That Real Estate Tech Guy

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.

  1. 3H AGO

    How to Build a 90% Passive Rental Portfolio That Runs Itself ft. Martine Richardson

    In this episode, I sit down with Martine Richardson from The Freedom Inc., and this one goes in a direction we haven't covered before on this podcast — rentals. Martine started as a wholesaler, stumbled into her first rental by accident, and never looked back. She's closed over 100 deals, built a portfolio that covers all her expenses, and now helps investors buy their first or next rental with little to none of their own money. We get into the mindset shift from active income to passive wealth, why investing a little more upfront in your properties saves you years of headaches, and how to get started in rentals even in today's market. If you're a wholesaler thinking about making the leap into buy-and-hold — or just looking for a smarter long-term play — this episode is for you. Episode Timeline & Highlights [0:52] – Introducing Martine Richardson and The Freedom Inc. [1:10] – How Martine got her first rental by accident — and why it changed everything. [3:43] – From wholesaling to 100+ deals and why passive income became the goal. [4:36] – Why wholesalers should be thinking about rentals right now. [5:23] – The mindset shift from high-paying job to true time and money freedom. [6:00] – Bought for $35K, now worth $240K — letting the asset do the work. [6:40] – Why rental properties win even as wholesaling faces more regulatory pressure. [7:17] – The 90% passive model and what systems make that possible. [29:54] – How Martine got into coaching and why she got a coach before becoming one. [30:45] – Why she charges for coaching — and why free is often lazy. [33:13] – The free Freedom Inc. community: what's in it and who it's for. [34:16] – Why wholesalers should know about buy-and-hold buyers in her community. [35:25] – How to join the free community and apply for a strategy session. 5 Key Takeaways Rentals create freedom. Wholesaling creates a job. If time freedom is your goal, the asset has to do the work — not you.Invest a little more upfront. Replacing the aging water heater before a tenant moves in buys you years of problem-free ownership.Little to no money down is possible. With the right strategy and creative financing, your first rental doesn't require a massive cash outlay.Systems make it passive. It's not 100% hands-off, but the right systems get you to 90% — and that changes your life.Credibility comes from doing it first. Work with coaches and mentors who've actually lived the path they're teaching. Links & Resources The Freedom Inc. – Free community for rental property investors 👉 Join on Facebook: search "The Free To Me"Strategy Session – Map out how to buy your first or next rental with little to none of your own money 👉 strategy.thefreetome.comThatRealEstateTechGuy.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 a wholesaler who's been grinding hard but hasn't made the move into passive income yet — because the asset can do the work, but only if you let it. More high-signal conversations coming next.

    37 min

  2. APR 2

    What a 300 Deal a Year Phone Sales Machine Actually Looks Like ft. Tiffany High

    In this episode, I sit down with Tiffany High from Heel's Homes and Results Driven ROI — and this one is packed. Tiffany and her husband Josh do 300+ deals a year as active investors while also coaching experienced real estate investors on how to build serious phone sales teams. She knows exactly what it takes to scale, and she holds nothing back here. We dig into why so many investors underestimate their phone system, how Tiffany went from 12 unproductive salespeople to 8 who produce four times the revenue, and why she believes sales is a science — not an art. If you're building a phone team or thinking about scaling your acquisitions operation, this episode is a masterclass. Episode Timeline & Highlights [0:41] – Introducing Tiffany High and her two businesses: Heel's Homes and Results Driven ROI. [1:29] – Why technology has been the single biggest game changer in Tiffany's business. [2:38] – The moment Tiffany realized her phone system was killing her team's productivity. [4:00] – Letting go of three fourths of her staff and rebuilding the right way. [4:37] – How 8 salespeople now outperform what 12 used to do — and why. [5:22] – Why sales is a science, not an art — and what that means for scalability. [6:15] – Call audits: what they are and why every phone sales team needs them. [6:38] – The whisper feature: how to coach your team live without the seller hearing a word. [7:02] – Live transfers vs. appointment setting and why appointments are costing you millions. [23:06] – Why AI tools need to be part of your phone sales infrastructure now. [29:24] – What Tiffany wishes she knew when she started: leadership can't be outsourced. [30:34] – Culture drives results — and it starts and ends with you as the leader. [32:13] – The three technology products every new real estate investor should implement first. [33:43] – Why building a custom CRM from day one is worth every penny. [34:26] – How to connect with Tiffany and apply to work with Results Driven ROI. 5 Key Takeaways Your phone system is your most important tech investment. If your team is still hand dialing, you're leaving productivity and revenue on the table.Sales is a science. Build a repeatable, coachable process and scalability becomes infinite.Live transfer beats appointment setting every time. Stop scheduling callbacks and start closing in the moment.Leadership cannot be outsourced. You can duplicate technology overnight — you can't duplicate the ability to lead people.Culture is your number one priority. People quit managers, not companies. Build an environment people want to stay in. Links & Resources Results Driven ROI – Coaching for experienced real estate investors building phone sales teams 👉 tiffanyhigh.comTiffany High – Instagram: @tiffanyhighofficial | Josh High – Instagram: @joshhighofficialSmartPhone – The only phone system built for real estate investorsThatRealEstateTechGuy.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 struggling to get productivity out of their phone team — because the fix usually isn't the people. It's the system. More high-signal conversations coming next.

    36 min

  3. MAR 26

    Why Most Investors Get Voice AI Wrong Before They Ever Turn It On

    Hey, it's Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! This one is a solo episode, and I'm diving into something I just finished that I'm genuinely fired up about — a three-day Voice Accelerator Challenge we ran with over 230 real estate investors. No guest today, just me breaking down what we covered, what questions came up, and why I think most people are still thinking about AI in completely the wrong way. We go deep into the mindset shift that has to happen before any AI implementation works, why treating agents like labor instead of software changes everything, and how we walked investors through deploying a live inbound acquisitions intake agent during the challenge. If you're curious about voice AI but still on the fence — or if you've tried it and it hasn't clicked yet — this episode is going to reframe the whole thing for you. Episode Timeline & Highlights [0:00] – Solo episode intro and why Jordan just ran a three-day Voice Accelerator Challenge. [1:12] – 230+ attendees and the core questions investors had about voice AI. [2:02] – Why Day 1 started with mindset — and why that surprised people. [3:00] – The problem with the "AI as a tool" mentality and why it limits your results. [4:39] – Agents vs. software: the fundamental difference in how you should think about AI. [5:21] – What separates a real voice agent from a fancy answering service. [5:52] – The hiring analogy: why you'd never hire a person without a role — and shouldn't hire AI that way either. [6:54] – SmartPhone's Agent Recruitment Center and the role-based approach to AI. [9:18] – What these agents are fully trained on: acquisitions, exit strategies, and REI methodology. [23:06] – Hallucinations, trust, and why properly built agents don't go off the rails. [24:11] – Why intake agents are explicitly blocked from making offers — and why that matters. [26:40] – The compounding power of a 24/7 agent that never has a bad day. [27:10] – What every missed call is really costing you in a high-sales business like real estate. [27:39] – Why the acquisitions intake agent was the first role in the challenge. [28:39] – Never miss another inbound call again — and why that changes your whole perspective. [29:08] – What's next: running the challenge again and how to get involved. [29:48] – How to connect with Jordan and get started with SmartPhone. 5 Key Takeaways Mindset comes before implementation. If you still see AI as a tool to turn on and off, you'll never get the real value out of it.Agents are labor, not software. Think roles, responsibilities, and outcomes — not features.Role-based agents outperform generic ones. Trained, bounded agents with clear job descriptions produce far better results.Every missed call is money left on the table. In real estate, unanswered inbound calls are one of the most expensive silent killers in your business.Boundaries protect you. Agents that know what they can't do are just as important as agents that know what they can. Links & Resources SmrtPhone – The only phone system and voice AI platform built for real estate investors 👉 smartmophone.ioVoice Accelerator Challenge – Follow Jordan on Instagram, Facebook, or YouTube to get notified when the next challenge runsThatRealEstateTechGuy.com – All episodes and exclusive tech discountsClosing If you enjoyed this episode, please follow, rate, and review That Real Estate Tech Guy. Share it with an investor who's curious about voice AI but hasn't made the leap yet — because the mindset shift is the hardest part, and this episode will help them get there. More high-signal conversations coming next.

    32 min

  4. MAR 19

    How AI Is Changing SEO Faster Than Most Investors Realize ft. Glen Petersen

    In this episode, I sit down with Glen Petersen from Bateman Collective, and this one turned into a full-on masterclass in digital marketing for real estate investors. Glen brings years of high-level PPC and SEO experience, including managing massive ad spend and working directly with Google — and he breaks down what’s actually happening behind the scenes in today’s marketing landscape. We go deep into why so many investors fail before they even get started with PPC and SEO, not because the channels don’t work, but because their business isn’t ready to support the leads. We unpack the real role of data, why speed-to-lead is one of the most underrated drivers of ROI, and how AI is quietly reshaping both paid and organic search. If you’re thinking about scaling your marketing or want to stop wasting money on leads you don’t convert, this episode is packed with practical insight. Episode Timeline & Highlights [0:00] – Introducing Glen Petersen and Bateman Collective’s focus on PPC and SEO for real estate investors. [3:16] – From traditional marketing to digital and why attribution changed everything. [6:57] – Why PPC costs are rising and what’s really happening behind the scenes with Google. [8:16] – Cost per lead vs cost per acquisition and why most investors track the wrong metric. [9:56] – Why Bateman turns clients away who aren’t operationally ready. [13:16] – Demand generation vs demand capture and why messaging must change. [13:31] – Speed-to-lead and why delayed response kills deals instantly. [15:11] – Real examples of answering leads instantly vs sending them to voicemail. [16:27] – Tracking beyond the lead and identifying breakdowns in the funnel. [18:16] – Using data feedback loops to improve Google’s algorithm performance. [25:41] – How AI is accelerating SEO results faster than traditional timelines. [26:32] – Real example of 25% of SEO revenue coming from AI-driven discovery. [27:19] – AI ads, ChatGPT search, and the future of paid acquisition channels. [29:39] – When investors should start PPC and SEO in their business journey. [30:30] – Why SEO is a long-term play but creates massive ROI over time. [34:33] – The importance of consistency in marketing and avoiding “shiny object syndrome.” [36:11] – The 3–6 month learning phase most investors underestimate. [36:41] – Who Bateman Collective works best with and how to get a free audit. 5 Key Takeaways Your business must be ready before your marketing works. Leads are useless without systems, follow-up, and speed.Speed-to-lead is everything. The first conversation often wins the deal.Track beyond the lead. Revenue and conversion data matter more than cost per lead.AI is accelerating search and discovery. SEO is evolving faster than ever before.Consistency beats experimentation. Marketing works when you commit long enough to let it compound. Links & Resources Bateman Collective – PPC, SEO, and digital marketing for real estate investors: https://batemancollective.comFree PPC & SEO Audit: https://get.batemancollective.com/rlpSmrtPhone – 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 investor who’s spending money on marketing but not seeing results — because most of the time, the problem isn’t the leads… it’s what happens after they come in. More high-signal conversations coming next.

    39 min

  5. MAR 12

    Why Creative Finance is No Longer Optional in Today's Real Estate Market ft. Joe & Jenn Delle Fave

    Joe started with a borrowed cassette tape course in 2000. Jenn was a middle school teacher going into debt. When they met in 2008, they began buying junkers, slowly stacking deals, and figuring out creative finance when the banks tried to cap them at ten mortgages. In 2020, Covid forced the leap to full time — and they never looked back. Today they run a thriving portfolio, a coaching community, and a life built around family and freedom. No flash. Just discipline. Episode Timeline & Highlights [0:00] – Introduction to Jen and Joe and what makes their story different. [3:00] – How a teacher and a car dealership finance manager found each other and real estate. [4:35] – Joe's first deal: $12,000 profit from a borrowed cassette tape course. [5:52] – Building slowly with BRRRR before it had a name. [6:12] – The 2016 turning point: banks threaten to cap mortgages, creative finance enters the picture. [6:33] – How Covid became the catalyst to go full time. [10:10] – Joe on why "real wealth is silent" — and why the backyard office beats the Lambo. [12:24] – How technology enabled virtual deals during Covid — and changed everything. [18:35] – What drove them from investors to coaches: authentic sharing and organic demand. [22:08] – The "cheat code": Joe's deal knowledge + Jen's teaching ability = a community that actually works. [28:42] – Why creative finance is no longer optional in today's market. [30:04] – A current deal: turnkey house, $5,000 down, 3.25% rate, cash flowing from day one. [31:37] – The lease option model: renters paying 20–30K upfront and multiple six-figure exits. [32:14] – The full wealth-building path: wholesale → keep the good ones → lease option → 1031 → scale. 5 Key Takeaways Creative finance is a must-have tool. Seller financing and lease options let you buy houses others can't — at prices that actually pencil out.Slow and steady builds real wealth. Joe and Jenn layered knowledge and deals methodically. The foundation is what lasts.The best coaches are still in the game. Their community grew because client results were real — not because of a big profile.Technology removes all excuses. You can buy, manage, and close deals in states you've never visited. The barrier is mindset.The lease option is an underused wealth multiplier. Big upfront deposits, strong cash flow, and 1031 exits compound fast.Links & Resources Creative Finance Playbook – Free Facebook group with Q&A and deal breakdownsCreativeFinancePlaybook.com – Free tools to find leads and talk to sellerssmrtPhone – The only phone system built for real estate investors (5,000 free minutes)ThatRealEstateTechGuy.com – All episodes and exclusive tech discountsClosing If this episode resonated, please follow, rate, and review That Real Estate Tech Guy — and share it with someone still waiting for the "right time" to get started. Discipline will always beat flash.

    39 min

  6. MAR 5

    Why AI Should Be Treated as Labor Not Just Another Tool

    This week’s episode is a little different. It’s just me. I’ve been speaking at several events recently and noticed that one idea keeps resonating with people over and over again — the idea that AI shouldn’t be viewed as software, but as labor. Most businesses today are experimenting with AI tools, but very few have actually made the mindset shift required to unlock its real potential. In this episode, I break down why the real transformation happening right now isn’t about shiny tools or clever prompts — it’s about redefining how work gets done inside your business. AI is no longer just something that helps your team work faster. It’s something that can share responsibility for output alongside your team. We dig into how the evolution from SaaS software to AI agents is changing the structure of businesses, why most companies are still thinking about AI the wrong way, and how role-based AI workers can dramatically increase production without dramatically increasing headcount. If you’re a real estate investor or entrepreneur trying to scale without constantly hiring more people, this episode will challenge how you think about the future of your workforce. Episode Timeline & Highlights [0:00] – Why this episode is a solo talk based on presentations Jordan has been giving recently. [1:09] – The core idea: AI should be viewed as labor, not just software. [2:05] – Why most businesses are still thinking about AI in the wrong way. [3:06] – The “shiny tool” problem and why real estate investors are especially prone to it. [5:42] – A quick historical look at how labor and production have evolved. [6:40] – How SaaS changed business productivity over the last 30 years. [9:41] – Why SaaS systems increased efficiency but still relied on human execution. [10:12] – The next shift: AI systems that can share responsibility for output. [11:59] – How traditional CRMs hit a ceiling because humans must still execute tasks. [12:38] – AI agents as workers that can perform roles inside a business. [14:31] – How Smart Agents were designed around roles instead of generic tools. [22:00] – A real example: four contracts generated from after-hours AI responses. [23:17] – Why urgency and speed-to-lead are critical in real estate investing. [24:37] – The opportunity created by 24/7 lead response. [27:16] – Where AI agents work best: repetitive, high-volume operational roles. [28:28] – How businesses that adopt AI labor models will outpace competitors. 5 Key Takeaways AI is not just a tool — it’s a workforce multiplier. Businesses need to treat it as labor, not software.The SaaS era increased efficiency, but AI changes output itself. Systems can now participate in execution.Role-based AI wins. Treat AI agents like employees with defined responsibilities.Speed matters in real estate. AI answering leads instantly can unlock deals humans miss.Start small. Introducing one AI role into your workflow can transform your productivity. Links & Resources SmrtPhone – The only phone system built for real estate investors (5,000 free minutes)Smart Agents – AI workforce tools built into the SmartPhone platformThatRealEstateTechGuy.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 someone who’s experimenting with AI but hasn’t yet made the mindset shift from tools to workforce. Because the businesses that understand this shift early will build a massive advantage in the years ahead.

    31 min

  7. FEB 26

    How to Scale Flips Across Multiple States Without Losing Control ft. Bobby Triplett

    This week, I sit down with Bobby Triplett, Senior Vice President of Renovations at Offerpad, and we go deep into one of the most overlooked but critical parts of real estate investing — renovations at scale. Bobby oversees renovation operations across 15 states and 20+ markets, managing hundreds of projects per month. We talk about what it actually takes to build a consistent, high-performance renovation machine across multiple regions, why most contractors struggle with accountability, and how speed — not just cost — is the real lever that protects profit in today’s market. If you’re flipping houses, expanding into new markets, or frustrated with unreliable contractors, this episode will completely shift how you think about execution, leadership, and operational consistency. Episode Timeline & Highlights [0:00] – Introducing Bobby Triplett and Offerpad’s renovation footprint across the country. [3:19] – How Offerpad evolved from iBuyer to nationwide renovation service provider. [5:08] – Scaling to 1,200+ flips per month and what that taught the team about systems. [7:27] – Why no two homes — or markets — are the same. [9:18] – Leadership summits, shared scars, and building a culture of accountability. [11:16] – Why tech investment often ignores renovations — and why that’s a mistake. [14:17] – Standardization vs. local market nuance in construction. [16:34] – Radical transparency with contractor scorecards and performance metrics. [18:46] – Creating accountability without yelling and chaos. [23:36] – Speed vs. cost vs. quality — and why Bobby bets on speed. [24:41] – Paying contractors fast to build loyalty and priority. [27:53] – Who Offerpad serves best — mid-sized operators and serious flippers. [29:28] – Enabling remote investing with trusted boots on the ground. [31:01] – Institutional-level renovation services without institutional overhead. [33:08] – The Days Per Thousand (DPT) metric and controlling project timelines. [34:36] – Why today’s tighter market punishes sloppy execution. [36:41] – Building investor confidence through consistency and delivery. 5 Key Takeaways Speed protects profit. The longer a project drags, the more risk and holding costs eat your margin.Standardization scales, but local expertise wins. 80% process, 20% market nuance.Transparency drives performance. Scorecards and accountability conversations matter.Pay fast, expect excellence. Strong contractor relationships are built on trust and consistency.Remote investing only works with reliable execution. Acquisition and disposition are easy — swinging hammers is not. Links & Resources Offerpad Renovations – Nationwide renovation services across 15 statesConnect with Bobby Triplett – LinkedInSmrtPhone – 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 investor who’s ready to expand markets, tighten execution, and stop letting renovations be the bottleneck in their business.

    39 min

  8. FEB 19

    How 5,000 Units Exposed the Real Problem in Property Management ft. Tim Bratz

    This week I’m joined by Tim Bratz, real estate investor, operator, and now software founder of Smart Management. Tim has built, scaled, pivoted, and rebuilt multiple times on his entrepreneurial journey — and this episode dives into every arc. From starting in real estate in 2007 right before the crash, to rebuilding after going broke, to scaling nearly 5,000 units, and now launching a disruptive property management platform, Tim’s story is anything but linear. We talk about resilience, market cycles, bad partnerships, scaling teams, and the reality that success is rarely one straight line. Then we shift into the real pain point that sparked his latest venture: third-party property management and outdated software systems that quietly destroy asset value. If you own rentals, operate multifamily, or care about protecting NOI in today’s market, this episode is a must-listen. Episode Timeline & Highlights [0:00] – Introducing Tim Bratz and the multi-arc entrepreneurial journey. [3:19] – Getting started in real estate in 2007 and surviving the crash. [4:54] – Buying rentals at the bottom of the market in Cleveland. [6:27] – Discovering the power of multifamily efficiency. [7:27] – Partnership challenges and pressing the reset button. [8:33] – The 2017 pivot from transactional flips to full-scale apartment acquisition. [9:48] – Scaling to nearly 5,000 doors in just a few years. [11:39] – The headwinds: interest rates, insurance spikes, supply chain chaos. [13:28] – Why bad property management evaporates more wealth than market shifts. [15:22] – The emotional rollercoaster of entrepreneurship and long-term thinking. [18:01] – Controlling what you can control in volatile markets. [21:23] – The origin of Smart Management and the engineering mindset behind it. [23:35] – The core problem: too many disconnected tech systems. [25:11] – Why legacy property management software is outdated and slow. [27:20] – Building an all-in-one “business in a box” platform. [29:16] – Real-time financial visibility vs. six-week-old reporting. [31:04] – AI automations inside property management operations. [33:53] – Automating maintenance requests and reducing overhead. [35:23] – Increasing NOI through operational efficiency and staffing optimization. [38:49] – Why this industry is primed for disruption and AI integration. [40:25] – Raising capital, scaling Smart Management, and onboarding demand. 5 Key Takeaways Entrepreneurship is not linear. Multiple resets are part of building something meaningful.Long-term thinking prevents short-term panic decisions. Control the controllables.Operational inefficiency destroys asset value faster than market shifts.Real-time data changes everything. You can’t drive forward looking in the rearview mirror.AI and automation will redefine property management economics. Lower overhead = higher NOI = higher valuation. Links & Resources Smart Management – Join the waitlist at SmartManagement.comConnect with Tim Bratz – @TimBratz on social mediaSmrtPhone – 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 investor who’s scaling rentals, frustrated with property management, or ready to think long term about building real enterprise value. More high-level operator conversations coming next.

    41 min
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About

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.

Information

  • Creator
    Jordan Samuel Fleming
  • Years Active
    2022 - 2026
  • Episodes
    54
  • Rating
    Clean
  • Copyright
    © 2026 smrtStudio Global, Inc
  • Show Website
    That Real Estate Tech Guy

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