Josh Richards is an 18-year-old digital media entrepreneur, angel investor and social media personality, with over 25M followers across platforms. He’s also Chief Strategy Officer for Triller, the video and social media app company, and competitor with TikTok. In just a few years, Richards has co-founded digital talent management firm TalentX, co-founded Ani Energy, an energy drink business, and signed a record deal with Warner Records. He also co-hosts the podcast, BFFs, with Dave Portnoy, the founder of Barstool Sports. In this episode, the Canadian teen talks to Rich and Gianni about his early attraction to business; squashing beefs between the content creator camps, Sway House and Hype House; his admiration for Mark Wahlberg; and his aspirations for growing his business, both as an entrepreneur and entertainer. You can find Josh at: Instagramhttps://www.instagram.com/joshrichards/?hl=en BFFs podcast with Dave Portnoy and Josh Richardshttps://www.youtube.com/channel/UCJRz6HSllkQKmFxaPk8IViw

Jason Strauss is a co-founder and co-owner of the Tao Group, the world-renowned luxury hospitality company best known for its restaurant/nightclub brands: Tao, Lavo, Marquee and Avenue. Strauss talks to Rich (they've been friends since high school) about launching a nightlife business with long-time business partner, Noah Tepperberg. In 2003, the duo launched Marquee, the Manhattan restaurant/nightclub famous for its endless stream of celebrities and world-class hospitality. The club's success became the subject of a 2009 Harvard Business School case study, and led the duo to expand to Las Vegas where they opened Tao at the Venetian hotel, one of the country's highest-grossing restaurants and nightclubs. In 2017, the Madison Square Garden Company acquired a majority stake in Tao Group. Strauss talks about staying relevant in a youth-driven industry, his bullish expectations for post-covid nightlife, and the MSG Sphere, his group's upcoming music and entertainment arena in Vegas, one he believes will set a new bar for the nightlife experience. 

Brian Koppelman is the co-creator, showrunner and Executive Producer of Billions, Showtime’s acclaimed dramatic series exploring the high-stakes, cut-throat world of a hedge fund tycoon and the prosecutor trying to take him down. He also hosts the podcast, The Moment with Brian Koppelman. A Long Island, New York native, Koppelman followed his father’s footsteps into the music business, playing pivotal roles in the recording careers of both Eddie Murphy and Tracy Chapman, the multi-platinum and multi-grammy-winning artist. Koppelman ultimately stepped away from a successful career as a music industry A & R exec, to pursue his passion of being a writer. A self-described “poker degenerate,” Koppelman and his writing partner, David Levien, immersed themselves in underground poker clubs, the setting which inspired Rounders, the ’98 poker-themed film starring Matt Damon and Edward Norton. Koppelman shares with Rich and Gianni how he’s been able to maintain his child-like enthusiasm for his work, and tips his hand on the future of the hit series, Billions. 

Los Angeles Lakers point guard, Quinn Cook, has had a fascinating career. Coming out of high school as a McDonalds All-American, he led the Blue Devils to a national championship in college, then shockingly went undrafted coming out of Duke. But after years battling in the G League to get to the NBA, he’s made the most of it, garnering two championship rings, and now a new deal with the Lakers. Cook’s story has been defined by his resilience, charisma, work ethic, and a commitment to learning from prized mentors, starting with his entrepreneurial parents. Cook also credits Kevin Durant, Coach Krzyzewski, LeBron James, and, our host, Rich Kleiman for providing support, guidance and tough love during his journey. Taking nothing for granted, the 27-year-old has developed a veteran’s wisdom about building his business network and entrepreneurial skillset while he’s still in the NBA. 

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.