That Real Estate Tech Guy

This week, that real estate tech guy himself, Jordan Samuel Fleming, goes solo to tackle one of the biggest questions AI raises for business owners: not what can a person or an AI agent do, but who should do it. Using a hypothetical AI sales agent named Daniel, he breaks down why the old dividing lines between "human work" and "AI work" are starting to fall apart. Jordan introd...

This week I want to introduce the second part of the framework I've been building across these videos: bounded responsibility. Think about the best person you've ever managed, someone you trusted with real autonomy. That trust almost certainly came from clear boundaries, not the absence of them. They knew what they owned, what information they had access to, what decisions they could mak...

This week I want to challenge one of the biggest promises being made about AI right now: automation. It sounds great, take an existing process and make it faster with AI, but I think there's a question that gets skipped way too often. Should this process exist in the first place? When you automate a process without asking that, you're quietly assuming every step, every handoff, and every...

This week I want to go deeper into an idea I touched on before: your job descriptions might actually be hiding how your business really works. I use a detailed example, a salesperson named Jennifer, and follow her through an entire day to show that "salesperson" isn't really one job. It's a bundle of completely different kinds of work, administrative tasks, predictable executio...

This week I want to tackle a question I hear constantly from business owners, and I think it's actually the wrong question to be asking: "what can AI do in my business?" It feels reasonable given how fast AI capability is moving, but starting there makes AI the center of the conversation when it should be the work. Your business exists because of outcomes that need to be produced, n...

This week I want to dig into one idea that I think is going to cause a lot of businesses real problems if they don't get ahead of it: the assumption that dropping an AI agent into a part of your business automatically creates leverage. It sounds obvious on the surface, an AI that can work faster and handle more volume than a person should scale your output. But I don't think that's...

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...

This week I'm doing something a little different, a special solo bonus episode, just me, talking about something I'm genuinely fired up about: REI Tech Unlocked, happening September 19th through 21st in Dallas. This is the event I always wished existed in this industry but never did, so about four years ago, over drinks in Jamaica with Stephanie Betters from Left Main REI, we started dre...

Steve Trang is the founder of Objection Proof AI and host of Real Estate Disruptors, a sales trainer who has coached thousands of salespeople and hundreds of business owners since 2019 and now consults with nine figure companies on sales. He started in real estate as a realtor in 2007 and has spent the last several years turning what he listens for on a live sales call into AI that can score, role...

This episode originally aired in early 2023, and we're bringing it back because the fundamentals in it have not aged a day. The conversion principles, the testing discipline, and the friction thinking Trevor lays out are just as useful to real estate investors today as they were when this first ran. Trevor Mauch is the CEO of Carrot, the website and lead generation platform behind more than 7...

Jordan Samuel Fleming is the founder and chairman of smrtPhone, a real estate technology company he scaled from three co-founders to roughly $10 million in annual revenue and 60 employees over eight years. He stepped out of the CEO seat in March 2025 and spent the following year building the AI Labor Architecture Framework, now the foundation of his new book, The AI Workforce: How to Redesign and...

This week I'm joined by John Misarti, an investor who genuinely wears a lot of hats. Over the last decade he built "I Will Buy Your House For Cash" from a couple of New Jersey counties into a cash-buying operation that now fields off-market deals from California to Florida, launched an investor-focused syndication business targeting 20 to 100 unit apartments in the Southeast, and st...

This week I'm joined by my friend Joe Evangelisti, and his path into real estate runs backwards from almost everyone else I talk to. Most flippers start with the deal side and slowly pick up construction knowledge. Joe did it in reverse. He came up as the son of a general contractor, spent six years building all over the world with the US Navy Seabees, and walked into real estate in 2007 alre...

This week I'm joined by my good friend Adam Whitney, a real estate investor behind Blackjack and the CEO of Seven Figure Flipping, the largest house flipping mastermind in the country. Adam's story is one of the more remarkable ones I've come across. He grew up outside Detroit, lost both parents to addiction, and was staring down a home invasion charge at 18 before a Marine recruite...

This week I'm joined by Andrew Becker, founder of Billions CRM and Probate Engineers, who spent seven years working at the Pentagon in nuclear weapons systems before spending 11 years running a real estate team where he built the operational playbook that eventually became his own software company. He brings the same precision he learned in government work to every system, process, and lead s...

This week I'm joined by Brian Waters, a Los Angeles fire captain, certified flight instructor, and founder of the Rental Property Playbook who teaches hardworking W-2 earners how to build single family rental portfolios out of state. Brian lives in California but invests across Alabama, Georgia, Michigan, and Tennessee, all without quitting the job he genuinely loves. We get into why he chose...

This week I'm joined by James Heartquist from Property Leads, a pay-per-lead company built specifically for real estate investors who want to stop chasing cold lists and start fielding inbound sellers ready to move. James has worked with hundreds of investors across the country and has a front-row seat to what separates the operators doing deals from the ones who can't convert leads they...

This week I'm joined by Ari Paige, founder of Fund and Grow, a 19-year-old business credit consulting company that has helped over 35,000 businesses access more than $2.1 billion in funding through 0% introductory business credit cards. Ari originally got into this space as a real estate investor himself, which gives him a grounded, practical perspective on exactly where capital gaps show up....

This week I'm joined by Keith Gillespie, founder of REI 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...

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 teach...

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 week I'm sitting down with Andrew Schlag from TrueCo — and this one is a little different. We still talk real estate, we still talk business, but this episode goes somewhere most podcasts in this space are too afraid to go. Andrew opens with losing $3 million — not from a bad market, but from a moment of desperation and misplaced trust — and what that brutal season taught him about the l...

This week I'm joined by Michael Hoang, host of the Get Wealth Podcast and real estate investor out of Houston, Texas. Michael has done over 200 doors across single family and multifamily — but when the market shifted, he didn't grind harder on the same strategy. He pivoted into something I hadn't heard of before, and honestly, I couldn't stop calling it elegant the entire episo...

This week I'm sitting down live in Tampa with my good friend Rafael Cortez — firefighter turned carpenter turned transportation entrepreneur turned real estate investor turned coach turned SaaS founder. Yeah, Rafael has lived a few lives. And every one of them feeds directly into what he's built with CEO Pulse. Rafael brings an organizational psychology background and over a decade of ac...

This week I'm joined by Tyler Austin, CEO of Data Sift — the powerhouse platform born from the merger of Data Sift and Data Lake. Tyler and I go way back, and we finally got to sit down together in person at a mastermind in Tampa for this one. It's a great conversation. Tyler breaks down how his platform uses AI to predict over 50% of real estate investor transactions monthly, why less d...