Prosper Group

The Long Game

Business EN ↓ 27 episodes

The Long Game is a podcast hosted by Jay Roberts, CEO of Prosper Group. It is a conversational podcast series featuring billionaire investors, world-class operators, and elite capital allocators who have built enduring wealth through discipline, conviction, and resilience. This podcast explores how real fortunes, brands and companies are created - not overnight, but across cycles - by those who understand risk, survive setbacks, and compound trust, capital, and judgment over decades.

Author

Prosper Group

Episodes

Dina Goldentayer | The Long Game w/ Jay Roberts #002 04.02.2026 39:54

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 | The Long Game w/ Jay Roberts #001 28.01.2026 47:58

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 b...