Starting Your Own Business at 18 Years Old

This is a Contractor Radio interview (host Jim Johnson) with Tom Self about Tom's path from early entrepreneurship to owning Proliance (public adjusters and general contracting). Tom describes starting entrepreneurial activities very young (lemonade stands, flipping items on Craigslist), joining contracting work as a door-to-door salesperson, struggling the first ~2 years, persisting, then progressing from employee to partner to owner. He emphasizes learning by doing, limited early training, and a strong work ethic shaped by his parents.
Questions this video answers
About 18 years.
Worked as an employee for 7 years, partnered for 3 years, then owned Proliance for about 7–8 years.
Around 16 years old (he says "probably 16").
Chapters
Hey, everybody, it is Jim Josin here, your host with Contractor Radio, the show that helps contractors get control of their business, lead it well so that they can then grow their business and hopefully achieve their dream, which is usually to find some personal and financial freedom to do what they want with who they want, when they want. And in today's show, I have an awesome guest. I'm so excited about this guest, it's not even funny because I've gotten to know him for a long time now. He's actually been one of our clients for seven, eight years now. And I got to meet him right in the beginning, which was really cool. He took a leap of faith, and things went pretty well for him. And this is part of our Contractor Success series. We're doing the series throughout the summer so you guys, as contractors, can see what others have gone through so that you can relate a little bit to some of the struggles that you may have and then some of the things they did to overcome those obstacles and challenges and really grow their businesses and in an exponential way. Super excited for this guy. His name is Tom Self. He is the utmost most positive, hardworking client that I have ever dealt with or individual I've ever met. I'm super excited to bring on board. Welcome to the show, Tom. What's happening, brother?
Hey, how are you? Thank you so much for having me.
It's awesome to have you. So owner of Proliance, Public adjusters, and general contractors, you're in one of those odd states, Illinois, where you can do both at the same time. But, you know, things have turned out to be pretty good for you. But let's. Let's go back to the beginning. Why don't you tell us, like, how it all started for you, like, how you got in the industry and then why you started your own thing.
Totally. Yes. I've been in the industry for going on 18 years now, if you can believe it. Yeah, that's been a lot longer. I didn't even know that it's been about 18 years. Yeah. I started initially, one of my friends in high school, like, early on in high school, maybe even late in middle school, told me that they were knocking doors and they were loving what they were doing out talking to people. Like, at that time, I was on Craigslist on the free section, looking for things that I could put in my mom's garage sale, and I was flipping things on Craigslist. I was doing lemonade stands early on. So I really was always entrepreneurial, and I was working a job, I believe, at Menards, and then eventually went to Red Robins, where I was a server. I love talking to people there. But what I really wanted was what I got from the position when I showed up. Freedom of being able to, based off the results that I put in, get paid back from the actual results that I get. So that's the part that I love. So I showed up day one, fell in love with it.
The.
The crazy thing was, was that I actually sucked at it. I was, like, not good at all. So you know how I said, hey, we get paid for the results that we put in? That's what attracted. Attracted me to it. I actually didn't mind that I wasn't getting paid a lot because I didn't deserve a lot. I wasn't very good at it. But what I noticed was the more doors that I knocked, the bigger my paycheck would get. I just had to put in a lot of extra work. So I fell in love with that. I actually, after several years, became good at it because I didn't give up. I learned that from my parents. I learned that my dad, he. They are some of the. My dad and mom, they're some of the hardest workers that you would ever meet. And I think that's what has been the role model for me, you know, is, hey, I had my parents who taught me that. I also was never given money. I always had to earn it. So with those couple things, you know, I have to give the credit to my parents. They raised me really well. I worked for my employer for seven years. Eventually he was like, hey, Tom, I can't really afford to pay you more. Do you want to partner? So we partnered up for three years, and then now I've owned Proliance for seven or eight years.
Wow, that's quite the story. So you're like, hey, I think I could go do this thing. I'll knock doors. My activity that I do. If I get some results from it, I'll get paid for it. And you like the idea of it, but you weren't very good at it at the beginning. But you kind of got that whole 10,000 hours thing in, right? You did it so many times that you became good at it. How long did that take you to get good?
Yeah, so for a couple years, like, literally, I would have to pay my friends who are working at the company to put my name on some of the leads so I wouldn't get fired. Like, I was like, it really was bad. It was that bad. And I mean, it took me probably a good two Years to get to the point where I could independently do it. Like, I really, really struggled.
That's an incredible amount of persistency, discipline, that kind of. What were you doing to try and get better?
That's the thing. We didn't really. And that's, you know, jumping way ahead. That's why I'm so passionate about training people and providing a really great experience for people. Because we didn't have any training. They came in. There were people in the office who, you know, were doing the pitch. The first day that I started, you know, there'd be, like, one day of training, and then it was like, all right, go off and do your thing.
So there was.
Yeah, figure it out. So, yeah, we didn't really. And. And personally, I didn't even think about, like, the training and practicing. It just. I wasn't even aware of it. I was just like, hey, this is a job. I'm here. Like, I need to. I need to work harder. I was probably 16.
Oh, wow. Yeah. You were just a kid, so you're still living at home. So if you didn't make a whole lot of money, wasn't that big of a deal. Right, Right.
And I did other things too. Like, I was flipping things on Craigslist still. I was finding ways to. There was a crazy story. A crazy Craigslist story was there was a company that was given. They actually were trying to ship 5,000 gallons of paint to Africa. And they were like, hey, the shipping costs were too much. So they were like, we're looking for someone to take all the paint. But that's the caveat. Like, you need to take all the paint. You'll probably need a few semi trucks and 10 to 20 men. I told them that I had one friend who's on crutches and a school bus, but I will take all the paint. And they. We talked them into it. So I, I, I was. I. It's interesting because in some things, I was good at sales, so, you know that it's just real interesting. At the door, I kind of. It was like.
We gotta talk about this for a second. I love when I do all these interviews and I don't know. This is great. Somebody need to get a bunch of paint to Africa.
Yeah, they were donated.
So where did you need to get it to?
I needed to sell it. I was trying. I wanted to get it so I could sell it because I wanted to flip it. I was on the free section of Craigslist.
Oh, so you, you. And how'd that go? Did you sell the Paint.
Yeah, we did really, really well. Like, people were coming over every day just grabbing paint. I, I, I filled my parents garage, my friend's garage, like it was everywhere.
So I'm confused, though. So whoever this was was trying to get paint to Africa.
That didn't work.
That didn't work out, right?
Correct.
So now they got these 5, 000 gallons of paint that they got to get rid of. You say yes. Did you pay them a portion of what you got or just take off their hands or.
Zero? I paid them zero dollars because they were, they just wanted to get rid of it out of their warehouse. They didn't want to deal with it.
Because they weren't able to get it to Africa.
Because they weren't able to get it to Africa. Yeah, they were donating it, but they're like, oh, this is too much money to donate, so we'll just get rid of it on the free section of Craigslist. It wasn't that easy to sell because it was all mix and match. Yeah.
Oh, man, that's a heck of a story. You know, that's doing whatever it takes. That's really cool. So, you know, you go to work for a guy, you're struggling for the first two years. What clicked?
What clicked was the ability that, like, my effort and my results generated my income. And that did click initially as well, which is why I stayed for so long, because I knew that with enough practice, with enough dedication, like, I saw other people and I'm like, these other people are doing well. There's no reason I can't do well. I just have to keep persisting. So I saw the light at the end of the tunnel, and I really liked the person that I worked for. He gave me a lot of freedom, which is why I really value that there weren't people breathing over my shoulder or anything like that. And I just stuck. I stuck with them. And I saw a lot of people quitting, and that kind of motivated me. I'm like, oh, all these other people are quitting. I can do this. Like, I'm never gonna give up. So I saw the, I saw that I would be able to rise in the company and really be able to do something there with the owner of the company because of that.
So at some point, did you just gradually get good at it or was there like some kind of light bulb went off and you went, ah, I get it now. This is how I'm messing.
It was very gradual. Very gradual. Yeah. But then once I was good, like, I had a lot of confidence that I could do it. And then it was like. It was almost like. Took a long time, but once I got there, I really shot up. But it wasn't a light bulb moment. It was more of gradual to get there, but then I stayed there.
That piece, this piece, that piece. And they finally kind of all came together, started having success, and then it was just like confidence was there now, right?
Yeah. And I just talked to so many homeowners. That was always my thing. Just talk to as many people as I can, hit as many doors, work morning to night. I like, I didn't like. I valued working out, but I wouldn't work out throughout the year because I wouldn't want to spend that one hour working out when I could spend one hour. That's like. To me, that's like, who would go work out when you could spend that hour working?
Every. Every person listening to this right now is going to. I want to hire Tom. I don't get Tom to come to where I need more toms in the world.










