Morning folks, and welcome to today's episode called Michael Rubin of Fanatics: The Man Who Never Stops Selling, and he doesn’t, this guy is non-stop business— even when he’s partying, it’s business. Here’s a guy who owned 5 retail stores while still in high school, was making millions by the time he was 18, was CEO of a public company at just 23, and over the last 10 years he has transformed the whole sports licensing and sports fan business through Fanatics, a $25 billion company that’s still private. Rubin is just 100% non-stop hustling, and I would say he’s the most relentless business person I’ve covered up until now and he makes for a fascinating story— enjoy.

Michael Rubin was born in 1972 in Philadelphia. His mother was a psychiatrist. His father ran a veterinary practice. So a very comfortable middle-class suburban upbringing.
But you wouldn’t think that of Rubin. He’s not polished— he curses, he’s pretty rough and ready, and I think that’s because he was always hustling. By the time he was eight, he was selling stationery door to door, he had a team of 5 or 6 friends who worked for him clearing the snow off people’s driveways.
I listened to an interview where Rubin explained why he got into business so early— he wasn’t much good at school, he had dyslexia, ADHD, he was no good at sports, he was always the last to be picked on any team— and that’s got to hurt when you’re as hyper-competitive as Rubin is— because that is his defining feature— ultra-competitive— so when he found at such a young age that he was good at business, at hustling, he went for it 100%— business is where he could win, and in every interview I’ve read or listened to with Rubin, and I actually believe him when he says that he was never driven by money, he was always driven to win— and he was just relentless from the age of 8.

By twelve, he set up a ski-tuning shop in his parents' basement.
Then in 1986, on his fourteenth birthday, he took $2,500 in Bar Mitzvah money, as well as about $7,500 in savings, and signed a lease on a real retail space— well, technically his father signed it because he was still only 14— and called it Mike's Ski and Sport.
He stocked it with ski equipment — overstock from previous seasons — that he bought at deep discounts, and this pattern of buying distressed inventory cheap and moving it fast, it kinda became his MO.

In its first year the shop made a profit of $25,000 and he ended up opening 5 locations across Pennsylvania and New York— now when I read that, I had to stop— hold on a second, this guy opened a store at 14, and while still in high school he had 5 stores? How, like how did his dad sign a lease for him at just 14? How did suppliers, landlords, employees take him seriously? Rubin said he just did it, that’s it, just do it, never hesitate, he was never worried about what people thought or about the fact that he might have no experience— and this is the thing about Rubin, I think, for him, business, the hustle, the selling, the work— it’s not a grind for him, I can’t really put it into words, but I suppose business isn’t something he does, it’s who he is.

Anyway, back to 1988, he bought himself a Porsche— which he couldn’t even drive because he was too young— and he’s admitted that at this stage he was a pretty cocky young guy.
But he soon got taken down a peg or two because the thing about a ski business is it’s dependent on snow. And in the winter of 1988, there was basically no snow in the Northeast. Demand collapsed. He was sitting on $100,000 of inventory while he had landlords and suppliers looking to be paid.
He had to hire a bankruptcy attorney but because he was a minor, the creditors’ legal position was weak.

So instead of forcing bankruptcy, they negotiated a settlement.
His father lent him $37,000 to settle but the loan came with a condition— he had to go to college.
He agreed and enrolled at a local college but of course, he couldn’t stop hustling— within just a few weeks he came across a load of overstock sports gear, he borrowed $17,000 from a friend, resold the equipment for $75,000 and left college to set up KPR Sports International (an acronym for Ken and Paulette Rubin— his parents' names). I’m guessing he was thinking, my folks are going to be really pissed at me but maybe by naming the company after them it will soften the blow.

The business focused on buying distressed inventory and selling it on to discount retailers like T.J. Maxx. And Rubin had unbelievable moxie. I heard him tell this story on a podcast that perfectly captures it. He’s about eighteen or nineteen years old and he finds a deal for 300,000 pairs of sneakers at $9 a pair. So that’s about $2.7 million worth of shoes. But he already has a buyer lined up at $15 a pair. So $1.8 million profit.

Rubin rings up his bank manager and says, “Hey, great news. I’ve just bought these sneakers for $2.7 million and I’m going to make $1.8 million.” And the bank manager says, “Well that’s great, Michael… but why are you telling me this?” And Rubin says, “Well… I need the $2.7 million first to buy them.”

And the bank manager wires him the money— still a teenager and the bank is giving him $2.7 million for a deal.
The thing about Rubin, he’s not just a talker— he works his ass off— eighteen hours a day travelling to trade shows, networking non-stop.

Then in 1994, he launched his own sneaker brand called Yukon and the timing was perfect, as discount chains like TJ Maxx were expanding rapidly and by the end of 1994, KPR's revenue was $50 million.

In 1995, Rubin spotted Ryka, a publicly traded women’s athletic shoe company that had hemorrhaged $14 million. On paper, Ryka was a sinking ship. But Rubin could see value where others couldn’t and he invested $8 million to acquire a 40% stake, and at just 23, he was among the youngest CEOs of a NASDAQ-listed company.

Rubin renamed the company Global Sports Inc or GSI. He shut down Ryka’s direct-to-consumer strategy, he funneled the excess inventory through his discount retailers.

And by 1998 revenue was at $130 million.

But the margins were tight. You’re dependent on retail buyers. You’re constantly managing inventory risk.

And remember this was 1998, the internet was emerging and gaining steam. So a market analyst phones Rubin and says, you know you should really look at this internet thing— this was Rubin’s reply: "Fuck this internet thing. Don't waste my time. It's all these young kids who don't make any money." And look in a way, he wasn’t wrong— there was a lot of bad online businesses launching back then.

But the analyst pushed back. And Rubin phoned the CEOs of his biggest retail clients and they all told him the same thing:

Board pressure is mounting.
Everyone is talking about Amazon.
No one knows how to respond.

As Rubin later said: “Every CEO I met was terrified of Amazon but clueless about building online operations.”

So this was a huge gap that Rubin was ideally placed to plug— now he had zero experience in building websites and running online businesses but he did have warehouses, he was moving the product, he understood the inventory flow.

It’s a huge opportunity but also a huge risk and pivot— but Rubin goes for it— he sells off the footwear brands to free up capital and by the end of 1999, GSI was live with its first clients — 4 large US-based sports retailers. And when I first looked at the deal structure, I thought, no way. Because for every product sold through the retailer’s website, GSI kept about 92.5% of the sale price. The retailer got a 7.5% commission.

But you have to look at who was actually carrying the risk here.

GSI was effectively running the entire online business for these retailers. GSI bought and owned all of the inventory with its own money. If it didn’t sell, Rubin absorbed the loss. On top of that, GSI built a huge, state-of-the-art warehouse, ran the servers, the shipping and customer service.

So from a retailer’s perspective in the early days of the internet, that 7.5% was pure profit.

Now, later, as the industry matured and retailers got more comfortable with the internet, the model evolved, those commissions were re-negotiated.

So GSI was investing millions into technology, logistics, and like every internet company was running at a loss because they were investing for the future.

And then— we all know what happened. March 2000— the bubble burst, GSI’s share price went from $30 to $1, the company was running out of cash. But again, and this speaks to Rubin's ability to hustle, at a time when no one was investing in anything to do with the internet, he managed to get a $100 million investment. Now in return of course the investors took a huge chunk of his business, but he survived and then over the coming years GSI thrived by picking up big contracts from the likes of Kmart and QVC.

And over the next 7 years Rubin bagged big clients like Ralph Lauren, Timberland, Calvin Klein, and GSI was also handling the official ecommerce sites for the NFL, NBA, NHL. So by 2011 revenue was over $1 billion.

Now it’s in 2011, and Rubin briefly becomes a reality TV star when he appears on Undercover Boss. If you don’t know the format— it’s basically where the CEO goes undercover in his own company with a view to seeing what’s working and what’s not working.

I watched the show and I gotta say, I like Rubin. Yeah the program is schmaltzy, it’s edited, I get that, but he was genuinely interested in the people who he works with on the program— he connects with them on a very human level.

And a few other things I noticed:

First of all he’s changed a whole lot since then— back then he looked kinda unhealthy, drawn, a little bit heavier— he definitely has transformed himself over the last decade or so.

Also, what’s made very clear in the program, and it’s no surprise, is that he works non-stop— Rubin himself characterises it as running so hard that he doesn’t know when to stop. I mean even when you listen to him, he’s got this croaky kind of voice— and I’m pretty sure that’s from just non-stop talking, selling, dealing— in the program his wife says it’s 24/7 texting Europe at 3.00am, so it’s no surprise that later that same year, 2011, his marriage ended.

And 2011 turned out to be a huge year for his business. First of all there was the acquisition of Football Fanatics for $275 million, so a bit of background on this acquisition.

As mentioned GSI was already handling the official ecommerce sites of all the major pro sports. Football Fanatics had been set up by 2 brothers in Florida as a brick-and-mortar store but business really took off with the internet. The business focused mainly on college sports— so it was a good, complementary addition to what GSI was already doing.

Now around this time Rubin was thinking about where GSI was going. He could see that the technology was becoming commoditised and retailers would eventually either build their own systems, or he’d be continually competing on price against companies similar to GSI.

So when eBay came calling in 2011, and offered $2.4 billion for GSI, a 51% premium on the market price— Rubin grabs the opportunity, pocketing $150 million personally. Now eBay didn’t want the sports side of the business at all, so they asked, as part of the overall deal, if he would buy that part back for $350 million.

So Rubin had already been considering how to optimise the sports side of the business— he thought that sports itself and the fan side of sports was a real growing sector, and had huge potential.

But he also knew that if he remained a traditional middleman, giants like Amazon and Alibaba would eventually 'eat his lunch.' He realized that to survive, he couldn't just resell merchandise that was made and controlled by other suppliers— he had to own the entire value chain. His vision was to move from being a vendor to a strategic partner, building a 'Vertical Commerce' model that gave teams and leagues a direct line to their fans and a bigger slice of every dollar spent— so this was his vision but it would take a few years to get to where he wanted to be.

Now on a slight tangent, but not really, we’re still in 2011 and Rubin joined a group of investors led by Josh Harris and takes a minority stake in the Philadelphia 76ers basketball team, and New Jersey Devils— a hockey team— now listeners might be familiar with Josh Harris— he pops up in the episode on Leon Black, because he is one of the top 3 in Apollo Management.

By this stage the company was leaning heavily into what Rubin called a “mobile-first” strategy and something they referred to internally as “hot markets” or event-driven commerce. The idea was pretty simple: capture the emotional moment. When something big happened in a game — a championship win, a record play, a breakout performance — Fanatics’ systems could detect the spike in demand almost instantly and then they reacted fast — printing and shipping merchandise almost immediately so fans watching the game on their phones could buy the gear right there in the moment.

But as mentioned, at this stage Fanatics still weren't a manufacturer.

What they were doing was buying huge volumes of blank jerseys and shirts from licensed suppliers and storing them in their own warehouses. Then whenever a big moment happened workers would use high-speed heat-press machines to add the relevant graphics onto those blanks.

In effect it was a kind of industrial print-on-demand system for sports merchandise.

But they still couldn’t actually manufacture authentic material themselves— they weren’t licensed to do so— in other words for example, if they ran out of blank blue jerseys during a Dodgers playoff run, they were stuck waiting for a supplier to ship more.

And that’s why 2017 was such a big turning point. Because that was when they bought Licensed Sports Group and this was when the first big part of Rubin’s vertical commerce strategy was put in place.

With this deal, Fanatics took ownership of the complete manufacturing for Major League Baseball.

Then a few months later, with revenue at over $2 billion, Masayoshi Son’s SoftBank Vision Fund led a $1 billion investment round that valued the business at about $4.5 billion. But the really interesting thing about this round wasn’t the valuation — it was the other investors because they were the NFL, Major League Baseball, National Hockey League, and that fundamentally changed the dynamic because now with the pro sports organisations as his actual business partners, Fanatics was going to get all of their business.

In essence, this was the second crucial element of Rubin’s vertical strategy.

The first big deal came in 2018 with the NFL–Nike–Fanatics structure. Nike remained the brand — designing the products and putting the ever-desirable swoosh on the jersey — but Fanatics took over the manufacturing and distribution of all Nike-branded NFL fan merchandise.

And once that model proved it could work, it started spreading. Similar structures followed with the other pro sports leagues.

Now this next chapter in Rubin’s life, it’s a bit of a tangent— it’s a friendship that I suppose you could say opened the door to his crossover into the cultural mainstream.

So this friendship started in 2015 at an NBA All-Star Game in New York.

Rubin is there courtside and is sitting next to the rapper Meek Mill— they had no idea who each other was, but they started talking, quickly bonded over the fact that they were both from Philly.

Rubin is known for interrogating people. Rapid-fire questions. How does that work? Why does that work? What’s the incentive structure? He does it to CEOs, athletes, politicians. It’s how he learns.

They start talking regularly. Sometimes daily. And they become great friends. Then November 6, 2017 Meek is in court for a probation violation. Now for context, Meek has had a lot of run-ins with the justice system, but what he’s in court for this time is very much a technical issue— the probation officer and even the prosecutor recommend no prison time.

But the judge ignores them and sentences Meek to two to four years in state prison.

Rubin’s in the courtroom. He’s not only devastated, he’s outraged, and he wants to do something about it. He started looking at the whole justice system— he realized that while many people were focused on prison reform, far less attention was being paid to the funnel — probation and parole.

He finds out that about 175,000 people a year were being sent to prison for technical violations.

Missing a meeting.
Breaking a curfew.
Rule breaches rather than new crimes.

And before any of you hard-asses out there go, serves them right— this is costing US taxpayers billions every year.

So in January 2019, Rubin launched the REFORM Alliance alongside Jay-Z, Robert Kraft and Meek Mill, who had since been released and the courts vacated his original conviction.

By 2024, REFORM had helped pass 21 bipartisan laws across 12 states, moving over 850,000 people off the probation-to-prison pipeline.

His public profile got another bump in 2021, when he started hosting this Fourth of July white party at his $50 million mansion in the Hamptons.

The party is capped at four hundred people— all dressed in white. Leonardo DiCaprio. Kim Kardashian. Tom Brady. Beyoncé. League commissioners. Rappers. Tech founders. You get the idea — celebrity, sport and business power all in one place.

And make no mistake, for Rubin these parties are all about business because it’s fair to say that in Rubin’s world, there really isn’t any line between business and pleasure, it’s all the one— here’s a quote from Rubin: “I’m not embarrassed to say this [but] I don’t have hobbies. Business is my life, it’s what I love to do. Some people are like, ‘Oh you have to get a work-life balance.’ I don’t want to. It’s not who I am.”

Anyway these parties, they’re a bit over the top for my liking, for example in 2024 each invite was personalised with an original piece of art by George Condo, a famous artist, apparently. I’d never heard of him but then again I know jack about art. Each invite is estimated to be worth over $35,000 on the private market. People were so desperate to get into the party that they’ve offered up to five million dollars for an invite. And of course Rubin turns them down. Which of course only makes it more exclusive.

Now after P Diddy’s fall from grace, the phrase “White Party” didn’t sound so glamorous anymore— Diddy had popularised the whole white party thing in the 2000s. And as a result 2024 was Rubin's last one.

But, back to business, in 2021 Rubin pulled off another fantastic deal when he secured exclusive long-term trading card licenses from MLB, the NBA, and the NFL.

Now you have to understand, Topps had been making baseball cards for seventy years. Panini controlled basketball and football. These were entrenched cultural institutions.

And overnight, it all moved to Fanatics. And you have to feel some sympathy for Topps— they had been preparing to go public at a $1.3 billion valuation. But once Fanatics secured the league licenses, the public offering was pulled.

Rubin then swoops in and buys Topps for around $500 million— because there’s still incredible value in their specialized manufacturing factories, a skilled workforce, and an invaluable archive of intellectual property.

By this stage with revenues of $3.5 billion, Fanatics is valued at $27 billion.

Then in 2022, Rubin has to sell his stake in the sports teams because now Fanatics moves into betting and owning a team creates conflicts with league rules.

And Rubin is betting big on gambling— over the last few years Fanatics has spent $1 billion building this side of the business— it’s still a small player, only about a 5 per cent market share. But Fanatics has direct marketing relationships with over 80 million sports fans. And when you combine that with Rubin being the kind of ultra-competitive hustler that he is, I wouldn’t be surprised if this becomes a huge growth market for Fanatics.

But this is one part of Rubin’s business that I’m wary of. Because sports betting today isn’t really about picking the winner of a game anymore. The industry has moved towards what they call in-play betting — basically hundreds of tiny wagers inside a single match. Who scores next. Who gets the first corner. More than 60% of online betting revenue now comes from live in-play bets.

And the reason they push those bets is simple: the margins are much higher. A normal game bet might give the bookie a 5% margin. These micro bets can be 15–25%.

And the other stat that really jumps out is how concentrated the revenue is. Studies suggest the top 1% of gamblers generate around 35–40% of total operator revenue, and the top 5% produce close to two-thirds. Which means the industry is heavily dependent on a tiny group of extremely active players. And when you combine that with apps that know exactly how and when people are betting, sending them bonuses and notifications to keep them playing, I think this is a sector that’s setting itself up for a lot of litigation down the road. And what's even more concerning is that these are smart people, they’re probably aware of the future litigation issues and are planning and factoring all this into the business model. And if that's the case, then they're being so cynical and exploitative, but look, I’m only speculating.

Now it hasn’t all been plain sailing. In 2024 Fanatics and Rubin took a serious hammering over the new Major League Baseball uniforms. Players said they were see-through. Papery. Cheap. Fanatics said they were simply manufacturing exactly to Nike’s specifications, which turned out to be true. But reputationally the damage was done for a while.

In 2025 revenue was over $8 billion, with a valuation drifting down slightly to about $25 billion. The company is still private, Rubin owns roughly thirty percent but has a majority voting control. And Rubin doesn’t really see Fanatics as a mature company yet. In January he talked about pushing total platform revenue toward fifty billion dollars over the next decade with the ambition of having everything on the 1 app.

You buy a jersey. You buy a trading card. You place a bet.

And there are other opportunities in the sport sector that they could tap into— like media, tickets.

There could well be some big stumbling blocks— I already mentioned the issues around gambling, and there’s also their dominance— questions could be raised over them having a monopoly.

But overall what Rubin has built is an amazing business ecosystem. And as a person, I like the guy— yes, he’s all business, but so what— it’s what he actually loves, you can just hear it in every interview— business is his life, and he probably doesn’t have much of a personal life, and sacrifices a lot of his family life, which is something I wouldn’t be able to do, but it’s the choice he’s made and he’s happy to live with. And while he is all business, a total workaholic nut job, he also comes across as a very decent guy, and a fascinating business story.

And that brings us to our listeners' emails and this one I’m delighted to say is from a person I actually did an episode on— Foster Winans, the journalist from the Wall Street Journal who got caught up in an insider trading type scandal back in the 80s— and Foster writes:

What a trip listening to the sordid tale of my undoing in your Irish accent. You did your homework and it shows. Good job.

And just to point out— I didn't read that email just so I would look good— well maybe just a little bit, but I wanted to read it because I think it shows what a classy guy Foster is— I hope you're still listening Foster and thanks so much for the email.

And remember if you have any comments, any corrections or any story you'd like me to cover, email us at: info@gbspod.com

All the best folks