Jay Roberts
The Long Game with Jay Roberts
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Inside the minds of founders, builders, and investors playing the long game.

Testimonials

In Their Words

Dina Goldentayer portrait

Dina Goldentayer

Douglas Elliman

Appearing on The Long Game by Jay Roberts was a great experience and delivered real value. Shortly after the episode aired, I received a direct business lead from a viewer. If you have the chance to be on the show, say yes. Jay has built something truly special; the engagement and positivity surrounding the show create a strong buzz.

Fredrik Eklund portrait

Fredrik Eklund

Douglas Elliman

Working with Jay Roberts has been a real pleasure. From day one, it was clear he brings something rare to the table – not only with his digital presence, but general mindset. The Long Game is a window into how Jay actually thinks and builds. It’s the vision that shows up in everything Prosper Group touches. I’m excited to be partnering with Jay and his team, and I’m looking forward to all the great things we’re going to accomplish together. Jay is exactly the kind of person you want in your corner, and I’m proud to be in his.

Isaac Toledano portrait

Isaac Toledano

BH Group

Being featured on The Long Game was a great experience and a meaningful opportunity to have a conversation grounded in real industry perspective. My conversation with Jay Roberts felt natural and substantive, and his experience as both host and a developer added depth to the discussion. I’m pleased to have been part of it, as it’s a platform focused on how long term value is actually built in today’s market, a core focus of BH Group.

Kevin Peake portrait

Kevin Peake

Next Health

When I came on The Long Game, it was clear this wasn't just another surface conversation about health and wellness - Jay is genuinely part of this world. He's deep in the biohacking space, he uses our services, and he's already thinking about how to bring Next Health's longevity experience into Prosper Group's developments. That vision is rare as he's taking the extra step, adding thought and care to how people want to live. When he did the Business Journal shoot at our facility, he showed up the same way he does everything: all in. Jay doesn't just support the people in his network, he amplifies them. Prosper Group is building something different, and I'm proud to be part of that orbit.

Kobi Karp  portrait

Kobi Karp

Founder, Kobi Karp Architecture & Interior Design

I just wanted to take a moment to thank you for having me as a guest on The Long Game podcast. It was truly a rewarding experience. Having known each other for a long time, our conversation felt natural and engaging, and I truly enjoyed the depth and authenticity we were able to bring to the discussion.

What stands out about The Long Game is its focus on longevity. The show isn’t about quick wins; it’s about building something meaningful over time with discipline, consistency, and purpose, values that really resonate with me. Our conversation about staying focused, taking care of yourself, and surrounding yourself with the right people really hit home, as that’s what allows you to perform at your highest level.

I also want to commend the show for its commitment to delivering real-world experiences and practical advice. It was a wonderful opportunity to reflect on my career and share lessons that I hope will resonate with listeners, particularly those interested in how design shapes both spaces and businesses.

Thank you again for the chance to be a part of a platform that encourages long-term thinking and staying committed to the process. I’m proud to have contributed to the podcast and look forward to supporting The Long Game in the future.

Rich Somers

Rich Somers

Jay is a world-class operator who’s building something special with Prosper Group. He’s executing at a high level, communicates clearly, and consistently delivers. We’ve really enjoyed working with him and his team—great people doing big things. Best of the best.

Brad Meltzer

Brad Meltzer

Two Roads

I’ve been in construction and real estate a long time and have seen a wide range of approaches to the business. What stood out to me about Jay is that he is a student of the craft. On The Long Game, we focused on what actually matters, how you think, how you make decisions, and how you build over time.

That mindset is reflected in Prosper Group’s work. It’s a thoughtful, disciplined approach to development with a clear focus on building something that endures.

Leonard Chinchay

Leonard Chinchay

Assets Funding Capital

From the moment we met, I knew Jay was someone I could trust. We bonded over his mastery of finance and capital markets, but what stood out even more was how easy he is to do business with. Our conversation on The Long Game felt natural, sharp, and genuinely enjoyable. It’s a great platform for any expert wanting to come on and share their knowledge and speak with a peer.

Featured Guests

Conversations With Visionaries Who Play the Long Game

Isaac Toledano

Isaac Toledano

Founder & CEO of BH Group

Dina Goldentayer

Dina Goldentayer

#1 Agent at Douglas Elliman, Ultra Luxury Real Estate Expert

Fredrik Eklund

Fredrik Eklund

Founder of #1 Eklund Gomes team, star of Million Dollar Listing NY + LA

Kevin Peake

Kevin Peake

Producer/Investor, Founder at MGT Health

Kobi Karp

Kobi Karp

Founder & President of Kobi Karp Architecture & Interior Design

Ana Bozovic

Ana Bozovic

Founder of Analytics Miami and MiamiDeal Sheet

Mathieu Massa

Mathieu Massa

Owner of Mr.Hospitality, CEO of Massa Investment Group

Michael Sinus

Michael Sinus

President & CEO of the Florida Council of 100

Brian Gale

Brian Gale

Vice Chairman of Cushman & Wakefield of Florida

Ben Van Leeuwen

Ben Van Leeuwen

Founder & CEO of Van Leeuwen Artisan Ice Cream

Fernando De Nuñez y Lugones

Fernando De Nuñez y Lugones

CEO & Co-Founder of Vertical Developments

Alvaro Nuñez

Alvaro Nuñez

CEO & Co-Founder of Vertical Developments Group, Extreme Athlete

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The Long Game reaches an engaged, high-net-worth audience across real estate, finance, and entrepreneurship. Download the media kit for demographics, rates, and formats.

Views on Instagram @jayroberts
30M++
*Interactions on Instagram in the last 90 days
516K
Followers on Instagram
185K
Views & counting for TLG content on Instagram
1.2M++
*Views across social media platforms in the last 30 days
3.1M++
Shares on Instagram
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