How Jay Williams Reinvented His Brand After Basketball | The Deal

Intro 0s

• Jay Williams is a multi-hyphenate who was a superstar college athlete, had a massive accident that took him out of the NBA, and reinvented himself to become known from ESPN and as a leading athlete-turned-entrepreneur 1s.
• He is a very good guy with an incredible appetite, is very inquisitive, and is building a big business 23s.
• Jay Williams is considered a fascinating guy with a very intimate and revealing interview, showing vulnerability 31s.
• Jay Williams introduces himself as an on-air personality, owner of a media company, and investor, and expresses excitement for the opportunity to chat 1m2s.
• Jay Williams attended Duke University, played for the Chicago Bulls, and has a connection to Coach K, whom they plan to discuss later 1m16s.
• Jay Williams offers to reintroduce himself, feeling that he should have done a better job of introducing himself, but is told that the initial introduction was good and that people like it a little rough 1m29s.

Expansion 1m38s

• There is a shift happening in sports, media, and culture, allowing athletes to be unapologetically themselves and discuss their portfolios and business ventures openly 1m55s.
• Jay Williams started a holding company called Clandestine Ventures when he first got into TV, but had to keep it private due to ESPN's policies and the negative connotation of investing while working as an analyst 2m9s.
• In the past, athletes and analysts were expected to focus solely on their craft, and discussing business ventures or investments could be seen as a distraction 2m33s.
• Now, athletes and analysts can openly discuss their business ventures and relationships, such as Jay Williams' connection with Adam Silver and his insight into team ownership and the CBA 2m48s.
• The shift is also attributed to the extension of bandwidth, allowing for more nuanced and colorful commentary beyond just polarizing conversations or game analysis 2m59s.
• Jay Williams was on the front end of this shift, seeking advice from owners and exploring business ventures beyond his core business as an athlete 3m16s.
• In the past, athletes had to keep their business ventures private, with some even facing backlash for pursuing interests outside of their core business 3m26s.
• The contrast between the reaction to Jay Williams' contract in 2001 and Shohei Ohtani's business ventures is notable, with Ohtani being celebrated and Williams being villainized 3m48s.
• Social media has given athletes more power and a platform to share their thoughts and business ventures, contributing to the shift in the sports and media landscape 4m1s.
• 25 years ago, owners had more control, but now athletes have more agency and can use their platforms to share their interests and business ventures 4m8s.

From Asset To Principal 4m10s

• A gap exists for athletes and celebrities transitioning from being assets to becoming principals, and navigating this shift while maintaining neutrality is crucial 4m20s.
• Focusing on long-term goals helps in making this transition, as opposed to being transactional and seeking immediate results 4m43s.
• A key mistake young players make is being too focused on short-term gains, likely due to their experience in basketball where contracts can be secured quickly 4m45s.
• Building a business over 50 or 60 years requires discipline and a different approach than what is typically seen in basketball 4m57s.
• The "10-touch rule" is a strategy used to build relationships before considering partnerships, which involves having at least 10 interactions, such as emails or meetings, before collaborating 5m0s.
• This approach helps to establish a transformative relationship rather than a transactional one, allowing for more meaningful connections and collaborations 5m27s.
• Many athletes in the industry prioritize instant cash grabs over long-term brand strategies, which can be detrimental to their overall success 5m37s.
• Having a clear long-term plan is essential for athletes looking to transition from being assets to becoming principals and building a sustainable brand 5m41s.

Becoming A Business Man 5m44s

• Jay Williams' interest in business started at a young age, influenced by his parents, with his dad working at American Express for over 20 years and his mom being a guidance counselor who pursued multiple master's degrees while he was in school 5m52s.
• His dad would often take him to the city, where he would see him prepare for work, including tying his Windsor knot, teaching him to prepare for the job he wanted, not the one he had 6m15s.
• Jay Williams was also inspired by Ken Chenault, the first Black CEO he had ever seen, who was the CEO of American Express at the time 6m23s.
• During his time at Duke, Coach K encouraged him to think like a businessman, and they would invite Fortune 500 executives who had graduated from Duke to share their experiences and insights 6m49s.
• These interactions helped Jay Williams understand how to utilize his name, image, and likeness, and how to approach the NBA 7m21s.
• He started crystallizing the idea of a holding company during his sophomore year at Duke, after losing in the Sweet 16 and deciding to focus on his education and basketball 7m49s.
• Jay Williams' education on finance and business came from his parents, agents, financial advisors, and accounting services, who helped him set up a limited liability corporation (LLC) and navigate the business side of his career 8m58s.
• He initially found the onboarding process overwhelming, but it eventually became part of his routine, and he saw it as a complement to his work on the court 9m27s.
• Jay Williams made a point to allocate a portion of his earnings towards real estate investments, aiming to buy a million dollars' worth of real estate for every $200,000 he made 10m3s.

Role models 10m16s

• Magic Johnson is a role model who created the foundation for his company nearly 30 years ago, and his success in real estate is particularly inspiring 10m24s.
• Michael Jordan is another role model, and his entry point into business was through his agent David Falk, who helped him build the Jordan brand 10m53s.
• Growing up, he admired Magic Johnson so much that he wore the number 32 in high school, but had to change to 22 in college because the number was already taken 10m38s.
• He also looked up to Grant Hill, who played at Duke and is a part-owner of the Atlanta Hawks, and tried to learn from his business experiences 12m35s.
• His career was cut short after one year, which meant he didn't have the chance to develop relationships with his role models as much as he would have liked at an earlier stage 12m50s.
• He had to navigate the challenges of having family members involved in his business, including his father as CFO and mother as CMO, and figuring out how to delegate responsibilities and take ownership 11m46s.
• He had conversations with Magic Johnson about how to take more ownership of his business and delegate responsibilities to his family members 12m1s.
• He struggled with vetting deals and people, and didn't have practical experience in business, which made it difficult to navigate the industry 12m28s.

Getting Onboarded to Wealth 13m2s

• Jay Williams grew up with a single mom after his dad left when he was 10 years old, which significantly impacted his life 13m8s.
• His mom worked two jobs, as a secretary in the morning and serving tables at night, and they relied on government assistance, including food stamps, at times 13m12s.
• Jay felt the need to be the leader of his family and take on an alpha role from a young age 13m36s.
• He notes that his Dominican mom would always be in charge, regardless of any title he might give her 13m43s.
• Jay's friends from more successful families had more financial conversations with their parents, which gave them a higher level of competency in managing wealth 14m0s.
• Jay was thrust into a lifestyle with the rich and famous but didn't learn about the underlying business of sustaining wealth 14m9s.
• He and others were essentially given a crash course in managing wealth, which he refers to as being "onboarded to wealth" 14m21s.
• As Jay's parents and career began to build, he found that making money revealed more challenges and difficulties, often referred to as "more money, more problems" 14m31s.
• Family dynamics started to play a role in business, raising interesting questions about the intersection of family and wealth 14m43s.

Brand Building & Financial Competency 14m45s

• The college sports world has undergone significant changes due to the introduction of name, image, and likeness (NIL) policies, allowing athletes to earn money from their brand and image 14m49s.
• Athletes like Jalen Milroe are making over a million dollars a year in NIL, and it's essential for them to understand finance and business concepts, such as LLCs, at a young age 15m51s.
• To manage their finances effectively, athletes should create a "flat line" to understand their business and prioritize their main goals, allocating time and attention accordingly 16m32s.
• Reading, asking questions, and having curiosity are essential for putting in the work and achieving success, whether it's becoming a billionaire or transitioning from an asset to a principal 16m50s.
• Owning one's intellectual property (IP) is crucial, as seen in the case of Jalen Milroe and his teammate Terrion Arnold, who started the "Let A Naysayer Know" (LANK) movement and filed for trademark, leading to a merchandising deal with the school 17m0s.
• Athletes should navigate owning a name or brand while dealing with their school and competing at a high level, and creating a digital diary series can help them share their experiences and build their personal brand 17m42s.
• Aligning one's narrative with the school's goals while showcasing individual leadership and personality is essential, and partnering with brands like Beast can help athletes build their personal brand and endorsement deals 18m19s.
• Working with collectives, schools, and brands requires a strategic approach to building an individual brand, and athletes should prioritize personal engagement and content creation to achieve their goals 18m37s.

Becoming a Trusted Advisor 18m40s

• Building a rapport with someone like Anthony Edwards to become a trusted advisor involves a Big Brother approach, where guidance and advice are offered in a supportive manner 18m56s.
• This approach includes providing feedback on how to handle media interactions, such as suggesting alternative ways to phrase answers to put him in a better position 19m3s.
• It also involves explaining complex concepts, like the nuances of a deal, in a way that is easy to understand when he is frustrated or unsure 19m15s.
• The relationship is built on helping him navigate various aspects of his career and personal life, rather than acting as his agent or financial advisor 19m19s.
• The role is more of a partner, working with him on the media and brand side of his career 19m30s.

NIL Better for College Sports? 19m33s

• The current state of college sports with Name, Image, and Likeness (NIL) deals is described as the "Wild Wild West," and it's unlikely to change back to the way it was before 19m33s.
• NIL deals are better for college sports, but there's a need to differentiate between NIL and revenue sharing, where athletes are actual partners and employees of the school or team 19m50s.
• Revenue sharing is a different conversation that involves discussing workers' compensation and other employee benefits 20m7s.
• The difference between NIL and revenue sharing is that NIL involves athletes getting paid by brands or companies, while revenue sharing makes athletes partners and employees of the school or team 20m15s.
• Some colleges, like Dartmouth basketball, are already exploring revenue sharing models 20m32s.
• The recent move of USC and UCLA to the Big 10 conference is driven by financial interests rather than geographical or academic considerations 20m40s.
• This shift in priorities raises concerns about the impact on student-athletes, including their travel schedules and academic responsibilities 20m50s.
• With the increasing commercialization of college sports, there's a need for players to have representation and protection, potentially through unionization 21m25s.
• Unionization would grant players employee rights and benefits, which is seen as the next step in the evolution of college sports, particularly in revenue-generating sports like basketball and football 21m30s.
• The disintegration of the Pac-12 conference serves as an example of the changing landscape of college sports 21m44s.

Jay’s Vision 21m53s

• The vision for media is constantly evolving, requiring frequent adjustments and adaptations to new shapes and forms. 22m6s
• Initially, the focus was on capturing the value in production and creative aspects of endorsements for major athletes like Giannis, who has a global presence across Africa, the United States, and Europe. 22m23s
• The approach involves integrating into the storytelling aspect of endorsements to build long-term sustainability with clients, rather than treating them as short-term financial opportunities. 22m48s
• The strategy includes sitting at the creative table, maintaining metrics and data, and demonstrating added value to the client's brand, which can lead to investment opportunities and co-investment with athletes. 23m12s
• The model is inspired by Ryan Reynolds' Maximum Effort, which successfully scaled brands like Aviation Gin and Mint Mobile, emphasizing the importance of both brand amplification and capital deployment. 23m38s
• There is a focus on creating shared economic opportunities for athletes, similar to what Stephen Curry and LeBron James are doing, by pooling resources and adding collective value. 24m0s
• The concept envisions a multifamily office where multiple athletes collaborate, pool capital, and co-invest, bringing brand strategy and vision to the table to create enterprise value and compound interest over time. 24m30s

The Big Pivot 25m4s

• A pivotal moment in life occurred when a terrible accident happened right as entering the league, changing the entire direction and business career, forcing a hard pivot 25m11s.
• The accident gave a crash course in how hard and cold business could be, making it difficult not to become emotionally tied to being the asset in a deal 25m46s.
• Watching the Bulls draft Kirk Hinrich to replace the injured player was a hard pill to swallow, leading to conversations with Jerry Reinsdorf and understanding the business strategy 26m15s.
• The experience led to a deep state of depression, with two attempts at suicide, but eventually forced a start over again, leading to a desire to understand basketball and the Collective Bargaining Agreement (CBA) 26m50s.
• The accident and subsequent depression led to a path of risk mitigation, including receiving bills for 13 plus surgeries and understanding how to pay for them, with the Bulls keeping the player on their insurance 27m14s.
• The experience opened eyes to risk mitigation and led to a big investment in an insurance brokerage firm, understanding wholesale and the middleman aspect 27m33s.
• Studying the CBA under Charlie Grantham led to an attempt to become an agent, but things became difficult due to the complexities of working for an agency and the rules surrounding AAU programs 27m52s.
• A news reporter broke a story on Yahoo Sports about the agency paying Kevin Love's AAU team, making it difficult to connect with players and leading to a change in narrative 28m18s.
• Getting involved in TV helped to understand how media works and led to the process of writing a book to change the narrative 28m50s.

Starting Over 29m5s

• Jay Williams decided to stop viewing himself as a victim of his motorcycle accident and instead use the experience to build his business career, starting with crisis management and media work at ESPN, earning $35,000 a year. 29m7s
• He began to understand the media industry and started writing a book as part of his reinvention process. 29m31s
• The discussion highlights the challenges of rebuilding a career from scratch, drawing parallels between Jay Williams and another individual who faced a similar situation after a suspension. 30m3s
• Both individuals shared a competitive nature that drove them to continue pursuing new opportunities rather than withdrawing from public life. 31m2s
• The motivation to return and make an impact was partly driven by the desire to offer guidance to young people who lack strong mentors, using personal experiences as lessons. 31m57s
• The focus was not on returning to previous glories, such as playing professional sports again, but on exploring new chapters and making a meaningful contribution. 32m13s
• Jay Williams had to learn to redefine his identity beyond his past achievements as a high-profile athlete, which included being a top draft pick and playing for the Chicago Bulls. 32m29s
• The approach to business meetings involved starting with the worst aspects of one's story to set a foundation for improvement and demonstrate self-awareness. 32m40s
• By leading with the worst parts of a story, it allows for a more honest and efficient meeting, potentially saving time if the meeting is not going to be productive. 32m57s
• Owning past mistakes and discussing lessons learned can help establish a sense of self-awareness, which is often lacking in individuals who have achieved significant success early in their careers. 33m15s
• Success, such as winning a championship or signing a big contract, can lead to decreased self-awareness and increased ego. 33m32s
• A daily practice involves praying to enhance self-awareness and decrease ego, which is considered a personal "happy spot." 33m44s

Everybody’s Had A Crash 33m55s

• Many people, including C-level executives, have faced significant challenges in their businesses, such as filing for bankruptcy or losing money for investors 34m1s.
• The realization that everyone has experienced some kind of crash or setback, whether public or private, can serve as a foundation for building connections with others 34m21s.
• Recognizing the universality of setbacks can help individuals approach relationships with more self-awareness and less ego, allowing for the formation of stronger communities 34m37s.
• Building from this realization involves creating a sense of connection and understanding with others who have experienced similar challenges 34m41s.
• The idea of shared experiences and setbacks can be a powerful tool for building bridges and fostering a sense of community 34m28s.

Building 34m42s

• Building a personal brand requires figuring out who you are, what you do, and what you contribute, as well as defining your mission, 34m52s
• To hone this mission over time, it can be helpful to have a board of advisors, such as a personal board, which can provide guidance and support, 35m22s
• A personal board can be made up of people you admire and respect, such as Coach K, who can offer valuable insights and feedback, 35m18s
• Having a personal board can be like having a real board meeting, where you discuss your progress, goals, and challenges, and receive constructive criticism, 35m33s
• In addition to discussing professional goals, a personal board can also help with personal issues, such as balancing marriage and family life, 35m45s
• Leaning into media can be a way to build a platform and establish a personal brand, by learning how to be effective and different in the media space, 36m3s
• Studying media and how to be effective at it can help you develop a unique voice and style, and stand out from others in the industry, 36m13s

Reaching out 36m22s

• There is a significant gap between the sports and entertainment communities and the business community, and reaching out to great people is the best way to grow a business 36m23s.
• Having an insatiable appetite and being willing to learn and take risks is essential for growth and success 36m43s.
• Understanding the business side of sports, including what teams are coming onto the market and the growth of various leagues, is crucial for making informed investment decisions 36m48s.
• Vetting opportunities and understanding the dynamics of different leagues and teams is essential for success in the sports business world 37m14s.
• Learning from others, such as LeBron James and Maverick Carter, and understanding how they built their media empire and utilized it for investments, can be highly beneficial 37m25s.
• Working with others, such as Rich Kleiman and Kevin Durant, and launching projects like "The Boardroom" can provide valuable experience and opportunities for growth 38m5s.
• Having conversations with high-level executives and athletes, such as Jimmy Pitaro, Connor Schell, Serena Williams, Steve Ballmer, and Josh Kroenke, can provide valuable insights and knowledge 38m14s.
• Athletes who want to succeed in business should be willing to take risks, sit at the table, and be uncomfortable, and it's essential to be alone in the room to truly learn and grow 39m23s.
• Getting in the room and being willing to take risks is crucial for athletes who want to succeed in business, and having the "moxie" to do so is essential 39m47s.

Future of Jay Williams Holding Company 40m0s

• The Jay Williams holding company aims to have capital to deploy in order to have a seat at the table in various business ventures 40m18s.
• Williams plans to maintain a presence in the media industry from an ownership perspective, as he understands the business and its future direction 40m29s.
• He finds the sports marketplace fascinating and wants to have capital behind an entity with a media marketing branding arm to invest in and scale certain assets 40m41s.
• Williams envisions a team of brand strategists and a chief investment officer to look at different assets and marry intellectual property to certain athletes who want to work and have a seat at the table 41m12s.
• He sees a correlation between having conversations with individuals he believes in and being able to provide them with opportunities to work and have a seat at the table 41m28s.
• In five years, Williams hopes to own a significant piece of prominent college sports teams, such as Duke basketball or Ohio State football 41m49s.
• He believes the collegiate market will be influenced by private equity firms and sees an opportunity to help athletic departments like Duke generate more revenue and be more profitable 42m23s.
• Williams aims to provide insightful commentary and tell stories from the player/businessman perspective, which he believes could be his sweet spot in the industry 42m52s.
• He is learning to balance being true to himself and his opinions while maintaining relationships in the industry 43m3s.

Follow Up 43m16s

• Getting into the room and having a meeting is just the first step, as it's relatively easy for a journalist or an everyday person to get in, but it's what happens after that is crucial, and being able to prove oneself and start a relationship is key 43m16s.
• Many people, including athletes, expect to just meet, take a picture, sign autographs, and then leave, but having a real team and following up is not typically expected 43m49s.
• Most athletes, about 20%, ask for a meeting, but only about 1% of those athletes follow up in a meaningful way, which is a crucial step in building relationships and achieving success 44m4s.
• Athletes need to have a long-term perspective and be persistent, as most meetings do not lead to immediate success, unless you are someone like Tiger Woods or Tom Brady 44m14s.
• It's the athletes who are willing to hang around, keep coming back, and stay focused on their goals who are more likely to achieve success 44m27s.

Rapid Fire 44m35s

• The rules for the rapid-fire segment are to keep the answers tight, with no chance to ask questions back initially, but possibly at the end 44m44s.
• Jay Williams describes his deal-making style in one word as "patient" 44m51s.
• When it comes to deal-making, Jay Williams values data but ultimately relies on his instincts and gut feeling about people 44m56s.
• Jay Williams' dream deal-making partner is David Rubenstein 45m6s.
• The best piece of advice Jay Williams has received on deal-making or business is to "never run, always walk with pace" 45m15s.
• The worst advice Jay Williams has ever been given is to do as many deals as possible, which came from a successful athlete 45m29s.
• Jay Williams' hype song before a big meeting or negotiation is classical orchestra music, which helps him stay calm and take the emotion out of the deal 45m37s.
• Jay Williams also enjoys the music of Patti LaBelle 45m53s.
• A fun fact about Jay Williams that his colleagues might be surprised to hear is that loyalty and transparency are very important to him due to his past experiences of being misled by others 45m56s.

Outro 46m18s

• Jay Williams was thanked multiple times for his participation, with appreciation expressed for the conversation. 46m20s
• The thanks were repeated several times, with slight variations in wording, to emphasize gratitude. 46m22s
• The conversation concluded on a positive note, with a final expression of thanks to Jay Williams. 46m25s