Today, Ted Leonsis was unanimously elected Chairman of the NHL’s Board of Governors, succeeding Jeremy Jacobs after 19 years. NHL Commissioner Gary Bettman specifically cited Ted’s “entrepreneurial instincts and forward-thinking approach” and the influence he has had on the league for more than two decades.
Before embarking on the Peanut Project, I was fortunate to meet two NHL owners: Geoff Molson, and Ted.
Ted Leonsis: From Media Executive to Sports Mogul
Long before Monumental Sports & Entertainment, Ted was one of the executives helping build AOL during the commercialization of the Internet.
The Internet was changing how people communicated, consumed information and eventually watched entertainment. Ted had founded Redgate Communications, sold it to AOL in 1994 and went on to become one of AOL’s senior executives during its extraordinary growth.
He had invested in SnagFilms, an online film and documentary company run by CEO Rick Allen.
Given what I was building with WatchMojo, it was not out of the ordinary for us to meet to compare notes.
From the Internet to Sports
Ted was a sports fan long before he was a sports owner. In 1999, while still an AOL executive, he bought the Washington Capitals.
He didn’t merely accumulate sports franchises.
He built an ecosystem.
Today, Monumental Sports & Entertainment encompasses teams, venues, media, technology and entertainment. It owns its own regional media platform, Monumental Sports Network, and is undertaking a massive transformation of the area around Capital One Arena into a larger entertainment district.
That has become an obvious source of inspiration for me as the Peanut Project has evolved.
The roadmap he provided me was easy to map out. After all:
| Ted Leonsis | My Journey | |
|---|---|---|
| Immigrant roots | Son of Greek immigrant parents; first generation American. | Born in Iran, lived briefly in Spain, immigrated to Canada as a child. |
| Internet-native entrepreneur | Built businesses in the early Internet era and became a senior AOL executive. | Built WatchMojo around the migration from television to Internet video. |
| Media → Sports | AOL/media → Capitals → broader sports ownership. | WatchMojo/media → The Lineup → Peanut Project. |
| Sports fan first | Has described himself as a Capitals fan long before becoming an owner. | Lifelong sports fan whose connection to the Expos predates any business interest in baseball. |
| Sports as more than a team | MSE combines teams, venues, media, technology and entertainment. | Peanut has evolved from Expos → stadium → 4C → broader sports/media/entertainment ecosystem. |
| Own the distribution | Monumental owns its regional sports network. | I come from owned digital distribution and audience-building through WatchMojo. |
| Venue as a platform | Capital One Arena is being expanded as the anchor of a much larger entertainment district. | The stadium isn’t intended merely for 81 baseball games; 4C is about what happens around it the other 284 days. |
| Entrepreneur + institutional capital | MSE has grown into a sophisticated sports holding company while Leonsis remains its controlling owner. | Peanut Project is exploring an ownership architecture combining entrepreneurial leadership with HNWIs, family offices, PE, infrastructure and strategic capital. |
| City-building | Leonsis increasingly talks about sports infrastructure in terms of regional economic development and community. | Peanut Project has increasingly become as much about building something for Montreal as restoring the Expos. |
| Content + culture + sports | Media executive, sports owner, investor and filmmaker. | Media entrepreneur, content producer/investor, now exploring sports ownership and infrastructure. |
| Entrepreneur → capital allocator | AOL/operator → sports owner → venture investor through Revolution Growth. | WatchMojo/operator → investor/WM Studios → prospective sports ownership. |
We Are Coming at the Same Intersection From Opposite Directions
This may be the parallel I find most interesting.
Ted essentially went:
Internet → Media → Sports → Venues → Entertainment District
I am coming from:
Internet → Media → Entertainment → Sports → Stadium → 4C
Different routes.
But increasingly toward the same intersection.
And that intersection is based on a fairly simple idea:
A professional sports franchise doesn’t have to be merely a team.
It can be the scarce intellectual property at the centre of a much larger platform.
The team creates fandom.
The venue creates physical congregation.
Media creates distribution.
Technology connects everything.
Restaurants, retail and entertainment extend the experience.
Real estate and infrastructure create permanence.
Community gives the entire thing purpose beyond the P&L.
That’s essentially what Monumental has become.
And increasingly, that’s what I think 4C could become in Montreal.
The Immigrant Parallel Matters, Too
There is another similarity I hadn’t really considered until recently.
Ted is the son of Greek immigrants. Monumental’s own history describes him that way.
I came to Canada from Iran as a child.
There’s something interesting about immigrants—or children of immigrants—eventually becoming obsessed with building institutions in the cities and countries that became home.
At first, you’re trying to establish yourself.
Then you’re trying to build something.
Then, if you’re fortunate enough to succeed, the question eventually becomes:
What can I build that is bigger than myself?
Sports franchises are unusual businesses in that respect.
You may own the equity.
But psychologically, the community owns the team.
And that has increasingly shaped how I think about the Expos.
From Team Owner to Platform Builder
The traditional sports ownership model is fairly straightforward:
Buy team.
Operate team.
Hopefully win.
Watch franchise appreciate.
Ted’s career demonstrates a much broader possibility.
The Capitals became part of Monumental.
Monumental became teams + venues + media + technology + entertainment.
And now the Capital One Arena project is expanding from roughly 900,000 square feet to 1.6 million square feet, as Monumental attempts to create what it describes as a major entertainment district.
That sounds awfully familiar to what I keep describing with 4C.
The Expos would play 81 home games.
4C is about the other 284 days.
That’s why I’ve stopped thinking about the Peanut Project simply as an attempt to acquire an MLB franchise.
The opportunity is potentially much larger:
Franchise + Stadium + Media + Entertainment + Culture + Commerce + Community.
The Expos would be the flagship.
Not the entirety.
Control the Vision, Not Necessarily All the Capital
There’s another lesson here that becomes increasingly relevant as professional sports valuations reach levels where even extremely wealthy individuals can struggle to finance franchises alone.
An entrepreneur doesn’t necessarily need to supply all the capital to lead an enterprise.
What matters is assembling the right capital around the right architecture while preserving the ability to execute the vision.
That is particularly interesting to me because the Peanut Project has forced me to think differently about what an ownership group could look like.
Family offices.
High-net-worth individuals.
Private equity.
Infrastructure investors.
Strategic media partners.
Corporate partners.
Potentially community participation where league rules permit.
The entrepreneur’s job isn’t necessarily:
Write every cheque.
It may increasingly be:
Assemble the puzzle.
The Outsider Eventually Gets Invited Inside
And perhaps today’s announcement is the most interesting part of the story.
In 1999, The Washington Post described Ted as an AOL executive entering a Washington sports establishment traditionally dominated by an older generation of locally connected business owners.
Twenty-seven years later, his fellow NHL owners have unanimously elected him to chair their Board of Governors.
Think about that progression.
Internet entrepreneur.
Media executive.
Outsider buying a hockey team.
Sports owner.
Platform builder.
And now chairman of the NHL’s Board of Governors.
There’s probably a lesson in there for every entrepreneur entering an industry where people tell you:
That’s not how things are done here.
Sometimes the outsider stays an outsider.
Sometimes the outsider learns the business, respects the institution, contributes to it, builds something meaningful…
…and eventually helps lead it.
Congratulations, Ted.
I’ve been watching the journey since the AOL days.
Today gives me another reason to keep watching.