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What It Means to Be a “Real” Entrepreneur | Michael Rubin, Fanatics

Michael Rubin is the founder and CEO of Fanatics. He grew up outside Philadelphia, started tuning skis at 12, opened a ski shop in his parents' basement at 13, and had a storefront in a shopping center by 14.

David SenrahostMichael Rubinguest

Nov 15, 20261h 8mWatch on YouTube

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Chapter summaries

Why billionaire stories often feel boring—and why Rubin shares the messy parts
Michael Rubin explains that extreme wealth doesn’t automatically make someone interesting; what people actually want are entrepreneurial stories with mistakes and reversals. He says being self-deprecating and honest about failures is more compelling than a polished image, and he gives an example of ignoring PR pressure to “just be yourself.”
- •Wealth accumulation isn’t inherently interesting; entrepreneurial journeys are
- •People want to hear what went wrong, not only successes
- •Rubin says he’s highly self-deprecating and comfortable sharing mistakes
- •He argues many businesspeople aren’t authentic, often due to image management
How Rubin uses relationships and outside input to navigate constant problems
Rubin says business disasters happen daily or weekly, and his default is to ask for input without pride. He describes Fanatics as a relationship-driven company and emphasizes that pressure from passionate sports fans forces improvement when things go wrong.
- •Rubin frames problem-solving as constant in his work life
- •He says he’s quick to ask others for help and perspectives
- •Fanatics’ mission is described as relentlessly enhancing the fan experience
- •Sports fans celebrate good execution and punish mistakes, which Rubin says makes the company better
Robert Kraft’s advice: slow down, protect the long game
Rubin names Robert Kraft (and Kraft’s son Jonathan) as key long-term mentors with no agenda beyond helping. He shares a story where Kraft urged him to pause after a counterparty violated a deal, reminding him that reputations and relationships matter over decades.
- •Rubin identifies Robert Kraft as his most frequent go-to advisor
- •A deal was violated by an important sports figure, triggering Rubin’s anger
- •Kraft advised taking a breath, sleeping on it, and thinking long term
- •Rubin says waiting helped him respond rationally and reach a good outcome
Near-bankruptcy at 16: arrogance, no snow, and the pivot into closeouts
Rubin recounts building a ski business as a teenager, then nearly going bankrupt when he overextended and a season lacked snowfall. He explains how legal constraints on minors’ debt and a scrappy inventory purchase turned the crisis into an entry point for the closeout business.
- •Rubin started with a basement ski shop and expanded quickly as a teen
- •At 16 he overextended, believed his own hype, and got hit by a bad season
- •He faced $200k in bills with $80k in inventory and hired a bankruptcy attorney
- •He settled debts cheaply, bought auctioned inventory, and moved into closeouts
2009 margin crisis: hours from losing the company—and why he loved it
Rubin describes borrowing against stock value, then getting crushed when the financial crisis dropped the stock 90% and reduced bank advance rates. He says he was hours from being margined out until he finally recovered the last money locked in a hedge fund—and he found the whole experience energizing rather than frightening.
- •Stock collateral collapsed and borrowing capacity shrank dramatically
- •He worked to retrieve capital from funds but got stuck on the final amount
- •He says he called one manager relentlessly until the money was returned
- •Rubin says he enjoyed the adrenaline and found survival situations intellectually interesting
From crisis to exit: eBay buys the company and Rubin’s persistence philosophy
Rubin explains that after surviving the 2009 crisis, the company was acquired by eBay in 2011. He credits persistence—continually working the problem—and argues many people give up too early when conditions look bleak.
- •Rubin recalls owing a bank and narrowly avoiding forced share sales
- •He says the financial crisis ending helped reset the environment
- •He describes eBay’s strategic interest in the company’s e-commerce services
- •Rubin emphasizes staying calm and continuing to work problems to reach solutions
What a “real entrepreneur” is: born for it, addicted to it, never stops
Rubin defines a “real entrepreneur” as someone with innate drive who genuinely loves the work and can’t quit. He contrasts that with people who cash out and lose interest, then says he intends to keep building for life—comparing business longevity to athletes’ finite playing careers.
- •Rubin says entrepreneurship is largely something you’re born with
- •He defines real entrepreneurs as people who love it and are addicted to it
- •He contrasts lifelong builders with those who stop after making vast wealth
- •He says he’ll keep going as long as he’s alive and able
Learning from elite athletes: killer instinct, competitiveness, and transferable habits
Rubin says time around top athletes taught him to identify who will excel by their “killer instinct,” not just talent. He describes close friendships with athletes and argues that the same competitive habits and work ethic that drive championships translate directly into post-career business success.
- •Rubin distinguishes talent from “killer instinct” as the deciding factor
- •He describes intense competitiveness as a predictor of achievement
- •He says elite athletes carry their work ethic into business
- •Rubin frames adversity as motivation rather than an excuse, especially for entrepreneurs
Fanatics today: three businesses and a competitor lawsuit Rubin enjoys fighting
Rubin outlines Fanatics’ three primary businesses—fan gear (commerce), betting/gaming, and collectibles—then describes major litigation with a competitor. He argues the collectibles space was full of weak competitors, and says he finds the lawsuit intellectually engaging because he “loves the fight.”
- •Fanatics’ businesses are described as commerce, betting/gaming, and collectibles
- •Rubin says betting became harder due to prediction markets entering the ad landscape
- •He claims Fanatics innovated heavily in collectibles and grew the overall hobby
- •A former rights-holder is suing Fanatics, and Rubin says he enjoys the battle
Fanatics as a digital sports platform: leveraging fan relationships and selling across products
Rubin explains that Fanatics’ biggest asset became its relationship with tens of millions of fans, which expanded to 140 million. He describes the strategic advantage of offering multiple products to the same customer and says the company’s best customers use more than one Fanatics product.
- •Rubin says the key asset is the fan relationship, not only commerce operations
- •He describes Fanatics as a digital sports platform serving many fan needs
- •He lists multiple fan touchpoints: merchandise, cards, marketplace, live buying, betting, events
- •He says organic growth is core, with selective acquisitions for speed or capability
“Number one is everything”: competing in betting, views on prediction markets, and refusing to invest
Rubin stresses a company should push to be number one, calling number three irrelevant and number two unpleasant. He discusses prediction markets as a near-term complication for sportsbooks, predicts today’s construct won’t persist, and says he has “0.0 chance” of investing at current valuations.
- •Rubin describes a leadership theme: number one matters most
- •He calls the messy, competitive betting market “fun” and likes the challenge
- •He says prediction markets likely won’t look the same a few years from now
- •Rubin says he would not invest personally in leading prediction market companies at current valuations
Reinventing trading cards: innovation, athlete engagement, and explosive growth
Rubin explains how Fanatics entered collectibles after seeing minimal product innovation and under-monetization by leagues and unions. He details new product concepts like debut patches and achievement-based cards, describes building a secondary marketplace that shares economics with partners, and cites rapid growth from the business’s early revenue to much larger scale.
- •Rubin says leagues/unions were earning relatively modest sums and not participating in secondary sales
- •Fanatics offered guarantees, higher royalties, equity, and secondary-market participation to win rights
- •He describes debut patches as unique one-of-one items tied to a player’s first game
- •He says adding achievement-driven card elements and real marketing expanded demand and athlete involvement
Expanding from sports into entertainment collectibles—and Rubin’s “art for sports fans” framing
Rubin describes growing entertainment trading cards (Disney, Marvel, Star Wars) and observes most collectors span multiple categories. He then connects collectibles to the art world, calling cards “art for sports fans,” and explains how learning from artists led to collaborations that blend fine art with trading cards.
- •Rubin says entertainment collectibles are growing fast from a smaller base
- •He notes collectors often collect across sports and entertainment, not just one category
- •Rubin compares collectibles to art markets and calls it “art for sports fans”
- •He describes collaborating with artists to create original hand-painted card concepts and broader distributions
Deal-making evolution: learning by observing, fixing mistakes, and prioritizing partnerships
Rubin says he learned deal skills from many people and from repeated mistakes, emphasizing reputation and fairness over “winning” negotiations. He shares examples: a highly successful Lids deal and a Mitchell & Ness investment that soured, after which he chose to return partners’ money with a modest return to do right by them.
- •Rubin says he learns constantly from a wide range of people, including his kids
- •He says early on he focused on winning deals, later shifting to winning partnerships
- •He contrasts the Lids outcome (major success) with Mitchell & Ness trending down after acquisition
- •He describes returning investors’ money (and earlier returning NFT investors’ capital) to protect long-term trust
Long-term relationship compounding—and the director who stopped a ‘really dumb’ move
Rubin reinforces that he optimizes for long-term relationships with athletes and sports properties, aiming for partners who root for Fanatics. He highlights Silver Lake as a major investor and describes weekly conversations with a key director who recently talked him out of a major decision—prompting Rubin to call and thank him for “saving” him.
- •Rubin says relationships matter most when things go wrong and partnerships get tested
- •He describes the scale of Fanatics’ partner network (athletes and properties) and the need for trust
- •He names Silver Lake as a major outside investor and references frequent discussions with a director
- •Rubin recounts being talked out of a major plan and credits listening as critical to longevity

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