In this episode of The Long Game, we sit down with Mathieu Massa, the founder behind some of Miami’s most iconic hospitality concepts, to break down his journey from growing up in the south of France to building a multi-million dollar hospitality and real estate portfolio in Miami.Mathieu shares how he moved to Miami in 2007, raised capital from Europe, and began investing in distressed real estate during the 2008 financial crisis. His first deal — a retail condo on Ocean Drive purchased for $3 million — set the foundation for a vertically integrated strategy combining real estate, hospitality, and brand building.We dive into:• Buying Miami real estate at the bottom of the market• Turning a $3M restaurant into a $15M revenue concept• Scaling Marion into a $20M restaurant post-COVID• Acquiring and redeveloping the property that became Queen• Navigating a $40M construction and real estate project during uncertain times• Why hospitality is a marathon — not a sprint• Building culture, loyalty, and long-term team retention• Expanding into Las Vegas, Dubai, and beyondMathieu also opens up about the personal side of entrepreneurship — doubt, setbacks, ego, loss, and the internal work required to lead at a high level.

In this episode of The Long Game, we sit down with internationally acclaimed Architect Kobi Karp who has spent more than four decades shaping Miami’s skyline and delivering some of the market’s highest-value luxury developments.In this episode of The Long Game, we break down the mindset behind longevity, the evolution of high-end real estate, record-breaking price points, and what it takes to design projects that stand the test of time.

On this episode, we sit down with Kevin Peake, president and co-founder of NEXT Health, one of the fastest-growing brands in health optimization and longevity. We explore how Kevin helped launch and scale the company, what’s driving the shift toward proactive, data-driven medicine, and his bold vision for living well beyond 150 years. A powerful conversation on performance, prevention, and designing a longer, stronger life.

In this episode, Jay sits down with ultra-endurance athlete, entrepreneur, author, and high-performance trailblazer Alvaro Nunez. Together they unpack the mindset that drives Alvaro to tackle feats most people wouldn’t attempt — from running marathons across seven continents in seven days, conquering the harshest races on Earth, to using extreme challenges as tools for mental toughness, purpose, and personal evolution. Hear how discipline, resilience, and relentless curiosity shape his approach to life, business, and what it really takes to play the long game.

In this episode of The Long Game, Jay Roberts sits down with Dina Goldentayer, a leading Miami Beach luxury real estate expert. They discuss her career, the realities of operating at the highest level of a competitive market, and the long-term mindset required to build sustained success in real estate and beyond.

Isaac Toledano is a real estate developer and the Founder & CEO of BH Group, with active projects across Florida and partnerships with some of the most established developers in the country.Isaac joins Jay to talk about what separates long-term winners from short-term thinkers, why he only invests in prime real estate, and how conviction, speed, and selectivity shape his decision-making. He breaks down the importance of choosing the right partners, leaving ego and greed out of deals, and why his business model evolved from sole ownership to long-term joint ventures. Isaac also shares lessons learned from past mistakes, the role family and values play in his work, and why doing what’s right for the deal leads to repeat success over time.