When people look at a complex, multi-year effort like exploring the return of Major League Baseball to Montreal, it’s easy to assume it’s the most daunting challenge one could voluntarily take on.

In reality, it’s simply the latest expression of a pattern I’ve lived through before.

Here are some obstacles that, at the time, felt just as unlikely — if not more so — than anything I’m contemplating today.

1. Being Sued by News Corp / FOX / IGN / AskMen

Three months after publishing our first video — a fashion & style clip geared to a female audience — FOX sent its legal henchmen to intimidate me into submission. Wrong move.

Despite having zero legal training and staring down an insurmountable legal strategy designed to bleed me dry through meritless injunctions, I hit the books, spoke to litigators, and prepared to represent myself and my company in court.

I won. Decisively.

The then-president of the bar association walked into that courtroom expecting to crush a startup founder. Instead, FOX folded. AskMen continued its march to irrelevance while News Corp units like MySpace and IGN ironically began licensing our videos afterwards.

It was a brutal experience – one I never want to repeat – but it hardened me for an even tougher decade to come. It also killed what little VC interest WatchMojo had… which, in hindsight, was the best thing that could’ve happened to us.

2. Running Out of Funds

By December 2007, just two years in, I was out of cash.
All my savings, stocks, mutual funds? Gone.

My options:

  • shut down,
  • lay off my tiny team,
  • or push forward.

I chose debt – credit cards, credit lines – and eventually, in 2011, I mortgaged my home rather than fire anyone.

We broke even in 2012 and slowly crawled out of the $900K hole. By 2013, we had a massive content base and distribution network. When our viewership exploded in 2013-14, revenues cascaded straight down to the bottom line.

It felt impossible until it became inevitable.

3. “YouTube? U crazy!”

I believed as early as 2006 that YouTube would do to cable what cable did to network TV – and what the early Web did to traditional media. But I also knew being too early is fatal.

From 2006 to 2012 we circled the wagons.

By 2013, we were all-in.

By 2014, WatchMojo was the 7th most viewed & subscribed channel in the world, yet the skeptics remained. A hack, rising competition, platform changes – each headwind just pushed us into new terrain.

4. The 2016 Hack & Heightened Competition

Our meteoric subscriber growth (10K → 1M → 10M) drew competitors – which is healthy.
But the hack? That was different.

It hammered our indexing on YouTube. Revenue dropped. Most founders would have panicked.

I treated it as a near-fatal nuisance – one we survived, one that built new resilience.

5. 2017: A Ton of Foreplay, No Action

By 2017, Quebec Inc. and Corporate Canada finally noticed our U.S. momentum. Suddenly Bell Media and La Caisse were interested.

I could have “taken the bag.”

Instead, I pursued fair, win-win deals. I naively thought I could orchestrate some Toronto/Montreal ménage à trois between Bell and La Caisse.

Fear, greed, ego, pride – from all sides – torpedoed it.

Was I foolish to walk away?
Maybe.
But my gut knew the truth: long-term survival beats short-term liquidity.

6. 2018–2019: Headwinds, Headaches, Heartaches

Great years on paper. Terrible years inside my head.

Too many projects. Too many stakeholders. Too little joy.

But in that chaos:

  • MsMojo emerged
  • Our Snap vertical emerged
  • Our second growth wave (2020–21) took shape

Growth hides pain. Pain builds discipline.

7. 2020: A Pandemic

For a decade, people warned me about copyright risk, platform risk, monetization risk. No one warned me about a pandemic.

Ironically, COVID helped WatchMojo.

While Hollywood shut down, people watched more content at home. Our revenues and EBITDA nearly doubled from the pre-pandemic year. Despite that strength, I sold 25% of the business to a NY-based PE firm to strengthen governance and ensure longevity.

Remote work, cloud-first infrastructure – all decisions years earlier – let us thrive.

Luck favours the prepared.

8. Inflation Re-Enters the Chat: RIP ZIRP

For years, founders said “interest rates don’t affect us.”

Wrong.

As inflation surged post-pandemic and central banks killed ZIRP, advertising slowed. In 2022, WatchMojo had its first down year. It rattled me deeply, even though it was completely out of my control.

But in context? We had:

  • no layoffs,
  • solid profits,
  • and outperformed every private and public peer.

Vice collapsed.
BuzzFeed sank.
VOX was forced to sell 20% to Penske.

Media is hard.
Perspective is essential.

Without these scars, I wouldn’t have the confidence to take on what comes next.

9. Convincing Rights Holders re: Fair Use

The law was on our side. The politics were not.

YouTube was a neutral platform caught between creators and rights holders. That dynamic put me in the middle of a Mexican standoff.

It gave me anxiety, frustration, despair, even PTSD – but we stayed the course.
The irony? We helped shape the standards for fair use, media freedom, and modern digital commentary.

In a parallel universe, online cultural conversation doesn’t exist. Only official clips would be allowed.

I’m glad we fought to make the Web more neutral and fair.

10. Closing Thought

None of these challenges were solved with heroics or certainty.

They were solved with:

  • sequencing
  • humility
  • persistence
  • and acceptance that progress often looks unimpressive before it becomes inevitable

Not because success is guaranteed —
but because the work itself demands to be done.

Against that backdrop, exploring the return of baseball to Montreal doesn’t feel reckless.

It feels familiar.

Almost refreshing, actually – knowing MLB has a process, a timeline, and that all we have to do is prepare, work hard, and be patient. If we put our best foot forward, Montreal can reclaim what it lost.

We rarely get a second chance in life.

Let’s not squander this one.