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That Real Estate Tech Guy

That Real Estate Tech Guy

De : 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.

© 2026 smrtStudio Global, Inc
Direction Economie Management Management et direction
Épisodes
  • Using Automation vs. When to Use an AI Agent
    Oct 29 2026

    This week I’m going solo to make a case that some of the most important infrastructure in your business isn’t software, it’s your people. Your systems can move data, but they can’t understand the work, so people like a customer success rep named Mark have become the intelligent integration layer between your CRM, billing platform, Slack, and email.

    I walk through Mark’s customer request step by step, show where traditional APIs and automations stop, and explain how AI agents can move work with the right context when the movement isn’t deterministic. The goal isn’t to remove people from the business but to get them out of the infrastructure layer, and I close with an exercise to find where that’s happening in your own company. If you’re an investor or operator designing a workforce of people and AI agents, this one is for you.


    Episode Timeline & Highlights

    [0:00] – Why some of the most important infrastructure in your business is your people, not your software

    [1:00] – Moving data is not the same as understanding the work, and the customer request that shows the gap

    [1:31] – Mark opens the CRM, billing platform, Slack, product platform, and email to assemble the full picture

    [2:56] – What Mark really did: connected systems, interpreted information, and acted as the integration layer

    [5:09] – The limits of traditional integration, and a failed payment that an API can move but not understand

    [6:45] – Where deterministic movement is perfect: if X happens, do Y

    [7:50] – Systems could never answer who should receive the work, so people provided the intelligence

    [8:28] – How an AI agent handles the failed payment using customer context, policies, and its authority

    [10:21] – Moving the work with the relevant context, not a task that just says please handle

    [12:20] – Not every movement needs an agent: if X reliably means Y, use the API, automation, or rule

    [13:19] – Scale: a person monitors 50 situations while an agent can stay aware across thousands

    [14:52] – The goal is to get people out of the infrastructure layer, not out of the business

    [16:32] – A person who is the right worker for the job versus a person required to connect the work

    [17:36] – Receive, execute, hand off, and who provides the intelligence between those stages

    [19:59] – The exercise: find the people who seem to know how everything connects and watch what they do

    [21:29] – If the movement needs intelligence, could an AI agent provide it instead of a person?


    Key Takeaways

    1. People Became the Infrastructure: Your systems could move data but couldn’t understand the work, so people filled that gap.
    2. Moving Data Is Not Understanding Work: An API can tell your CRM a payment failed, but it can’t tell you what that failure means.
    3. Keep Deterministic Work Deterministic: If X reliably means Y every time, use an API, automation, or business rule instead of an agent.
    4. Agents Provide Intelligent Continuity: An agent can decide where work should go and send it along with the context the next worker needs.
    5. Get People Out of the Layer, Not the Business: People should be involved because they’re the right worker for the responsibility, not because the infrastructure can’t understand the work.


    Links & Resources

    • smrtPhone: https://www.smrtphone.io
    • That Real Estate Tech Guy: https://thatrealestatetechguy.com


    If this made you think of the Mark in your own business, spend a week watching what he actually does between your systems. You may find work that was never his job to begin with. More high-signal conversations coming next.

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    23 min
  • Why Handing Off Work Is Not the Same as Continuity
    Oct 22 2026

    This week I’m going solo to talk about the pattern underneath almost everything your business does: receive, execute, hand off. Handing work to the next person or AI agent isn’t enough, because they also need the context to continue it, and I show why with an AI customer success agent named Maya and a customer success leader named Sarah.

    We get into why access to your CRM, Slack, and email is not the same as context, how Sarah’s call with an at risk customer creates new context that has to travel back to Maya, and why a handoff and true continuity are two different standards. I also connect it to infrastructure architecture, the third pillar of the AI labor architecture framework, and close with an exercise you can run on one handoff this week. If you’re an operator or investor designing a workforce of people and AI agents, this one is for you.


    Episode Timeline & Highlights

    [0:00] – Almost all work follows one cycle: receive, execute, hand off

    [1:31] – Meet Maya, an AI customer success agent who spots a customer at serious risk of leaving

    [2:35] – Maya hands the at risk customer to Sarah, a customer success leader, with no background

    [3:35] – Sarah has to rebuild the story from the CRM, support system, billing, email, and Slack

    [4:54] – Why context is not more information, a bigger context window, or access to everything

    [6:20] – Access to the CRM is not the same as context, only the raw materials to build it

    [7:32] – The better question: what does this worker need to understand to execute this responsibility?

    [8:06] – Sarah calls the customer and creates new context: a business change and a promise by Friday

    [9:31] – When the work returns to Maya, a CRM status change is not the same as context

    [11:45] – This isn’t an AI problem, it’s a work problem: meaning gets left behind every time work moves

    [12:13] – Why so much context lives between your systems or inside your people’s heads

    [14:14] – Good infrastructure gives each worker the right context for their bounded responsibility

    [16:37] – Infrastructure architecture as the third pillar of the AI labor architecture framework

    [18:37] – The difference between a handoff and continuity

    [19:39] – The exercise: pick one handoff and stand in the shoes of the worker receiving it

    [21:30] – People inside your business have become part of the infrastructure, compensating for the friction


    5 Key Takeaways

    1. Handoff Is Not Continuity: Moving work to the next person or AI agent means little if they have to rebuild the story before they can act.
    2. Access Is Not Context: Giving a worker access to the CRM, Slack, and email only hands them raw materials to build understanding themselves.
    3. Execution Creates New Context: Every decision, conversation, and commitment made along the way has to travel forward with the work.
    4. Bounded Context Beats Total Access: Each worker needs the context that fits their responsibility, not the entire history of the organization.
    5. Follow One Handoff: Pick a single handoff in your business and look at what the receiving worker has to search for, ask, and reconstruct.


    Links & Resources

    • smrtPhone: https://www.smrtphone.io
    • That Real Estate Tech Guy: https://thatrealestatetechguy.com


    If this made you think about how work changes hands in your own business, pick one handoff this week and stand in the shoes of the person receiving it. You’ll probably find someone quietly carrying context around in their head. More high-signal conversations coming next.

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    24 min
  • How to Find Where Work Gets Stuck in Your Business
    Oct 15 2026

    This week I'm going solo to ask a question most business owners skip. You probably run a CRM, a billing platform, a support desk, and 10 or 20 other systems, so how does work actually move between them? I break down why those systems are great at storing information but terrible at moving the next piece of work, and why that gap gets exposed the moment you add AI agents to your workforce.

    I walk through a real world example with an AI customer success agent named Maya, who does her job perfectly and then hits a wall when the work needs to go to a person. From there we get into shared execution, why people like Sarah have been the invisible connective tissue in your operations for decades, and a simple exercise to find where work stalls in your own business. If you're an investor or operator thinking about AI agents, workflow automation, and business infrastructure, this one is for you.


    Episode Timeline & Highlights

    [0:00] – Why most businesses run 10 to 20 systems that store information but don't move work

    [1:06] – The real question: how does work move through your business after a status changes?

    [1:40] – Why the answer is usually manual: emails, Slack posts, and copying data between systems

    [2:57] – Why people have always been the ones moving work between your CRM, billing, and support tools

    [4:38] – Why AI agents expose an infrastructure gap that businesses were never built to handle

    [5:13] – Meet Maya, an AI customer success agent who spots a customer at risk of leaving

    [6:52] – What happens when Maya hands off the work: a task, an email, a Slack message, or a ticket?

    [8:23] – The constraint moves: AI agents become faster than the infrastructure around them

    [10:36] – Why moving data between systems is not the same as moving work

    [12:20] – Why shared execution between people, AI agents, and systems only works if work can move

    [13:28] – Islands of execution, and how Sarah's invisible work fills gaps in your architecture

    [16:10] – The infrastructure questions to ask: what triggers movement and who owns the work next

    [17:06] – The exercise: pick one piece of work and follow it across your organization

    [18:12] – The test: if the people moving this work disappeared tomorrow, would your systems know what to do?

    [19:37] – Why context has to move with the work, not just a notification


    Key Takeaways

    1. Storing Is Not Moving: Your systems record what happened, but they rarely move the next piece of work on their own.
    2. People Are the Connective Tissue: Salespeople, project managers, and coordinators have been manually carrying work between systems for decades.
    3. AI Agents Expose the Gap: A capable agent still stalls when its output has to cross a responsibility boundary by email or Slack.
    4. Move Work, Not Just Data: Syncing fields between systems is not the same as keeping execution going as work passes between people, agents, and systems.
    5. Context Travels With the Work: The next worker needs to know what happened, what was tried, and why the work moved, not just a "please handle" alert.


    Links & Resources

    • smrtPhone: https://www.smrtphone.io
    • That Real Estate Tech Guy: https://thatrealestatetechguy.com


    If this made you stop and wonder where work sits waiting in your own business, pick one process this week and follow it from start to finish. You'll probably find your own version of Sarah. More high-signal conversations coming next.

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    22 min
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