Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Fred Voccola, former CEO and current vice chairman of Kaseya and chairman and CEO of simPRO Group.Fred shares his journey from teaching himself to code and starting his first software company in college to becoming one of the most accomplished operators in the technology industry.He explains how he sold his first company during his senior year, helped take another company public, built and exited multiple software businesses, and eventually transformed Kaseya from roughly $50 million in revenue into a $1.5 billion global business valued at approximately $15 billion.Jay and Fred discuss scaling companies, acquiring and integrating businesses, developing high-performance teams, and why successful founders must remain deeply involved in the details of their organizations.Fred also shares the inside story of the 2021 Kaseya ransomware attack, including the decision to immediately shut down the platform, work alongside the FBI, communicate transparently with customers, and protect millions of businesses around the world.The conversation explores artificial intelligence, cybersecurity, preventative medicine, Miami’s entrepreneurial culture, and Fred’s vision for simPRO, an AI-powered field service platform helping trade businesses dramatically improve their efficiency and profitability.🎯 TAKEAWAYS:• How Fred started and sold his first software company while still in college• How he helped build and exit multiple successful technology companies• How Kaseya grew from roughly $50 million to $1.5 billion in revenue• Why obsessive, hands-on founders build the strongest organizations• How transparency helped Kaseya navigate a major ransomware attack• Why Fred believes Miami is uniquely suited for entrepreneurship• How AI could transform medicine, cybersecurity, and field service businesses• Why entrepreneurs must love the journey rather than focus only on an exit• How simPRO is using AI to improve profitability for trade contractors• Why grit, accountability, customer service, and long-term thinking are essential for successStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com

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On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Michelle Cordeiro Grant, founder and CEO of Gorgie, one of the fastest-growing better-for-you energy drink brands in the United States.

Michelle shares her journey from growing up in rural Pennsylvania as the daughter of Indian immigrants to building a career at companies including Macy’s, Victoria’s Secret, and Thrillist Media Group.

She explains how those experiences helped her launch Lively, grow it into a powerful community-driven brand, and sell the company for more than $100 million just four years later.

Jay and Michelle discuss raising her first $1.5 million, learning startup financing in real time, finding mentors, and building teams that could support rapid growth.

Michelle also shares how she created Gorgie through focus groups, taste tests, social media, and constant customer feedback. Today, the brand is sold in more than 15,000 stores nationwide, has achieved 600% year-over-year retail growth, and counts Jon Bon Jovi and Alix Earle among its investors.

The conversation explores entrepreneurship, consumer brands, grassroots marketing, customer retention, resilience, and why progress over perfection is essential when playing the long game.

🎯 TAKEAWAYS:

• How Michelle built and sold Lively for more than $100 million
• Why experience, mentorship, and curiosity are essential for founders
• How customer feedback shaped Gorgie from the beginning
• Why community is more powerful than traditional marketing
• How Gorgie expanded into more than 15,000 stores nationwide
• Why retention and repeat purchases matter more than attention alone
• How Jon Bon Jovi and Alix Earle became investors in the brand
• Why founders should choose progress over perfection

Stay up to date with Jay Roberts:

Instagram: @jayroberts
Website: ProsperGroup.com

On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Jay Parker, CEO of Douglas Elliman’s Florida region and President of Douglas Elliman Development Marketing in Florida.

Jay shares how moving from Toronto to Miami, attending the University of Miami School of Law, and building a career in real estate helped shape his approach to leadership, relationships, and business.

He explains how Douglas Elliman grew from a small Florida operation into one of the state’s leading luxury real estate platforms, with more than 1,000 agents and a new development pipeline approaching $20 billion.

Jay and Jay also discuss the rise of branded residences, what makes luxury developments successful, why Florida’s real estate growth is not a bubble, and which South Florida markets still offer major opportunity.

The episode offers valuable lessons on leadership, market expertise, team building, adaptability, and why playing the long game means staying passionate, disciplined, and committed to the process.

🎯 TAKEAWAYS:
• How Jay Parker helped grow Douglas Elliman’s Florida operation
• Why Florida remains a major luxury real estate opportunity
• What makes branded residences and new developments successful
• Why South Florida’s current market is different from past bubbles
• How agents can build lasting careers through expertise and consistency
• Why strong relationships and leadership matter in business

Stay up to date with Jay Roberts:

Instagram: @jayroberts
Website: ProsperGroup.com

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On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Melissa Medina, Co-Founder and CEO of eMerge Americas, the global technology platform that has helped transform Miami into a major hub for innovation, entrepreneurship, and investment.

Melissa shares how growing up as a first-generation Cuban American and watching her father, Manny Medina, build and sell Terremark Worldwide shaped her approach to leadership, risk, reputation, and business.

Jay and Melissa discuss how a simple conversation about Miami’s lack of a technology ecosystem became eMerge Americas, a global conference and year-round platform connecting founders, investors, corporations, universities, and government leaders from more than 50 countries.

They also explore the early skepticism surrounding Miami’s technology potential, the challenges of surviving the pandemic, the migration of capital and companies into South Florida, and why Miami’s growth has become impossible to ignore.

Melissa also shares how eMerge supports early-stage founders through accelerator programs, pitch competitions, investor connections, and educational initiatives, helping create thousands of jobs and billions of dollars in economic impact.

The episode offers valuable lessons on entrepreneurship, resilience, community building, investing, leadership, and why playing the long game means believing in a vision before the rest of the world sees it.

🎯 TAKEAWAYS:

• How Melissa Medina helped build eMerge Americas into a global technology platform
• How Miami became a rising destination for technology, capital, and entrepreneurship
• Why reputation, consistency, and keeping your word matter in business
• How eMerge connects founders with investors, corporations, and opportunities
• Why resilience and adaptability are essential when building something new
• How AI, quantum technology, fintech, and national security are shaping innovation
• Why in-person relationships are becoming more valuable in an increasingly digital world

Stay up to date with Jay Roberts:

Instagram: @jayroberts
Website: ProsperGroup.com

Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Alfonso Costa Jr., Chief Operating Officer of The Falcone Group, one of South Florida’s leading real estate development firms.Alfonso shares his journey from Yale, Harvard Law School, and Oxford to serving as a senior official at the U.S. Department of Housing and Urban Development during the Trump administration, where he helped advance major housing and economic development initiatives including Opportunity Zones.Jay and Alfonso discuss the power of discipline, education, athletics, public service, and long-term mentorship in shaping a high-performance career. Alfonso also shares how his work in government led him into private real estate development, where he now helps oversee a portfolio of large-scale projects across South Florida.The conversation explores Opportunity Zones, the Live Local Act, workforce housing, public-private partnerships, Miami Worldcenter, and the long-term vision behind major mixed-use developments that reshape cities over decades.Jay and Alfonso also dive into Miami’s rise as a global destination for capital, real estate, and development, as well as the importance of patience, flexibility, and staying power in both business and life.The episode offers valuable lessons on leadership, real estate, policy, long-term investing, community impact, and why playing the long game means building with vision, discipline, and purpose.🎯 TAKEAWAYS:• How Alfonso Acosta Jr. built a path from elite academics and athletics into government and real estate• Why discipline, teamwork, and lifelong learning are critical to long-term success• How Opportunity Zones are driving investment into underserved communities• Why the Live Local Act is changing the future of workforce and attainable housing in Florida• The strategy behind Miami Worldcenter and large-scale mixed-use development• Why patience and flexibility are essential in real estate cycles• How public-private partnerships can unlock new housing, jobs, and community growth• Why Miami continues to attract major domestic and international capital• The importance of asking questions, staying humble, and learning from people around youStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com

Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Kamal Hotchandani, Co-Founder and CEO of Haute Media Group, the luxury media company behind Haute Living, Haute Residence, Haute Jets, Haute Beauty, Haute Wealth, and more.Kamal shares how he built a single Miami-based luxury publication into a global media platform spanning more than 20 markets, serving some of the world's most influential entrepreneurs, investors, developers, celebrities, and luxury brands. He discusses the power of long-term relationship building, creating value before asking for anything in return, and how community became the foundation of Haute Media's success.Jay and Kamal also explore the evolution of luxury media, the rise of AI-powered search and generative engine optimization (GEO), Miami's emergence as a global capital for wealth and real estate, and why the next decade belongs to businesses that adapt early to artificial intelligence.The conversation offers valuable lessons on entrepreneurship, branding, relationship capital, innovation, and why playing the long game means creating opportunities that compound over decades.🎯 TAKEAWAYS:• How Kamal built Haute Living into one of the world's leading luxury media brands• Why leading with value creates long-term business opportunities• The importance of building authentic relationships and community• How luxury brands create lasting customer loyalty• Why Miami has become a global hub for wealth, luxury, and entrepreneurship• How AI and generative search are transforming media, marketing, and business• The strategy behind expanding into luxury real estate, aviation, and lifestyle businesses• Why patience, consistency, and long-term thinking are the foundation of lasting successStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com

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On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Matthew Whitman Lazenby, President and CEO of Whitman Family Development and fourth-generation steward of one of Miami's most influential real estate families.

Matthew shares the remarkable story of how his family's journey began in Miami Beach in 1912 and evolved into developing some of the country's most iconic luxury destinations, including Bal Harbour Shops and Brickell City Centre. He discusses the vision behind Bal Harbour Shops, why his grandfather rejected the traditional enclosed mall concept, and how a century of long-term thinking helped build one of the highest-performing retail destinations in the world.

Jay and Matthew also explore the challenges of expanding an iconic property, the future of mixed-use development, Florida's Live Local Act, workforce housing, and the realities of navigating community opposition while planning for the next generation.

The conversation offers valuable lessons on family businesses, leadership, patience, and what it truly means to play the long game when your family's legacy spans more than 100 years.

🎯 TAKEAWAYS:

• The 100+ year history of the Whitman family's real estate legacy
• How Bal Harbour Shops became one of the world's premier luxury shopping destinations
• Why long-term thinking beats short-term decision making in real estate
• The philosophy behind curating unforgettable retail experiences
• The challenges of expanding landmark developments in today's regulatory environment
• How Florida's Live Local Act is reshaping workforce housing
• Lessons on leading a multi-generational family business
• Why preserving a legacy requires constant innovation and thoughtful evolution

Stay up to date with Jay Roberts:

Instagram: @jayroberts
Website: ProsperGroup.com

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On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Elizabeth MacBride, financial journalist, national bestselling author, and co-author of Capitalism Evolution: The New American Economy and What It Means for Your Business and Our Future.

Elizabeth shares insights from nearly three decades as a journalist covering entrepreneurship, business, and economic systems. The conversation explores how capitalism has evolved over the last 50 years, the rise of shareholder-driven corporate thinking, and why new ownership models may help create stronger companies and broader prosperity.

Jay and Elizabeth discuss employee ownership, long-term thinking, startup culture, AI's impact on entrepreneurship, the future of work, and why successful leaders must balance speed in execution with patience in achieving meaningful results.

The episode also dives into the principles behind playing the long game, drawing lessons from Warren Buffett, Charlie Munger, Jack Bogle, Vanguard, Wealthfront, and some of the most successful business leaders of the modern era.

🎯 TAKEAWAYS:

• Why capitalism is constantly evolving and what comes next
• The difference between short-term and long-term business thinking
• How employee ownership can create stronger companies
• Lessons from Warren Buffett, Charlie Munger, and Jack Bogle
• Why startup success requires both speed and patience
• The impact of AI on entrepreneurship and company creation
• Building businesses that create value for employees, customers, and shareholders
• Practical advice for playing the long game in business and life

Stay up to date with Jay Roberts:

Instagram: @jayroberts
Website: ProsperGroup.com

Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Sam Nazarian, one of the most influential entrepreneurs in hospitality, nightlife, and real estate.Sam shares his journey from immigrating to the United States after the Iranian Revolution to building a global hospitality empire that included more than 100 hotels and 150 restaurants. He discusses the early lessons that shaped his career, how his family’s success with Qualcomm led to opportunities in real estate, and the story behind launching his first nightclub in Beverly Hills.The conversation also explores the growth of SBE, identifying opportunities before they become mainstream, the evolution of luxury hospitality, and why wellness, longevity, and lifestyle are becoming increasingly important in the future of luxury real estate and hospitality.🎯 TAKEAWAYS:• Sam’s family’s journey from Iran to the United States following the 1979 Iranian Revolution• How Qualcomm transformed his family’s financial future• Why his father chose to diversify into real estate• The story behind launching his first nightclub in Beverly Hills• Building SBE into a global hospitality platform• The intersection of luxury hospitality, wellness, and longevity• Why certain luxury real estate ecosystems continue to thrive even during market downturnsStay up to date with Jay Roberts:Instagram: @jayroberts

Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts joins Carlos Rosso, Founder & CEO of Rosso Development and one of the most influential real estate developers shaping Miami’s urban landscape, for an exclusive tour of The Standard Residences Midtown Miami.After spending more than two decades at Related Group, where he rose to become President of Condominium Development under Jorge Pérez, Carlos launched Rosso Development and has since become the driving force behind transformative projects across South Florida.In this special walkthrough episode, Carlos takes viewers behind the scenes of The Standard Residences Midtown Miami and shares the vision behind Midtown Park, a multi-phase mixed-use development helping connect Wynwood, Midtown, and the Design District. As they tour the property, Carlos discusses the importance of walkability, public spaces, community-driven development, and why Miami continues to attract residents, investors, and businesses from around the world.🎯 TAKEAWAYS:• An inside look at The Standard Residences Midtown Miami• Carlos Rosso’s journey from Related Group to launching Rosso Development• The vision and master plan behind Midtown Park• How Midtown Miami evolved into one of the city’s most desirable neighborhoods• Why walkability, parks, and public spaces increase long-term value• The future of Miami real estate and continued population growth• Lessons learned from developing some of South Florida’s most successful projects• Why long-term thinking remains the key to real estate investingStay up to date with Jay Roberts:Instagram:LinkedIn:Website:Follow Prosper Group:Instagram:LinkedIn:Website: ProsperGroup.com