Real Estate Underground

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:

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:

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 [email protected].

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!

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 [email protected].

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 [email protected].

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!

Most people hear hotel conversion and picture a novelty deal. Dr. Alex Cartwright built a company around it, and the reason is arbitrage that is not subtle.

His firm buys hotels that have no future as hotels. Sometimes they are old and not worth remodeling. Sometimes they are newer but stuck in a crowded market as the least desirable option. Sometimes they just carry too much debt. Whatever the story, the test is the same: is the highest and best use of this building multifamily? When the answer is yes, the multifamily price is dramatically higher than the hotel price, and the conversion unlocks the difference.

The Denver project makes it concrete. A 310-room Holiday Inn sat next to Stapleton Airport until Denver built a new airport further out and the demand driver moved. Eleven stories, an atrium lobby, a balcony on every room, three underground racquetball courts. Nobody is building that again in a neighborhood of three and four story garden style apartments. Alex bought it a little under $30,000 a door and is spending $40,000 to $45,000 a unit to convert it, against comparable apartments in the mid to upper $200s.

In this episode:

Plus the Final Five, a poem called The Man in the Glass, and why you should always be looking for your next mentor.

About Dr. Alex Cartwright

Connect with Alex: hotelshift.capital. He writes the mailing list himself.

This week's book: How Elon Musk Thinks. He also recommended the economics blog Marginal Revolution and the All-In podcast.

Chapters

00:00 The rent-burdened middle: $45k to $75k a year

Real Estate Underground

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!

Most small real estate operators manage their finances by looking at what is in the bank. Money in is income, money out is expenses, and the question every Monday is how do I survive the next ninety days. Alex Lopez, CPA calls that looking in the rear-view mirror, and he spent more than a decade learning what the alternative looks like from the inside.

Alex started in real estate right out of high school during the South Florida boom, and he was in his early twenties when it all came down. He lost the properties he had bought. Going back to finish his business degree, he hit the two accounting courses every Florida business major has to take, and found that the numbers were a language that explained his own mistakes better than the market crash did. He switched his major, went straight into a global firm, asked to be put on the real estate clients, and drew a $4 billion hotel REIT as his first account. Corporate came next, then helping take a company public, then his own shop.

The thing he brought back is the spine of this conversation. The most powerful things those firms do are perfectly doable at any size. It comes down to structure, skill and prioritization, and to somebody actually being assigned the work.

In this episode:

• What a fractional CFO actually does that a bookkeeper does not
• Why you should run your company as though it were already much larger
• The windshield versus the rear-view mirror, and why most accounting only looks backward
• KPIs and plans: NOI, rent per square foot, CAM, occupancy, and how to pick yours
• Reverse-engineering a business plan into a debt and equity structure
• The free playbook hiding in plain sight: the 10-K filings public companies in your field are legally required to publish, KPIs included
• Why the skill set changes completely at every revenue tier

Plus the Final Five, a mentor named Anatoly, and the one mistake Alex committed to never making again.

About Alex Lopez, CPA
Alex Lopez, CPA is the Managing Partner of Osher CPAs, a South Florida firm providing accounting, CFO services, financial due diligence, and tax strategy to real estate investors, property managers, and growing businesses. He works primarily with owners in the low seven-figure to mid eight-figure range.

Connect with Alex: alexlopezcpa.com

This week's book: Get Scalable: The Operating System Your Business Needs To Run and Scale Without You by Ryan Deiss

Chapters

00:00 The big-firm playbook is available to the rest of us
 00:45 Welcome to Real Estate Underground
 01:40 Meet Alex Lopez, CPA
 02:00 Growing up in the South Florida boom
 02:45 The 2008 crash, and losing everything in his early twenties
 04:45 Stumbling into accounting: the language of business
 05:50 Why the global firms only hire you straight out of school
 06:30 Canvassing commercial property the old-fashioned way
 08:15 Asking to be put on the real estate clients
 08:45 First client: a $4 billion hotel REIT
 09:30 Into the corporate world, then taking a company public
 11:00 Opening his own shop
 11:35 What a fractional CFO actually is
 12:30 More than a decade inside: it is structure, skill and prioritization
 13:30 Think of yourself as a much larger company
 14:30 The windshield, not the rear-view mirror
 16:00 KPIs and plans: where a CFO starts
 17:00 Reverse-engineering the plan into financials
 17:50 The metrics that matter: NOI, rent per square foot, CAM, occupancy
 20:00 Debt versus equity, and what you actually need to raise
 21:20 Your neighbor's daughter who does the bookkeeping
 21:50 The skill set changes at every revenue tier
 22:45 The free playbook: read the 10-Ks of public companies in your field
 24:45 They share their playbook because legally they have to
 25:00 Ed's story: running a $1M company like a $100M company
 27:00 You miss 100% of the targets you don't set
 28:50 The Final Five
 29:00 Purpose: the high-rises of Medellin
 29:45 Best advice: intentional hats, from a mentor named Anatoly
 30:40 The mistake: selling property
 33:50 Nobody regrets holding a property too long
 35:40 This week's book: Get Scalable by Ryan Deiss
 37:00 The E-Myth, Buy Back Your Time, and who he serves
 39:30 How he defines success
 40:20 Where to find Alex

Real Estate Underground
Hosted by Ed Mathews of Clark St Capital. New episodes every Tuesday.
clarkst.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!

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!

Rob Bergeron writes a free newsletter at five in the morning, five days a week, and has for years. One Saturday he sent it out saying he saw something happening between data and energy and wanted in. A reader named Mark, who had never once replied in five years, wrote back. That email became a data center company that has since shrunk the standard footprint by 92 percent.

That is the whole method. Rob publishes in public, constantly and for free, and lets the right people find him.

Rob calls himself the tilapia of realtors. He owns Winner Realty in Louisville, runs OffMarket.deals nationally, writes The Morning Bergeron five days a week, and is building what he hopes becomes the institutional standard for data centers. On paper that is four unrelated businesses. In practice it is one move, repeated.

The wholesalers in Louisville were all convinced they were competing for the same buyers. Rob ran comps for them for years and never once took a deal off them. When he finally asked for their buyer lists, they handed them over. He merged those lists with his own, charged two thousand dollars only when he brought the buyer, and made forty two thousand in year one. That business is now OffMarket.deals.

He posted on the BiggerPockets subreddit because nobody else was posting there. That produced David Greene.

He sent one newsletter into the void about data and energy. That produced a partner, a connection to HKS, and a design that shrinks data center footprints by 92 percent, runs closed loop on 40 gallons of water a year, uses submerged cooling so it makes no noise, and routes its waste heat to farms.

And he sends unsolicited letters of intent to listed properties and for-sale-by-owners on behalf of his clients' buy boxes. Direct mail hits at 1.1 percent and costs money. Rob hits at 2.1 percent and spends nothing.

His frame for all of it: we are in the NIL era of real estate, where everyone has to earn everyone's business. Nobody is owed a repeat client.

Rob also gives one percent of Winner Realty's net profits to Hand in Hand, which builds houses in Belize for about ten thousand dollars each. His stated legacy goal is one house every month, forever.

Find Rob: The Morning Bergeron newsletter, and OffMarket.deals for assignable contracts and the buyers list.

This week's book: The Power of Moments by Chip Heath and Dan Heath

Chapters

00:00 The NIL era of real estate

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!

Will Harvey got into real estate the way a lot of people do. He dropped out of college after a double hip surgery ended football, landed on a mortgage desk in 2015, and figured out fast how leverage worked. He bought his first house on a $30,000 salary with his dad as a co-signer, rented out two of the three bedrooms, and house hacked a deal before he knew the word for it.

Then came the part nobody puts in the brochure. Three rentals in an expensive market, no money left, and the discovery that owning property is not passive. As Will puts it, the only genuinely passive position in real estate is limited partner, and you pay for it by giving up control.

So he kept moving. He left a high-paying W2 to flip houses, rolled the flip profits into syndications, took bonus depreciation against the gains, did a couple of deals as a GP. And somewhere in there he figured out what actually excites him is the finance side of the table, not the operating side.

That led to a friends-and-family fund in 2023, an accidental first hard money loan, and eventually a dedicated 506(c) fund built on a specific idea: that hard money underwriting is due for a rebuild from first principles.

Will walks through the seven risks he underwrites against, why he thinks most lenders collect the wrong paperwork while skipping the single most predictive input available, and how he uses AI to compress an underwriting file from hours to about ten minutes without giving up the verification step.

He also talks about the $70,000 he lost on a deal he already knew he should not have taken, what he looks for in an investor conversation before he will accept a wire, and why the boring end of real estate is the point rather than the compromise.

What you will learn

• Why Will chose debt over equity, and what that decision has to do with temperament rather than returns
• The first-principles exercise he ran on lending, and the seven risks it produced
• Which document lenders over-collect, and which input they skip entirely
• How AI actually sits in his underwriting stack, and where he still verifies by hand
• What he screens for in a first conversation with a prospective investor
• Why he charges points and has no prepayment penalty

Connect with Will Harvey

Website: harvey-capital.com

Email: [email protected]

LinkedIn: search Will Harvey, Harvey Capital

This week's book

Titan: The Life of John D. Rockefeller, Sr. by Ron Chernow

Will also mentioned The Book of Elon, a compilation of Elon Musk's own thinking pulled from interviews. He reads both the same way: printed out, at night, when his mind has slowed down enough to actually absorb it.

Chapters

00:00 Cold open: the first call with a borrower
00:35 Welcome
01:40 Who Will Harvey is and what Harvey Capital does
02:27 Dropping out, double hip surgery, and the mortgage desk
03:43 House hacking the first deal before he knew the term
04:44 Nothing about owning rentals is passive
05:29 Leaving a high-paid W2 to flip houses
06:31 The realization: he is not an operator, he is a finance guy
06:58 The 2023 friends-and-family fund
07:50 The accidental first hard money loan
08:06 Graduating from a 506(b) to a 506(c)
10:02 Why debt instead of equity
13:13 How he protects capital
13:32 Applying SpaceX first principles to lending
15:53 The seven risks he underwrites against
16:25 Over-documenting what does not matter
17:00 The borrower's story as the real underwriting input
18:49 A word from Elevista Connect
19:52 Screening investors on temperament, not just accreditation
20:04 Why the one-year term filters people out
21:00 Boring is the whole point
23:20 Where the borrowers actually come from
23:30 Google ads, and turning them off
24:15 The REIA coin flip
28:39 How Will uses AI to run the business
28:44 Claude Code on the terminal
30:40 Recording borrower calls as a data point
31:52 Compressing hours of underwriting into ten minutes
32:36 Incumbent lenders move like turtles
33:01 Why flippers actually buy speed
35:09 No prepayment penalties, and the reason why
36:23 Lightning round
36:52 What drives him
37:50 The best advice he ever got
38:25 Buffett: price and value are two different things
39:40 The decision he would take back
40:44 Losing $70,000 on a deal outside the buy box
41:32 The return on brain damage
41:52 What is on his nightstand
41:58 Titan, and The Book of Elon
43:33 Ed's NotebookLM workflow for books he never gets to
45:55 How Will defines success
46:12 Outcomes are a distraction, focus on the process
47:50 You only get 18 summers
48:56 How to reach Will
49:03 harvey-capital.com

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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)

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