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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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Episodes
  • How to Build AI Agents That Fix Themselves When Something Goes Wrong ft. Keith Gillespie

    How to Build AI Agents That Fix Themselves When Something Goes Wrong ft. Keith Gillespie
    May 28 2026
    This week I'm joined by Keith Gillespie, founder of Ray Automated, a Marine Corps veteran who spent eight years on active duty across 13 countries, missing the births of both his kids, and came home with one obsession: building a real estate investing business in 1 to 2 hours a day. That constraint forced him to build SOPs that became systems, systems that became software, and software that 5 years ago became Ray Automated, a three-pillar platform combining education, CRM, and coaching for investors under 50 deals done on their own.What started as a personal solution has grown into a fully commercialized system running 24 AI agents, pushing 24 to 70 software updates per day, and built on the philosophy that education alone gets 99% of people nowhere unless the tools and support are right there alongside it. Keith is one of the few people in this industry who has genuinely melded the methodology with the machine, and this conversation gets into exactly how he did it.Episode Timeline & Highlights[0:49] – Jordan introduces Keith Gillespie from Ray Automated and previews the Ray Tech Unlocked event in Dallas and his upcoming AI book[3:42] – Keith's background as a real estate investor for 10 years across 34 states, and how Ray Automated was built to solve his own problem[4:22] – What active duty Marines life actually looked like: 13 countries in 8 years, missing both kids' pregnancies, and needing to build a business in 1 to 2 hours a day[5:47] – The three pillars of Ray Automated: education, software, and coaching, and how they work together as a system[7:08] – How the Marine Corps OODA loop (Observe, Orient, Decide, Act) transfers directly to real estate negotiation and relationship management[10:45] – The grit and tenacity piece: why embracing the suck from military training carries into every hard stretch of building a business[11:12] – Jordan parallels the OODA loop to the flight training acronym DODAR and why slowing down leads to better decisions than reactive action[13:34] – Why Keith built Ray Automated as a true ecosystem rather than a CRM with coaching bolted on, and what being the company he wished existed ten years ago actually means[14:25] – Keith's 57 completed real estate investing courses and what he learned by going through virtually every major program in the industry[15:16] – Why education alone fails 99% of the time and why the fishing pole analogy captures everything wrong with most real estate programs[16:38] – Why all three pillars are non-negotiable and what happens when any single ingredient is pulled from the cake[20:02] – The two things any SaaS business actually needs to survive: results and customer service, and how Keith built Ray Automated around both[22:39] – Inside the AI agent build pipeline: discovery, internet research, planning, build, testing, human QA, and production, all in about 50 minutes per feature[25:36] – How Ray Automated scaled from 6 AI agents to 24 and why parsing agents to narrow, specific jobs improves quality at every level[26:27] – The self-healing agent approach: agents required to update their own project instructions when they learn something new[28:14] – Building a support ticket rewriter agent to fix poorly worded user requests before they reach the development queue[34:16] – Who Ray Automated is built for: any investor who has done fewer than 50 deals independently, from zero to experienced acquisition managers[35:53] – Why 389 built-in automations and everything under one roof is the real differentiator, not any individual feature[37:36] – Zero customer churn since public launch in March 2026, and what a nine-person human staff plus 24 AI agents means for responsiveness5 Key TakeawaysSystems Before Scale — Keith built the foundation of Ray Automated out of necessity, not ambition. With only 1 to 2 hours per day to work his real estate business while on active duty, every SOP had to be airtight. The constraint forced better engineering than most funded teams ever produce.Education Without Execution Is Worthless — After completing 57 real estate investing courses, Keith's conclusion is clear: knowledge without a system to apply it and support to keep you accountable is just expensive entertainment. All three pillars have to exist together or the whole thing falls apart.The OODA Loop Works Off the Battlefield — The Marine Corps' observe-orient-decide-act decision framework isn't just for room clearing. It's a real-time relationship and negotiation tool that helps you read a situation, adjust, decide, and act in a loop rather than reacting impulsively and blowing the deal.Agent Quality Comes from Narrow Scope — Ray Automated's AI infrastructure improved dramatically when they stopped asking agents to do multiple things and started assigning each one a single, tightly defined job. The more focused the scope, the higher the output quality, and the easier it is to diagnose what breaks.The Answer Is Yes — ...
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    41 mins
  • Why Self-Storage Is the Most Underrated Asset Class in Real Estate Right Now ft. Bree Hartman

    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.
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    34 mins
  • Why AI Adoption Is No Longer Optional for Real Estate Investors ft. Steve Trang & Stephanie Betters

    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.
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    33 mins
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