That Real Estate Tech Guy

Why AI Is Creating Jobs Instead of Cutting Them ft. Stephanie Betters & Steve Trang

• Jordan Samuel Fleming • Season 1 • Episode 45

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0:00 | 43:48

This week's episode is a little different: instead of my usual solo takes or one-on-one interviews, I'm joined by my co-hosts on this whole project, Stephanie Betters from Left Main REI and Steve Trang from Objection Proof AI, for a three-way conversation about REI Tech Unlocked, now just a few weeks away. The three of us dreamed this event up four years ago on a boat in Jamaica, fueled by frustration that our industry, one serving more than 100,000 serious real estate investment operators, still runs on affiliate links and guru-led hype instead of a real place to evaluate technology honestly.

We also dig into something all three of us are seeing with our own clients right now: AI hasn't eliminated jobs the way everyone predicted at the start of the year, it's actually created a need for more people, because the bottleneck moves downstream once the top of your funnel gets faster. Steve shares the framework from his own book about redesigning a business around AI rather than just bolting a tool onto an analog process, and we close out by each naming the one thing we're personally most excited about at the event itself.

If you've been on the fence about coming to REI Tech Unlocked, September 19th through 21st in Dallas, this conversation is the clearest picture yet of why the three of us built it and what you'll actually walk away with.


Episode Timeline & Highlights

[0:00] – Jordan turns the tables, letting Stephanie and Steve lead the conversation about REI Tech Unlocked

[1:39] – Steve's honest take: most industry events are inspiration, not tactics, and this one is built to be different

[2:04] – Revisiting the origin story: a boat in Jamaica, a few drinks, and an idea that stuck

[5:48] – The real motivation: an industry of 100,000+ serious operators still served in a fragmented, affiliate-led way

[8:00] – Why there's no event dedicated to real estate technology specifically, until now

[10:18] – How most investors actually hear about tools, and why that system is broken

[13:05] – Referencing a well-known AI researcher's own admission that even experts feel overwhelmed by the pace of change

[16:26] – The three types of clients Steve talks to: AI skeptics, AI overbuilders, and the ones finding real balance

[18:35] – Jordan's own turning point: realizing a digital employee can't create leverage inside an analog business

[21:26] – Why AI hasn't eliminated jobs at Jordan's company, it's created a need to hire more people

[24:44] – A break to highlight smrtPhone, the show's sponsor, and its 5,000 free calling minutes offer

[25:43] – Meta confirmed for the event, and what their advertising and AI leadership will cover

[27:22] – Salesforce and Slack confirmed, and their pivot from CRM infrastructure to an agent-forward model

[29:28] – Collective Genius, the mastermind community all three hosts belong to, also attending

[30:14] – Twilio joining through the smrtPhone partnership to talk trusted calling and FCC changes

[31:37] – Why visibility for this industry with major brands is its own quiet win for the event

[36:42] – Steve's closing highlight: what a sales team should look like in 2026 versus 2024

[38:00] – Jordan's closing highlight: senior smrtPhone developers attending just to listen to customers

[39:36] – Stephanie's closing highlight: an environment where everything discussed is directly relevant

[42:17] – Final call to action and where to find ticket links


5 Key Takeaways

  1. No Pay-to-Play, Just Real Relationships — Every company attending is one the hosts' own clients already use and trust, not a sponsor who bought a table. The goal is real, hands-on conversations instead of scanning a QR code and walking past.
  2. Real Estate Investing Is a Massively Underserved Niche — Despite over 100,000 serious operators in the US, the industry has never had a dedicated technology event, and most investors hear about new tools through affiliate links and coaches rather than direct evaluation.
  3. AI Is Creating Jobs, Not Just Eliminating Them — Contrary to the fear many had at the start of the year, increased productivity from AI is creating new bottlenecks downstream, meaning businesses that adopt AI well often need to hire more people, not fewer.
  4. Isolated Tools Don't Create Leverage, Redesigned Businesses Do — Simply plugging in a new AI tool without rethinking how it interacts with the rest of your business creates new bottlenecks instead of real gains. The leverage comes from redesigning the business itself.
  5. Major Brands Are Finally Paying Attention to This Industry — Companies like Meta, Salesforce, and Twilio sending senior leadership to this event, rather than just sales reps, signals real recognition of real estate investing as a market worth building for directly.


Links & Resources


Thanks for tuning in to this one. If you've been on the fence about REI Tech Unlocked, this is the moment to grab your ticket before the room fills up. Head over to reitechunlocked.com for details and tickets, and thatrealestatetechguy.com for all the episodes and some great discounts on the tech we talk about. More high-signal conversations coming next.

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Jordan Samuel Fleming

Host