Vetting AI for Law Firms, Drunk Business Advice & Celebrity Shenanigans (Feat. Kristin Kenzy)

Oct 3, 2025

Kristin Kenzy, creator of the Drunk Business Advice newsletter and a former commercial real estate professional, joins the conversation to share her unique journey into media. She reveals the importance of learning from failures and how her personal anecdotes shaped her writing cohorts. Amid laughs, Kristin delves into bizarre networking experiences, including a neighbor's odd pitch for a sex toy pyramid scheme. Plus, she showcases her celebrity trivia prowess in a fun drinking stories quiz!

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ADVICE

Three-Part AI Vetting Strategy

Vet AI in three parts: data-security/regulatory fit, AI-specific risks, and practical operational controls.
Review laws (HIPAA), state rules, ethics opinions, SLAs, opt-out of model training, and enable MFA and memory controls before use.

ADVICE

Prioritize Legal And Ethics Requirements

Check federal and state data laws and your jurisdiction's ethics opinions when evaluating cloud or AI vendors.
Your duty is reasonable safeguards, not a guarantee against breaches, tailored to firm size and scope.

INSIGHT

AI Adds Unclear Confidentiality Risks

AI introduces new vetting layers beyond traditional cloud questions, especially around model interaction and training.
Many interactions between client data and LLMs remain poorly understood and require updated bar guidance.

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Jared Correia and special guest Kristin Kenzy, the voice behind Drunk Business Advice, are here to discuss everything from AI vetting to celebrity drinking stories.

First, Jared shares his monologue answering a crucial question: "How do law firms vet AI tools?" He breaks down a three-part strategy, covering data security, AI-specific risks, and practical usage, and references helpful ethics opinions like DC's Opinion 388. Jared also bluntly notes that lawyers shouldn't worry about hallucinations, as they should be checking AI output anyway.

Then, Kristin Kenzy explains the origin of her Drunk Business Advice brand. She tells the story of her career change from commercial real estate, where she learned that success is often based on "mistake-driven lessons" and being willing to talk about your "f***ups." She also shares a bizarre story of a suburban neighbor trying to recruit her into a sex toy pyramid scheme.

Finally, stick around for our Counter Program segment, "Drunken Shenanigans Advice." Kristin is tested on her knowledge of celebrity drinking stories, including Jennifer Lawrence puking on Madonna's porch and Robert Downey Jr. passing out naked in a neighbor's bed. She even gets a bonus question about which band was named after a "steam-powered dildo."

Learn more about Kristin at KristinKenzy.com
Watch the show on our YouTube channel.
And check out this week's Spotify playlist.

Thanks to those supporting this episode:

Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.
Captain Compliance. Visit captaincompliance.com to easily manage your company's privacy compliance.
Attorney at Work. Head to Attorney at Work for your one really good idea each day. Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.

(00:00) - Intro & Jared's Monologue: How to Vet AI
(01:28) - Vetting AI: The Three-Part Strategy
(02:31) - Ethics Opinions & Data Security Questions
(03:31) - AI-Specific Questions: LLM, Data Training & RAG Systems
(05:32) - Why You Don't Need to Vet for Hallucinations
(07:49) - Introducing Guest: Kristin Kenzy of Drunk Business Advice
(09:22) - Kristin's "Chaotic" Background & Stealth Mastermind
(11:21) - The Origin of Drunk Business Advice
(14:39) - Lawyers' "Bullsh*t Stories" as a Business Model
(15:06) - The "Fuck This" Career Change: A Story of Redefining Wealth
(19:03) - Jared's Hatred of Business Books & The Power of Narrative
(23:01) - Kristin's Favorite Novel as a "Business Book": Ragtime
(24:21) - Bizarre Networking & a Sex Toy Pyramid Scheme
(28:54) - Logistically, How to Make a Career Change
(32:19) - Counter Program Intro: "Drunken Shenanigans Advice"
(44:57) - Conclusion & Outro

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