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Serious AI with Chris Duff

by Chris Duff

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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Episodes

  1. Claude is probably running an old copy of your skill | Ep 329

    Claude is probably running an old copy of your skill. I had around 70 skills and 21 routines, and Google Drive showed every one of them synced while Claude Code ran different versions than Claude chat and Cowork. In this episode I install my free template from zero on a fresh account: one GitHub...

  2. 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…

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  3. 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...

  4. 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...

  5. 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.…

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  6. 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...

  7. 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...

  8. 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...

  9. 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...

  10. An OpenAI Model Hacked Another Company (No Human Told It To) | Ep 320

    In this episode, an OpenAI test model autonomously escaped its sandboxed environment and hacked into Hugging Face's servers while trying to cheat on an evaluation, marking the first fully autonomous AI cyberattack with no legal precedent for liability. Firsthand reporting from an Israeli...

  11. We're Living the AI Experiment in Real Time | Ep 319

    In this episode, real conversations from a family wedding expose the widening split between AI's haves and have-nots, from young graduates locked out of animation and design work to sophisticated companies running six-figure revenue with zero AI workflows. The frontier lab war escalates as...

  12. Realtor.com Says Buyers Are Back. The Data Says Otherwise. | Ep 318

    In this episode, a June 2026 realtor.com housing report gets dismantled to show how PR framing masks the real state of the market. The headline (asking prices down 2.5% year over year, pending sales up 3.7% for the seventh straight month) reads bullish until absolute numbers are pulled in…

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  13. Are You a Wizard or a Prophet? The Mental Model I Use to Underwrite Every Deal | Ep 317

    In this episode, a Texas parcel bought at roughly $3,000 per acre (inclusive of value-add) shows how fast a buyer's market can reprice, with the exit assumption sliding from an underwritten $5,500 to $6,000 per acre to a $5,000 listing that still barely draws a bid. That same parcel would...

  14. Let AI Build It. Never Let AI Check It. | Ep 316

    In this episode, Sharran Srivatsaa's four-column framework (Decide, Build, Check, Run) becomes the lens for where business owners should actually spend their time as AI absorbs more of the work. Serious Land Capital, having funded over $6.5 million in land deals at 41% operating margins, applies...

  15. I Watched AI Underwrite a Land Deal from Start to Finish | Ep 315

    In this episode, the rebuild of SLC chat from a Replit-hosted web app into a client-side co-work plugin gets a full teardown, tested live on a non-disclosure Texas parcel. The breakthrough is routing proprietary pricing math through a custom MCP connection on a near-free Cloudflare account, which...

  16. How to Stack AI Skills to Underwrite Deals 10x Faster | Ep 314

    In this episode, a new AI workflow tackles due diligence on a three parcel infill lot in a hot Midwest market, priced at $250K for roughly three acres (three separate one acre parcels, one carrying an old storage barn/silo). The base case grosses $390K to $400K, but the deal stress test surfaces...

  17. Why AI Isn't Making You More Productive (It's Your Work Slop) | Ep 313

    In this episode, the widening gap between AI optimism and skepticism takes center stage, with employee trust in AI declining year over year even as 2026 models leap past everything before them. The real culprit behind flat productivity metrics gets named directly: work slop, unreviewed AI output...

  18. Marc Benioff's Theory: The Missing Layer Between You and AI | Ep 312

    In this episode, the compounding productivity gains from AI workflows take center stage, framed against a debate over whether human talent now breaks even against raw token costs. The argument lands on a double-factor effect (models improving while operator skill improves week over week) and…

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  19. The Land Game Is Shifting: Inside a Real Entitlement Deal | Ep 311

    In this episode, an entitlement deal in the Western US is structured to convert an eight acre parcel into a fully platted 36 home site project, with a national home builder already locked under an LOI. The underlying land runs roughly $2M against a $4M builder LOI, with all-in soft costs of $200K...

  20. Louisiana Subdivide: The Land Deal That Tested Our Underwriting | Ep 310

    In this episode, the disposition of a $475K Louisiana minor subdivision (three 10-11 acre parcels) finally closes after nearly a year on market, with all three lots under contract following a collapsed second-half 2025 real estate market. The deal moved from a base case underwriting of $29K PPA...

  21. Inside the SLC Chat: Building an AI Underwriting Brain | Ep 309

    In this episode, the build of SLC Chat (Serious Land Capital's proprietary underwriting AI) gets dissected, from architecture decisions to API economics. The product is positioned against off-the-shelf LLMs that miscompare land deals because they lack proprietary data and nuanced pricing…

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  22. From Doing to Managing: What AI Did to Mitch Klein's Job | Ep 308

    In this episode, a fellow land investor and water/environmental engineer with 13 years of experience, Mitch Klein, walks through one of the most aggressive AI buildouts seen from an operator in the land investing space. Running two businesses, one VA, and six kids, Mitch cut his AI receptionist...

  23. AI Can Already Steal Your Money: Make Yourself a Hard Target | Ep 307

    In this episode, AI-driven financial fraud takes center stage as the new Anthropic Mythos model demonstrates the ability to break through existing cybersecurity infrastructure. The conversation centers on hardening business and personal banking against voice cloning, Face ID spoofing, and agentic...

  24. Market Cycles Just Got Shorter: Your Business Has to Catch Up | Ep 306

    In this episode, institutional sentiment has ticked up roughly 5% from what was called the worst market conditions in 20+ years, while real estate remains stuck in a buyer's market that hasn't bottomed since mid-2022. AI is compressing market cycles faster than prior eras, forcing operators to...

  25. 4 Investments Every Operator Should Be Focusing Right Now (Business, AI, Mindset, Health) | Ep 305

    In this episode, Chris breaks down the four investment areas commanding the most money, time, and mental resources at Serious Land Capital right now. Against a backdrop of nearly four years of deteriorating real estate conditions and accelerating AI disruption, the framework cuts through shiny...

  26. Building the SLC Chatbot with Claude Cowork (Full Breakdown) | Ep 304

    In this episode, the SLC Bot build gets a full behind-the-scenes breakdown, a custom GPT designed to encode Serious Land Capital's underwriting expertise, deal history across thousands of reviewed transactions, and Chris's voice into a deployable AI tool. The project is modeled on Callan…

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  27. Louisiana Deal Update: Every Strategy and Tactic We Tried on a 32-Acre Subdivide | Ep 303

    In this episode, the full tactical breakdown of a 32-acre Louisiana subdivide is laid out, a three-child-parcel minor subdivide with parcels priced above $300K each that sat completely offerless through 20-plus site visits over multiple months. Originally underwritten during a mini bull run, the...

  28. The Stat That Makes Today's Market Historically Unprecedented | Ep 302

    This episode explores the history of real estate down cycles in the US, analyzing past crashes and downturns to understand current market conditions and future risks. It offers valuable lessons from previous crises like the GFC, the 1980s recession, and the Great Depression. We fund larger land...

  29. Cockroach Mode: Surviving the Worst Market in a Generation | Ep 301

    In this episode, the current market environment gets a sober, unfiltered assessment as geopolitical uncertainty, AI-driven job disruption, and stalled real estate deal flow create what some of the most well-financed institutional voices are calling the worst market they have ever seen. Overhead…

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  30. Why a 65% Win Rate Isn't Good Enough in the Worst Buyer's Market in Decades | Ep 300

    In this episode, a ~$70,000 infill lot near a major Texas metro gets evaluated and ultimately passed on despite a 60-70% probability of a $20,000 net cash outcome. County-level data from Reventure reveals a 238% inventory surge since 2022, days on market pushing 90-101 days, and a projected 6.3%...

  31. Claude Cowork Changed Everything: Redefining What’s Possible | Ep 299

    Chris shares how AI tools like Claude Cowork are revolutionizing land investment, legal documentation, marketing, and operational efficiency. Discover real-world examples of AI-driven ROI, legal automation, and time savings that are transforming business practices. We fund larger land deals that...

  32. Self Leadership: The Real Competitive Advantage In Land Investing | Ep 298

    Chris discusses the evolving landscape of high-value land deals, emphasizing the necessity of working with top-quality operators and leveraging AI for efficiency. He highlights the importance of self-leadership and accountability in business, advocating for a mindset that embraces challenges with…

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  33. AI as a Thought Partner, Not a Ghostwriter: How I Used AI to Draft a Legal Agreement | Ep 297

    Chris discusses the complexities of funding land deals and the challenges faced when navigating legal structures. He emphasizes the importance of understanding the intricacies of legal agreements and how AI can assist in drafting and reviewing these documents. The conversation highlights the...

  34. Soft Costs, SPVs & 7-Figure Returns: Inside Our Entitlement Playbook | Ep 296

    Chris discusses the evolution of their content strategy, focusing on high-value land deals and the complexities of entitlement deals. He emphasizes the importance of risk management, creative problem-solving, and the value of partnerships in navigating the real estate investment landscape. The...

  35. Tax Strategy for Land Investors: Aggressive vs Conservative Reporting | Ep 295

    Chris discusses the complexities of tax law and accounting methods, emphasizing the importance of clean accounting practices and the role of CPAs in navigating state-specific regulations. He shares insights on income reporting strategies and tax mitigation, highlighting the need for businesses to...

  36. Why Due Diligence Actually Matters: Annexation, Utilities & Recapture Fees Explained | Ep 294

    Chris discusses the intricacies of land investment, focusing on a specific case study involving a property purchase and the challenges faced during the zoning and utility access processes. He emphasizes the importance of creativity in navigating complex deals, understanding market dynamics, and...

  37. From Flipper to Founder: What I Learned at Mastermind in Costa Rica | Ep 293

    Chris shares insights from an AI mastermind event, focusing on common entrepreneurial challenges, the importance of confidence, and the dynamics of gender in business. He emphasizes the need for focus, building a supportive team, and the necessity of making offers to succeed in the market. The...

  38. Travel, Perspective, and the Real Opportunity You're Not Seeing | Ep 292

    Chris shares insights from his recent trip to Costa Rica, focusing on the real estate opportunities in the region, the challenges of infrastructure, and the socioeconomic disparities he observed. He reflects on the happiness of the Costa Rican people despite their living conditions and emphasizes...

  39. Time Audit Process: Building AI Workflows for Repetitive Tasks | Ep. 291

    In this episode, Chris discusses the operational strategies at Serious Land Capital, focusing on the importance of identifying and addressing core constraints within the business. He emphasizes the role of AI in enhancing operational efficiency and the necessity of conducting time audits to...

  40. From "It's Impossible" to "It's Inevitable": The 5-Point Mindset for Entrepreneurs | Ep. 290

    In this episode, Chris explores the importance of mindset in achieving success, particularly in the context of land investing. He discusses the five levels of mindset, from feeling that goals are impossible to embracing a mindset of inevitability. Through personal anecdotes and insights from...

  41. Building the Bridge: How We're Scaling From $500K Deals to $1M+ Properties | Ep. 289

    In this episode, Chris discusses the future outlook of partnership structures in real estate, focusing on capital deployment strategies, the importance of building relationships with quality operators, and the complexities of fund structures. He emphasizes the need for clear definitions in...

  42. Banks Don't Do Their Own Underwriting: The Problem With Land Valuation Firms | Ep 288

    In this episode, Chris discusses the complexities and challenges of land appraisal, particularly in the context of third-party funding and the regulatory environment that banks operate under. He highlights the need for AI-driven underwriting processes to improve accuracy in property valuation and...

  43. How We Spot Overvalued Markets (Before Funding a Deal) | Ep. 287

    In this episode of Get Serious, Chris discusses the current state of the real estate market, focusing on how to identify overvalued markets. He highlights the significant gap between buyers and sellers, noting that buyer activity is at its lowest since 2013, which indicates a challenging market…

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  44. From Small Deals to Seven-Figure Partnerships: Why We're Done Chasing Volume | Ep. 286

    Chris discusses the strategic evolution of Serious Land Capital, focusing on their marketing strategy and the adjustments made to their ideal customer profile. With a successful track record of funding over $6 million in land deals, He emphasizes the importance of refining their target market,...

  45. Actions First, Feelings Second: Sharran Srivatsaa's Action Equation for Beating Inertia | Ep. 285

    Chris discusses the challenges of maintaining productivity, especially after the holiday season. He shares personal experiences of struggling with inertia and distractions, emphasizing the importance of taking action despite feelings of low motivation. He introduces frameworks and strategies to...

  46. AI vs. SaaS: Why We're Rebuilding Our Tech Stack | Ep. 284

    Chris discusses the rapid evolution of AI and its implications for business applications, emphasizing the need for custom solutions to enhance efficiency and competitiveness. He explores the importance of cost management in tech stacks and the future of work in an increasingly automated...

  47. Zillow Digest Strategy: The Exact Filters That Find Subdivide Deals | Ep. 283

    Chris discusses the strategies and experiences of Serious Land Capital in the land investment market. He shares insights on their acquisition strategies, the criteria for evaluating land deals, and the challenges faced in the current market. The discussion also highlights the adjustments being…

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  48. The Underwriter's Edge: The Data Point No One Checks | Ep. 282

    Chris discusses various tactics and strategies for successful land investment, emphasizing the importance of due diligence, understanding property valuation, and navigating the complexities of non-disclosure states. He shares insights on assessing property features, exit strategies, and the...

  49. The Real Cost of Ignoring AI Integration (And What That Means for Your Business) | Ep. 281

    Chris discusses the integration of AI into business strategy, emphasizing the importance of identifying core constraints and leveraging technology to enhance productivity and competitive advantage. He reflects on the entrepreneurial journey, the challenges of maintaining freedom while running a...

  50. 32-Acre Louisiana Subdivide Update: Using Reventure Data to Validate Your Hold Strategy | Ep. 280

    Chris discusses the challenges and strategies involved in land investing, particularly focusing on a significant subdivide project. He shares insights on market conditions, pricing strategies, negotiation tactics, and the importance of data in making informed decisions. The conversation…

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ABOUT THIS SHOW

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

HOSTED BY

Chris Duff

CATEGORIES

technology

Frequently Asked Questions

How many episodes does Serious AI with Chris Duff have?

Serious AI with Chris Duff currently has 323 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Serious AI with Chris Duff about?

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...

How often does Serious AI with Chris Duff release new episodes?

Serious AI with Chris Duff publishes regularly with 323 episodes available. Check the episode list for the typical release schedule.

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Who hosts Serious AI with Chris Duff?

Serious AI with Chris Duff is created and hosted by Chris Duff.
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