Boardroom with Rich Kleiman

By Boardroom Podcast NetworkSports Business Entrepreneurship

Favorites
36
Followers
Typical duration
43 min
per episode

Based on Podcast App listening data

Boardroom with Rich Kleiman episodes

November 02 How Barry Sanders Inspired the Culture Behind CAA Sports
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.
1 hr 10 min
October 27 What Kendrick Lamar Heard That Made Him Want To Be on YG’s “Really Be”
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.
43 min
October 19 Cancel Culture Is Good for Comedy? Michael Che Thinks So
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.
52 min
October 12 Keanu Reeves on Building ARCH Motorcycles, Racing, & Life Beyond The Matrix
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.
31 min
October 05 Emma Grede on Building SKIMS, Good American, & a Billion-Dollar Business
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."
53 min
September 28 How Savannah James & April McDaniel Balance Friendship, Money, Entrepreneurship
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.
39 min
September 24 Master P Called Snoop Dogg A Used Car Before Signing Him For $1 Million
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.

49 min
September 21 Tyrese Haliburton on Why Kevin Durant, LeBron James, & Steph Curry’s Respect Matters Most
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.
51 min
September 17 Laremy Tunsil On Why Jayden Daniels Is Already A Top 5 NFL QB
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.
23 min
September 14 Kyle Cooke on Saving Loverboy & Finding Financial Freedom
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.
25 min

About Boardroom with Rich Kleiman

From the publisher's feed

Boardroom with Rich Kleiman brings fans inside the careers and conversations of some of the world's most fascinating thought leaders, including entrepreneurs, athletes, and entertainers. The show…