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That Real Estate Tech Guy

That Real Estate Tech Guy

By: 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.

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Episodes
  • The Construction Guy Who Learned Real Estate Backwards ft. Joe Evangelisti

    The Construction Guy Who Learned Real Estate Backwards ft. Joe Evangelisti
    Jul 9 2026
    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 already knowing how to build anything, but knowing almost nothing about contracts, mortgages, tenants, or sales. He had to learn the business from a standing start, and he did it right as the market was falling apart underneath him.We get into the whole arc: how he nearly lost his entire life savings on his first two flips, how one predatory-looking private loan turned into an $8 million relationship at 9%, and why performance, not pitch decks, is what actually unlocks other people's money. Then we shift to his Legacy Builder Real Estate Academy, which isn't a beginner program at all. It's built for investors already doing wholesale, fix and flip, or development who want to bolt commercial real estate onto what they've already got. Medical office, small-bay industrial, triple-net value-add, the stuff with better margins, fewer sharks, and real tax advantages. It's a different, more grown-up take on coaching, and Joe makes a strong case for it.Episode Timeline & Highlights[0:00] – Jordan sets up the episode and why Joe's construction-first path into real estate is unusual[2:12] – Joe's background: contractor's son, six years in the Navy Seabees, into flipping in 2007[3:12] – Why real estate attracts so many military veterans, and the discipline that carries over[4:47] – The "pen, notepad, and cell phone" mentor lesson and why tech amplifies whatever you already are[5:59] – Using tools like Gemini to underwrite deals, entitlements, zoning, and wetlands on commercial[8:22] – The gap Joe had to close: confident in construction, "real estate stupid" on contracts and banking[9:16] – His first two flips underwater as the market slid 12 months before the 2008 crash[10:20] – Course-correcting into landlording and long-term financing to save his life savings[12:20] – Meeting Dave: "If you want money, ask for advice. If you want advice, ask for money."[13:31] – Tearing up a $5,000 refund check and how honoring the deal earned $8M at 9%[15:26] – Why performance gets money and first-timers pay the highest cost for capital[17:18] – Moving with intention and building momentum instead of sprinting at 100 mph[18:54] – A word from SmrtPhone, the phone system built for real estate investors[19:19] – Why relationships beat everything in a tighter, more competitive 2026 market[20:38] – Bolting commercial onto an existing fix-and-flip business without blowing it up[22:16] – The pitfalls that sink new flippers: the numbers, over-improving, and investor-grade subs[24:38] – Managing construction risk when you're not the construction expert[26:46] – The organic origin of the coaching business, from short-sale volume to two-day events[29:45] – How the program evolved into an additive, higher-level commercial consultancy[32:21] – Why "add a stream" beats "replace what works" in a saturated coaching market[33:45] – How to reach Joe directly and get help underwriting a commercial deal5 Key TakeawaysGet Resourceful Before You Get Tools — Technology amplifies whatever you already are, so if you can't be effective without it, it'll just magnify your weaknesses. Master the fundamentals first, then bolt tech on to a business that already works.Performance Is What Unlocks Capital — Nobody hands money to an unproven first-timer at a good rate. Do your first two or three deals at whatever cost to build a track record, and your cost of capital drops fast after that.Honor the Deal and Relationships Compound — Joe tore up a refund check because a deal is a deal, and that integrity turned one lender into an $8 million, 9% relationship. How you show up on deal one determines what deal fifty looks like.The Numbers Are Where New Flippers Die — In a tight market you can't lean on appreciation to bail out a bad buy. Get the numbers right, don't over-improve, and build relationships with investor-grade contractors and suppliers who price for volume.Bolt On Commercial, Don't Blow Up What Works — The same skills that run a single-family business apply to medical office and small-bay industrial, where margins are fatter and competition thinner. The seller offloading a house may also be selling a dental practice, so one extra question can open a whole new deal flow.Links & ResourcesThat Real Estate Tech Guy (all episodes and tech discounts) — https://thatrealestatetechguy.com SmrtPhone (sponsor) — the phone system built for real estate investors; connects to best-in-class REI CRMs, with 5,000 free calling minutes via the show link — https://smrtphone.io Legacy Builder Real Estate Academy — Joe Evangelisti's ...
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    36 mins
  • The Four Numbers That Run an Entire Real Estate Business ft. Adam Whitney

    The Four Numbers That Run an Entire Real Estate Business ft. Adam Whitney
    Jul 2 2026
    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 recruiter and a judge handed him a second chance that changed everything.From there Adam built a 20-year Marine Corps career, discovered real estate through the FIRE movement, and scaled to 142 deals a year before he ever retired from active duty. In this one we get into why the boring fundamentals beat the sexy marketing bits every time, how he went from Seven Figure Flipping member to owner and CEO, and the Teenage Tycoon program they built to give kids real financial literacy in a world where the old school-to-job path is falling apart.Episode Timeline & Highlights[2:57] – Adam introduces Blackjack, his "a deal a day" firm, and why he treats real estate as a full business[4:34] – The two Seven Figure Flipping communities and the values of service, legacy, and impact[6:19] – Why so many Marines thrive in business: the innate ability to endure adversity[7:26] – Adam's childhood outside Detroit, losing both parents, and getting into trouble at 18[8:38] – The Marine recruiter and the judge who gave him a second chance at his arraignment[10:14] – From a 1.954 GPA to commissioned intelligence officer and a 20-year career[10:45] – Discovering FIRE and using real estate as a faster wealth-building vehicle[11:07] – Scaling to 142 deals a year before ever retiring from the military[14:45] – Joining Seven Figure Flipping as a member and learning under mentor Bill Allen[18:15] – Why building people, not chasing money, is what makes business worth it[22:24] – The journey from member to equity owner to CEO of Seven Figure Flipping[26:14] – The boring, repeatable "conveyor belt" that actually runs a flipping business[29:03] – How Andy McFarland flips 100+ houses a year on one simple system[32:00] – Four KPIs, green vs red, and why fundamentals beat shiny-object chasing[34:16] – Launching Teenage Tycoon to teach kids financial literacy the schools skip[40:44] – The Asset Quest game and rehearsing money decisions like military drills[46:23] – The kids' book club where authors like Sean Covey show up to teach5 Key TakeawaysFundamentals Beat Shiny Objects — Scale doesn't come from the newest Facebook ad strategy, it comes from executing boring, repeatable systems ruthlessly. The grass is only greener where you water it.Build Two Tracks Before You Jump — Adam ran his real estate business on the side while still an active Marine, so when one train stopped the other already had momentum. The transition was seamless because he prepared for it.Watch Four Numbers, Not Fifty — A clear KPI dashboard lets you glance at your business each week and know instantly where to dig in. If the fundamentals are green, you're fine; if one turns red, you zero in on it.Lead by Serving Your People — The more successful you make the people around you, the more your own success magnifies. Teams that know their leader has their back will do almost anything for the mission.Give Kids Financial Literacy Early — A 13-year-old who understands leverage, interest, and effective tax rates has a runway most adults never got. Exposing kids to what's possible beyond the school-to-job path is a real legacy.Links & ResourcesSmrtPhone (episode sponsor) — the phone system built for real estate investors, with 5,000 free calling minutes for listeners: https://smrtphone.ioSeven Figure Flipping — Adam's house flipping mastermind and the Teenage Tycoon kids program: https://sevenfigureflipping.comBlackjack — Adam's real estate investment company: https://blackjackre.comAdam Whitney on Instagram — @officialadamwhitney: https://www.instagram.com/officialadamwhitneyThe 7 Habits of Highly Effective Teens by Sean Covey: https://www.franklincovey.com/the-7-habits/for-teens/Rich Dad Poor Dad by Robert Kiyosaki and Sharon Lechter: https://www.richdad.comThat Real Estate Tech Guy — all episodes and real estate tech discounts: https://thatrealestatetechguy.comEnjoyed this one?If Adam's story moved you, do yourself a favor and sit with that idea about running the boring play at scale, because that's where the real money hides. Share this episode with someone who's chasing the shiny stuff instead of the fundamentals, and if you've got kids, take a hard look at what Seven Figure Flipping is building with Teenage Tycoon. More high-signal conversations coming next.
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    50 mins
  • Why Probate Leads Are the Most Underrated Lead Source in Real Estate ft. Andrew Becker

    Why Probate Leads Are the Most Underrated Lead Source in Real Estate ft. Andrew Becker
    Jun 25 2026
    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 source he touches.In this episode, Andrew breaks down how he used 80/20 analysis to identify probate as one of his highest-performing lead sources, how he turned that discovery into a coaching program called Probate Engineers, and how Billions CRM gives real estate operators a simplified Salesforce-powered system that actually drives accountability. If you're tired of chasing every shiny lead source and want a repeatable, consultative approach that builds real relationships, this one is for you.Episode Timeline & Highlights[0:52] – Jordan introduces Andrew Becker, founder of Billions CRM and Probate Engineers[3:21] – Andrew's background: nuclear weapons work at the Pentagon, seven years in systems-driven government roles[4:04] – How 11 years running a real estate team led Andrew to build Billions CRM[6:47] – How data and the 80/20 principle revealed probate as a top-performing lead source[8:21] – Getting probate leads directly from the courthouse rather than relying on aggregators[9:02] – Why personal representatives are a uniquely motivated and underserved audience[12:29] – Building a "power probate Rolodex" of attorneys, specialists, and experts to add real value fast[15:35] – Why inserting yourself into the probate process drives an 80-90% close rate vs. a 50/50 shot[19:35] – Launching Probate Engineers in late 2024, running beta cohorts, and improving the program with each group[22:33] – How feedback from beta cohorts led to building Captain, a tool that automates daily probate record extraction and mailing by county[25:06] – Live AI voice agent demo where the agent picked up on the word "probate" in real time and asked the right follow-up questions[27:39] – How Billions CRM was born out of frustration with piecing together 8-9 disconnected tools[29:12] – How Billions enforces one workflow path to eliminate confusion and keep data clean for 135 real-time reports[37:59] – Why a CRM integrated with a phone system like SmrtPhone creates accountability that cell phones never can[43:56] – Using automated nightly KPI reports to catch performance drops the same week they happen[44:44] – Why four KPIs are all you need to know if your business is healthy or broken5 Key TakeawaysGo a Mile Deep, Not Wide — Andrew's team stopped chasing every lead source and went all-in on the 20% producing 80% of their revenue, with probate being a standout performer. Narrowing focus created a machine that ran predictably instead of chaotically.Consultative Beats Transactional Every Time — Instead of calling probate leads and saying "I'll buy your house," Andrew's approach is to ask where they are in the process and connect them with attorneys, advisors, and resources at no cost. That kind of help builds trust no competitor can replicate by just sending an offer.Build the Rolodex Before You Need It — You don't have to become a probate legal expert. What matters is assembling a network of specialists, such as probate attorneys who handle it 90% of the time, so you can refer prospects immediately and become their go-to resource throughout the process.A CRM Should Guide Behavior, Not Just Store Data — Billions was designed with one way to do everything. No shortcuts, no alternate paths. That structure keeps reps on track, generates clean data across 135 real-time dashboards, and gives owners the visibility they need without requiring hours of manual review.Automate the Boring, Track What Matters — Whether it's daily probate record extraction through Captain or nightly KPI reports from Billions, the goal is the same: remove the manual work so your team stays focused on conversations, and so you catch problems in days instead of discovering them at the end of the quarter.Links & ResourcesBillions CRM — joinbillions.com Probate Engineers — probateengineers.com Captain AI (automated probate record tool) — joincaptainai.com SmrtPhone (real estate phone system) — smrtphone.io (5,000 free calling minutes available via the link in the episode) REI Tech Unlocked Conference (September 19-21, 2026 in Dallas, TX) — reitechunlocked.com Follow Andrew Becker on Instagram and Facebook — @iamandrewhbeckerEnjoyed This Episode?If Andrew's approach to probate leads has you rethinking where your next deal is coming from, share this episode with a teammate or fellow investor who's still chasing every shiny lead source. The consultative model he laid out is a genuine differentiator in any market. Follow That Real Estate Tech Guy so you don't miss what's coming next, and if you found value here, a quick ...
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    47 mins
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