Real Estate Underground

Ed Mathews
  • 4.8 (18)
  • INVESTING
  • 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. 20H AGO

    From Gold Bricks to Gold Coins: Real Estate Tokenization with Tyler Vinson

    Send us Fan Mail 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 of only about 10 companies in the US with an SEC-registered digital broker dealer ATS license, and the only one focused exclusively on real estate. In this episode, Tyler breaks down what real estate tokenization actually is, how it enhances (not replaces) traditional syndication, and why it matters for both GPs and LPs. He explains how restricted shares can become tradeable digital assets, how non-accredited investors can participate after 12 months under Rule 144, and what the secondary marketplace looks like in practice. He also shares the personal story that became his mission: a friend from high school who wanted to invest but didn't qualify. We also get into the lessons Tyler learned from being over-leveraged during the 2008 financial crisis, his disciplined approach to education, and why the future of real estate investing is undeniably digital. What you'll learn in this episode: - What real estate tokenization is and how it works (the gold brick to gold coins analogy) - How tokenization creates a pathway to liquidity for traditionally illiquid LP positions - The SEC compliance framework: Rule 144, ATS marketplaces, and why registration matters - How non-accredited investors can access deals that were previously off limits - Why over-leverage is the #1 risk in real estate and how Tyler rebuilt after 2008 Book on Tyler's nightstand: The Power of the Subconscious Mind by Dr. Joseph Murphy Connect with Tyler Vinson and RE Tokens: - Website: retokens.com (free Quick Start Guide to Real Estate Tokenization) - LinkedIn: Tyler Vinson / RE Tokens - YouTube: RE Tokens 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial Media: LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    52 min

  2. MAR 24

    Time, Money, and the $21 Million Leap with Ashley Garner

    Send us Fan Mail 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 taught him about conservative underwriting, why his dad's "cash is king" advice saved his business more than once, and how he manages a growing portfolio with a core team of three. What you'll learn: - Why Ashley underwrites for what a property does right now, not what it could do - How flat rent growth and rising expenses are squeezing multifamily operators and what to do about it - The KPIs he tracks every Monday to keep 200+ units running - Why he's evolving from B-/C value-add to larger markets with better financing - The mindset shift that makes raising capital feel like offering an opportunity instead of asking for money - Why "if you need to raise $10 million, go ahead and raise $11" Ashley is currently raising capital for Bryn Mawr Village, a 196-unit property in Jacksonville, NC being refinanced to a HUD 223(f) loan. Learn more at abgmultifamily.com. This Week's Book: Think and Grow Rich by Napoleon Hill 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial Media: LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    33 min

  3. MAR 17

    Dead Retail, Live Returns with Neil Henderson

    Send a text 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 storage facilities. The numbers behind their model are hard to ignore. Ground-up self-storage construction runs $120-130 per square foot and takes nearly three years. Nomad's conversions come in at $60-65 per square foot, acquisition to occupancy in 12-14 months. Half the cost, a third of the time. In this episode, we get into: - Why old Kmarts and strip malls are the perfect conversion targets - How vertical integration keeps construction costs at cost-plus-12% vs the industry standard 25% - Their current deal: a 171,000 sq ft strip mall in Rocky Mount, NC for $6M with seller financing - Why 2026 loan maturities could create a wave of distressed self-storage opportunities - The Sam Zell principle that guides every acquisition: buy below replacement cost - Neil's Las Vegas condo in 2005 and what it taught him about buying when everyone else is greedy Learn more about Nomad Capital at nomadcapital.us Book recommendation: "How to Break Up with Your Phone" By Catherine Price 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)

    37 min

  4. MAR 10

    The Cincinnati Mistake That Built a $2 Billion Company with Joe Fairless

    Send us Fan Mail 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 2026How Joe acquired a property for less than the outstanding debt — and what it took to get thereThe 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 onJoe's personal 3.5% math: out of 140 LP deals across 50+ operators, what's actually gone to zeroThe fixed vs. floating rate lesson that still stingsHow Joe defines success — and it has nothing to do with deal countJoe 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. 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial Media: LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    32 min

  5. MAR 3

    Deal Junkie Diaries: Michael Pouliot Talks Strategy for 2026 and Beyond

    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 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. 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial Media: LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    43 min

  6. FEB 24

    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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial Media: LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    29 min

  7. FEB 17

    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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial Media: LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    42 min

  8. 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 executivesElevista -> AI SaaS for real estate investorsClark St Academy on YouTube -> Learn how to invest in real estateSocial Media: LinkedIn -> Ed Mathews (President at Clark St and Elevista)

    40 min
See All (195)

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
    195
  • Rating
    Clean
  • Copyright
    © 2026 Clark St Holdings LLC
  • Show Website
    Real Estate Underground

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