Adam Sherman on Strategy, Risk & Litigation Discipline | JPC Podcast Ep 9
Jacobs P.C.
From Loose to Laser-Focused
Adam Sherman didn’t always have it all figured out.
He didn’t grow up dreaming of commercial litigation. He didn’t ace his law school classes with ease. And he certainly didn’t plan to become the “tightest” writer in the room.
But in Episode 9 of Confronting the Impossible, Adam shares how each stage - from the Upper East Side to Hofstra Law to the courtrooms of New York - built the person and professional he is today.
Early Days, Unclear Paths
Adam’s path into law started with inspiration from his grandfather, a respected trial attorney who commanded family gatherings with poise and presence. But that inspiration didn’t come with a roadmap. Law school felt rigid. Grades were confusing. Career direction? Arbitrary.
“I didn’t love it,” Adam admits. “But I knew I had to finish.”
Mentorship that Reshaped a Mindset
It wasn’t until he started practicing that Adam began to understand the law’s real impact. Working at a boutique firm, he was mentored by two radically different attorneys:
- One taught him how to morph into the client, prioritizing business goals over legal dogma.
- The other trained him in high-level precision, ripping his writing apart and rebuilding it line by line with a litigator’s discipline.
Their contrasting styles forced Adam to find his own balance: strategic like a chess master, but never afraid to throw a punch when the game called for it.
Litigation as Chess — and Street Fight
“Not everything is won in a courtroom,” Adam says. “Sometimes you need to move outside the rules - or outside the ring.”
He views every case as a chessboard:
- Strategy over speed
- Pattern recognition over panic
- Risk-taking when the position demands it
But he’s not all theory. There’s a brawler in there too - one who knows when to walk into a mediation and flip the leverage, or use off-the-board tactics like bringing in a buyer or filing bankruptcy to change the entire legal equation.
Tightened by Training, Driven by Results
After years of training under his second mentor - a Skadden-trained partner with an eye for microscopic legal detail - Adam tightened his discipline to an elite level.
And it paid off.
“I thought we were going to lose. But because we tightened everything - structure, detail, arguments - we didn’t just avoid losing. We won.”
Still, that success came at a personal cost: “My enjoyment plummeted. But my impact skyrocketed.”
The Chess Master’s Game-plan
Today at Jacobs P.C., Adam combines the best of both worlds:
- Creative leverage tactics from his early days
- High-level writing discipline from his mentors
- A strategic mindset forged by competitive chess - his childhood passion
Whether in a courtroom, a boardroom, or a mediation, Adam now sees his role as that of a chess master:
- Sometimes directing the client like a coach
- Sometimes moving the pieces himself
- Always thinking five steps ahead
Final Thought
Adam’s story isn’t just about law. It’s about the internal shift that separates good from great.
To confront the impossible, he didn’t need to be born brilliant. He needed clarity, discipline, and mentors willing to push him to the edge of discomfort - so he could return stronger, sharper, and always a few moves ahead.
This episode is a masterclass in how self-awareness, rigorous training, and mental patterning shape top-tier legal strategy - and why every courtroom is a chessboard.
🎧 Watch Episode 9 now
The Chess Master – Adam Sherman on Confronting the Impossible
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
