Serious AI with Chris Duff

Chris Duff
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Enterprise AI, built on camera. Live builds, what they cost to get right, and the parts that did not work. Three kinds of episode: builds put together on screen with the reasoning out loud, diagnostics on problems operators are actually carrying, and the running account of what we are building now and the calls we got wrong. Hosted by Chris Duff, who builds AI systems for operators carrying real financial consequence and spent years being one. Most AI consultants have never had a dollar at risk. Not one. Serious means underwritten. seriousai.partners

  1. 2d ago

    Every 10 minutes, my AI fed me questions to ask the room | Ep 328

    At the MGMA Annual Conference (the Medical Group Management Association's yearly meeting for people who run medical practices) in San Antonio, I ran Claude Code against my live Notion meeting transcripts, and every 10 minutes it suggested what to ask next. This screen-share walks through the whole setup: picking 18 sessions before the trip, a glossary of revenue cycle jargon built as the speakers talked, a field log that caught 10 healthcare opportunities, and what broke when my laptop battery couldn't keep up. I walked in knowing nobody in practice management and left with a plan for every follow-up. Take any piece of it for your next event. AI for medical groups and practices:https://seriousai.partners/healthcare/?utm_source=podcast&utm_medium=description&utm_content=ep-328-ai-conference-questions Serious AI News, every Monday. AI for operators, what we built and what it cost:https://seriousai.partners/newsletter/?utm_source=podcast&utm_medium=description&utm_content=ep-328-ai-conference-questions Tell us what's breaking:https://seriousai.partners/contact/?utm_source=podcast&utm_medium=description&utm_content=ep-328-ai-conference-questions Chapters:0:00 Every 10 minutes, my MacBook told me what to ask1:46 Why a healthcare conference2:34 Picking 18 sessions with Claude before the trip5:37 The first session, a fire hose of jargon7:33 Long Claude Code threads hold up now10:21 Live questions every 10 minutes11:38 Why I never asked a question13:33 A running glossary, built live14:57 Composio and more than one Google account17:14 What Claude can't see in the room18:27 The routine Claude built for itself20:10 The battery problem and the phone workaround23:43 Slides in, field log out24:21 Lessons, fewer sessions and more meetings25:35 Was I the agent?28:49 Why I'd never skip this setup again #ClaudeCode #HealthcareAI #AIForBusiness #AIAgents #ConferenceStrategy

  2. Oct 2

    Your payer can underpay you without a single denial | Ep 327

    I spent two and a half days at MGMA 2026, the national conference for medical group leaders, as an AI builder with a medical background who went there to learn. What I found is a blind-spot triangle: are you paid what your contracts say, is your AI's work right, and does anyone own the whole picture across the tools you bought one at a time. Payers already use AI to deny claims and quietly downcode them, and many of the practices in those rooms are still answering by hand. Take one question back this week: for an AI tool you pay for, what single number would prove it's working? AI for medical groups and practices:https://seriousai.partners/healthcare/?utm_source=podcast&utm_medium=description&utm_content=ep-327-underpaid-no-denial Serious AI News, every Monday. AI for operators, what we built and what it cost:https://seriousai.partners/newsletter/?utm_source=podcast&utm_medium=description&utm_content=ep-327-underpaid-no-denial Tell us what's breaking:https://seriousai.partners/contact/?utm_source=podcast&utm_medium=description&utm_content=ep-327-underpaid-no-denial Chapters:0:00 Buying AI one tool at a time0:16 MGMA 2026, going in to learn2:50 AI in every room, and the pressure on operators4:21 Point tools and ambient scribes5:36 Only a few run a mature AI program6:57 Payers already automate denials8:16 Why the buying decisions are happening now9:50 The blind-spot triangle12:26 In-house build versus vendor tools14:33 Silent downcoding, billed one code and paid another15:45 Contracts that pay less than they say17:09 A scribe that ignored its rules18:10 Coders still checking by hand19:11 The human side of automation20:20 Who owns the whole picture21:51 Your move, name one number #HealthcareAI #MedicalPractice #RevenueCycle #AIImplementation #EnterpriseAI

  3. Sep 25

    My plan to turn a $2,400 ticket into a $2M pipeline | Ep 326

    Two days after picking healthcare as the focus for Serious AI, I bought a $2,400 ticket to the MGMA annual conference in San Antonio. Before the trip I had Claude research every speaker and all 171 exhibitors, narrow more than 100 organizations to 14 targets, and build each one a short, specific read on where AI could help their practice. This episode walks through the whole plan: why healthcare, how the pain points were checked before anything shipped, and why the uncomfortable choice was the right one. AI for medical groups and practices: https://seriousai.partners/healthcare/?utm_source=podcast&utm_medium=description&utm_content=ep-326-2m-pipeline Serious AI News, every Monday. AI for operators, what we built and what it cost: https://seriousai.partners/newsletter/?utm_source=podcast&utm_medium=description&utm_content=ep-326-2m-pipeline Tell us what's breaking: https://seriousai.partners/contact/?utm_source=podcast&utm_medium=description&utm_content=ep-326-2m-pipeline Chapters: 0:00 A $2,400 conference ticket 0:41 A wide band and no vertical 2:44 Why healthcare 5:47 A healthcare page in a day 8:24 Checking the pain points before they ship 9:25 The Ask Method, rebuilt with AI 11:02 Retargeting AI search around healthcare 11:52 Conferences and the hiring signal 14:06 MGMA, this weekend in San Antonio 17:36 Choosing the uncomfortable option 19:47 Researching every speaker before the trip 21:35 Artifacts that show the work first 22:36 14 targets and the host organization 25:27 The Tim Ferriss playbook 26:46 What's next #HealthcareAI #MedicalPractice #AIImplementation #FractionalHeadOfAI #ClaudeCode

  4. Sep 18

    AI wrote my FAQ. I rewrote 17 of 20. | Ep 325

    Seven days to move a business from one brand to another. DNS, a full website, SEO, the podcast routines, every description and every link, and Claude Code ran the whole thing on barely 10% of a week's usage on Claude Max. It still wrote an FAQ where 17 of 20 answers had to be rewritten by hand. AI output sounds equally smart whether it is correct or wrong, and if you have not decided what your company stands for, you have no way to tell which one you are reading. Serious AI News, every Monday. AI for operators, what we built and what it cost: https://seriousai.partners/newsletter/?utm_source=podcast&utm_medium=description&utm_content=ep325 Tell us what's breaking: https://seriousai.partners/contact/?utm_source=podcast&utm_medium=description&utm_content=ep325 Chapters: 0:00 The rename, and going full time on enterprise AI 1:58 Cadence, and what carries over from the old show 6:11 Where the show goes next, live builds and demos 9:01 Being up front about the commercial incentive 9:30 No business I have met is fully AI optimized 11:57 Seven days to stand up a company 15:48 The infrastructure work that used to need a contractor 18:31 Why starting anything new costs more than it looks 22:11 Where the models stop being useful 23:38 Polsia, a $10M run rate with one-star reviews 25:52 17 of 20 FAQ answers had to be rewritten 28:16 Brand first, or chase customers first 30:12 The routine that removes the human from publishing 32:35 Where my judgment overrides the model

  5. Aug 26

    Claude Code Built My Entire Product Launch in 24 Hours | Ep 324

    The SLC Deal Engine is live and Claude Code handled nearly the entire launch. Chris breaks down how the AI land underwriting tool went from production-ready to publicly for sale in a single day: structuring the offer around Alex Hormozi's value equation, filming a side-by-side race between his manual underwriting and the Deal Engine as the core proof point, and letting Claude Code cut 90 minutes of raw footage into a 20-minute branded video sales letter then build the sales page, payments, and install funnel to match. Work that used to take weeks now ships in a day. Watch the Deal Engine race Chris's manual review Land funding AI implementation for your business #seriouslandcapital #claudecode #landinvesting #aiautomation #productlaunch

  6. Aug 20

    More Instructions Won't Make Your AI Reliable | Ep 323

    In this episode, the SLC Deal Engine emerges from a two year, $100K rebuild that ran through Land Pricer, SLC Chat, and a Cowork plugin that kept breaking under its own patches. The breakthrough came from scrapping vibe coded architecture entirely and rewriting the underwriting procedure as hard code, reserving AI only for final pricing judgment. The finished engine runs in roughly an hour at about 2% of weekly token usage on a $200 Claude Max plan. Update, September 2026: the Deal Engine is no longer offered for install. It runs inside Serious Land Capital's own deal review.WORK WITH USLand operators: submit your deal for funding at seriousland.capital. We've funded over $6.5M with 41% operating margins, checks from $50K, and we close what we commit to.AI implementation: I build workflows for companies collectively doing over $50M in annual revenue and take on a small number of clients. Reach out directly.Seeing something different in your market? Drop it in the comments with a source. I'll read every one.Get our exclusive weekly newsletter every Monday at Serious News.Deal breakdowns, AI for operators, behind-the-fund decisions.Operator-to-operator. No fluff.→ ⁠https://seriousland.capital/newsletter/⁠#seriouslandcapital #aiforbusiness #vibecoding #landinvesting #getseriouspodcast

  7. Aug 12

    Most AI Consultants Have Never Had a Dollar at Risk | Ep 322

    In this episode, the Serious brand gets rebuilt end to end using Ryan Levesque's Category of One framework, landing on one line: serious means underwritten, and we fund what we underwrite. The core thesis is that AI is crashing the price of everything copyable, so value migrates to what it cannot print (physical scarcity and human trust). The company now runs two arms under one brand: capital deployment into land, and boutique AI implementation for established businesses.WORK WITH USLand operators: submit your deal for funding at seriousland.capital. We've funded over $6.5M with 41% operating margins, checks from $50K, and we close what we commit to.AI implementation: I build workflows for companies collectively doing over $50M in annual revenue and take on a small number of clients. Reach out directly.Seeing something different in your market? Drop it in the comments with a source. I'll read every one.Get our exclusive weekly newsletter every Monday at Serious News.Deal breakdowns, AI for operators, behind-the-fund decisions.Operator-to-operator. No fluff.→ ⁠https://seriousland.capital/newsletter/⁠#seriouslandcapital #landinvesting #AIimplementation #skininthegame #realestateinvesting

  8. Aug 5

    I Used AI to Fact-Check Reventure's Housing Crash Video | Ep 321

    Reventure published "WSJ drops major warning. Six-figure losses emerge." on July 27, calling this a housing depression. I ran his five core claims through a fact-check system and pulled the primary data on each one. Three of them don't hold up the way they were presented.The video I'm responding to: https://www.youtube.com/watch?v=NstJsXpTOlk WORK WITH USLand operators: submit your deal for funding at seriousland.capital. We've funded over $6.5M with 41% operating margins, checks from $50K, and we close what we commit to. AI implementation: I build workflows for companies collectively doing over $50M in annual revenue and take on a small number of clients. Reach out directly. Seeing something different in your market? Drop it in the comments with a source. I'll read every one. Get our exclusive weekly newsletter every Monday at Serious News. Deal breakdowns, AI for operators, behind-the-fund decisions.Operator-to-operator. No fluff.→ https://seriousland.capital/newsletter/

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Enterprise AI, built on camera. Live builds, what they cost to get right, and the parts that did not work. Three kinds of episode: builds put together on screen with the reasoning out loud, diagnostics on problems operators are actually carrying, and the running account of what we are building now and the calls we got wrong. Hosted by Chris Duff, who builds AI systems for operators carrying real financial consequence and spent years being one. Most AI consultants have never had a dollar at risk. Not one. Serious means underwritten. seriousai.partners

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