(chainsaw growls) - I really started to realize that I wanted to quit my job when I just wasn't able to produce work.

Timber!

You know, advertising is such a cutthroat industry and you pitch your idea.

Then you pitch your ideas, and you pitch your ideas, and 99.9% of those ideas never see the light of day.

From the get go, I sort of knew that I was never going to be the best at it.

And I pitched, to my wife, this crazy idea.

"What if we just moved to Tennessee, on 50 acres, and built a tiny house village and quit our jobs?"

Why, why.

Why Tennessee?

And it's very simple.

Gatlinburg, Tennessee, is home to the hottest Airbnb market in the country.

12.9 million people visit the Smokey Mountains every single year.

So this is the hotbed for short-term rentals.

That wasn't an easy pitch, but she's always been very supportive of me.

And she understands that when I am set on something, it is impossible to get me off of that dream.

- The short-term rental industry is a major part of the sharing economy.

Property owners can easily offer up their homes, or spare rooms, to renters looking for a unique stay, and the websites that act as middlemen, like Airbnb and VRBO, have seen remarkable growth over the last 10 years, with over 660,000 listings in the US on Airbnb alone.

In fact, Julia and I have one booked for later this month.

- Today, Rob has a thriving, short-term rental and real estate development business, and even offers a course for aspiring superhosts, but, like many others, he originally got into the industry just as a way to supplement his mortgage payments.

- [Rob] We were about $80,000 in student loan debt.

Our monthly's on that were about a thousand dollars a month.

I told my wife, "I cannot bear to pay a landlord almost $2,000, a month, to live in 600 square feet.

I think if we buy this house, we can rent out that little studio space on Airbnb and make $2-$3,000 a month", which was the equivalent of 50% to 75% of our $4,000 mortgage.

I needed this to work.

I needed it to work, or else we were going to be in a very bad spot, financially.

And when it did work, I was like, "Whoa, what if we did this again?"

Here's what we're going to do.

We're going to build a tiny house in our backyard.

I'm going to take out a loan, it's high interest.

It's 7.54%.

And that loan was for $45,000.

At about the $45,000 mark, I had to kick out my crew.

And so I finished the rest of my tiny house.

And by the end of it, that tiny house cost me $72,000.

Yeah.

I mean, I had to put, you know, $16,000 on a credit card, and I had to use everything that was in our savings to do it, but I'm so glad that I did.

Today, I own one tiny house in LA.

I own a tiny house in Joshua Tree, California.

I own a tiny A-frame glamping experience in Arizona.

I also own a yurt in Arizona, two bell tents, and a vintage Airstream.

And, at the moment, I'm slated to build eight tiny houses down at the bottom of my property, here in Tennessee, where I personally live.

I have been able to carve a niche out in real estate, whether it be constructing tiny homes from the ground up, or glampsites and national parks, where the returns are really, really good.

- [Julia] Even though job security fell sharply during the pandemic, the first half of 2021 has seen an unprecedented surge of workers quitting their jobs.

Some want to change careers, others have gone back to school, and many plan to start their own businesses.

Like Rob, the majority of these entrepreneurs use debt to build their businesses, and often dip into their personal savings to stay afloat.

And, though the financial stakes are high, very few say that their main motivation is money.

- You know, I had a great job and I was really happy with that.

I was a copywriter in an advertising agency and that's something that I really, really loved, because I really enjoyed being creative.

- Check it.

♪ Front, side, need airbags ♪ But as I really went through that career path, I really found that it wasn't as creative as I thought it was going to be, just because I had to run my creative ideas through so many people.

When I got into the real estate world, I found that that was creativity, you know, that I really, personally connected with.

It was me being able to execute my entire creative vision.

I was over here creating my rental portfolio, and succeeding, whereas in advertising I was constantly striking out.

And so I think I just had this turning point where I was just like, "Why am I doing this?"

I mean, I think just in those five minutes of talking to my boss, I was really regretful and I was really scared.

But when I went to bed that night, and I woke up the next morning...

I don't know.

I felt like I did it.

Like I was, like, "Alright, I escaped this thing, that I just wasn't really succeeding at, so that I could finally step into what I was supposed to be doing."

(speaking Spanish) - [Rob] You know, my parents are immigrants.

They came from Mexico, and my dad was a doctor in Mexico.

And when they moved here, my dad could not transfer his MD to America.

So he had to take a minimum wage job.

(speaking Spanish) Occasionally, when they could save up the funds to do it, they would go and buy a house, and they would rehab it, and they would sell it.

So I was used to seeing them in the real estate world, and they could really just never scale up the business, because they were way too busy, making minimum wage, to support my family.

And so I was like, "All right, if they couldn't do it.

I'm going to do it for them."

(speaking Spanish) - [Rob] I will say I do miss health insurance and benefits.

And, to some degree, I do miss the regimented aspects of working a 9 to 5, which is like, I can sit in my chair and make things happen and I can just turn off when I get home.

And that's something that me and my wife talked about recently, was, she doesn't, sort of, miss that, when I got home from work, I never talked about work again.

Okay, I should go work.

Love you.

- Yeah.

I'm sorry.

- I do feel like, as, the caretaker, there's a lot that falls on me.

And so, sometimes it's hard, because, especially because he's at home, it's like, "You're right there.

I wish you could do one of these five things that I'm doing right now."

Give it to me.

- I would say, if I were going to quantify how much I actually work, every single week, I don't know.

I'm ashamed to say like a hundred hours a week, because that really is what it feels like.

- Surveys regularly show that entrepreneurs, and small business owners, work longer hours than salaried employees.

They also tend to be under much more pressure, managing cash flows, employees, and investors.

This can often take a toll on personal relationships.

- My life has changed pretty significantly in the last year.

And now that I'm working with investors, there is more pressure to succeed.

If you have one bad deal, it's kind of like a black eye in the industry, right?

Like you're wounded.

I could never let that happen.

Never.

I could never lose else's dollar.

So when I overextend myself, and take these big risks, and do anything I can to make deals work, it's at the sacrifice of not getting to put my daughter down for her nap.

It's at the sacrifice of not being able to sit down with my wife and my daughter for dinner.

And, that's something that really does hurt, in retrospect, you know, that's something that I do dwell on quite a bit, especially at night, you know, when my daughter's asleep, and my wife is asleep, and I'm alone at my computer, and I'm just like looking through photos of us, like, I get really bummed out, because I'm like, "I kind of feel like I missed it a little bit."

(speaking Spanish) - [Rob] I don't really know when I'm going to stop.

And I don't really know, you know, what is enough, when enough will happen.

I think, for a long time, I had, like, a monetary goal, you know, when I make $5 million, whatever, I can stop.

And I actually don't really put my goals in a monetary form anymore.

I think, for me, ultimately my goal, is I want to be able to take care of my parents for life.

I understand the debt that they've incurred on my behalf.

You know, I want to be able to buy my dad a brand new truck.

I want to be able to buy my mom a brand new house.

And I want them to just relax, because they've spent their entire life working.

(speaking Spanish) - [Julia] According to the Bureau of Labor Statistics, about 20% of small businesses don't survive their first year, and only about half make it past five years.

- And yet, despite the risk, the long hours, and personal sacrifice, the vast majority of self-employed professionals say they would never go back to traditional employment.

- If my ad agency called me on the phone, tomorrow, and said, "Rob, we will offer you $2 million to come back."

It would be an immediate, "No", no questions asked.

I would never, ever go back to 9 to 5.

There's no amount of money in the world that can make me do that.

I have the job that I want.

I have the dream job, and I'm fine with this being my identity.

I'm a dad.

I have a short-term rental business and I teach people all over the world how to do that.

That's my identity.

And I love it.