That Real Estate Tech Guy

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...

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 rent...

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 undere...

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 sti...

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...

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, a...

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 epi...

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 re...

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 disruptiv...

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...

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...

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 m...

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...