Boardroom with Rich Kleiman

How do you build one of the most powerful sports agencies in the world? Mike “Vino” Levine, Head of CAA Sports, joins Rich Kleiman on Boardroom Talks to break down the strategy, leadership philosophy, and business decisions behind CAA Sports’ rise into a global powerhouse. Celebrating 20 years of CAA Sports in 2026, Levine discusses building a 1,400-plus-person global business with 19 lines of business, creating a team-first culture in an industry built around individual agents, and expanding beyond athlete representation into brand consulting, sponsorships, media rights, and sports real estate. He also explains why CAA prioritizes profitability over individual recognition, embracing a philosophy inspired by Barry Sanders. Levine shares how Dwyane Wade helped shape CAA’s approach to athlete entrepreneurship, why the agency is evolving from service provider to investor and business partner, and how the Premier Lacrosse League plans to grow through franchise ownership. He also makes the case for giving professional athletes a pathway to benefit from rising sports franchise valuations, including the possibility of a collective pool of team equity for players.

YG sits down with Boardroom for the latest episode of On Record to break down his evolution from My Krazy Life to his new album, The Gentleman's Club. YG opens up about the experiences that pushed him to confront his past, take accountability, and “kill” the version of himself he built through My Krazy Life. He explains the deeply personal story behind The Gentleman's Club, including why the album took two years to make and how he reverse-engineered its concept around his own life. He also goes deep on the making of My Krazy Life, how he knew the album was a classic, the stories behind hits such as “BPT” and “Really Be,” and how Kendrick Lamar ended up on the latter. YG breaks down his relationship with Jeezy, the strategy behind expanding the West Coast sound beyond California, his musical influences from Eminem, 2Pac, Jay-Z, Biggie, 50 Cent, and Lil Wayne, and why he believes the West Coast can take over again. Plus, YG discusses artistic freedom, his partnership with 10K Projects, the stories behind his most provocative records, and what comes next for YG.

In the latest episode of Boardroom Talks, Michael Che sits down for a wide-ranging conversation about comedy, Saturday Night Live, his new Netflix special Shot in Minnesota, and the changing business of stand-up. Che discusses why great comedy can come from outside the traditional gatekeepers, how social media has changed the path for emerging comedians, and why constraints can actually make artists more creative. He also opens up about his time as SNL's first Black head writer, the challenges of writing from a different perspective, and why criticism can be healthy for the creative process. Che gets candid about his friendship and prank war with Colin Jost, the viral moment when he confronted Ye, the state of Black representation in comedy and television, and why he believes sitcoms have lost some of the magic of the 1990s and early 2000s. He also talks about directing Shot in Minnesota for the first time, why he wanted the special to feel more like a live rock show, the comedians who make him laugh, his love of New York, his favorite music, and the best investment he's ever made: betting on himself and trying comedy.

Keanu Reeves is best known for iconic roles in films like The Matrix and John Wick, but one of his biggest passions away from Hollywood has become a business of its own: ARCH Motorcycle. In the latest episode of Boardroom Talks, Keanu and ARCH co-founder Gard Hollinger sit down with Rich Kleiman for a wide-ranging conversation about the unlikely partnership that became ARCH Motorcycle and ARCH Racing. The two founders trace their story back to 2005, when Keanu brought his Harley-Davidson to Gard’s custom motorcycle shop. What started as a one-off custom bike eventually became a motorcycle company, a racing team, a TV series, and a growing creative brand. Keanu and Gard discuss building ARCH from the ground up, developing their own ARCH 120 LS engine, competing in the MotoAmerica Super Hooligan series, the business behind motorcycle racing, finding sponsors, building a community of owners, and why storytelling has always been central to what they’re creating. Keanu also reflects on what excites him about ARCH, from the creative process and design to racing and the possibility of expanding ARCH into a broader lifestyle brand. He explains why making things has become such an important part of his life, even after decades of making movies.

Emma Grede sits down with Rich Kleiman for the latest Boardroom Cover Story to talk about the ambition, resilience, and relentless work ethic that shaped her path from growing up in London to becoming one of the most influential entrepreneurs in fashion. Grede opens up about growing up around financial stress, starting a paper route as a child, and learning early that money represented freedom. She shares how her mother shaped her mindset, why Oprah became her ultimate role model, and how she turned every opportunity into the next step in her career. She also breaks down the thinking behind Good American, her role as Chief Product Officer at SKIMS, what makes celebrity-backed businesses succeed, why great marketing can't save a bad product, and how the changing media landscape is forcing brands to rethink celebrity and influence. Grede and Kleiman also discuss leadership, empathy, knowing when to change your team, balancing entrepreneurship with motherhood, dealing with criticism and social media, and why reputation can be one of your most valuable assets. From her early days in entertainment marketing to building some of fashion's biggest brands, Grede explains why she's still "just getting going."

For the latest episode of Mental Wealth, entrepreneurs Savannah James and April McDaniel join Boardroom CEO Rich Kleiman and Jack Howard, Head of Money Wellness at Ally Bank, for an honest conversation about money, entrepreneurship, friendship, self-worth, motherhood, and building businesses on their own terms. James and McDaniel open up about how their 15-year friendship evolved into a business partnership, the different ways they approach money, and how their opposite personalities create balance as founders. They also discuss the realities of building businesses while navigating different financial circumstances, why they funded their podcast Everybody's Crazy themselves for its first two years, and how their new holding company, Signed, is helping bring their ventures together. The conversation goes deeper into their personal relationships with money. McDaniel shares how growing up with limited resources created a lingering fear that her money could disappear, while James reflects on understanding her own value despite never having a traditional job or paycheck. Both women discuss the importance of knowing your worth, asking for what you deserve, and doing the inner work necessary to grow. James and McDaniel also explore how they approach money with their children, the values they want to pass down, finding joy in everyday experiences, setting boundaries in business, and learning when to let go of partnerships that no longer feel right.

Mental Wealth explores the financial journeys, mindsets, and lessons of leading figures in sports and entertainment, as well as the emotional relationship we all have with money. Subscribe to Boardroom for more conversations at the intersection of sports, business, culture, and wealth. Visit ally.com/moneyroots to start your mental wealth journey. Ally Bank, Member FDIC.

Master P sits down for the latest episode of Boardroom’s On Record to break down the stories behind No Limit Records, MP Da Last Don, and the moves that helped him build one of hip-hop’s most influential independent empires. He also reveals how he signed Snoop Dogg away from Death Row Records, including the “used car” pitch that led him to pay $1.3 million, and explains why he believed Snoop could become one of the biggest stars and bosses in the world.

Master P also opens up about turning down a $1 million offer from Jimmy Iovine for No Limit, negotiating an unprecedented 85/15 distribution deal, and why ownership and education were central to his business philosophy. Plus, he revisits the making of The Last Don, the album’s movie and marketing strategy, selling more than 100 million records, working with Tupac, Bone Thugs, E-40, UGK, Mia X, Mystikal, and more, his approach to finding artists, writing songs without a pen and pad, and the lessons he wants the next generation to take from his career.

In the latest episode of Boardroom Talks, Tyrese Haliburton sits down with Speedy Morman for an unfiltered conversation about his journey from Wisconsin to the NBA Finals, the 2024 Olympics, his Achilles injury, money, music, fashion, and life off the court. Haliburton opens up about not playing much during the Olympics, using the experience as motivation, the Pacers’ run to the NBA Finals, and what it was like watching the Knicks win it all while sidelined. He also talks about his recovery, his expectations for Indiana’s return, and why he still believes the Pacers can win a championship. Off the court, Haliburton gets candid about his approach to money, including flying Southwest despite signing a $244 million contract, shopping on Facebook Marketplace, hunting for deals on eBay and Grailed, and the $250,000 watch splurge that made him rethink his spending. Plus: becoming a DJ, meeting Jay-Z and Beyoncé, hooping with Floyd Mayweather, his friendship with 50 Cent, getting starstruck by Joe Jonas and Zac Efron, why he hates the words “aura” and “glaze,” and the NBA legends he still wants to meet.

Laremy Tunsil sits down with Boardroom CEO Rich Kleiman for a wide-ranging conversation about leadership, football, business, and building a life beyond the game in the latest episode of Boardroom Talks. The Washington Commanders All-Pro offensive tackle opens up about becoming a better leader, working with Jayden Daniels, his long-running battles with Myles Garrett, protecting the quarterback, and what he learned from a difficult 2024 season in Houston. Tunsil also breaks down his partnership with Lalu Sanni and the evolution of Divine Tree, his approach to investing, building his personal brand, and his YouTube series. He and Rich also discuss the business opportunities and challenges NFL offensive linemen face compared with quarterbacks and skill-position stars.

For the latest episode of Mental Wealth, entrepreneur, DJ, and Summer House star Kyle Cooke joins Boardroom CEO Rich Kleiman and Jack Howard, Head of Money Wellness at Ally Bank, for a candid conversation about entrepreneurship, financial stress, relationships, resilience, and finding joy beyond money. Cooke opens up about the rise and struggles of Loverboy, revealing how the company went from having 30 employees and $10 million in cash to losing money for three straight years and forcing him to financially bail out his own business. He breaks down the costly lessons he learned about hiring, debt, cash flow, and knowing when to ask for help. Cooke also discusses how his upbringing in New Hampshire shaped his relationship with money, why his grandparents became early influences on his entrepreneurial mindset, and the biggest mistakes he made while scaling Loverboy. He shares how the brand's reality-TV exposure, his viral moments, and his DJ career have helped create new opportunities while he works to rebuild the business. The conversation also explores the intersection of money, marriage, mental health, and entrepreneurship, with Cooke reflecting on his divorce, the pressure of being transparent about financial struggles on television, and why pursuing DJing became an unexpected source of passion, income, and freedom.

Ben Shelton sat down with Rich Kleiman for the latest episode of Boardroom Talks ahead of the US Open to discuss his rise to the top of American tennis, his love for playing in New York, and what it takes to compete at a Grand Slam. Shelton opens up about why the US Open is the tournament he wants to win most, how he prepares physically and mentally for the pressure of a Grand Slam, and why he believes the next generation of tennis players is better than ever. The American tennis star also dives into his unconventional path through college tennis at the University of Florida, how college helped develop his game and relationships, and why NIL could change the future of professional tennis. Shelton shares his thoughts on the business of tennis, building an authentic brand, choosing the right sponsorships, and why he prioritizes winning over chasing money. He also breaks down his approach to film study, serving, return of serve, athletic development, mental focus, coaching with his dad, Bryan Shelton, life on the road, and the evolution of tennis from the Big 3 era to today's stars like Carlos Alcaraz and Jannik Sinner.
Subscribe to Boardroom for more conversations at the intersection of sports, business, entertainment, and culture.

For the latest episode of Mental Wealth, Olympic champion Lindsey Vonn joins Boardroom CEO Rich Kleiman and Jack Howard, Head of Money Wellness at Ally Bank, for a candid conversation about resilience, money, identity, and finding purpose beyond the sport that defined her career. Vonn opens up about the physical and emotional toll of her latest injury, the uncertainty surrounding retirement, and why she refuses to let skiing define who she is. She also shares the lessons her parents taught her about money, how she built a career beyond winning races, and why she prioritized long-term partnerships and financial stability over quick paydays. From growing up in a family of five kids and making sacrifices to pursue her Olympic dream to becoming one of the most recognizable athletes in the world, Vonn explains how her mindset around work, money, and success has evolved – and how she's learning to prioritize joy, travel, and life outside of competition.
Mental Wealth explores the financial journeys, mindsets, and lessons of leading figures in sports and entertainment, as well as the emotional relationship we all have with money. Subscribe to Boardroom for more conversations at the intersection of sports, business, culture, and wealth. Visit ally.com/moneyroots to start your mental wealth journey. Ally Bank, Member FDIC.

In a special episode of Boardroom Talks, Kevin Durant sits down with Speedy Morman for an unfiltered conversation. KD opens up about his NBA future, getting older in a young man's league, Russell Westbrook's retirement, LeBron James joining the Philadelphia 76ers, the Knicks' championship run, and why he believes the NBA's global evolution is a good thing. Durant also gets deeply personal, discussing his views on love and dating, his approach to life and introspection, finding purpose, tapping into his "inner Godness," his lifelong competitive mindset, his relationships outside of basketball, gaming, music, money, and much more. Plus, KD explains why he loves talking back to fans, revisits his legendary pregame routine, reveals how he collects jerseys from other NBA players, and reflects on the people who have shaped him along the way.

Nneka Ogwumike is retiring from the WNBA at the conclusion of the 2026 season…on her own terms. In an emotional and wide-ranging Boardroom Talks with Taylor Rooks, the WNBA champion, MVP, 11-time All-Star, and WNBPA President opens up about her decision to step away after 15 seasons, the moment she knew it was time, and what it means to leave the league feeling fulfilled rather than forced out. Nneka reflects on her incredible WNBA career, the evolution of women's basketball, the historic CBA negotiations, her role as a leader and player advocate, and the legacy she hopes to leave behind. She also discusses her next chapter and her desire to keep growing the women's game on a global stage. Plus, Nneka and Taylor discuss leadership, identity, being an introvert, knowing when to move on, and why retirement doesn't have to mean the end — it can mean moving toward what's next.

What does it really mean to be wealthy? In the latest episode of Mental Wealth, Philadelphia 76ers All-Star Jaylen Brown joins Boardroom CEO Rich Kleiman and Jack Howard, Head of Money Wellness at Ally Bank, for an honest conversation about money, success, relationships, and finding purpose beyond a bank account. Brown opens up about being raised by a single mother in Atlanta, how basketball changed his family’s financial circumstances, and what it was like navigating wealth and fame from a young age. He also gets candid about the envy and shifting relationships that can come with success, why money can put you on an island, and the importance of developing “tools of discernment” when managing your finances and the people around you.
Mental Wealth explores the financial journeys, mindsets, and lessons of leading figures in sports and entertainment, as well as the emotional relationship we all have with money. Subscribe to Boardroom for more conversations at the intersection of sports, business, culture, and wealth. Visit ally.com/moneyroots to start your mental wealth journey. Ally Bank, Member FDIC

Emory “Vegas” Jones sits down with Rich Kleiman for a special episode of Boardroom Talks to discuss the journey that made him one of the most influential cultural architects in music, fashion, and sports. From growing up in Cambridge, Maryland, to building alongside Jay-Z, launching Paper Planes, shaping Puma’s cultural resurgence, and developing deep relationships with figures like Nipsey Hussle, Emory reflects on the mindset, patience, and creativity that defined his path.

Kelsey Plum joins Boardroom CEO Rich Kleiman and Jack Howard, Head of Money Wellness at Ally Bank, for an honest conversation about success, money, leadership, and the future of women’s sports. Recorded live during one of the biggest weekends in women’s sports, the first episode of Mental Wealth explores the mindset behind one of basketball’s biggest stars.

Shaquille O’Neal is more than a basketball legend; he’s built one of the most powerful athlete business empires in the world. In this Boardroom Cover Story, Shaq sits down with Rich Kleiman alongside Authentic Brands Group founder and executive chairman Jamie Salter to discuss the mindset behind building a legacy that lasts forever. Shaq opens up about his transition from NBA superstar to entrepreneur, the lessons he learned from Magic Johnson, his partnership with Salter, and why he’s focused on creating businesses that extend far beyond basketball. The two discuss the acquisition and revival of Reebok, Shaq’s vision for the future of the iconic brand, his role as president of Reebok, investing in women’s basketball through Angel Reese, launching the DUNKMAN League, and why the best partnerships are built on trust, honesty, and a shared drive to win. From learning business after entering the NBA to building one of the most recognizable names in sports and entertainment, Shaq explains why he’s still only in the “second inning” of his career.

LeBron James sits down with Rich Kleiman at the Game Plan Summit during Fanatics Fest for a candid interview. LeBron opens up on how he's thinking about free agency and the factors that will ultimately shape which NBA team he chooses next. He reveals how family, like Bronny James, sits at the center of every major decision he makes, both on and off the court. The two dig into his relationship with Jay-Z and how it shaped the way LeBron approaches the game and business alike. He speaks on his long-standing partnership with Maverick Carter, Rich Paul, & Randy Mims. He dives into his relationship with Nike and what that relationship has meant across his career. Throughout the conversation, LeBron gets honest about legacy and how he wants to be remembered when it's all said and done. Presented by Boardroom & CNBC, Gameplan brings together the biggest names at the intersection of sports, business, and culture.

UFC President Dana White sits down with Rich Kleiman in the latest episode of Boardroom Talks for a candid conversation about building one of the most dominant sports empires in history and what's coming next. White breaks down how UFC went from being banned on pay-per-view to selling out 85,000 seats on the South Lawn of the White House, why he believes boxing is fundamentally broken and how he plans to fix it, and the inside story of Power Slap, the sport that outpaced UFC in sponsorship revenue in its first two years.