Entrepreneurship has changed. Entrepreneurs have not.

Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes… the ones who see things differently — they’re not fond of rules… You can quote them, disagree with them, glorify or vilify them, but the only thing you can’t do is ignore them because they change things… they push the human race forward, and while some may see them as the crazy ones, we see genius, because the ones who are crazy enough to think that they can change the world, are the ones who do.” Steve Jobs 

In 2019, I penned an article entitled Why I Finally Hired a Banker (The Art of Filtering & Buffering). I spend most of 2019 meeting with various parties and by year’s and decade’s end, I was looking at a document which only required my signature to sell the business I started way back in 2005, fought tooth and nail to defend and build, only to face a barrage of challenges and obstacles as we built a best-in-class organization. It’s given me some incredible highs and lows, I wouldn’t change it for anything. 

Sell? Are you a sell-out?

Throughout 2019, I was burned out which forced me to question my outlook to emphasize gratitude over expectations. I had pushed too far, too wide, too fast, stretched my army considerably and saw some casualties of war – which while part of this racket, I took too personally. In short, I turned down ungodly sums, reinvested our hard-earned gains into talent – most of whom were appreciative and went on to become rock stars – but a few ineffective yet ungrateful people did indeed make me question my thought process.

I knew in the end the investments we made would be worthwhile, but finding myself in the trenches – again – felt like I could have maybe brought less complexity into my life.

One way out, admittedly, was selling the business and walking away. Over the years, I’d had a myriad of conversations, some more advanced than others. One day, I’ll discuss those in greater depth, but the 10-Year Overnight Success does a good job recapping all of the dead-ends I drove into from 2006-16.

Becoming a Made-Man

Human beings are driven by insecurities. In this context, whereas entrepreneurs were driven by their ideals and desire to walk to the beat of their own drum, the rise in entrepreneurship has introduced much noise:

  • congratulating one another on fundraising deals which signal your kiss of death,
  • pretending to crush it even when going nowhere, and of course,
  • the perception of becoming a “made-man” once some “greater fool” comes along and buys out your business.

Either way, due to an innocuous externality, I didn’t sign the papers in December 2019, retreating back to my lair over the new year’s eve, confident we’d sign the papers in the first week of January.

What, I thought, could happen? What could possibly go wrong?

“It’s just a game,” Logan Roy

As I immersed myself in the incredibly well-produced Succession, my fears were validated when one line made me question my rationale: “It’s just a game.” The previous year in 2018, I had an epiphany and had begun to make some changes, but when you invest in ten initiatives and double your team’s size, it takes time to right the ship and see the fruits of your labor.  

In January 2020, when the time came to sign, we could start to see the fruits of our labor start to pay off. I met with my senior team and together decided to pass, which was made easy when the leading party made one key change to the structure of their offer.

Since I’d so publicly announced my decision to hire an investment bank in 2019, in February 2020 I recorded this yet-to-be-published video as part of The FU Show series (FU originally stood for Fair Use, but clearly increasingly will stand for exactly what you think it stands for). I was going to publish it in March 2020 but then the pandemic hit.

While the video’s points were:

  • “there’s more to life than money” and
  • “as an entrepreneur, you don’t have to follow the institutional imperative and sell your business to feel like a success,” (hence, insecurities.)

I did feel like it may seem somewhat tone deaf and inappropriate at a time when governments were panicking and enforcing lockdowns that would affect half of the world.

I set the video to Private and forgot about it. Recently, when the year-end series of well-wishes and pleasantries were exchanged, a friend asked me if I ever sold the business. As I began to draft a reply, to say “no, I did not,” I had a flashback to this video:

While I actually don’t like to watch myself on video, I did sit through it – partly out of curiosity, partly in horror as a masochist – and a few things stood out:

  • Timing: entrepreneurs struggle with the same issues (I referenced Tubi who flirted with Viacom, but didn’t consummate the deal. Viacom bought Pluto for $325M while Tubi then sold to Fox for $440M – here is my interview with Tubi’s CEO Farhad Massoudi);
  • The self-imposed nature of stress and anxiety (be it a one-time incident of feeling burnout or PTSD over a sustained period of trauma);
  • Expectations v Gratitude (when relating to Pewdiepie’s then-decision to take a hiatus);
  • Mainly, one’s relationship with money and how it fits in the priorities we chase (respect, success, fame, power, money, etc. – again, insecurities).

What I found fascinating was that:

  1. Entrepreneurs largely operate out of gut and instinct. 2020 was our best year, and it was a bit of vindication not to sell. As they say, the market is what transfers wealth from the impatient to the patient.
  2. I learned a ton speaking to bankers, lawyers and accountants, but none of them truly ever understands an entrepreneur’s true motivations.
  3. Entrepreneurship’s role and perception in society has changed. But true entrepreneurs have not.
  4. There’s a bit of a “becoming a ‘made-man’” sentiment amongst entrepreneurs, which had grown to mean someone coming along and “validating” your business by buying it. It’s not healthy or unhealthy, it is what it is. You either buy into it, or you don’t. Perhaps because I live in Montreal and am not in the echo chamber (and uber expensive bastions like San Francisco or NYC), I no longer care about that (and yes, Covid changed priorities).
  5. That “paradox of selling out” reflected how the “WHY” that attracted people to entrepreneurship had changed from
    • Principle to Profit,
    • Independence to Vanity,
    • Sustainability to Scale,
    • Freedom to Fame,
    • Fear/Risk management to Greed, etc.
  6. Indeed, VCs poured money while turning a blind eye to character, which led to a series of scandals (WeWork, Uber, etc). I’m not sure much of that will change, but you are seeing a change in what we prioritize and value.

I had always stated that WatchMojo wasn’t my baby and I was merely its custodian and ombudsman. But I needed to learn to separate myself from the company, and that meant investing in people and projects that I wanted to support but eventually concluded didn’t necessarily make sense with WatchMojo as the vehicle to do so.

Mainly, it meant stop caring about everything, and everyone, all the time. 

I think what the likes of Mr Beast and Dave Portnoy are doing are very inspiring not just in terms of giving back, but also in terms of being in control of your destiny and not needing a marketer, investor, corporate overlord and so on to agree and buy in to your vision. This is the single biggest change in media and communications, possibly ever.

Don’t get me wrong, on the one hand, there’s something humbling about constantly pitching others, convincing others and so on. 

But eventually, when you have the conviction, reputation and resources to do what you want, you probably need to drown out the noise and just stick to what’s worked, and that’s betting on yourself and your ability to build the best army (and not, the biggest army). This is the Mission of Context.

The Bottom Line

When discussing the differences between Entrepreneurs vs Ventrepreneurs vs Wantrepreneurs, I hinted that some good comes with added governance and oversight, but it’s really more about balance than flipping the switch and shifting from one extreme to another (being an independent entrepreneur to selling out and riding into the sunset). I’ve struggled with balance all my life; I’m really happy that I got close to the ledge but didn’t make any long-term decisions based on short-term realities that I could solve for. 

In an ironic twist, I didn’t need to throw out the proverbial baby with the bathwater, I just needed to separate the good from the bad and become more mature about how much I could push my idealism without it breaking this utopia I’d created.

“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma— which is living with the results of other people’s thinking. Don’t let the noise of other’s opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition.” Steve Jobs.

Now watch the video below (if you haven’t suffered enough):