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)