Boardroom with Rich Kleiman

Jaksot

• 
  Kyle Cooke on Saving Loverboy & Finding Financial Freedom 14.09.2026 24min

  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 Wants to Win the US Open More Than Anything 03.09.2026 45min

  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.
• 
  Lindsey Vonn On Why Winning Must Come Before Money 31.08.2026 38min

  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.
• 
  Kevin Durant On LeBron's 76ers Move, the Knicks Ring, Westbrook Retiring, & His NBA Future 27.08.2026 1t 7min

  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 Reveals Why She Is Retiring From The WNBA 19.08.2026 49min

  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.
• 
  Jaylen Brown Opens Up on How NBA Wealth Changed His Life & Relationships 17.08.2026 48min

  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 Jones on Jay-Z, Paper Planes, Roc Nation, & Building Culture 14.08.2026 32min

  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 Gets Real About Money, Success, & the Future of Women's Hoops 11.08.2026 30min

  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 & Jamie Salter on DUNKMAN, Acquiring Reebok, and the Shaq Brand 11.08.2026 34min

  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 Opens Up on Why He Chose Philly, Jay-Z, Bronny & NBA Legacy 04.08.2026 27min

  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.
• 
  Dana White Breaks Down Everything: UFC, White House Fight Night, Power Slap & Disrupting Boxing 20.05.2026 41min

  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.
• 
  How David Grutman Built LIV, Komodo, & Papi Steak Into a Global Empire 11.05.2026 22min

  For Boardroom’s latest Cover Story, Groot Hospitality founder David Grutman breaks down the mindset behind LIV, Komodo, Papi Steak, Gekkō, Casadonna, and the relationships that helped turn Miami into a global hospitality capital. From building long-term trust with talent and entrepreneurs to teaching a college course at FIU that inspired his new book Take It Personal, Grutman explains why caring deeply has become his competitive advantage.
• 
  Steve Stoute On Kim Kardashian, Beyoncé, Brent Faiyaz, Hailey Bieber, & More 08.05.2026 40min

  In this special edition of Boardroom Talks, Steve Stoute continues his wide-ranging conversation with Rich Kleiman on culture, music, and the new rules of influence in business. From the cultural impact of Kim Kardashian and SKIMS, Beyoncé’s blueprint for ownership and artistry, Rihanna’s empire with Fenty, and Hailey Bieber redefining beauty with Rhode, to Brent Faiyaz’s rise as a “pure artist” operating outside the traditional machine, the conversation explores how today’s biggest names are reshaping what power looks like in entertainment and branding. Stoute and Kleiman also break down the evolving financial model of music streaming, why major labels are starting to function more like indie operations, and how the role of a great CMO has shifted from marketing products to building culture itself.
• 
  Steve Stoute Sounds Off On Stephen A. Smith, Drake, Jay-Z & Why Fame Is Winning 08.05.2026 21min

  Steve Stoute – aka “The Commissioner”-- joins Rich Kleiman for the newest episode of Boardroom Talks for a raw, unfiltered conversation on culture, music, and the rise of fame over talent. From getting his nickname from Nas to advising icons like Jay-Z and Jimmy Iovine, Stoute breaks down how hip-hop reshaped business, and where things are headed next. He explains why “fame doesn’t need talent anymore,” and how that shift is changing everything from music to media to personal branding.
• 
  Livvy Dunne Reveals How She's Building Her Business Empire 10.04.2026 18min

  Livvy Dunne opens up like never before in this raw, in-depth conversation for Boardroom’s April Cover Story about her rise from a relentless young gymnast in New Jersey to one of the most influential college athletes in America. From training in her childhood living room with “no off switch” to competing for LSU and helping deliver a national championship, Dunne breaks down the sacrifice, discipline, and obsession that shaped her path. She also reveals how she turned NIL into a personal empire – building massive social media influence, landing major equity deals, and redefining what it means to be a modern athlete. In this interview, she discusses everything from early Olympic dreams and devastating injuries to her first acting auditions (including a surprising White Lotus moment), and why she believes female student-athletes can build careers far beyond their sport. Tap in to learn Livvy’s story of ambition, identity, and what happens when talent meets relentless focus.
• 
  For Mark Jackson, Christmas Day at Madison Square Garden Still Hits Different 24.12.2025 19min

  Mark Jackson sits down with Rich Kleiman to reflect on the history and spotlight of NBA games on Christmas as a player, a coach, and a fan in a very special conversation, presented by State Farm®. Jackson discusses the commitment it takes as a player to weather the holidays and the sacrifice everyone on the business side makes in forgoing family for hoops on Christmas Day. He explains why Patrick Ewing stands alone as the greatest Knick of all time, breaking down leadership, toughness, and what Ewing represented to New York basketball. Jackson also revisits his time coaching the Golden State Warriors, including insights into Stephen Curry’s growth, mindset, and what made those Warriors teams special. He opens up about Rick Pitino and why he remains the most influential and respected coach of his career. Throughout the interview, Jackson connects eras of the game, blending history with the modern evolution of basketball. He offers a candid, legacy-driven look at basketball through the eyes of someone who has lived it as a player, coach, and voice of the sport.
• 
  Andrew Ross Sorkin on Oprah, Elon Musk, AI, and the Next Big Stock Market Crash 29.11.2025 43min

  Andrew Ross Sorkin has spent his career following the money to understand everything — from Wall Street to Silicon Valley, from media to AI. A journalist who never set out to be one, Sorkin built DealBook into the Super Bowl of business journalism, turning curiosity into empire-building. In Boardroom's October Cover Story, he shares how an overheard word such as “internet” landed him at The New York Times, how he approaches interviews like a tennis rally rather than a serve, and why Oprah remains his white whale. Through stories of Too Big to Fail, the 1929 crash, and the coming AI reckoning, Sorkin unpacks how narrative drives markets, crashes, and comebacks alike. From Elon Musk’s many personas to the billion-dollar game of sports, streaming, and live entertainment, this is Andrew Ross Sorkin: journalist, storyteller, dealmaker — chasing what feels impossible, one conversation at a time.
• 
  Eugene Remm on Scaling the Right Way: 'You Can’t Fake Hospitality' 13.11.2025 23min

  Eugene Remm, co-founder of Catch Hospitality Group, joins Rich Kleiman on Boardroom Talks to share how he built one of the most recognizable restaurant brands in the world without losing authenticity or the soul that made it special. From his early days as a nightlife promoter in New York to creating a global hospitality empire, Remm discusses the lessons learned along the way, from scaling culture and consistency to building teams based on trust and communication. He also opens up about leadership, patience in business, and why true hospitality is something you can’t fake. Watch as Remm breaks down what it really takes to grow a brand that connects across food, culture, and experience, and how he’s continued to evolve Catch without compromising what makes it unique.
• 
  AJ Dybantsa Is the Next NBA Phenom 08.11.2025 14min

  A consensus five-star recruit coming out of high school, AJ Dybantsa shocked the basketball world when he turned down powerhouse programs to take his talents to BYU. In the latest episode of Boardroom Talks, Dybantsa sits down with Rich Kleiman to reveal why he chose the Cougars, what makes playing for Kevin Young special, and why he’s looking forward to March Madness more than the NBA. The two also discuss who Dybantsa models his game after, including Kevin Durant, the best business advice he’s gotten from LeBron James, incoming Mavericks rookie Cooper Flagg, his expanding NIL portfolio that includes deals with Fanatics and Red Bull, and much more in this exclusive interview.
• 
  US Open Champion Aryna Sabalenka Is Defending Her Title 03.09.2025 24min

  Reigning US Open champion and world No. 1 Aryna Sabalenka reflects on her breakout year in an exclusive Boardroom Cover Story interview with co-founder Rich Kleiman. Following her first Grand Slam win last September, Sabalenka has emerged as one of the most dominant and recognizable figures in tennis, and she opens up about the pressure of defending her US Open title, the emotional rollercoaster of elite competition, and the personal growth that comes with life at the top. She discusses the challenges of winning over American crowds during high-stakes matches like her victory against Jessica Pegula, the intense discipline required to maintain her No. 1 ranking, and the career-defining move of switching from IMG to Naomi Osaka’s agency, Evolve. Sabalenka also dives into the off-court aspects of her rising stardom, from expanded branding opportunities to how idols like Novak Djokovic and Rafael Nadal helped shape her mindset and ambitions. She shares her goals for the future—both on the court and in life—as she aims to build a lasting legacy in women’s tennis while hoping to one day balance starting a family with continuing to compete at the sport’s highest level.