Palmy Kitti and her sister Nan started a fashion business with $2,000. Years later their biggest client shut down all its retail stores and 95% of their income was gone overnight. They moved into flipping houses in Los Angeles, then into multifamily syndication. Seven and a half years in, Palmy says they have nearly half a billion dollars in assets under management across Georgia, Arkansas and Texas.

Now a lot of that business runs through AI. After a property management changeover, her system flagged that one property had more cash than its reports showed. They'd overfunded the reserve account by $169,000. Finding that used to mean people matching rent rolls against the T12 and the general ledger by hand. She says it took her less than five minutes.

She's just as clear about where AI stops. "You can have the best AI tools, but AI doesn't give you that judgment. You have to make that judgment."

What Ed and Palmy get into:

• The $169,000 her AI caught in a reserve account after a property management changeover
• A fire that burned eight units with only two occupied, and the eight-page report that got the insurer to approve business interruption on all eight: $136,000 through August versus $32,000 for two
• Her AI investment committee, with a risk role, a capital role and a market role that each try to find the flaws in a deal before a CEO role sums it up
• Why AI multiplies the advantage you already have and can't create one for you
• Ed's rule for the AI agents in his flip business: they handle execution, never judgment
• How a newer investor can use AI to bring real value to an experienced general partner
• The partner who stole her investor list, and the partners who went quiet during a refinance
• Why drinks on Thursday doesn't mean you get married on Saturday
• The investor on their dead list who invested five years later
• "Earn to own," and what Fortune Builders taught her about owning assets before buying things

Also in this episode, Questions from the Underground: when do I quit the job? Ed covers what has to be in place before you leave your W-2: insurance, cash reserves, debt, plus structure and protection.

Book mentioned:

• The Innovation Secrets of Steve Jobs by Carmine Gallo, Palmy's pick

Learn about Palmy's AI operating system at kittiroadmap.com, and find The Kitti Sisters at thekittisisters.com and on YouTube, TikTok, Instagram and Facebook.

Got a question you want answered on the show? Send it to ed@clarkst.com.

Recorded September 2026.

Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or elevista.com/podcast

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Elevista Connect is the first AI-powered lead conversion system built for real estate investors.

🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.

Additional Resources:

• Clark St Capital -> Passive real estate investments for busy business owners and executives
• Elevista -> AI SaaS for real estate investors
• Clark St Academy on YouTube -> Learn how to invest in real estate

Social Media:

• LinkedIn -> Ed Mathews (President at Clark St and Elevista)

Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!

Jason Williams spent 15 years as a chemical engineer. He's owned real estate since 2003 and large multifamily since 2017. When he started underwriting apartments, half the spreadsheets he was handed had broken cells and equations that didn't work, so he built his own model. People kept asking him to show them how it worked, and that model became Ironclad Underwriting.

His rule is simple: never underwrite off your own numbers. The property manager tells him what each unit can rent for. The insurance broker prices the premium off comparable properties, and he uses the high end of the range. A tax advisor fights the assessment. And the plumber's bid gets multiplied by three, sometimes four.

"Every single property I've had from a 1950s build up to early 2000s has had major plumbing issues."

What Ed and Jason get into:

• Why a T12 almost never ties to the bank statements, and when that gap is actually a red flag
• Rent rolls that look clean but hide a rollover cliff, and why the manager, not the spreadsheet, sets pro forma rents
• Insurance priced on replacement cost, and what Texas nondisclosure does to your tax bill after you buy
• The tax advisor who saved him $20,000 one year and $11,000 this year, paid only on a percentage of what he saves
• Why he no longer chases agency debt, even with the better rates
• A 72-unit plumbing job that put residents in a hotel for two weeks, and a gas leak that shut off the gas over Easter weekend
• Ed's sewer line on a 10-unit building that passed inspection: a $5,000 to $10,000 fix at purchase that became $44,000 a year and a half later
• Six months of reserves, and why Ed doubled his after the pandemic
• The zoning mistake on a mobile home community that has cost Jason more than a year of unexpected debt service

Also in this episode, Questions from the Underground. An experienced Connecticut investor asked Ed whether it's time to cycle back to cash flow deals or keep riding the appreciation wave. Ed's answer: it's always a cash flow play. Appreciation is the cherry on top, not the basis of a business plan.

Books mentioned:

• Who Not How by Dan Sullivan with Dr. Benjamin Hardy, Jason's favorite
• The E-Myth Revisited by Michael E. Gerber

Connect with Jason Williams at ironcladunderwriting.com, or on LinkedIn. His free underwriting resources and his weekly underwriting podcast are on the site.

Got a question you want answered on the show? Send it to ed@clarkst.com.

Recorded September 2026.

Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or elevista.com/podcast

Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.

🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.

Additional Resources:

• Clark St Capital -> Passive real estate investments for busy business owners and executives
• Elevista -> AI SaaS for real estate investors
• Clark St Academy on YouTube -> Learn how to invest in real estate

Social Media:

• LinkedIn -> Ed Mathews (President at Clark St and Elevista)

Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!

Stewart Heath, CPA went into 2008 over-levered and under-reserved. He handed buildings back to the banks. He says that for want of roughly $300,000 in reserves he would still own them, and every rule he operates by now was built backward from that number. His book is called "Don't Do What I Did."

Stewart runs Harvard Grace Capital out of Spring Hill, Tennessee, buying stabilized commercial assets along the I-65 corridor from Nashville to Birmingham. Medical office, suburban office, storage, retail and warehouse. Eleven assets by the company's count and more than 300,000 square feet. Their tagline is boring is beautiful. It is printed on the banners.

"There's not a whole lot boring about 13% cash on cash returns."

What Ed and Stewart get into:

• The 12 months of mortgage reserves he sets aside on every deal, sized as if the property income goes to zero, and what holding that money costs him in returns
• Why medical office is his favorite asset class: hundreds of thousands of dollars of tenant build-out, 10 year leases, triple net with 3% bumps and tenants who treat rent as a line item instead of a negotiation
• Suburban office and service retail, the class B buildings where a business meets its customers rather than collects its employees
• Why he underwrites a geography and not an asset class
• Why he refused to run a fund for years, and what two independent RIA relationships changed
• Retail moving from 25% food and restaurants to almost 60%, with price per square foot almost doubling in three years
• Why he stopped doing single-tenant deals after watching a tenant walk out on 10 years of lease
• The contrarian office call: nobody can finance new office, the population is not shrinking and one of his buildings sits in a town under a two year sewer moratorium

Also in this episode, a new segment called Questions from the Underground. An investor owns 19 units two states away. His manager reports 95% occupancy every month and his distributions have shrunk four quarters in a row. Ed walks through the per unit profit and loss that tells him whether he has a building problem, a manager problem or one bad quarter.

Books mentioned:

• "Don't Do What I Did" by Stewart Heath. Free at harvardgrace.com for an email address.
• Who Not How by Dan Sullivan with Dr. Benjamin Hardy. Stewart is on his third read.
• The E-Myth Revisited by Michael E. Gerber
• Buy Back Your Time by Dan Martell
• Rich Dad Poor Dad by Robert Kiyosaki, the book his mentor handed him

Connect with Stewart Heath at harvardgrace.com, or on LinkedIn. The free book and his calendar are both on the site, and he will talk real estate with anyone.

Got a question you want answered on the show? Send it to ed@clarkst.com.

Recorded June 2026.

Real Estate Underground with Ed Mathews. Find us wherever you get your podcasts, at clarkst.com/podcast or elevista.com/podcast

Elevista - Speed as a Service™
Elevista Connect is the first AI-powered lead conversion system built for real estate investors.

🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity.

Additional Resources:

• Clark St Capital -> Passive real estate investments for busy business owners and executives
• Elevista -> AI SaaS for real estate investors
• Clark St Academy on YouTube -> Learn how to invest in real estate

Social Media:

• LinkedIn -> Ed Mathews (President at Clark St and Elevista)

Heads up: If you find this week's book intriguing and you buy using our link, we receive a small commission that helps support the show. Thank you!