Real Estate Underground

Ed Mathews
  • 4.8 (18)
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  • UPDATED WEEKLY

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 inHow to vet opportunities when everyone else is sitting on the sidelinesConservative underwriting in markets that punish optimismSystems 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.

  1. 1D AGO

    The Lazy Investor Who Helped 2,000 People Buy Rental Properties

    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. 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 backHow to vet teams 2,000 miles away when you can't be on-siteThe $99K property that changed everything (and why fear almost killed the deal)Property managers as your best acquisition source—if you ask the right questionWhy 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 trustAre tired of real estate being a second jobNeed a framework for vetting property managersWant to hear from someone who's helped 2,000 people actually do thisNo 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. 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 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)

    42 min

  2. FEB 10

    Riding the Short-Term Lane: Kenny Bedwell’s Data-Driven Journey to STR Riches

    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 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. 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 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)

    40 min

  3. FEB 3

    AI Arbitrage: Why the Next 12 Months Will Separate Real Estate Winners from the Losers

    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 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. 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 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)

    35 min

  4. 10/07/2025

    From Contractor to Mogul: Joao Macavilca's Real-Estate Adventure

    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, 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)

    28 min

  5. 09/30/2025

    Patience Is Profit: Finding Great Deals in Today’s Real Estate Market with Mike Zlotnik

    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 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)

    37 min

  6. 09/23/2025

    How to Fund Your Real Estate Empire Without a W-2 with Jimmy Rios

    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! 🎧 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)

    39 min

  7. 09/16/2025

    From Oil Fields to Real Estate Empires with Casey Gregersen

    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 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)

    36 min

  8. 09/09/2025

    Solving Affordable Housing Through Co-Living with Sam Wegert

    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. 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)

    46 min
See All (189)

4.8
out of 5
18 Ratings

About

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 inHow to vet opportunities when everyone else is sitting on the sidelinesConservative underwriting in markets that punish optimismSystems 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.

Information

  • Creator
    Ed Mathews
  • Years Active
    2018 - 2026
  • Episodes
    189
  • Rating
    Clean
  • Copyright
    © 2026 Clark St Holdings LLC
  • Show Website
    Real Estate Underground