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Boardroom with Rich Kleiman: Daily Summaries Delivered
by Boardroom Podcast Network
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 is dedicated to bringing impactful conversations from trailblazers across the sports and entertainment landscape. Never-before-heard stories, entrepreneurial advice, and unparalleled access bring you inside the Boardroom universe.
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- Today34 min
E-40 Reveals How T-Pain Created a Hit Hook From Scratch
E-40 joins Boardroom’s On Record to break down the stories behind his legendary career, from the unexpected creation of “Tell Me When to Go” with Lil Jon and Keak da Sneak to how T-Pain made the hook for “U and Dat” from scratch in just 20 minutes. The Bay Area hip-hop icon reflects on the making of My Ghetto Report Card, how the album helped take hyphy worldwide, and why he never claimed to create the movement himself. E-40 also shares how he built an independent career before the streaming era, worked with Cash Money Records in its early days, and helped shape the sound and slang of West Coast rap. Plus, E-40 tells the story behind his diamond-certified collaboration with Big Sean, looks back on his relationship with Kendrick Lamar and the Pop Out, and weighs in on why he thinks too many rappers sound alike today. E-40’s new 40-track quadruple album, Turning My Money Over, is also part of the conversation, as he explains his approach to music, independence, and building a legacy on his own terms.
- 1 weeks ago1h 9m
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.
- 2 weeks ago42 min
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.
- 3 weeks ago51 min
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.
- Oct 12, 202630 min
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.
- Oct 5, 202652 min
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."
- Sep 28, 202638 min
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.
- Sep 24, 202648 min
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.
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About Boardroom with Rich Kleiman
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 is dedicated to bringing impactful conversations from trailblazers across the sports and entertainment landscape. Never-before-heard stories, entrepreneurial advice, and unparalleled access bring you inside the Boardroom universe.
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