The Long Game – Details, episodes & analysis

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The Long Game

Prosper Group

Business

Frequency: 1 episode/6d. Total Eps: 30

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.

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🇩🇪 Germany - entrepreneurship
28/07/2026
#73

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Michelle Cordeiro Grant | The Long Game w/ Jay Roberts #29

Thursday, July 30, 2026 • Duration 47:53

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 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

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Jay Parker | The Long Game w/ Jay Roberts #28

Thursday, July 23, 2026 • Duration 46:24

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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Brad Meltzer | The Long Game w/ Jay Roberts #19

Friday, May 29, 2026 • Duration 38:26

Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game by Prosper Group CEO Jay Roberts, we sit down with Brad Meltzer, President & Partner at Two Roads Development, one of the leading luxury real estate developers shaping South Florida and beyond.Brad began his career in construction in New York City after studying architecture at Tulane University, eventually rising through the ranks to become CEO of Plaza Construction. Over the past three decades, he has helped deliver some of the most iconic projects in Miami, including the Mandarin Oriental Miami, W South Beach, One Hotel South Beach, and 1000 Museum by Zaha Hadid.Today at Two Roads Development, Brad is leading large-scale luxury projects across Miami, Tampa, Las Vegas, and the Bahamas, including Four Seasons and Pendry-branded developments totaling billions of dollars in construction and investment.We dive into the evolution of Miami real estate, the importance of long-term relationships in business, the realities of managing billion-dollar developments, and the lessons Brad has learned from building some of the most ambitious projects in the country.🎯 TAKEAWAYS:• How Brad went from framing houses in New York to leading billion-dollar developments• The importance of relationships, trust, and reputation in construction and development• What Brad learned building iconic Miami projects like W South Beach and 1000 Museum• Why pre-construction planning and “zero allowance” budgeting reduce risk on major projects• The differences between developing luxury projects in Miami, Tampa, Las Vegas, and the Bahamas• Why Four Seasons remains the gold standard in branded residences• How Miami has evolved into a global city attracting top talent and capital• The biggest challenges facing Miami’s future growth and development• Why long-term relationships matter more than ever in business and lifeStay up to date with Jay Roberts:Instagram: @jayroberts

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Mike Neal | The Long Game w/ Jay Roberts #18

Episode 18

Saturday, May 23, 2026 • Duration 01:16:07

Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.

On this episode of The Long Game by Prosper Group CEO Jay Roberts, we sit down with Mike Neal, CEO of KAST Construction, one of South Florida’s most respected builders with decades of experience shaping the region’s skyline and luxury real estate market.

Born and raised in Hollywood, Florida, Mike grew up in a hardworking middle-class family where discipline, accountability, and work ethic were instilled at an early age. From mowing lawns and delivering newspapers as a kid to working difficult construction jobs alongside his father, a union electrician, Mike learned firsthand what it takes to build something from the ground up.

Today, Mike leads KAST Construction, a premier South Florida construction firm responsible for delivering some of the region’s most notable residential and commercial projects. In this conversation, we dive into leadership, construction, business growth, South Florida development, and the mindset required to succeed in one of the toughest industries in America.

🎯 TAKEAWAYS:

• How Mike Neal’s blue-collar upbringing shaped his leadership and work ethic
• The lessons he learned working construction jobs as a teenager alongside his father
• Why discipline, accountability, and consistency matter in business and life
• The realities of operating in the construction industry and managing large-scale projects
• How South Florida’s explosive growth is changing development and construction
• What it takes to build a long-term business and reputation in a highly competitive industry

Stay up to date with Jay Roberts:
Instagram: @jayroberts

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Ben Van Leeuwen | The Long Game w/ Jay Roberts #17

Episode 17

Thursday, May 21, 2026 • Duration 35:12

Never miss an episode. Sign up for The Long Game newsletter at ProsperGroup.com.

On this episode of The Long Game by Prosper Group CEO Jay Roberts, we sit down with Ben Van Leeuwen, Founder & CEO of Van Leeuwen Ice Cream, one of the most recognizable premium ice cream brands in America.

Ben started with a simple idea, a used 1988 Chevy postal truck, and just $60,000 raised from friends, family, and a college professor. Nearly two decades later, Van Leeuwen has grown into a national brand with 100+ stores across the U.S., millions of customers, and international expansion underway in Korea.

We dive into the early days of building the business, the reality of raising capital, why location changed everything on day one, how Van Leeuwen built a cult following around high-quality ingredients, and what it takes to scale a brand without losing the product quality that made it special.

🎯 TAKEAWAYS:

• How Ben turned a used postal truck into a national ice cream brand
• Why every wealthy person told him no before he raised his first $60,000
• The day-one lesson that changed how he thought about foot traffic
• Why premium ingredients became the foundation of the Van Leeuwen brand
• The unsexy operational details that make or break a growing business
• How Van Leeuwen is expanding nationally and internationally

Stay up to date with Jay Roberts:
Instagram: @jayroberts

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Allie Eichner | The Long Game w/ Jay Roberts #16

Episode 16

Friday, May 15, 2026 • Duration 47:05

On this episode of The Long Game by Prosper Group CEO Jay Roberts, we sit down with Allie Eichner, President of Continuum Companiesand one of the leading voices shaping luxury waterfront development in Miami today.Allie grew up around one of the most iconic real estate development families in the country and is now leading the next generation of the Continuum brand — the team behind the legendary Continuum South Beach towers, widely considered the gold standard for oceanfront luxury living in Miami. Today, she’s spearheading major waterfront projects including Continuum Club & Residences in North Bay Village and several other transformative developments across South Florida.We dive into the evolution of Miami luxury real estate, legacy development, waterfront living, and what it takes to build projects that stand the test of time. Allie also opens up about her unconventional upbringing, competitive mindset, early independence, and the lessons that shaped her approach to leadership and business.🎯 TAKEAWAYS:• How the Continuum brand became one of the most iconic names in Miami luxury real estate• The vision behind Continuum Club & Residences and Miami’s next wave of waterfront development• Why experiential amenities and “boat-in, boat-out” living are reshaping luxury housing• How Allie’s upbringing and competitive tennis background built resilience and independence• The realities of carrying on a legacy brand in a rapidly evolving Miami market• Why Miami continues attracting global wealth, entrepreneurs, and ultra-high-net-worth buyersStay up to date with Jay Roberts:Instagram: @jayroberts

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Tommaso Chiabra | The Long Game w/ Jay Roberts #15

Friday, May 8, 2026 • Duration 41:42

$2.8B real estate development pipeline. Become an investor here: https://prospergroup.com/invest/

On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Tommaso Chiabra, CEO and founder of Royal Yacht International and founder of Mangusta Capital.Tommaso built one of the world’s leading superyacht brokerage firms from the ground up—going from yacht supply operations during Monaco Formula 1 weekends to brokering some of the largest yacht transactions in the world.

Today, Royal Yacht International works with ultra-high-net-worth clients globally and oversees billions in yacht transactions and construction projects.We dive into the hidden world of superyachts, billion-dollar wealth, off-market deals, and how ultra-wealthy buyers operate behind the scenes.

Tommaso breaks down the business of yacht brokerage, venture investing, global entrepreneurship, and what it takes to build relationships at the highest level of business.

🎯 TAKEAWAYS:

How Tommaso built Royal Yacht International during the 2008 financial crisis

The story behind a $300 million yacht purchased sight unseen

Why relationships and information are the real leverage in luxury brokerageHow billionaires structure yacht purchases and off-market transactions

Why Miami has become a major global hub for entrepreneurs and investorsT

ommaso’s philosophy on longevity, discipline, and sustainable performance.

Stay up to date with Jay Roberts:Instagram: @jayroberts

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MJ Green | The Long Game w/ Jay Roberts #14

Episode 14

Thursday, April 30, 2026 • Duration 36:35

$2.8B real estate development pipeline. Become an investor here: https://prospergroup.com/invest/

On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with M.J. Green, Chief of Economic Development & Strategy at the Miami Downtown Development Authority.

MJ brings a unique background—from wealth management at major financial institutions to building community development funds that have deployed capital across the U.S.—before stepping into one of the most important roles shaping Miami’s future.

We dive into what’s really driving Miami’s explosive growth—from downtown development and infrastructure to the influx of capital, talent, and global attention.

MJ breaks down the strategy behind transforming Miami into a true 24/7 urban core—and why the job is far from finished.

We also get into the numbers behind the boom, the evolution from a tourism-driven city to a diversified business hub, and what it will actually take for Miami to compete on a global level over the next decade.

🎯 TAKEAWAYS:

Why Miami is in a once-in-a-generation “timing window” for growth

How the DDA is using grants and incentives to attract restaurants, retail, and startups

The real impact of 500,000+ monthly cruise passengers on downtown economics

Why downtown Miami now has three built-in customer bases (residents, workers, tourists)

How projects like Flagler Street, the Baywalk, and the Underline are reshaping connectivity

Why Miami shouldn’t try to become Silicon Valley—and what it should be instead

How rising wages and population growth are stabilizing the city’s economy

The role of relationships and community in building long-term business success

Fredrik Eklund | The Long Game w/ Jay Roberts #13

Episode 13

Thursday, April 23, 2026 • Duration 01:02:34

$2.8B real estate development pipeline. Become an investor here: https://prospergroup.com/invest/On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Fredrik Eklund, one of the most successful real estate brokers in the world.Fredrik has sold nearly $30 billion in real estate, sold out over 140 buildings, and became a global name through Million Dollar Listing New York - but he started in New York with no clients, no network, and no safety net.We dive into his journey from early startup failures to breaking into real estate and using TV to build one of the most powerful personal brands in the industry. He explains how he went from his first deal to becoming a go-to broker for developers worldwide.We also cover what separates elite brokers, why authenticity wins, and how building a strong team has kept him at the top for over two decades.🎯 TAKEAWAYS:Why Fredrik believes being fully yourself is the ultimate sales advantageHow he used reality TV as a strategic tool to build trust at scaleThe real story behind his first deal—and why he still remembers every detailWhy new development is the highest level of real estate and how he dominates itHow timing, luck, and preparation combined to launch his careerWhy the best brokers think like developers—not just salespeopleThe importance of building a team that feels like family (and why solo agents fall behind)What ultra-wealthy buyers actually want—and how it differs by marketWhy long-term success in real estate takes at least 5 years of real commitmentHow exposure from TV turned into daily inbound listings and deal flowStay up to date with Jay Roberts:Instagram: https://instagram.com/jayroberts

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Don Peebles III | The Long Game w/ Jay Roberts #12

Thursday, April 16, 2026 • Duration 35:26

On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Don Peebles III, Chief Operating Officer of The Peebles Corporation, the largest Black-owned real estate development company in America.We dive into his origin story—growing up at the dinner table learning cap rates before long division, being immersed in the family business from an early age, and building his own credibility inside one of the most respected development firms in the country.Our conversation explores how The Peebles Corporation has built a four-decade track record across major U.S. cities by targeting both ends of the market—ultra-luxury and affordable housing—while most developers compete in the middle. Don breaks down the story behind the Bath Club, one of Miami Beach’s most historic private clubs and now a cornerstone asset in the firm’s portfolio.He also shares why off-market relationships are the only deals worth doing, what the next generation of real estate development looks like, and the mindset that has kept The Peebles Corporation at the top for over 40 years.This episode reveals what it looks like when legacy, credibility, and the right market thesis compound across generations.🎯 TAKEAWAYS:Why The Peebles Corporation targets both ends of the barbell—ultra-luxury and affordable housing—and why chasing the middle is a losing strategyThe full story behind the transformation of the Bath Club into one of the firm’s most iconic assets as it approaches its 100th yearWhy a 12-seat omakase restaurant inside the club could be on the verge of a Michelin starHow nearly 5,000 affordable housing units could define the firm’s next chapter—and why affordability should be a stepping stone to ownershipHow Peebles wins deals by going directly to sellers and avoiding marketed listings entirelyWhy information is more valuable than money—and how transparency builds long-term investor trustHow AI is reshaping real estate and why interpersonal skills now matter more than technical expertiseIf you’re interested in investing with Prosper Group, visit https://prospergroup.com/invest/Stay up to date with Jay Roberts:Instagram: https://www.instagram.com/jayrobertsFor more information about Don Peebles III and The Peebles Corporation:https://peeblescorp.com

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The Long Game – Details, episodes & analysis

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The Long Game – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

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Publication history

Latest published episodes

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