Tony Khan told me something early in our conversation that I almost let slide past me. He said he launched AEW in 2019 because he saw an opportunity, and he seized it. Simple sentence. Founder boilerplate. Except when you pull the thread — why 2019, why wrestling, why TBS and TNT specifically — what you find underneath isn't instinct. It's architecture. Every piece of the launch was deliberate: the expiring contracts, the rights fee environment, the network history, the window that was sitting open for the exact right person to climb through.
He wasn't an outsider who got lucky. He was a lifelong fan who had been quietly building a thesis for decades and then executed it when the conditions aligned. That's a different thing entirely.
The episode is about what it actually takes to build a challenger brand in a space where the incumbent has been dominant so long that everyone assumes the game is already over.
The window most people don't see
Here's what Tony saw in April 2018 that most people missed: wrestling television rights fees were starting to move. For years, the business model for a wrestling promotion was pay-per-views and live event gates. Television was distribution, not revenue. Then the sports rights market started doing what it does — escalating, everywhere, across every property with a loyal live audience. And Tony recognized that the underlying economics of the business were about to shift in a way that made a well-positioned challenger viable for the first time.
He was also watching the network landscape. TBS and TNT had carried wrestling from 1971 through the early 2000s. Then the programming shifted and wrestling went dark on those channels for over twenty years. Tony's frame on that was pointed: when a network has deep history with a sport and then loses it, getting it back fits like a glove. He used the NFL returning to CBS after a few years away. He used the NBA going back to NBC. The brand memory doesn't disappear in the absence. It waits.
So he had the rights environment, the network fit, and — critically — a roster problem that was about to solve itself. Several top international pro wrestlers had contracts expiring at the start of 2019. They would be free. The timing wasn't coincidental; it was the last piece of the thesis clicking into place.
Most people see opportunity as a flash. Tony saw it as a convergence, and he'd been patient enough to wait for all the variables to line up simultaneously before moving. That patience is the thing that doesn't get reported when someone writes about AEW's rise.
What COVID actually cost — and what it built
When the pandemic hit in March 2020, AEW had been running Wednesday Night Dynamite for about five months. They were hot. The February 2020 pay-per-view, Revolution, was being called one of the best in recent memory. And then Tony had to cancel everything.
A live touring company with no live touring is, in the most literal sense, a fundamental business problem. What he did instead is the part I keep coming back to.
He moved every show to Jacksonville — to the amphitheater outside the Jaguars stadium — and he started filming in front of empty seats. Except he didn't film in front of empty seats for long, because he was watching television at the same time he was running a television company, and he noticed something. The Jimmy Fallon show had brought his staff into the room during the first week of COVID. Just the staff. Maybe ten people. And it sounded like a small comedy club — real laughter, real reactions, actual human energy in the room. Stephen Colbert had nobody. The difference between those two broadcasts was not ten people. It was the presence or absence of any signal that what was happening on screen mattered to someone.
So Tony put the wrestlers around the ring. The ones not working a given night became the audience. AEW was the first wrestling company to do this. Within months, he was selling sections of the outdoor amphitheater like a checkerboard — one family or group per section, separated, distanced, outdoors. Drive-in movie theater logic applied to a live wrestling event. It worked.
The same checkerboard setup was what the Jaguars used for week one of the 2020 NFL season — one of the only two teams with fans in the stadium that week, alongside the Chiefs. And that format ended up influencing how the Super Bowl handled attendance that year in Tampa.
The thing I've been turning over since we talked: the companies that came out of COVID stronger weren't the ones that survived it. They were the ones that treated it as a design constraint. Tony didn't just maintain AEW through the pandemic. He made Daily's Place — the amphitheater in Jacksonville — synonymous with a specific era of AEW that the fanbase now looks back on with genuine affection. He converted a catastrophic operational problem into a brand memory.
PULL QUOTE: "We came out much hotter than we went in." — Tony Khan
I've thought about this in my own investments. The deals I've seen go sideways during hard periods almost always had one thing in common: the team was trying to restore what they had before. Tony wasn't trying to restore anything. He was building something new inside the constraint, and the constraint made it memorable in a way the original version wasn't.
The challenger math
Tony made a comparison midway through the conversation that I want to spend more time on than we did in the room. He said AEW is the biggest sports startup since the AFL — the original American Football League, the pre-merger challenger that eventually became half of the NFL we know today. That's the last time, he said, that a challenger brand in a sport had the market share and consistency that AEW has now.
That's a real claim. He's not comparing AEW to minor leagues or regional circuits. He's pointing at the AFL — a league that successfully forced a merger with the dominant incumbent and in doing so restructured the sport permanently.
I don't know if AEW ends in a merger. Tony didn't suggest that. But the frame is worth taking seriously, because it explains something about the strategy that otherwise looks like stubbornness: he is not trying to be a niche alternative to WWE. He is trying to be big enough that the sport has to account for him. Those are different goals with different implications for every decision he makes — roster investment, television deals, international partnerships in Mexico and Japan, the Sports Illustrated promotion-of-the-year award he says he worked specifically to win back in 2025 after losing it in 2024.
A challenger that's satisfied being a challenger eventually becomes a footnote. A challenger that's building toward inevitability — that's a different animal. Tony thinks about AEW the second way.
There's something familiar to me in this. My career was built on the same principle: you don't just compete with the person across from you, you make them account for you on every play, whether you're the one doing the work that down or not. Presence changes the field. AEW changes the field for professional wrestling. Tony understands that, and he's building to it.
What the Darius Slay story actually reveals
There's a moment in the conversation — we're talking about his role as chief strategy officer for the Jaguars, and how talent evaluation actually works — where Tony mentions Darius Slay. He said he banged the table for Slay going into the 2013 draft, that it was crazy to him Slay fell as far as he did, and that Jacksonville had the first pick of the second round and didn't take him.
He didn't say it as a brag. He said it as a demonstration of the process: sometimes you're right and the group goes another direction, sometimes you're wrong and someone else has the better read. He was quick to add that second part.
But the Slay example points at the real thing he was saying about evaluation: game tape is the foundation, not the combine. Not the pro day, not the measurables alone — what actually happened in the games. He made this point more than once. The combine is part of the picture. The drills are part of the picture. But they are all different ways to document what happened in the games, and if those things are leading you to radically different conclusions, something is wrong with how you're reading one of them.
I was drafted second overall in 2010 partly on game tape and partly on combine performance. Tony knew that. He also knew — and brought up, unprompted — that his father had put in a bid to purchase the St. Louis Rams that same year, and that if the deal had gone through, his path and mine might have crossed in a very different way. Stan Kroenke had matching rights and exercised them. Worlds didn't collide. Tony called it ships passing in the night.
What I remember about 2010 is that there were a lot of decisions made that year — at every level, by franchises, by families, by players — that looked one way in the moment and revealed themselves over the next decade. Not all of them went the way anyone expected.
What I'd take from this, and what I'd do differently
Three things from this conversation that I'm genuinely going to act on:
- Look for the convergence, not the flash. Tony didn't wake up one morning and decide to start a wrestling company. He watched a thesis develop over years — rights fee trends, network history, talent availability, personal expertise — and moved when enough variables aligned simultaneously. The impulse in any fast-moving space is to treat timing as something you feel. Tony treated it as something you track. When I look at deals now, I want to know what the founder was watching in the two years before they moved, not just why they're excited today. The convergence tells you whether this is a thesis or a mood.
- Constraint isn't the enemy of brand. Sometimes it's the only way brand gets made. AEW without COVID doesn't have Daily's Place. Daily's Place is now part of AEW's mythology — a specific era that fans identify with and carry affection for. Tony made that happen not by fighting the constraint but by designing inside it creatively and fast. I think about this with the companies I'm involved with. The periods that feel like survival are often the periods that, if you handle them right, create the most durable audience loyalty. Customers remember how you showed up when things were hard. Investors do too.
- Market share is the argument. Quality is the evidence. Tony talked about Sports Illustrated, ESPN, New York Post, Yahoo — all recognizing AEW's quality in 2025. He talked about winning the promotion-of-the-year award back after losing it. That's not vanity. That's the challenger building the evidentiary record that their market share claim is legitimate. The argument for any challenger is that the incumbent's dominance is habit, not merit. You can only make that argument with proof. Tony is accumulating proof, award by award, year over year, deliberately. That's the discipline underneath the disruption.
Tony closed the conversation by asking if he could get me in the ring. I told him I'd skip wrestling and go straight to acting.
He didn't push it. But he was right that I could probably still fit through the ropes. The offer stands either way.