- 46 minutes 1 secondPlan 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 houses. Plan B is buy more land and build more houses. There is no Plan C that doesn't involve buying land.
Brandon returns to Real Estate Underground to break down how HPG Capital creates new housing neighborhoods in Nashville, why he stopped building homes but kept developing land, and how he structures deals that pay investors 18% preferred returns with no personal guarantees.
What you'll learn:
- The three phases of land development and how to profit from each one without ever building a house
- How to de-risk a deal by lining up your buyer and getting city approval before spending real money
- Why "big puzzle pieces next to small puzzle pieces" on a GIS map is the buy signal
- How he gets 20% deposits from national builders, released day one, to fund development
- Why he ditched vertical integration after hitting $22 million in annual development
- The biggest mistake he made with strategic partners and how to avoid it
- His "Body, Being, Balance, Business" framework for measuring success
Books mentioned: The Surrender Experiment and The Untethered Soul by Michael Singer
Learn land development: learnlanddevelopment.com (free 8-hour course)
Invest with HPG Capital: hbgcapital.net/waitlistElevista - 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)
5 May 2026, 4:00 pm - 34 minutes 16 secondsIt'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 and CEO of Alliance CGC, where he's built one of the most respected portfolios in the country, with deep focus on net-leased properties and medical office buildings.
In this episode, Ben and Ed cover:
- Why medical office is recession-resistant in any market (the "human body never goes out of style" rule)
- The over-leverage mistake that taught Ben the real lesson of commercial real estate
- Cash flow, tax efficiency, and long-term security as the only three goals worth chasing
- How to navigate one of the most chaotic markets in decades
- The difference between treating real estate as a commodity vs. a hard asset
- What old-school CRE investors do that the new wave gets wrong
Connect with Ben: benreinberg.com
Real Estate Underground is hosted by Ed Mathews of Clark St Capital.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)
28 April 2026, 4:00 pm - 42 minutes 28 secondsObscurity 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 with members in 65 countries and now spends most of his time helping real estate pros turn AI from a shiny object into a revenue tool. If you're still using AI to write listing descriptions and calling it a day, this one will push your thinking.
In this episode you'll learn:
- Why Clay calls obscurity, not competition, the biggest threat to any real estate business
- How the "eliminate, automate, delegate" framework turns documented processes into leverage
- Which AI tools Clay actually uses daily, and how Gemini, Claude, and ChatGPT scored in his blind writing test
- How Ed built an AI voice agent that gets a lead on the phone in 45 seconds, across five languages
- Why the Harvard 391% rule makes speed-to-lead the single biggest edge in real estate today
- How solo operators and small teams can look and act like companies many times their size
Resources Mentioned: Google NotebookLM for deal prep and process documentation. Gamma for instant presentations. ylopo for lead nurture automation.
Takeaway: AI is a force multiplier, not a crutch. It levels the playing field on access, but experience and wisdom still do the heavy lifting. Use it as the spotter at the gym, not the guy lifting the weight.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)
21 April 2026, 4:00 pm - 52 minutes 4 seconds123% 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 one of the country's fastest-growing private lending shops, and he sees the DSCR lending industry doubling in size over the next three years.
In this episode, Joel and Ed break down:
- Why investors are rotating from Texas and Florida to Ohio, Kentucky, and the Midwest
- How DSCR loans actually work (and why 1.0 coverage isn't enough)
- The real math on leverage: why the smartest investors stay at 60% LTV or below
- Why "relationship capital" matters more than real estate knowledge
- What happened when Joel wired money on March 5, 2020 and the market froze
- His $99 training modules vs. the $35K guru trap
- The best advice he ever got: "Post that in 5 years. Shut up. Go back to work."
Joel currently reads: Buy Back Your Time by Dan Martell
Connect with Joel: brrrr.com
Real Estate Underground is hosted by Ed Mathews of Clark St Capital.
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)
14 April 2026, 4:00 pm - 36 minutes 50 secondsNo 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 properties in Montenegro. His approach is the opposite of what most US investors are used to: no leverage, no perfect data, and no rushing.
In this episode, Ed and Ladislas talk about:
- Why emerging market real estate is actually a harder asset than US multifamily (and arguably less risky)
- How he evaluates a new country before putting money in (the Uzbekistan stock exchange story is worth the listen alone)
- Managing property across dozens of countries with local property managers (and why you always need a backup)
- The case for putting a small percentage of your portfolio outside the US
- How $200K in a Panama bank or $400K in Turkish real estate can buy generational citizenship and a Plan B for your family
- The Ivory Coast deal that went wrong and why you should never skip the buyer's agent
- His father's best advice: "You don't have to answer every question"
Learn more about Ladislas at The Wandering Investor and on YouTube.
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)
7 April 2026, 4:00 pm - 52 minutesFrom 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 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 TokensElevista - 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)
31 March 2026, 4:00 pm - 32 minutes 32 secondsTime, 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 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 HillElevista - 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)
24 March 2026, 4:00 pm - 37 minutes 26 secondsDead 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 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 PriceElevista - 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)
17 March 2026, 4:00 pm - 32 minutes 24 secondsThe 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, 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 2026
- How Joe acquired a property for less than the outstanding debt — and what it took to get there
- The 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 on
- Joe's personal 3.5% math: out of 140 LP deals across 50+ operators, what's actually gone to zero
- The fixed vs. floating rate lesson that still stings
- How Joe defines success — and it has nothing to do with deal count
Joe 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 PeckElevista - 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)
10 March 2026, 4:00 pm - 42 minutes 45 secondsDeal 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, 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 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)
3 March 2026, 5:00 pm - 28 minutes 35 secondsFrom 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 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 KiyosakiElevista - 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)
24 February 2026, 5:00 pm - More Episodes? Get the App