made that unrealistic: I couldn’t be so exposed to others, because if I said yes to everyone, I would break down because finding yourself between people with different moral compasses is painful.

The Last Bastion of Unaddressed Bias in Corporate America

“We get it, you have Jewish friends…”

Even though I’m atheist and as Muslim as a BLT sandwich, as an Iranian-born, Muslim Canadian male, post 9/11, you are marginalized (my condensed views on religion is that historically, people turned to religion to i) answer what science had failed to explain and ii) rationalize bad things happening to them. Religious groups were sports clubs, its leaders the gurus we now idolize. In theory, science and education should have washed away all religions, but it’s a racket and most people are dumb).

If you then choose to study finance or pursue a career in media, you’re an outsider. If I became an entrepreneur, it was because I ran out of employers to get rejected by.

As a cisgender, white male, I never viewed myself as a victim, but with hindsight and deep introspection during the #MeToo and BLM movements, I began to come to grips with how much I bottled in years of prejudice and discrimination. Ironically, I spent 2006-16 building my network in NYC’s media industry, in a city that was targeted by Islamic extremists, but won over many friends from all walks of life.

But as I shifted my sights to LA to expand WatchMojo’s entertainment footprint, I found myself in a community (LA) with a massive Iranian population but in an industry (Entertainment) that remained insular. The irony was that unlike some of their brethren in Manhattan, Los Angelinos didn’t bear any ill will towards Muslims (over 9/11), but as an industry, it remained somewhat prickly to outsiders. I always thought this was all somewhat in my head, but when I published Insecurities: The Muslim and the Jews, a Jewish industry friend and entrepreneur told me:

“Been thinking about the post since I read it this morning. I'd actually bet you were discriminated against, but not because you are Muslim, it's just that you aren't Jewish. We are SUCH an insular people. Grew up in a town with only Jews, school, sleepaway camp, it wasn't until college that I met people who weren't (almost) exactly like me.”

You can stand against racism and play your part to educate people on anti-semitism all you want, at the end of the day, you will always walk alone.

No Respect

Nothing proved that more to me than when in late 2020 I found out that a group of people/organizations I’d spent a decade developing relationships with – including but not limited to WondrCo, UTA, Liontree et al. – had backed an entrepreneur’s (Ben Sherwood) startup whose brand encroached on our trademarks. I presume such early-stage investments are below my contacts’ pay grade, but people don’t rationalize these things. Reading Sherwood – who is fourteen years my senior, a product of corporate America as the former President of ABC News at Disney – say that he was driven “to build a brand” after we had spent 15 years building said brand was particularly jarring and hypocritical given the app’s intent to coach kids (i.e. starting off by encroaching on our brand). But, I digress, as this was vintage Hollywood

When it comes to formats, I’m the guy who reminds everyone that “hey, we didn’t invent top 10s – Letterman, Wayne’s World, the OG of lists Moses and his Ten Commandments.” But with trademarks, it’s different. Nonetheless, after voicing our discontent but opting to avoid the heavy-handed legal route (during a pandemic, over the holidays), I decided to take a more statesman approach and suggest a compromise for all parties to save face and bridge the gap. It’s not like you have a monopoly on everything, but as CEO, you’re the chief corporate gladiator and need to protect your company’s assets – its people, the brand, your intellectual property, and so on.

Entrepreneurs are masochists, executives are sadists. Even the best ones rot after years of dealing with the corporate, trickle-down “politricks” of their soulless boards. There’s a lack of intellectual honesty that I’ve put up with all of my career. If you want to know why I had embraced YouTube – which had disintermediated the gatekeepers’ power – look no further. Now, some may ask if it’s tone deaf for me to call foul when I built a business around Fair Use, I’ve touched on all of that here. Rights holders induced and encouraged us to cover their works, only to abuse copyright tools when the financial stakes grew, which became my key source of stress and anxiety, with all of these other experiences piling on.

The Hits Keep Coming

A few years ago, I was introduced to a Montreal-based company Mediabiz International / Starlings Entertainment and their CEO Karine Martin. Initially, she wanted to co-produce kids’ programming she was developing, and promote them across the WatchMojo network. In turn, I told her about a handful of our projects, including my second book, an [auto]biographical book on Alexander the Great, entitled The Confessions of Alexander the Great: 33 Lessons in Greatness, and my desire to produce shows based on it (I have dozens and dozens of Alexander-related projects). We spent six months exploring a partnership.

Yada, yada, yada, in January 2021, I read that through Mediabiz’s new subsidiary Starlings Entertainment (created when we were in discussions in 2017), they were producing a biographical TV series on Alexander the Great, in collaboration with Ben Silverman’s Propagate, written by Vikings and The Tudors’ writer Michael Hirst. 

When it comes to larger productions, the reality is independent creators can’t pull it off alone. Distributors like Amazon, Netflix, CBS or HBO encourage creators who lack a track record in developing or producing scripted programming to partner with someone that’s experienced in the genre. Given my lack of track record in producing scripted programming, those ordering such shows would want us to not only commission writers of Mr. Hirst’s caliber, but also to partner with production companies like Mediabiz or Starlings (producers the Rocketman feature film on Elton John, and TV projects like Sherlock’s Daughter, the Romanovs Series alongside the Alexander the Great series).

When I recently relayed my experiences to industry friends to explain why I was less open to partnerships, most were impressed with how “stoic” I was.

Stoic? For ninety days from late January to May, I woke up every night at 3am, rethinking my steps and kicking myself for being so open. While staying focused on my day job, I tried in vain to convince Mediabiz to include me in a creative and commercial role in the project. First, I pleaded to hearts and minds, then dangled carrots and sticks… but to no avail.

Telling an executive who was inquiring about job openings at WatchMojo that “this one time, I wanted to develop a show on Alexander, and then…” they would think I was crazy. But I wasn’t crazy, people in Hollywood concurred:

  • “Based on what you have shared with me, I don’t see any reason why you wouldn’t at least ask for an executive producer credit.”
  • “At the least, you should be attached to the project and with a fee too. It does happen all the time, but to the little guys.”
  • “What you’re describing here happens every day in Hollywood.”

Through her lawyers, they claimed (amongst other things) that they did nothing wrong. I may one day expand on the ordeal, but for now, the point is that in general, no one really opens up about what ails them. Often times, what ails someone seems silly to those who envy your success. But it’s not about that event, but what that incident means and how as human beings we internalize them. I may be stoic now, but I was anything but and went through the gamut of emotions, especially after being ignored for a whole month. Closure requires finding balance between those emotions. It’s a process and constant struggle to a destination you never reach, you will never truly overcome all of those emotions, but can manage them over time. It’s essentially a journey to an unreachable destination.

All factors being equal, a show about Alexander would be difficult to green light. For one, it would be expensive to produce. Second, separating the influential figure from the “toxic masculinity” tag in today’s climate while addressing the true nature of his relationship with his best friend makes the storyline challenging. Moreover, the lukewarm reaction to Oliver Stone’s feature film starring Colin Farrell and Angelina Jolie would give anyone pause. I, of course, knew how to address all of that – as any self respecting driven individual would.

As my goals are always different, I gave in to my impulses (i.e. impatience) and insecurities (i.e. wanting to be involved with the project) and broke my cardinal rule: chasing people. I was mainly interested in learning from Mr. Hirst given my aspirations to pursue scripted storytelling, but the more I researched him, the less likely that seemed given his disdain for writers’ room and tendency to write alone.

No one cares about your life stories!

I also reached out to Ben Silverman and his partner at Propagate Greg Lipstone.

“Wasn’t he working on a different project that we’d be a perfect partner for?,” I wondered.

Insanity is defined as repeating the same tactic, while expecting a different outcome.

Here? Same outcome (less the lawyer letters).

“The difference between successful people and others is how long they spend time feeling sorry for themselves. When they take a hit, they don’t take long to get back up,” that’s from real estate entrepreneur and Shark Tank co-host Barbara Corcoran.

Over time, you get it: you may view yourself as the ultimate team player who would do anything – legal, fair and ethical – to win. You think others view you as someone that everybody wants on their team but no one wants to face, but you realize only one of those statements is true! So eventually, you do your own thing. 

I wanted to take these crazy situations I find myself in – full of comedy and drama – fictionalize and dramatize them for audiences of scripted drama and comedy… but then eventually realized: “screw it, just continue doing what you have always done: write about it as you have for twenty years, in articles and books.” Privilege is being able to speak truthfully.

It’s all connected: It’s not you, it’s me

Who introduced me to Mediabiz, you ask? Not my agents at ICM, but one of those seasoned executives I’d recruited. So if you’re: 

  1. a senior executive reaching out to tell me how much you can help WatchMojo, surely you can now empathize why I’m not rushing to bring you on (reality is before you explore bringing on a senior executive, the “sky is the limit,” but once you sign to bring them on, “the limit is the sky” to paraphrase Chris Rock);
  2. a movie/TV/digital series creator pitching me/follow up on a project and I seem less open to help anyone and everyone, more focused on pursuing my own projects… maybe you now see why. Even those who seem so confident and assertive sometimes lack the confidence to bet on themselves, seeking the validation of others. But maybe that’s the silver lining: I’ve learned about the concept of “implied contract” and the expectation to conduct in good faith, so you have nothing to worry about the idea you shared with me.

Entitlement, Expectations, Experience

One industry friend who thought I was stoic, Montreal-based investor John Stokes, asked me if the issue was with my expectations. Indeed, I’m always looking to partner with people, then get disappointed by people.

It’s clear that there were two separate sets of rules: 

  • the ones I played with: ethical to a fault, transparent, complimentary, pumping everyone’s tires, and consistently feeding others with passes and set-ups (ironic, since on the pitch, I’m a striker),
  • and the ones others have demonstrated to me: first as a teenager, then during my college years, and then finally professionally. For two decades, I stood there and saw the ray of light as people peed on me and pretended it was raining. That was my super power: staying positive and gaining strength from setbacks. If you want to strengthen your muscles, you need to exercise them. Similarly, adversity builds your resilience. These days, we are wrapping up tomorrow’s leaders in bubble wrap, when we should be exposing them to harsh reality of life.

But indeed, while I never had any sense of entitlement, I did have a set of expectations. With these experiences, I learned better.

Perspective, finally?

This summer, while playing soccer, I got hit with a ball in the eye. It took a couple of visits to the ER to ensure it wasn’t a detached retina, but the temporarily impaired vision was enough for me to realize that the pace and intensity at which I was competing in the arena of life was not sustainable. If I had to do things differently, I would do many things differently… but I wouldn’t trade where I am today for anything, and that has little to do with work (which is a means to an end).

When I met my wife in the early 2000s, I told her I was looking for someone faithful. I’ve since been blessed with a largely loyal team at WatchMojo. I always stated that I wasn’t delusional in thinking I was going to change others, but I also was adamant on not changing my principles, which have gotten me here and helped make WatchMojo a type of utopian Xanadu. My wife is one of my four co-founders at WatchMojo, all of whom remain with the company. The amount of statesmanship and diplomacy required to maintain the peace also comes at a heavy toll over time, having to manage others’ insecurities and neurosis. But in the end, I’m proud that in our internal conversations, people display intellectual honesty.

Sure, it’s bittersweet that throughout my career I have done my part to support female executives, entrepreneurs and employees and in one instance where I met a more experienced one, the outcome was rather disheartening. Those were my expectations, no matter how unrealistic they may have been. You can adopt a hundred orphans, one of them may still kill ya!

You only have yourself to blame if you expect the best out of people…

eBay founder Pierre Omidyar explained his blind faith in the community by suggesting that “people are basically good.” Meanwhile, Amazon founder Jeff Bezos’ management philosophies can be explained by his belief that people are “inherently lazy.” I think humans start off good, but then how they react to bad things explains if they turn evil. But being good and fair requires hard work and tough conversations, and thus many take the “lazy” way forward. For more on Sins v Virtues, read this.

Physical vs Mental wear & tear: Get Rich or Die Tryin’, Part 2.

“When you see that in order to produce, you need to obtain permission from men who produce nothing - When you see that money is flowing to those who deal, not in goods, but in favors - When you see that men get richer by graft and by pull than by work, and your laws don’t protect you against them, but protect them against you - When you see corruption being rewarded and honesty becoming a self-sacrifice - You may know that your society is doomed.”
Ayn Rand

Michael Ovitz, the legendary co-founder of Creative Artists Agency, described Norman Lear as “far more intellectually proficient than the things he was doing. A guy who was smarter than his career.” I’m extremely proud of my career, but as with many creative and entrepreneurial people, I’m far more ambitious than my accomplishments. Part of my insecurities stemmed from wanting to do more, but mainly, showing that I could do more. 

I am a passionate person and it doesn’t take much to get me teary-eyed, but I don’t cry often. One night in early February, I woke up crying. CEOs can’t show emotions: their board will think they’re weak; founders worry about displaying weakness: what if their investors think they can’t handle the heat. Men are 3.5 times more likely to die by suicide. Why?

To me, this is the stuff that has made me stronger. But as the pandemic waned and the spectre of traveling to business travel – conferences, pitch meetings and so on – grew, I wondered, “Do I really need this? Do I even want this?” 

When my head of PR asked me if I wanted to speak at Vidcon (where in 2019 I gave the keynote on the history of YouTube), I paused and wondered if I really wanted to run into the very same people who always peed on my leg while pretending it was raining. Would I still entertain the charade, or call them out on their hypocrisy (which reminds me: I’m looking for a producer and host for a TMZ meets Daily Show project. Interested? Hit me up).

I’ve come to appreciate the healing power of No: doing less to accomplish more, and focusing on what matters. As my daughters get older, I’ve decided to shift my energy to them. Were it not for my family, I’d succumbed to depression and addiction long ago. When I sat in the ER waiting room, eyesight temporarily impaired, I realized the real addiction I needed to worry about was my workaholism and nearly twenty years of putting in 100-hour weeks, pulling me into external facing opportunities which would push me into an abyss of pain every time I would be disappointed by others. 

Why Successful People Take Their Own Lives

Wait a minute, is that…

This isn’t my “Why I’m quitting tobacco“ letter, but in light of the daily email follow ups and inquiries that come in, I need to be truthful and effective in explaining why I’ve changed, as it’s clear to others how I’ve changed.

Success may be relative, fluid and subjective, but when you are successful, people think you have no hardships or problems, and indeed, your problems are relatively of your own doing to some extent. When Taylor Swift gripes about her master recordings being out of her hands, or when Britney Spears cries for help, it’s easy for outsiders to roll their eyes. I think I can understand why people like Anthony Bourdain or Kate Spade take their own lives, partly because they can’t find a way to communicate and no one hears their cry for help. Spade sold her business to a giant and as much as entrepreneurs say they don’t view their brainchild as their baby, that’s not always true.

Meanwhile, Bourdain, “despite his enviable career as a travel documentarian, was haunted by darkness that he couldn’t seem to shake. This coupled with his rigorous schedule likely made him feel exhausted whenever the cameras were off. Bourdain’s toxicology report showed no trace of any narcotics and only a trace of a non-narcotic medication. Experts noted that his suicide appeared to be an ‘impulsive act.'” Bourdain’s depth of torture and torment were no doubt amplified when on the weekend before he took his own life, his girlfriend Asia Argento was caught by paparazzi in the arms of another lover (the Roadrunner documentary “throws her under the bus“). It’s easy to say you have an open relationship, but people are wired through their insecurities and seeing your partner cheat on you isn’t going to help someone struggling with depression and addiction.

“He often brought up death, wondering out loud how he would die and how he would kill himself if he decided to end his own life.” I would never give in to that, partly because of my family, and my superpower ability to see the silver lining. I can cope with the pain and disappointment in many ways, namely writing. For others, it may be body art or music, comedy in Williams’ case and travel and cooking in Bourdain’s. No one knows what ails someone and those who ail feel sheepish speaking out.

No one would mistake me for Buddha, but there’s truth to: “in the end only three things matter: how much you loved, how gently you lived, and how gracefully you let go of things not meant for you.” In that vein, if you find that I’m not the same person as I used to be, that’s probably because I’m not. I’m not going anywhere, but I’m not going to be everywhere, anymore.

It’s not you, it’s me. 

If you find any of these experiences interesting and want me to expand on them, vote HERE