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That Real Estate Tech Guy

That Real Estate Tech Guy

By: Jordan Samuel Fleming
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Welcome to the only weekly podcast dedicated to the Real Estate Investing Tech Stack, hosted by Jordan Samuel Fleming. Jordan has been heavily involved in building technology tools for Real Estate Investors for over a decade, and is the Co-Founder and CEO of smrtPhone, and all-in-one cloud phone system and power dialer. If you're serious about scaling up your Real Estate Investing business then this weekly podcast is for you! You'll learn from the best as each week Jordan speaks with individual investors who have leveraged technology to scale their businesses, as well as technology companies who build the tools you use on a daily basis. That Real Estate Tech Guy brings together expert insights, advice and the latest technology tips for any investor looking to build their Real Estate Investing business.

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Economics Leadership Management Management & Leadership
Episodes
  • Why Self-Storage Is the Most Underrated Asset Class in Real Estate Right Now ft. Bree Hartman
    May 21 2026

    This week I'm joined by Bree Hartman from Storage School — and this one goes somewhere we haven't been before on this podcast. Self-storage. Bree bought her first facility while pregnant, using an SBA loan, from across the country in Louisiana. She now controls over $8 million in self-storage assets, runs a 12-month education program, and is actively acquiring more facilities while teaching her students to do the same.

    We get into why self-storage is one of the most cash-flowing, unsexy, and underrated asset classes in real estate right now, how to find mom-and-pop facilities before they hit the market, and why Bree left single family behind the moment she realized she'd need 20 rentals just to replace her income. If cash flow and time freedom matter more to you than the flashy stuff, this episode is for you.


    Episode Timeline & Highlights

    [0:42] – Introducing Bree Hartman and Storage School.

    [3:41] – Bree's backstory: W2 with Fish and Wildlife, accidental rental, and buying her first facility while pregnant.

    [5:23] – The moment she realized single family was just another job — and self-storage was the answer.

    [6:07] – No toilets, no tenants, no employees — why self-storage clicked immediately.

    [6:51] – Using an SBA loan to buy her first facility with only 10–15% down.

    [7:14] – Finding the sweet spot: mom-and-pop facilities with upside and low competition.

    [18:00] – Live screen share: how Bree actually finds off-market storage facilities using data tools.

    [26:24] – Why technology is a competitive advantage in self-storage acquisitions right now.

    [27:14] – How Storage School works: 12-month program, six-week onboarding, off-market pipeline.

    [29:38] – Reverse engineering your lifestyle first — then picking the asset class that fits.

    [30:35] – What Bree is focused on now: scaling to 6–7 new facilities and partnering with students.

    [31:47] – The international opportunity: why self-storage in Europe is 20–30 years behind the US.

    [32:30] – Why right now is buy time in self-storage — and how AI is accelerating the opportunity.


    5 Key Takeaways

    1. Self-storage cash flows where single family can't. No tenants, no toilets, no maintenance calls — just a simple, scalable model with real margins.
    2. SBA loans change the math. 10–15% down instead of 35% means you can get into your first facility without a massive capital outlay.
    3. Mom-and-pop facilities are the opportunity. Mismanaged, under-rented, and off-market — that's where the value is hiding.
    4. Reverse engineer the life first. Don't pick an asset class and then try to fit your life around it — start with what you actually want and find the vehicle that gets you there.
    5. Right now is buy time. The negotiating power is there. The technology is accelerating the opportunity. The window won't stay open forever.


    Links & Resources

    • Storage School – 12-month program to find, buy, and operate your first self-storage facility 👉 Text "SCHOOL" to (916) 579-7209
    • Free Storage Offer Calculator – Evaluate any deal with Bree's cheat code tool 👉 Link in show description
    • SmrtPhone – The only phone system built for real estate investors
    • ThatRealEstateTechGuy.com – All episodes and exclusive tech discounts


    Closing

    If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy. Share it with an investor who's grinding on single family and wondering if there's a better way — because there might be, and it doesn't involve a single toilet.

    More high-signal conversations coming next.

    Show More Show Less
    34 mins
  • Why AI Adoption Is No Longer Optional for Real Estate Investors ft. Steve Trang & Stephanie Betters
    May 14 2026

    This is a special one. I'm joined by two people I deeply respect — Stephanie Betters, CEO of Left Main REI and co-founder of Better Path Homes, and Steve Trang, founder of Objection Proof AI — and the three of us are announcing something we've been building together that I'm genuinely fired up about.

    REI Tech Unlocked. September 19th–21st, 2026 at the Hyatt Regency in Dallas, Texas. This is not another conference. It's the first real implementation event built specifically for real estate investors — a technology playground where you don't just hear about AI and the tools changing this industry, you actually sit down, get hands on, and walk out with things built and running in your business.


    Episode Timeline & Highlights

    [0:58] – Introducing Stephanie Betters, Steve Trang, and why this episode is special.

    [2:19] – Announcing REI Tech Unlocked: September 19th–21st, 2026 in Dallas, Texas.

    [2:48] – Why 2026 is a pivotal moment for real estate investors and AI adoption.

    [3:26] – The technology playground concept — hands on, not just listening.

    [4:47] – Why disconnecting from operations at an event is where real learning happens.

    [5:22] – No vendor booths, no fishbowl business cards — real companies doing real work with you.

    [6:03] – Everyone's got an idea. This event is about execution, not inspiration.

    [6:26] – Why most events leave you fired up but on your own — and how this is different.

    [25:22] – The fundamental shift happening in business right now — AI isn't a tool, it's infrastructure.

    [25:52] – The internet comparison: every business rebuilt around it. AI is next.

    [27:28] – Steve's final word: the big brands and organizations coming to the event.

    [28:51] – Stephanie's final word: execution over theory — walking out with something done.

    [29:58] – Jordan's final word: depth, hands-on implementation, and walking out configured.

    [31:40] – Event details, early bird pricing, and how to get your tickets.


    5 Key Takeaways

    1. AI adoption isn't optional. This shift is as fundamental as the internet — every business will be rebuilt around it.
    2. Information isn't the problem. Every investor knows AI is coming. The gap is implementation — and that's what this event closes.
    3. Walk in curious, walk out configured. The goal isn't motivation or mindset. It's leaving with tools running in your business.
    4. Hands on beats listening every time. Sitting down with a technology company and getting live implementation is worth more than a dozen keynotes.
    5. Execution is the idea. Everyone has a plan. The investors who win in 2026 and beyond are the ones who actually do the thing.


    Links & Resources

    • REI Tech Unlocked – The first hands-on AI implementation event for real estate investors 👉 http://reitechunlocked.com/ — Early bird tickets on sale now through May 2026
    • Left Main REI – CRM built for real estate investors 👉 leftmainrei.com
    • Objection Proof AI – AI-powered sales training and appointment scheduling 👉 objectionproofai.com
    • SmrtPhone – The only phone system built for real estate investors
    • ThatRealEstateTechGuy.com – All episodes and exclusive tech discounts

    Closing

    If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy. Share it with an investor who keeps saying they need to figure out AI — because figuring it out is exactly what this event is built to do.

    Early bird tickets are on sale now. We'll see you in Dallas.

    More high-signal conversations coming next.

    Show More Show Less
    33 mins
  • What Losing $3 Million Teaches You About Business and Life ft. Andrew Schlag
    May 7 2026

    This week I'm sitting down with Andrew Schlag from TrueCo — and this one is a little different. We still talk real estate, we still talk business, but this episode goes somewhere most podcasts in this space are too afraid to go. Andrew opens with losing $3 million — not from a bad market, but from a moment of desperation and misplaced trust — and what that brutal season taught him about the life he actually wanted to build.

    Andrew and his business partner Leo launched TrueCo around one core belief: the best life you can live shouldn't be deferred. Not until the next deal closes. Not until you hit your number. Now. We get into the psychology of the hustle trap, the eight categories of holistic success, and why the entrepreneurs who win the most often enjoy it the least.


    Episode Timeline & Highlights

    [0:42] – Introducing Andrew Schlag and TrueCo's mission around holistic wealth building.

    [3:01] – Andrew's background: country boy, construction, and finding real estate in 2014.

    [6:38] – The deal that went sideways: signing deeds without attorney approval and losing $3 million.

    [9:33] – The aftermath: $30K a month in losses, litigation, and not wanting to live anymore.

    [10:47] – How Andrew came back one day at a time — and what that season really taught him.

    [11:27] – Meeting his business partner Leo and how TrueCo was born in Barcelona.

    [13:29] – The "I'll be happy when" trap and why that goalpost never stops moving.

    [14:47] – Get the lesson faster: why reflection matters more than grinding harder.

    [15:07] – Pulling the future into the present — putting the trip on the calendar before you can afford it.

    [18:52] – Seasons of hustle vs. lifestyle hustle and why the economy rewards value, not hours.

    [19:52] – Weekly reflection, morning routines, and building intentional habits into daily life.

    [30:23] – What TrueCo actually is: holistic success, wealth building, and a life worth living.

    [32:22] – How the community works: cash vehicles, wealth building, and doing deals with people you enjoy.

    [35:40] – Who TrueCo is for and how to connect with Andrew and Leo.


    5 Key Takeaways

    1. Never sign the deeds without your attorney. Desperation is the enemy of good decisions — urgency is fine, desperation is dangerous.
    2. Stop living in the "when I get there." The goalpost never stops moving. Build a life worth living right now.
    3. Reflection is a business skill. The investors who never stop to ask why are the ones who barrel hardest in the wrong direction.
    4. The economy rewards value, not hours. Working hard is a badge of honor that pays nothing if you're creating the wrong thing.
    5. Holistic success beats financial success alone. Wealth without health, relationships, and purpose isn't winning — it's just a bigger number.

    Links & Resources

    • TrueCo – Holistic wealth building community for heart-driven entrepreneurs 👉 truecoa.com
    • Andrew Schlag – Facebook & YouTube: search Andrew Schlag
    • SmrtPhone – The only phone system built for real estate investors (5,000 free minutes)
    • ThatRealEstateTechGuy.com – All episodes and exclusive tech discounts

    Closing

    If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy. Share it with an entrepreneur who's grinding hard but hasn't stopped to ask whether they're actually happy — because the hustle isn't the problem. Deferring your life while you do it is.

    More high-signal conversations coming next.

    Show More Show Less
    38 mins
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