The Price of Ego: Real Estate, Emotion & What It Takes to Get the Deal Done

In today’s market, the highest price doesn’t win — the real price does.

And often, that price is shaped not by appraisals or comps, but by emotion, ego, and timing.

In this powerful episode of Confronting the Impossible, Leo Jacobs sits down with Bernadette Brennan, Head of Commercial at SERHANT., for a behind-the-scenes look at what really drives commercial real estate deals in a distressed market.

Leading with Truth in a World Full of Denial

Bernadette isn’t your typical broker. She doesn’t sugarcoat. She doesn’t let clients dream themselves into foreclosure. And she sure as hell doesn’t avoid the hard questions:

“Don’t try to be a hero and let me deal with the bank. Be honest. Let’s solve this together.”

That mindset has made her one of the most trusted brokers in New York’s luxury commercial market — and a go-to partner for lawyers handling distressed assets.

Distress Is the New Normal

From post-COVID defaults to overleveraged investors, Bernadette breaks down why brokers who ignore distress are setting their clients up to fail.

She tells the story of a $60M listing that should’ve gone to market at $40M.

The result?

A full year of price reductions — and finally selling at the exact price she predicted in month one.

All because ego delayed action.

“Appraise Your Greed”

Leo shares a brutal anecdote: a billion-dollar building now worth just $45M after injecting $150M in equity. Why?

“Because he couldn’t afford to pay his ex-wife’s bills anymore. That’s when he finally appraised his greed.”

Real estate isn’t just about bricks and ROI. It’s about relationships, reputation, and sometimes — ruin. This episode unpacks how personal obligations and emotional legacy shape decisions more than numbers ever could.

When Emotion Enters the Room, Logic Exits

From estate litigation between siblings to sellers who refuse to acknowledge debt, the stories here are raw and very real.

Bernadette reveals how she acts as a neutral third-party liaison to help emotionally entangled families, bitter partners, and overwhelmed landlords come to terms — and move forward.

“Sometimes your job isn’t just selling the building. It’s restoring enough trust for a transaction to even happen.”

This Market Rewards Urgency — Not Over-Penciling

Bernadette’s final message?

“While you’re over-underwriting, someone else is buying. This is our moment — for us, for our families, for generational wealth.”

🎧 Watch the full episode now for a rare, behind-the-scenes look at the role of emotional intelligence in commercial real estate.

If you're dealing with default, ego, or indecision — this is the perspective shift you didn’t know you needed.

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