From Special Ed Teacher to Real Estate Empire: Eli Karp’s Rise, Fall & Fight to Rebuild

Building from $25,000 to a Half Billion: The Hello Living Story

How does a special ed teacher with zero real estate experience build a $500 million real estate empire? In the latest episode of Confronting the Impossible, Leo Jacobs sits down with Eli Karp, founder and CEO of Hello Living, for an extraordinary journey through grit, growth, betrayal and the relentless pursuit of vision.

From humble beginnings in Brooklyn to developing one of the most recognizable residential brands in New York real estate, Eli shares how he built not just buildings-but entire communities.

The Genesis: From Traffic Jams to Visionary Development

It all began in 2005, with Eli commuting through run-down Brooklyn neighborhoods as a special education teacher. Inspired by the empty lots and aging storefronts he passed daily, Eli took a leap of faith. He scraped together $25,000 - even borrowing from credit cards meant for debt payments - to lock in his first property: 925 Pacific Street.

He had no architecture experience. No real estate resume. Just a passion for creating - and an idea: build luxury where no one else dared.

Creating the Community Before the Condo

The success of his first project, Pacific Blue, wasn’t just about floor plans. Eli’s obsession with shared amenities, community-building, and unique architectural design led to the birth of Hello Living - a new kind of residential experience.

While most developers stuck to cookie-cutter units, Eli built high-ceiling, flow-through apartments with a communal vision: "Say Hello to a New Way of Living."

Brand Power & Organic Growth

As blogs and publications started recognizing his impact, Eli didn't just build homes - he built a brand. Residents, investors, and even local business owners began following his developments. Some investors even used Hello Living projects as beacons for their own commercial ventures nearby.

And it worked. Prices skyrocketed. Buildings sold for $600–$650 per foot, outpacing the original projections by nearly double.

The Price of Partnership: Freedom vs. Control

Not everything was smooth. Eli’s first major investor -"Tony"- funded his dream but later tried to control it, treating Eli as an employee rather than a partner. Eli eventually walked away from properties, profits, and partnerships - buying his freedom to reclaim his vision.

Lesson? Never start without a signed agreement, no matter how excited they seem.

Hello Living Expands - and So Does the Risk

From 2012 to 2020, Hello Living exploded across Brooklyn - Crown Heights, Prospect Lefferts Gardens, Downtown Brooklyn - developing up to 15-story buildings with private elevators, shared amenities, and units designed down to the square inch.

But with success came complexity.

When Lending Becomes Predatory

The podcast takes a sobering turn as Eli reveals the darker side of real estate finance-predatory lenders, note-buying, and alleged strategic defaults.

One lender, Madison Realty Capital, allegedly bought his performing loans, delayed funding, and then backdated a default, demanding millions more in interest. This triggered legal and financial chaos, jeopardizing years of work.

This episode isn’t just about real estate-it’s a case study in entrepreneurship, resilience, and the emotional cost of ambition.

It’s also a powerful reminder that:

✅ Passion can move markets

✅ Great brands are born from great vision

✅ Bad contracts can destroy good businesses

✅ Debt is not just money-it’s leverage, risk, and control

✅ Success means nothing if you can’t protect it

Whether you're just starting out or managing a portfolio worth millions, this conversation will challenge how you think about growth, risk, and resilience.

🎧 Watch the full episode for a rare, brutally honest look behind the curtain of New York real estate and what it takes to build something that lasts.

PODCAST - Confronting the Impossible with Leo Jacobs.

Leo Jacobs, Founder and CEO of Jacobs PC

Known for finding creative, expedient solutions to complex and high-profile cases, Leo excels in matters including distressed investment and asset management, real estate law, corporate law, dispute resolution, business divorces, negotiation, and more. Leo’s extensive expertise in debt and equity structures enables him to employ a full spectrum of legal tools to achieve swift, optimal results for clients. His practice, Jacobs P.C., bridges commercial litigation, corporate transactions, and financial rehabilitation, handling cases across federal, state, and bankruptcy courts, as well as administrative tribunals.

If you would like to join the podcast email requests to pr@jacobspc.com