Boardroom with Rich Kleiman

When investor and innovator Dan Fleyshman trademarked the phrase "Who's Your Daddy" in high school & turned a merchandise play into an energy drink business that made him the youngest founder of a publicly traded company at age 23, it was just the beginning of his story. On this episode of Out of Office, Fleyshman talks about his investment strategy, his early ventures including the boom and bust of the online poker industry, and what "influencer marketing" meant to him in the pre-social media world. Now, he's leveraged that knowledge as founder of Elevator Studios, managing an army of social media influencers and brand campaigns for large businesses. Fleyshman also reveals what's next in the booming trading cards industry and why he co-founded the trading card shop Cards and Coffee and the social-commerce platform Coffee Breakers with Steve Aoki and DJ Skee, turning the "old school" trading card shop model on its head. 

Restaurateur and nightlife mogul Dave Grutman joins Rich Kleiman to talk about how he built Miami-based Groot Hospitality from the ground up, including the legendary LIV nightclub, and restaurants including Papi Steak, Komodo, & Planta. He talks about his approach to finding partners, how he identifies workers who have the "X factor," why he evaluates employees' potential by how professionally they do the "little things," and how he chooses celebrity collaborators, including his newest partnership with Pharrell. The hospitality guru also gets candid about his early career, including his days as a bartender and what he learned about failure from his ill-fated first nightclub. Plus, his thoughts on New York as a nightlife market, future aspirations in the sports business, and more. 

Curtis Martin, NFL Hall of Famer and former running back for the NY Jets and New England Patriots, shares what still nags him about losing the ’96 Super Bowl; explains why he set aside 12% to 15% of his annual NFL salary for charity; and names both his top five active running backs and the all-time best at the position. Martin also reveals his aspirations to own an NFL team, and much more. 

In this episode, Rich and Gianni have a wide-ranging conversation. Rich shares the story of how his early-career business with music virtuoso, Mark Ronson, prepared him for his current partnership with sports star, Kevin Durant. They discuss their favorite lifestyle brands, rank the top influencers in sports, music and fashion, and explore how Gen Z is currently consuming sports content.

Gary Vaynerchuk, the digital media visionary, angel investor, and CEO of VaynerMedia, talks to Rich and Gianni about why he often values street smarts over Ivy-League degrees in business, the perils of lacking self-awareness, the key lessons he learned as a teen working in his family’s wine business, and the technology he’s confident will revolutionize the consumer experience.

Rich talks to Nick Kyrgios, the ATP Tour tennis pro who’s accomplished the rare feat of beating each of “The Big 3” (Federer, Nadal, and Djokovic). One of the sport’s biggest personalities and most polarizing figures, Kyrgios talks about his obsession with his favorite sport (basketball); what the sport's "old guard" misunderstands about him; and why he’s so impressed with Naomi Osaka. He also reveals how he managed to overcome a serious bout with depression, and why he feels ready to have his best-ever season in 2021.

Rich talks to Brandon Marshall, former NFL Pro Bowl wide receiver, and co-host of Fox Sports One’s studio show, First Things First. Marshall discusses the highs and lows of his NFL career, and why his business, House of Athlete, is focusing on expanding elite athletic training to the general population. He shares his vision for changing the conversation around “mental fitness” so physical and mental wellness are given equal importance on the sports field and in the larger society. Marshall also admits he hasn’t completely ruled out a return to the NFL.

In this episode, Rich talks to Maria Sharapova, a former tennis world #1, and champion of each of the sport’s four Grand Slam events. During her career, she won nearly $40 million in prize money, while also building the foundation for sustainable wealth through savvy endorsement choices, visionary equity deals, and tireless hard work. In 2020, when Forbes Magazine listed the top 10 highest-paid female athletes, nine of them were current tennis pros. This is in part a legacy of the business road map Sharapova paved. But you don’t need to be a tennis pro to benefit from her insights. In 2010, a Harvard Business School course “Maria Sharapova: Marketing a Champion” examined the strategy of “Team Sharapova.” And on this podcast, the former tennis star talks openly about the tough transition to the US after emigrating from Russia as a child, how winning Wimbledon changed the trajectory of her off-court business, and how she evaluates potential brand partners.

In this episode, Rich talks to Michael Vick, the Fox NFL Analyst and former Pro Bowl QB, who largely re-defined the quarterback position…and the perception of what constitutes a franchise NFL QB. They discuss his close relationships with Ravens QB, Lamar Jackson, and Chiefs Head Coach, Andy Reid. They talk about the Atlanta glory days in the early ‘00s when Vick shared center stage in the culture with local hip hop stars, including Outkast, TI, Jeezy and Gucci Mane. Vick shares a candid self-assessment of past mistakes, as well as the hard work he’s put in the last decade to find personal and professional success off the field. He also gives his feedback on Rich’s list of top five NFL QB’s.

In this episode Rich talks to Larry Jackson, Global Creative Director of Apple Music. The self-described “conduit of culture” is one of the music industry’s most influential behind-the-scenes savants. Jackson helped launch Apple's game-changing entertainment service, Apple Music. Along his ground-breaking journey, he’s worked alongside music giants like Clive Davis, Jimmy Iovine and Doctor Dre; championed artist-hosted radio (including L’il Wayne’s Young Money Radio); and produced legendary artists like Whitney Houston and Jennifer Hudson. But perhaps the most unlikely early chapter of Jackson’s story involves him running one of the country’s top radio stations while still in high school. A good friend of Rich’s and a former boss of Gianni's, Jackson is a quintessential Out of Office guest—dropping inspiration, never-before-told music biz anecdotes, and sage business insights.