That Real Estate Tech Guy

Jordan Samuel Fleming
  • 5.0 (2)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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. 1D AGO

    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

  2. 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

  3. 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

  4. 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

  5. FEB 12

    Seven Steps to Building Predictable Deal Flow ft. Zachary Beach

    In this episode, I sit down with Zachary Beach, CEO of Smart Real Estate Coach and longtime real estate investor, to unpack one of the most relatable entrepreneurial journeys we’ve had on the show. Zach went from bartending and personal training to building a scalable real estate investing company alongside Chris Prefontaine — and the transition wasn’t accidental. We dive deep into the real shift that happens between doing your first deal and deciding you’re actually going to build a business. Zach shares how mastering seller communication, systemizing follow-up, and thinking in scalable processes — not just transactions — allowed him to go from side hustle to multiple deals per month. This conversation is packed with practical insight for anyone trying to leave their W2 job, scale past their first few deals, or stop being the bottleneck in their own business. Episode Timeline & Highlights [0:00] – Introducing Zachary Beach and his journey from bartender to full-time investor. [2:58] – Why social skills don’t automatically translate to phone skills — and what actually matters. [4:27] – The three-part structure of a high-converting seller call: introduction, clarification, and permission. [6:13] – Why asking hard questions builds trust faster than avoiding them. [9:01] – Motivation discovery and why most investors never dig deep enough. [12:59] – Zach’s first creative deal and the mindset shift that followed. [15:08] – Moving from getting paid for hours to getting paid for results. [18:29] – The early follow-up system using physical 1–31 folders. [21:23] – Why the fortune truly is in the follow-up — and why most people still avoid it. [24:38] – Transitioning from paper systems to CRMs like Podio and beyond. [27:01] – The seven steps to a “taken” and building predictable deal flow. [29:50] – Delegation vs. doing everything yourself — the doctor’s office analogy. [33:19] – Building a team that operates in systems, not personalities. [35:23] – Zach’s free book offer and the three-paydays strategy. 5 Key Takeaways Your first deal creates belief — not mastery. The real shift happens when you decide to build systems, not chase transactions.Seller communication is a skill, not talent. Structure beats charisma on the phone.Follow-up is a system problem, not a motivation problem. If it’s not automated or scheduled, it won’t happen.Scaling requires duplication. You must extract knowledge from your head and embed it into process.Money flows to results, not effort. Transitioning from hourly thinking to outcome thinking changes everything. Links & Resources Free Book – Real Estate On Your TermsGet Zachary’s bestselling book and learn how to create three paydays on every deal: ThreePaydaysBook.comSmart Real Estate Coach – Creative financing training and mentorshipSmrtPhone – 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 someone who’s stuck between their first deal and their first scalable system. The shift from operator to business builder starts with mindset — and then it’s reinforced with systems. More high-impact conversations coming next.

    37 min

  6. FEB 5

    Why Disposition Deserves as Much Attention as Acquisition ft. Tim Street

    Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! This episode is a big one for anyone who flips houses or plans to exit properties in the next 6–12 months. I’m joined by Tim Street, also known as the “FSBO Guy,” and this conversation is all about disposition — the most overlooked (and often most expensive) part of real estate investing. Tim makes a compelling case for why investors are often far more qualified than they realize to handle the selling side of their own deals. We break down the myths around needing an agent, the real reasons investors lose tens of thousands of dollars on exits, and how tighter markets demand tighter execution. From pricing strategy and inspections to psychology, urgency, and transparency, this episode is packed with practical tactics that can dramatically increase your net profit. Episode Timeline & Highlights [0:00] – Introducing Tim Street and why this episode focuses on disposition, not acquisition. [1:35] – Why investors are often more informed than many real estate agents. [3:55] – The power of leverage: why saving $3k on a sale can mean $30k on your next deal. [5:18] – The three common investor exits and where Tim’s approach fits best. [6:42] – Why flippers and buy-and-hold investors benefit most from controlling the sale. [7:35] – The myth that selling a home requires a law degree. [9:03] – The two biggest fears investors have when selling themselves: pricing and legal risk. [9:26] – Why underpricing is safer than overpricing in today’s market. [10:16] – The real reason FSBO lawsuits happen (and how to avoid them). [11:57] – Why investors obsess over acquisitions and ignore the part where the money is made. [13:08] – How tighter markets eliminate sloppiness and punish bad exits. [15:08] – A-player markets and why optimization now matters more than ever. [23:29] – Using AI and better copy to make listings emotionally compelling. [24:16] – The invite-only neighborhood open house strategy. [27:33] – Turning neighbors into your best sales force. [29:16] – Creating urgency through exclusivity and strict offer deadlines. [34:48] – Reduced-commission agent options when FSBO isn’t a fit. [36:03] – Why disposition deserves as much attention as acquisition. 5 Key Takeaways Disposition is where profit is made or lost. You can’t afford to treat it as an afterthought.Investors are more capable than they think. Selling isn’t magic — it’s process and preparation.Transparency removes buyer leverage. Pre-list inspections and open-book pricing change the game.Tight markets punish sloppy exits. Every mistake now shows up in your net profit.Saving money on the sale compounds forward. Small wins on exits fuel bigger future deals. Links & Resources FSBO Readiness Quiz – Find out if selling yourself is right for you👉 https://foolprooffsbo.com/quiz7-Day FSBO Launch Blueprint (Free eBook)👉 https://foolprooffsbo.com/ebookInvestor Power Pack👉 https://foolprooffsbo.com/investorsSmrtPhone – 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 focused on acquisitions but hasn’t yet optimized their exits. In this market, selling smarter isn’t optional — it’s survival. More high-signal conversations coming next.

    37 min

  7. JAN 29

    How to Raise Private Money Without Begging or Pitching ft. Jay Conner

    Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! This week’s episode is a deep, practical dive into private money, and I’m joined by Jay Conner, one of the most respected educators in the space and someone who has raised millions of dollars for real estate deals without ever chasing banks or hard money lenders. Jay breaks down private money in a way that removes the mystery, fear, and emotion that stops most investors from ever using it. We talk through when investors should start raising private money (hint: much earlier than most think), how to structure deals so lenders are protected, and why the math — not motivation — determines whether a deal works. Episode Timeline & Highlights [0:00] – Introducing Jay Conner and why private money changed everything for his business. [1:40] – Why this episode focuses more on real estate fundamentals than pure tech. [2:34] – Jay’s early years relying solely on banks — and the 2009 shift to private money. [3:45] – Raising over $2M in less than 90 days without pitching deals. [5:08] – When investors should start using private money (even beginners). [7:27] – Thinking of private money as a personal line of credit. [8:04] – Why lenders want their money deployed and are waiting for your call. [8:33] – Why private money works best for fix-and-flip and asset-backed deals. [9:25] – Walking through a real flip example using private money. [12:06] – Jay’s maximum allowable offer formula explained step by step. [13:34] – Why math removes emotion from offers. [14:39] – Adjusting formulas based on market price points. [16:13] – Leveraging past success and partnerships when you’re new. [18:29] – Why private money is asset-backed and protects lenders. [21:31] – Why the SEC doesn’t regulate single-asset private money deals. [22:59] – Jay’s Private Money Academy and how beginners get started. [24:10] – Monthly coaching, deal reviews, and live Q&A for members. [24:59] – Jay’s bestselling book Where to Get the Money explained. [25:27] – Two free tickets to Jay’s live private money conference. [27:00] – Where AI fits — and doesn’t fit — in deal analysis and underwriting. [36:55] – Why consistency beats charisma every time. [38:25] – How to claim Jay’s free resources and connect with him. 5 Key Takeaways Raise the money before you need it. Private money works best when there’s no desperation.Math beats emotion. If the numbers work, the deal works — period.Private money is asset-backed. Lenders are protected by the property, not your promises.Beginners can raise private money. Past success, partnerships, and integrity matter more than deal count.AI supports experience — it doesn’t replace it. Use technology with guardrails, not blind trust. Links & Resources Private Money Academy – First month free at jayconner.com/trialFree Book: Where to Get the Money – Autographed copy + 2 conference tickets: jayconner.com/bookSmrtPhone – The only phone system built for real estate investors (5,000 free minutes)ThatRealEstateTechGuy.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 tired of letting capital limit their growth and ready to approach funding with clarity and confidence. More high-impact conversations are coming next.

    40 min

  8. JAN 22

    How to Build Systems to Run A Remote Real Estate Investing Business ft. Nick Lamagna

    Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! In this episode, I’m joined by my good friend Nick Lamagna, host of the A Game Podcast and one of the most eclectic, disciplined, and grounded investors I know. This conversation goes far beyond real estate and turns into a deep dive on performance, mindset, and what actually separates people who last from those who burn out. Nick shares his unconventional journey into real estate, how an early setback forced him into remote investing long before it was popular, and why fundamentals always matter more than hype. We talk about building buy boxes through action, learning markets by doing deals, and why chasing “shiny” strategies is usually the fastest way to stall out. Episode Timeline [0:00] – Introducing Nick Lamagna and his background as a high performer across multiple disciplines. [1:52] – Why principles of success are universal — and why most people don’t apply them. [2:37] – Nick’s early move into remote investing out of necessity, not trend-following. [3:58] – Starting in competitive markets with no money or credit and being forced to adapt. [5:17] – Discovering that the entire country can be your buy box. [6:05] – Why cheap properties often come with expensive problems. [7:12] – The danger of buying “cash flow on paper” without performance reality. [8:44] – Finding the balance between affordability, stability, and appreciation. [14:05] – Why surrounding areas benefit when people get priced out of cities. [15:10] – Sticking to sensible parameters instead of chasing shiny wins. [16:15] – Building buy boxes by throwing a wide net and learning through offers. [17:45] – Training agents and teams by giving real feedback through reps. [19:01] – Why confidence comes from action, not theory. [21:19] – The danger of “one-strategy-only” thinking for newer investors. [23:08] – Fundamentals never change, regardless of market cycles. [29:27] – “Have bad days, not bad deals” — addressing issues immediately. [31:02] – Using video, accountability, and systems to manage properties remotely. [33:44] – Discipline over ego: lessons from jiu-jitsu, boxing, and business. [36:05] – Why effort is the real secret behind “effortless” success. [38:49] – Technology improves visibility, but discipline must come from the operator. [42:22] – Nick’s podcast, community, and why he focuses on high performers across industries. [45:39] – How to connect with Nick and collaborate on future deals. 5 Key Takeaways Fundamentals always win. Markets, tools, and strategies change — principles don’t.Remote investing works when systems replace proximity. Visibility beats geography.Cheap deals often hide expensive problems. Performance matters more than price.Technology is an equalizer, not a substitute for discipline. Tools only work if enforced.High performers share the same habits across every field. Effort creates “effortless.” Links & Resources The A Game Podcast – High performers across real estate, sports, and businessNickLamagna.com – Podcast links, socials, and resourcesSmrtPhone – The only phone system built for real estate investors (5,000 free minutes)ThatRealEstateTechGuy.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 someone who’s building remotely, scaling intentionally, and committed to mastering the fundamentals. More high-signal conversations with real operators are coming next.

    49 min
See All (50)

Ratings & Reviews

5
out of 5
2 Ratings

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
    50
  • Rating
    Clean
  • Copyright
    © 2026 smrtStudio Global, Inc
  • Show Website
    That Real Estate Tech Guy