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Jason Hennessey is no stranger to podcasts (he hosts one of his own)—though he’s not usually sipping bourbon while recording. A legal entrepreneur who literally wrote the book on SEO, Jason joins Bob and Mauro to trace his wild journey from military life to mastering the digital marketing game. They debate when you’re officially too old for YPO, revisit the dial-up days of early SEO, and even explore the seedy side of search—yes, we’re talking porn and casino marketing. No combat training required—just pour a glass and press play!

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Bob is joined by his favorite private eyes—and his longtime friends—Carlos and John Fernandez for a wild ride through the shadowy (and sometimes funny) world of private investigation. They dive into the brothers’ early days on the PI scene staking out the counterfeit handbag market and another truly bizarre case involving a missing set of tires that somehow ended up in Mexico. Mauro shares a legendary (and highly questionable) scam for sneaking into concerts, and, because it wouldn’t be a proper episode without it, he also takes a nap. Grab a glass—this is a fun one!

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This week on Bourbon of Proof, Bob and Mauro take on a bold challenge: can they convert tequila-loving trial lawyer Pratik Shah into a bourbon believer? Pratik brings the heat with insights on building a future-ready law firm, the evolving role of AI in legal tech, and what it’s like to run EsquireTek. They cover everything from high-level litigation strategy and state-to-state law quirks to—you guessed it—sleepovers at your parents’ house in your 40s. 

Oh, and did we mention Pratik is a founding member of Justice HQ AND a fellow Steelers fan?

This episode blends brains, booze, and a bold look at the future of law. Enjoy!

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In this episode of Bourbon of Proof, Open Jar’s Adam Warren pulls up a chair (and a few bottles of homegrown American whiskey) to chat with the guys about transforming lawyers into digital superstars. Covering everything from Adam’s game-changing advertising agency, to his children’s book A Bear with Pants, to the best chicken taco in Austin, TX, this episode is one wild ride. AND, Adam even gifts the guys with some swag that puts Mauro’s now infamous $3 tin of cookies to shame! Pour yourself a glass and press play—this one’s got flavor!

This ori-GIN-al episode of Bourbon of Proof swaps out bourbon for gin—but the spirit of the conversation is as bold as ever. Bob and Mauro trade sips and dive deep into the backstory of Steve Mehr, a true innovator who turned down high-paying job offers at a young age to forge his own path. Steve shares how he’s scaled his firms by obsessing over data, integrations, automations, and AI—leveraging legal-tech products specifically built for lawyers to transform the way legal services are delivered. From rebranding Sweet James to “winning the space” multiple times, Steve opens up about why he still feels like there’s something to prove, even at the top.

Twice named Ventura County Trial Lawyer of the Year (because once just wasn’t enough), Trevor Quirk joins the guys for a conversation that’s equal parts legal insight and community inspiration. Trevor’s racked up some seriously impressive verdicts in court, but what really sets him apart is his big heart and even bigger drive to make the world a better place. The crew tackles the myth of the so-called “nuclear verdict” and how defendants often had every chance to settle for far less. They also reminisce about the time Bob crashed at Trevor’s place during a trial — a week fueled by great whiskey, good strategy, and entirely too much Ben & Jerry’s.

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Step behind-the-scenes with two members of the Bourbon of Proof creative team: actor, producer, and social media legend Patrick Renna, and branding wizard and creative strategist Brandon Pearson from Studio 3 Marketing. Get an inside look at how they’re elevating performance marketing in the legal space through compelling storytelling and a top-tier creative approach. From boosting rankings and reach to building a trusted, results-driven team, Patrick and Brandon share actionable insights for anyone looking to make their mark with impactful, branded video content. Join us as the guys enjoy some incredible pours and dive deep into what it really takes to rise above the noise and stand out in a crowded market.

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Pop some Martinelli’s and settle in for a rare (gasp!) alcohol-free episode of Bourbon of Proof as we toast with the ever-inspiring Ibiere Seck! We talk humanity in law, her unmatched passion for trial work, and her Jedi-level insights on jury selection. Ibiere also tackles the age-old conundrum: Can you be an incredible trial lawyer, a terrific spouse, an amazing parent, a dedicated civil servant… and still make your bed in the morning? (Spoiler Alert: She’s probably doing all five before you’ve had your coffee.) From shaping legislation to mentoring the next generation of trial lawyers, Ibiere is all about IMPACT. If you like this, click subscribe, like and share with a friend.

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AI is not just for turning humanity into slave batteries used to power the CPUs of our computer overlords - it is used for the optimization and efficiency of your practices, providing your clients with streamlined service allowing your firm to scale to new heights. On this episode Host Bob Simon and Co-Host Mauro Fiore welcome Viraj Bindra of Finch Legal.

We delve into Viraj's origin story, he tells Bob and Mauro about how the lessons he learned regarding optimization and efficiency during his time at DoorDash are surprisingly applicable to his newest legal platform, and wow's them with his mixology skills, to quote Bob, "Holy s*** that's good." Cheers!