Boardroom with Rich Kleiman

Omar Raja was a college student when he started an Instagram account to pay tribute to his beloved Miami Heat, and especially his favorite player, Dwyane Wade. That was House of Highlights, the IG account which mastered the creation of viral NBA-related clips, and transformed social media content for a new generation of sports fans. Bleacher Report hired Raja out of University of Central Florida, and acquired House of Highlights. After greatly expanding its content across multiple sports, House of Highlights under Bleacher became the most followed sports social media brand. Raja’s success caught the attention of ESPN, who hired Raja in '20 to run the social accounts for Sports Center, and work as a digital and social talent commentator. In this episode, the 26-year-old talks about catching the entrepreneurial bug from his father, why he started creating content in high school, the tears he shed walking away from House of Highlights, his goals for the future, and much more.

Lawrence Taylor, the NY Giants equally famous and notorious #56, is a Pro Football Hall of Famer, and one of the most dominant and influential athletes in the history of American sports. A fearsome linebacker, he was a defensive superstar of the ‘80s and early '90s whose impact on pro football is still strongly felt. The evolution of the modern Left Tackle (bigger, faster, more agile) was a tactical adaptation developed to help NFL teams protect their QB’s from a Lawrence Taylor pass rush. In this episode, LT talks to Rich and Gianni about winning two Super Bowls with the Giants, why he initially went ballistic when Parcells promoted Bill Belichick as Giants Defensive Coordinator, and his satisfaction in conquering his demons. He also talks about a recent round of golf with Michael Jordan where they debated which QB will win the ’21 Super Bowl, Tom Brady or Patrick Mahomes. 

Jason Koonce is founder and CEO of Detroit-based OTIA Sports, a major player in the sports card and memorabilia industry, with ties to sports legends, including Magic Johnson, Hulk Hogan, and Joe Montana. The self-described “poker degenerate” is also a poker whiz, who once won over a million dollars in a single tournament. In this special episode of Out of Office, Eddie Gonzalez, co-host of the ETCs podcast with Kevin Durant, joins Rich and Gianni in this conversation about Jason’s start in trading cards, and his belief that trading cards have become a serious investment, as potentially valuable a long-term asset as gold or bitcoin.

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:

Instagram

https://www.instagram.com/joshrichards/?hl=en

BFFs podcast with Dave Portnoy and Josh Richards

https://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.