One of the quiet milestones over the past few weeks has been crossing into what I’d call a FrieNDA phase. Not formal NDAs yet, but enough shared context, candor, and mutual respect that conversations are no longer hypothetical. While I personally adopt a form of “Radical Transparency” about my own affairs, I am a vault when others confide in me, with or without NDAs in place.
While this journey officially started Dec 1, watching my Habs take on the Colorado Avalanche – donning the Nordiques jersey – which led me down a rabbit’s hole exploring what a return of MLB to Montreal with the Expos required, less than a month in, by now it’s clear: capital is not the constraint. As a helpful anecdotal parallel, think of the scene in The Big Short or Moneyball where a character has a financial-related eureka moment. Similarly, in light of rising value of sports franchises, there’s a financial formula to solve for a Montreal Expos ownership group to work and meet MLB’s governance requirement. In essence:
The “right” answer is:
A) 2 Public Equity (PE) funds, each investing a maximum of 15% for a total of 30% +
B) 1 (or 2 – but not a consortium) High Net Worth Individuals (HNWI) and/or Family Office +
some combination of
C) myself and/or WatchMojo and/or my family office & investment fund Granicus, and/or
D) a tech platform / broadcaster / media company (though if you follow where the puck is headed, D is more of a nice to have than a need to have, but I digress).
A mere 28 days into this long journey: I can confirm that the status of the PE tranche has shifted from “between the improbable and the impossible” to the much better status of “possible if not outright likely” – and, again, I remain a pretty conservative investor or executive.
At this point, institutional investors I talk to are leaning in to take on as much of the pie as possible, and open my eyes to how the ask on HNWI/Family Offices is even less cumbersome than in my initial model. The TL;DR version is MLB’s governance restrictions are ultimately
– limited to the franchise ownership table (ie. a PE firm can underwrite 100% of the stadium; PE funds are capped to 30% in the team’s cap table,
– meaning what an HNWI or Family Office has to own as anchor investor is a function of solely the sports team, and not the added cost of a stadium).
While this may be obvious to PE funds who are chomping at the bits to deploy the trillions of dollars that are sloshing around in money markets & other low yield accounts, I concede that my initial assumptions were actually more stringent than in reality (again, I am conservative).
Before we touch on the HNWI/Family Office tranche, if we were discussing this “case study” as part of the Academy & Study of Entrepreneurship in the forthcoming 4C campus, a bit of housekeeping for governance, business law & ethics purposes.
WatchMojo and the Expos: Related, Not Entangled
Even before inviting a PE fund to WatchMojo’s cap table in 2020 (more on that below), I was always very conservative with governance, which explains our “clean sheet” over 20 years of financial audits, pay equity audits, job satisfaction surveys, loss provisions, profitability etc.
WatchMojo and any effort related to the Expos are separate, though to the extent it makes sense on a stand alone basis, I have an open mind.
While “sports, media, entertainment” are colliding at a macro level, I want to be mindful of the scope of business that my investors ultimately invested in in 2020.
I hope they share my passion for this journey (and where it may lead), but I think it’s prudent to view these as different mandates, with different risk profiles, would-be partners and while adjacent, in light of the M&A process I started in 2025 due to the growing inbound interest from strategics & institutional investors bullish on YouTube, have different timelines.
Of course, any league would welcome WatchMojo’s global marketing reach, our fan engagement & creator economy technology (FanOS), etc. but to really nail the landing and make sure each and every stakeholder is satisfied requires deconstructing the challenge(s) at hand as structurally and governance-wise, then it is important not to encumber or adversely affect one for the other. If one of the gating elements is to win over the trust of new PE firms, not forgetting the rights of your existing PE is a good principle to retain!
The WatchMojo process itself – narrowing down a “prevailing party,” but not letting anything to chance with regards to my planned roll-out of scripted projects on our slate of scripted projects (no different than how telecoms evaluate multi-year CAPEX) – is what inevitably led to broader conversations around “bigger” targets, and ergo, sports franchises, which may or may not include the Expos. Too many rush the process instead of doing diligence properly and minimizing surprises in the steps to close. In theory, the prevailing party may and can be a party to any eventual Expos ownership group, ultimately (there is so much Interest from the institutional investor tranche as well as Intent, though we will find out if that translates to Action in M&A parlance) but the priority is to finalize the WatchMojo transaction with them, instead of complicating and/or slowing things down in what is ultimately another, separate, longer-term process (the MLB expansion bid) whose outcome I do not control.
I’d also like to emphasize that nothing in this article is “addressed” to a) my existing shareholders, b) the investors I am speaking to wrt the Peanut Project or c) the “prevailing party” in WatchMojo’s process – this is really to give the Expos fan base & community an update as I start to limit the flow of information (not just “confidential” but in general as the inches take more time to gain).
Learning While Moving Forward: Divine Guidance?
Life has a funny way of unfolding.
I have always seen myself as an investor, but I’ve tended to downplay that identity in favour of my role as a founder and operator. In September, however, when my investor was in town, he asked me a question any self-respecting fund manager would ask when courting new investors or LPs: where would I look to invest in the future – especially if this second transaction goes through?
That question hit me. If the investors who backed me as an entrepreneur and operator already view me as an investor, then I should start seeing – and positioning – myself that way too.
Each month, I receive dozens of investment opportunities, all of which I’ve declined. Since 2023, I’ve focused almost entirely on WatchMojo. Before that, in 2021 and 2022, I “paid it forward” by helping as many entrepreneurs as I could following our 2020 recapitalization with a PE investor. By that point – eight years after we had broken even and no longer needed outside capital – bringing on a PE fund wasn’t about survival. It was about improving governance and, in hindsight, served as an education in how PE funds think and operate as financial partners.
In an almost biblical twist, Netflix released its Expos documentary in October. We discussed it on our Inside podcast, and when on December 1st I watched with a sense of indignation the Avalanche’s desecration of the Nordiques jersey, despite not being a religious person, if I were looking for signs, they’d be flashing red (and blue and white)!
Finally, while it was too early to establish a family office after the 2020 transaction, if this follow-on transaction does happen, I would seriously consider setting one up formally. In that case, learning from other family offices – an ecosystem that operates very differently from institutional PE – feels like the stars are aligning. After 47 years on this planet, I finally believe in fate and destiny, without the same need to overthink things.
The World of Family Offices & HNWIs
It’s easy to build models, it’s another thing to take them from concept to reality.
For someone who doesn’t “need a gig,” I’m approaching this with an intensity and hunger that is fuelled not solely because of my personal entrepreneurship origins story (became one when feeling helpless top save the Expos in 2004), but also because it would be hypocritical to stand by idly when the skill set to submit a proposal to MLB is in my wheelhouse and the civic scope is transformative, the utility is universal, and the upside is far beyond financial (to be clear, in the near and mid term, doing this makes no financial sense for me, but I am at most long-term greedy & beyond contrarian). The amplifier effect is massive: few projects touch sports, culture, community, and civic identity all at once.
There is something emancipating about leaning all the way in on a project that is, quite genuinely, for the greater good. Sports has the power to unite, to quote Nelson Mandela, but civic duty trumps all.
Paradox
While this exercise is in my wheelhouse, it is by no means easy or simple. But there is an irony here that is paradoxical:
From 2005 to 2012, my fundraising efforts with VCs largely failed (no one invested in content then);
From 2013 to 2016, as revenues took off and we experienced high degrees of operating leverage, I ignored fundraising entirely;
From 2017 to 2018, the focus was more M&A than capital raising, but I was naive in trying to align parties who had very different objectives;
In 2019 and 2020, our WM2020 reinvestment efforts were widely misunderstood so talks proved frustrating and fruitless;
Then following Covid, home entertainment – combined with the WM2020 bets paying off – culminated with our December 31, 2020 “recapitalization” transaction where we sold a 25% minority stake to our PE fund investor. It all now makes sense.
Here, the situation is inverted: this is
- a rare asset with favourable supply-demand dynamics,
- in an asset class that has historically yielded ~13% annualized returns (CAGRs) over sixty years,
- comes with a history, legacy & brand that stands out vis-a-vis the field, etc.
Those Who Don’t Learn From History Are Doomed
If one were trying to play hero, it would be easy to secure financing sooner but under a house of cards kind of foundation – and I do think MLB saw this with Montreal’s previous attempts to bring back the club.
When Claude Brochu acquired the Expos, he did not have the deepest of pockets, but he did have the Bronfmans’ loyalty & trust, having served as their VP at Seagram for years. Due to his limited resources, he then enlisted a dozen of Limited Partners (LPs, or minority investors) – none of whom viewed the asset strategically and viewed it more as a charitable cause. As a result, when patience wore out, art dealer Jeffrey Loria bought the club, but in those negotiations secured capital calls that – if unmet by other investors – would give him greater ownership. This is all basic finance, but ignoring history could lead to a very tragic outcome whereas my objective is to future proof outcomes to ensure if MLB rewards us with a franchise, we never lose Nos Amours, ever again. WatchMojo surviving – let alone eventually thriving – was an obstacle far more challenging and complex than this by orders of magnitude. Here, while I do not control the outcome, I can take the time and care to prepare and plan properly.
If you respect each investor’s risk profile and cater a structure that works for all, you can secure the right framework and balance of rights, vetoes over the proper time horizon and ensure that the Expos 2.0 will be “built to last.”
The End of the Beginning
In some ways, this is just the end of the beginning, as I shift the focus on Family Offices and HNWI Principals (FWIW, I don’t view HNWI and Family Offices as a monolith, but understand why it’s classed as one). I’ll outline that process and method to the madness soon.
Whereas VCs and PEs earn their compensation above and beyond their salary by placing the investment they raised (their management fees) and then earning success fees (carry) when businesses are sold at a profit, family offices & HNWI don’t have to do anything per se, don’t need liquidity in the same timeline and manner as PE funds. Some may not love to own a sports team (but may be compelled by the asset’s return and safety) while others would love to own one if they could rationalize the geography. Being a masochist based in Montreal with a penchant for diplomacy is part of what draws me to this challenge. Ideally, the HNWI or Family Office is Montreal-based, but that is not required if I as minority investor serve as the point-man with MLB, managing PEs objectives with the Family Offices’ priorities, and so on. I am also mainly interested in helping athletes – who previously envisioned a career in broadcasting or coaching post-career – but now aspire to be entrepreneurs and investors – all my areas of expertise.
When fundraising for WatchMojo from 2005-2012, the pressure of running out of funds and ending up homeless, unemployed and forever indebted while living in a back alley was a real probability. Here, there is zero pressure and since few expect a positive outcome, manufacturing an opportunity to create something where no one thought anything existed is par for my course. Join me, or get out of my way, as I like to say.
Learning Is Also Winning
As stated, to keep my sanity and manage my expectations/possible disappointment, I’m treating the Peanut Project as the first formal case study and mandate for three parallel efforts:
- The Academy & Study of Entrepreneurship I’m setting up (ideally at 4C),
- Granicus Group whose Granicus Advisors unit will incorporate the best lessons and practices I have learned from the fields of investment banking, law, accounting, consulting in a post-AI world,
- Getting to know family offices, how they work, and determining if I want to roll my assets into an existing one, or build a single family one to reflect my risk profile and time horizon.
Either we prevail and secure a franchise, or I learn a ton, document the process for future generations and build institutional knowledge that compounds.
All I can promise you is that through this effort, we will propose the strongest, most credible bid possible for MLB to evaluate and make it not only the best proposal Montreal has ever submitted, but also miles ahead of anything other cities will present.
The outcome is not mine/ours to control, but the preparation and respect for the process is.
And that, ultimately, is half the battle.
Next up: an update on the consiglieris who are showing up, eager to help and serve as sounding boards…