#78: Building Pickletainment and the Business Behind It | Ben Shapiro, PIVOT Agency

#82: How a TALENT REPRESENTATION BUSINESS can Make More Money

If you’re new to my work, I’m Edoardo Grandi and I talk about how wealth is created in sports. I interview the people who build and buy the best businesses in sports, media, and entertainment so you can see how value is created at the highest level.How I got here18: Started speaking with entrepreneurs to understand how sports businesses create wealth.19: Founded Students of Sport Business, an EdTech startup. Engaged 15 elite European sports executives and 150 students. Failed due to funding and adoption.20: Worked in wealth management in Luxembourg and London. Saw how athlete and entertainer services were underserved.21: Joined Berkida Ventures (founded by a 49ers Enterprises advisor) in London. Worked on due diligence and new business with European football clubs and sports tech companies.22: Graduated from John Cabot University in Economics and Finance & Signed NCAA Division 1 at Fordham UniversityToday: Recorded more than 80 interviews with founders and investors in sports media and entertainment to show how the best sports businesses are built, scaled, bought, and valued.My mission is to help Italy produce world champion athletes, make wealth education for athletes and entertainers accessible, and help entrepreneurs succession plan their companies so they transition cleanly. Everything I do is built to help athletes, founders, and creators build wealth in the sports ecosystem.To everyone chasing excellence in sports, keep creating value. I hope this content helps you. The climb is steep, but that is what makes champions.Keep building and never quit,EdoardoDISCLOSURE:Content is educational. Business decisions involve risk. Athletes, founders, and entrepreneurs should evaluate their own strategies and risks. Your results may vary. You are responsible for your own choices.© 2026.

#81: How BLAST Became a Global Leader in Esports Entertainment | Robbie Douek, CEO

How do you build a world class esports media company that produces premium tournaments, global live events, and broadcast experiences watched by millions? In this episode, Edoardo Grandi speaks with Robbie Douek, CEO of BLAST, one of the most influential organizations in modern esports and competitive entertainment.BLAST has become a global leader in tournament production, live event IP, and high end broadcast technology, delivering formats across Counter Strike, Rainbow Six, Fortnite, and multiple publisher partnered ecosystems. Under Robbie’s leadership, BLAST has scaled from a single tournament series into a multi vertical media powerhouse operating in over 150 countries with distribution in 32 languages.Robbie explains how BLAST was built, what problem he saw in the esports events landscape, and why he believes the future of competitive gaming sits at the intersection of media, technology, and live entertainment. We discuss how BLAST structures its business model, how revenue enters the company, and what makes an esports media organization investable in today’s market.We also explore the growth outlook for esports in 2026, including consolidation, new technologies, and the global investment trends shaping the next decade of competitive entertainment. If you work in gaming, esports, or digital media, this conversation will help you understand how a modern events and production company scales internationally and where the next wave of opportunity will emerge.What we coverHow BLAST was founded and the insight behind its global expansionHow the business model works across events, media rights, sponsorships, and IPWhat makes an esports media company investable in 2026How BLAST produces world class tournaments and live entertainment formatsThe biggest tailwinds shaping the gaming and esports industryHow consolidation, AR and XR, and global investment trends will impact events and media companiesThe long term opportunities in global esports production and distributionThe social and community role of esports events for players, fans, and cities🎙️ Guest: Robbie Douek, CEO, BLAST📩 Contact Edoardo: edoardo@sport-businessman.com🌐 Learn business models in sports and entertainment: sport-businessman.com

#80: The Founder Building Italy’s Fastest Growing Esports Organization | Emanuele Acerbis, NOVO Esports

How do you build a modern esports organization in a market that is still early, fragmented, and full of opportunity? In this episode, Edoardo Grandi speaks with Emanuele Acerbis, the co founder and CEO of NOVO Esports, one of Italy’s most ambitious competitive gaming organizations. NOVO was founded in 2023 and is already active across multiple top titles including Brawl Stars, Rocket League, VALORANT, EA SPORTS FC, League of Legends, Call of Duty, Teamfight Tactics, and Street Fighter. The organization has achieved early competitive success, including sweeping major European teams in Brawl Stars and becoming the defending champions of the Italian Rocket Championship. Emanuele explains how NOVO was created, what problem he saw in the Italian esports landscape, and why he believes the next generation of gaming organizations must combine competitive performance, brand building, and community development. We discuss how NOVO structures its business model, how revenue enters the company, and what makes an esports organization investable in today’s market. We also explore the growth outlook for esports in 2026, including consolidation, new technologies, and the opportunities that most people still overlook.If you work in gaming, esports, or digital entertainment, this conversation will help you understand how a modern organization is built from the ground up and where the next decade of growth will come from. What we coverHow NOVO Esports was founded and the early insight behind the company How the business model works and how revenue is generated What makes an esports organization investable in 2026 The competitive structure across NOVO’s titles including Brawl Stars, Rocket League, VALORANT, EA SPORTS FC, and League of Legends The biggest tailwinds shaping the gaming and esports industry How consolidation, AR and XR, and global investment trends will impact organizations The long term opportunities in Italian and European esportsThe social and educational role of gaming for young players, academies, and communities 🎙️ Guest: Emanuele Acerbis, Co Founder and CEO, NOVO Esports 📩 Contact Edoardo: edoardo@sport-businessman.com🌐 Learn business models in sports and entertainment: sport-businessman.com

#79: How AI Is Changing Athlete Financial Decisions | Mayer Reich, Prosperity AI

How do you build AI systems that help athletes make better financial decisions, avoid common money traps, and create long term stability in a career defined by volatility and short earning windows? In this episode, Edoardo Grandi sits down with Mayer Reich, founder and CEO of Prosperity AI and one of the most experienced product builders in fintech and AI. Mayer has spent more than twenty years creating and scaling digital products, co founding four startups and helping them surpass a combined 100 million dollars in revenue. Mayer explains how Prosperity AI is developing financial intelligence tools designed specifically for athletes, including systems that analyze spending behavior, model long term financial outcomes, and translate complex financial concepts into simple, actionable guidance. He also shares lessons from his time as Chief Marketing Officer at Seeking Alpha, where he helped scale the platform to more than 10 million monthly active users. We explore how he built RankAbove, the SEO platform used by Fortune 500 companies, how he approaches go to market strategy for AI products, and why athletes require a different financial intelligence framework than traditional retail users. Mayer breaks down the principles behind Prosperity AI’s product philosophy and how they apply to the next generation of athlete financial tools. If you work with athletes, invest in athlete‑driven businesses, or operate around fintech and AI, this conversation will change how you think about financial education, product design, and the future of athlete financial intelligence. What we cover 1. How Prosperity AI was founded and why athletes need dedicated financial intelligence tools 2. Lessons from scaling Seeking Alpha to more than 10 million monthly active users 3. How AI can help athletes understand spending, risk, and long term planning 4. The story behind RankAbove and what it taught Mayer about enterprise scale product building 5. How to design AI products using a go to market strategy that actually works 6. The future of athlete financial intelligence and where the next opportunities will emerge 🎙️ Guest: Mayer Reich, Founder and CEO of Prosperity AI🌐 Prosperity AI: prosperity.ai📩 Interested in collaborating or appearing on The Sport Businessman Contact Edoardo at edoardo@sport-businessman.com🌐 Learn business models in sports and entertainment: sport-businessman.com

#78: Building Pickletainment and the Business Behind It | Ben Shapiro, PIVOT Agency

How do you turn the fastest growing sport in America into a commercial product that attracts major brands, national sponsors, and mainstream media attention? In this episode, Edoardo Grandi sits down with Ben Shapiro, founder and CEO of PIVOT Agency and one of the most influential commercial operators in pickleball. Ben is the architect behind the sport’s biggest sponsorship deals, the creator of the Celebrity Pickleball Bash, and a former Golden State Warriors executive who brought NBA‑level marketing discipline into a young and fast‑moving sport. Ben explains how the Celebrity Pickleball Bash blends sport and pop culture to reach new audiences, why pairing professional players with celebrities accelerates adoption, and how timing events around major sports weekends maximizes visibility. He also breaks down how PIVOT Agency built the sponsorship strategy for the PPA Tour, bringing in national brands such as DoorDash and Guaranteed Rate and helping establish the financial foundation of the professional circuit. We also explore how pickleball is transitioning from an amateur phenomenon to a commercial media product, what broadcasters are looking for, and how the sport can sustain long term growth through events, storytelling, and brand partnerships. If you own, invest in, or operate around pickleball, this conversation will change how you think about sponsorship, media, and the business architecture behind the sport’s expansion. What we cover 1. How PIVOT Agency became the commercial engine behind professional pickleball 2. The creation of the Celebrity Pickleball Bash and why pickletainment works 3. How major brands evaluate sponsorship opportunities in emerging sports 4. The commercial strategy behind the PPA Tour and its national partners 5. How pickleball is evolving into a broadcast and media product 6. Lessons from the NBA and how they apply to the future of pickleball 🎙️ Guest: Ben Shapiro, Founder and CEO of PIVOT Agency🌐 PIVOT Agency: pivotagency.com 📩 Interested in collaborating or appearing on The Sport Businessman Contact Edoardo at edoardo@sport-businessman.com 🌐 Learn business models in sports and entertainment: sport-businessman.com