Real Estate Underground

Ed Mathews

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. 2 DAYS AGO

    From Prison to Paradise: Fuzzy Jardine and The Pono Way

    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 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. 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)

    29 min
  2. 17 FEB

    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
  3. 10 FEB

    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
  4. 3 FEB

    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

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.