Chris Duff

Get Serious

Business EN ↓ 326 episodes

Join Chris Duff, Managing Partner at Serious Land Capital, as he shares short, value-packed episodes about his team's journey building a world class real estate business focused on land in the US. Succeed or fail, ALL will be shared. Occasional interviews may be published. Have a land deal that needs funding? Visit https://seriousland.capital/Want to price land more accurately and simpler than ever before? Visit https://landpricer.ai/

Be sure to visit the podcast's website and support the creator: seriousland.capital

Author

Chris Duff

Category

Business

Podcast website

seriousland.capital

Latest episode

Oct 28, 2026

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Episodes

I built a payer cost check. The worst payer wasn't the denier | Ep 331 28.10.2026

Most practices rank their payers by the monthly denial report, so the plan that denies the most gets the attention. I built a check on the 835 remits (the electronic statements that come back with every payment) to see what that ranking misses, using made-up sample data for a 24-clinician GI group. A payer costs you three ways: paid late, paid short, and paid by your staff's time chasing it. In th...

My best build got no feedback. A BAA post hit 9,400 impressions | Ep 330 23.10.2026

My best build got no feedback, and a LinkedIn post about a piece of healthcare paperwork hit 9,400 impressions (my posts usually draw 44 to 89). The paperwork is the BAA, the business associate agreement HIPAA requires before any vendor touches patient data, and the comment thread mapped three ways to keep that data safe with AI, plus the catches: you can't redact a voice, a BAA covers one vendor...

Claude is probably running an old copy of your skill | Ep 329 15.10.2026

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 repo that Claude Code, Claude chat and Cowork all update from, with Vale (a free style checker) blockin...

Every 10 minutes, my AI fed me questions to ask the room | Ep 328 09.10.2026

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...

Your payer can underpay you without a single denial | Ep 327 02.10.2026

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 downcod...

My plan to turn a $2,400 ticket into a $2M pipeline | Ep 326 25.09.2026

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,...

AI wrote my FAQ. I rewrote 17 of 20. | Ep 325 18.09.2026

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...

Claude Code Built My Entire Product Launch in 24 Hours | Ep 324 26.08.2026

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 minut...

More Instructions Won't Make Your AI Reliable | Ep 323 20.08.2026

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 abou...

Most AI Consultants Have Never Had a Dollar at Risk | Ep 322 12.08.2026

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...

I Used AI to Fact-Check Reventure's Housing Crash Video | Ep 321 05.08.2026

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 US Land operators: submit...

An OpenAI Model Hacked Another Company (No Human Told It To) | Ep 320 29.07.2026

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 cybersecurity firm with limited-license access to Claude Mythos shows the model surfacing an order of magni...

We're Living the AI Experiment in Real Time | Ep 319 23.07.2026

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 ChatGPT's 5.6 model now matches or beats Claude Fable at a lower price and offers one-click import of...

Realtor.com Says Buyers Are Back. The Data Says Otherwise. | Ep 318 15.07.2026

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: pending sales are sitting near GFC-era lows despite a materially larger US population. Active listings hit ro...

Are You a Wizard or a Prophet? The Mental Model I Use to Underwrite Every Deal | Ep 317 09.07.2026

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 underwrite closer to $4,000 per acre today, a 20% to 30% drop in under two months. Charles Mann's &quo...

Let AI Build It. Never Let AI Check It. | Ep 316 01.07.2026

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 the model to argue that owners belong in the Decide and Check columns while AI and systems handle B...

I Watched AI Underwrite a Land Deal from Start to Finish | Ep 315 25.06.2026

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 keeps the IP off the user's machine while shifting all AI token costs onto the end customer. This...

How to Stack AI Skills to Underwrite Deals 10x Faster | Ep 314 17.06.2026

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 utility red flags severe enough to threaten viability against a seller demanding a nine day close. We f...

Why AI Isn't Making You More Productive (It's Your Work Slop) | Ep 313 11.06.2026

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 that dumps the verification burden on the receiving party. Real-world proof points anchor the argument,...

Marc Benioff's Theory: The Missing Layer Between You and AI | Ep 312 03.06.2026

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 pulls in Mark Benioff's view that a middleware layer will soon sit between LLMs and end users to stop t...

The Land Game Is Shifting: Inside a Real Entitlement Deal | Ep 311 27.05.2026

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 to $300K. Serious Land Capital funds only the soft costs, tranched to milestones, in exchange for a 20...

Louisiana Subdivide: The Land Deal That Tested Our Underwriting | Ep 310 21.05.2026

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 down to fire-sale pricing, ultimately delivering a projected 1.17x net multiple to investors after aggre...

Inside the SLC Chat: Building an AI Underwriting Brain | Ep 309 13.05.2026

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 formulas. Total build cost came in around $60 and half a week of solo work. You can request an invite by em...

From Doing to Managing: What AI Did to Mitch Klein's Job | Ep 308 06.05.2026

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 cost from $250 to $3 per month while collapsing multi-day engineering deliverables into hours. The episo...

AI Can Already Steal Your Money: Make Yourself a Hard Target | Ep 307 29.04.2026

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 AI exploits, drawing on a recent strategy session with AI insider Sam Woods. We fund larger land deals...

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