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Description
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.
185 Episodes
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Send a text 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...
Send a text 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 abou...
Send a text 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 de...
Send a text 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....
Send a text 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...
Send a text 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 ...
Send a text Episode Resources: Website: www.stf-capital.comIG: @Joaomac_stfFB: @STF_Capital LinkedIn: Joao MacavilcaElevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate,...
Send a text Episode Resources: Website: bigmikefund.comElevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: Clark ...
Send a text Episode Resources: YouTube: Rios Business FundingInstagram: @riosbusinessadvisorsTikTok: @riosbusinessadvisorsAmazon: Decoding The Mystery of Business Credit Website: riosbusinessfunding.comElevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscrib...
Send a text Episode Resources: YouTube: @CaseyGregersenInstagram: @CaseyGregersenLinkedIn: linkedin.com/in/caseygregersenMobile: 307-317-2494 Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights on building...
Send a text Episode Resources: Website: scaleyourrealestate.com Instagram: @samwegert Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. ...
Send a text Episode Resources: Website: investwithpatrick.comBook: passiveinvestingmastery.com/bookElevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing y...
Send a text Episode Resources Website: taxgoddess.com Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: Clark S...
Send a text Episode Resources: Website: https://kbkg.com Free Giveaway: https://www.kbkg.com/residential-costsegregator Promo Code: Underground2025 LinkedIn: linkedin.com/in/jasonmelillocpa Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Un...
Send a text Episode Resources: Email: joe@belroseam.com Coaching Class: Scott Meyers Academy Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sa...
Send a text Episode Resources: Download A Free Copy of the Book: irontoncapital.com/reunderground Email: lonwelsh@irontoncapital.com Mobile: 303 619 0633 Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights ...
Send a text Episode Resources: Email: azar@peak15cap.com Website: www.peak15cap.com Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. ...
Send a text We explore how real estate debt funds work for passive investors and why becoming a limited partner might be the smart solution for steady income without property management headaches. • Investing as a limited partner means putting your money into a professionally managed fund that lends to real estate investors • Limited partners earn consistent returns (typically 7-10% annually) without dealing with tenants, renovations, or property management • Real estate debt funds lend mone...
Send a text Episode Resources: Website: https://land-play.com 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! 🎧 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...
Send a text Elevista - Speed as a Service™ Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 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! 🎧 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 invest...
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