By playing, you agree to uListen's Terms and Privacy Policy and YouTube's Terms of Service.

Jay Shetty Podcast

Jay-Z's Business Partner: How To Transform Your Passion Into Profit (& make MILLIONS)

In this episode, we welcome Fanatics CEO Michael Rubin: a distinguished businessman and social justice advocate known for spearheading several multibillion-dollar direct-to-consumer ventures, specifically in licensed merchandise, trading…

Michael RubinguestJay Shettyhost

Dec 18, 202344mWatch on YouTube

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

Great conversations run long. Their best ideas don't have to.

uListen is free on iPhone, iPad, Android, Chrome, and Claude.

CHAPTERS

Jump to publisher timestamps

Chapter summaries

Entrepreneurial courage: ignoring “net worth” and embracing failure
Michael Rubin opens with a blunt mindset: he doesn’t care about net worth and doesn’t want to hear excuses that start with “but.” He frames entrepreneurship as having the courage to fail, describing near-bankruptcy experiences and attributing his outcomes to persistence and ambitious goals.
- •Michael Rubin says he doesn’t care about his net worth and rejects excuse-making
- •He ties entrepreneurship to courage and repeated attempts despite failure
- •He says he’s faced extreme setbacks, including almost going bankrupt multiple times
- •He argues that easy goals are effectively choosing failure
Childhood hustles and finding the one thing he was good at
Asked about his first job, Michael Rubin describes being a poor student and athlete but naturally drawn to work and business. He recounts multiple early hustles starting around age eight, emphasizing that he gravitated toward what he enjoyed and excelled at.
- •Michael Rubin says he struggled in school and sports but loved working
- •He describes early side hustles: trading cards, organizing snow shoveling, selling seeds, making stationery
- •He explains he sold to people with money (like friends’ parents) and organized other kids to do the labor
- •He says he’s been doing entrepreneurship since age eight
Born vs. learned hustle: being a “sponge” and learning from people
Jay Shetty asks how Rubin recognized his strength so young and whether hustle can be taught. Rubin says he believes he was born with it, but also that people can learn by observing others, taking the good and learning from the bad.
- •Michael Rubin says he was ‘born’ with entrepreneurial hustle and still loves working intensely
- •He says entrepreneurship skills can be learned by surrounding yourself with people you admire
- •He recommends taking what works from others and consciously ignoring what you don’t respect
- •He describes constant learning as necessary to keep improving
When entrepreneurship became “cool” and why collectibles feel personal
The conversation shifts to how entrepreneurship’s social status changed over time. Rubin says it used to feel nerdy until the dot-com era, and he connects his current collectibles focus to his childhood trading-card roots and the industry’s entrepreneurial culture.
- •Michael Rubin says entrepreneurship wasn’t celebrated early on and felt ‘weird’ or ‘nerdy’
- •He says it became cool around the dot-com era
- •Jay Shetty contrasts earlier career aspirations with newer generations wanting to build their own
- •Rubin highlights the collectibles business as entrepreneur-heavy and personally relatable
Modernizing trading cards: buying Topps and pushing real-world innovation
Jay asks how collectibles have evolved, and Rubin explains Fanatics’ significant entry into the space and ownership of Topps. He says the category had lacked innovation and marketing, then gives an example of creating a “debut patch” one-of-one card tied to a player’s first game jersey.
- •Michael Rubin says they got into collectibles in a major way about three years ago and now own Topps
- •He describes the industry as having an incredible collector base but a dated consumer experience
- •He frames the lack of innovation as a major opportunity
- •He shares an innovation: taking a debut-game jersey patch and embedding it into a one-of-one card
Three businesses, physical fandom, and how digital tools help
Rubin outlines Fanatics’ three core business areas: merchandise/commerce, collectibles, and online sports betting/iGaming. He emphasizes that physical products still dominate key segments, while AI and digital tools help operations and effectiveness.
- •Michael Rubin describes Fanatics’ commerce business (including merchandise and headwear) as strongly physical
- •He says AI can make both commerce and collectibles more effective
- •He names the third business as online sports betting and iGaming
- •Jay Shetty highlights that not all meaningful innovation has to be purely digital
Common entrepreneurship mistakes: not taking the swing, weak teams, and no joy
Jay asks what mistakes people make when entrepreneurship is trendy. Rubin says it’s not for everyone, but if it is for you, the first hurdle is taking action and accepting failure; then building with great people; and finally genuinely enjoying the work.
- •Michael Rubin says many people stall behind “I’ve got this great idea, but…”
- •He calls courage to fail essential and says failures teach you and make you better
- •He says success requires surrounding yourself with great people and building strong teams
- •He says you have to have fun and love what you do every day
Learning from anyone: curiosity, street-level feedback, and pattern recognition
Rubin describes learning from unexpected sources, from arena workers to strangers on the street. Jay connects that curiosity to spotting human behavior patterns, and Rubin explains how pattern recognition informs his decisions, including how he evaluates people and situations.
- •Michael Rubin says he asked arena staff what was working and not working to learn quickly
- •He describes casually questioning strangers about preferences and purchases to understand trends
- •Jay Shetty frames pattern-watching as a powerful skill across domains
- •Rubin says pattern recognition is predictive and central to how he operates
Hiring like a sport: behind-the-scenes diligence and the “quest for incredible talent”
Jay presses on how Rubin hires, and Rubin describes heavy personal involvement in recruiting and evaluating top leaders. He says interviews are only part of the picture, and he relies on calling mutual contacts to understand patterns and reputation, prioritizing leadership, values, and relentlessness.
- •Michael Rubin says he spends 10–20% of his workweek interviewing talent
- •He says he never asks candidates for references and instead contacts shared connections himself
- •He prioritizes subject matter expertise, intellect, leadership, and shared values
- •He looks for long-term builders who are unrelenting and won’t quit
Work-life balance skepticism, routines, workouts, and putting the phone down
Jay asks whether Rubin ever takes a break, and Rubin says he doesn’t relate to traditional work-life balance and won’t apologize for how he’s wired. He shares practical routines he’s building—workouts for mental clarity and intentionally setting his phone down for short periods—while describing constant collaboration with his leaders.
- •Michael Rubin says he doesn’t understand work-life balance and leans into what he loves
- •He shares he’s made workouts more consistent and enjoys hiking for a mental break
- •He says he’s addicted to his phone and practices putting it down for 20–30 minutes
- •He describes a routine of frequent, layered conversations with top leaders to improve the business
Worth beyond money: rejecting net-worth identity and shifting toward impact
Jay asks how Rubin defines his worth, and Rubin says he doesn’t define it that way and declined being featured for net worth recognition. He explains he’s focused on building a better company and making the world better, sharing that his perspective on impact changed after an event in 2017.
- •Michael Rubin says he doesn’t want to be known for net worth but for building a great company
- •He says he views his company with a ‘startup’ mindset, focused on improving what’s weak
- •He says financial results are a scoreboard, but not his core motivation
- •He describes shifting from writing checks to caring deeply about making a difference after 2017
The Reform Alliance: Meek Mill’s case, bold goals, and measurable change
Rubin recounts attending court with Meek Mill and witnessing what he describes as a deeply unsettling sentencing, which catalyzed his involvement in criminal justice reform. He explains founding the Reform Alliance, setting aggressive targets, and measuring results like passing bills and changing probation and parole outcomes.
- •Michael Rubin describes being asked to attend court to see what happens when a Black person goes to court
- •He says Meek Mill received a prison sentence tied to popping a wheelie and it changed Rubin’s perspective
- •He says he was warned not to get involved, but followed instincts and credits support from Jay-Z and Desiree Perez
- •He describes setting a goal of a million people and cites legislative progress and pathways created to reduce probation/parole entrapment
Big audacious goals: aiming for #1 and why “easy goals” lead to failure
Rubin connects impact work and business strategy through the lens of bold goal-setting. He shares Fanatics’ ambition in online sports betting and iGaming, declaring a desire to be number one, and recalls early revenue targets that seemed unrealistic at the time but became milestones that drove progress.
- •Michael Rubin says Fanatics Sportsbook is early and he rejects playing for ‘number three’
- •He publicly states he wants to be number one, even without certainty of achieving it
- •He recounts early bold revenue goals and how they served as targets to work against
- •He argues easy-to-hit goals are effectively choosing to fail and encourages rallying teams around hard goals
Love and family inside an intense work ethic: availability, guilt, and prioritizing moments
Jay asks how Rubin’s business intensity shows up in relationships. Rubin describes a supportive partner, acknowledges he isn’t always available, and explains how his family pushes him to be present; he also shares how he prioritizes critical family moments alongside major business moments.
- •Michael Rubin says his partner is supportive and deeply committed to parenting; he admits he works ‘like an animal’
- •He says he does hear feedback from his partner and older daughter that he isn’t available enough
- •He shares how his daughter reminds him not every call is more important than family
- •He says he’s good at prioritizing and being fully present when it truly matters
Final Five: failure, money, consumer obsession, impact as execution, and one law
Jay closes with rapid-fire questions, and Rubin answers with direct, values-driven responses. He emphasizes not fearing failure, rejects “do it for the money,” highlights consumer focus as his learning edge, and frames impact as measurable work rather than check-writing, ending with a proposed rule about presidential age limits.
- •Michael Rubin says the best entrepreneurship advice is not being afraid to fail, because fear stops action
- •He calls ‘do it for the money’ the worst advice
- •He says he’s working on complete consumer focus in everything they do
- •He defines impact purpose as making real, measurable change and treating it with business discipline
- •He proposes a law: no one can be elected president after age 65

Publisher timestamps

Get more out of YouTube videos.

Read along on your phone, search it beside the video, or ask your favorite AI app what was said.