Today Connor and Brittany are joined by Tim Chermak, a successful business owner and former child serial entrepreneur.

Here’s a transcript of our conversation:

Connor: Hey, Brittany.

Brittany: Hey, Connor.

Connor: You and I love to talk about entrepreneurship. We do, which is a big word that like I struggle to spell, but you know, I still can’t spell it either. It’s a powerful word and it just means, you know, being your own boss, taking initiative, being a problem solver, serving other people by creating value for them. Like, these are amazing things. And what we love about it, of course, is that as you make other people’s lives better, they reward you and you make a lot of money because you’re solving these problems for them. So we share a lot of stories, of course, we have our Tuttle Twins Guide to Inspiring Entrepreneurs, which you can find at And, today we have a friend of ours, Tim Schmack, who is the founder and CEO of Platform Marketing, to join us to talk about his entrepreneurial journey and what it means for the kids listening today. Tim, thanks for joining us.

Tim: Hey guys, it’s great to be here.

Connor: So, a lot of crazy entrepreneurs like you got started when they were kids. So did you have like a lemonade stand or like what did you do as a kid that were the beginnings of your own journey into entrepreneurship later in life?

Tim: Yes, I absolutely did. I had lemonade stands. I remember one year my family had a garage sale and I convinced my grandma to bake, like, a fresh batch of chocolate chip cookies so that I could sell them. And you know, I was probably too young like at the time to realize that I’m getting my cost of goods for free. So it was pure profit cause I didn’t have to pay for the cookies, and didn’t have to pay her royalty profits on the back end. None of that. And I don’t know, I think I made $9 and I was probably, you know, five or six years old, something like that. And at that amount of time, $9 was a small fortune. You know, when you’re, when they’re yet when you’re that young, right? And the idea of strangers coming up to you and I think I was selling ’em for, I don’t know, 25 cents or 50 cents a cookie or something like that. Giving you money in exchange for a product or service you had even at a young age, that just felt magical to me. Like I was like in flow as a preschooler, right? Like this is what I’m gonna do with the rest of my life. And yeah, so I mean I had lemonade stands, I sold baseball cards to my friends, but even as like, you know, a little punk first grader, it wasn’t enough to go buy baseball cards in my own. What I would do is I would buy my own and then I would repackage some of mine just using like paper I grabbed from my mom’s printer in her office and I would repackage them and sell baseball cards to neighborhood kids at a store. And I think, you know, I sold them for whatever, like a quarter a pack. And even then I would have to,  you know, keep my customers happy, right? I’d have to put enough good cards of good players in those packs so they’d keep buying them from me. Cuz if I just filled these card packs with the worst players I had, you’d obviously get a reputation really quick as like, this is a scam, this is not a good product. So I did that. I sold golf balls, I’d go like, you know, fish golf balls out of the creek kinda that was by our house cuz we were sort of near a golf course. And then I’d set up, you know, an unlicensed and unregulated, you know, folding chair stand on the nearest green and I’d sell the, you know, cleaned-up golf balls that I had polished up. So they were, you know, at least somewhat white again to, you know, golfers coming by. And so like, I had plenty of businesses when I was young and I think if adults are looking if they’re actually looking for it, they can see the signs of entrepreneurship in some kids pretty young. It’s just that obviously the public school system and really all of society and culture conspires, I think too, you know, try to blast the creativity and the drive out of young kids to make them conform to a curriculum you know, like whatever school you’re going to, frankly, whether it’s public or private. But I think if you’re looking in certain kids you can spot entrepreneurship, pretty early.

Brittany: You know, it’s funny you reminded me of a story in sixth grade. They had all of us, start our own business and I made shakes with like candy bar mix-ins and at the end of the whole project, our principal came in and said, kids shouldn’t be earning this kind of money. And they decided we didn’t get to keep it. They took the money from us, from all of us. And that like, that really stuck me. So I’m like, wait a second, what? Yeah, they put it to a class trip to something like a boring museum. So anyway, I like that you said that adults aren’t always looking and seeing that this sparks, you know, this entrepreneurial spirit in kids. But what sparked this in you? Did your family really support this? Did you come from an entrepreneurial background?

Tim: Yeah, you know, I mean, to be totally honest, I think I was probably born with that drive. You know, I don’t know if it’s in genetics, nature, nurture, you know, we could have a huge long discussion about that. But from a very young age, as far back as I can remember, I loved the thrill of like selling something to someone and packaging up something that they might want to buy. My family was also very entrepreneurial though. So there’s definitely, an element to play where I saw it as normal that my dad was a small business owner. My mom and dad started businesses together. Actually, my aunts and uncles on both sides of the family we’re all small business owners, as well. So as far back as we can go, actually multiple generations of all the males in my family, like even going back to Europe when they, I mean they’ve all been entrepreneurs. Like there’s been no person in my family who’s the breadwinner on either the paternal or maternal side that’s ever had a W2 paycheck for a living.

Connor: Let me ask a follow-up question about that because I, feel like there are some people who are just wired to be an, and I think there are other people who can be entrepreneurial or who can kind of learn the ropes and try and apply themselves who maybe aren’t naturally that way, but they can, you know, grow to think that way they can learn from yep. Successful entrepreneurs about what they do and they can mimic that behavior and make it their own. So, you know, you have the benefit of this lineage of entrepreneurs for the young kids listening out there who maybe, you know, don’t have that flow from preschool like you did, but who want to, you know, make money, who want to be their own boss someday, who might have a creative business idea or they want to,  you know, be a problem solver and they want to find these entrepreneurial opportunities.

Tim: Fancy French words.

Connor: What would you suggest for the kids listening, what are ways that kids, as you reflect back on your life, what are things that kids could be doing or thinking or what would you suggest for them if they want to kind of grow into this type of entrepreneurship?

Tim: Well, the first thing I would say is that you don’t really learn how to be an entrepreneur or learn how to think entrepreneur. I honestly think you have to relearn it because I think all kids are more entrepreneurial and more creative than we give them credit for. And a lot of kids have that creativity and that, you know, business drive squelched out of them by how boring school is, you know? So I think it’s more about relearning than learning, as a young kid, take any opportunity that you can get to sell things to people who need it. You know, very often you can find an entrepreneurial opportunity just by thinking, hey, when someone needs something in a certain situation, can I put myself there right at the moment they might wanna buy it? Like if there’s an event going on in your town and it’s really hot outside, right? That’s when selling ice-cold bottles of water might be a great business. If you’re a young kid, you know, go buy a bunch of bottles of water and they’re a quarter a piece or 50 cents a piece and sell ’em for a dollar, you know, that’s like a keystone two to one markup, right? Same thing with, you know, my first business selling chocolate chip cookies at a garage sale. Like when people are perusing for our family’s stuff that, you know, we don’t want or need anymore. Yeah. It might be nice to munch on a fresh chocolate chip cookie, right? You have a captive audience, in those situations. I had a golf ball stand I mentioned where I would sell golf balls to golfers and it was on, happened to be on the ninth, tee box and so they’ve maybe lost a couple of golf balls to get up to that point, right? So it, you know, yeah, they might be willing to buy one of my golf balls for a dollar that I got for free cuz I found it in the creek. You know? So just always be willing to sell something and get market feedback and it’s okay if it doesn’t work right away cuz you’ll figure out what does work. You know, I think that’s what keeps a lot of people from trying is they’re so afraid that what if it doesn’t work? What if it’s not the right location? What if I don’t have the right product or service? Like what almost what defines an entrepreneur is that you do it anyways and you just figure it out and fake it as you go along. I mean, even as an adult, I’m 30 years old now and I still every day wake up feeling like I have no idea what I’m doing and you just learn every day and you, you, you run experiments and you iterate and you just figure it out as you go along. You know, like adults are basically just kids with a few years of additional experience. There’s not a whole lot of distinction in the human mind, I feel like between a seven-year-old and a 27-year-old.

Brittany: You bring up a good point and I wanna kind of have you expand on it. You said some things don’t always work. What is the greatest lesson you’ve learned from failure? I know Carter and I like to talk to our audience a lot about failure. Being reframed is a good thing. So is there a particular instance you remember where you failed or something didn’t work out but you took, a really important lesson from it?

Tim: Yes. And I don’t want to talk about it, but I will just for you guys.

Connor: A failures, plural.

Tim: A couple of years ago we were having a certain degree of success in our marketing company and we thought, well, we’re doing a really great job working with folks in the real estate industry. What if we expanded into other industries? And we did that and I hired kind of ahead of demand like I went out and hired additional employees just assuming that we’d be able to grow these new business divisions and that’s not what happened. So I basically increased our fixed costs. I hired salespeople, I hired more employees on the backend, just assuming that new work was gonna come in. And it’s not how it happened. It was much more difficult than we thought it was going to be. And a couple of the people that I hired were very, very good friends of mine, basically best friends from childhood. And I had to like to lay off one of my best friends cuz I was like, Hey, this is not working out. Like we can’t keep paying you because the revenue just isn’t there to cover your, you know, your salary. And it was devastating to me and obviously devastating to him too because like obviously losing your job sucks. And that probably emotionally scars me to this day. That was probably the worst day of my life that I had to call up. I think we had to let three people go that day. So it was like back to back just gut-wrenching phone calls of I’m so sorry I have to lay you off. And none of them were because of poor performance or they weren’t doing their job. It was 100% my fault that I hired people earlier than I should have. And it was a pure leadership mistake again like they didn’t do anything wrong and I had to inform them that, you know,  they couldn’t work with the platform anymore and that was awful. And I probably still have elements of like PTSD, thinking about it to this day that like, why was I such an idiot and I hired too soon? You know? And then there’s all sorts of other like entrepreneurial life lessons. You learn about hiring too late too. There’s people who might tell stories of, oh I should have hired way sooner. And so that’s the paradox of entrepreneurship is figuring out every situation is different cuz there’s really not bulletproof rules you can follow if here’s when to hire, here’s not when to hire, here’s when to expand your team, or here’s when to, you know, shrink your team and get more efficient. It’s all just learning as you go. But that was definitely a huge failure cause I had to lay off some of my literal best friends from childhood.

Connor: So Tim, what I’m hearing from you is that the young people listening can’t really learn entrepreneurship at school or in a textbook or maybe even listening to this podcast or others like it sounds to me like your advice is that entrepreneurship is an experience that you have to go through and you have to learn your own lessons, experience your own failures and learn from your own mistakes. Do you feel that’s kind of the general rule that you’re pitching?

Tim: Yes, that is, absolutely true, Connor. I think it’s actually the opposite of what most people think happens. You know, learning is what happens when you’re out in the real world getting real-world experience, running an actual business, and making actual real-world life decisions. Learning is what happens in the real world. Inspiration is what happens when you listen to podcasts and read books. But you can’t learn entrepreneurship in a classroom any more than you can learn to ride a bike by listening to a podcast about riding bikes.

Brittany: I think that’s a great point and I think that’s one, you know, that we make here often because a lot of our audience is homeschooled. So last question before we wrap up. I wanna know, you know, what would you tell seven-year-old Tim is sitting there and he’s running a business, what would you tell him his life was gonna be like? What, advice would you give him or would you not give him any advice? Do you think everything turned out the way it was supposed to and by all this failure you learned?

Tim: If I could tell seven-year-old Tim, so this is back in 1998, I would say save up for when Bitcoin comes out and buy all of it when you can. And honestly I would also just, I would tell ’em to keep expenses low, run lots of experiments, you know, go out and live your life. Cuz as I look back, I honestly don’t have a lot of regrets. I think I made the right decisions when I made them with the information that I had, but I don’t think a lot of people can say that. Looking back, I think a lot of people do have a lot of regrets. I really don’t, honestly, because at most stages of my life, I went with my gut, I went with my intuition when I felt it was time to, you know, drop out of college to pursue launching a business, I did that. That’s not the right decision for everyone of course. But for me it was, you know, when I decided to hire my first employee, I didn’t have the money. I put it on credit cards, I did that. You know, as we’ve grown our business, I continually just kind of listen to my gut and, you know, let my intuition lead me. And it’s worked out. You know, and in one way or another that’s every entrepreneurial story is a guy or a girl listening to their gut feeling and just kind of going with it. Cuz so often that gut feeling is right. So if I could go back, I, really wouldn’t change a whole lot. I would just continue listening to what my gut tells me. And as an adult, it’s probably even harder cuz you get more jaded and cynical about the world and you get kind of trenched into the way you’re doing things. So it’s almost harder now that it’s talking to 30-year-old Tim and trying to convince 30-year-old Tim, Hey man, it’s okay. Listen, listen to your gut. It’s, worth following that intuition.

Connor: One thing I’ve found interesting about entrepreneurs is they seem to like appreciate the hard times, the challenges and the failures to hear someone like you who’s had failures to say, I wouldn’t change anything. I think I made, you know, the decisions I needed to or it all turned out okay etcetera. I think shows that you kind of appreciate and understand that entrepreneurship is this up-and-down journey. I’m reminded of that quote from Thomas Jefferson where he says that timid men preferred the calm of Despotism to the Tempest Sea of Liberty. You know, freedom is tempestuous, it’s chaotic, it’s unpredictable. You know, maybe the equivalent here is the, what was the, let’s say tempest Sea of liberty. Oh, the calm of Despotism. I was trying to remember the other side. The calm of having a W2 paycheck, right? Having a steady paycheck. It’s predictable, it’s easy. We, all like that comfort. But going for that ride is where you can create a ton of value. It’s where you can make a lot of money. It’s where you can impact a lot of people’s lives too. And, I really like what you said, my takeaway, Tim, from what you’ve shared today, especially thinking about the young kids listening is, you know, find something to sell someone at the time they need it. I think of, you know, the 4th of July parade or whatever, when people are hot and they’re walking around and having the kid with a little, you know, cooler on a wagon, going around selling, you know, water bottles for a dollar and you’re like, oh, thank you. Give me one. Right? Like, that’s perfect timing for what people need. The more you can think of those opportunities, you know, the better you are going to develop your kind of entrepreneurial skills. And then, you know, kids listening, when you turn 30, you can look back like Tim and say, you know, I have no regrets. Everything was fun. Everything, you know, factored into who I became and I needed to learn all of it. I think that’s a life worth living. And, that’s why entrepreneur entrepreneurship, I keep failing. Is so fun. So, Tim Charac, founder and CEO o of platform marketing entrepreneur extraordinaire for the parents. You can find ’em on Facebook. He’s always got a bunch of fun entrepreneurial hot takes.

Brittany: Hot takes, yep.

Connor: Yeah. Yeah. Spicy, ones too. Tim, thanks for joining us. That was a fun conversation.

Tim: Cool. Thanks, guys.

Brittany: It’s good to have Tim on. I actually just got to hang out with him in South Dakota, so that was a lot of fun. We ate a lot of fried foods, which is one of my favorite things to do. So always good to hear from him. And again, follow him on, social media. He’s always got some funny things to say.

Connor: Speaking of entrepreneurship, man, fry, anything, anything you self-fried, people will buy it. So, I had, Oreos that they did.

Brittany: Yes fried or Mm, yep.

Connor: Oh, fried Oreos were amazing. It was so weird. But anyways, entrepreneurs are coming up with all kinds of crazy things. That’s what’s fun about it. Brittany great as always, for chatting. Thanks for the parents listening out there. Make sure you are subscribed. And until next time, Brittany, we’ll talk to you later.

Brittany: Talk to you later.