『Real Estate Underground』のカバーアート

Real Estate Underground

Real Estate Underground

著者： Ed Mathews
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Real talk from an operator who learned real estate the hard way.


Ed Mathews analyzed 1,100+ deals before buying his first property in 2011. Frozen in fear. He made every mistake, all while traveling 150+ nights a year working for some of Silicon Valley's top companies. 100+ deals later, he shares what actually works and what doesn't.


Each week, Ed brings you candid conversations with experienced operators, investors, and syndicators. No hype. No theory. Just real deals, real lessons, and the street-level intelligence you won't find anywhere else.

You'll learn and hear about:


Deals that worked (and the ones that didn't)

  • What we learned when contractors ghosted and we had to step in
  • How to vet opportunities when everyone else is sitting on the sidelines
  • Conservative underwriting in markets that punish optimism
  • Systems that protect capital when deals go sideways


Whether you're analyzing your first deal or your hundredth, this is the conversation you'd have over coffee with someone who's been there, made the mistakes, learned the lessons and built the track record.


New episodes every Tuesday at 12pm ET.

© 2026 Clark St Holdings LLC マネジメント・リーダーシップ マーケティング マーケティング・セールス リーダーシップ 個人ファイナンス 経済学
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  • $30,000 a Door: Dr. Alex Cartwright Brings Dead Hotels Back to Life

    $30,000 a Door: Dr. Alex Cartwright Brings Dead Hotels Back to Life
    2026/09/01
    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: What an end-of-life hotel is, and the three things that decide whether he enters a market at allWhy a hotel is already most of an apartment building: individual bathrooms, HVAC, front doors, parking, soundproofingWhich rooms get combined, and why going all studios pencils best but still is not the answerWhy the due diligence period runs several months instead of weeks, and why sellers grant itThe Denver numbers: under $30,000 a door in, $40,000 to $45,000 a unit of renovation, roughly $90 a door all inWhy an extended stay hotel converts for $10,000 to $15,000 a room insteadHow lenders underwrite the deal off stabilized value, the same way they underwrite a flip off ARVWhat cities are actually afraid of when you ask for the rezone, and the conversation that gets them to yesThe rent-burden math: more than half of rent-burdened Americans earn $45,000 to $75,000 a yearCutting a resident's housing cost by 35 to 40% without a dollar of taxpayer money 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 Dr. Alex Cartwright is the founder of HotelSHIFT Capital, based in Providence, Rhode Island, which acquires end-of-life hotels and converts them to multifamily housing. He spent ten years as an economics professor before moving to the operating side. 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 00:35 Welcome to Real Estate Underground 01:21 On location in Rhode Island 01:37 Meet Dr. Alex Cartwright of HotelSHIFT Capital 02:02 We are not in the hotel business 02:23 What an end-of-life hotel is 02:46 The arbitrage: hotel price versus multifamily price 03:04 Fundamentally we're in the apartment business 03:20 The buy box, part one: rent level 04:20 Part two: density and smaller units people accept 04:55 Part three: the regulatory environment 05:15 Why a hotel is already most of an apartment building 06:01 Floor plans: what gets combined and what does not 06:56 Why all studios pencils best and still isn't the answer 08:02 Ed on churn and sticky tenants at the best price in the market 09:05 Sponsor break 10:01 Vertical management or third party 10:41 Hold period, and where Opportunity Zones fit 11:08 The 24 to 36 month renovate-and-lease-up plan 11:18 Refinance and return roughly 100% of capital 12:00 Why due diligence runs months instead of weeks 12:43 The Denver deal: a 310-room Holiday Inn 13:27 Why hotels break down above 200 rooms 13:38 The airport that closed and took the demand with it 14:13 Bought a little under $30,000 a door 14:29 Six months of due diligence and Denver's energy codes 14:48 Adaptive reuse and why the architect comes in early 15:24 Construction cost: the more vertical, the more expensive 15:52 Eleven stories, an atrium, a balcony on every room 16:25 $40,000 to $45,000 a unit, and what that buys 16:44 Putting a kitchen in every room 17:08 An 18-month budget they expect to beat 17:27 Extended stay hotels convert for $10,000 to $15,000 a room 18:39 About $90 a door all in against low $200s 19:37 A-class amenities at a B-plus rent 20:16 How he finds these projects, and why there are more than he can buy 20:39 Why multifamily always deserves a remodel and hotels do not 21:21 The flag treadmill: a new brand every few years 22:24 Fewer hotel buyers, fewer hotel lenders, better deals 23:00 What changed after COVID 23:39 How lenders underwrite it, the same way they underwrite ARV 24:13 Rezoned before closing, so it's multifamily that needs work 24:35 What cities are actually afraid of 25:07 Not capital-A affordable housing 25:44 Who really lives in a $50 a night hotel 26:...
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    46 分
  • The Free Fortune 500 Playbook: Alex Lopez, CPA on Fractional CFOs and the 10-K Nobody Reads

    The Free Fortune 500 Playbook: Alex Lopez, CPA on Fractional CFOs and the 10-K Nobody Reads
    2026/08/25
    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 notWhy you should run your company as though it were already much largerThe windshield versus the rear-view mirror, and why most accounting only looks backwardKPIs and plans: NOI, rent per square foot, CAM, occupancy, and how to pick yoursReverse-engineering a business plan into a debt and equity structureThe free playbook hiding in plain sight: the 10-K filings public companies in your field are legally required to publish, KPIs includedWhy the skill set changes completely at every revenue tierPlus 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.comThis week's book: Get Scalable: The Operating System Your Business Needs To Run and Scale Without You by Ryan DeissChapters00:00 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 AlexReal Estate Underground Hosted by Ed Mathews of Clark St Capital. New episodes every Tuesday. clarkst.com/podcastElevista - 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial 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. ...
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    42 分
  • Investors Don't Invest in Deals: Shams Merchant on ChatGPT, the 506(c) Default and What LPs Actually Check

    Investors Don't Invest in Deals: Shams Merchant on ChatGPT, the 506(c) Default and What LPs Actually Check
    2026/08/18

    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!
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    44 分
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