Real Estate Underground

By Ed MathewsBusiness Entrepreneurship Investing Marketing

Real Estate Underground episodes

March 10The Cincinnati Mistake That Built a $2 Billion Company with Joe Fairless
Joe Fairless built Ashcroft Capital into one of the most recognized multifamily syndicators in the country — $2B+ in assets, properties across the Sunbelt, and a vertically integrated management company. But he started with $30K, student loans, and an apartment in New York where one paycheck covered rent and the other covered everything else.
In this episode, Joe gets candid about the deals that didn't work, the market conditions that are keeping multifamily investors in a holding pattern, and the one acquisition strategy most operators are completely ignoring right now: going direct to the lender.
Here's what we cover:
Why Fort Worth and Orlando are Ashcroft's two highest-conviction markets heading into late 2026
How Joe acquired a property for less than the outstanding debt — and what it took to get there
The lender relationship play that gives you first look at off-market distressed deals (even if you don't have your own management company)
Where the supply/demand shift is — and why Q3 2026 is the number operators keep landing on
Joe's personal 3.5% math: out of 140 LP deals across 50+ operators, what's actually gone to zero
The fixed vs. floating rate lesson that still stings
How Joe defines success — and it has nothing to do with deal count
Joe also shares his three bucket list goals for the year. One involves a fifth grader with a 2040 chess rating. That's all we're saying.

This week's book: The Road Less Traveled by M. Scott Peck
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!
33 min
March 03Deal Junkie Diaries: Michael Pouliot Talks Strategy for 2026 and Beyond
In this episode, Ed welcomes Michael Pouliot of Carbon Real Estate Investments, a vertically integrated private equity firm operating workforce housing apartments across the Southeast.
Pouliot explains Carbon’s buy box: 100–300 unit, older vintage (1970s–1990s) properties in strong school districts and stable submarkets, targeting families and raising rents about 20% through substantial CapEx that prioritizes deferred maintenance alongside unit upgrades.
They talk about navigating Sunbelt challenges like insurance and taxes by avoiding high-risk areas, staying conservative in underwriting, and emphasizing strong entry pricing. Pouliot shares a bullish view that the next 12–18 months are a strong buying window as the market works through distress, debt maturities, and oversupply absorption, with more constructive sentiment and capital expected around 2027–2028.
He outlines Carbon’s strategy for 2026: keep buying with fixed-rate, low-leverage debt, hold long-term, and offer investor liquidity via recapitalizations rather than selling assets.
The conversation also covers regional scaling for operational efficiency, selective adoption of AI tools (voice/chat agents, SOP knowledge bases, automation) to augment staff, and Pouliot's perspective on purpose, mentorship, lifestyle trade-offs versus Wall Street, and how he defines success. Pouliot closes by directing viewers to investwithcarbon.com for Carbon’s weekly newsletter and content.
00:00 Cycle Outlook 2027-2028
00:11 Show Intro and Mission
00:52 Welcome and Subscribe
01:42 Meet Carbon Real Estate
02:44 Insurance and Tax Headwinds
05:07 Buy Box and Resident Avatar
07:01 Why Stable Markets Win
08:34 Distress Deals and Assumable Debt
12:29 Oversupply and Absorption Math
14:58 Strategy for 2026
18:41 Vertical Integration and CapEx
20:32 Tech and AI in Property Ops
14:23 AI Ops Automation
23:28 Human Touch Investing
24:31 Real Estate Tech Lag
25:19 Deal Junkie Purpose
26:23 Paranoia Prevents Errors
28:26 Wall Street What Ifs
33:38 Learning Diet Books
35:56 Defining Success Seasons
38:19 Life Outside Real Estate
41:05 Where To Follow Carbon
This week's book: How Countries Go Broke by Ray Dalio
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!
43 min
February 24From Prison to Paradise: Fuzzy Jardine and The Pono Way
This week, Ed welcomes Hawaii-based real estate developer and educator Fuzzy Jardine to Real Estate Underground.
Fuzzy shares his background growing up in Hawaii, getting into trouble with drugs and alcohol, going to prison, and using that time to educate himself with books like Rich Dad Poor Dad.
After struggling to find work as an ex-con, he took multiple jobs, then invested $26,000 in real estate education after hearing about Fortune Builders, and learned to find deals through strategies like bandit signs and Craigslist ads. He explains how taking action led him from deal-finding to partnering with a local developer and eventually building 100+ affordable homes for local families on a more rural island, typically priced around $300K–$425K.
Fuzzy talks about “The Pono Way,” emphasizing respectful, ethical investing, illustrated by a deal where a distressed homeowner was helped with housing, a car, and additional funds while the investors still profited. He also describes co-founding the Hui Mastermind with Asha Smith, including webinars, bus tours showing the full build process, meetups, and master classes teaching how to get started in real estate and fund deals without traditional bank financing.
In a lightning round, Fuzzy says family is his main purpose, shares advice about being on time and owning mistakes quickly, reflects on saying yes too often and taking responsibility for a project headed toward a loss, and names motivators he follows on YouTube and podcasts.
Check out Fuzzy's book, “Out of Paradise: How to Build Wealth Investing in Real Estate the Pono Way,” and shares where to find him online: fuzzyjardine.com, huimastermind.com, Instagram @hifuzzy, and YouTube “Investing in Hawaii.”

00:00 Take Action Mindset
00:11 Show Intro and Opportunity
00:52 Meet Fuzzy Jardine
01:54 From Prison to Real Estate
05:58 Why Building Homes
08:33 Finding Deals and First Partner
10:03 Working Three Jobs to Learn
12:30 The Pono Way Ethics
15:58 Hui Mastermind Origins
19:15 Lightning Round Purpose
20:28 Mentors and Hard Lessons
23:21 Books and Writing His Own
24:43 Defining Success and Fun
26:40 Where to Find Fuzzy
27:24 Final Thanks and Call to Action

This week's book: Rich Dad, Poor Dad by Robert Kiyosaki
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!
29 min
February 17The Lazy Investor Who Helped 2,000 People Buy Rental Properties
Melissa Nash spent $10K on a fully renovated $190K property with a tenant already in place.
Cash flows $200/month.
Sounds boring until you realize: $10K all-in. Someone else is buying her a house. And she never left California.
This week on Real Estate Underground: How a self-described "lazy investor" built a portfolio across five markets while coaching 2,000+ investors to do the same. No flying out to properties. No managing contractors. No second job disguised as passive income.
What you'll learn:
The questions that separate good property managers from disasters (hint: it's not about their fees)
Why Melissa went from flips and BRRRs back to turnkey investing—and why she's never looking back
How to vet teams 2,000 miles away when you can't be on-site
The $99K property that changed everything (and why fear almost killed the deal)
Property managers as your best acquisition source—if you ask the right question
Why this conversation matters:
Melissa made every mistake you're worried about making. Trusted the wrong contractors. Lost money on flips. Froze on deals for years. Then figured out a system that works.
If you're analyzing deals but not pulling the trigger—she's been there. If you're wondering how to invest out of state without getting burned—she learned it the hard way so you don't have to.
We talk systems, spreadsheets, and the "snowball payoff" strategy she swears she'll start using someday (she won't—because she loves buying deals too much).
For operators who:
Want to invest out of state but don't know who to trust
Are tired of real estate being a second job
Need a framework for vetting property managers
Want to hear from someone who's helped 2,000 people actually do this
No hype. No theory. Just 11 years of buying properties she's never seen—and making it work.
Hit subscribe. Leave a comment. Tell us what you're working on.
Real Estate Underground. Where operators talk to operators about what actually works.
Check out Melissa's free community at: hellomelissanash.com

This week's book: The Creature from Jekyll Island: A Second Look at the Federal Reserve by G. Edward Griffin
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!
43 min
February 10Riding the Short-Term Lane: Kenny Bedwell’s Data-Driven Journey to STR Riches
Mastering Short-Term Rentals with Data-Driven Real Estate Strategies - Featuring Kenny Bedwell from STR Insights

In this insightful episode of the Real Estate Underground podcast, host Ed Mathews welcomes Kenny Bedwell from STR Insights to discuss the intricacies of short-term rental investments.
Kenny shares his journey from a data analyst at Citibank to a successful real estate investor specializing in short-term rentals. He emphasizes the importance of choosing the right markets, investing in amenities, and focusing on the guest experience to succeed in the competitive short-term rental space. Kenny also highlights his strategies for managing properties remotely, leveraging local resources, and the value of balancing work and family life.
This episode is a must-listen for anyone looking to optimize their investments in the short-term rental market.

00:00 Introduction and Podcast Overview
01:19 Guest Introduction: Kenny Bedwell from STR Insights
01:45 Kenny's Background and Real Estate Journey
02:19 The Shift to Short-Term Rentals
02:45 Navigating Regulations and Diversifying Investments
04:00 Understanding the Short-Term Rental Market
09:17 Creating Unique Guest Experiences
15:50 Managing Short-Term Rentals Across Multiple States
20:07 Managing Property Operations
20:57 Human Capital and Property Management
23:35 Personal Drive and Motivation
25:09 Valuable Advice and Lessons Learned
32:41 Defining Success and Personal Growth
34:46 Hobbies and Family Life
37:25 Connecting with Kenny Bedwell

This Week's Book: The Pumpkin Plan: A Simple Strategy to Grow a Remarkable Business in Any Field (Entrepreneurship Simplified) - By Mike Michalowicz
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!
40 min
February 03AI Arbitrage: Why the Next 12 Months Will Separate Real Estate Winners from the Losers
What if you could turn a 10-hour due diligence process into 20 minutes of review?
Alberto Rizzoli, CEO of V7 Labs, reveals how AI workflow automation is eliminating the "purgatory" of real estate paperwork, and why operators who master it now will 10x their competition within a year.
In this episode, you'll discover:
⚡ The "napkin test" for identifying which processes to automate first (hint: weekly tasks taking 1+ hours)
⚡ Why AI fails at big, open-ended requests, and the simple fix that makes it reliable
⚡ How to abstract 1,000 leases without adding headcount as you scale
⚡ A free lease abstraction tool you can test today at scanmylease.com
About Alberto Rizzoli: Computer visionary turned founder, Alberto built V7 Labs into a platform processing hundreds of billions in transactions. His mission? Make work actually matter by eliminating everything that doesn't.
This Week's Book: Do the Work: Overcome Resistance and Get Out of Your Own Way - by Steven Pressfield
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!
35 min
October 07, 2025From Contractor to Mogul: Joao Macavilca's Real-Estate Adventure
Episode Resources:
Website: www.stf-capital.com
IG: @Joaomac_stf
FB: @STF_Capital
LinkedIn: Joao Macavilca
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!
29 min
September 30, 2025Patience Is Profit: Finding Great Deals in Today’s Real Estate Market with Mike Zlotnik
Mike Zlotnik moved from technology executive into real estate full time in 2009. Today his shop, Tempo Family, is a capital partner. They marry money to opportunity, write checks behind operators they trust, and stay out of asset classes where they cannot find a deep enough discount. So far this year, Mike has done one multifamily deal. He is not in a hurry.
The one deal was near Ann Arbor in Q1: 9 percent cap on purchase, 7 percent financing locked for three years, $79,000 a door against a $200,000 replacement cost. That kind of math is what Mike needs to see now.
What landed in this conversation:
The three-metric buy box. First, a 200 basis point positive spread between cap rate and cost of debt. Anything tighter than 150 bp is not enough margin of safety. Second, a steep discount to replacement cost. Third, a comparable discount to the 2022 peak pricing, which Mike pegs at 20 to 40 percent depending on submarket. If a deal does not clear all three, it does not get capital.
Open-air retail as the contrarian play. Tempo Family is eight deals in on open-air shopping. Every one has performed. While multifamily got overbuilt and roller-coastered through 2022, open-air supply got squashed by the Amazon fear and never recovered. Recent example: a San Diego open-air at 9.25 cap with 84 percent occupancy, financed at 6.5 percent fixed for ten years, with anchor tenants like Starbucks and Cheesecake Factory.
Industrial as predictability. Flex industrial and single-tenant triple net at 8 to 9 cap. Twenty to twenty-five year leases. Two to three percent annual rent escalators, which in triple net is pure NOI growth because the tenant is paying everything. No surprise capex.
The asset classes he refuses to chase. Storage cap rates are too low. Hospitality is an operating business in real estate clothing. Senior living, same. Office is broken. Data centers cost a fortune to build and Tempo Family's net asset value is the "rounding error" on those deals. Better to know the don't-buy box than to chase yield.
The regret he owns: deals done in 2021 and 2022 he wishes he had not. "I'm the fool who's learning from his own mistakes." After that he went back and re-read Howard Marks on cycles.
Books on Mike's nightstand right now: Mastering the Market Cycle by Howard Marks (he says read it after every cycle), How Countries Go Broke by Ray Dalio (third read), and Richer, Wiser, Happier by William Green.
Reach Mike at bigmikefund.com (his podcast entry point, links to the Tempo Family corporate site).
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!
38 min
September 23, 2025How to Fund Your Real Estate Empire Without a W-2 with Jimmy Rios
Episode Resources:
YouTube: Rios Business Funding
Instagram: @riosbusinessadvisors
TikTok: @riosbusinessadvisors
Amazon: Decoding The Mystery of Business Credit
Website: riosbusinessfunding.com
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!
39 min
September 16, 2025From Oil Fields to Real Estate Empires with Casey Gregersen
Casey Gregersen worked twelve years as a petroleum engineer at Shell. The job had an unusual rhythm: two weeks on a drilling rig, two weeks completely off with zero work responsibility. He used the off weeks to start buying houses. In October 2022, with three companies running, he walked away from Shell.
Today Casey runs Bighorn Capital Fund, Wile Homes, and Gregersen Properties. He invests primarily in Wyoming, a market where his only real competition is the lack of contractors to keep up with demand. That contractor shortage was the central problem he had to solve to scale.
What landed in this conversation:
The VA build during COVID layoffs. Shell laid off 40 percent of Casey's team in 2020. Instead of waiting to see if his number got called, he sat down and read The 4-Hour Work Week, then recorded himself doing every property management task he was already running from Houston. Wrote it all into SOPs. Hired and trained a virtual assistant. The VA owned the SOPs from that day. That was the unlock that let the side hustle scale.
The local bank shortcut. Early on, instead of working with big mortgage brokers, Casey walked into a small local bank in the Wyoming town he was investing in and did a deal. The relationship compounded across dozens of properties. Most new investors miss this because they assume the broker network is the only path.
The in-house contractor model. Wyoming does not have a deep GC bench. Casey solved it by hiring four to five 1099 crews directly. When a deal hits his pipeline, he is talking to the guy who will actually do the work, and that guy controls the schedule. The timeline gets predictable. The carry costs drop. The investor pitch becomes "here is our budget and here is our timeline, and we know we can hit it" because the labor is not a third party balancing five other clients.
The two-exit rule. Casey scaled up to $500,000 to $700,000 fix-and-flips in the TCU area with a new GC and project manager. Properties stopped selling. He had to drop the list price by $10,000 a week until they cleared, on the advice of his hard money lender. The lesson, in his words: never run a flip where your only exit is selling at ARV. Always have a refinance-and-rent fallback. In Wyoming his $150,000-buy / $50,000-rehab / $300,000-sell deals could always pivot to a rental that covered the debt. Every single deal has a curveball.
Book Casey keeps coming back to: Capital Gaines by Chip Gaines, for the "win-win either way" framing.
Reach Casey at @CaseyGregersen on YouTube, Instagram, and LinkedIn, or text him directly at 307-317-2494.
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!
37 min

About Real Estate Underground

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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,…

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