McConaughey (actor Matthew’s older brother) got his start working with his father in the oil fields at age 12 and made his first million dollars by age 30. Gilliam dropped out of high school to work at his father’s business, Curley’s Machine Shop, which he later ran and sold for a significant profit.
McConaughey and Gilliam say they are looking for plain-folk entrepreneurs who would benefit from a business partnership. MBA grads are also welcome, but only if they’re not too snooty to discuss the numbers over Miller Lite.
The two recently spoke with The Washington Post about the show, which is airing its Season 2 finale on Wednesday night. They also shared some of the lessons they learned when they were building their own wealth, what they look for in entrepreneurs and whether Prather is really the one calling the shots.
You both have pretty unconventional success stories. Tell me a little about how you built your own wealth.
Gilliam: I tell everybody my career began with a broom and a shovel. I started working full time in the shop after school and then I quit school right around the 10th grade. I learned by observation. I wasn’t smart. I made bad grades in school, and I really couldn’t keep my mind on anything. I started in the shop. My dad let me run the machine. I punched a timecard up until my 30s. One day my dad walked up to me and said: “I’m leaving. It’s yours. It’s up to you to run it or ruin it.”
I started taking it in a different direction. I called a friend of mine and asked about getting an exclusive license to the technology they had. He looks me straight in the eye and said, “Butch, no we won’t do that.” I was afraid I was going to ruin my daddy’s company. It was like a poker game, and if you lost it would’ve been death. He said: “No. Butch, we won’t do that. But if you’re interested in buying it, we’ll sell it.”
I wound up buying the technology for next to nothing. Our business took off after I took possession of that technology. The reason I sold it [for more than $100 million] is I was afraid I wasn’t going to be able to handle that much business.
I’m glad I worked for my money. I’m glad I didn’t just win the lottery. Because when you learn how to work for your money, then you learn what the value of it is.
McConaughey: I was very, very knowledgeable about pipe because I’d worked it all of my life. I’d been out there since I was a kid, so I knew more than the next salesman. I got into this making money. Never really had any of it to speak of before, and I just had a hell of a time.
But I looked up one day and there I am broke, and I thought to myself, “Who am I?”
I went Chapter 7 before I was 30 years old. I just got caught up in the whirlwind. Not that I was doing anything wrong. I never had much money growing up. I kind of got slapped down, and that was probably the biggest lesson I ever learned. I lost it all. I put on my Red Wing boots and had to start over.
Where did the money go? Nice cars and vacations?
McConaughey: I was just living it up. I went to Vegas 22 times in one year. I was just a young, fun kid with a bunch of money and still making it.
A lot of people that had been through depression before and were ready for it, they said: “What can we do? We know you know what you’re doing.” They put the money up, and I’d go find the deals and that basically got me started all over again.
Gilliam: Everything Rooster just got through telling you about him, you can pretty much do a 180 about me. Rooster had a lot of ambition, competence, a pretty big ego. I think he started off not afraid to make a big giant swing at it. I was pretty much the opposite. I learned through observation. I had a pretty low self-esteem. I took a lowly job at the shop, sweeping the floor. I never expected to get much further than that, to tell you the truth.
What do you look for in the people who come on the show?
Gilliam: We try to take each person. I don’t think there is a generalized set of parameters. We’ve encountered people who we thought were good people turned out not to be. Their motivation turned out to be different than what we thought. The biggest lesson I’ve learned is to invest in yourself as much as you can. The person that’s going to be your best companion in any business is yourself.
Rooster and I have a really good relationship. We know how each other think. That took time. Having partners is hard, and that’s what we try to tell folks on this show. They come in here and first thing they want to do is create a partnership. Rooster and I try to figure out if there is a way they can avoid that and just put more stock and faith into themselves.
You’ve said on the show that the person is sometimes more important than the product. How do you assess someone’s character?
Gilliam: The only thing Rooster and I go by is we spend time with people, talk to them and try to get to know them. Basically, if they remind us of us. You can pick up on that pretty quickly.
Rooster just told you he’s kind of a big gambler and willing to take chances, but he’s learned that if he wants to be successful for the long run he’s just going to have to knuckle down. Like he said, he took off his ostrich boots and put on his Red Wing boots and went to work. He dedicated himself. He was willing to invest the time and effort. If these people are willing to do that, we’ve got something to offer. If they want to get rich overnight, we don’t have anything to offer.
McConaughey: We make that statement all the time. If you want to get rich overnight, don’t come on this show.
Gilliam: We know people get rich quickly all the time. Especially in this day with these apps and the tech world that we’re living in. We know that happens, but we just don’t know how to do it. We’re kind of old-fashioned.
The product matters, but we also know that even the greatest product in the world can be trainwrecked if you’ve got a crazy person at the helm. That’s what we’re willing to avoid at all times. Look at the Titanic, Captain Smith, good guy and all that. But he did not heed any of the warnings. He had message after message after message that there was an iceberg. And what did he say? “Full speed ahead.” That’s not the kind of person we want at the helm of our ship.
So far on the show you’ve handcuffed people, taken them camping and pretended to be a blind pilot. Is it important to test a candidate in such unorthodox ways? Why?
McConaughey: It’s very important because this is a condensed version of how Butch and I do business. We’ve only got so much time to be with them. You’re not only testing their product, you’re testing to see what kind of glitches they have. Their confidence. Can they laugh at themselves?
Gilliam: If someone comes to you in an office setting that wants to throw their résumé out there and have a 30-minute discussion about who they’re going to be, you can nearly word for word recite that. If anybody’s prepared themselves, you know what they’re going to say. You know how they’re going to act. They know they’re being auditioned, but Rooster and I like to kind of catch them off guard, get them in an unconventional setting and see if we can pull anything out of them adversely without them being aware of it.
Let’s talk about how much you decide to invest and how you choose the companies. What markers do you use?
McConaughey: First of all, we want to make sure they need a partner. You may not need us. So sometimes we may go into it and when it gets triggered it may not take as much as we thought or we may find problems. We’ll start digging. If I knew everything there was to know about them, how much fun would that be on the show? How spontaneous? So there’s some vetting that goes on afterward.
Some deals don’t work out, but we have four or five that we’re still involved in.
Now that you’ve been doing this for a little while, how are your investments doing? Any unexpected big hits?
McConaughey: We’re patient people. SpeedETab is moving right along. He’s having more success in coffee shops. People in the bar are getting too drunk to go pick it up, I guess. And we’re working with the guy with the iQue Repair, trying to get him some more business. Nothing has just taken off. I mean, we’re not going public with any of them yet.
Gilliam: We’re not looking for the get-rich-quick deal. We’re truly listening to each person who comes into the clubhouse. Trying to find out what it is that they want to get out of it. Some of these people are just trying to figure out how to get a successful business, no matter how much money they make. We’re talking about just getting to make a decent living.
The show’s not about showing people how to get rich. If we can help someone or get them on the right path to success and they look up one day and they’ve made a bunch of money, great.
Do you have a particular mix of businesses overall that you want on the show, or are you just looking for good ideas?
Gilliam: We don’t want people in here who are just looking to get rich or Ivy League people who come in here and talk over our head. We want plain old everyday people to come in and talk to us about their businesses or inventions. People we can relate to.
McConaughey: We didn’t have to do this thing. They came to us and we didn’t want to do it. We put some stipulations on it. The format is just based on our lives more than anything. It’s so neat when you find out that we’re sending a message out there to wake up with a clean conscience, try to do business better.
What should the entrepreneur’s ultimate goal be if not to get rich? To be financially independent?
Gilliam: I think Rooster and I agree on this more than anything else. We’re not young people anymore. When you’re young, it’s easy to get caught up in the race of business and the fast pace of living. What we try to tell everybody is one day you’ll look up and be kind of at the end of the road and find out that if you put too much on the destination or where you’re trying to arrive, you’ll find out that you’ve wasted the journey. And that’s the real goal of your life. [It] is what have you done day-to-day throughout your life. That’s what’s most valuable to you in the end, more than a pot of gold. [To] look back on your days with fond memories and a big wealth of friends and family that respect you because you’ve done well by them along the way and helped people, that is the treasure. That’s the big reward. I know a lot of rich miserable people.
McConaughey: I’d rather have fun losing money than I would be miserable making it. Success is not just having money.
So tell the truth. Is Gil the secret sauce to your entire operation?
McConaughey: Here’s the deal with Gil now on the show. This year, Gil doesn’t have a clue who he’s picking up when he goes to that airport. Not one clue. And yet, he has not only tenderized, I think he’s shredded a few of them. There’s been some instances that I think we’ve had to give them a break before they come in. He’s shocking the hell out of them.
One thing some people may not know about the two of you is that you’re competitors. How do you make that work?
McConaughey: Butch and I do the same thing. We compete. We always have. I guess what we’re trying to tell people is we fight fair. It’s gotten to the point we’re just happy if either one of us gets the business.
We’re friendly competition and I think Butch would tell you that’s something people need to know. You can get along with your competitors and sometimes you can work hand in hand.
Gilliam: It’s pretty simple if you think about it. When you’re breeding negativity between competitors and it’s all negative, all you’re trying to do is hurt each other. How can you expect any good to come of that?
Anything I didn’t ask you about?
Gilliam: Tell your readers that the biggest crooks in the world wear nice suits and ties and very pretty dresses. Be careful. Tell them that as hard as it is to make money, it’s …
McConaughey: … even harder to hold on to it.