The Endeavors AI Podcast

Collin McKee

The Endeavors AI Podcast explores how law firms and professional services businesses are navigating the AI revolution — what's working, what's not, and where the real opportunities are. Host Collin McKee, founder of Endeavors AI, sits down with attorneys, entrepreneurs, and operators to cut through the hype and get practical about what AI actually looks like in day-to-day practice.

  1. Oct 23

    Your Client's ChatGPT Chats Aren't Privileged: A Former Federal Enforcer Explains

    Anything your client types into ChatGPT is not privileged, and it can be discoverable in litigation. Dennis Sapien-Pangindian, Founding Attorney of DSP Advocates, P.C. in New York, started his career enforcing federal healthcare fraud laws at the HHS Office of Inspector General, then worked at Paul Hastings and as Senior Counsel at Epstein Becker Green before opening his own firm in 2025. Host Collin McKee and Dennis talk about why he moved from the billable hour to flat fees, how AI-assisted research in Clio Work cut a full day of legal research to an hour or two, why he treats AI like a summer associate he doesn't fully trust yet, and the AI phone agent and lead-scraping tools he tried and dropped. Dennis also explains why clients' AI chats aren't protected, how to talk with clients who fact-check their lawyer with ChatGPT, and the one AI step every small-firm lawyer should take this week. Chapters: 00:00 Intro: Dennis Sapien-Pangindian, DSP Advocates 01:00 Why start in government at HHS-OIG 02:48 The False Claims Act and healthcare fraud 04:30 Switching sides: from enforcer to defense counsel 06:03 Why he left Big Law to start a firm of one 07:45 Billable hour vs. flat fees 10:47 How AI makes flat fees profitable (Clio Work) 13:46 AI tools that failed: AI receptionist and lead scraping 16:59 White glove, not a metal hand 19:00 Your client's ChatGPT chats aren't privileged 21:22 When clients fact-check their lawyer with ChatGPT 23:38 Do this week: run an AI audit 24:19 Where AI in legal practice goes in the next two years 25:43 Where to find Dennis and DSP Advocates Dennis Sapien-Pangindian / DSP Advocates: https://www.dspadvocates.com Dennis on LinkedIn: https://www.linkedin.com/in/dsapienpangindian/ Endeavors AI: https://www.endeavorsai.com Educational only, not legal advice.

  2. Sep 23

    AI Does 35% of the Work. The Attorney Owes the Other 65%. | Kent Grover & Robert Young IV

    Kent Grover and Robert Young IV of Elite Legal Strategy join Collin McKee to break down outside general counsel: where it sits between in-house lawyers and litigation counsel, why the membership model works, and the revenue point where a company actually needs in-house counsel. Robert also walks through where AI goes wrong in legal practice, from hallucinated contract terms to case citations that drift after repeated edits, and why the attorney still owns the final 65%. Full transcript and show notes: https://www.endeavorsai.com/podcast/kent-grover-robert-young-elite-legal-strategy

  3. Sep 23

    Small Law Firms Finally Have the Edge, If They Don't Blow It | Keith Conrad

    Keith Conrad, founder of Verbatim Legal Operations, on why small law firms now have the edge over Big Law, why deploying AI is a hiring decision rather than a software upgrade, and the current state analysis every firm should complete before touching a single tool. Full transcript and show notes: https://www.endeavorsai.com/podcast/keith-conrad-verbatim-legal

  4. Sep 23

    A Ban Is Not an AI Policy: What Gets Law Firms Sanctioned | Jeff Cunningham

    Legal ethics and malpractice defense attorney Jeff Cunningham on AI-generated bar grievances, prompt injection in court filings, why a blanket ban is not an AI use policy, and what every small firm should put in writing this week. Full transcript and show notes: https://www.endeavorsai.com/podcast/jeff-cunningham-cohen-cunningham

  5. Sep 23

    How a 15-Person Law Firm Actually Uses AI (And Where It Failed) | John Phebus

    John Phebus, founding attorney of The Law Offices of John Phebus in metro Phoenix, on running a 15-person personal injury and criminal defense firm on AI every day — the scheduled tasks, the lien tracker, the exhibit prep — and the time AI misread a lab report and built a whole section of an expert report on the wrong number. Full transcript and show notes: https://www.endeavorsai.com/podcast/john-phebus-crime-injury-law

  6. Sep 23

    Don't Use AI vs. Don't Use That AI — A Law Firm Partner Explains | Shirin Adelman

    Shirin Adelman, partner at healthcare law firm Lengea Law, on why the real AI risk for med spas, dental, veterinary and wellness clinics isn't using AI — it's using the wrong platform with protected patient health information, and what compliant adoption looks like. Full transcript and show notes: https://www.endeavorsai.com/podcast/shirin-adelman-lengea-law

  7. Sep 23

    Your AI Chat History Is Discoverable in Court | Jennie Woltz

    Employment attorney Jennie Woltz of Woltz & Folkinshteyn, P.C. explains why AI chat histories are not protected by attorney-client privilege, where AI is already creating liability inside HR teams, and what belongs in an AI acceptable use policy. Full transcript and show notes: https://www.endeavorsai.com/podcast/jennie-woltz-wfpc-law

  8. Sep 23

    AI Can Do 90% of Legal Work — Where Your Firm Has to Stop | Ryan Walker

    Ryan Walker built CoCounsel as CTO of Casetext before Thomson Reuters acquired it for $650 million — then left software to co-found General Legal, an AI-native law firm. He explains exactly where AI falls short, what it means for junior associates, and how a small firm should sequence adoption. Full transcript and show notes: https://www.endeavorsai.com/podcast/ryan-walker-general-legal

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About

The Endeavors AI Podcast explores how law firms and professional services businesses are navigating the AI revolution — what's working, what's not, and where the real opportunities are. Host Collin McKee, founder of Endeavors AI, sits down with attorneys, entrepreneurs, and operators to cut through the hype and get practical about what AI actually looks like in day-to-day practice.

Information

  • Creator
    Collin McKee
  • Years Active
    2026
  • Episodes
    29
  • Rating
    Explicit
  • Copyright
    © 2026 Collin McKee
  • Show Website
    The Endeavors AI Podcast