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There's a certain kind of person who hears the word "no" and treats it like a clerical error, a typo, something a polite follow-up email will surely correct.

Ashkan Karbasfrooshan is that person.

He built WatchMojo into one of the biggest channels on the planet. Seventeen billion views. Forty million subscribers. From Montreal, of all places, not LA, not New York, not some glass tower in Silicon Valley. And for fifteen years he did it without taking a single dollar of anyone else's money. Six of those years he lost money. He took out a second mortgage. He calls the whole arc "a ten-year overnight success," which is the kind of line that sounds humble until you sit with it and realize it's actually a flex about pain tolerance.

The marriage part is where it gets properly unhinged. He sat his wife down, the woman who would become his co-founder, and made the pitch with a straight finance-guy face. As he tells it, she'd said something supportive and he replied, "you don't know what you're talking about," not as an insult, he insists, but as a recruitment strategy. The closer? "The extra risk of you joining is actually minimal." Reader, there had already been a second mortgage. There would later be a miscarriage during the worst of it. "Minimal" is carrying a great deal of weight in that sentence.

That's the warmup act.

The main event is that he now wants to bring Major League Baseball back to Montreal. The Expos left in 2004. He watched them go, tried to save them as a self-described "bigger nobody" than he is now, and then forgot about it for the better part of twenty years. Then on November 29th he watched a hockey game, saw a jersey from a team that had also been ripped out of a Canadian city, and something detonated. "Is it impossible to bring them back?" he asked himself. "Nothing's impossible. It might be improbable, but how do you make it inevitable?"

The answer, it turns out, is roughly four billion dollars he does not personally have, a stadium that does not yet exist, and a strategy that is mostly phone calls. He talks about widening the buyer pool the way a hitter talks about a slump: "I have to expand the strike zone." He swallows his ego on calls where family-office gatekeepers ghost him, ridicule him, move the goalposts, and he insists it only feeds him. "What does it take to make this happen," he says, "and then I'll just go through a wall to make it happen."

He has a name for the whole philosophy. The permission fallacy. Nobody opens the door for you. Nobody extends the table. So you build the thing nobody said you could build, and you do it loudly, right up to the line and not over it.

In this issue we get into all of it.

We get the four-quadrant theory of using AI without setting your own brand on fire, complete with his very on-brand observation that AI is just a tool, "like a hammer. I could build a house with it, I could kill somebody." We get Cyrus the Great recast as a management consultant, the leader who conquered through his word more than his sword, because "it's not force, it's finesse." We get the triple crown he swears by, persistence, resilience, and patience, and the paradox that entrepreneurs are simultaneously the most impatient and most patient people alive. We get "we're entering an era of wisdom, not knowledge," which is either profound or a great T-shirt, possibly both.

And we get the desert-island question, the one where his entire empire is theoretically on fire behind him and we ask what he'd grab. No empire. No four-billion-dollar baseball dream. No investors. "My wife, my two daughters, and yeah, probably my dog Lily." When we pointed out that the dog, a Shih Tzu, had just beaten Warren Buffett and every billionaire in his contacts, he didn't blink. "Does she know that I chose her over Warren Buffett? I don't know if she knows. I was told she has the intellect of like a two-year-old forever, but I think she feels the love." The dog has no idea she won. This may be the healthiest relationship in the entire episode.

Watch the full episode here. It's funny, occasionally feral, and the last ten minutes get quietly moving in a way I did not see coming when we started talking about poutine.

But meet the man first, because honestly that is the better story, and I do not say that about many people in this business. Ashkan Karbasfrooshan built one of the biggest channels on the planet out of Montreal, on borrowed clips and a second mortgage, then forgot about the baseball team he once tried to save, and then a random hockey jersey detonated something twenty years buried and now he wants to spend four billion dollars he does not have to bring the Expos home. Nobody builds that arc by accident. Part Two is the autopsy, the part the press release quietly deletes. The ownership math MLB does not advertise, the 30% private-equity ceiling that means he is not the buyer and never was, the control person problem hiding under all the charm. A man who insists this is not about a baseball team while building a 365-day media empire around a stadium that does not exist yet. A precedent named Bronfman, richer and better-connected, who tried the exact same thing and got told no in 2022. Then Part Three is the deliverable: the 90% / 33-to-50% odds in his own words, the stadium gap that gates the whole decision, the Vancouver problem nobody in Montreal wants to say out loud, and the one question to ask before you believe any expansion pitch ever again. Plus the downloadable one-pager. Join ADOTAT+