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Home > Podcasts > Devil's Advocate

Devil's Advocate

Welcome to hell. Devil’s Advocate pits lawyer against lawyer in a battle royale to answer the age old question: Who’s better at arguing. Let the depravity commence.

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Newest Episode

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Lawyer vs. Lawyer

Geoff Lowe vs. Stuart Rudner

03/05/2026

Lawyers Debate Influencer Culture, SEO Warfare & “Gravlune”

In this episode of Devil’s Advocate, Stuart Rudner and Geoff Lowe go head-to-head in a fast-paced debate on legal marketing, AI, and brand ethics. From influencer culture to bidding on competitor names, the conversation challenges how far firms should go to compete.

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Founder vs. Founder

Andrew Nasrinpay vs. Bobby Steinbach

12/05/2025

THE MOST HELLISH DEBATE

Hosted by Bobby and Andrew, this fiery episode of Devil’s Advocate takes chaos to a new level as the duo debates SEO, $15k websites, and whether law firm conferences are worth the hype—or just expensive excuses to socialize.

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Lawyer vs. Lawyer

Russell Knight vs. Rahul Iyer

11/07/2025

Lawyers DEBATE Divorce, S*X Work & Going VEGAN?!

What happens when two family lawyers are forced to argue the opposite of what they believe? In this episode of Devil’s Advocate, Chicago divorce attorneys Russell Knight and Rahul Iyer battle it out over everything from joint custody laws and mental health in divorce to sex work, veganism, and the mysterious concept of “floopery.”

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Lawyer vs. Lawyer

Rob Schenk vs. Will Smith

10/03/2025

Lawyers Debate Kanye, Taylor Swift, Movies, and NURSING HOMES?

In Episode 6 of Devil’s Advocate, Rob Schenk and Will Smith take the debate wheel for a showdown on everything from nursing home liability and AI in law to the value of a $15,000 website. Along the way, they spar over Taylor Swift vs. Kanye West, argue about fast food freedom, and invent a word you’ll never forget: “dravicular.”

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Lawyer vs. Lawyer

Adam Rossen vs. Derek Martin

09/05/2025

Should Lawyers be TikTok Famous?

South Florida heat meets Chicago grit! Adam Rossen and Derek Martin go head-to-head on burgers, censorship, TikTok lawyers, and the made-up word “plorish.” Heated, hilarious, and not your average legal debate.

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A promotional graphic for the Devils Advocate podcast shows John Richmond and Keith Vona in business attire, facing each other with a VS symbol between them, and a New Episode banner at the top. Flames border the bottom.

Partner vs. Partner

John Richmond vs. Keith Vona

08/01/2025

Law Partners Debate Everything

From plastic straw ethics to the future of law firm marketing, no topic is off-limits. It's sharp, hilarious, and just chaotic enough to be useful. Tune in for unexpected insight and a few questionable marketing strategies.

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Split image features Chris Dreyer and Bob Simon smiling in suits with a red VS and lightning bolt between them. Text reads Devils Advocate, New Episode, and flames border the bottom.

Lawyer vs. Marketer

Bob Simon vs. Chris Dreyer

07/04/2025

Who Wins the World’s WEIRDEST Debate?

Legal debates, business strategy, breakfast burritos—nothing is safe when Bob Simon and Chris Dreyer take opposite sides for sport. This episode of Devil’s Advocate is part improv, part insight, all entertainment.

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Two men are shown side by side on a red graphic with Ryan Makris and Ron Latz labeled below them, separated by a VS symbol. Devils Advocate and New Episode are written in the corners, with flames at the bottom.

Battle of the R's

Ron Latz vs. Ryan Makris

06/10/2025

Two Legal Marketers Debating OATMEAL and KANYE?!

Is justice just another line item on a spreadsheet? Will Google allow you to have a castle? If these questions don't make sense or sound interesting- you are in the right place! Welcome to another episode of Devil’s Advocate, where the only thing hotter than the debates are the takes themselves!

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Two men in suits, Erik Heninger and Morris Lilienthal, are pictured side by side with a VS graphic between them. The image promotes a new episode of the Devils Advocate podcast. Flames border the bottom.

Duelin' Dixie

Erik Heninger vs. Moris Lilienthal

05/02/2025

Lawyer vs. Lawyer | A Wheel Spins, Lawyers Debate, and “Dravish” Is Born

In our diabolical debut episode, two brave souls—Morris Lilienthal and Eric Henninger—step into the inferno. The catch? They’ve got to debate red-hot topics with one major twist: they’re arguing the opposite of what they actually believe. Chaos? Absolutely. Comedy? Obviously. Educational? ...Debatable.

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