The Most Common Mistakes Entrepreneurs Make and How to Avoid Them

This is a written Transcription for the Midwest Mindset episode: What Does an Entrepreneur Do?

How to be a better entrepaneur and leader

Full Written Transcript of The Episode

What Does an Entrepreneur Do?

Matt: What does an entrepreneur do? Most entrepreneurs have no idea. Most likely. In fact, I couldn’t even spell entrepreneur until . Today we’re going to break down what an entrepreneur does and the biggest mistakes that entrepreneurs make so that you don’t have to make them to.

Hello and welcome back to Midwest Mindset, the podcast that makes marketing easy to understand and simple to do.

I’m Matt Tompkins of Two Brothers Creative, where we believe that every business deserves affordable and effective marketing. You give us 30 minutes, we give you 30 days of content, check it out at the content and now would like to introduce the other brother.

Who’s that? His name is Benjamin. Michael. That’s. That’s Ben’s real name.

Ben: That’s my middle giving away. Why don’t you just give everyone my Social Security number while you’re at it? Do you have two names?

Matt: 05062193.

Ben: That’s not it. Got one number wrong.

Matt: I know it was my. I gave away meriden’s. He’s he’s screwed now. He does not have an identity.

Austin: Probably not even his real one.

Matt: Probably not. Yeah. He’s like a CIA spy. I’m pretty sure our producer, Myron. But Ben, Michael Tompkins, Mike Tompkins. Mike, can I call you Mike?

Ben: No.

Matt: Okay. Mike. Mike Tompkins and I’ll be Wayne, because that’s my middle name, Wayne Tompkins. Okay. Mike and Wayne. Wayne and Mike.

All right, why don’t you introduce everybody? Because I feel like you’re working on all these these jokes in this, like, stand up comedy.

I feel like Austin Anderson here, he’s a stand up comedian. I really want to see if your material holds up. So, Ben, I’m putting you on the spot. Introduce the rest of us.

Ben: Don’t have any jokes. I’ve never done stand up in my life, but. Okay, well, in run on the board back there, we got the one and only Myron McHugh mired in McHugh.

He looks like the kind of guy who apologizes during sex a lot. Oh he does, he does that. He does it. Then we sitting.

Matt: I think I think he does. He apologizes before too. Like very.

Ben: Preemptively. Sorry.

Austin: This is going to happen to you.

Matt: I’m so sorry.

Ben: Sitting to my right, we’ve got the one and only Austin Anderson.

The new, new addition to the crew. Austin, you look like the kind of guy who has a closet full of overalls. Oh, is that true? Am I anywhere near.

Austin: I have one pair.

Ben: One pair of overalls? Yeah. Okay. Well, I’m gonna be honest.

Matt: Austin Anderson has one of the most unique approaches to style I think I’ve seen in a while.

Because, like, today, he’s got. It’s like a it’s like a Miami Vice meets biker meets Midwestern Idaho cowboy, you know, retiree, like. Yeah, it’s kind of what it is.

Austin: And I bought these jeans at the goodwill when my wife forced me to go there on Sunday.

Matt: Oh, nice. I feel like the shirt like from the waist up. It’s like I’m an Idaho potato farmer who retired early, invested well in bitcoin.

And then the boots are like, I’m a biker. Like, I rode here on my Harley, but then the hair, it’s just like full of Miami Vice action. So well done is what I’m saying.

Ben: Well done, well done. And then to my left we have the owner of two brothers.

Matt: Creative shit. Don’t let people know that.

Ben: The the one who started it all. The kind of guy who looked like the kind of guy.

Speaking of potatoes, you look like the kind of guy who eats a lot of potatoes with nothing else on him. Just whole potatoes like you eat them like an apple.

Matt: Oh, wow.

Ben: Yeah, that’s that’s the kind of guy you look like.

Matt: Yeah. Okay. I mean, I can see how I look like that guy. I do eat a lot of potatoes, though. Mashed potatoes, baked potatoes. I don’t eat them raw. Side note my head. When I shave it, it looks like a lumpy potato. So maybe you’re.

Ben: Turning into a potato?

Matt: I’m probably. Yeah. I remember in high school, they, they, we did like Mohawks. And then we shaved our heads and everybody thought I had, like, some really bad disease for like 3 or 4 weeks, like, oh my gosh, son, you shouldn’t be out at the Walmart. You should be home resting.

So today we’re talking about what does an entrepreneur do. And if you don’t know what an entrepreneur is, well, you’re not alone. I don’t know if this is actually defined for people who get into business. People like to say I’m an entrepreneur, entrepreneurial ship, entrepreneurial ism. It’s it rolls off the tongue.

But what is an entrepreneur and what does an entrepreneur actually do? And we’re going to dive into the top nine mistakes that entrepreneurs most often make, so that hopefully you don’t have to make them too. So I want to hear from you guys, though.

What does an entrepreneur do? When I say entrepreneur? It’s like, hey Bob, you’re Bobby’s an entrepreneur now. What’s Bob the entrepreneur doing?

Ben: Ben I think Bob doesn’t have a job. That’s what I normally. That’s what I used to think before I started working here, when someone’s like, oh, I’m an entrepreneur. It’s like somebody saying, I’m a life coach. It’s not. It’s like, okay, well, you probably you probably don’t have a job.

Matt: You don’t have to get a license, probably certified or.

Ben: Probably made a lot of bad investments. Oh, so.

Austin: You didn’t go to college, right?

Matt: An entrepreneur is really just you have a job that you can’t get fired from. That’s really all it is.

Ben: But now that I’ve, I know and I’ve met many entrepreneurs, the first thing I think of is if you’re a successful entrepreneur, just hard working, driven, um, business minded thinker.

Matt: Business minded thinker. That was my high school band. Yeah, actually, um, it’s interesting though, because all those things you mentioned. The hard worker.

The long hours. We think of those first, but those are not. At all related or connected to what defines a successful entrepreneur.

You know, we’ve mentioned like 51% of all businesses fail in their first 3 to 5 years. Only 6% will ever reach $1 million a year in recurring or gross revenue for a year. Which are some staggering stats.

Austin: I was blown away to hear that everybody works hard.

Matt: Not everybody. I mean, like our cousin Adam, he’s pretty lazy. He’s pretty lazy. He’s doing.

Ben: His thing.

Matt: He’s just chilling. He’s just chilling out in California. But the hard work isn’t enough to do it. So, Austin, for you, what does an entrepreneur. What defines an entrepreneur?

Austin: Someone who is trying to get people to give them money and then crying.

Matt: So like a like a carney, I think is what you’re describing.

Austin: Yeah, I think it’s a I don’t know, there’s there’s the freedom aspect of it, you know, kind of like a free spirit or a free, free bird. Yeah.

Where you’re like, all right, I’m going to do this. Like, you have a vision and, and, you know, maybe you’ve worked at other places and didn’t quite fit and you’re like, no, I’m going to go out. I’m going to do this my own. I see it working a better way.

Ben: I think that was beautiful.

Matt: That was. Yeah, that was like poetry. I kind of lost my train of thought. I think entrepreneurs, this isn’t a mistake on our list, but I would say I would define it as what I most commonly see. Entrepreneurs try to be everything, everywhere, all at once. They try and micromanage.

They’re too emotionally involved in every single decision, and I think that’s a big contributing factor why people work really, really hard and long hours.

But most businesses don’t succeed, you know, most of them fail. And so most entrepreneurs are actually solopreneurs. It’s like a I don’t know what the statistic is like. 80 or 90% of the entrepreneurs in the United States are solopreneurs.

So it’s just them just solo. And, you know, you look at like real estate agents that talk about a self-proclaimed solopreneur, the average salary of a real estate agent, though, is like 17 grand a year and the age is 60. It’s 65% women. So we have these like misconceptions of what is an entrepreneur?

What do they do? And we see entrepreneurs make these mistakes left and right. I think when I looked this up on the Google, I don’t know if you’ve heard of this thing. I think that’s how you say it. Google the Google, it’s either that or it was my my face or face space.

One of those my grandma was telling me about. So here’s the list of like typical responsibilities for an entrepreneur. Planning and directing daily operations. Having new ideas. Yeah, I mean.

Ben: I can do that.

Matt: Yeah, yeah. Ben does that every day.

Austin: Like the second one. The first one is, I think, difficult for a lot of people managing conflicts.

Matt: Learning supervision, sales and marketing or overseeing supervision, sales and marketing. So your your entrepreneur though because there’s different roles you have like your like your visionary integrator depending on if your iOS or what, what operating system you’re looking at, you have I think they call it an orchestrator or a what’s the conductor? Maestro. A maestro. There you go.

Austin: An opus, I.

Matt: Think an entrepreneur, though you have to be first and foremost. You have to be willing to eat crow. Not literally, but like, you have to be humble to be able to recognize your own flaws.

Yeah. I mean, would you agree? Like that is a commonality we see with a lot of entrepreneurs and why a lot of entrepreneurs struggle is because they don’t want to face reality or the truth and think, okay, you know what? I need to hire somebody who’s better at this than me and let them take the lead on this.

Austin: You got to do some intro introspection and do some. Be self-aware, just like what you’re good at.

Matt: And what did you take mushrooms before this? I feel like you’re very chill and wise today. All of a sudden.

Austin: I think it’s just towards the end of the day. Yeah.

Ben: Like like really mellowed out. I think any in any profession, being able to take criticism and feedback and learn and grow and not let it break you down, having a thick skin, you’re going to succeed.

And that’s what entrepreneurs have to do. I mean, you fail probably more than the average person in most jobs, but not being being able to get back up and keep going and build from that is is huge. But that that applies to any profession or anything in life really.

Matt: It’s just on a different scale with when you when you own a business or you’re on your own.

If you’re a solopreneur or you have employees, it is a different scale or different level of just pure terror that you have to compartmentalize on a consistent you know, hour by hour, daily basis. Yeah, you’re.

Austin: Right about that because you really do. Like if you’re like, oh, I got all these expenses I have to pay coming up, but where is the money going to come?

Like, you have to put that in a box somewhere in your mind. Otherwise you will you will not sleep. You’ll just be in a constant state of panic. You got to be like, all right, it’s going to come.

But I’m going to put this in my mind where I can’t think about it.

Matt: It’s kind of like how syphilis killed Al Capone, right? I mean, we all know this story very well, right?

Ben: See this?

Matt: So Al Capone had had this approach to when he was told he has syphilis, right. And it will kill you or it’ll eat away your brain. Right. Slowly. Or maybe it was chlamydia. It was one of those bad syphilis. It was syphilis. Okay. Right.

Austin: That it wasn’t a bullet that would kill him, but his own dick.

Matt: So Al Capone was just in denial. So he’s in prison, and they’re like, hey, we want to give you treatment. We want to give you penicillin for the syphilis you have that’s going to likely kill you. And he’s like, nope, not going to think about it. Not going not going to think about it.

There’s nothing to see here. And he just was like, you know, deaf, blind, ignorant. He intentionally where he’s like, I’m not even going to pretend like what they’re telling me is actually happening.

And I feel like a lot of entrepreneurs have the Al Capone syphilis syndrome because it was a I’m trying to get that hashtag going, by the way, at that.

Austin: Time it was curable. It was curable.

Matt: Yeah. They had penicillin.

Austin: And that’s yeah, that’s good.

Matt: It was an easy fix. An easy it was like a shot and you’re good and. Yeah, but a lot of entrepreneurs have the Al Capone syphilis syndrome hashtag.

Austin: And that’s a great book.

Matt: Title I’m going to start doing. I’ll start doing that afterwards instead of going hashtag before. I’m just going to do it afterwards. You know, like, you know, Al Capone syphilis syndrome hashtag.

But a lot of entrepreneurs have that, that fall. It’s like a fault or a flaw that they have where I’m just going to be in denial. I’m not going to I’m going to be stubborn about it. I’m going to pretend like, okay, I’m looking at my bank account.

There’s one side of that where it’s like, okay, well, I don’t know how I’m going to get an extra ten grand to make payroll this month in ten days, and I’m just going to ignore it entirely.

Or you could be like, okay, I got to compartmentalize this. I can’t ignore it. You know, let’s follow up with some invoices and make sure people are paid up and see what’s going on with our our cash flow.

And so that Al Capone syphilis syndrome hashtag is it’s a real business killer, though both mean metaphorically and literally. Like if you have syphilis and you’re refusing to treat it, not going to be good. If you’re an entrepreneur.

Austin: Either your business will fail. Yes, along with your.

Matt: Life and your along with your sex life. Probably not going to do very well either. So we’re talking about some of the mistakes. So an entrepreneur though I feel like is the leader of the organization.

They are the face of the core. The the core values stem from them. And you look at any company, it doesn’t matter how big or small it is, even if you’re a solo preneur, entrepreneurs at the top are what set the tone for the entire company. And I’m a big believer in this.

Like you can’t really get mad. As somebody who’s on your team for making a mistake. Because they’re just following what you’re doing.

So if you come in as an entrepreneur and you’re like, hung over every day and you just are, you’re phoning it in or you’re not going through the proper processes, procedures and just having systems in place. Well, your employees, your staff, your team, they’re going to follow what you’re doing.

So it’s a reflection of the leadership. So I think the most important thing that an entrepreneur does is effectively build a team and lead the team, right. Getting those players, those top talent people that you want on your team and and then leading them.

And leadership is not easy like most people who think they’re like a good leader. It’s this ready, aim, fire approach, which is not how you should shoot a gun because it’s very dangerous.

Ben: Yeah, you’ll get in trouble.

Matt: Yeah, you’ll.

Ben: Do something bad.

Matt: Ben does that outside on the highway all the time with his cap gun. Shoot at birds. Yeah, it is that.

Austin: That’s why you go on those walks around the building. Yes. Pow!

Matt: He gets he gets 12 caps per day that he gets to go fire off.

Ben: I like the smell. Yeah. Sulfur.

Austin: He goes into your office. Can I get another cap?

Matt: Ben? That was your 17th cap today, buddy. All right, so let’s let’s take a look at some of the other the top nine mistakes that entrepreneurs make. Failure to plan.

What was a team where he’s like, I love it when a plan comes together. Right. Um, there’s a quote. I’ll probably butcher it. It’s one of my favorite. But a goal without a plan is just a wish.

And I feel like that hopium drug we talk about, like, hope and just hoping it’ll fix it, or wishing it’s not going to do anything might make you feel a little better in the moment, but you really have to have a plan and doesn’t mean you have to have, like, everything laid out from day one or a business plan from day one. But if you’re not having some sort of strategy organization, that’s a big one.

Austin: I had a sales manager in radio and she was great, and her line and it always stuck with me, and I don’t know if she got it from somewhere else, but it was, you know, make the plan, work the plan that’s, you know, right. That’s simple to follow.

Matt: I mean, a plan is like it’s a checklist, it’s a system. It’s just it doesn’t have to be super complicated. It’s just okay. When you go to the grocery store, you go with a grocery list, right?

Ben: Shopping list. Not me.

Matt: And let’s just go. He just wings.

Austin: It, then he just goes there and buys meatloaf supplies.

Matt: You probably go there when you’re really hungry too, don’t you? It’s the worst.

Austin: That’s why the other. Yeah. The other day I was like. I was up till midnight making meatloaf.

Ben: Yeah, yeah. Meatloaf and mashed potatoes at midnight.

Matt: And I was trying to figure it out because your wife shared how much you spend monthly on groceries, and I am struggling to do the math.

But if you’re going there when you’re hungry and without a list, that makes sense. That makes total sense. Yeah. She shared a lot about your personal life.

And and we’re going to get to that in future episodes. Um, another mistake is all talk, no action. So this is the false bravado, right?

Austin: So many people are guilty of that.

Matt: Entrepreneurs are notorious for their egos. I mean, we all have an ego, right? But entrepreneurs, by and large, it is. It’s a confidence game. So you have to kind of fake it till you make it to a degree, but you have to be able to back it up at least somewhat at some point. Right? Right. Yeah.

Austin: There are so many people that fake it but then never back it up. Yeah. And then you just realize that, oh, you’re an insane person. Yeah.

Matt: That’s a sociopath is what that is. Yeah.

Austin: There’s a lot.

Matt: Um, not asking for help is another mistake. How do you feel about leaders who ask for help? Do you respect them more? Do you respect them less?

Austin: I respect more, right? Yeah. I respect everyone more if they’re willing to ask for help and.

Matt: Not even just asking for help, but sharing that you’re struggling with something or that you need a break or you need, you know, whatever it might be.

Austin: And not having the Superman syndrome. Yes. Where you just think that you can handle everything.

Ben: It’s much better than the Syphillis syndrome.

Matt: Yes, hashtag and I have the Superman syndrome. It’s just where I walk around in red Spanx. It’s not really a Superman outfit. It’s just kind of my thing. It’s my. It’s my Tuesdays, right?

Austin: We’d be bothered by it. You look good in it, so. Well, thank you very much.

Matt: Thanks. I mean, I spend like, four hours manscaping just to be able to pull off those red Spanx.

Austin: And I was shocked to find it was painted.

Matt: Yeah, the tube socks I painted with spray paint to look red. So, um. Impatience. This is a big one. Like shiny object syndrome is a notorious virus within the entrepreneurial community. And not having the patience to give things the time that they need that are due.

That is a big mistake. And it’s really hard because you get very passionate and excited about things and you want to go, go, go. And I’m horrible at this, but you end up saying yes, yes, yes to too many things or too quickly.

And then, you know, one day Ben’s going to just have a total meltdown and. Really just kind of snap at you in a way.

Ben: All those caps.

Matt: You know, he just started shooting his cap gun at me in the office and was saying curse words I don’t even know. I’ve never heard before. I don’t know where they came. I don’t know if they know they’re English or what, but.

Ben: You know, I’m mad. I start making up curse words.

Matt: What’s a good curse word that you made up?

Ben: Blubba Blubba.

Matt: Yeah, mine is Dave Nabity. That’s a good one. Like Dave Nabity like, that’s that’s a person.

Ben: Matt. The name of a person. That’s a.

Austin: Good.

Matt: Yeah, it’s a good curse word, though. I feel like if I was Dave Nabity, I would totally take that and own that. Right?

Austin: Take Dave Navidi’s name in vain all the time.

Matt: If you’re wondering, you, Dave Navidi is by the way, that’s a local, almost politician. He was on the city council in Omaha, Nebraska, where we’re based out of but think maybe I don’t know. I mean, you know, I know he drives a convertible and he loves that thing.

Austin: What kind is it, a.

Matt: Vw bug or something like one of those, like, kind of, you know, not a normal one, but like, it’s still it’s a convertible. Yeah. You know. No. Another mistake hiring friends. So guess.

Ben: Uh. Oh, we.

Matt: Need to make some cuts.

Ben: You hired your.

Matt: Brother? No.

Austin: You got hired.

Matt: Family and friends. Yeah. Family? Two friends and three strangers from Mexico. That sounds like a sitcom. Sitcom there. Yeah. Um, hiring friends is tough, though, too. And there’s this exercise you can do with your leadership team where you you have everybody write down, put a name and assign a role.

And sometimes they’ll be like six, seven people in this meeting. And there’s only three names that have been written down on all the sheets. You got four people sitting there with no designated responsibilities. And that happens a lot when you are just hiring friends.

And it’s really hard to have blunt conversations because it’s a business. It’s not personal. It’s not a family. Right? I mean, you family is grandma. You know, you can’t fire grandma for, you know, ruining the mashed potatoes and.

Austin: Push her down the.

Matt: Stairs. You can. Yes. And been tried. Fortunately, she had one of those electric chairs that caught her and took her all the way down nice and slow. So it worked out. She’s she’s she was notorious. It was notorious.

Austin: No, I don’t even know what your grandma looks like, but my visual was awesome.

Matt: Our grandma Nola is like, if there was a picture of a grandma in the dictionary, it would be her. Like, it was just, you know, I mean, next to, like, homemade milkshakes, mashed potatoes, fried chicken and the best hugs ever. That’s. Oh, yeah, that’s notorious

Nola right there. But hiring friends is tough. And you really only want to do that or work with family if you know for sure, you can manage it and it can work. And Ben and I have worked together for like 15. I know years like Ben just can’t get enough.

Austin: I think where that goes wrong is if people like a friend needs a job, but they’re not really, they don’t have any experience for whatever you’re going to hire them for or training or passion. And you’re just like, oh yeah, you need a job. Yeah, come do this. That’s where I’ve seen it go bad.

Matt: And I think because I thought about this when, when you came on board because, you know, we’ve known each other for quite a while and doing the TV show and everything. And so it was like, okay, well, I know he’s capable. We have like, we’re friends so we know each other.

So on the flip side, like there’s trust. So, you know, you can trust a friend, right? Most well most friends, some friends, some are just jerks.

But. I had to look at it and say, okay, but can I separate like in the workday? Like, can we separate it where it’s like, okay, so then there’s that separation of, I don’t know, not powers, but like separation of like roles or responsibilities where it’s still work. We still got to like have quality standards and critique each other constructively.

But having a friend that you can trust or a brother you can sometimes trust, who occasionally steals your left sock when you’re taking a nap. I’ve stolen it is a it is a plus. It’s just you got to kind of know it’s such a weird gray area. Yeah. You know, um, it’s kind of like dating your your fourth cousin. It’s like, why did it take four cousins to figure out that? Yeah, you shouldn’t be. I think it comes with.

Austin: I think it comes with age and maturity. Yeah. Don’t you like, like the older for sure that.

Matt: Don’t hire your best friend when you’re in your 20s. Yeah.

Austin: No. Then then you guys will probably both just party all the time and the business will go away.

Matt: I mean, yeah, especially if you were in a fraternity. Yeah. Just coming out of college. Yeah, that would be a recipe for disaster. For getting the customer is a big mistake.

And I think this is like maybe one of the biggest on the whole list, because that’s what the entire business should be focused on.

And we forget about the customer. When I say we, I just mean entrepreneurs in general. A lot like way too much. We don’t focus on the customer, we focus on ourselves or the business.

And so forgetting the customer is a big mistake. Um. This one is fearing theft. Fearing theft. I don’t even understand what that means. Maybe read my handwriting. Wrong.

Austin: I scribbled that on after I did.

Matt: You write.

Austin: Ben steal a bunch of that.

Matt: Feral theft? Did you write feral theft again on here? We’re not talking about that last couple here. Um, so perfectionism is another one. And this is one.

I kind of hate this word because people always say this in interviews. Like, what’s your what’s your what’s your downside or what’s your weakness? Well, I’m a perfectionist.

Austin: They say that it’s a weakness. Yeah, I struggle with it. But, um, I don’t know. It’s weird you want it to be the best, but like, then you can it can just waste your time. And it’s kind of hard to.

Matt: There’s like a I forget who said it, but it’s like, fuck it, ship it or something like that. Or like maybe, maybe it was Jewel. I think it was the company jewel. So maybe it’s not that great, but I think they actually.

Austin: Like.

Matt: That. It’s like, fuck it, ship it. If it’s at like 70%, get it out into the world. That is a that is a mistake. We see a lot especially with like websites and graphic design. And you can go.

Austin: Down forever because it can never be perfect. You can always find like a mistake here or there. So that’s nobody wants things.a thing.

Matt: Nobody wants perfect, right? Like imperfection is actually what people seek and authenticity.

The last mistake here is leading sales. So like leading sales, knowing how to actually lead your sales team. Because without sales, your business isn’t going to grow, it’s not going to succeed.

And it doesn’t matter how great all these other mistakes are that you avoided, if you’re not bringing revenue in, you’re not going to be in business for very long. And I think sales is such an important and old school tactic, like cold calling people is still the top way to like, drum up new business and sales.

But not a lot of people want to do it or learn how to do it. Right. So so there you have it. Those are the mistakes, Ben.

Ben: We’ll just avoid. We’ll just avoid those.

Matt: Yeah, we’ll just avoid those.

Austin: Like how those. And they really are the the hardest ones to become disciplined in.

Matt: Yeah. Discipline is really that’s if you want to pick an extra one, a bonus. Yeah. Discipline is the biggest challenge in business because it is so hard to be consistent.

And with the boring shit that’s like, no fun. Like, this isn’t sexy to do my TPS reports, you know, like, come on, I don’t want to do panels all day long. And it is important. So having discipline. Speaking of discipline, that is our episode as we got a I don’t know is it was that a good got away. We got to.

Ben: Wrap it up.

Matt: We got to wrap it up. We’re going to stay disciplined and not go over our 27 minute mark here today on the show. So thank you so much for joining us here on Midwest Mindset. You can learn more about us at the content Where if you give us 30 minutes, we give you 30 days of content. Plus Ben gives you.