Small Business Spotlight: Entrepreneur Jonathan Tuttle on Building a Recession-Proof Career

Sep 15, 2020

Our latest Small Business Spotlight guest has spent the last 10 years positioning himself in industries he believes to be recession-proof. Jonathan Tuttle, a Chicago entrepreneur, is a Renaissance man involved in mobile home park investments, digital marketing, and, most recently, HVAC business acquisition.

On this episode of Small Business Spotlight, Jonathan talks about how the challenges of the 2009 recession influenced his career choices, how his varied businesses work together for optimal success, and a lot of great advice to young entrepreneurs.

Navigate the Video

  • 00:22: Introduction and overview of Jonathan’s entrepreneurial avenues
  • 02:15: Jonathan’s mobile home businesses (investment fund and flipping course)
  • 03:52: How Jonathan became involved in digital marketing
  • 05:37: Lessons learned from the 2009 recession
  • 06:52: COVID-19’s business impact and the most recession-proof industries
  • 10:29: The key to success: Diversify your business ventures
  • 11:24: Business formation and the value of an experienced professional (“Money loves speed”)
  • 13:24: Jonathan’s advice to his younger self: Trust your gut

Full Video Transcript

Andrew Gordon: Hi, everyone. This is Andrew Gordon and welcome to another episode of our Small Business Spotlight series. Today I have a great guest with me, Jonathan Tuttle. Hey John, how are you?

Jonathan Tuttle: Good, man. Thanks for having me on. I appreciate it.

Andrew Gordon: Yeah. Thanks for coming. So, you’re a Renaissance man. You’re involved in many different things, and to be honest, I kind of struggle to even introduce you. So if you don’t mind, can you just tell the audience a little bit about yourself and the different things that you’re involved in?

Jonathan Tuttle: Sure. It just comes down to two basic niches: manufactured housing, mobile home parks, and digital marketing, but I’ve got a couple of avenues and businesses in each of those.

Andrew Gordon: Are those two separate businesses or do the two relate to each other?

Jonathan Tuttle: Both. Good question. I have a mobile home park fund, and then I also have an info course teaching regular people how to flip mobile homes. So that ties into the digital side.

And the digital side, I have a couple of e-comm stores, and then also a digital marketing agency, as well.

Andrew Gordon: Got it. So really, you’re just kind of an entrepreneur. You’re involved in many different verticals.

But the mobile home space is really an interesting space, especially now with the COVID pandemic. Can you tell us a little bit about how you got involved in real estate and then also specifically the mobile home space?

Jonathan Tuttle: Sure. Yeah. That’s a great question. About, I would say, 15 years ago, my dad got involved in the space, late on in his career, and kind of discovered it. At about the same time, a few years before that, Warren Buffett started getting in this space and Sam Zell, about a decade before. Two of the best investors in history. So it kind of intrigued me because I was familiar with those guys.

And I just saw during the last…downturn, it was the best performing real estate. That’s what really intrigued me as an avenue, eventually, to get in full time, or at least get some investments involved with that.

Obviously, right now with COVID, a recession’s most likely coming. Everything’s an indication towards that. And this industry thrives during downturns, the mobile home park industry.

Andrew Gordon: Tell me a little bit about how you structure your business in mobile homes.

Jonathan Tuttle: The big thing is the mobile home park fund. We have a $10 million raise right now. We will buy with accredited investors’ capital throughout the Midwest, mainly in the mid-Atlantic. With everyone getting into the space, it’s getting more and more competitive. Luckily, I have all the industry background, experience, and relationships, which is key. It’s a “good old boys” type industry where if you’ve been in the space for a long term, they trust you more. You get the deals, get first access to deals. So that’s the mobile home park industry.

And then I also have a course coming out teaching people how—especially now during COVID—how to flip trailers inside… just how to create a second income.

Andrew Gordon: Flipping real estate, I’d imagine you have to have a good amount of capital, but mobile home parks, I’d imagine the barriers to entry are smaller than just flipping a home.

Jonathan Tuttle: Correct. And that’s the beauty about it. If you beautify a 1970s or ’80s model, and you’re all in for $5,000, you could turn around and sell it for $10,000-15,000 because the only other alternative is buying a $40- or $50,000 new one.

Like you said, you don’t have to have a lot of money. You don’t have to be experienced in real estate, ’cause you’re not tearing down walls and you’re just doing really minor stuff and just using digital to promote it and sell it.

Andrew Gordon: So Jonathan, it sounds like you’re able to use the digital space to also promote mobile home parks or mobile home trailers. Is that correct?

Jonathan Tuttle: Correct. Yeah. And that’s the beauty about it because everyone uses Facebook. There’s, what, 2.2 billion daily users on it? Just the ability to use digital, this space is like so ripe for disruption.

Andrew Gordon: It sounds like you grew up in a family of real estate investors, so it makes sense how you got into that area. But tell me a little bit about digital marketing. How did you originally get into that space?

Jonathan Tuttle: Sure, sure. I do have a top tier digital marketing agency. I really came into the space probably about five years ago. I noticed a need in the marketplace, because I’ve used some of the local Chicagoans. I’m not gonna say names, but the quality of work they put out there is pretty sub par.

And just seeing that as a business owner, as an entrepreneur, I wanted to be able to help people solve those problems. So I went full force, took all the courses, spent six figures on learning it. I have mentors who are the top in the [field], you know some of the guys too. I’ve worked with some of those guys and really learned the space.

Basically, I just want to provide an avenue to help other businesses. With online right now, this is the gold rush right now. If you could do this, it’s all automated, it’s algorithms, it’s building up some teams and the algorithms do all the work. So if you know how to do this, you should be able to do it for yourself, and then you could do it for your clients.

All the people working on my team work on my stuff first. If they’re good, they stay with me for years and they help my clients succeed, but they test on my dollar first, not the client’s dollar.

Andrew Gordon: Got it. So when a customer is out there looking for a digital marketing agency, it sounds like one of the things that you would suggest that they look to is experience. And perhaps even the agency has their own ventures or e-commerce brands so that they could actually demonstrate success rather than it just being theoretical.

Jonathan Tuttle: Correct. Yep.

Andrew Gordon: Interesting.

Jonathan Tuttle: Even when I’m hiring people, it’s six to eight people before I find one. They’ve already gone through a series of tests, but then still six to eight. and I keep the best one.

Andrew Gordon: Interesting. So Jonathan, you’ve got your hands in a variety of different things, from real estate to e-commerce, digital marketing. I’m sure that you’ve faced many challenges in your career, but what is one challenge that you faced and how did you overcome it?

Jonathan Tuttle: One challenge I overcame… I would say the last recession. The last downturn was the biggest learning curve. I thought I was prepared, but everyone was also in bad predicaments, so they’d screw me over and I wouldn’t get paid on deals. It was a bad time… The two industries that did really well were mobile home parks and then also digital, so that’s what kind of got me into both these spaces. I saw that I never wanted to be in that position again.

One skill set—I think this would be a value to a lot of your potential listeners—is understand the psychology. One book I think would be a really good value for a lot of people would be Poor Charlie’s Almanack, which is [by] Warren Buffett’s billionaire partner, longtime business partner.

[It teaches] you how to understand how people think, how they make decisions—just, usually, based on biases—and identify those top 25 biases, and how you can take advantage or help people. Not take advantage of them, like in a bad way, but take advantage to position yourself in the correct light.

Andrew Gordon: So, Jonathan, the COVID pandemic has obviously had a huge impact on a lot of businesses. Can you talk a little bit about how your businesses have been impacted and how you’ve adapted to the situation as well?

Jonathan Tuttle: Yeah. First, I mean, it’s a tough situation for a lot of people, unfortunately, but I’ve been preparing for years. Like I said, from the last recession… I saw that mobile home parks and mobile homes, as well as digital, had no issues during the last downtown, so I made it my mission to get completely involved with those.

So this year has actually been a growth year for me. Right now there’s a statement. Warren Buffet says: “Only as the tides go out do you see who’s been swimming naked.” Right now is like the biggest transfer of wealth in history. So, you could look at it in a negative way, or you could look at, “How can I get a part of this?”

There’s a lot of baby boomers that are retiring, especially in the mobile home park space. Acquiring HVAC, I’m looking to acquire an HVAC business, as you know. We’re going to be the safe pair of hands to buy some of that for the cash flow and use the digital marketing to grow that. So we’re looking for a couple of those next year.

This is a tremendous time. This year, I literally became a minimalist… so I just focused on making sure I could keep growing businesses and start doing a land grab, and it just happened to be at the same time [as the pandemic].

I literally just launched my first e-comm store the first week of the pandemic. It was good and bad, like it was good because we got out. The bad part was, we had to return a lot of orders. We bought all this traffic on Facebook. So all these like mops, for example. It was kind of the perfect time.

All these people were freaking out because that was in the first [stage of the] pandemic. People were all about keeping stuff clean. We were selling mops like crazy and it was like, I couldn’t even sell enough mops. But the only problem is the objects come from China. So they weren’t shipping anything over… so I had to return all the orders.

Literally… it hasn’t been any impact. I speak at a university [about] digital marketing. And I’m like, what comes down to what people need, the hierarchy of needs? And the very bottom of the rung is housing, food, water, and just providing an income, basically. I wanted to make sure I was in at least a couple of those.

The writing’s been on the wall for a long time. I was in retail in the last decade, but I knew that wasn’t gonna last forever. So I got into real estate, mobile home parks, and really started focusing on digital marketing, because I knew that’s where I needed to be.

The people that positioned the last few years, they would be way better ahead. I think a lot of people, if you’re in a struggling position right now, you’ve got to make the moves now because now’s the time, because everything’s been fast forwarded five years… E-commerce has taken over. If you have a retail property as first an investor, you need to get out of that, because brick and mortar is dying. You know that, and everything’s online.

So…you could take that money and put it online and make a lot more money right away just by managing your data. Uh, and then two is just get into spaces that are going to have long-term modes.

The thing is, if you’re an entrepreneur, this is what people should take away. What is the most urgent problem you could solve today? Take action immediately and solve these problems immediately. And then you’d be in a lot better position.

I was lucky and fortunate because I saw the avenue 10 years ago. I’ve felt the pain, been positioning. Sacrificed the last five years. Nobody’s seen me for the last four years. All I do is work 100-, 120-hour weeks.

Andrew Gordon: Yeah, I think that’s really helpful. You’ve given us a lot of good advice. And one of the things that I also took away is that it seems like it’s really important to diversify and that even if your business is doing very well, and perhaps you have some cash on the side, now may be a good time—perhaps a better time than ever before—to put some of that capital to work and diversify it into different ventures.

Jonathan Tuttle: Exactly. Exactly. Yeah. I mean, right now it’s easiest with technology. You could start a business, you can get it incorporated in a week. That could be up and running and testing ads on Facebook. Get a copywriter, media buyer, build your structure, build a team, and do like a Ronald Reagan “trust, but verify” over the shoulder management. See if you have a product-market fit. If you have product-market fit, which basically means a business, you’re testing to see if the market wants what you have, niching down into a focus instead of being broad.

The people that win are gonna be the ones that are focused on one or two things, and they’re ready to become the expert moving forward.

Andrew Gordon: And Jonathan, you brought up how it can take only a week to form an LLC. You’re a client of ours and we’ve done a number of business formations for you. Is that something that you would recommend to people out there, to go to an attorney for business formation rather than doing it on your own? Or, what are some of the pitfalls that you’ve seen when people try to do certain things on their own?

Jonathan Tuttle: You want to speed and execution. Money loves speed. And expertise.

You could Google stuff online, but you still need that guidance to get you that speed and execution. At the end of the day, you have the whole complete package. You have the taxation, you’re gonna tell ’em the avenues. You’re gonna tell ’em the newest laws that aren’t going to be on Google, and not gonna be on those articles for months. You’re like, “Hey, this just came out last week.”

When you were doing like all the government loan stuff, I actually watched that and did it for my parents and got them $37,000. Thank you. [laughs]

Go to the expert and then you take it as a resource to be your trusted advisor. Expedite the process. Like I said to begin with: mentors. I hire mentors on mentors on mentors, and then test it and build a team.

With our legal structure we did, it’s for acquisition of the HVAC businesses, and it’s a complex legal structure… I was like, “Most people aren’t gonna know what this is.” It’s called an SPE, a special  purpose entity. It’s a very complex legal structure that allows you to basically buy, pretty much risk-free, buy businesses.

Obviously I recommend everyone reach out to you, because very few people do [this type of business formation]. You did an amazing job on it. You’re not gonna get that on Google. Trust me. You’re not gonna get that on Google.

And on top of that, what are you willing to risk? Time is money. Speed and execution’s money. So the longer you wait, someone like me who’s already positioned right is going to scoop it up before you. Having a team [where] you’re just like, boom, boom, boom, boom. That’s how you’re gonna win in business.

You’re also going to be able to say, “Hey, I’ve seen this doesn’t work. This works. Try this.” That’s all the game right now. That’s literally all the game.

Andrew Gordon: So Jonathan, just a couple of extra questions for you.

Jonathan Tuttle: Sure. Bring ’em. Love it.

Andrew Gordon: You’ve obviously accomplished a lot over your years, but if you were able to somehow go back in time to talk to your younger self, what advice would you give yourself for the future?

Jonathan Tuttle: Like when I first started out in my career, basically?

Andrew Gordon: Yeah, yeah.

Jonathan Tuttle: So this is a good question. So I was always tenacious… just a little backstory: When I was a little kid, my parents taught me the value of money, but the thing that I learned when I was a kid was I would literally go door to door. Maybe this is where I learned the sales skill sets.

I’d go door to door with my Red Riding little wagon, selling rocks and flowers for five or 10 cents I’d get money to get gum and candy at Walmart or wherever, back then. And when I was eight or nine, I’d go shovel and things of that nature, and sell cards door to door to get money for Nintendo and Super Nintendo games.

But going forward, the skillset… what I wish I learned was believing more in myself.

Everyone would laugh at me. Everyone laughed at me in 2007 and 2008 about mobile home parks. Now everyone’s like, “You’re so right. Now I see it in a Forbes article.” I was ahead of the curve, but I didn’t believe in myself. Now, I believe in myself. I put the work in, the education.

Andrew Gordon: Yeah, that’s great advice.

Jonathan Tuttle: Thank you.

Andrew Gordon: Well, thank you very much for being here. I think you provided a lot of really helpful advice to those out there. If someone wanted to learn more about the different projects you’re involved in, how could they find you?

Well, thanks for having me on. It was awesome. It’s exciting. But I’ve got a few different things, like I alluded to. The mobile home [fund], or my $10 million raise, is right now, so go to if you’re an accredited investor.

And then if you’re an HVAC owner… We’re only really looking for, as you know, Florida or Texas. But if there’s something in Illinois, Indiana, Wisconsin—because I know you’re right in that area—we would look at that. Keep your legacy intact, keep your employees. We’re looking to buy that immediately. 

And then, the digital agency. It’s like a growth agency.

Or just go to my Facebook, just if they want to connect me socially, Facebook. Jonathan Tuttle Official.

Andrew Gordon: Thank you again for being on.

Jonathan Tuttle: Yeah, I appreciate it. It was great. It was fun. Thank you.

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