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!

Twenty-five years ago Jeff Emalaba was a guest host on CNBC Africa, analyzing derivatives, commodities and futures, and holding an options license in Florida. He describes all of it as one subject: risk transference. That is the lens he brought to real estate, which makes what happened next harder to explain and more useful to hear.

He drove two hours to see a duplex in North Carolina and walked it with his agent. Nothing looked wrong. He asked the seller why the previous buyer had backed out and was told they could not get funding. He asked his agent to dig further. Nothing came back.

So he paid. Five thousand dollars in non-refundable due diligence fees, five thousand in earnest money, six hundred seventy-five for an inspection, seven hundred for an appraisal. That money was committed before anyone had been inside the walls.

Then the inspector came back with one word: run. Foundation, structural, roofing, mold, electrical.

Jeff didn't believe him. He decided the inspector was exaggerating and hired a general contractor to go prove it, fully intending to pay that contractor to fix whatever turned out to be wrong. The contractor sent back a ten-page email explaining why he should never buy the property unless he had a hundred thousand dollars to spend. Jeff walked. The seller kept the money.

The part Jeff wants investors to understand is how all of that was legal. A seller who already knows about a prior buyer's inspection report can select no representation on the disclosure form, stay silent, and keep the fees when the deal dies. He calls it the no representation loophole, and it is what sent him to build InvestFusion.

Ed presses him on the part that matters to anyone evaluating a tool like this: where does the data actually come from, and what happens in the middle when you ingest three inconsistent sources and output one confident answer. Ed asks as an operator who runs his own deals through AI, not as a host taking a pitch.

Also in this episode: why Ed thinks a Zestimate is not merely inaccurate but dangerous, what a single government tenant can do to a commercial deal, the four fees an investor can lose before owning anything, Manny Khoshbin's "you make your money on the buy," and Ed's own translation of the word pro forma.

Questions from the Underground is back at 26:38. Jack, an investor in North Carolina, analyzed sixty deals in three months and made zero offers because nothing penciled. He wants to know whether the market is broken or he is. Ed's answer: sixty analyzed and zero offered is not caution, and there is a three-step sort that tells you which of your buy box, your cost of capital, or your read on the market is actually wrong.

Connect with Jeff Emalaba

• InvestFusion: investfusion.co
• LinkedIn: linkedin.com/in/jeff-emalaba
• Jeff made a page just for this show, with his deal-killing red flag cheat sheet and his 60-second vetting blueprint: underground.investfusion.co

On the nightstand

Jeff's go-to, read many times over: Goals! by Brian Tracy

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!

Mark Khuri co-founded SMK Capital Management with his father, Dr. Suheil Khuri, pooling family capital informally before opening the firm's doors in 2010. They operated properties directly through 2017, then pivoted entirely to the LP side. Today SMK reviews 600 to 700 private real estate deals a year and invests in roughly 1 to 2% of them, call it 5 to 10 deals annually, across diversified funds, single-asset deals, and one-off syndications for their investor base.

Ed and Mark get into the mechanics of how SMK actually filters that flow: a 40-point due diligence checklist covering firm credentials, deal-level underwriting, and required deliverables, the discipline of comparing an operator's underwritten returns against their actual results on deals that already went full cycle, and the red flags that end a conversation before it starts (a principal who won't share their last name is an automatic no).

From there, the conversation turns to mobile home parks, an asset class SMK has been investing in since 2012. Mark explains why new supply is structurally constrained (NIMBYism, unaffordable construction economics), why 70 to 80% of parks are still owned by mom-and-pop operators with no succession plan, and the specific value-add levers SMK targets: occupancy infill and converting park-owned homes into tenant-owned homes through rent-to-own financing structures. He's candid about where the asset class has gotten more competitive, cap rates in some markets have compressed from north of 10% a decade ago to 3 to 4% today, and why SMK stays out of the priciest infill deals and the most distressed ones alike.

The episode closes on underwriting discipline: the hardest deal Mark walked away from recently, and why "pro forma" so often needs a second, much more skeptical read.

Also in this episode: the first installment of Questions from the Underground, where Ed answers a real problem an investor put to him: a contractor took most of the draws, the job is 40% done, and the contractor has gone dark. What to do first, on tape, no filler.

Real Estate Underground publishes every Tuesday.

Chapters
0:00:00 Cold open: "We like to see underwritten returns versus reality"
0:00:40 Real Estate Underground intro
0:02:03 Welcome Mark Khuri, SMK Capital Management
0:03:32 From property operator to fund-of-funds: the 2017 pivot
0:05:06 Going for the no: SMK's first filter on any deal
0:07:23 The 40-point sponsor due diligence checklist
0:09:02 Red flags: the people behind the deal
0:11:21 The exit-strategy question that reveals alignment
0:12:33 Why mobile home parks: the supply story
0:14:44 Ownership is still mom-and-pop: the value-add opportunity
0:16:28 Converting park-owned homes to tenant-owned
0:19:30 Still a darling, or getting crowded? Cap rate compression
0:21:28 Where SMK's deals actually come from
0:21:50 Questions from the Underground: the contractor who took the draws and vanished
0:26:49 The hardest deal Mark walked away from
0:27:57 "Pro forma is Latin for full of shite"
0:29:58 Cashflow gets you through the downturns
0:30:51 Final five: purpose, mentors, and the "show them 15" lesson
0:36:32 Who Mark reads: Jay Parsons, Marcus & Millichap, Richard Duncan
0:37:13 Defining success, life in Bend, Oregon, and how to find SMK

Connect with Mark Khuri:
smkcap.com
linkedin.com/in/mark-khuri-7543821

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!

Shams Merchant structures syndications and investment funds for clients across the country. He also runs his own fund-of-funds, allocating LP capital across about fifty sponsors, which means he sees both sides of the table: he writes the documents, and he reads other people's documents deciding whether to invest.

That vantage point is what makes this episode useful.

On AI: he gets the ChatGPT question weekly now. His answer is not that the technology is bad, he uses it heavily. It is that a model has no access to which structures have actually been tested and litigated with the SEC, and no discretion about what belongs in a document and what does not. You are not paying for a stack of paper. You are paying for someone whose malpractice insurance stands behind the decision.

On what LPs check: they can spot AI-drafted documents immediately. They ask who your law firm and your CPA are, because they want to know who is backing you. They do not want a five-hurdle waterfall nobody can follow. They do not want seven stacked fees. They want clawbacks, so a disposition fee disappears if the deal misses its return metrics. And they want a GP contribution that is real cash out of your pocket, not an acquisition fee recycled back into the deal and called skin in the game.

On 506(b) versus 506(c): Shams defaults to C for nearly everyone. B only makes sense on a small raise, or when you have spent a decade building an investor base deep enough to fill the round from existing relationships. His words: you only know so many human beings.

The last stretch is the one that will stay with you. Shams thinks there will be meaningfully fewer lawyers within a few years, that one attorney with good tooling can run a two-hundred-million-dollar deal, and that AI already redlines a standard contract better than a first-year associate. Ed pushes on the obvious problem. If nobody hires juniors, where do the seniors come from?

Books mentioned this week
The Price of Tomorrow by Jeff Booth
https://www.amazon.com/Price-Tomorrow-Deflation-Abundant-Future/dp/1999257421?tag=clarkstholdin-20

The Eight Secrets to Powerful Manifesting by Mandy Morris
https://www.amazon.com/8-Secrets-to-Powerful-Manifesting/dp/1401969550?tag=clarkstholdin-20

Connect with Shams Merchant
Commercial Real Estate Law Group (CRE Lawyer) at MW Law, with offices in Dallas, Houston, and Fort Worth and a national practice.
Website: cre.law
LinkedIn: linkedin.com/in/shams-merchant
As he says at the close: Google "Shams Merchant," it is all public.

Connect with Ed Mathews
Website: clarkst.com
Real Estate Underground is where operators talk about what is actually working. No sales pitches allowed.

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!