How This TV Producer Escaped The Rat Race With Joe DelGrosso | 638

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Many people are searching for ways to escape the rat race. They want to retire early, enjoy their hobbies, and live a life of leisure. One popular option is real estate investing. When done right, you can retire much sooner than you ever thought possible. In this episode, Joe DelGrosso of Southern Son’s Properties sits with Chris Miles to share his journey to becoming financially independent. Knowing that the TV industry is a young man’s game, Joe looked for different ways to achieve financial freedom before retirement, and he believes that traditional investment is not the way to do it. Tune in to know more about Joe’s story and how rental income has helped him overcome adversity and support his family while unable to work.

Chris Miles Bio:

Chris Miles, the “Cash Flow Expert,” is a leading authority on how to quickly free up and create cash flow for thousands of his clients, entrepreneurs, and others internationally! He’s an author, speaker, and radio host featured in US News, CNN Money, Bankrate, and Entrepreneur on Fire, and he has spoken to thousands getting them fast financial results.

Watch the episode here

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How This TV Producer Escaped The Rat Race With Joe DelGrosso

I’m so blessed and grateful to be here. I appreciate you reading and the fact that you have been sharing it and reading, even present company included. I appreciate all the things that you do as readers to make this ripple effect real. Thank you so much for being here. As a reminder, you can always look for more information on You can always get more stuff there. We even got a playlist on infinite banking. We have playlists on different things of different clients and what they’ve done. Feel free to check out some of that new material now.

I’ve got a special guest here. He’s someone that reached out to me. I thought it was interesting because often, I don’t get people to reach out randomly. I get a lot of people who will pitch me typical guests, but Joe is like, “I’ve been following you for several years. I want to share my story.” He’s got a cool story about how he’s created a journey to financial freedom, even to the point where he was in Hollywood working as a producer for Netflix, HGTV, and things like that.

That in and of itself is pretty interesting, but it’s the fact that he’s moved into doing real estate, became financially independent, and now is doing things with short-term rentals out in the Southeast. I want to bring Joe here to talk about his experience and journey so you guys can learn from it too. Joe, welcome back to this show, but now you’re the one being interviewed versus the one reading.

Chris, this is great. I’ve been reading for several years now. I’m excited to chat with you and tell my story.

Gives us more background than what I gave to the audience here.

I’m originally from Boston. I’ve been working in TV now for many years. I moved out to California in 2011 and worked out in LA for a little while. That scene wasn’t quite the one for me, so I ended up moving out to Knoxville, Tennessee, in 2012. Surprisingly, there’s a huge TV community here in Knoxville HGTV. This is where they’re based in their headquarters. I worked for a production company here and have been doing TV ever since.

You had to make a pretty drastic shift, especially as things started moving and streaming, didn’t you?

The streaming wars hit. It was good for the Dwayne The Rock Johnson and Kevin Hart’s of the world where the streaming giants wanted those big names, but it was a little bit harder for the smaller guys.

What was that decision for you? What got you to say, “I got to do something different?” What was that catalyst for you?

You have those different moments in your life where you have a gut check. Others call it a pocket check. Click To Tweet

It even started a little bit more before the streaming wars started. In 2016, my wife and I got married. We were both making great money. We were both doing well here in Knoxville, but we were following the traditional investing path, the 401(k), and the company benefits. We were just looking at it. We’re like, “This doesn’t seem right.” I know from a TV industry standpoint that I did not want to do this until I was 65. I couldn’t do this until I was 65 because there are some ages I’m in this industry where by 45, 50, or 55, you start getting pushed out. I was lucky enough. I started when I was fifteen years old, and I was able to see that young. I was like, “This is a young man’s game.”

We knew that, so in 2016, we were like, “We got to do something different. This traditional investing path is not right for us.” I’d seen my parents invest in real estate. They were both teachers and were able to give us this amazing life on a teacher’s salary because they invested in real estate. That was back in Boston. That was more of an equity play than a cashflow game. I saw that, so from 2016 through 2019, we started buying single-family homes.

It was great, but we weren’t running it like a business. We didn’t know what the heck we were doing. We bought one property a year from 2016 to 2019 and had no idea what we were doing. We never heard of cashflow. We never heard the term generational wealth. We knew we were supposed to do it because it was different from the traditional path and was a good thing. 2019 was when we had our big a-ha moment.

In 2019, I was doing a pitchtape with a guy here in Knoxville. He owned a ton of multifamily. I was driving along with him. We were recording, and he started throwing out terms like generational wealth, cashflow and financial freedom. I had owned three properties at that time and had never heard those terms. Whenever we had spare money from the three properties, we were like, “Vacation money. Let’s use it.” We weren’t running it right. We weren’t raising rents. It was just a thing we knew we should do. In 2019, when he said like, “You need to start listening to podcasts. You need to start reading books,” that’s where it kicked off.

I read Rich Dad Poor Dad. I jumped on the BiggerPockets community, and everything was a whole a-ha moment like, “I can’t believe this world exists. You can retire before 65. I don’t have to work until I can’t move anymore.” It was such a mind-blowing experience when you entered that world of this new education. It was great. From 2019 to 2020, we bought 4 properties in 1 year. We went from buying 1 property a year to buying 4 in 1 year. We started running it like a business. We were raising rents. We’re accessing the equity in the properties. We started rolling with it.

Out of curiosity, who is the investor that sparked that in you? Is it someone that we know by chance?

He’s a great guy. It’s Jake Stenziano with Rand Property. I was doing a pitchtape on him, and he’s a super energetic, charismatic guy. The pitchtape didn’t go anywhere, but it changed my life just driving with him. I was like, “My gosh.”

If anything, that pitch tape was for you, wasn’t it?

Yes. I was just sitting there. I was blown away. I was like, “Here I am. I think I’m a savvy investor. I own three properties, but I had no idea what I was doing.” 2019 to 2020 was a big year for us. We bought those four properties. We were rolling the cashflow. It was seven properties. We were averaging a cashflow of $500 per door, which is great. Knoxville is a great cashflow market. We were going pretty well. 2021 was a really good year. You have those moments where it’s called a gut check. There are different moments in your life where you have to gut check. I like to call it a pocket check.

MORI 638 | Escaping The Rat Race
Escaping The Rat Race: The traditional investing path is just not right. We have to do something different.

In 2021, we were still rolling. We were both doing our W-2s, but the TV industry was all over the place. In the streaming wars, you never knew what was going to get picked up and what wasn’t. It’s so hard to go from season 1 of a show to season 2 because there’s so much competition now. There’s no such thing as appointment television anymore unless you’re in the NFL. It’s hard. In 2021, we were hitting a wall at the company I was at. I was like, “I’m okay. I own seven properties.” Our wealth and net worth were great, but the cashflow still wasn’t there.

We couldn’t retire. It was good, but these long-term rentals aren’t going to give us financial freedom anytime soon. If we did long-term rentals, we were going to be golden. It was going to allow us to retire probably 15 to 20 years earlier than we normally would have. Long-term rentals are tried and true, but it’s a slower game. We had our pocket check where we’re like, “We’re getting somewhere. We’re doing well but still not close to financial freedom.”

That’s when all of a sudden, the short-term rentals came in. We had one in Livingston, Tennessee. We’re going to visit family. We were like, “We can do this. No, we can’t. Yes, we can. No, we can’t.” We don’t have the patience to deal with short-term rental guests. It was such an Imposter syndrome, like, “We can’t do this and try to get over it.” We just jumped in. We said, “We got to do something here.” We don’t want to wait another ten years to retire. We want to retire by our late 30s. It’s like, “How can we speed this up? How can we try to retire by our late 30s?”

We dove in and bought a cabin in Gatlinburg in the summer of 2021. Our mind was blown. We were like, “My gosh.” It’s such a vehicle of cashflow. One cabin is triple the cashflow of a long-term rental. It’s not like what it was a few years ago. There are so many systems and automation in place. I could have never run a short-term rental years ago. It’s having to handle over keys or constantly dealing with phone calls with guests. There’s so much automation now that is streamlined. It was June or July of 2021 when we bought our first short-term rental. It was great. That got us to our level one financial freedom.

When you say level one, what do you refer to?

Other people have referred to level one financial freedom when all your costs are covered. Our monthly budget and spending are all covered by profits from the property.

That’s how I distinguish between financial independence versus financial freedom, which is that level two.

That one cabin got us to that level one financial freedom. In October 2021, I quit my job.

Congratulations. That’s great.

Don't say no too quickly. Do due diligence on everything. Click To Tweet

It is ironic because the industry is so toxic that’s why we were even pursuing this anyway. The irony was I was with a company I loved, but at the same time, it was like, “We’re ready.” Now, I do some freelance TV here and there because I still love the industry and the contacts, but we’re hyper-focused on property.

I want to go back a little bit to bridge this whole journey gap. You mentioned that it was the a-ha to you that the 401(k) wasn’t the answer, going the traditional path. I find that fascinating. When you look back, you started working when you were fifteen, but for most people that are around your age or even a younger, their entire working career when they were saving, the market was always up. It was infallible. How did you see that so quickly?

You get your statements, review them, and project out. It’s always calculating what your monthly payment will be when you’re older from the 401(k). I saw that and was like, “This isn’t good enough.” I saw the age I’d have to get to and was like, “That’s not good enough. There’s no way I will last in this industry until my late 50s or 60s. We got to try something different. We’ve got to do something different.” Here we are. I started super early in my career and got to a high level a lot earlier than most because I started so young. I’m like, “I can’t go any further in my industry. I’m at the best of where I can be.” I am seeing it from the top, and I’m like, “Retiring in my 60s and 50s is not what I want.”

Tell us this. What’s some advice you would give to our readers here? You have been reading forever. What would be the advice you would give based on the experiences you’ve had?

My biggest mistake has been saying no too quickly. Here I am in Knoxville, Tennessee, and one of the most visited short-term rental markets is right down the street from me in Gatlinburg. I know that I heard different stuff about like, “You should get into it,” and I was like, “No, we’re doing safe, tried and true long-term rentals,” which I still love, but I could have bought the property I ended up buying in 2021 for probably $200,000 less if I did it a year before. Don’t say no too quickly. Do due diligence on everything. I did due diligence on multifamily. I went through the whole thing. I took people out to coffee. I educated myself and realized that’s not what I wanted, so I moved on to the next thing. That’s what I would say to people. Dive in.

We bought another short-term rental at the end of 2021 in Blue Ridge, Georgia. Here’s the end of my story where we bought that other short-term rental. At the beginning of 2022, we had another pocket check. I was diagnosed with Chiari malformation Type 1 in the brain. It’s a super long story. It’s something that involves brain surgery, skull surgery, and spine surgery. It’s a super scary surgery. It’s a long story there. I ended up having to have brain surgery in February 2022. That’s another pocket check moment. They told me I could not do any work for eight weeks. It’s an expensive thing.

I had to go out to Colorado. That was a big, another pocket check moment but a good pocket check moment. We had a lot of worries leading up to surgery like that, but none of it was about money. That is something where I’m so thankful to real estate because we got twin boys, and my wife is pregnant. I was terrified. I was like, “I’m about to have brain surgery, but I knew if anything ever did happen to me, they were taken care of. If I needed longer to recover, we’re okay because of properties.” That’s something that I am super thankful for.

It’s good that part of your regret was the opportunity cost of not acting sooner, but at the same time, at least you acted. It was at the right time too, because you don’t have that worry as a result. You could say, “I’m going to have to deal with this. We’re going to get through it.” By the way, you look great after surgery. You’d never noticed the difference. You visually see a difference, but the truth is you seem very coherent and look great.

It was a brain surgery that affected headaches and dizziness. It has nothing to do with the other side of it. I’m a couple of weeks post-brain surgery, which is so weird to say. I was so eager to get back moving and grooving. I jumped on a Magnolia show to help them out for a little bit. I feel great. I got more energy and no more headaches. It was a good experience.

MORI 638 | Escaping The Rat Race
Escaping The Rat Race: If we just did long-term rentals, it would allow us to retire probably 15 to 20 years earlier than we usually would.

I appreciate having on. I know you have a partnership opportunity that’s available for short-term rentals. Can you explain that quickly?

We’ve taken the short-term rental stuff to the next level. We have our Instagram page where people follow us. That’s @SouthernSonsProperties on Instagram. We’re also starting to work with partners in different states like California and New York who want to get into the short-term rental market that’s so prominent in the Southeast where we are. We have Gatlinburg, North Carolina, and Blue Ridge, Georgia. We’re starting to reach out to people, looking to partner with folks and help them get into this game. We understand the automation. We know the cleaners, the handyman, and the different people that make this so streamlined in all those markets. We’re starting to have those conversations and starting to bring it up to that next level.

As you said, you have Instagram handle. Is there any other way they can contact you?

That’s the best way. DM us. Holler at us that way. We can share our experiences and story and talk to them about them. The long-term rentals are not very interactive. The first of the month is a great day, but the short-term rentals are so much fun. You’re getting pinged every week with new guests coming in. It’s so weird. We’ll go 5, 6, or 7 guests in a row without even having any interaction with them and even knowing people are there except for the ring camera ping. It’s amazing what the automation and the systems do for you. We have two short-term rental cabins, and we probably spend cumulatively 30 minutes to 60 minutes a week working on them. It’s amazing.

Joe, I appreciate your time. It’s been awesome and such a great and fantastic story. There are so many lessons to learn here. Take a lesson from Joe. You know that if the change has to be made, then the change has to be made. You got to take those little pocket checks and act on those things. What changes your life is when you do something different. I hope you make it a one-for-one prosperous week. We’ll see you next episode.

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