That Real Estate Tech Guy

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

• smrtPhone (sponsor) — the only phone system built for real estate investors, connecting your calls, texts, and AI voice agents to a best-in-class REI CRM. Listeners get 5,000 free calling minutes. — https://www.smrtphone.io
• REI Tech Unlocked 2026 (September 19–21, Dallas, Texas; hosted by Left Main REI, Objection Proof AI, and smrtPhone; every attendee receives a free copy of Jordan's book) — https://reitechunlocked.com
• Left Main REI (Stephanie Betters) — https://www.leftmainrei.com
• Objection Proof AI (Steve Trang) — https://objectionproof.ai/
• That Real Estate Tech Guy (all episodes plus discounts on real estate tech platforms) — https://thatrealestatetechguy.com

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.

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 dreaming about getting the best real estate investment technology companies in one room so investors could actually get hands-on with all of it at once. That dream is now real, built together with my good friend Steve Trang from Objection Proof AI.

The whole point of this event is hands-on access, not another conference where you leave hyped up with no idea how to execute. You'll be able to sit down face to face with the technology companies that actually drive your leads, your calls, your CRM, and your funding, whether you're already a customer looking to get more out of the tools you have, or you've never used them and want someone to set up your account and walk you through it in person. Meta, Salesforce, and Twilio are all going to be in the room talking about where AI is taking Facebook ads, CRM, and trusted calling over the next 18 months, and that matters directly to how you run your business. If you want to cut through the noise around which tech actually moves the needle instead of just chasing shiny objects, I'll have a link with 50% off tickets, and I hope to see you in Dallas.

Episode Timeline & Highlights

[0:00] – Introducing REI Tech Unlocked, September 19th to 21st in Dallas

[0:23] – The origin story: a dream conversation with Stephanie Betters in Jamaica four years ago

[1:27] – Partnering with Steve Trang of Objection Proof AI to bring the event to life

[1:53] – The basics: where, when, and the 50% off ticket discount available

[2:33] – Why technology is the one absolute necessity for scaling a real estate business

[3:41] – Calling out "shiny object syndrome" and who this event is really built for

[4:16] – What attendees get: seeing where the technology is headed over the next 18 months

[4:58] – Meta and Salesforce in the room on AI in Facebook ads and where CRM is headed

[4:58] – Jordan's own smrtPhone partnership with Twilio on trusted calling in the age of AI

[5:23] – Sitting down 1-to-1 with the exact companies whose tools you already use

[6:01] – What it looks like if you're not yet a customer: live account setup and onboarding

[6:42] – Why face-to-face access to your entire tech stack almost never happens otherwise

[7:05] – Avoiding the typical event trap of leaving motivated but with no execution plan

[8:10] – A break to highlight smrtPhone, the show's sponsor, and its 5,000 free calling minutes offer

[9:06] – Why volume-focused AI lead gen isn't the same as performance

[9:26] – The overlooked opportunity: AI search optimization for real estate investors

[10:11] – The value of being in a room where builders and top performers share what's actually working

[10:36] – The exhibitor list: Left Main, Objection Proof AI, Twilio, Meta, Salesforce, and more

[11:11] – Why technology is what lets you scale without inflating your overhead

[11:54] – Closing invitation and where to find the ticket link

5 Key Takeaways

1. Hands-On Beats Theoretical — REI Tech Unlocked was built specifically so investors leave with new systems actually onboarded, not just inspired with no plan for execution, which Jordan says is the most common failure mode of industry events.
2. Face Time With Your Tech Stack Is Rare — Sitting down one-on-one for a full hour with the exact companies that drive your leads, your calls, your CRM, and your funding is an opportunity most investors never get, whether you're already a customer or brand new to the tool.
3. Volume Isn't the Same as Performance — Chasing AI for lead volume alone misses a bigger opportunity: AI search optimization, making sure your business shows up when people are actually asking AI for recommendations, which almost nobody is focused on yet.
4. Shiny Object Syndrome Is the Real Enemy — Serious investors trying to build a real business need to know where genuine leverage comes from, not just chase the next quick-win tool everyone's talking about this month.
5. The Best Insight Comes From the Room, Not the Internet — Understanding what's actually working right now requires being where builders and top-performing investors are talking directly, not just reading about trends secondhand.

Links & Resources

• smrtPhone (sponsor) — the only phone system built for real estate investors, connecting your calls, texts, and AI voice agents to a best-in-class REI CRM. Listeners get 5,000 free calling minutes. — https://www.smrtphone.io
• REI Tech Unlocked 2026 (September 19–21, Dallas, Texas; hosted by Left Main REI, Objection Proof AI, and smrtPhone; 50% off tickets with the link in the show notes) — https://reitechunlocked.com/registration?promo=smrtphone50&utm_source=smrtphone 
• Left Main REI (Stephanie Betters) — https://www.leftmainrei.com
• Objection Proof AI (Steve Trang) — https://objectionproof.ai/
• That Real Estate Tech Guy (all episodes plus discounts on real estate tech platforms) — https://thatrealestatetechguy.com

Thanks for tuning in to this special one. If you're serious about scaling with technology instead of just chasing the next shiny tool, get yourself in that room in Dallas. Head over to reitechunlocked.com for the details and your 50% off tickets, and thatrealestatetechguy.com for all the episodes and some great discounts on the tech we talk about. More high-signal conversations coming next.

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 play, and now sell.

This conversation covers what actually makes a salesperson close, why empathy is a transmission of information and not an emotional performance, and how AI call scoring, role play bots, and voice agents are replacing the work sales managers hate doing. If you run a real estate acquisitions team and you are trying to figure out where AI fits without gutting your sales floor, start here.

Timeline Summary

[2:31] – Steve introduces Objection Proof AI, built to review calls, run role plays, set appointments, and follow up

[4:16] – From 2007 realtor to training thousands of salespeople and consulting with nine figure companies

[6:40] – Chris Voss on empathy as the transmission of information, not an emotional outpouring

[8:16] – Jamil on why you should learn to sell from a robot instead of the naturally charming closer

[12:16] – Empathy beats sympathy, and why rapport is not what gets a contract signed

[15:03] – How Steve and Ian spent two hours documenting every single thing he listens for on a call review

[16:31] – The heart surgeon analogy for letting AI do everything before the high value work starts

[18:43] – Why cherry picking three good and three bad calls hides your team's real performance patterns

[23:20] – Five role play bots used for training and as a screening tool before an interview is ever booked

[26:17] – Three voice agents, web form speed to lead under two seconds, inbound coverage, and CRM follow up

[28:12] – Eric Brewer's 60,000 raised hands and the six figures sitting dead in almost every CRM

[33:37] – Why agents are not allowed to make offers yet and what real time underwriting has to solve first

[39:03] – Why lead manager roles get automated first and why you should keep your best one

[42:25] – Fast Five begins with the seven media hires in 2021 that nearly broke him financially

[43:54] – Move slowly, add one tool a month, and let the efficiency compound

[47:17] – Where to upload a call for free analysis and the two text keywords to try the bots

5 Key Takeaways

1. Empathy Is Information, Not Emotion — You do not have to feel what the seller feels. You have to articulate back how they got into the mess, what keeps them up at night, and what they want next. That is what builds trust, and it is fully trainable.
2. Score Every Call, Not Three Calls — Reviewing a handful of cherry picked calls gives you anecdotes. Scoring all of them surfaces the real outliers on both ends, so you know who to study and who to fix.
3. Make The Feedback Loop Public — Steve's team pushes every call review into a shared group chat and requires reps to respond to it. How a rep explains their own call tells you exactly where they are stuck.
4. The Money Is Already In Your CRM — Most investors chase new leads while five years of raised hands sit untouched. A follow up bot that tags a list and live transfers the interested ones turns dead data into appointments.
5. Roll Out One Tool A Month — The all or nothing approach to AI wrecks processes and morale. Pick one tool, get it running, then add the next. Small efficiency gains compound faster than a full rebuild.

Links & Resources

• That Real Estate Tech Guy — https://thatrealestatetechguy.com
• Objection Proof AI, free call and transcript analysis, confirm the exact URL before publishing
• Real Estate Disruptors, Steve's podcast, add URL before publishing
• smrtPhone, the phone system built for real estate investors, add the standard show link
• Try the role play bot, text ROLEPLAY to 33777
• Try the follow up bot, text CASH to 33777
• Never Split the Difference by Chris Voss, the empathy definition Steve references
• Left Main REI, mentioned via Stephanie Betters, add URL before publishing
• InvestorLift, mentioned as a compliant opt in data source, add URL before publishing

Enjoyed This Episode?

If the heart surgeon breakdown of call reviews made you rethink how your sales manager spends their week, send this to whoever is currently listening to calls by hand. Steve gave away the entire logic behind his scoring bot in this one, and none of it requires you to buy anything to start using it. Follow That Real Estate Tech Guy, leave a rating and review, and head to https://thatrealestatetechguy.com for every episode plus discounts on the platforms we cover.

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 7,000 of the top real estate investors and agents, whose clients pull in roughly 80,000 leads a month across the US, Canada, Australia, the UK, and South Africa. He got into real estate by buying a fourplex at 21 with none of his own money, then spent the next decade learning how to rank websites and turn traffic into deals.

In this conversation with Jordan Samuel Fleming, Trevor breaks down the actual science behind why some real estate investor websites convert and most do not, from the three form field rule to the five word button change that more than doubled conversion across test sites. If you are running a we buy houses site, paying for leads, or wondering why your traffic is not turning into contracts, this one gives you the specific levers to pull.

Timeline Summary

[0:52] – Jordan introduces Trevor Mauch and the platform behind thousands of investor websites

[1:09] – Carrot serves over 7,000 investors and agents and drives roughly 80,000 leads a month

[2:15] – Buying a fourplex at 21 with none of his own money and getting hooked on marketing instead

[3:13] – The failed software bets before Carrot and what they taught him about building tech

[4:09] – Why the next decade of websites would be about performance, not just being online

[6:47] – How a Squarespace site or a cheap Upwork clone quietly costs investors deals

[10:46] – Inside the quarterly testing process across 220 MSAs and roughly 1,000 websites

[11:50] – Carrot clients hold over 60% of top five rankings in the top 220 US markets

[12:25] – The mobile test that lifted conversion 25% just by moving the form higher

[17:50] – The non negotiable website principles including why three form fields beats seven

[19:13] – Changing five words on a button more than doubled conversion across test sites

[20:44] – Why friction is the real killer in marketing and where it hides in your follow up

[22:58] – Keith Sant's Calendly trick that closed deals from late night form submissions

[25:31] – The Investor Fuse acquisition and the hybrid thesis for investors and agents

[28:37] – Fast Five on the highest impact feature and the mistake most new users make

[30:17] – Why all offline marketing creates online demand and how ignoring it costs you

5 Key Takeaways

1. Pretty Websites Lose To Tested Ones — Squarespace and custom builds are made to look good and launch fast, not to convert. Trevor's team tested a wholesaler's popular, good looking site across 20 markets and it performed worse than Carrot's in most of them.
2. Three Form Fields Is The Ceiling — Seven fields will get you highly qualified leads and tank your conversion rate. Three is the tested sweet spot regardless of market or lead type, and your button should span the full width of the fields above it.
3. Five Words Doubled Conversion — Swapping generic button copy like Submit or Continue for benefit driven language like Get My Fair Cash Offer more than doubled conversion on test sites. The entire industry standard shifted because of that test.
4. Friction Is The Whole Game — Marketing is just removing friction between someone's pain and your solution. That includes your form, but also how fast a lead gets a human on the phone. Twenty four hours of delay is friction you chose to add.
5. Offline Marketing Creates Online Demand — Direct mail and cold calls send people straight to Google to look up your company name and reviews. If you do not rank well for your own brand, your offline spend leaks deals you never see.

Links & Resources

• Carrot — https://carrot.com
• smrtPhone — https://smrtphone.io
• That Real Estate Tech Guy — https://thatrealestatetechguy.com
• Investor Fuse — https://investorfuse.com
• Left Main REI (Stephanie Betters) — https://leftmainrei.com
• Calendly — https://calendly.com
• Google Sheets — https://sheets.google.com
• Also mentioned: The Carrot Cast podcast and Trevor's Thursday Truck Talks, Carrot Camp, Objection Proof AI with Steve Trang, and REI Tech Unlocked in Dallas

Enjoyed This Episode?

If you have ever looked at your website traffic and wondered why so few of those visitors turn into contracts, Trevor's three form field rule and the button copy test are worth acting on this week. Send this to the investor you know who just spent good money on a beautiful site that is not producing. And if the show helps you, follow, rate, and review so more investors can find it.

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 Scale Your Business with Artificial Intelligence.

In this solo episode, Jordan lays out why plugging AI tools into your existing processes misses the real leverage, and walks through the three-part framework he built to redesign a business around agentic workers. If you're a business owner wondering whether AI makes your company obsolete or whether your processes are even ready for AI employees, this episode reframes the question entirely.

Timeline Summary

[0:25] – Jordan opens a special solo episode about his new book on AI and business redesign

[1:36] – Why "redesign" is the most important word in The AI Workforce title

[2:14] – Scaling smrtPhone from three co-founders to 60 employees and $10 million in revenue

[3:36] – The distinct levels every business hits at 10, 20, 40, and 60 people

[5:10] – Stepping down as CEO in March 2025 to become chairman and what that freed up

[6:53] – How leaving day to day operations broadened his thinking beyond the C-suite

[7:15] – Early conversations with Stephanie Betters and the shift toward voice AI agents

[9:12] – The question nobody was asking: how do agents actually work inside a company

[10:08] – Treating AI agents as real employees, not just fast 24/7 capabilities

[15:26] – The assumption every business runs on that is no longer valid

[16:43] – Why CRMs and automation accelerate but never actually make decisions

[18:17] – Introducing the AI Labor Architecture Framework built over months of testing

[19:46] – Part one, work architecture: unbundling work, role, and execution from the human

[22:02] – Part two, bounded responsibility: why fuzzy processes propped up by Jim break AI

[24:12] – Part three, infrastructure: an agent making 10,000 calls creates chaos without flow

[31:25] – Why agentic AI is as drastic a shift as the internet itself

5 Key Takeaways

1. Stop Bundling Work Into People — We've always packaged work, role, and execution into a single human job. Work architecture separates those three things so you can see what actually needs to get done rather than who does it.
2. Automation Never Made Decisions — CRMs and automation tools run on if-this-then-that logic. Agentic workers analyze new situations in context and take action, which is why treating them like accelerants misses the entire point.
3. Fuzzy Processes Break AI — If your documented process quietly depends on Jim knowing when to deviate, that isn't a process. AI can't follow judgment calls, so bounded responsibility means defining context, limits, and escalation paths explicitly.
4. Leverage Dies At The Handoff — An agent that makes 10,000 calls a week creates chaos, not leverage, if a human has to hunt down the outputs and decide next steps. Infrastructure is about work moving seamlessly between people, AI, and systems.
5. Redesign Instead Of Downsizing — Redesigning processes around AI workers usually frees a team to handle ten times the volume rather than cutting headcount. The output is higher growth capacity, not a smaller payroll.

Links & Resources

• That Real Estate Tech Guy — https://thatrealestatetechguy.com 
• The Future Workforce AI (free book registration and framework system) — https://thefutureworkforce.ai 
• smrtPhone — https://smrtphone.io 
• REI Tech Unlocked, September 19 to 21, Dallas TX — use the coupon code in the episode description for 50% off through August 4, 2026 
• Left Main REI (Stephanie Betters) — https://leftmainrei.com 
• Objection Proof AI (Steve Trang) — https://objectionproof.ai

Enjoyed This Episode?

If the line about your process being propped up by Jim making judgment calls landed a little too close to home, you already know where your business isn't ready for AI workers yet. Send this to an operator who keeps buying AI tools and wondering why nothing compounds, because the fix is in the redesign, not the tool. Follow That Real Estate Tech Guy, and leave a rating and review so more business owners can find these conversations.

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 started his own podcast along the way. He is exactly the kind of scrappy, systems-minded operator I love talking to.

We dig into two things I was really curious about. First, how he made the leap from investing in one local market to executing deals at arm's length across the country, and the team-building lessons that made it work. Then we get into the tech, especially voice agents, where John went from total skeptic to a full convert after his AI agent "Jessica" locked up a contract 2,500 miles away on an after-hours call. If you have ever wondered how a lean operation can punch way above its weight, this one is for you.

Episode Timeline & Highlights

[0:00] – Jordan introduces John Misarti, an investor who wears a lot of hats

[2:11] – John's three buckets: cash home buying, syndication, and a podcast

[2:36] – How "I Will Buy Your House For Cash" acquires off-market deals across the Northeast

[5:36] – From hating corporate finance to a first flip and going all in in 2018

[7:37] – Why wholesaling is cheap to start but brutally competitive

[8:23] – Using an authoritative SEO push to pull leads across state lines

[9:37] – The real challenge: executing deals at arm's length from another state

[10:53] – Building boots-on-the-ground teams through local Facebook groups

[13:27] – Lessons from deals that went wrong, starting with cheaper is not better

[15:04] – How technology became the great leveler for a one-man operation

[16:20] – The old manual stack: List Source, skip tracing, Excel, dialers, and Podio

[17:44] – Meet Jessica, John's AI voice agent who books deals while he sleeps

[21:11] – Going from skeptical to sold on voice agents in five minutes

[26:39] – The California deal Jessica locked up 2,500 miles away, after hours

[29:18] – Why people do not mind talking to AI if it removes the friction

[32:32] – Where AI goes next: investor updates, webinars, and property management

5 Key Takeaways

1. SEO Can Expand Your Market for You — John's authority-focused SEO push started in a couple of New Jersey counties and naturally spilled across state lines as reviews and backlinks grew. He now receives deals from California to Florida without ever setting foot there.
2. Hire People Better Than You — Executing deals at arm's length comes down to building a local team you can trust. Find your realtor and GC through local Facebook groups, empower them, and manage from a weekly check-in.
3. Cheaper Contractors Are a Red Flag — When a GC is dramatically cheaper, dodges naming you on their insurance, or has no online reviews, treat it as a warning. Make the best decision you can and empower them with bonuses and referrals.
4. Always Answer the Phone — Motivated sellers move fast and rarely leave voicemails. An AI voice agent that catches every call, including overflow and after-hours, turns missed calls into contracts, as it did on a deal 2,500 miles away.
5. People Don't Mind AI If It Removes Friction — Callers do not care whether they are talking to a person or an agent, as long as they get where they need to go with zero friction. Trained well, and always honest about being AI, agents build trust rather than break it.

Links & Resources

• smrtPhone (sponsor) — the only phone system built for real estate investors, connecting your calls, texts, and AI voice agents to a best-in-class REI CRM. Listeners get 5,000 free calling minutes. — https://www.smrtphone.io
• That Real Estate Tech Guy (all episodes plus discounts on real estate tech platforms) — https://thatrealestatetechguy.com
• John Misarti's "I Will Buy Your House For Cash" (his off-market home buying business; confirm the exact URL) — https://iwillbuyyourhouseforcash.com
• Corner Store Millionaires Podcast (John's podcast interviewing business owners) — https://podcasts.apple.com/us/podcast/corner-store-millionaires-podcast/id6789637428
• Corner Store Millionaires Podcast (show website) — https://cornerstoremillionaires.podbean.com

Big thanks to John for coming on and being so open about how he built this thing, market by market and system by system. If you take one thing from this episode, let every call get answered, because that is where the deals are hiding. Head over to thatrealestatetechguy.com for all the episodes and some great discounts on the tech we talk about. More high-signal conversations coming next.

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 deal

5 Key Takeaways

1. Get 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.
2. 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.
3. 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.
4. 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.
5. 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 & Resources

• That 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 additive commercial coaching program 
• Reach Joe Evangelisti directly (call or text) — 856-244-1036

A really enjoyable one this week. Joe's story is a great reminder that the fundamentals, relationships, honoring your word, and getting the numbers right, outlast every market cycle, and his additive approach to commercial is one of the more genuinely useful coaching angles I've come across. If you're already doing single-family volume and wondering what the next level looks like, give this one a second listen. More high-signal conversations coming next.

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 teach

5 Key Takeaways

1. Fundamentals 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.
2. 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.
3. 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.
4. 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.
5. 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 & Resources

• SmrtPhone (episode sponsor) — the phone system built for real estate investors, with 5,000 free calling minutes for listeners: https://smrtphone.io
• Seven Figure Flipping — Adam's house flipping mastermind and the Teenage Tycoon kids program: https://sevenfigureflipping.com
• Blackjack — Adam's real estate investment company: https://blackjackre.com
• Adam Whitney on Instagram — @officialadamwhitney: https://www.instagram.com/officialadamwhitney
• The 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.com
• That Real Estate Tech Guy — all episodes and real estate tech discounts: https://thatrealestatetechguy.com

Enjoyed 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.

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 broken

5 Key Takeaways

1. Go 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.
2. 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.
3. 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.
4. 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.
5. 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 & Resources

• Billions 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 — @iamandrewhbecker

Enjoyed 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 rating and review goes a long way. More high-signal conversations coming next.

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 the most boring, tried and true strategy in real estate, how a property management team means he's never fixed a toilet in his life, and why keeping your W-2 is the smartest risk mitigation move you can make. If you're a first responder, a pilot, or any busy professional who wants passive income without blowing up your career, this conversation is for you.

Episode Timeline & Highlights

[3:09] – Brian introduces himself, an LA fire captain and founder of the Rental Property Playbook teaching W-2 earners to buy out of state

[3:50] – From a teenage pilot's license to a medevac career in Hawaii to a 2008 airline layoff that pushed him into firefighting

[6:30] – How cockpit habits like checklists, SOPs, and crew resource management became his real estate operating system

[7:01] – Why first responders make some of his most successful real estate students

[8:47] – Real estate as additive, not an escape from a career you actually love

[11:23] – The real reason to keep your W-2: lending leverage and protection from a single roof leak or foundation problem

[14:30] – The overtime trap that wrecks firefighter families and the lifestyle Brian built instead

[15:48] – How teaching buddies for free turned into a paid coaching community after a nudge from his wife

[17:13] – Why he picked the most boring, tried and true play over wholesaling, land, or syndications

[18:27] – The mentor advice that changed everything: get hyper specific at one thing and never change it

[20:23] – Tenants and toilets solved with out of state investing and a solid property management team

[23:31] – The four pillars of real estate returns and why Brian feels like he's always winning

[26:25] – The BRRRR method and how he buys four properties at a time using private and hard money

[33:05] – Why he caps his community at under 150 people and still answers his own DMs

[36:56] – How to find Brian and join the free Rental Property Playbook community

5 Key Takeaways

1. Keep The Job You Love — Real estate doesn't have to be an exit. Brian added single family rentals as a second income stream while staying a fire captain, which gives him lending leverage and a financial safety net.
2. Get Hyper Specific At One Thing — A mentor told him to master one strategy and never change it. He chose three bed, two bath single family homes because they're the most rented, sold, and refinanced asset in the country.
3. Out Of State Removes The Temptation — Investing far from home forces him to lean on systems and a property management team instead of driving over to fix a toilet himself. He's never done drywall in his life.
4. Budget For When, Not If — Stuff breaks in every asset class. He underwrites every deal with money set aside for vacancies and maintenance, so a surprise repair never turns into a crisis.
5. Small Community, Real Access — Brian caps his program under 150 people so students get his actual cell number and direct coaching, the opposite of being a dot on page 100 of a Zoom call.

Links & Resources

• Brian Waters / The Rental Property Playbook (Code 3 Invest) — https://code3invest.com/ (his actual coaching + community hub; "Rental Property Playbook" is his podcast/brand, but code3invest.com is where people sign up and reach him)
  Brian Waters on Instagram — https://www.instagram.com/mr.brian.waters/ \
  SmrtPhone — https://www.smrtphone.io/
  That Real Estate Tech Guy — https://thatrealestatetechguy.com/

If you've ever assumed out of state rentals are too risky or that you'd have to quit your job to build real wealth, Brian's playbook flips both ideas on their head. Share this one with a buddy in the firehouse, the cockpit, or any W-2 grind who's been waiting for permission to start, and take a second to follow, rate, and review the show so more people find it. More high-signal conversations coming next.