THE TWIST: Talking Dollars and Sense With Pete the Planner

26th, 2018
Keyhole - Digital Marketing Agency - Joe Dudeck
Joe Dudeck
President + Founder
Categories: Interviews
26th, 2018
Keyhole - Digital Marketing Agency - Joe Dudeck
Joe Dudeck
President + Founder
Categories: Interviews
Pete the Planner - Entrepreneur Success Stories

The plot twist…that moment in a story when an event or experience dramatically shifts the future direction of the storyline and all the characters involved. I’ve always found these moments fascinating, and so I started this series—called “The Twist”—where I meet entrepreneurs to hear their success stories and explore the plot twist that led them to start their businesses.

pete the planner - logoPeter Dunn has always been a talker. From calling out coaches as the PA announcer at his high school’s baseball games to dropping one-liners in his college improv troupe, it’s just what he knows. Today, he talks money under the name Pete the Planner® — as a columnist for USA TODAY and the Indy Star, author of 10 books, and host of The Pete the Planner radio show on 93 WIBC FM. Pete also appears regularly on CNN HeadlineNews, Fox News, and Fox Business.

Recently, Pete and I met — ginger e ginger — to talk about the many entrepreneurial plot twists in his life, what we as Americans really want in life, and what he wants his kids to know about money, among other things.

See all our entrepreneurial interviews.

On his entrepreneurial lineage...

Joe: Let’s go back to the beginning. What was your upbringing like?

Pete the Planner: Yeah, I had a pretty normal childhood. Boring in a good way. I had two parents. I grew up in Speedway and then Pike Township. Went to Pike High School. And it was really normal.

I have a sister who’s three years older than I am. She was a dominant athlete, and so most of my middle school and high school years were spent living in her shadow. She won a state diving championship and dove on scholarship at Indiana University. At that time, what I cared about was sports, as a lot of kids do. And so, it was funny that, even if the local newspaper would write about things I was doing in sports, they would always reference me like, “The brother of state diving champion, Emily Dunn.”

At the time, it sucked, but it’s the greatest family joke ever now.

Joe: Of course. Good material for you.

Pete the Planner: Exactly. And my dad was an entrepreneur. He owned a plumbing business with my mom’s brother, and my mom’s dad founded it. I worked there from my early teens through early twenties, I guess. Through college.

I think it was around 17 or 18 when they came to my cousin and me — who’s a year older than me — and asked, “Do you guys want to take over the family business?”

Joe: Wow.

Pete the Planner: It was a resounding, “No thank you.” And, it wasn’t in a disrespectful way. I just really didn’t have any interest — despite the fact that I knew all the guys that I worked with and really enjoyed it. But I was already interested in the financial business at that point in time. I knew I wanted to go that route.

I didn’t mind entrepreneurship. In fact, I’ve never known anything different. People will ask me, “What’s it like taking a risk?” I don’t know! That’s all I know. I don’t know what it is, to work for “The Man.”

Joe: Right.

Pete the Planner: So anyways, my dad’s business had about, a hundred employees at its peak, or so. So, I really got a good view of what it takes to be in charge, and be responsible for other people’s lives.

Joe: Is that still operational, today?

Pete the Planner: No. They sold it, and my dad retired in his early 50s. And today at 65 this year, he’s un-retired. He’s the executive director at a Suicide Hotline.

Joe: Oh, wow.

Pete the Planner: Yeah, he rediscovered his passion to help people in their darkest time. He literally will talk people off the ledge in their worst moments.

What’s interesting now is that he does that at our family holidays. It’ll be Thanksgiving dinner. He’ll get a call, and he’ll step away to deal with it. Or, we’re opening presents on Christmas Eve, and he’ll step away to deal with it.

So, it’s this ubiquitous thing within our life that my dad is talking to suicidal people all the time. It’s really interesting. My dad’s my favorite person.

Joe: That’s so interesting. So many people will check out of life and responsibilities at that age, and he’s still giving.

Pete the Planner: It’s been very interesting. I just turned 40 at the end of 2017. And I think this is one of those ages where you think back to how old you were when your parents turned 40. Right? And, there’s a real mortality to that. There’s this sense of, “Wow, I really am an adult now.” It hits you when you think about the different stages of your life and when your parents were at those stages. It’s just mind blowing to me.

Joe: Oh for sure. I can relate to that. And how about college after you spurned the plumbing business?

Pete the Planner: I went to Hanover College. I met my wife two days before classes started. I was there for football, and she was there for cross-country. And so, on the day classes started, I positioned myself outside of her classroom. And then, we spent every day together since then.

And that was not the plan, but I loved it.

Joe: That’s cool. And, you’ve got two kids.

Pete the Planner: Yeah. Two kids — soon to be nine and six.

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Joe: What’s it like to be a dad — especially, as you said, you revered your own dad?

Pete: Yeah, a lot of pressure, you know? When you look at it that way, there’s a lot of pressure.

I’ve got an interesting family life. I’m on the road a lot, and so my wife, in many ways, has thrown herself on the grenade of parenting. She put her career on hold as a high school English teacher and cross-country and track coach, so that I could pursue what I want to do. So, it’s good.

My kids are very active. They have a lot of personality. And I’m constantly trying to figure out how much do you let their spirit fly, and how much do you make sure you’re not raising a jerk? Right? There’s a mix there.

But, they’re a lot of fun. And I love being a dad. I think my parents gave me a tremendous amount of independence. They believed in me, and the confidence they had in me was really good. I have no interest in setting my kids up financially. I don’t really care about that whatsoever. What I really want to give them is belief in them from their mother and me.

On the plot twist from comedian to financier to speaker...

Joe: I see the posts of your kids on social media, and I can see they’re pretty precocious. Are they similar to the way you were as a kid?

Pete: Yeah, for sure. I was a class-clown. Formally elected “Class Clown,” by the way — what an honor! I think when you’re a kid, it’s really funny when you’re more comfortable talking to adults. I was that way, and my kids are that way — my daughter especially. She would much rather be part of this conversation than anything going on in her elementary school.

But after high school, I got to college and a group of people decided to form an improv comedy troupe. And I’m like, “Yeah, I’m game. Let’s do it.” So I did that, and I liked it. It was interesting. They were mainly theater folk, and I wasn’t. But that was fun!

And then, when I got out of college and moved back to Indianapolis, I went down to ComedySportz and did comedy down there for four years or so while my financial business was being built.

And that really became the intersection of being Mr. Funny guy on the weekends and trying to be viewed as an adult during the week. And then, at some point in time, I had this intuition. What if I just stopped putting my personality into the weekends and started being myself all the time?

Joe: Mm-hmm (affirmative).

Pete: And so that was the beginning of “Pete the Planner.” It started with an email address — — because I needed to change my email address. And it stuck. By no means was it a strategic decision to brand myself. But it was catchy, and people gravitated toward it.

This was toward the end of 2005, and I had a friend who started doing marketing for me. I had a blog that no one read, but she insisted. I remember the day she was like, “Alright, you’ve got to make a decision. Are you going to be on MySpace or Facebook? If you’re on MySpace, this is the implication. If you’re on Facebook, this is what you have to do.” We chose Facebook and put some energy into that.

And then she was like, “You’ve got to try this Twitter thing.” And I’m like, “Why does anyone care what I’m having for lunch?” But that was putting your personality into your business.

Joe: Before we transition away from comedy, I wanted to ask about “the award-winning comedian” claim on your website. What kind of awards are they handing out to comedians?

Pete: NUVO named me one of the top 30 artists, if you will, at the end of 2004. And that was interesting. It was a lot of visual artists and musicians. We did a lot of long-formed shows at ComedySportz at the time. They weren’t your traditional family shows — a little more intense. And so, I was recognized through that.

Joe: When did the comedy bug first get you?

Pete: I always had a little bit of an interest in broadcasting and microphones, maybe back to when I was the baseball stadium announcer at Pike High School my senior year.

I got in so much trouble because I would basically do bits on the public address system during the game. We had a coach named Dave Bachinsky. I remember between innings one day, I just randomly said, “This Tuesday is Polish Teacher Appreciation Night. First 100 fans will get a signed picture of Dave Bachinsky.” And, I remember the coaches looking up into the press box laughing — but mad too.

"It's weird. It's been a career of assumed authority. I'm not a writer, and then I am a writer now. I'm not a broadcaster. I am a broadcaster now. I'm not an expert. Well, I'm an expert now. And, there's a lot of BS in that, at first because you're lying to yourself and, arguably, everyone else."
Peter Dunn

Joe: Oh no way!

So, I always liked that. And I always thought that someday I’d like to get into broadcasting in some capacity. As a kid, I wanted to be a sports broadcaster because that’s where the money seemed to be.

But then, I got opportunities through some content creation in early 2006. I released a book — a terrible book — and went on WISH-TV and Inside Indiana Business with Gerry Dick that same day oddly. I was 27 or 28 years old, and when the camera and lights went on in the studio, I was a gamer. It just felt great. My nerves were going nuts, but I was like, “Oh, I like this!”

Joe: Mm-hmm (affirmative).

Pete: And they seemed to too. They said, “Hey, come back and do this all the time.” So I did, and that led to a radio show in which I paid to be on the air. And I got to do my show for free, although I was paying $26,000 a year to do a show.

And then, a couple years into that, the radio station was like, “Hey, we’re going to stop charging you, and start advertising for you because it’s going well.” And then, that kept going, and at some point I started calling myself a broadcaster.

It’s weird. It’s been a career of assumed authority. I’m not a writer, and then I am a writer now. I’m not a broadcaster. I am a broadcaster now. I’m not an expert. Well, I’m an expert now. And, there’s a lot of BS in that, at first because you’re lying to yourself and, arguably, everyone else.

Joe: You’re trying to convince yourself just as much as you’re trying to convince others.

Pete: There are still times now where I’m called or labeled something, and I’m like, “I don’t know if that’s what I am.” But then when you see that people are really getting behind that label, you’re like, “Actually, I am that.” You know?

Being a columnist for USA Today is one of those weird things. It’s one of the largest newspapers in the world. With all the other Gannet papers that I’m in, it’s five million readers a week. And yet sometimes I’m like, “I think I’m faking it.” I feel like it’s not real. That it’s going to go away. It is real, but I have to admit there are still times when I wonder if everyone will figure out I don’t know what the hell I’m talking about.

Entrepreneur Success Stories

Joe: Mm-hmm (affirmative). Sounds like you were more just remaining open to things as they came your way, as opposed to pursuing specific accomplishments?

Pete: I would say, when I started this whole “branding thing” in 2005 — by the way, if you’re transcribing this, I just did air quotes — I really did have my focus on being considered one of the top three financial experts in the country. Dave Ramsey was right there, as was Suze Orman. And, I always felt there was a place for a third. That’s what always guided me.

But the last few years, it doesn’t guide me as much. I have different goals. Whether I’m that now or not, I’ve actually stopped caring. Right now, we’re sitting in my studio, and I even got to the point where I don’t care about the size of my audience. But Pete The Planner TV is a show I want to do. We get hundreds of views — sometimes 1,000. That’s nothing. But somehow I’ve convinced myself that I just don’t care.

And that is to say also that I’m much less interested in being Pete the Planner now than I was before. I’m much more interested in being a CEO of a financial company — developing talent, and providing solutions for people. I don’t know if that’s come with maturity, or what. But, I don’t revel in the low-key celebrity that is, “Pete the Planner.” I just don’t particularity care anymore.

Joe: I hear you. When you wanted to go head-to-head with Ramsey and Orman were you aware then of your distinguishing factors?

Pete: When I was talking with my marketing friend —Raquel Richardson.

Joe: Oh, yeah. She’s great!

Pete: She asked me, “What are your defining characteristics?” And I got them down to: I’m young and funny. And, in the way that she can do, she said, “First of all, you won’t always be young. So, don’t waste it. Don’t waste using those words. And by the way, don’t call yourself funny because that’s not for you to say.”

So, then we got to this point of, what is my differentiating factor? And what I’m about to say is not pejorative in nature, but we got to this point where we felt like Dave was yelling down the mountain at people. He’s at the top, and he’s saying, “You’ve got to climb this mountain. This is how you climb the mountain.”

Whereas we saw ourselves as I’m walking up the mountain with people. You know? That’s a really cheesy metaphor, but that’s where we got to. That I’m going to nudge someone with my elbow, and be like, “Hey, man. We can do a little bit better.”

I don’t really get into the, “I’m going to yell at you to change your life.” The Dr. Phil, “You’re an idiot!” I don’t think you’re an idiot.

Joe: Mm-hmm (affirmative).

Pete: And I’m not going to act like I’m an idiot, so that people will listen. We all have our behavioral challenges, so why would I crap on yours?

But all of that being said, what I think I bring to the table in relation to Dave and Suze now is practical answers for real people. I don’t want people to have to scream, “I have no debts!” I don’t want people to have to feel bad about themselves that they have a mortgage and eat beans. That’s great.

I’m so thankful that that’s what people have chosen to do. I just wouldn’t do it.

On the search for self-control in life...

Joe: We’re sitting here in the Village of West Clay — a very surreal place . . .

Pete: Yeah, you’re telling me.

Joe: . . . and was thinking about the tagline you have on your website: “Never worry about money again.” And I have to think the financial worries are much, much different here than those living in many other segments of Indianapolis — or across the country. So when you’re speaking to people from such diverse walks of life, is there a basic tenet or truth you hope they all get from?

"I think what we really want is self-control. And what we seek is self-control. Because there's so much we can't control. All you can truly do is control your actions."
Peter Dunn

Pete: Yeah. I just recently arrived at the answer to that in the last few months. I had this idea for a couple years now that all we want out of our lives — financially speaking — is a solid income that provides us a reasonable lifestyle. Okay? That’s number one. We also don’t want financial stress. And then, the third thing is, we want a successful retirement outcome.

So after years of writing, studying, and research, I had concluded that those were the three things we want. You can categorize everything into those three things.

Joe: Okay.

Pete: But I’ve taken it to a different point from that. I think what we really want is self-control. And what we seek is self-control. Because there’s so much we can’t control. All you can truly do is control your actions. And so many people suck at that in various stages of their lives. How they talk to their loved ones, their spiritual journey, food, exercise, money, consumption habits from a media standpoint.

And so, I’ve gotten onto this own personal journey of self-control with my health and with fitness. I’m not super fit, but I’ve worked out, as of today, 120 days in a row. To me, that is nothing more than taking control over my time.

I think, financially, we look at our lives, and we say, “I want this. I want that.” I’m like, “Okay, great.” You want self-control. When you buy something you can’t afford, you’re trying to take control of a situation you really don’t have control over.

Self-control is looking pleasure in the face and saying, “There’s something bigger here than this pleasure. This pleasure will put me in a deficit.” And not a metaphorical deficit. Self-control says, “It’s just not in the cards.”

The best way for me to explain it — and it’s a dumb explanation — but I love to eat a cheeseburger, have fries, and drink a beer. I love it. It’s delicious. And when I’m on the road, I get done with a gig and get to the airport. And wherever the hell I am, I have that meal and then fly home. It’s comforting. And so, when I was trying to think about having self-control of my health, I would look at that situation and say, “I’m not going to do this. I’m going to sacrifice.” I’d text my wife, and I’d say, “Hey, I made a good food choice.” And she’d say, “Oh, that’s great.” And she meant it, because she’s supportive.

But, then I realized that, to have self-control, it’s not a sacrifice. That’s some real superficial garbage, if I have to go, “I made a wise food choice.” That’s not self-control. Self-control is looking at the pleasure and being like, “I’m good,” and not viewing it as martyrdom.

And so now I can look at the favorite things that I love and go, “It’s just not part of my plan right now.” Think about having control over all the things that tempt you the most. Imagine all the things you could avoid that accompany the pleasures we seek.

And I think what I’m trying to do in peoples’ lives and in the financial industry — with large, multi-billion dollar companies who now subscribe to what I say and pay me to say it on their behalf — is that we seek control of ourselves. That’s the common thread.

Joe: Yeah, you’re right. That lack of self-control can own us.

Pete: Think about this. Every extra dollar above your base need that comes into your life does one of two things: You use it to get stuff or you use it to create stability. I think no matter who you are— and especially for those folks who make more money — you tell yourself a lie that the stuff is justifiable because your income is your stability. Your income is not your stability. Right? We think, “Oh, I’ve got a great job, I’ve got a solid income. That makes me stable.” To hell it does.

And so, when I look at the money that comes into my life, personally, I view it as an opportunity to create stability. I’m on a mission to not need money. And that’s not because I have money. It’s because I don’t gather obligations. I’m 40. When I’m 53, I won’t need money. My kids will be in college. Our house will be paid off. That is $5,000 dollars a month I won’t need that I currently do because I’m saving for those things and paying for my mortgage.

So, that’s the journey. As a financial expert, my job is to show you, Joe, how to not need money. Not to show you how to get a bunch of money. And, I think that’s why we’re different.

Joe: That’s an interesting philosophy.

Pete: I’m not evaluating you physically, but you seem like you’re in good shape. You don’t have a potbelly or anything like that. Have you ever been there?

Joe: Yeah. Talking about health, I actually lost 35 pounds because of some lifestyle changes my wife and I were making.

Pete: Great! So during that journey —you know when your stomach shrinks? You change the quantity of food you eat, and then less satisfies you? And, if you eat more, you all of a sudden are uncomfortable with the old food you used to eat, because your stomach is bigger. I view that financially. We can shrink our stomachs, and what used to satisfy us is gross.

Joe: Mm-hmm (affirmative).

Pete: So I find as people head toward retirement — to their 50s and 60s — I think we’re trying to shrink our stomachs. We’re trying to find this healthy consumption level.
Think about the classic American CEO from 20 years ago, if you can. It’s this weird, iconic, fat and happy white guy.

Joe: Of course, yeah.

Pete: Old, fat, happy, gross. But, that was 20 years ago, right? Think of the iconic CEO today. First of all, thank God, it’s to some degree different genders and different races. But it’s also the picture of health. It’s someone wearing Lulu Lemon. It’s someone eating organic. It’s someone who values self-control, in this Zen state.

That I like because it’s a different view of wealth. Look at the pictures of Jeff Bezos. He looks like The Terminator now because he had that much control over himself and his body. I’m really into that idea. I think it really translates into how the average person should view wealth and themselves.

We have two cars. We have a 2004, and we have a 2008. At various times, they sound like horrible animals when they start or back-up. But I don’t care. Yeah, I would like a much newer car. I would like to enjoy that. But, I’ve chosen not to care, because I care more about other things.

Joe: Mm-hmm (affirmative).

Pete: And, that’s not being cheap. Right? It is really more of a trip down the minimalism path.

Joe: There’s finding this balance. Sometimes, I think, we’re not enjoying the present because we’re throwing everything toward the future. But then, there’s the other side, where we say, “Screw the future. I just want to get everything today.” So it’s about finding that balance between both leaning into enjoyable things today and also putting some things aside to enjoy it later.

Pete: I doubt I came up with this phrase — but around here we say, “Make tomorrow easier.” You’re faced with a situation, and you say, “Okay, am I going to take this advantage and leverage it for now, or am I going to do myself a favor for later?”

And I love that idea of not backing yourself into a corner. I hate when people say things like, “Well, I’d rather live in the now, and not put money away for retirement. Because who knows what the future holds.” Well, here’s what the future holds: a broke you. Someone that is scrambling because you didn’t do yourself any favors. I guess that’s the nature of what we do.

And the great part about that, Joe, is that’ll happen at every income level. We’ve dealt with CEOs that make seven figures, who ended up broke. And we’ve worked with ones that haven’t ended up broke yet, but will because of that very scenario. Their stomachs are too big, and they want too much.

On what he wants his kids to know about money...

Joe: Just a couple more questions. My son is four years old, so he’s younger than your two kids.

Pete: By the way, your kid is really cute. He is. Every picture you take of him, maybe it’s just your photography, I don’t know. What a cute kid.

Joe: Oh, thanks. He’ll probably be that kind of kid who’s calling out people at a baseball game. He also enjoys conversations with adults. But back to the question, what are you teaching your kids about money? And how does it differ from what you were taught growing up?

Pete: Yeah, there’s definitely some crossover. I think the earliest conversation I remember having with my dad about money — I don’t know, this is weird — we were sitting in Speedway, Indiana, in the parking lot of what used to be a Marsh. My dad went in to grab something — this is when you could leave your kid in the car and not go to jail — and I grabbed all the quarters he had in his ashtray. I remember he came out, and it looked like I had taken possession of them for myself.

And he decided this was a teaching moment. He’s like, “Those are mine. Those are not yours.” I’m like, “I know.” He’s like, “No, you took them.” I’m like, “I didn’t take…”

Anyway, where this is all going is, he basically said, in a very loving way, “None of this is yours. Everything you think you have, you have nothing.” And there are people who are going to read this and think that’s awful. I think it’s great, and I still think it’s great!

I still tell my daughter, because she thinks — talk about assumed ownership — my daughter thinks “we’ve” done it. She hasn’t done crap. And we tell her, “Look, you get to stay in your room. You’ve got pretty much nothing, other than what’s in your piggy bank.” And, I think that’s important.

And, so I guess I teach them that they’re going to have to build their own stuff. I tell them they can’t live with me after college. Because I know that 41% of kids today, 18-34-year-olds, still live at home at some point.

Kids Finances

Joe: Wow.

Pete: And I’m not letting that happen.

Joe: Yeah, Quinn’s still at the age where he wants to marry mom and live with us forever.

Pete: Yeah, you’re still good there, at four. But, I’ve always thought — and you and I have done some work together back in the day with Lemonade Day — I always thought that was really good teaching tool.

Joe: Mm-hmm (affirmative).

Pete: And the capacity of what you can learn grows from year to year. But I always enjoyed that — and my kids still look forward to it —because it’s money they’ve earned.

Joe: Quinn and I just had a conversation yesterday when I picked him up from school. He said, “I want to get a skateboard.” Who knows where he got that idea. I’ve never owned a skateboard. But I said, “Okay, you’ll have to earn some money.” And so last night he earned a quarter per chore he did. He’s obviously still a long way from getting a skateboard, but it’s the process.

Pete: Yeah. That’s funny. I remember buying my Nintendo. I bought it at Kohl’s in Speedway — back when Kohl’s had toys. I bought it with my own money, and I’ll never forget how I felt.

I try to give those moments to my kids. But of course, they’re still like, “Go get me a fidget spinner. I’ll give you seven dollars.” Huh? What’s happened here?

On embracing his own gingerness...

Joe: Last question, and it’s a softball. You seem to be very proud of your “gingerness.” What does being a ginger mean to you?

Pete the Planner: When you’re a kid with bright red hair, it’s just not an attractive quality. I’m half serious right now. You basically have to figure out a way to get people to ignore your aesthetic. And I’m sorry. I’m guessing you don’t have a lot of teen ginger readers?

Joe: Probably not.

Pete the Planner: But people call you Ronald McDonald and Carrot Top. I mean, it’s no different than — my wife’s super petite — so people say, “wow, you’re short.” It’s the same thing.

But I have to admit, when I see a kid — an awkward looking “ging” — out in public, I just want to grab the kid and say, “Hey man, it’s going to be okay.”

Joe: I saw some article that said, because of Ed Sheeran, our lifestyles dramatically improved.

Pete the Planner: Good for him! I will say, my eight year old will sing in the car, “I love the shape of your body.”

Joe: Thanks, Ed.

Pete the Planner: Yeah, that’s disconcerting. I’d like to thank a ginger for that.

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