Real Estate Underground
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 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 weekly.
Episodes
193 episodes
Plan A, B, and C: Buy More Land with Brandon Cobb
Brandon Cobb's business model is simple: take farmland, get it approved for housing, and sell it to national home builders like Lennar and DR Horton. The builders have no choice but to buy. They're publicly traded. Plan A is buy land and build ...
It's Not Gambling, It's Building: A Billion-Dollar CRE Playbook with Ben Reinberg
Ben Reinberg has done over $1 billion in commercial real estate transactions. He didn't get there chasing returns. He got there by treating CRE as what it actually is: a hard asset that produces cash flow, not a bet.Ben is the Founder a...
Obscurity is the Enemy: AI, Marketing, and the Operator's Edge with Clay Lehman
Clay Lehman spent 20 years in real estate, starting at Arthur Andersen, running the Ocala controller desk for Pulte Homes, and eventually building Lehman's Strategic Partners to help agents grow their businesses. He runs an AI Facebook group wi...
123% Leverage and the Crash That Changed Everything with Joel Kraut
Joel Kraut co-founded BRRRR Loans after losing $4.2 million in the 2008 crash. He had 144 properties at over 100% leverage when the market turned. Five tenants called the same day to say they couldn't pay rent.Today he runs on...
No Government Owns Us: Building a Global Real Estate Portfolio with Ladislas Maurice
Ladislas Maurice left a corporate career at Nestle to spend the last nine years investing in real estate across emerging and frontier markets around the world. He buys apartments in Nairobi for $65,000, sits on land in Nicaragua, and flips prop...
From Gold Bricks to Gold Coins: Real Estate Tokenization with Tyler Vinson
Tyler Vinson has spent 25 years in investment real estate, from duplexes and flips to multifamily, commercial, and Class A storage. Now he's building the infrastructure to bring real estate into the digital age as the founder of RE Tokens, one ...
Time, Money, and the $21 Million Leap with Ashley Garner
Ashley Garner grew up swinging a hammer on student rentals near West Virginia University. Decades later, he jumped from a 35-unit portfolio to a $21 million, 196-unit acquisition in North Carolina. In this episode, he breaks down what that leap...
Dead Retail, Live Returns with Neil Henderson
Neil Henderson is a general partner and Director of Investor Relations at Nomad Capital, a Wilmington, NC-based private equity firm with a twist on self-storage: they buy vacant big-box retail buildings and convert them into climate-controlled ...
The 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,...
Deal 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...
From 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 tro...
The 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.<...
Riding 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 InsightsIn this insightful episode of the Real Estate Underground podcast, host Ed Mathews welcomes Kenny Bedwell from STR Insights ...
AI 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 ma...
From Contractor to Mogul: Joao Macavilca's Real-Estate Adventure
Episode Resources:Website: www.stf-capital.comIG: @Joaomac_stfFB:
Patience Is Profit: Finding Great Deals in Today’s Real Estate Market with Mike Zlotnik
Episode Resources:Website: bigmikefund.com
How to Fund Your Real Estate Empire Without a W-2 with Jimmy Rios
Episode Resources:YouTube: Rios Business FundingInstagram: @riosbusinessadvisors...
From Oil Fields to Real Estate Empires with Casey Gregersen
Episode Resources:YouTube: @CaseyGregersenInstagram: @CaseyGregersenLinkedIn: linkedin.com/in/caseygregersenMobile: 307-317-2494
Solving Affordable Housing Through Co-Living with Sam Wegert
Episode Resources:Website: scaleyourrealestate.comInstagram: @samwegert
Non-Correlated Investments: Protecting Your Wealth When Markets Crash with Patrick Grimes
Episode Resources:Website: investwithpatrick.comBook: passiveinvestingmastery.com/book
Billion-Dollar Tax Savings: A Conversation with the Tax Goddess
Episode ResourcesWebsite: taxgoddess.com
Building Wealth Without Feeding the Tax Monster with Jason Melillo
Episode Resources:Website: https://kbkg.comFree Giveaway: https://www.kbkg.com/residential-costsegregatorPromo Code: Underground2025LinkedIn: linkedin.com/in/jasonmelillocpa
Why Self-Storage Outperforms other Real Estate Assets Even in the Worst Market Cycles with Joe Downs
Episode Resources:Email: joe@belroseam.comCoaching Class: Scott Meyers Academy