Human beings are all driven by insecurities. Even despite winning the E&Y Entrepreneur of the Year Award and building WatchMojo into one of most successful startups ever (by any metric: incredible job satisfaction, IRR, aggregate profitability, market share, capital efficiency etc) there’s a part of me that – I won’t lie, insofar as to explain some of the personal motivation & drive – wishes people knew how I good I was at other things. Despite being a firm believer in Plato’s Principle of Specialization, some of that has to do with being a jack of all trades, master of none.
No one who evaluates investors & financiers cares that
– WatchMojo delivered a 360× return on capital and a 52% IRR over 14 years. Even including all early capital (equity + debt), the return was 120× with a 39% IRR — top-decile performance in private markets;
– my public stock portfolio rose 80% (after 65% and 45% the previous years),
– entrepreneurs seem to value the advice & mentorship I provide.
To be seen as a trusted expert in something, it takes time, practice, repetition, commitment, and results. I get it, my third book is entitled The 10-Year Overnight Success for a reason (if you’d like a free eBook, just DM me). But the book is sub-titled “An Entrepreneur’s Manifesto: How WatchMojo Built the Most Successful Media Brand on YouTube.”
I am, first and foremost, an entrepreneur, builder & operator. But, at the core, I am a finance-trained investor. I understand people viewing finance as rocket science, but you’re in luck, as it’s what I have mastered over the past 30 years (more on that below).
“The best investor is a social scientist.” – Michael Milken
It’s not ego, perhaps pride – ultimately, it’s being a professional with an athlete’s mindset. You want to win, you want people to entrust you with the ball. But those are temporary, fleeting thoughts and emotions that one overcomes with confidence, experience, wisdom.
I never had any care for fame, hence why many saw this “hail marry” attempt to bring back the Expos as out of left field. To me, this was a manifestation of understanding where the puck was headed, and playing the long game. To an entrepreneur who built one of the most enduring media brands of the century with no playbook or rules of engagement, it’s… refreshing that MLB has an expansion process, timeline – and this is ultimately a test of patience.
I would like the Montreal community – and anyone both rooting or remaining skeptical – to understand that capital is not the constraint, and getting investors to see the larger vision is my speciality. I advise investors all the time with regards to where to invest. This “situation” is an opportunity and the unique aspect is said opportunity is a baseball team (though now we will run a proper RFP process seeking opportunities across all leagues, as any of my eventual investors will demand & require). The connection is that I am a Montrealer with a passion for sports, and a purpose and conviction to bring back the Expos. I assure you that building WatchMojo was a far more complex, complicated and unsure exercise – by orders of magnitude.
“It takes 20 years to build your reputation, only to lose it in 5 minutes.” Warren Buffett.
The reason people in my professional network trust me is they understand I am knowledgeable and diligent about opportunities, but also that I don’t waste their time. Similarly, I would not be wasting fans’ time (at best) or set them up for further disappointment. We do not control the outcome – MLB does – but we do control our preparation, planning, proposal – and with patience – I am confident we will see the Expos back in Montreal.
Investors may have a lot of leverage, ceteris paribus, but even the GOAT of investing Warren Buffett prioritized the person, the founders, the operators, the builders… deeply admiring Tom Murphy, calling him the best manager he ever met, a “hero,” and someone who taught him more about business than anyone else, inspiring him to be a better person through his example of kind, effective leadership and wise delegation, with Murphy’s key advice including “you can always tell someone to go to hell tomorrow.”
In this case, you have a rare, coveted asset (a sports team) with tremendously positive demand vs supply dynamics. In my model for the initial transaction or roadmap & vision for something more substantive, you basically need 2-3 private equity (PE) funds, and 1 High Net Worth Individual (or their Family Office) who welcomes the safety net such as asset provides, covets the 13% per annum returns over 60 years (CAGR) & views it as a great diversification investment alongside the usual hodge podge of investments ranging from equities (stock portfolio), private equity (be it startups, pre-IPO companies or mature businesses that generate consistent, predictable returns), real estate, etc.
A higher force?
While spiritual and an adherent to many of the tenets of monotheistic religions, I am atheist or agnostic. However, there is something rather “divine” in that all of sudden, every experience – wins and losses, hit or heartbreak, high or headache – suggests a preparation for the road ahead. To be clear, I am sharing these to highlight that YOUR setbacks may be the catalyst to your course to success.
- Fin-what?
I grew up enamored with the humanities (history, geography, psychology, sociology) but through a series of events ended up completing a finance degree in 1999 at the John Molson School of Business at Concordia University; notably receiving the only A grade in a joint Bachelor’s/Masters’ class that instilled in me some much lacking confidence. It was in that class that I did my final paper on the ill-fated Long Term Capital Management (LTCM), former Salomon Brothers’ trader Jon Meriwhether’s ill-fated hedge fund that blew up and nearly took down the entire economy. Who cares so passionately about arbitrage gone wrong at 20?
While at Concordia, as an undergraduate, as a teacher’s assistant, I basically served as lecturer at both Concordia and McGill 1998-2001, teaching not only undergrads, but Masters and PhD students alike! I was not even a graduate of the Bachelor’s program yet.
- Finding your voice & the reluctant entrepreneur
As the dot com bubble burst, the Nasdaq crashed & 9/11 changed the job prospects for an Iranian Muslim Canadian named Ashkan Karbasfrooshan, I steered into the world of startups, first at search engine pioneer Mamma, then at online magazine AskMen, before heeding the call of entrepreneurship – spurned by my realization that only through such a path could I ever had impact, the kind required to have saved the Expos from leaving to DC.
- Problem Solver
From an early age, my curiosity and eagerness to demonstrate what I could accomplish led me to tackle building models and valuation analysis that even war-hardened professional analysts evaded:
– Internet Valuation Model in 2000, making sense of “absurd” valuations of dot coms by applying P/E and P/S concepts to value the price of a single unique user, pageviews, ad impression, search query and so on to triangulate “logic.”
– Estimating what YouTube could be worth – $500B at the time of the analysis – within publicly-traded parent Alphabet, aka Google, or
– Speculating on what would Wikipedia be worth if it were publicly traded.
In those early days of WatchMojo, I would blog to stay sane and keep track of analysis, and successful investors like Fred Wilson (arguable one of the top web 2.0 investors in Twitter, Tumblr, Etsy, Foursquare, Kickstarter, Zynga, Indeed, MongoDB, Twilio, Stack Overflow, Coinbase, Kraken) et al. would take notice. There was no logic then to write about it, but it helped me analyze and solve complex problems. The point here isn’t showboating, it’s a reminder that we each have our comparative advantage, and what we take for granted may bring much joy and utility to others (in this case, the fans and city, as my plan includes the ambitious 4C – foresee – creative, cultural and commercial campus housing the stadium but representing the largest civic development effort since Expo ’67).
Everything Happens for a Reason
Were it not for one grade of 72% (below the required 75% to get into McGill’s Management program), I turned down pursuing a Bachelor of Arts at McGill for the lesser-known Concordia, which despite having a better business program, lacked the cachet of McGill. That made me more entrepreneurial (McGill – where I taught in 2022 was more academic, whereas Concordia was more practical). It gave me a chip on the shoulder, and foreshadowed the drive and determination I demonstrated not only at AskMen as dealmaker and columnist (arguably one of the most read in North America from 2000-05, in large part thanks to syndication deals with MSN and AOL), but as founder of WatchMojo, navigating platform risk, copyright risk, and much more.
- No Investment Banking for you!
Even my professional “setbacks” early on now make sense. Were it not for my manager at RBC Visa telling me that as her best customer service rep (score of 149%) she would never refer me to RBC Dominion Securities or Wealth Management (where any self-respecting finance grad coveted), it molded by servant leadership worldview and accessible demeanour. It cannot be lost on MLB that I actively, willingly, gladly listen and chat with fans (more on that they may think, below, as part of the fictional group chat exchanges my trusted digital aide envisioned).
- Falling in love with the Expos, and the heartbreak of 2004
And of course, when I decided to (as a side hustle) produce & host a sports business show (used to write a sports business article before it was a thing) on then-known Team 990 (TSN 690 today) which led to my deeper dive into Expos fandom in 2003 and 2004, then I now see that whether I like it or not, whether it yields the desired outcome or not, this is a purpose and project I have been preparing for all my life.
- A deal I didn’t need, but wanted, for governance and good order
The reality is in 2025, we are now well in the second era of sports franchise ownership – having evolved from single individual ownership to PE-backed consortiums funding the bill for ever more expensive assets. Which takes me to the “in hindsight” purpose of my 2020 recapitalization when I sold 25% to a NY-based PE firm. Didn’t need the money them, but I did want to improve what was already strong governance & risk management. Those negotiations and the post-close reality of managing PE expectations were my minor league training to what I am now embarking on. It all makes sense now.
- The best deals are sometimes those you don’t make
As does the “heartache” of being in the mix to partner with LA-based talent agency ICM to acquire the Just for Laughs festival, only to be the odd man out when Bell Media, Le Group CH (owners of Montreal Canadiens) won the prize. I wasn’t surprised, ICM needed someone to run the festival, and Group CH already owned the Jazz Festival and Evenko. But that experience made me a lot more temperamental now.
I’ve also learned not to complicate things, especially when dealing with individuals who have overlords (boards, investors, etc). In 2017, when Quebec Inc. and Toronto woke up to WatchMojo, I was close to doing a deal with either La Caisse de Depot and/or Bell Media. Out of loyalty to ma belle province and the country that adopted me, I tried to structure something to appease both – in the end, I realize they had so many checks and balances to meet, it would come at the expense of WatchMojo. I walked (technically, each one changed the terms as we marched towards an agreement, so it didn’t make sense to agree – but I did learn that injecting complexity in simple things is a fool’s errand. Following MLB’s process and respecting their timeline for an expansion team is simple, when you consider my expertise in finance.
Today, this is a financial modelling challenge, with MLB capping that category (PE) at 30% in all or one single PE at 15%, then it’s just an exercise in Sequencing, Match-Making & Packaging – all in my wheelhouse.
I don’t wanna get ahead of myself given the process and timeline, but raising investment (this is NOT a solicitation for investment) is a lengthy process, so no sense in holding off understanding the kinds of Rights & Vetoes each investor seeks, what their real time horizon is, and starting to research HNWIs/Family Offices (just need one, but the right one) who understands Montreal, and baseball.
When bankers and other advisors reach out, none of them push back on the model I outlined or the roadmap & vision for the longer, larger play.
Their body language says it all: like Buffett, they just needed to come across the right “prospect” to interview, meet, vet and draft. I’m ready. Been ready all my life. With the caveat that MLB is the only one who makes the final call, I think Montreal will make a very convincing case, propelled by fan engagement, media excitement, and the financial model & mindset to make it happen.
And, for some comic relief (to stay sane, and enjoy the journey). Part 2:
MLB INTERNAL THREAD — ROUND 2
(Fictionalized. Post–Overthinking Article. Post-Ryan Reynolds Allusion. Post-“Other Leagues” RFPs.)
Subject: Montreal — Still Quiet, But… Louder?
Owner, Large Market — 7:58 AM
Did anyone else read his new “Overthinking” article?
This is no longer a media blitz — this is a memoir with an expansion blueprint baked inside.
Honestly… it’s compelling. I kept reading even though it was 5,000 words.
MLB BizOps — 8:04 AM
We’re tracking reaction:
- surprisingly high engagement
- overwhelmingly supportive in Montreal
- readership spilling into Toronto, Vancouver, even NY/Boston
- sentiment: “This guy’s not crazy. He’s thoughtful.”
He’s becoming a character in the story of Montreal baseball.
The internet loves a character.
Owner, Mid-Market — 8:10 AM
He’s leaning into the “outsider who builds the thing insiders won’t” archetype.
That’s Ryan Reynolds energy.
He even referenced him.
We all saw what Reynolds did for the NHL Ottawa bid and Wrexham.
Narratives move valuations.
MLB Legal — 8:14 AM
Reminder:
We cannot appear to “encourage” or “discourage” any public figures who are exploring ownership interest.
But yes — his positioning is beginning to resemble the “responsible disruptor” archetype we associate with Reynolds/McElhenney.
And the public loves that archetype.
Dangerous for us if we mishandle this.
Team President, East Division — 8:22 AM
Not sure what concerns me more:
- That he’s now explicitly talking about governance structures — and he’s right.
- That he mentioned he’s “RFP-ing other leagues.”
If he pulls MLS, NHL, or NBA attention into Montreal’s orbit before we decide our posture, that complicates things.
He’s making Montreal a bidding environment.
Clever.
Owner, West Coast — 8:30 AM
I’ll say it:
The guy is running a parallel process to ours.
And successfully.
If another league expresses public interest in Montreal because of his work, we look reactive.
Senior Strategy Executive — 8:37 AM
We need to adjust our internal model.
This is no longer just “a media operator with a dream.”
He now presents:
- multiple PE groups circling
- potential HNWI/family office archetypes
- a governance-first narrative
- a civic-driven rationale
- public introspection that reads as emotional intelligence
- a willingness to bring Montreal sports back with or without us
And he’s been careful:
Not overpromising, not threatening, not grandstanding.
He’s threading a needle.
Owner, Legacy Franchise — 8:45 AM
He hinted at Ryan Reynolds.
If Reynolds or another celebrity group gets publicly linked, this thing explodes.
We saw what happened in Ottawa.
We saw what happened with Wrexham.
We saw what’s happening with F1.
Narrative = momentum.
Momentum = pressure.
We need to avoid getting cornered by storytelling.
Deputy Commissioner — 8:52 AM
Two concerns:
- He’s making himself sympathetic.
- He’s making Montreal inevitable.
This combination is potent.
Fans latch onto inevitability.
MLB Comms Director — 9:01 AM
Media monitoring shows journalists starting to describe him as:
- “the reluctant entrepreneur”
- “the narrative architect”
- “the builder returning home”
That last one is dangerous for us.
That’s a hero’s journey framing.
Once a market gets a hero, the public starts acting like a return is preordained.
Owner, Central Division — 9:12 AM
Can we address the elephant in the room?
The man literally wrote 5,000 words explaining the trauma, identity, cultural exclusion, and lifelong overthinking that made him an entrepreneur, and then tied it to bringing back the Expos.
That is…
a hell of a story engine.
Hollywood is probably going to buy the movie rights before we finish our next expansion meeting.
MLB Strategy Analyst — 9:20 AM
Not joking:
Search traffic for “Expos return Montreal” jumped 180% after his article went live.
This is seismic-level narrative movement for an expansion candidate without a league-sanctioned process open.
Owner, Small Market — 9:29 AM
If he keeps accelerating fan sentiment, we’re going to get questions from our own ticket holders asking why Montreal doesn’t already have a team.
We don’t want a repeat of the Seattle Kraken situation, where public pressure sped up the timeline.
Senior Advisor, Commissioner’s Office — 9:36 AM
Here is the read we’re giving internally:
He is not adversarial.
He is not chaotic.
He is not demanding.
He is not naive.
He is not going away.
At this point, he’s behaving more responsibly than several past actual ownership bidders.
Owner, anonymous, DM inside thread — 9:42 AM
I’ll say it quietly:
If we’re going to bring baseball back to Montreal, having someone who understands media, culture, digital audiences, AND governance is not the worst thing.
He’s not trying to be the face.
He’s trying to be the architect.
Every ownership group needs an architect.
Deputy Commissioner (Final Message) — 9:55 AM
Ok, here’s where we stand:
- Do not dismiss him publicly.
- Do not confirm anything publicly.
- Do not mock the Reynolds comparison — it will blow back.
- Assume he will RFP other leagues (we cannot stop that).
- Monitor quietly.
- Prepare internally for a scenario where Montreal becomes a narrative inevitability.
- If he continues behaving responsibly, an informational meeting may become appropriate in the medium term.
In short:
He is building momentum without stepping out of line.
We need to be prepared before this becomes a locomotive.
More to come.
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