3,000 Flips, Zero Tech Background: How Robbie Crager Uses AI to Scale

3,000 Flips, Zero Tech Background: How Robbie Crager Uses AI to Scale

Robbie Crager bought his first house at 25 with no money, bad credit, and no idea what he was doing. He had just lost a corporate job and had watched Carlton Sheets on late-night television promise he could buy a house with no money down. So he found a wholesaler in the newspaper, contracted the house, and jumped in with both feet while everyone around him begged him not to. Twenty-eight years and thousands of flips later, he calls it one of the best deals he ever did. This week on Real Estate Underground, Ed Mathews sits down with Robbie, the operator behind The FlipFlop Flipper, to talk about what it actually takes to run a lean flipping business at scale. Robbie spent two decades buying a couple of houses a week at Florida foreclosure sales. When the auctions moved online and margins got squeezed, he relocated to the island of Puerto Rico and started buying what locals call zombie houses: abandoned homes with no doors, no windows, no power, and nothing but upside. He renovates them back to the point where a first-time buyer can get an FHA loan, then hands over the keys. What you will learn: Why a 28-year operator who does not even carry a laptop has his team using AI every day, and why he believes anyone who refuses to learn it will be left at a disadvantage. The three-question filter Robbie runs before entering any new market: will our money go further, can we make a bigger return, and will our impact be one we are proud of. The single biggest mistake of his career, flipping a thousand houses before 2007 and keeping none of them, then losing everything in the crash. How he rebuilt by partnering with people who had capital instead of borrowing hard money, and started investing for cash flow instead of chunks of money. And the closing-table moment that still makes every renovation worth it. Robbie also shares the story behind a little red brick house in Ukraine. On a humanitarian trip in 2022 he helped a pastor buy a home big enough to adopt three boys out of an orphanage. That same house now shelters and feeds 70 orphans. As Robbie says, every house has a story, and that one is pretty good. The lightning round covers the joy of missing out, why he says no to most deals that cross his desk, the book he has read front to back five times, and how he defines success now that boats and fast cars stopped mattering. If you are an operator trying to build something that lasts, this one is full of hard-won lessons from someone still in the work. Find Robbie inside his free FlipFlop Flipper community on Skool, or on YouTube. Chapters 00:00 The leap of faith: no money, bad credit, no clue 00:59 Welcome to Real Estate Underground 02:14 28 years, thousands of houses, and Puerto Rico zombie homes 03:33 You don't have to stay in a broken system 04:07 Quitting at 25 and the Carlton Sheets first deal 06:40 Scaling to a couple of houses a week for 20 years 08:47 Using AI every day in a lean flipping business 10:32 The markets: Florida, the online shift, and Puerto Rico 11:23 The three-question filter for entering a new market 13:12 Investing with impact and the Ukraine orphanage house 17:44 Working with his son McKenna in the business 21:31 The deal you don't do: the joy of missing out 23:43 Purpose, legacy, and what gets him out of bed 26:11 The free FlipFlop Flipper community 26:46 The biggest mistake: flipping everything, keeping nothing 29:30 Lightning round: books, success, and travel 32:47 Where to find Robbie This week's book: Think and Grow Rich by Napoleon Hill https://www.amazon.com/Think-Grow-Rich-Publication-Foundation/dp/193787950X?tag=clarkstholdin-20 [https://www.amazon.com/Think-Grow-Rich-Publication-Foundation/dp/193787950X?tag=clarkstholdin-20] More Real Estate Underground episodes: clarkst.com/podcast [https://www.clarkst.com/podcast] Elevista: elevista.com/podcast [https://www.elevista.com/podcast] Elevista - Speed as a Service™ [https://www.elevista.com] Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: * Clark St Capital [https://www.clarkst.com] -> Passive real estate investments for busy business owners and executives * Elevista [https://www.elevista.com/underground] -> AI SaaS for real estate investors * Clark St Academy on YouTube [https://www.youtube.com/@clarkstacademy] -> Learn how to invest in real estate Social Media: * LinkedIn [https://www.linkedin.com/in/edmathews] -> Ed Mathews (President at Clark St and Elevista) 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!

Detroit's Comeback: Turnkey Cash Flow in America's Most Undervalued Market

For the 200th episode of the Real Estate Underground, the conversation lands on a city near and dear to Ed's heart: Detroit. His guests are James Lloyd and Voytek Mardula of US Properties [https://usproperties.ca], a Toronto-based team that has spent ten years building a full turnkey operation on the ground in Michigan. The thesis is contrarian and simple. While most people wrote Detroit off, James and Voytek heard it was in the early innings of recovery, drove down to see it for themselves, and found architecturally beautiful colonials in strong historic neighborhoods trading below the cost of construction. They sold off assets elsewhere, including a primary residence, and bought heavy. Ten years and 600-plus renovated homes later, they run a system that takes an investor from a first phone call to a cash-flowing landlord in 30 to 45 days. This episode is a practical map of remote and cross-border investing. You will hear how they vet a property with a 300-point pre-purchase inspection and block-level analysis, how a foreign national forms a US entity to qualify for financing, and why they refinance instead of flip to scale a portfolio. Voytek breaks down Detroit's 55,000-room hotel shortage against 17 million annual visitors and how that gap feeds their short-term rental strategy. Then the pair walk through the tax stack: opportunity zones that can wipe out capital gains after ten years, and bonus depreciation that can cover a down payment in year one. The Final Five turns personal: working alongside a lifelong best friend, the books that shaped them, and Voytek's deep dive into AI, which he calls the single most revolutionary tool of his lifetime. Find them at USProperties.ca [https://usproperties.ca]. Chapters 00:00 The most undervalued market in the country 01:00 Welcome to the Real Estate Underground 02:00 Meet James Lloyd, Voytek Mardula, and US Properties 03:00 Why Detroit: the contrarian comeback thesis 05:00 Buying the right house in the right neighborhood 08:00 Managing a remote portfolio with a local team 11:00 The investor journey from first call to cash flow 13:00 The full turnkey system, step by step 14:00 Foreign nationals and US entity formation 16:00 Buy, hold, and refinance to scale 18:00 Short-term rentals and Detroit's hotel shortage 22:00 Opportunity zones and bonus depreciation 26:00 The auto industry and tech sector renaissance 31:00 The final five 32:00 What gets them out of bed 36:00 A decision they would take back 37:00 AI obsession and the book on the nightstand 40:00 Defining success and life off the clock 42:00 How to reach US Properties This week's book: You to the Power of Two: Redefining Human Potential in the Age of AI by Joseph Bradley and Don Tapscott [https://www.amazon.com/You-Power-Two-Redefining-Potential/dp/1637747845?tag=clarkstholdin-20] More Real Estate Underground episodes: clarkst.com/podcast [https://www.clarkst.com/podcast] Elevista: elevista.com/podcast [https://www.elevista.com/podcast] Elevista - Speed as a Service™ [https://www.elevista.com] Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: * Clark St Capital [https://www.clarkst.com] -> Passive real estate investments for busy business owners and executives * Elevista [https://www.elevista.com/underground] -> AI SaaS for real estate investors * Clark St Academy on YouTube [https://www.youtube.com/@clarkstacademy] -> Learn how to invest in real estate Social Media: * LinkedIn [https://www.linkedin.com/in/edmathews] -> Ed Mathews (President at Clark St and Elevista) 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!

Tom Dunkel's SAFE Method: Vetting Every Deal Before You Invest

If you are within three feet of Ed Mathews, you are probably talking about real estate. This week the conversation is with Tom Dunkel, managing principal at Eagle Capital Investments [https://www.investwitheagle.com], and it is a clinic in how to vet a deal before a dollar leaves your account. Tom has been a full-time investor for two decades. Over that span he has raised more than $50 million in private capital from a network of investors who lean on his experience to place money into alternatives most people never see: multifamily, self-storage, mobile home parks, medical office, and private lending. His pitch is simple. Real diversification is not large cap versus small cap or value versus growth. It is owning assets that do not move when a headline does. As Tom puts it, a tsunami hitting Japan can knock the stock market down 15 percent overnight, but it does nothing to an apartment building in Phoenix or a storage facility in North Carolina. The backbone of the episode is Tom's SAFE Investing Method, the same screen he uses every day. S is for sponsor: who are you writing the check to, what is their track record, and have you earned the right to ask the hard questions. A is for asset: if you cannot explain the investment to your kid or your elderly parent, you do not understand it well enough to fund it. F is for financials: do the projections hold up, and has this sponsor actually hit numbers like these before. E is for exit: you cannot click your way out of a syndication on a Tuesday afternoon, so you need to know exactly what has to happen, and over what time horizon, before your money comes back. Then Tom goes off the mainstream script on taxes. The standard advice is to 1031 exchange again and again until you die and hand your heirs a stepped-up basis. Tom's question is blunt: do you really want to be managing properties at 90 the way his mother could be. He prefers the lazy man's 1031, taking the gain, then using fresh depreciation from the next deal to shelter income, all without the rigid timelines and same-title rules that make a true 1031 nearly impossible across a group of 20 or 30 investors. Pay the freedom tax, he argues, and buy yourself passive income and time. The buy box conversation is just as practical. Tom likes private lending for first-position security and monthly checks. He likes mobile home parks and co-living because they answer the housing affordability crisis with real, unsubsidized supply, and he breaks down how a Philadelphia operator turns a $1,000 row home into $3,000 a month by renting furnished rooms to tenants on fixed income. He covers where self-storage sits after its boom and consolidation, and why he treats it like multifamily underwriting now. On technology, Tom is candid that he is still early but already getting leverage from AI. His current workflow is to go back and forth with Claude to build a long, specific prompt, then hand it to Manus for deep research on a market like Phoenix multifamily. He even has an AI clone at tomdunkel.ai [https://www.tomdunkel.ai] that will answer your investing questions, as long as you do not bring up the Eagles. The lightning round digs into purpose beyond family, the best advice he ever got from a nine-figure investor, a job he probably should have turned down, and how he defines success now as an empty nester: geographic and time freedom, plus the room to give back through Tunnel to Towers and a scholarship he started for a friend lost to ALS. Find Tom at investwitheagle.com [https://www.investwitheagle.com], grab his book The Wealth Builder's Playbook, or talk to his clone at tomdunkel.ai [https://www.tomdunkel.ai]. Chapters 00:00 Don't let the tax tail wag the freedom dog 01:00 Meet Tom Dunkel and Eagle Capital Investments 03:00 Why true diversification lives outside the stock market 04:00 The SAFE Investing Method: Sponsor, Asset, Financials, Exit 08:00 Taxes and the lazy man's 1031 exchange 13:00 The Wealth Builder's Playbook and being the "who" 17:00 The buy box: mobile home parks, co-living, multifamily 22:00 Where self-storage sits after the boom 24:00 Using Claude and Manus to move faster 27:00 Lightning round: purpose, significance, and legacy 30:00 The best advice he ever got 33:00 A decision he would take back 34:00 On the nightstand: Invest Like a Billionaire 36:00 Defining success as an empty nester 38:00 Golf, a rock and roll cover band, and where to find Tom This week's book: Invest Like a Billionaire: Unlocking the Wealth Secrets of the Ultra-Rich by Bob Fraser and Ben Fraser https://www.amazon.com/dp/B0F3W2SNDS?tag=clarkstholdin-20 [https://www.amazon.com/dp/B0F3W2SNDS?tag=clarkstholdin-20] More Real Estate Underground episodes: clarkst.com/podcast [https://www.clarkst.com/podcast] Elevista: elevista.com/podcast [https://www.elevista.com/podcast] Elevista - Speed as a Service™ [https://www.elevista.com] Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: * Clark St Capital [https://www.clarkst.com] -> Passive real estate investments for busy business owners and executives * Elevista [https://www.elevista.com/underground] -> AI SaaS for real estate investors * Clark St Academy on YouTube [https://www.youtube.com/@clarkstacademy] -> Learn how to invest in real estate Social Media: * LinkedIn [https://www.linkedin.com/in/edmathews] -> Ed Mathews (President at Clark St and Elevista) 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!

B-Class Property, A-Class Management: The Short-Term Rental Edge with Tim Hubbard

Short-term rentals are supposed to be the most hands-on asset class in real estate. Tim Hubbard runs hundreds of them across the U.S. and multiple countries—without ever being on the ground. Tim is the CEO and co-founder of Corzly [https://corsley.com], the virtual management company he built after 16 years of operating his own short-term rental portfolio from outside California, then outside the U.S. entirely. His team handles pricing, listings, guest communication, and back-end operations across Eastern Europe, South Africa, the Philippines, and South America—while the owner still controls the housekeepers and maintenance on the ground. In this episode, Tim and Ed get into why “a B-class property with A-class management beats an A-class property with B-class management,” why the urban short-term rental market is more durable than the vacation-rental crowd realizes, and what the data is actually telling operators about which markets to enter and which to avoid. What you’ll hear: * Why the “can’t be hands-on AND remote” constraint is the forcing function that built Corzly—and what it means for any operator stuck in their own business * The buy box: how Tim underwrites a short-term rental like an apartment building, what data sources actually matter, and the regulatory gotchas that kill deals * Why urban short-term rentals quietly outperform vacation markets—more reasons to stay, less seasonal volatility, and the medical-professional and conference angles most investors miss * The lightning round: under-budgeting renovations, Dennis Waitley’s “two choices” framing, and why education became Tim’s purpose once the portfolio could run itself Books Tim recommended: * Who Not How [https://www.amazon.com/dp/B08JJ7P6QF?tag=clarkstholdin-20] by Dan Sullivan and Dr. Benjamin Hardy—the framework for finding the right people to delegate to * The Slight Edge [https://www.amazon.com/dp/1626340463?tag=clarkstholdin-20] by Jeff Olson—Tim’s most-recommended book; the case for compounding small daily disciplines About Tim Hubbard: CEO and co-founder of Corzly. 16-year real estate operator. Host of Short Term Rental Riches, a six-year-old podcast covering virtual STR management, market selection, and the operational discipline behind scaled portfolios. Find Tim: corsley.com [https://corsley.com] | Short Term Rental Riches podcast (all platforms + YouTube) Subscribe to Real Estate Underground for weekly conversations with operators who’ve been through the cycle and lived to talk about it. Elevista - Speed as a Service™ [https://www.elevista.com] Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: * Clark St Capital [https://www.clarkst.com] -> Passive real estate investments for busy business owners and executives * Elevista [https://www.elevista.com/underground] -> AI SaaS for real estate investors * Clark St Academy on YouTube [https://www.youtube.com/@clarkstacademy] -> Learn how to invest in real estate Social Media: * LinkedIn [https://www.linkedin.com/in/edmathews] -> Ed Mathews (President at Clark St and Elevista) 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!

From X Games Gold to 3,300 Multifamily Units with Dan Brisse

What does it take for a professional snowboarder, six X Games appearances, gold and silver medals, fifteen years on tour, to land in real estate? For Dan Brisse, the answer was watching the guys five and ten years ahead of him lose their houses, their cars, and worse. That was the wake-up call. While most of his peers spent every pay raise on the biggest house they could buy, Dan was reading books and buying apartments. By the time his snowboarding career ended, he had 70-some units already producing passive income. Today Dan co-leads Granite Towers Equity Group, a 3,300-unit multifamily portfolio focused on Dallas-Fort Worth, Nashville, and select Minnesota submarkets. The playbook is disciplined: newer assets (1985 and up), 140 to 300 units, $20 to $40 million purchase price, 95%+ occupancy submarkets with real pent-up demand. Eighty-twenty split with LPs. Sixty-five to seventy-five percent loan-to-value, fixed rate, non-recourse. CapEx raised liquid up front, so the bank cannot force a bad spend. What you'll hear: * The chairlift moment that reframed every financial decision Dan has made since * Why 78% of pro athletes are broke within three years of retirement and the side-hustle move he made to avoid joining them * The Cleburne, Texas case study: $6.75M acquisition, $2.1M LP raise, full-cycle returns * A second case study where interior upgrades and water conservation drove a 1.8x equity multiple in two years * Why Dan believes we are in a generational buying window with multifamily trading at 30-40% discounts versus 2021-22 peaks * His sharpest definition of wealth, and why "rich" and "wealthy" aren't the same thing Learn more about Granite Towers Equity Group: https://www.granitetowersequitygroup.com/contact-us [https://www.granitetowersequitygroup.com/contact-us] Elevista - Speed as a Service™ [https://www.elevista.com] Elevista Connect is the first AI-powered lead conversion system built for real estate investors. 🎧 Subscribe to Real Estate Underground for weekly insights on building wealth through real estate, without sacrificing your sanity. Additional Resources: * Clark St Capital [https://www.clarkst.com] -> Passive real estate investments for busy business owners and executives * Elevista [https://www.elevista.com/underground] -> AI SaaS for real estate investors * Clark St Academy on YouTube [https://www.youtube.com/@clarkstacademy] -> Learn how to invest in real estate Social Media: * LinkedIn [https://www.linkedin.com/in/edmathews] -> Ed Mathews (President at Clark St and Elevista) 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!