What does it really mean to “go to litigation”?

Litigation Isn’t the Fire — It’s the Fire Escape: Lessons from Adam Sherman

According to Adam Sherman — head of the Business Litigation department at Jacobs PC — if you’re asking that question, you’re probably already in it.

In this episode of Confronting the Impossible, Leo Jacobs sits down with Adam Sherman for a candid, brutal, and eye-opening look into the high-stakes world of real estate and business litigation. From saving billion-dollar portfolios to exposing dangerous deals — this episode unpacks the mindset and strategy it takes to survive (and win) in court.

You’re Already in Litigation — You Just Don’t Know It

One of Adam’s core messages is deceptively simple:

"You're in litigation the moment there's a semi-serious disagreement."

Most business owners think litigation starts when they get served. But as Adam explains, the posture and paper trail months before a lawsuit are what ultimately shape the outcome. In one major case, Adam reviewed months of transactional emails and spotted the beginning of litigation long before court papers were filed.

His advice? Get litigators involved early — before the bleeding starts.

The Billion-Dollar Client Who Dodged a Collapse

In one of the most powerful stories, Adam recounts a client with an $8 billion portfolio. When 20% of that portfolio fell into distress, he was slammed with receivership motions and orders to show cause.

Because he came to Jacobs PC early, Adam and the team stalled the receivership for 10 months — enough time to stabilize the property and regain leverage.

“We turned a cardiac arrest into a clean discharge in two months,” Adam says.

The Real Cost of a Bad Deal

Transactional attorneys don’t escape scrutiny here. Adam pulls no punches:

“These guys want to close the deal, so they push, push, push — until they push the client off a cliff.”

In one chilling example, a client was shocked to find out he had signed a full personal guarantee on a multimillion-dollar deal. He had no idea. When the team printed and highlighted the documents, his first reaction was:

“I didn’t sign that.”

But he had.

Litigation Isn’t a Waste — It’s Leverage

Adam calls litigation an economic strategy, not a last resort. Waiting too long costs more. Acting early can mean negotiating better terms, stalling enforcement, or flipping the power dynamic.

“We’ve had default interest waived for years, simply because we knew when to push and how.”

From the Emergency Room of Business Law

Adam compares the Jacobs PC litigation team to trauma surgeons. Most clients come in asking for help with a single problem — but they’re already in multi-organ failure.

“You think you’ve got a sprained ankle, but we see a heart attack on the way.”

They don’t do patchwork. They go macro. And they’ve advised on over $5 billion in distressed assets in just the past 27 months.

The Style? Hyper-Aggressive. Always Strategic.

Adam wraps the conversation with his litigation philosophy:

“Punches are flying in this market. If you don’t punch back, you’ll get hit.”

His strategy is about timing — knowing when to be aggressive, when to posture, and when to negotiate. But one thing’s clear: in today’s market, inaction is a death sentence.

🎧 Watch the full episode for real stories, raw strategy, and a behind-the-scenes look at how real estate litigation works at the highest level.

If you’re in business, you’re already in the ring. Make sure you know how to fight.

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