161: The BEST Career Advice From 25 Years As A Lawyer You'll Ever Hear | Jason Stuart Weiss

May 1, 2025

51:41

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There’s often a gap between what school teaches and what real life demands. Jason Weiss found that to be true for becoming a lawyer. Now, after 25 years in the legal world, he shares the practical, hard-earned lessons that apply to anyone trying to succeed in a high-pressure, people-driven profession.

Whether you’re a lawyer, leader, or someone simply figuring out how to show up fully in your work, this episode is a masterclass in resilience, communication, and redefining success on your own terms.

In this episode, you’ll learn:

Why “the practice of law” never really ends
How to recover from losses and develop thicker skin
What not to do when giving or receiving professional advice
How to pick clients (and when to walk away)
Why communication and follow-up might be your most valuable assets
The surprising ways AI and legal tech can (and can’t) help
When to rethink your entire career and how to do it responsibly

Timestamps:

00:16 – Jason’s post-law school “welcome to reality” moment

01:38 – First win in court and the difference real-world law makes

02:57 – Why law is a “practice” (and not an exact science)

03:58 – How a judge’s mood can influence your case

04:20 – Jason’s book: The Sht They Never Taught You in Law School*

05:54 – Universal skills: follow-up, integrity, and knowing your values

08:52 – Law school theory vs. real-world advocacy

11:25 – What happens when you lose and have to face the client

13:46 – Learning who not to work with as a lawyer (and business owner)

15:59 – The $60K mistake Jason made with a client—and what he learned

19:06 – Common misconceptions non-lawyers have about lawyers

21:25 – The power of saying “I don’t know”—and circling back

24:43 – Clients today expect instant clarity: managing modern expectations

25:55 – Thick skin, self-care, and knowing when not to take it personally

28:06 – Continuous learning, CLEs, and the role of AI in law

30:49 – Batman’s utility belt: how Jason views AI as a legal tool

33:43 – Worst professional advice Jason ever received

36:29 – Honesty, mistakes, and always having a plan of action

37:07 – Advice for those considering law school

38:35 – Why some lawyers are miserable—and how coaching can help

42:26 – What coaching is (and isn’t) supposed to do

44:23 – Finding motivation 25 years into the legal grind

45:35 – Why showing up is more powerful than talent

47:02 – You don’t have to respond instantly—just communicate well

47:46 – What Jason has doubled down on since writing his book

49:24 – Final advice for aspiring or struggling lawyers

50:14 – Where to find Jason online

About Jason:

Jason S. Weiss is a litigator who handles all aspects of business and commercial litigation. He has dealt with matters involving breach of contract, tortious interference with business relationships, title, property, non-compete clauses, commercial and residential landlord tenant matters, elder abuse, partnership disputes, trade secrets, RICO claims, fraud, real estate litigation, consumer protection, American’s with Disabilities litigation, tenant/landlord matters, medical marijuana litigation, personal injury and other various business related lawsuits.

He was recently appointed as a Board Member of Benefits Specialist Inc. and voted President of Leadership Coral Springs Class of 2011. Jason is also a former adjunct professor of Sports Law at Nova Southeastern School of Law, a former adjunct professor of the graduate level course Sports Law at St. Thomas University and a former judge for the Broward County Teen Court Program.

Jason has extensive sports and entertainment law experience, including representing professional football, baseball, and soccer players, personal management companies, rappers, bands, radio personalities, mixed martial arts fighters, chefs, agents, boxers, actors, writers and models. Jason has also negotiated, drafted and litigated recorded music and video deals, distribution agreements, publishing agreements, production agreements, employment contracts and endorsement deals for athletes, entertainers, musicians, chefs and agents. He serves as a legal advisor to professional athletes, performers and entertainers in all aspects of their professional and personal activities. Jason has been selected by Super Lawyer magazine as a Rising Star in 2009, 2010 and 2011.

Resources & Mentions:

- Jason’s Book: The Sh*t They Never Taught You in Law School : https://www.amazon.com/hit-They-Never-Taught-School/dp/1955242887