Real Estate Investing with RealDealCrew

Most real estate investors use AI like an upgraded Google. Lauren Lucas shows how to train it, automate lead gen, and analyze deals faster.

Lauren Lucas went from a burnt-out agent to teaching AI for real estate at more than 150 live events across the US and two other countries. In this episode she explains why your AI output sounds generic and how to train ChatGPT or Claude on your voice in under 30 minutes. She also walks through the ManyChat comment-to-DM funnel that booked 200+ consultations in a year, with 187 showing up. And she makes the case that anyone...

Ashley Romiti explains how a 1031 exchange into a Delaware Statutory Trust (DST) lets landlords sell, defer the taxes, and go fully passive.

Ashley underwrote over $500 million in real estate as a commercial broker before moving to the DST side, and today she helps 1031 investors stop being landlords without giving up the tax deferral. We cover what a DST is, how it lets you close in days instead of fighting the 45-day identification deadline, and why some deals carry a 30% fee load. She also shares the questions to ask any DST advisor and explains why younger investors still...

Raising capital for real estate? Jeffrey Fidelman explains why investors pass on your first deal and fund your second.

Jeffrey Fidelman has spent more than 12 years helping companies and real estate sponsors raise capital, and his team’s in-house fundraising CRM just launched as its own software, Fundex. He breaks down why first-time sponsors fail when they try to raise for a single SPV on a 30 to 60 day close, and why fundraising really runs three to nine months. He also shares how a real estate private equity fund raised close to $150 million in about nine months after lo...

Is the 95% laundromat success rate real? Ken Wimberly of Laundry Luv explains why laundromats aren't passive income and what the numbers really say.

Ken Wimberly is a former top Keller Williams commercial agent who got into laundromats while leasing out a shopping center in Abilene, Texas. He opened his first store right before COVID and now runs Laundry Luv, a franchise building large-format, staffed, full-service laundromats in B and C class shopping centers. Ken breaks down the most quoted stat in the industry, what it really costs to open a store, and the systems that...

Raise capital first, win the deal second. Ken Gee explains how he buys Florida apartments without being the highest bidder.

Ken Gee is a former Deloitte CPA and commercial lender who now runs KRI Partners, a multifamily company with apartments across Florida, all managed from Cleveland. He explains why he flipped the usual syndication model and raises the money before he finds the deal, which lets him win properties without paying the most. He also shares how a $500 car service got Florida brokers to take an out-of-state buyer seriously, and how running a flight school taught him...

George Hanna raised $1M in his first free workshop. Here’s how real estate investors raise private money by building trust before they pitch.

Most real estate investors try to raise capital by meeting strangers one on one and pitching the deal. George Hanna, founder of Smart Income Lifestyle, built trust first through free weekly workshops, then raised around $1 million in his first real estate investing session and up to $5 million after that. He explains why teaching before you sell kills the deal, the 7 hour rule for turning a stranger into an investor, and why AI only sc...

California landlord attorney Niv Davidovich explains how landlords win in tenant-friendly cities, from screening to rent control to finding deals.

Niv Davidovich runs a law firm that represents only landlords, with a litigation practice focused on Southern California. In this episode, he explains why some California cities are far tougher on landlords than the rest of the state, why tenant screening is the best way to stay out of court, and how local rent control rules can change from one side of a street to the other. He also shares where he sees opportunity in a discounted...

Stewart Heath lost 200 units in 2008 by trusting the bank. Now he buys only boring, stabilized commercial real estate.

Stewart Heath is a CPA with more than 35 years of experience and a returning RealDealChat guest. Before 2008 he owned about 200 units across Nashville and Franklin, Tennessee, and he let his lenders' approval stand in for his own underwriting. Today his firm buys only stabilized medical office, suburban office, and mixed-use properties along the I-65 corridor from Nashville to Birmingham, using fixed-rate debt and a simple motto: boring is beautiful. He and Jack cover what 2008 taught him, why deals still...

Banks have earned 13 to 18% on unpaid property taxes for 100 years. Here's how tax liens work.

Every year, over $20 billion in property taxes goes unpaid in America, and investors buy billions of that debt from counties as tax liens. The returns are strong and secured by real estate, but 50 different state rulebooks have kept the game mostly in the hands of hedge funds and banks.

Stephen Morel is a 20-year title attorney out of New Orleans. After Hurricane Katrina flooded his home, he built a title insurance program that put roughly 12,000 abandoned properties back into productive...

Bob Knakal has closed $25 billion in NYC real estate by doing less. Here's how saying no built his career.

After 43 years brokering New York real estate, two firings from the biggest firms in the business, and a fresh start with BKREA in 2024, Bob Knakal sold 43 properties for $1.8 billion in his first full year back on his own. He joins Jack to break down why narrowing your focus beats chasing every deal, and how proprietary information and relentless fundamentals create an edge nobody can copy.

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AI is cutting white-collar jobs fast. Dustin Heiner explains why rental cash flow is now a must.

After 20 years of telling people they should invest in real estate, Dustin changed his message. With AI layoffs hitting tech, bookkeeping, and customer service, he now says you must. Dustin has been "successfully unemployed" for 10 years, owns 30+ single-family rentals and roughly 1,000 apartment units, and made more money during the 2008 crash than before it. He and Jack get into why cash flow holds up when jobs and markets don't, and why most people who buy rentals are running a hobby, not...

Your rental equity might be earning 2%. Chris Lopez explains when to sell, 1031, or redeploy it.

Chris Lopez ran a Denver investment brokerage doing $100 million a year in transactions and built Property Llama, software that helps landlords decide what to do with rentals they already own. He walks through the zero-down condo he 1031'd into a fourplex for 5X the cash flow, why he later sold his rentals (and their sub-4% mortgages) to invest in real estate lending funds, and the simple test every landlord should run before renewing a lease.

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Most commercial real estate deals don't die on the numbers. Here's what actually kills them.

Richard Crouch has spent 25 years on the legal side of commercial real estate at Woods Rogers, working with first-time commercial buyers and large syndication sponsors alike. He walks through why slow turnaround erodes confidence in a deal, what off-the-shelf operating agreements leave out, and how to protect your due diligence period before you sign.

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Brent Stewart spent 20 hours a week for four months testing AI, and says refusing to use it is the real liability.

Brent Stewart has practiced law for 30 years in Rock Hill, South Carolina, fighting insurance companies as a trial lawyer. He also owns the office buildings his own firm rents. Over the last four months he set aside 20 hours a week to work through every legal AI system he could find, and he came out of it with a position most people do not expect from an attorney: the people refusing to learn these tools are the...

Cost segregation is not just for big buildings. Joe Viery on what a single family study really costs.

Joe Viery has been running cost segregation studies since 2007 and founded US Tax Advisors Group in 2016. He has completed studies in all 50 states, and his argument in this conversation is direct: the strategy investors assume is reserved for downtown office towers now works on a fourplex or a single family rental, and most owners have never heard of it because their accountant doesn't know it is available at that price point.

Joe walks through what a study...

Aprile Osborne closed 4 deals with buyers she never spoke to until the showing. Her AI did the rest.

Will AI replace real estate agents? Aprile Osborne has sold real estate for nearly 25 years, holds Florida's record for the most new construction homes sold in a single year, and says the answer is no, but agents who ignore AI will be replaced by the ones who use it. She shares how her AI assistant nurtured leads for months and booked showings on its own, and why she sees AI as the bait that brings clients to you face...

A NASA engineer turned realtor breaks down the AI stack behind 140 deals and $100M in Denver sales.

Juan Munoz spent six and a half years on the International Space Station program at NASA, with stops at Boeing and Sierra Space along the way, before walking away to sell real estate in Denver. More than 140 transactions and $100 million in volume later, he still runs the business like an engineering project: reverse engineer the outcome, automate the repeatable parts, and delegate anything outside the top 20 percent of his value.

In this episode he walks through what is...

Wes Rowlands manages $630M and says most goals fail before they even start. Here's why.

Wes Rowlands grew up broke, raised by a single mom on nine dollars an hour, and now manages over $630 million in assets across three investment firms. In this conversation he breaks down the framework he uses to decide which goals are actually worth pursuing, why he tells people to join five teams instead of hand-picking five mentors, and why real estate, private business, and public companies are the only three asset classes he trusts for the long term.

Wes also...

A real estate broker built a brokerage with zero agents, powered entirely by AI, in one week.

Jon Berryhill is a former Army infantry sergeant and law enforcement officer who became a five-company entrepreneur and now runs a land and residential real estate operation with 52 agents. In this episode, Jon breaks down the AI-powered brokerage he just launched with zero human agents, which pulled in $50 million in potential listings in its first week. He also gets into the 30/60/90 day planning system he uses instead of long-term goals, the consistency framework behind his Agent Blueprint playbook, and how...

Rod Khleif is buying assisted living buildings at $40,000 a room. Replacement cost is $250,000.

Rod Khleif lost $50 million in 2008 when a cross-collateralized package of 800 houses pulled his multifamily portfolio down with it. He rebuilt. His students now collectively own more than 305,000 units.

In this conversation Rod walks through what he is buying right now, and the math is hard to believe until he shows it. He has two assisted living memory care facilities closed and five more under contract across San Antonio, Houston, and Dallas, at $40,000 per unit. Replacement cost on those same rooms runs $250,000 to $350,000...

Your business is not your retirement plan. Amelia Misenheimer on what to build instead.

Most businesses close, they don't sell. That's a hard thing to hear if you've spent a decade pouring every spare dollar back into the company and calling it a retirement strategy.

Amelia Misenheimer comes from three generations of real estate, starting with a grandfather who was a dry land farmer in New Mexico and ended up holding tens of thousands of acres. She built her own rental portfolio, ran a property management company with over 450 properties, and bought investment property in...

A private lender who's closed 2,000+ deals explains why 100% funded deals are the riskiest move.

Jeff Cichocki has closed over 2,000 real estate deals as a private lender and coach, and he's spent years watching guru culture push investors toward 100% funded, no money down deals. In this episode, he explains why that's backwards, why having skin in the game is what actually builds trust with a lender, and how a lack of it is quietly draining private lenders across the country right now.

Jeff also walks through a real cost comparison between hard money and private capital...

A six-figure income didn't save his marriage, so this investor rebuilt everything from scratch.

Jason Wojo cleared six figures his first year flipping houses, and it still cost him his marriage. He ended up selling his house and living on an air mattress in one of his own rehabs. That collapse forced him to rethink how he ran his business entirely, and the result became his book, Business for Life. In this conversation, Jason and Jack talk through what financial freedom actually means, why hustle culture quietly wrecks the things that matter most, and the exact framework...

A $250M NYC broker admits her team has no CRM, and explains why psychology closes deals instead.

Ashley Reidy Quinn is a partner at Asset Advisory Team in New York City, where she and her business partner Nick Montalbano have closed over a quarter billion dollars across Manhattan, Brooklyn, and the Hamptons. She started in the industry at 22 with a psychology degree and no real estate background, won her firm's Deal of the Year in her first year, and has spent the twelve years since building a six person team from scratch.

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A broker doing more than one deal a day on why busy isn't the same as making progress.

Patrick Southern is one of the highest volume real estate brokers in New Jersey, closing 376 transactions last year while also building and repositioning multifamily development projects across the state. In this conversation, he walks through what it actually takes to build for a market that hasn't arrived yet, why municipal delays and affordable housing mandates are reshaping what gets built, and the mindset shift that separates agents who stay busy from agents who actually move forward.

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Sellers can legally hide foundation cracks and structural damage. Here's how to catch it first.

Jeff Emalaba is the founder of InvestFusion and a 20+ year real estate investor and licensed agent in North Carolina. After losing $11,175 on a duplex with hidden foundation and structural issues, he built an AI-powered platform that pulls appraisal reports, inspection history, and government data most tools can't touch, then scores any property go or no go in under 60 seconds.

In this episode, Jeff breaks down the "no representation" loophole, the legal mechanism that lets sellers withhold known defects from buyer...

Senior housing is 500,000 units short of demand by 2030, and most investors don't see it coming.

Jerry Vinci has spent twenty years in senior living sales, marketing, and operations. He now runs Norden Advisory, an independent diagnostic firm that gives investors and operators a read on whether a senior housing community can actually sustain occupancy, instead of relying on the seller's own numbers.

In this episode, Jack and Jerry break down why 2026 is the real turning point for senior housing demand (it's the first year baby boomers start turning 80, the actual average move-in age, not 65), and...

Matthew Teifke lost $4 million on one bad bet, then rebuilt to a $120 million real estate portfolio.

Summary:

Matthew Teifke started buying real estate at 18, built a property management company managing 780 single family homes with his wife, and has scaled to over $120 million in assets across single family, multifamily, and commercial. On this episode, Matthew opens up about losing $4 million on a bad bet outside real estate, what that loss taught him about forcing deals into existence, and how to spot a bad business partner before you ever sign an agreement. He also breaks down renegotiating...

Rod Santomassimo says half of commercial brokers could vanish in 5 years, and he's already using AI to prove it.

Rod Santomassimo is the founder of the Massimo Group and a five time bestselling author. His newest book, Selling Buildings, was co written with Bob Knakal, the most prolific commercial building broker in US history. In this conversation, Rod and Jack cover both sides of a sale: what investors are quietly leaving on the table when they sell, and how fast AI is reshaping who does the work of brokerage itself.

Rod walks through the "vanity...

Developer John McNellis says passive real estate investing doesn't exist, and he explains why.

Summary:

John McNellis has developed close to 100 properties over more than 45 years, shifting from a corporate lawyer to a shopping center developer to, today, a specialist in small quick-serve restaurant ground leases with tenants like Chick-fil-A. In this conversation he walks through the two mistakes that wipe out most beginning developers, the deal that nearly cost him everything, and why he thinks the phrase "passive real estate investment" is one of the biggest lies in the business. He also breaks down...

The mortgage-to-rent gap just hit a level we've never seen, and it's created a permanent renter class.

Neal Bawa returns to RealDealChat for a round two conversation on where the housing market is really headed in 2026. He breaks down why the gap between the median mortgage payment and median rent has never been wider, not even during the 2006 bubble, and why that gap has split the country into two permanent housing classes: an 18-million-family renter nation and 30 million homeowners locked into mortgages they can't afford to give up. Neal also shares his 12-month home price forecast, where...

One buried line in a certificate of insurance turned two claims into million dollar problems.

Kristen Nunnery has spent sixteen years in insurance, risk management, and compliance, and she's the founder of Illumend AI, a platform built to catch hidden risk in third party insurance before it becomes a lawsuit. Most real estate investors and property managers assume that if a vendor or tenant is "licensed and insured," they're covered if something goes wrong. Kristen breaks down why that assumption is often false, walking through a real client story where two separate claims each topped a million...

Nathan Jameson explains why manufactured housing is America's most under-built asset class.

Jack sits down with Nathan Jameson, founder of Arx Capital, to unpack why manufactured housing, RV parks, and self storage have become some of the most durable, under-built asset classes in real estate, even as the residents who need this housing most often get the worst financing available to them.

Nathan explains how Arx buys existing mobile home communities, removes obsolete homes, brings in new ones, and repositions neglected properties for the long term. He also breaks down the operational mistakes he sees...

Tykr founder Sean Tepper on why most investor accounts stall at $5K, and the system that gets people past it.

Sean Tepper is the founder of Tykr, a tool that turns stock picking into a simple green, gray, or red signal. Jack and Sean dig into why the average brokerage account sits around $5,000 while the average Tykr account is over $120,000, and why Sean is convinced the real gap is confidence, not intelligence or luck. They also cover the 4M framework for evaluating a stock, how Tykr avoided the GameStop and AMC meme stock traps, and what it...

A storage unit rent hike turned airline pilot Ryan Gibson into a 90-property self storage operator.

Ryan Gibson spent 20 years flying for the airlines before a frustrating experience as a storage unit renter sent him down a different path. Today he co-runs Spartan Investment Group, a 90-property, 7.5 million square foot self storage portfolio spread across 15 states, making it the 29th largest operator in the country. In this conversation, Ryan and Jack dig into why storage demand holds up in good times and bad, why Ryan refuses to leverage past 55% on a deal even when the market rewards...

A 45-year mobile home park operator on why institutional funds won't touch his deal size, and why that's the edge.

Summary:

Ali Vahdat is an eighth-generation commercial real estate operator who has spent over 45 years buying, operating, and now exiting mobile home parks and manufactured housing communities, almost entirely across California. In this conversation, Ali explains the exact deal size where institutional capital stops looking and smaller operators can't scale, why the old rule that you have to start in residential before commercial doesn't hold up, and how a vertically integrated dealer arm turns vacant...

A 20-year mortgage lender explains how investors can qualify for loans using rental income alone, no tax returns required.

Dante Royster has spent over two decades in mortgage lending, the last several years focused specifically on real estate investors. In this episode, he breaks down what changed in lending after interest rates doubled in late 2022, why roughly one in four transactions today are investor deals, and how DSCR loans let investors qualify off rental income alone. He also shares the honest answer to what lie most investors tell themselves about having a real strategy.

Key...

Why do successful investors stall right before their next level? A hypnotherapist explains the psychology.

High performance hypnotherapist Paul Salter joins Jack Hoss to break down why so many driven investors hit an invisible ceiling right as they're about to reach the next level, and why it has nothing to do with strategy. Paul spent 17 years coaching Olympic athletes, weight loss clients, and now high-performing entrepreneurs and investors, using hypnosis to uncover the beliefs quietly running the show underneath ambition and hustle.

They cover the upper limit problem, why tying your identity to your deal...

Half of senior living inventory is obsolete. David Bacon shows how to invest in fixing that for $10.

Jack Hoss talks with David Bacon of Worthy Wealth about a real estate niche most investors overlook, senior living. Ten thousand baby boomers turn 65 every single day, senior living centers are already sitting at 90% occupancy, and nearly half the existing inventory is functionally obsolete. David explains how Worthy Wealth buys underperforming senior living centers at a discount, modernizes them, and targets a 15% annualized return through a platform where shares start at $10 with no accreditation required. He also breaks down Worthy...

Robert Howell turns $20K land deals into new manufactured homes for first-time buyers.

Robert Howell runs a land home package business, buying raw land and putting brand new manufactured homes on it, structured to qualify for conventional HUD, VA, or USDA financing. He started with a $10,000 house in Memphis and no real estate background, and has grown to 50 deals last year with 100 planned this year. In this conversation, Robert breaks down how the land home model works, why he holds mobile home parks separately for long term, tax advantaged income through cost segregation, and how he thinks...