Episode 301: 27 Years of NYC Real Estate Investing Lessons ft. Jude Bernard
Thu Jan 15 2026
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 – 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/
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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 – 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/