Zack Weiner is the Co-Founder of Overtime (with Dan Porter), a sports network for the next generation of fans (they currently reach 40m+ of them!). Zack and his team found a gap in the marketplace. Legacy media business were covering pros but not ‘covering their peers’. It was with that insight and the combination of accessible and aspirational that Zack and Dan raised capital (tens of millions worth) and set out to break the mold. It’s a can’t miss episode on the transformation of content, culture and the youth. They started with basketball and have quickly moved into football, soccer and competitive gaming. Did I mention his first day on the job he was 23 years old!

“The lightbulb moment”. I love the sharing from Jason Lake, Founder and CEO of Complexity Gaming about the moment he knew esports could be a real business and he wanted in. And unlike the newcomers, this was 16 years ago! Complexity has won 150+ championships across 30 games and has recently added Dallas Cowboys Owner Jerry Jones as a significant investor. The discussion goes deep on how they are reverse engineering fan engagement (digital first and now into live activation) and how gaming businesses and traditional sports can learn from each other.

Simon Wardle, Octagon’s Chief Strategy Officer, and my go-to on understanding Why Fans Are Fans. I learn something every time I talk to Simon, and this conversation was no different. We jump from the differences between men and women fans to the key attributes of why fans like different sports (sense of belonging, nostalgia, athlete affinity, etc.). I really liked the chapter where we talk about what traditional sports fandom has similar characteristics of an esports fan (I was surprised!).

Mick Batyske (known by his stage name DJ Mick) is an Entrepreneur, DJ and music curator. He has spun for at private parties for Kanye, Lebron, Jay-Z, Will Smith and performed for the First Lady Michelle Obama. In our conversation, we talked about audience, reading them and reacting to what they want. For a DJ, understanding emotional cues define success. He is elaborates on the importance of the physical environment of an event or party. As Inc. calls him, a lively combination of Gary V. and Questlove.

Paige Spiranac is a social media influencer. And those are the words of her audience and brand partners, not just hers. We dig into what that means, how one needs to create content in their own voice and tone, and the challenges (and opportunities) of working with brands. She reads every single comment on her posts and engages. To her, these folks are not followers, they are friends. It’s the ultimate fan engagement.

Dev Sethi is the Head of Sports at Instagram and has spent the past 15 years as a business leader at Google, Youtube, Whistle Sports, and Complex. He shares which athletes and properties are leading the charge and how he is trying to eliminate any friction between fan and talent. We explore how Instagram watches hacks from its own audience to help them innovate and be better. His opening story about personal fandom and Hall of Fame receiver Art Monk was, let’s just say, unexpected.

Paul Rabil, is the co-Founder of the Premier Lacrosse League, was recently listed as SportTechie’s Most Tech-Savvy Athlete of the Year, and has been included in Entrepreneur Magazine’s Top 40 Most Entrepreneurial Athletes list. He is an avid learner and listener. We dig into year one of the PLL – the lessons, the learnings and how to improve in the future. We also explore social media and how he uses different platforms to build his business, grow his brand and commercialize opportunities.

Tony Hawk is a skateboard legend, entrepreneur and in what is maybe his best role: low-income youth community skate park creator. We start by talking about his first experience signing an autograph (he was 12), what it felt like and how that changed over time. We dissect social platforms, how and why he uses them. He shares thoughts on how Seth Rogen inspires him on how he interacts with his fans and also a conversation about how a surprising names helped him learn more about charity and giving. There’s no question the debut of skateboarding at the upcoming 2020 Tokyo Summer Olympics is due in part to his ability to move skateboarding from what was considered “a trend” to a global sport.

John Brody is a WWE executive vice-president and world-class business leader. A fascinating discussion about the speed of business in today’s world which often including changing TV scripts mid-show based on fan response. He has used his past NFL, MLB and the Boston Celtics experience help him deliver on WWE’s three key principles – engagement, authenticity and timing. Make sure to check out Friday Night SmackDown now on FOX.

Zach Leonsis is SVP Strategic Initiatives for Monumental Sports & Entertainment and GM of Monumental Sports Network. Our conversation bounces from the long-term fandom of the Washington Capitals which was optimized during the Stanley Cup championship run to carefully understanding each fan base needs from all the teams they own (Game 1 for their Washington Mystics in the WNBA Finals is Sunday). We spent time on the importance of being transparent with your customers…this was compelling to me. It’s rarely talked about publicly and Zach hits it head on. It’s also a key reason why fans like and appreciate Zach, his father Ted and the Monumental organization.