Real Estate Investing with RealDealCrew

AI for Small Business Owners: 20 Hours a Week of Testing w/ Brent Stewart

September 19, 2026·36 min
Episode Description from the Publisher

Brent Stewart spent 20 hours a week for four months testing AI, and says refusing to use it is the real liability.Brent Stewart has practiced law for 30 years in Rock Hill, South Carolina, fighting insurance companies as a trial lawyer. He also owns the office buildings his own firm rents. Over the last four months he set aside 20 hours a week to work through every legal AI system he could find, and he came out of it with a position most people do not expect from an attorney: the people refusing to learn these tools are the ones creating exposure, for their clients and for their employer.This conversation gets into what he actually built, what it cost him, and what he got wrong first. He walks through why his AI is walled off from the open internet, the vendor contract structure he now insists on, and the mistake that cost him thousands of dollars before it taught him anything useful.On the real estate side, Brent bought his office buildings through a separate entity that rents to the law firm, then restructured ownership so his wife qualifies as active manager. That change let him run the losses against his law firm income instead of depreciating remodels slowly over time.What you will learn:Why he keeps his AI in-house and never lets it pull case law off the open internetThe AI vendor contract he recommends: lock the price for three years, keep a one-year outHow a 10 percent ownership change and active manager status unlocked accelerated depreciationWhy he tells his AI to argue with him instead of agreeing with himHow he can now spot which opposing counsel are using AI, just from how fast discovery comes backAbout the guest: Brent Stewart is the founder of Stewart Law Offices, a personal injury and workers' compensation firm he started in 1995 after running a market study to pick his location. He graduated law school in 1989 and still keeps every deadline in a paper calendar.Links:🔗 Brent Stewart: https://StewartLawOffices.net📞 866-STEWART🔗 Build systems for your investing business: https://realdealcrew.com#RealEstateInvesting #AIForBusiness #LegalTech #AIAutomation #RealDealChat #CommercialRealEstate #AcceleratedDepreciation #BusinessSystems #RealEstateTax #SmallBusinessOwner #AITools #LawFirmManagement #EntrepreneurshipWork With RealDealCrewIf you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:Take the Deal Intake AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotifyAmazon MusicFacebookTwitterInstagram

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