Boardroom with Rich Kleiman

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.