He Quit His Job With 3 Airbnbs... | Michael Elefante | DSH #1965

Summary

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Podcast Summary: Digital Social Hour

Episode: "He Quit His Job With 3 Airbnbs..." | Michael Elefante | DSH #1965

Host: Sean Kelly
Guest: Michael Elefante
Date: May 15, 2026

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Episode Overview

This episode features an in-depth conversation between Sean Kelly and Michael Elefante, a short-term rental entrepreneur who transitioned from a W2 sales career to financial freedom via Airbnb and property management. The discussion provides practical strategies on scaling a real estate business, optimizing for tax savings, leveraging AI in real estate, and designing memorable guest experiences. Michael shares his journey from building up properties to quitting his job, plus personal stories and lessons for listeners who want to break into or scale in real estate investing.

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Key Discussion Points and Insights

1. Michael's Background & Business Update

• Transition & Scaling: Michael explains how he moved from a sales job to owning and managing a large portfolio of short-term rental properties.
  • "Financially free in 12 months of our first investment…just three Airbnbs." (10:08)
• Current Business Scope:
  • Owns 14 properties (~$30M value), manages 650+ with his management company, and on track for $80-100M in annual bookings. (02:20)
  • Focuses on premium properties with unique amenities—turf golf courses, wiffle ball fields, etc.—to attract high-value clients such as micro-weddings and corporate retreats. (01:44)

2. Why Short-Term Rentals Succeed (and How the Market Has Shifted)

• Experience over Pricing:
  • “If we’re able to curate an amazing experience, that's what people will pay for.” (01:22)
• Market Dynamics:
  • The short-term rental space is increasingly competitive, with mid-tier properties facing pricing pressure and narrowing margins.
  • “That's the worst place to be in any business…a race to the bottom.” (03:18)
• Advantages of Premium Approach:
  • Fewer properties, higher class = better guests, fewer headaches, and bigger tax benefits. (03:24)

3. Location Strategy

• Vacation Markets near Growing Metros:
  • Invests primarily in vacation markets near fast-growing cities (e.g., Southeast US, near Atlanta, NC, SC, TN).
  • “If you can set up a great property there, well, that creates sustained demand over time,” as population growth fuels ongoing interest. (03:40)

4. Financing and Maximizing Returns

• Conventional and DSCR Loans:
  • Mainly uses traditional financing (10–20% down), but stress is on creative strategies for returns, not just acquisition method. (04:17)
• Tax Optimization (“The Money Glitch”):
  • Short-term rentals (STRs) allow normal W2 earners to claim significant depreciation losses—offsetting active income if structured correctly.
  • Requirements include an average stay of 7 days or less and “material participation” (100+ hours/year).
  • “I had five set up last year. $1.7 million in depreciation the first year. Saved me $700,000 in tax.” (05:56)
  • Memorable Quote: “Taxes are the single thing that kill most Americans’ ability to accumulate wealth in their lifetime.” (05:33)
  • Save taxes, reinvest, and compound growth. (05:36)
• Refinancing/Borrowing Against Equity:
  • Pull equity tax-free by refinancing; use funds to further invest and grow, mirroring strategies of ultra-wealthy. (07:39)
  • “They can take their earned income… and invest it in other things that give them tax advantages. Then they fund their lifestyle by borrowing against their assets without selling them...” (07:39)

5. AI in Real Estate and Business

• Current & Future Use Cases:
  • Lead generation: Automate evaluating and identifying deals using market data and listing platforms, saving analysts hours per week. (13:38)
  • Operations: AI-driven guest communication, maintenance flagging, and even assessing guest satisfaction for prioritization. (14:31)
  • Photo editing, description writing, and more done by AI.
  • “AI is getting better and better for the guest messaging.” (14:34)
• Sean’s AI Use:
  • Uses multiple AI agents to source guests, sponsors, research, and outreach, fully automating major parts of podcast production. (15:23)
  • “Would have taken a VA that barely speaks English to do it. Probably would have cost more, to be honest.” (16:07)

6. The Power of Real Estate as an Equalizer

• Accessible Asset Class:
  • Unlike VC and private deals, real estate allows almost anyone to “level the playing field” with the same tax, leverage, and appreciation benefits. (25:43)
• Guest Management/Talent:
  • BNB Turnkey: White-glove service for high net worth individuals, including professional athletes, to fully manage deals and operations. (26:56)

7. Personal Journey and Lifestyle

• Fast Financial Freedom:
  • Michael and wife quit jobs within 16 months by scaling up cash flow to $30K/month. (10:19)
  • Lived and traveled for a year in a van, managing properties an hour a week remotely. (19:59, 20:18)
  • Memorable Quote: “Most of the travel was spent on the western half of the US…Hiked over 400 miles, visited over 20 national parks.” (20:16)
• Former Careers:
  • Michael: Sales (up to $200K/year, started at $35K). (10:41)
  • Wife: Autopsy technician. Shares dark humor about her work and how she catalogued cases. (18:33)

8. Overcoming Challenges and Advice for New Investors

• Common Mistakes:
  • Not understanding how to find and evaluate deals (“That’s really it.” 22:45)
  • Skimping on design/amenities instead of maximizing experience and value. (“You should have just bought a two-bedroom place, made it a badass top 1%…” 23:16)
• Learning & Success:
  • Taught over 3,000 students to invest in STR; over $1B acquired collectively. (22:02)
  • “I think people get very comfortable in their jobs…once I hit a glass ceiling, I was out and networking, trying to find another job.” (11:21)

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Notable Quotes & Memorable Moments

• “Airbnb is definitely not dead. It's not just Airbnb…people will always travel and people want the optionality to stay in a nice home instead of a hotel.” — Michael (02:36)
• “I did that five times last year…saved well over a million bucks in actual taxes.” — Michael on accelerated depreciation (06:12)
• “I remember…we were financially free in 12 months of our first investment…just three Airbnbs.” — Michael (10:08)
• “I could own less properties that are higher quality. I get better guests. They pay more at bigger tax.” (03:24)
• “Taxes are the single thing that kill most Americans’ ability to accumulate wealth in their lifetime.” (05:33)
• “Return on equity goes down because your cash flow is not going to increase at the same rate that the home is appreciating.” (07:20)
• “You don’t have job security anymore…Even during COVID … Google laid off thousands of people in my department.” (12:18)
• “AI is getting better and better for guest messaging…It will also flag how pissed off they are, and it will color code it.” (14:31)
• “It's kind of like Monopoly, right? You don't just buy Park Place or Boardwalk…and charge base rent because you ran out of money.” (23:16)
• “If you go away, your business goes away. At some point, you have to hire someone on your team.” (34:38)

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Timestamps for Important Segments

• 01:09 – State of short-term rentals, why experience matters
• 02:20 – Michael’s current portfolio and management company
• 04:10 – Financing strategies and creative tax savings
• 05:36 – Accelerated depreciation, tax strategies, and real-world impact
• 10:07 – Financially free with three Airbnbs, quitting W2
• 13:38 – Use of AI in real estate lead generation
• 14:31 – AI for guest messaging and maintenance
• 22:41 – Student success and the emotional impact of tax refunds, mindset shift
• 23:28 – Monopoly analogy for investing smart in real estate
• 25:43 – Real estate as the great equalizer
• 26:56 – BNB Turnkey service for high-income clients
• 29:13 – Stricter lending environment post-’08, difficulties for entrepreneurs
• 34:38 – From solo to entrepreneur, importance of team building
• 35:25 – Outsourcing, location/time freedom as entrepreneur

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Flow and Tone

• Authentic & Conversational: Sean and Michael keep things real, often using humor and personal stories while diving into technical topics.
• No-Nonsense Encouragement: Michael is direct but encouraging, offering actionable advice and cautioning against common mistakes.
• Relatable Reality Checks: Both touch on the limitations of both W2 jobs and get-rich-quick thinking, emphasizing deliberate scaling, tax education, and the virtues of real estate for lasting wealth.

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Transcript

[A]

One sketchiest place was actually up this random road near Olympic national park. And there was, like, needles. We got to get out of here. I think we're going to get murdered.

[B]

A lot of disappearances in these national parks. Sometimes when you're hiking that far in,

[A]

you're like, dude, a lot of people go missing.

[B]

Like, you'd be dead. Okay, guys, got Michael on. Today we're going to talk about saving money on taxes, scaling business, and all that fun stuff. Thanks for coming, man.

[A]

Yeah, brother. Thanks for having me. Yeah.

[B]

How's. How's Vegas been so far for you?

[A]

It's been. Been fun. Some good food. I got in late last night, but had a good breakfast and walked around a bit and then been on a couple other podcasts. We're hosting an event this weekend.

[B]

Oh, nice.

[A]

For our clients, so that'll be fun.

[B]

You went on the circuit. I saw you on Bradley and Pineda.

[A]

Yeah.

[B]

Those are all the biggest business shows in Vegas. Yeah. Planned it well, man.

[A]

Yeah.

[B]

What's your event about this week, though?

[A]

All things short term rentals and scaling. Scaling investment, scaling business. So these are all my paid clients that are already have one or multiple properties that are looking to take it to the next level and really scale. So tax savings, like the whole nine yards with it.

[B]

Yeah. Let's get an update on the rental business, because I haven't had a real estate guy on in a while. So what's going on with Airbnb, short term rentals, all that?

[A]

Yeah, I mean, generally speaking, still really, really good investment to make, for many different reasons, more competitive now. So, like, if you want to do well, you have to build an experience. I think people are craving experiences more now than they ever have.

[B]

Yep.

[A]

Everyone's, you know, inundated on their phones and with AI, and it's like you lose touch with just like being outside, being with people, doing things, putting your phone down. So if we're able to curate an amazing experience, that's what people will pay for.

[B]

Agreed. When I. Because I'm a customer of Airbnb, like, when I'm spending thousands on a property, I want an experience. Yeah.

[A]

You know what I mean? Yeah.

[B]

What's unique about this property?

[A]

So, yeah, for sure. And we've. We've gone as far as I've built turf golf courses on my properties. Turf wiffle ball fields.

[B]

That's expensive. Crazy stuff.

[A]

Yeah. Expensive. But the ROI is there for it because it's one of one. No one else has that in that market, let alone very few in the whole country that have that type of amenity and you stack it with other things. And now we attract micro weddings, corporate retreats.

[B]

Wow.

[A]

Multi generational travel where we're not competing with hotels or most of the market, frankly, because they're getting a one of, one of a kind experience here and get to experience things that they wouldn't get to experience at home.

[B]

Yeah.

[A]

All right.

[B]

Yeah. And you got over 650 properties right now, right?

[A]

Under management. Yeah. So I own 14 properties worth, you know, $30 million or so. So a lot of them are the higher tier properties, higher caliber properties, but 650 plus properties under management with our management company and pacing to do between 80 and $100 million this year in bookings.

[B]

Insane.

[A]

Yeah. Airbnb is definitely not dead now. It's not just Airbnb. Right. We have direct bookings, verbo booking.com, all these other OTAs. Airbnb just kind of has the, know the market for the name.

[B]

Yeah, I kept hearing it was dead. It was dead. But that's probably for like the lower tier markets, right?

[A]

Yeah, yeah.

[B]

When you're playing at this level, I feel like the margins are higher.

[A]

You could take more. I mean, people will always travel. Right. And people want the optionality to stay in a nice home instead of a hotel. But it's getting more competitive. But there's a lot of average properties that would have worked 10 years ago, they don't work now.

[B]

Right.

[A]

And the more properties that enter the market, especially in that middle tier, well, they're, they're getting compressed. So they have to compete on pricing to get booked.

[B]

That makes sense.

[A]

That's the worst place to be in any business. Right.

[B]

You never want to be competing on price. I learned that from Hormozi. Never. That's how you. It's a race to the bottom, Lisa. Yeah.

[A]

You definitely want to sell on premium. And then I could own less of them too. Yeah, I'd rather own less properties that are higher quality. I get better guests. They pay more at bigger tax.

[B]

Absolutely. Yeah. Certain cities also, I just feel like they're better for houses versus hotels.

[A]

Yeah.

[B]

Is that what you focus on when you ask about.

[A]

My personal investments are now mostly in traditional vacation markets. And I really focus on places that are derived to from growing metro areas. So multiple cities. Where? Like a good example is the Southeast, because Tennessee, North Carolina, South Carolina, Atlanta, Georgia, all growing tremendously over the past decade. So when people move there, what are they going to do? Look up where to visit. So they go to the mountains, they'll go to the Beach. So if you can set up a great property there, well, that creates sustained demand over time, increased demand, because the populations are growing. Yeah.

[B]

When it comes to getting properties, I know there's all sorts of methods, creative financing, putting down certain percent. What. What's the approach we like to take?

[A]

I've done a little bit of everything, but most of them are just traditional financing. We'll get conventional loan or a DSCR loan. 10 to 20% down.

[B]

Okay. Nothing fancy there. No, I think what you're. You're known for is saving on the back end, Right?

[A]

Yeah.

[B]

How you can save money that way.

[A]

Oh, yeah, yeah. So what I love about short term rentals is the. It's a great cash flow vehicle. You can make 15, 20 plus percent cash on, cash return on the money invested. But what most people don't know is it's pretty much the only investment vehicle for a normal W2 earner or business owner where they can have a massive tax write off year one and carry over those losses against their active income. Ordinarily, those losses only count against passive income, I. E. Real estate income. Right. So here's where it gets interesting. If you're making $100,000 a year and you're paying 20,000 in taxes, well, you can go buy a property it on Airbnb. The average length of stay has to be seven days or less. And you have to materially participate in it at least 100 hours a year, as long as it's more time than Anyone else, or 500 hours a year total. And then you could accelerate the depreciation and take a massive loss of like $100,000 plus and reduce all of your income and wipe out all of your taxes. So think about that. The second part to that is you're not just saving 20 grand. It's taxes are the single thing that kill most Americans. Ability to accumulate wealth in their lifetime.

[B]

Yeah.

[A]

If you save 20,000 invested into the market at 10%, that's a million bucks in 42 years. So if you did that multiple times the next several years, that dramatically changes the trajectory of your wealth accumulation throughout life.

[B]

We got to talk after this. I just paid 400.

[A]

Yeah.

[B]

Today.

[A]

Yeah, it's.

[B]

It's tax season.

[A]

Yep.

[B]

I hurt. I hurt a lot. Yeah.

[A]

Get you into a big property, man. Because one property last year, I had five set up last year. One $1.7 million in depreciation the first year. Saved me 700 grand in tax.

[B]

Holy crap.

[A]

Just buying it. I did that five times last year.

[B]

Wow. So you can stack It.

[A]

Yeah. So I saved well over a million bucks in actual taxes on my acting.

[B]

That's nuts. And you. It's an asset and it's right.

[A]

And they cash flow and appreciate over time. So instead it gets paid down too. So. Yeah.

[B]

So instead of just burning the money, you're actually using it towards something productive too. It's like a win win.

[A]

Yep.

[B]

That's unbeatable, man. Holy crap.

[A]

Yeah.

[B]

That hurt bad. No one teaches this stuff, though.

[A]

Yeah, I think it's. It's hard for most people because the ordinary income earner has withholdings on their taxes, so they don't see it. They just get what's left over. Right. When you're a business owner like yourself, it hurts a lot worse when you got to go stroke a check quarterly. Right. Or at the end of the year or April 15th when the time comes around. If most Americans had to do that, I think they'd be much more keen on how painful it is to pay that much in taxes, because most people don't even realize it. It's just like, oh, it's withheld. And this is how much I get on.

[B]

That makes sense. Yeah. I've had a job before. You don't even think about it. You just see the bill and you're like, oh. But yeah, when you're actually running stuff, you notice it night and day difference.

[A]

Yeah.

[B]

Do you pay off your mortgages early or do you let them sit?

[A]

Not right now.

[B]

Probably ran some models on that.

[A]

Right. Yeah. We've actually tapped back into the equity and done refinan to take on bigger mortgages because we had a ton of appreciation that we've either forced in the property or the market went up. So something I look at is return on equity, because usually the return on equity goes down because your cash flow is not going to increase at the same rate that the home is appreciating.

[B]

Got it.

[A]

And also when you do a refinance and you pull money out of the deal, that's tax free because that's debt, not income. So this is where, think the Jeff Bezos, Mark Zuckerberg's of the world, Elon Musk. They can borrow against their equity, their assets, that money's not taxed. So they can take their earned income, if they have any at all, and invest it in other things that give them tax advantages. And then they fund their lifestyle by borrowing against their assets without selling them, so there's no realized capital gain. So Tesla keeps going up. Elon Musk is still making money like that. The Money never left his stock, but he borrows against it, pays a lower interest rate, and uses that money to go buy Twitter.

[B]

Infinite banking, right? Yeah, yeah, it's like a money glitch almost. But you need the assets to pull that off.

[A]

Exactly. So that's why it's important to invest in a hard asset. And the easiest hard asset to invest in is going to be real estate. Because most people aren't going to go start Facebook.

[B]

Yeah, Right. Not many.

[A]

Now you can borrow against your stock portfolio too. We've had a lot of people do that. Security lines of credit. And so again, they're borrowing against it tax free. Now. They pay an interest rate on what's borrowed, but the stock market goes up, they capture those gains, they can go invest in real estate, get the cash flow, get the tax benefit, and then they can go back and pay off the line of credit.

[B]

My buddy just bought a $5 million house borrowing against his crypto portfolio.

[A]

That's crazy.

[B]

Crazy, because if he went to sell that, I mean, crypto's had some crazy gains. He would have had to pay a fortune, millions, probably in taxes, if he were to sell $5 million of crypto. So when I saw that, I was like, man, there's levels to this game.

[A]

Yeah.

[B]

Because the ordinary person would just sell it and pay the tax and.

[A]

Exactly.

[B]

Then take out a mortgage.

[A]

And that's how people create the, the tax free wealth snowball right there. They invest in assets, they don't sell them, they borrow against them. And as it goes up, they borrow more.

[B]

They never sell.

[A]

And also, if you, you know, borrow against, let's say you do a refinance in a property, it's already cash flowing really well, like my properties are. I know I can take on a higher mortgage and of course I'm still going to cash flow. But even if I was breaking even, well, now I have less of a tax liability because I'm not making as much cash flow. And the money I took out was tax free. Now I reinvest into another one. And I started again. So I added the snowball.

[B]

That's embrazed. Yeah. So you said you had 12 properties. 14. 14. And how long of a time period did you buy Those?

[A]

End of 2019 was our first property,

[B]

so about two a year.

[A]

Yeah. The first in the last 12 to 24 months. We've really started scaling a lot faster. We bought four in the first 16 months when we first started. Uh, we were financially free in 12 months of our first investment.

[B]

What?

[A]

Yeah, just three Airbnbs.

[B]

Putting 20 down. You made that back in 12.

[A]

10. 10. So no, the income, the cash flow from the properties far exceeded our living expenses and lifestyle.

[B]

Oh, God.

[A]

Financially. Financially free. And then within 16 months, we got a fourth property and we were cash flowing 30 grand a month. And my wife and I both quit our jobs.

[B]

Wow.

[A]

Never worked again.

[B]

And you were.

[A]

Until we started our other businesses, of course. But financially free. Quit our jobs and then we lived in a camper van, traveled for a year, and then, you know, started having kids.

[B]

So I definitely want to talk about some of those travel stories, but what were your jobs? Were you making decent money?

[A]

Yeah, so I was in sales making 200 plus grand a year.

[B]

Wow.

[A]

And commission only or mostly commission? Yeah.

[B]

So you were good at sales?

[A]

I was okay. I wouldn't say I was greatest.

[B]

Okay.

[A]

I think I worked hard enough to, you know, do a good job.

[B]

I think you're humble. 200k for salesman. That's above that.

[A]

But I started, I started in a great cubicle making 35 grand a year, just like pounding the phone, miserable.

[B]

What were you selling?

[A]

Selling data center software and hardware. That sounds hard. No, I didn't even know what the hell I was selling. I mean, I'm calling these people like Director of Technology, CIOs, CTOs, and I'm just, you know, I get hung up on all the time. People kick rocks.

[B]

Talking to be resilient though.

[A]

But yeah, yeah, but I think what I did now a lot of people should consider. I think people get very comfortable in their jobs or their income, so they stay. And there's nothing wrong with that. But I was once I hit a glass ceiling. I was out and networking, trying to find another job. So I changed jobs and cities in three consecutive years. Wow, 35 grand a year. Then I got a job at Google. I was making almost 100 grand a year. And then I was like, well, I had a glass ceiling. They told me in their, their perf system performance review system. I was like three to five years away from a promotion. And I was like, this is. I'm not going to wait.

[B]

That's a long time.

[A]

So I only stayed there for a year, left, got another job, and then finally was like, okay, I'm making more money now. I'm in a position where I can actually invest and build a future as a way out of.

[B]

Used to get those kind of corporate jobs and think it was safer. Now I think with AI, a lot of these companies are replacing these employees. I don't know if you can make that argument anymore.

[A]

Yeah, I don't think they're safe. Even during COVID actually, right after I left Google, they laid off thousands of people in my department. I think they eliminated the entire like department I was in.

[B]

What department was it?

[A]

It was like an inside sales role that was part of the overall sales division for Google Cloud. Wow. Yeah.

[B]

My mom's at. I probably shouldn't even say this, but yeah, basically big companies are laying off thousands of people and replacing them with AI.

[A]

Yeah.

[B]

So I don't think that job security is there anymore.

[A]

No, no, I don't think so. And I think what I like about short term rentals or really real estate in general, is it's a hard asset. People always need a place to live. When they go on the vacation, they need a place to stay. They crave those experiences. And I think with AI and technology and phones, people are on them so much. Like we were talking earlier, they just, they need or crave those experiences. And also people work remote now, so they have the ability. I have friends or even employees of mine that will buddy up and go stay in an Airbnb for a week or a month at a time to stay in a cool new location during the winter where it's warm and they're from Columbus, Ohio, where they don't want to be during the cold months. Yeah, there's extra demand for it.

[B]

Yeah, for sure, for sure. How are you using AI? Because there's all sorts of ways in real estate. Someone in the sauna yesterday that I met was using it for wholesaling, pulling emails from Zillow and like trying to find properties.

[A]

Yeah, there's a lot of stuff we're working on right now in terms of lead generation for property management company or done for you service, where we're finding properties for people. So there's different things we're working on where we can basically build a buy box, which is like basically what do we look for in a property in a particular market? So we can make sure it's a high performing property and then take that data from Air DNA or Airbnb, other sites and then correlate it with properties for sale on Zillow or the mls. So it can feed us properties that are pre evaluated, which saves our analysts tens of hours of time a week, I bet. So that's just helping speed it up. And then in terms of like the short term rentals, on the marketing side, it's really more so like guest communication, maintenance issues, flagging them, image recognition and then like photos editing. Photos editing, descriptions, things like that is

[B]

it at that point where it's communicating to the guests now.

[A]

Oh, it's been like that for a while.

[B]

Really. Wow.

[A]

The AI is getting better and better for the guest messaging. But before there was a lot of things that could recognize just simple questions like, what's the WI fi? Or I have this problem, I can't find this. And it would. It would usually solve most of it. That's impressive. And then what it can do is it can also flag someone on the team if it can't answer the question or if it can. There's different softwares out there that'll actually determine the guest satisfaction or how pissed off they are. And it will rank it or color code it and so you can rank, you know, which ones you need to tackle first from an operations perspective.

[B]

That's cool, man. Yeah, I had it. I have it hooked up to my email now.

[A]

It's crazy.

[B]

It's answering most of my emails. It's filtering the spam. If it's like, if it doesn't know how to answer it, it'll send it to my Gmail.

[A]

Yeah.

[B]

And I'll answer it.

[A]

What are you using for that instantly?

[B]

It's called an AI agent.

[A]

Yeah.

[B]

Do you have any AI agents working for you?

[A]

I don't like for like that use case at all.

[B]

I have six right now.

[A]

Are you doing like openclaw or what?

[B]

Oh, no, that's. That's a different AI agent. Manuscript man. Oh, yeah, yeah. Dan Martell has been talking about it a lot. I have one that does research on the guests. So I'll watch their recent podcast, scroll through their social media, pull, pull up viral topics. That's how I came up with some of these. I have one that emails sponsors for the podcast and it's already closed a few, which is crazy.

[A]

Wow.

[B]

One that gets guests. So like one that scrolls through YouTube and like pulls the most viral 10 episodes of every day of podcasts, summarizes it, pulls the guests lists out all the sponsors. It's freaking crazy, dude.

[A]

It is crazy. Like where it would have taken what, hundreds of hours of someone's time before?

[B]

Would have taken a va that barely speaks English to do it. Probably would have cost more to be honest. These AI agents are super cheap.

[A]

Crazy.

[B]

You know, I'm using Hormozy's AI non stop right now. I know people that have made millions with Hormozy's AI. There's one in this building that I just met.

[A]

Crazy, dude.

[B]

AI.

[A]

Look at that.

[B]

Yeah, it's nuts. You should play around with it. Yeah, that's the most expensive one. It's like a thousand a month. But I think it's worth it.

[A]

Yeah. I mean, if you're a business owner and it can help increase productivity, increase revenue, you know. I changed a little cheaper than employee.

[B]

Way cheaper. I changed my whole site based off what it said. I changed my whole funnel, change my sales scripts. It's freaking insane, dude. Times are crazy.

[A]

Yeah.

[B]

But real estate is, is tried and tested. I don't think AI will impact it as much as other industries. Yeah, I think you'll be good.

[A]

Yeah. Hopefully.

[B]

Unless they start buying up all the houses. Go Terminator on us.

[A]

Yeah.

[B]

Right. VCs are doing that, but it doesn't really affect you, right?

[A]

No, not so much. They're not. They're playing more in the hospitality space now.

[B]

Yeah.

[A]

Private equity and other groups, but not, not as much. And they're not doing it at this level with as much, you know, detail.

[B]

Yeah.

[A]

Into the experience that we're providing. I think usually they're buying like bulk single family homes or apartment buildings.

[B]

Is your end goal to sell this to a company?

[A]

I think my business is. The end goal would be to exit or have a partial exit and then get a good partner to come in. We take chips off the table and then we can grow it, you know.

[B]

How's that happening? Space yet?

[A]

Oh, in the property management space for sure. Oh, yeah, yeah, yeah. Property management companies trade at a really high valuation compared to at any most service businesses because they have the recurring income on the management contracts that makes

[B]

it like 10x more valuable, honestly.

[A]

Right.

[B]

What's what, how many properties would you need to get to to start getting some, some offers?

[A]

I mean, there's just different levels. Right. If you're under a million dollars in EBITDA, you're, you know, you're trading probably less than 3x on EBITDA. But once you get to like 5 to 8, 10 million, then it really starts to crank up. Once you're over 10 million, like 10x probably becomes the floor. You have a sound business and, you know, C suite in place and they'll trade as high as 15 to 17x.

[B]

Wow. Who would have thought from my sales room you'd be here, man. Yeah, well done. Making 35k a year to now this.

[A]

Yeah, it's crazy. It's crazy.

[B]

You and the wife too?

[A]

Yeah, my wife was a autopsy technician.

[B]

What?

[A]

Yeah, first job, Domino's was her longest standing job. Then she got into doing autopsies at the morgue. So she worked In North Carolina, Dallas, and Austin, Texas, morgues.

[B]

So she's seen some, man.

[A]

Oh, oh, she's seen some stuff. It's funny. In Dallas, Texas, she had me create a spreadsheet for her to track all the different cases that she was doing. Not so much the cases, but, like, the different intricacies of each case and which doctor did it. She was for herself. She just wanted to, like, build this thing. So here I am building a spreadsheet for how much she's cutting up dead people.

[B]

Holy crap, Dash.

[A]

But she's got some wild stories. She'd come home and tell me to, you know, hey, smell my hair. Do I smell like decomp? And I'm like, get away from me by decomposition. Yes, exactly that. Yeah. I get in the shower. Might have to get her on next. Yeah, she's got some wild stories, man. So, yeah, Dinner conversations were always more interesting with her. Well, how was your day? She told me all this crazy. How's your day? I'm like, just pretty boring.

[B]

Sat. I sold people on whatever you were selling at the time. What? You said you traveled for a year.

[A]

Yeah.

[B]

Was it planned out to the T or were you spontaneous with it?

[A]

A little bit of both. My wife's very type A planner, so she. We more or less had dots on a map. We actually had a map at the bottom of our stairwell the year before. And we said, our goal is to scale this business, our properties, and once we quit our jobs, we're going to plan a route on the pins on the map.

[B]

That's awesome.

[A]

And we actually did it, which was cool. So we. Most of the travel was spent on the western half of the US because we grew up on the east coast and hadn't traveled much on the west. So we traveled, I mean, pretty much every state on the western half. Hiked over 400 miles, visited over 20 national parks.

[B]

You weren't working at all. You were just living up?

[A]

Yeah, just had our properties, but, like, maybe an hour a week to manage from our phone. That's cool.

[B]

See any UFOs or any crazy stuff?

[A]

No, nothing crazy there. Some sketchy places we slept in. I bet we're off grid. Off grid a lot.

[B]

But where was the sketchiest?

[A]

There was one Walmart parking lot that was a little sketchy. One sketchiest place was actually up this random road near Olympic. I think it was Olympic National Park. And we could not find a place to pull off. And it was late at night, and we finally, finally found a place to pull into, and we backed in and there was like needles. There was a whole fish just sitting there. Like someone was about to like eat a fish, I guess. And it was just. And trash everywhere by the water. Like, I was like, we gotta get out of here. I think we're gonna get murdered.

[B]

Yeah, that sounds awful.

[A]

Very sketchy. We were not near water. This is like up on a hill, like on a mountain. And there was just a branch. There's just a giant fish.

[B]

Yeah. That guy might eat people. Yeah. They say in these parks, in these national parks, there's some like, what they

[A]

call them a certain word. Yeah.

[B]

There's a group of people that eats people. A lot of disappearances in these national parks. Yeah.

[A]

I don't doubt there's some crazy people out there.

[B]

Yeah. Sometimes when you're hiking that far in,

[A]

you're like, dude, a lot of people go missing.

[B]

Yeah, I could die. Like if you break your leg, they say, or your foot, like, you'd be dead.

[A]

Yeah.

[B]

If you're like 10, 20 miles in. Yeah. You know, and you're by yourself, I mean, you had your wife, so like

[A]

a horse you got to get put down.

[B]

Yeah. You'd be fine.

[A]

Damn.

[B]

A year off of work. I don't know if I could do that. It's like a sabatical.

[A]

Yeah, kind of. Yeah. I mean, then we started investing again and she got pregnant. Like, might as well settle down. I either need a bigger van or a house. So then we bought a house and I. During that year, I also started my first online business as well, teaching people how to invest in short term rentals, which has been great. So over the years I've. That's grown and grown. So I've taught over 3,000 people.

[B]

Wow.

[A]

Across the world. How to do short term rentals. With over $1 billion in real estate acquired.

[B]

Yeah. I'm sure you got some great case studies and testimony.

[A]

Oh, yeah, yeah. It's great. It's really cool to help people get into something like, I mean, it's. It's real estate, but it's also hospitality. So it's really their first business. And most of them are just W2 earners.

[B]

Yeah.

[A]

So to give them something of their own. Not give them, but teach them how to build something of their own. And they get the cash with the tax benefits. And a lot of them have, you know, replaced their jobs or their spouse's jobs so they could stay home, do whatever, travel, spend more time with their kids. So that, that's really fulfilling for me to help people do it and succeed. And then it's also A great business to be in.

[B]

Yeah. What do people struggle with the most when they're getting into this?

[A]

Understanding how to find and evaluate deals. That's really it.

[B]

Yeah. Teaches you how to do that other than you. Yeah.

[A]

And then the secondary thing to that is how to set them up to be an experienced rental. Because most people will buy a property that looks nice or something they want to stay in and then they skip. Maybe they buy a bigger property and they, they lose some of their budget on the higher down payment and they can't put the right amenities or design it well enough. And then it struggles and they're like, oh, this sucks. Everything is dead. Oh, it's not the case. You should have just bought a two bedroom place, made it a badass top 1% performing property and you'd be making a ton of money.

[B]

Yeah.

[A]

It's kind of like Monopoly, right. You don't just buy park place or Boardwalk and, you know, charge base rent because you ran out of money. You have enough money to hopefully build the houses and put the hotel on it so you can charge a shit ton of money and win the game.

[B]

Classic.

[A]

So think about the market is the Monopoly board. It doesn't matter which card you want on the board, you want the ones that you can build a hotel on.

[B]

Yeah. One of the best board games of all time.

[A]

Yeah.

[B]

Teaches you a lot about real world.

[A]

Yeah. More fun to play in real life.

[B]

Yeah, yeah, definitely. You're making actual money in real life. So they get their first property and then do a lot of these guys get more for that or do you kind of.

[A]

Oh, yeah, yeah. They get, they get the bug.

[B]

You know, you get one.

[A]

Yeah. Once you get one and it's doing well and people are surprised all the time. We'll get text messages from our clients. Like, I just listed, I got five bookings, 20 grand. It's like, is this real life?

[B]

Yeah.

[A]

It's crazy because they're not used to that. They're used to trading their time for money. I go to work, I work a certain number of hours and I get paid. But when you set something up, you work hard to set it up. Right. And then money just starts flowing in. Then we have people that take their first vacation since they had their first property and they're like, I'm making money on vacation.

[B]

That's the best.

[A]

It's life changer. I remember. Then they get the tax refund. Yeah. That's crazy. So I had a client, first property was bought last year and he just sent a screen. I actually Posted on his own social media. He got a $42,000 refund, 40 grand from the IRS, and $2,000 from the state of Utah. So he sent the screenshot and he was like, this is crazy.

[B]

That's a lot.

[A]

So you learn about it in from listening to me in the coaching program or on social media, but when it actually happens and that money comes back into your account, you're like, holy shit. So that money reinvested, you know, turns into millions of dollars over your life.

[B]

The compound. Yeah, absolutely. Yeah. I, I believe in passive income. I know that's like a controversial take, but. Yeah, some people don't think it exists, but I think if you put in the time up front and then you start making money off the back with no active time invested, I consider that kind of passive.

[A]

Yeah, yeah. I think there's like compound income where the bigger it grows. Like, usually you should be able to remove yourself from any type of operational work. I mean, there is path true passive income, but, you know, a lot of the big income is going to be active for most people. Yeah, I agree.

[B]

I mean, my buddy just invests. He invested into prize picks, I think it was. Have you heard of that company they just exited? He made $20 million. So, like, I consider that passive because, yeah, he got in when they were worth 20 million, they sold for 4 billion.

[A]

That's insane.

[B]

Insane. Made me want to start investing into VC stuff.

[A]

But, yeah, see, that's, that's, that's the tough part. A lot of listeners are probably like, well, I can never invest in something like that because how do I have access? So that's part of the reason why a lot of rich people get richer is because they have access to connections. So that's why I love real estate, is because it's one investment vehicle that levels the playing field. You get the cash flow, you get the appreciation, you get any leverage, and you get the tax savings. And you can, you can play the same game as they're playing.

[B]

Yeah, there's no gatekeeping, I guess, with real estate, Right? Unless you're going for, like, some crazy properties.

[A]

Yeah, sure. I get. You can always raise money for it. And then you're gonna have to learn how to raise money or do a fun.

[B]

I'm sure you considered that at one point.

[A]

Yeah, yeah, we. We went down that rabbit hole, but then we ended up pivoting to doing our BNB turnkey offer, which is a bit different. So we thought about doing a fund which is raising 20 million, $100 million, whatever. And then Going and buying hotels or buying short term rentals. But instead we're like, that's what everyone else does. What if we offered a service where the individual buys the Property, they own 100 of it, there's no profit or equity split and we just do as a service and they get 100 of the tax benefit in the cash flow and they have a place if they want to visit a badass rental, it's theirs to stay wherever they whenever more scalable that way.

[B]

Right? Yeah.

[A]

So that, that service is blown up typically for higher income earners because it's a white glove service. We're going after bigger properties.

[B]

Yeah.

[A]

But we've worked with entrepreneurs, high income earners, professional athletes, A lot of NFL players have used the service, which is really, really cool. So they get something that's theirs because most things that their financial advisor puts in front of them or on their plate are going to be syndications, funds, mutual funds, individual stocks or other investment strategies. Maybe startup companies like get into like BC thing or that's like a small

[B]

percentage of what gets pitched.

[A]

So this is like something that they own and they have, they can kind of be more, more into it.

[B]

Yeah.

[A]

Hey, this is what I want the property to look like. They have more say, which is really cool.

[B]

Funds never appeal to me, to be honest.

[A]

Yeah, you have no control.

[B]

No control, no liquidity. It's usually 8 to 10, 12.

[A]

There's a lot of hidden fees baked into funds a lot people are not aware of.

[B]

Yes. You're actually not even making 10, 12%.

[A]

Yeah. So.

[B]

But the liquidity to me was the biggest issue with it.

[A]

Like that's something I've run into lately because I invest so heavily into real estate, which is an illiquid asset. I can't just place a sell order and get my money back in two days. I got to list it for sale and then pay, you know, taxes or recapture if I did the cost seg study. So as a business owner, I make high income and I want to avoid paying taxes. So I invest so heavily into real estate, which cash flows, which is great. But let's say there was a downfall in the economy or my businesses had a really bad quarter. Well, I still got to pay employees and everyone else I might not get paid. So my illiquidity can be a problem. So I'm shifting some of my investments to more liquid assets to kind of safeguard my job and my family and my businesses in case of a rough.

[B]

Yeah, yeah, that makes sense. If another.08 happens. Yeah, that'd be Rough.

[A]

Yeah.

[B]

You were young during that recession. I was in elementary school.

[A]

Yeah.

[B]

How old were you?

[A]

08, I think I was freshman in high school. Yeah. Okay.

[B]

So you didn't really experience it from a business point of view. No. Yeah. I always wonder if that happens again, what the hell would happen? That. That was crazy. I have, like, childhood memories from that. Like, so many people getting screwed.

[A]

Yeah. I had friends that, at the time, I was like, why are they selling their house? And, like, a lot of things were tightening up. Yeah. Looking back, it was like, oh, it was 0809.

[B]

Yeah.

[A]

But I don't think real estate's not in that position right now. That was built on terrible lending. The loans or loans were awful.

[B]

Now people were hard to get a loan.

[A]

It's hard to get a loan. Yeah. Very hard.

[B]

Well, especially for entrepreneurs.

[A]

Yeah.

[B]

Because we hide our. Not hide, but like, we do a lot of loopholes. So our income is low on paper one.

[A]

Yeah.

[B]

Business owners. Yeah. So for me, getting a loan was hard.

[A]

Yeah.

[B]

You know, through the bank.

[A]

I'm like, what did you end up having to do? Bank statement. I had to do a bank statement loan.

[B]

Yeah. Because my income was low, but my. My cash flow was solid.

[A]

Yeah.

[B]

So I couldn't qualify for my house basically. Off a regular loan.

[A]

Yeah.

[B]

Because my income was too low.

[A]

Yeah.

[B]

But I feel like that's a common issue for entrepreneurs.

[A]

Yeah. Yeah. A lot of people end up doing that bank statement loan. Submit a bunch of PNLs.

[B]

A lot of.

[A]

Yeah.

[B]

Like 24 months of bank statements.

[A]

Yeah.

[B]

I had to be organized.

[A]

We just qualified for a few of those similar ones for investment properties and for a new primary residence. And my assistant hates me. But, I mean, every time it's like well over a hundred statement home payments because I have different bank accounts for each one of my rentals. Geez. And multiple bank accounts for my different businesses. So you're talking 12 months plus of bank statements for every single account.

[B]

That's crazy.

[A]

Yeah.

[B]

That's a mess, bro.

[A]

Yeah. She did great.

[B]

Yeah. Shout out to.

[A]

Shout out to Melissa.

[B]

Melissa, you're the best assistant of all time, man. Until AI replace. No, I'm just kidding.

[A]

You know, she's. She's irreplaceable. She's amazing.

[B]

Yeah. There's certain things that are irreplaceable.

[A]

Yeah.

[B]

You know, I think what you do is going to be hard to replace. Same with podcasting. Yeah. Investing people are using it for stocks and stuff now. I don't know. We'll see.

[A]

It's better. But Yeah, I feel like that can get dangerous though.

[B]

Very.

[A]

I think. Oh, I just woke up and I lost a hundred thousand dollars because of a glitch.

[B]

It happened to me.

[A]

Yeah.

[B]

I had an AI trading forex for me like years ago. Really lost like six figures. It was making solid money for a

[A]

while, like four or five. What happened when it lost money?

[B]

It lost it all.

[A]

But like, what, what caused it?

[B]

I still don't know. Just that day, something. It could have been a news cycle that. Just a lot of fear in the market and it screwed up the algorithm, but it was making like 8% a month for four or five months straight, which is crazy.

[A]

Yeah.

[B]

And then lost it all in one day.

[A]

That's crazy. Wrecked.

[B]

That hurt. So I don't know if I'll be using AI Trader anytime soon. Yeah, I'm sure they've gotten better. How could people watching this get involved with you?

[A]

If they're interested, There's a lot of different ways, just various businesses. I'd say if you want to get into short term rentals, especially for cash flow and tax savings, there's really two routes. You know, I can do it with you. I can do it for you if you. If you didn't want to do it on your own. So BNB Investor Academy teaches you how to do it. Very hands on, very high success rate. And then BNB turnkey. Typically people who have $250,000 or more in cash or liquidity that are busy with jobs, family, profession, and they just want someone else to find the property, set it up, do all their construction, and then manage it on the back end for them.

[B]

Nice. Well, you got links for those. We'll include those in the video in the description. Yep. And Instagram, can people hit you up there?

[A]

Oh yeah, yeah. I'm very active on Instagram.

[B]

Yeah, that's how I found you.

[A]

Yeah.

[B]

Yeah, you're very active, man. I used to see your ad all the time.

[A]

Yeah, yeah, there you go.

[B]

Yeah, you target. I'm targeting the right people. Yeah, you got to show me who you're targeting because I need that list. I'm running ads right now. We get some interesting calls.

[A]

Oh, I bet you do.

[B]

Yeah, I'm sure you get those too.

[A]

Yeah.

[B]

Oh yeah, someone was in rehab, called us.

[A]

Interesting. Yeah, I have a great story to tell.

[B]

Yeah, that was a fun one.

[A]

That's different marketing for a podcast. Guess. Yeah, you probably get all sorts of.

[B]

All sorts through that funnel. All sorts, yeah. Everyone thinks they have the greatest story of all time too. So. Yeah, deal with that. But it's part of the game, man. What's next for you, though?

[A]

Right now, just focusing on business stuff. Family. I got two little kids at home. I just try and maximize life nice and not life maxing like you see on Instagram. Like, yeah, let me go buy a bunch of cars and do all this crazy stuff. But it's really more like the quality of life. I want to live the highest quality life possible. So setting ourselves up for that. We're working on building a breaking ground on a new construction for our primary home, which will be our forever home. Congrats. Which is cool down 50 acres through. Holy. Three bodies of water.

[B]

Let's go.

[A]

Yeah.

[B]

Three bodies of water. That's a flex.

[A]

Yeah. So it'll be fun. So that's. That's what's up there. And then the business stuff, it would be interesting. We'll entertain, putting our business or collective of businesses out to market, depending on how things are going, and just kind of see what kind of interest we get.

[B]

That's cool, man. You think you'll ever retire again?

[A]

Yeah, I mean, is, you know, I don't. I don't work a ton of hours now. How many hours? It fluctuates on average. You get a different answer if you ask me or my wife. But I would probably say like 20. 20.

[B]

Yeah. Working hours objective, especially some people, like, consider this work or they don't like watching the YouTube videos.

[A]

I'd say if I'm, like, in front of my computer or on calls or doing something like active recording videos, ads, stuff like that. 20 hours, that's nothing, dude. Yeah.

[B]

Well done. So you've really outsourced all the.

[A]

Yeah, it comes with great employees, too. It's hard to hire great people and retain them very. But we pay our employees well, and we have low attrition across all of our companies because of that.

[B]

Well done. Yeah, that's. That's the dream, man.

[A]

If you don't have that, it's really hard to go from solopreneur to entrepreneur because a lot of people think, like, I'm an entrepreneur, you know, but if you're. You are sales, marketing your operations, you're everything. Like, if you go away, your business goes away. And there's nothing wrong with that because usually your margins are crazy high. But at some point, you have to hire someone on your team, even if it's an assistant or, you know, operations manager, 100%.

[B]

I was stuck in that solopreneur phase for almost a decade, and this pod is what got me out of that. And I've outsourced as much as I can. Obviously, it's hard as a podcast. I still need to physically shoot. But you could build up a backlog and outsource a lot.

[A]

Yeah, but like the editing and all of it, getting people on the podcast, you know, the funnel.

[B]

I just do the prep and the filming.

[A]

Yeah.

[B]

Everything else is pretty much outsourced, which is great because then you have location, time, freedom. What was the third freedom? I forgot. But I could basically travel wherever I want, whenever.

[A]

Yeah, it's great, dude.

[B]

I'm not bound. You know, a lot of people are bound physically or time on a schedule. I wake up usually whenever I make my own schedule. Yeah, it's the best, dude.

[A]

Yeah. I definitely could not imagine going back to a 9 to 5, especially in office job.

[B]

Hell, no. I've never worked a traditional 9 to 5. I did have one job because I sold my company a few years ago and it was an aqua hire. And I won't talk too bad on that because he watches the podcast, but wasn't my favorite setting, you know?

[A]

Yeah.

[B]

Working traditional hours, being on a desk.

[A]

Yeah, it's tough.

[B]

It's tough, man. But, dude, this was great. We'll link everything below. Anything else you want to close off with your. No.

[A]

Yeah. Appreciate you having me on.

[B]

Absolutely. I'll buy some real estate next year. Inspire. Hey, we'll help you out, man.

[A]

Yeah, I need to save you some money. No more $400,000 check.

[B]

Paying more in tax than Trump and Elon and you and everyone else, man. Check them out, guys. Peace. Thanks for watching all the way to the end, guys, please hit like and subscribe. It helps us grow the show and helps us get bigger guests. Thank you so much.