Episode 301: 27 Years of NYC Real Estate Investing Lessons ft. Jude Bernard
Release Date: 01/15/2026
Episode 301: 27 Years of NYC Real Estate Investing Lessons ft. Jude Bernard
Boro4Boro
Most investors focus on cash flow. Jude Bernard focuses on the full picture — equity walk-in, forced appreciation, debt reduction and tax strategies that compound over decades. In our Season 3 premiere, we sit down with Jude to learn what 27 years of NYC real estate investing has taught him about finding deals, building wealth and playing the long game. Jude is a licensed broker, general contractor, landlord and founder of The Brooklyn Bank, a nonprofit dedicated to financial literacy in urban communities. Timestamps: 0:00 – Intro 2:15 – What "real estate entrepreneur" means 5:30...
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Episode 208: Urbanist Ariel Breaks Down NYC’s Zoning Future
Boro4Boro
In this episode of Boro4Boro, Brown Harris Stevens agents Matthew Wynter, Isaiah Ajala, Traci Byers, and Scottie Cabrera welcome Ariel Viera—better known as Urbanist Ariel—for an in-depth conversation on New York City zoning. Together, they break down the current zoning landscape, explore upcoming policy changes, and discuss how these shifts could reshape the city in the near future. Filmed at Brown Harris Stevens’ Studio 1873, Part of the Mastery of Real Estate (MORE) Network. Subscribe: https://podcasts.apple.com/us/podcast/boro4boro/id1731246276 Connect with Matthew Wynter:...
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Episode 207: Lighting Up the Future of Real Estate with Matt Emmi
Boro4Boro
On this very special episode of Boro4Boro, filmed at the New York Real Estate Expo, host Matthew Wynter sits down with Matt Emmi, owner and principal of lighting technology firm, OneButton to discuss all things lighting and design in New York City real estate. All episodes filmed and recorded as part of Brown Harris Stevens’ Mastery of Real Estate (MoRE) Network. Subscribe: https://podcasts.apple.com/us/podcast/boro4boro/id1731246276 Connect with Matthew Wynter: https://www.bhsusa.com/real-estate-agent/matthew-wynter Connect with Isaiah Ajala: ...
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Episode 206: Navigating Luxury in New York with Louise Phillips Forbes
Boro4Boro
In this episode of Boro4Boro, Brown Harris Stevens agents Matthew Wynter, Isaiah Ajala, Traci Byers, and Scottie Cabrera welcome Brown Harris Stevens’ powerhouse broker, Louise Phillips Forbes, as they discuss the luxury NYC market, and so much more. Filmed at Brown Harris Stevens’ Studio 1873, Part of the Mastery of Real Estate (MORE) Network. Subscribe: https://podcasts.apple.com/us/podcast/boro4boro/id1731246276 Connect with Matthew Wynter: https://www.bhsusa.com/real-estate-agent/matthew-wynter Connect with Isaiah Ajala: https://www.bhsusa.com/real-estate-agent/isaiah-ajala Connect...
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Episode 205: Events and Interiors — A Night of Design Discussions at Carl Hansen & Søn
Boro4Boro
In this episode of Boro4Boro, Brown Harris Stevens agents Matthew Wynter, Isaiah Ajala, Traci Byers, and Scottie Cabrera recap the latest interior design and release estate trends with designers, John Douglas Eason and Katie Lydon, at the Boro4Boro Live Event at Carl Hansen & Søn’s Flagship Midtown East showroom. Filmed at Brown Harris Stevens’ Studio 1873, Part of the Mastery of Real Estate (MORE) Network. Subscribe: Connect with Matthew Wynter: Connect with Isaiah Ajala: Connect with Traci Byers: Connect with Scottie Cabrera: Connect with John Douglas Eason:...
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Episode 204: The Social Strategy Behind Real Estate Success
Boro4Boro
On this special episode of Boro4Boro, host Matthew Wynter is joined by top Brown Harris Stevens brokers Matt Melinger and Jordan Silver for a deep dive into the strategies behind their impressive social media followings. They share how leveraging digital platforms has helped them build their personal brands, expand their networks, and drive real estate success in a competitive market. Filmed at this year’s The Real Deal Forum. All episodes filmed and recorded as part of Brown Harris Stevens’ Mastery of Real Estate (MoRE) Network. Subscribe: Connect with Matthew Wynter: Connect...
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Episode 203: New York City Residential Sales Vs Rental Trends
Boro4Boro
In this episode of Boro4Boro, Brown Harris Stevens agents Matthew Wynter, Isaiah Ajala, Traci Byers, and Scottie Cabrera dive into the latest trends and updates in residential sales versus rentals across their individual markets. Tune in for expert insights and on-the-ground perspectives from these seasoned professionals. Filmed at Brown Harris Stevens’ Studio 1873, Part of the Mastery of Real Estate (MORE) Network. Subscribe: Connect with Matthew Wynter: Connect with Isaiah Ajala: Connect with Traci Byers: Connect with Scottie Cabrera: Sponsored by The Everset: Brown Harris Stevens...
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Episode 202: City of Yes Initiative with Council Member, Kevin C. Riley
Boro4Boro
In this episode of Boro4Boro, Brown Harris Stevens Agents, Matthew Wynter, Isaiah Ajala, Traci Byers, and Scottie Cabrera, welcome New York City District 12 Council Member, Kevin C. Riley to discuss the City of Yes for Housing Opportunity Initiative, which includes housing and economic opportunities plus a push for carbon neutrality. Filmed at Brown Harris Stevens’ Studio 1873, Part of the Mastery of Real Estate (MORE) Network. Subscribe: Connect with Matthew Wynter: Connect with Isaiah Ajala: Connect with Traci Byers: Connect with Scottie Cabrera: Learn More About the City of Yes...
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Episode 201: The Do’s and Don’ts of Title Insurance
Boro4Boro
In the season two premiere episode of Boro4Boro, Brown Harris Stevens Agents, Matthew Wynter, Isaiah Ajala, Scottie Cabrera, and Traci Byers, welcome guest, Muhayla Dobbs of Pro National Title Agency to discuss the importance of title insurance and how it can protect the home buyer against potential issues with the property's title. Filmed at Brown Harris Stevens’ Studio 1873, Part of the Mastery of Real Estate (MORE) Network. Subscribe: Connect with Matthew Wynter: Connect with Isaiah Ajala: Connect with Traci Byers: Connect with Scottie Cabrera: Connect with Muhayla Dobbs: ...
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Episode 109: New York City Real Estate Moving into 2025
Boro4Boro
As we come to the close of the Boro4Boro first season, and 2024 overall, join the team as they recap all the insights and revelations they’ve shared this year, as well as their forecasts for the New York City real estate market moving forward. Filmed at Brown Harris Stevens’ Studio 1873, Part of the Mastery of Real Estate (MORE) Network. Subscribe: This episode is sponsored by Shovlin Mattress, a leading premium bedding manufacturer offering bespoke products and services. To learn more and explore the brand’s mattress collections, click here: Connect with Matthew Wynter: ...
info_outlineMost investors focus on cash flow. Jude Bernard focuses on the full picture — equity walk-in, forced appreciation, debt reduction and tax strategies that compound over decades.
In our Season 3 premiere, we sit down with Jude to learn what 27 years of NYC real estate investing has taught him about finding deals, building wealth and playing the long game. Jude is a licensed broker, general contractor, landlord and founder of The Brooklyn Bank, a nonprofit dedicated to financial literacy in urban communities.
Timestamps:
0:00 – Intro
2:15 – What "real estate entrepreneur" means
5:30 – How Jude got his start
8:45 – Staying in specific neighborhood pockets
12:20 – The Class B short-term rental strategy
18:00 – Group economics and SEC considerations
24:30 – Knowing better, doing better
28:45 – Finding deals through relationships
35:00 – Due diligence red flags
42:15 – Reading a neighborhood before renovating
48:30 – Highest and best use
54:00 – Building your team
58:30 – Jude's call to action
Guest: Jude Bernard
IG: @mr.judebernard
Sponsor:
Romer Debbas — Full-service real estate law | romerdebbas.com
Boro4Boro highlights the best of NYC real estate — neighborhoods, market insights and conversations with industry leaders.
Part of the Mastery of Real Estate (MORE) Network. Filmed at Brown Harris Stevens' Studio 1873.
Hosts:
Matthew Wynter | @milliondollarwynter
https://www.bhsusa.com/real-estate-agent/matthew-wynter
Isaiah Ajala | @isaiahajala
https://www.bhsusa.com/real-estate-agent/isaiah-ajala
Traci Byers | @uptowntraci
https://www.bhsusa.com/real-estate-agent/traci-byers
Scottie Cabrera | @scottiecabrerahomes
https://www.bhsusa.com/real-estate-agent/scottie-cabrera
Subscribe to Boro4Boro for more conversations on NYC real estate.
https://podcasts.apple.com/us/podcast/boro4boro/id1731246276
Brown Harris Stevens is one of the largest privately owned real estate brokerages in the country, with more than 40 offices across four states: New York, New Jersey, Connecticut, and Florida.
https://bhsusa.com/