Jordan sits down with Zachary Beach of Smarter Real Estate to unpack the journey from bartender to full-time real estate investor and CEO of a thriving real estate coaching community. Zachary shares how he landed his first deal, the mindset shift that helped him go all-in on investing, and the communication skills that made cold calling a powerful lead generation tool.

The conversation dives into the real mechanics behind scaling a real estate business, including the importance of structured follow-up, building systems that move leads through a pipeline, and transitioning from doing everything yourself to building a team. Jordan and Zachary also explore how technology and AI are beginning to reshape lead generation and acquisitions in the real estate space.

If you want a behind-the-scenes look at what it takes to go from your first deal to a scalable real estate operation, this episode delivers practical insights on mindset, systems, and the fundamentals that actually drive growth.

About Zachary Beach

Zachary Beach is an experienced operator, real estate investor, and business leader who has helped scale multiple companies and investment portfolios through strong operational leadership, team development, and system-driven growth strategies. After serving as COO and later CEO, he played a key role in expanding a multi–seven-figure real estate coaching company, building high-ticket programs, scaling teams, and implementing operational systems that supported long-term, sustainable growth.

As a real estate investor, Zachary has built and scaled a portfolio using creative financing strategies designed to maximize returns while minimizing risk. He has personally completed hundreds of real estate transactions and has advised on hundreds more, helping investors develop the systems, mindset, and strategies needed to grow successful real estate businesses.

Important Links

Watch & Listen

• Free Book – Real Estate On Your Terms
• Get Zachary’s bestselling book and learn how to create three paydays on every deal: ThreePaydaysBook.com
• Smart Real Estate Coach – Creative financing training and mentorship
• smrtPhone – The only phone system built for real estate investors (5,000 free minutes)
• ThatRealEstateTechGuy.com – All episodes and exclusive tech discounts

I can tell you one thing: technology is the single most important aspect of every business that has successfully scaled.

It’s time for That Real Estate Tech Guy, your weekly chance to explore how technology can help your real estate business explode. Each week, you’ll hear from real estate investors who have been there and done that, and find out their favorite technology tips.

Listen in as Jordan speaks with tech companies and learns about new technologies and new ideas that will help you scale your business. And now, join your host, Jordan Samuel Fleming, CEO of smrtPhone, for this week’s episode.

Hello and welcome to this week’s episode of That Real Estate Tech Guy. I’m your host, Jordan Samuel Fleming, and today my guest is Zachary Beach from Smarter Real Estate.

This is actually kind of a repeat performance, because I had Chris Prefontaine on a couple episodes ago, who’s a business partner of Zachary’s, and his father-in-law, as I found out.

But I was really excited to have Zachary on to dive into some things we didn’t get into with Chris. Zachary’s got a really interesting backstory, from bartender to real estate investor to now the CEO of a coaching and community company. We got to dive into that journey, how he got into real estate, how he realized he could do it, and how he scaled it up.

We focused in on what it was like to go from that first deal to the realization that this can scale. That journey is going to resonate with a lot of real estate investors. Zachary clearly has a very clever approach to this. He’s very switched on, and very intentional about how he does things. You get a great sense of his journey, where the hard parts were, and the lessons he learned. I think it’s a great episode for that reason.

So let’s dive right in with my conversation with Zachary Beach.

Zachary, welcome to the podcast. Give us a little introduction to you and your background.

Sure, Jordan. Thank you so much for having me. I’m super excited to be here.

A little bit about me: I’m Zachary Beach with Smarter Real Estate. But 12 years ago, I was a bartender and a personal trainer. I didn’t really know what I wanted to do when I came out of college. One reason I went to college was because my teacher said I couldn’t, maybe you guys can relate to that.

When I graduated, I honestly didn’t know what I wanted to do, so I did what any good college student with a marketing degree does: I became a bartender.

I jumped into bartending, and when I started that, I told my now-wife, who was my girlfriend for a very long time, “Look, if we get into bartending, I want to do it for about four years. I’m giving myself that timeline.” I was about 21 when we did it.

It was getting around that three-year mark, and I started to say, “We’ve got to start looking at some additional options.” So I approached my girlfriend at the time, then fiancée, then wife’s father, Chris Prefontaine, who I know you’ve had on this podcast before, and I said, “Hey, I don’t know real estate well, but it’s going to be a heck of a lot better than what I’m doing right now.”

So I did what most people do. I started taking on a “side hustle.” I said, “Alright, let’s try this real estate thing.” I jumped in, started making phone calls, and from there I was able to accomplish my first real estate transaction within a relatively short period of time.

At that point, I was hooked. I said to Chris, I said to my wife, “Look, it’s time we make a transition. I think we burn the ships at this point.” So I went ahead and stopped bartending. I was personal training on the side as well, so I stopped doing that and jumped into real estate full-time about 11 and a half, 12 years ago.

And history has been made from there. I’ve been a full-time investor for almost 12 years now.

That’s fantastic. Let’s dive into that and unpack it a little, because there are a couple parts of that story that are really interesting and will probably resonate with people. I want to explore that jump, because it is a jump, and also the transition from side hustle to full hustle.

Let’s start with the bartending gig, because you said when you started that, you hopped on the phones. Most people are terrified about hopping on the phones. And I run a phone system, so I get that. But bartenders tend to have to be pretty sociable and speak to people if they’re good bartenders.

Do you feel like the jump into calling was eased because of the social element of personal training, where you’re coaching and motivating someone, and bartending?

That’s a great question. Interestingly enough, the bartender I became really close with ended up becoming a real estate agent. I went on the real estate investment side, which is funny that you bring that up.

When you look at a bartender, yes, there are skills you learn, especially if you’re going to be a good one. But there’s also a comfort level of being behind the pine, right? You’ve got a foot and a half between you and somebody else. I’ve never calculated the actual length of a bar, but I’m guessing around a foot and a half.

And there’s also some liquid courage involved too, right? Because if the bartender I was, I was entertaining bachelorette parties, and I lived and worked in a very destination, summer place. Newport, Rhode Island. Beautiful place. You’re there to entertain.

So yes, I think there were skills I developed when it came to entertaining people and thinking on my toes, because I had to have lots of very short conversations with people.

But to encourage people who weren’t bartenders, I also had to learn a heck of a lot of skills for being on the phone. I was just as afraid as everybody else. It wasn’t like I didn’t know what was at stake when I was on the phone with people.

So I had to learn a lot more skill sets and clear communication on the phone, because there are things you can make up for when you’re behind the bar, including giving somebody an extra shot to make sure they’re happy.

When it came to communicating on the phone, there were a lot of skills I had to learn. But yes, I agree that I had some practice being in front of people, which allowed me to make that transition maybe a little easier than most.

I’m going to date myself here, but as you were talking about that, it made me think about the movie Cocktail starring Tom Cruise back in the day. That probably dates me a little because that’s got to be a 30-year-old movie at this point.

Oh, at least. Yeah, I buy it. People always bring that up to me, especially the older crowd. They’re like, “See, you’re kind of like Cocktail.” And I’m like, “Yeah, but much better. Just imagine, I was better. They just didn’t have a movie about me.”

That’s funny, and it does date me a little.

Okay, let’s go into the skills, because you’re absolutely right. The transition from what you were doing into hopping on the phone… most people get nervous about making phone calls. And your point is interesting: in person you have visual cues, body language, facial expressions. That’s a huge part of communication.

You remove that the moment you hop on the phone. So how did you go about getting comfortable? Did you do any specific training? Walk me through that transition.

I love to bring this up because I’ve actually never been asked these questions in this order.

I honestly believe bartending helped me more with translating to a meetup or in-person networking group, because that’s more like bartending, where you’re constantly communicating with people on a short schedule, trying to get a feel for who they are and what’s happening in their lives, and then translate that to a longer-term relationship.

The phone’s a different animal, because the only way you can really tell what’s going on in someone’s life is if you leave a voicemail, they call you back, and you listen to their voicemail when they call you back. Then you’re like, “Okay, I’ve got a good understanding of tonality and attitude.” But we don’t always get that ability, and it can shorten or lengthen the time it takes to get to a deal because you’re playing phone tag and trying to understand tonality.

So for me, the phone was the 10,000-hours skill. It was repetition after repetition after repetition, and being able to manage the key rebuttals you have to put together.

When I look at a phone call, there are really three segments of the call, at least in our space.

First is the introduction. We have to be very particular in the introduction because we need to stop that person in their tracks a bit, make sure they know who we are, why we’re calling, and get permission.

We like: intro, clarification, then permission.

We introduce who we are because we never want someone later to say, “Wait, who are you again, and why are you calling?” We need to tell them exactly who we are.

Then we need clarification that we’re talking to the right person about their property, because how often have we gotten into a call 10–15 minutes later and we’re talking to the grandson of the decision-maker? Ask me how I know.

Then we need permission, which is probably the most important thing. We need permission to ask specific questions about them and their property, because especially when you’re doing creative financing deals, we ask some personal questions to someone we might not know that well. We need to build rapport and trust in a very short period of time. That’s where the skill set of making phone calls really comes into play.

You start to get deals more quickly because you can authentically build trust in a short period of time and get the information needed, so you can make a decision and you’re not spending tens of thousands of hours with people who aren’t going to do a deal. That’s a key component as you build a business.

Once we get permission, we have a key set of questions we need to ask to determine motivation. Motivation could be positive or negative. Some people want the best price, that’s not negative, they just want something better than what the market is giving.

Then you’ve got negative motivation like behind on payments, debt relief, financial bind. We need to identify that.

Once we’ve identified motivation, we jump into the financials of the property. That’s key for our investment strategies because we understand which strategy is going to come into play based on the current financials.

Then from there we educate people. We say we’re just as much in the education business as we are the investment business, because we need to educate people on new strategies and concepts so we can move them closer toward a deal.

I don’t know if I hit every component you were looking for, but if I missed anything, let me know.

Now, I’m sorry to interrupt this amazing conversation, but I wanted to make sure you knew that smrtPhone, the only phone system built for real estate investors, connects to the best-in-class real estate investor CRMs. And because it’s my show and I’m the co-founder and chairman of smrtPhone, I’ve got some great deals for you.

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Back to the show.

You know what makes me smile is everything you just talked about dovetails nicely into a lot of the work I’ve been doing recently inside smrtPhone. We’re releasing an entire recruitment center of AI voice agents, and it’s an immediately polarizing topic. Some people think that’s amazing, and some people think it’s the worst thing that’s ever happened and it’ll never do the job properly.

But the training we’ve been putting these agents through mirrors the training you’re describing, and the outcomes from these agents are powerful and aligned with what we want from humans. They just function 24 hours a day without needing to be.

It’s fascinating when you start to break down the structure of a conversation. I love the permission element, especially the ability to draw enough of a relationship where people open up to their real motivations. A lot of people guard motivation, and you still need to build trust and permission to get them to bring you the real motivation.

When you start to break down what conversations really are, whether you’re teaching a person or teaching an AI agent, those principles remain true.

I don’t know if you’ve had any experience on the AI side, but you’ve certainly trained people with the way you’re speaking about it.

Oh, for sure. We’ve trained hundreds of thousands of people. That is the first skill within our genius model that you really need to nail down: mindset, skill set, systems, and communication with sellers.

Communication with sellers is the beginning, because every business needs lead generation and needs it consistently if you want a predictable business long term.

And I’ll tell you, I’m the type of person that says, “Yeah, let’s get AI to do those phone calls.” If we can train virtual assistants all across the country to gather that information without the background knowledge tied to AI, then we can get that done too.

I would love that, because then real estate investors can uplevel and focus on money-producing activities. That means they’re more likely to leave their W-2 job, build side income, or take vacations because they’re spending five to ten hours a week on money-producing activities.

The only pushback is that a lot of investors today learn that skill set at a very low barrier by doing lots of phone calls to uplevel their skills. So there would be foundational training that needs to get nailed down.

But I love what you’re saying about AI generating long-term success through automation. Keep pushing that forward.

Automated… and it’s funny, I was in a meeting the other day with a guy who built a CRM system, one of our partners, and he’s building a set of AI agents with us right now for his community because he has a coaching platform.

I was setting him up with a demo of our acquisitions agent, because what people don’t understand is just like people, agents need to be trained for roles. Specific training means they produce.

He said, “I’m going to call right now.” Live demos are always a nightmare, but he was having a conversation with our agent about a property, and the agent had a full conversation about the probate process and asked intelligent questions naturally.

That’s where the technology is now. We can follow up on that after the show if you’re interested.

But to dive back into your journey, I know Chris has a very direct mannerism, very Massachusetts, and I really enjoyed that conversation. But I want to dive into your experience getting deals going.

You got your first deal relatively quickly, you were hitting the phones. What was your personal journey of moving into doing it full time and realizing this is something you can do as an investor?

Yeah, and this ties back into what I was saying earlier. It was a mindset shift that hit me after I got my first deal.

I think that’s what hits most investors trying to make this jump. I was lucky enough to do it at 24 versus people doing it in their 40s, 50s, and 60s because they spent longer pursuing a different career.

The moment I was confident enough and clear enough that I could help people was the moment I started asking hard questions. Yes, we need rapport on the phone, but we also need very specific questions to determine if it’s a good fit.

The faster you can make that decision, the quicker you can get off the phone or put them into your follow-up system and go to the next person.

After I got that first deal, I realized, “Oh, I can truly help people. I can actually do this.” One deal doesn’t make me a real estate investor, but I knew I could be successful at it.

Outside of sports, I didn’t find that in school or college. I found it maybe a little in bartending, because I could entertain people and move up, but I realized this could change my stars.

I grew up with a single mother and no big financial backing. She was a cashier at Lowe’s. I wanted to change the trajectory of my life. So I decided I could go all in.

I wasn’t all in until I saw a check, and the check wasn’t huge either.

That first deal was a little complex. It was a subject-to deal, which basically means you buy the property and the title transfers to your company, but you leave the current debt the seller has in place, and you make the payment on their behalf.

For most people it feels complex, but once I nailed it down, I thought, “If this is one of the more challenging deals, then seller financing and lease options are going to be a drop in the bucket.”

Don’t get me wrong, I had lots of learning lessons moving forward, but I knew I could do this. And that’s where my mindset changed. That’s when I started to go all in. I went from being paid for hours to being paid on results.

I tell this to our community members: you used to get paid for hours, now you get paid on results. So I had to switch my mindset. How do I do this monthly? Then a couple times a month?

That’s where scaling started to come into place. Chris was doing a lot of the closing, then I started taking over lead generation, then the seller side too. Then we moved my brother-in-law into the buyer side.

That’s when the team evolved, and that’s when we started to scale. At that point I started to see a clear vision, we doubled down, and we started doing four to ten deals a month because we looked at this as a viable scalable business, not just a lifestyle business.

Absolutely. Now you mentioned follow-up, and that’s where most investors fail. Everyone wants the shiny new thing, nobody wants the grind of follow-up, but follow-up is where you make all the money.

As you started to build, what was involved in scaling for you? What were the key things that helped you scale, whether it’s follow-up, consistency, structure, or something else?

Awesome question. No particular order.

First and foremost, the ability to duplicate and transition from one person who has all the knowledge to now value being added from others. These might sound novice, but they apply from a $1,000 company to a $1 billion company.

We needed to pull all the information from Chris’s brain and translate it into my brain, especially on lead generation and the seller side, because that’s where I felt natural and I knew I could produce.

Then we needed to do the same on the buyer side for Nick Prefontaine, my brother-in-law, so we were adding value as a team, not just as individuals doing tasks.

Then I brought a new set of eyes, and my brain works in systems. We needed to develop systems because we went from paper and pen to a system.

We created what’s known as our seven steps to a “taken.” A taken for us is a property under agreement. We said, “All we need to do is move this person from step to step,” which creates redundancy and an easier way to follow up.

At first we did it with a one-through-31 folder system. Every day I’d look at the date, pull out the folder, and that was my follow-up system. Someone would say, “Follow up in three days,” and I’d move the paper.

It worked for a little bit, maybe up to about a deal a month, but things get missed. That’s why a lot of people struggle with follow-up: they don’t have a system to remind them.

The fortune is in the follow-up. And it’s true. The hardest step is acquiring the new lead. It’s not the follow-up, but we forget and chase the next lead instead of the next deal.

That’s a mindset transition. You want to spend the most time closest to the deal, which is the follow-up.

Then we needed technology so it wasn’t just in my folder. We started using Podio back in the day, then InvestorFuse, then FreedomSoft, and then we created a strategic partnership with Daymond Remy and REI BlackBook.

We built out systems not only for us, but for our community inside REI BlackBook. They have everything from phones to websites.

That’s where it went from an idea, to paper, to technology, so we could move the business forward and translate more value to more people. Then we brought on additional VAs and other people to continue pushing lead generation so we could scale.

Absolutely. If only everybody actually believed the fortune is in the follow-up. Business fundamentals are fundamental for a reason. There is no shortcut.

It must frustrate you as someone who trains people when you see people skipping that fundamental truth.

It really is a transition in mindset. I used to show up at a bar and I knew I’d get paid based on the night. Now I need to deliver results.

Over my investment career, I’ve always looked for how to fine-tune so my skill set is placed where it produces the most results. Everything else eventually should be automated or delegated.

You can’t take 10 or 12 years of experience and dump it on a new hire. You have to train the new hire on fundamentals and elevate them over time.

It’s like the doctor’s office analogy: you only see the doctor for 15 minutes. Before that you’re greeted by reception, then a nurse, then someone else, then the doctor, then handed back off.

In your business, you might have a VA bring the lead in, then a seller specialist works with sellers and brings the lead to a point, and then you structure and close the deal. That’s the fun part of being an investor.

Eventually you get closer and closer to the money-producing activity. That’s where the mindset continues to shift. You learn to delegate and automate as much as possible so you can grow and reach the deal volume you want.

I think that’s fantastic, and a great message to end on.

Before we close out, Zachary, I want to give you a chance to let people know how they can get in touch with you and learn more about what you’ve built with Chris and your team.

I appreciate that, Jordan. If you’re listening to this, I want to give you our Amazon bestselling book, because we just barely scratched the surface.

If you want to learn how to buy real estate without cash, credit, or banks, and tap into our “three paydays” system where we create three income streams on every deal, I want to give you a free ebook. You don’t have to go on Amazon and buy it. I want to ship it to you for free.

All you have to do is go to threepaydaysbook.com. You can grab it, it’s called Real Estate On Your Terms. I co-authored it with Chris Prefontaine and Nick Prefontaine. It dives into our morals and strategies so you can bolt it onto your current business or use it to retire from your W-2 job.

Fantastic. And you know what, I’ve been talking to Chris about maybe coming on and doing one of the masterclasses inside our community. What I’ll do is make sure that link to the book is embedded in a way that’s much more visible to the community, because it’s a great offer.

Zachary, it’s been an absolute pleasure to meet you and hear your story. Thank you for coming on, thank you for giving such great value to the audience, and I’m looking forward to catching up with you again soon.

Thanks for listening to another amazing episode of That Real Estate Tech Guy. Head over to thatrealestatetechguy.com to check out all episodes and get special discounts on tons of awesome real estate technology platforms.