REPEAT is a special interview series underwritten by CliftonLarsonAllen where we take a deep dive inside the minds of Minnesota’s rare repeat technology entrepreneurs. Repeat means to start a tech company, exit said company, and return start another one.
Repeat entrepreneur is Don Smithmier, currently leading two tech companies simultaneously: he’s the Cofounder/CEO at GoKart Labs and Founder/CEO of The Big Know; previously, he cofounded two tech companies — BringMeTheNews & Sophia Learning — both subsequently acquired.
Smithmier is among our guests of honor at the upcoming Founders Respect and Recognition event on April 5th.
When and where were you born?
In Madison, Wisconsin, 1970, and I was raised in McFarland, Wisconsin
What is the first recollection you have of money?
My father was a business owner when I was a kid, he owned a couple of drugstores. There was a supply room in our basement – everything from jewelry and toys to trinkets was there. I would go down and make my own store and then make my sisters come down and buy from me. Sometimes I even pilfered jewelry from them directly and made them buy it back from me. I loved the idea of the storefront, with signs and transactions, it was a lot of fun…I haven’t thought about it in years. Everything got returned at the end, even the money I’m sure.
How old were you about?
Probably about 5 or 6
How many siblings do you have?
I’m the youngest of Five; I have four older sisters and they range between 6-12 years older than me.
What’s the first memory you have of what your father did, as a business owner?
I remember his store in DeForest, Wisconsin…he was also named Don, so there was big Don and little Don. I loved being able to go into the back of the store like the employees.
Were you exposed to his store and business a lot?
Not so much, actually. He was always on the road and I think he was on the road because he was looking for new and interesting things to put into the store. Buying from wholesalers and importing to the store was done a lot differently back then.
What about your mother?
She worked in the offices of social services for Dane County.
How long did you father pursue the drug store business for?
Unfortunately he passed when I was eight years old.
But long enough that it sounds like he wore off on you a bit?
I think so.
Did you ever have conversations with him that you can remember about business?
Not really. My clearest memory is playing catch and baseball with him when he was around. He wasn’t a real talkative guy, but we would always make it a point to play catch together or go fishing. I was such a young kid, I just don’t have the memories there.
Growing up was money ever discussed or ?
Yes. After he passed unexpectedly in a drowning accident, our lives were really turned upside down. As a widow, mom started working full time, but as you can imagine as a secretary working for the county social services department, she wasn’t making great money. I knew that money was scarce growing up.
And yes, it was tight for a while, and I’m not sure how she figured it out, but we always had the basic needs met…food on the table, a place to call home, and even a car to drive when I was of age.
Did you sisters also work?
The Smithmier house was babysitting central…we all held at least part time jobs throughout high school as a way to pay for the personal things we desired. Working was a natural thing for all of us.
What was your first job?
Shoveling driveways and mowing lawns, until I could get a real job.
About how old were you when you started doing those types of jobs for money?
Eight or nine years old. I had a few neighbors who hired me for that type of manual labor. I remember making five bucks to do a lawn, or a driveway.
Did your mother ever talk with you about money?
Not really. I do remember her using the kitchen table to spread out the bills and manage finances. I knew she was under duress and figured that the more money I could make the less pressure it would put on her during those times. I think we were all pretty self sufficient.
Generally what were you doing with the money you earned?
I always wanted to have a pocket of some spending money. Growing up out in the country, there was a bait shop with a candy section. I remember going down there to buy soda or a candy bar. Maybe going to a movie, and just hang out with friends.
What did you think about the work you were doing?
It was just what needed to be done at the time…I didn’t relish it, but I didn’t hate it. I actually battled a lot with my mom about mowing our own lawn more than anything.
Did she compensate you too?
No. We didn’t have allowances, but we were just expected to chip in on chores. But she did cover my basic stuff now and again, like a pair of shoes or a baseball glove, etc. I started playing baseball around seven or eight, but then got into basketball, football and baseball in junior high – I was a three sport athlete.
Did you continue to play sports throughout high school?
I played football and baseball during all four years of high school and baseketball through my sophomore year because it was the winter sport and I ended up getting my first real job as a dishwasher at a restaurant called Bonanza. And during the summertime, generally, I was working as a parts and equipment runner driving a van full time.
Did you enjoy those jobs?
I really did, I liked going to work. I’ve definitely had some jobs that I disliked back in the day, like being a seasonal strawberry picker – that was backbreaking. Or the job I had doing masonry labor, which was really hard. All those jobs gave me an appreciation for hard work and earning some money, but it also motivated me a lot to go to college and get a degree.
Do any of those stand out as being lucrative despite the challenges?
The construction job was one where I knew it wasn’t going to be fun but it paid higher than anything else I could do at the time, so I bit the bullet to make as much as I could that summer.
What did you do with those earnings?
I paid the way for college tuition and rent. Nothing too fun, just covering the basic overhead at the time.
What kind of student were you?
I did well at school. I think I could have tried harder, but school came kinda easy to me.
Were you socially popular in high school?
I had a lot of good friends between sports and music. I was involved in so many things – sports, school newspaper, I was class president, in the choir…I was really stretching things now that I think about it, which has been a constant theme in my life. It’s still one of my strengths and weaknesses, I think, in that I don’t have the ability to ignore things that are interesting to me…from grade school on it’s been like that.
I remember back in sixth grade, there were no organized sports at the time, and I asked the principal if I could start a flag football league. I started that and used the xerox for promotions and schedules, etc. It was a blast! That was probably the first thing I remember thinking ‘this doesn’t exist but I want it to exist’ so I started it.
What was your relationship like with your sisters growing up?
The last of my sisters moved out when I was in seventh grade, so I spent most of high school living with just me and my mom, and it was great. It was fun when they came back to visit or we went to visit them at school.
Were they all working in their own respects?
Yeah they all went to college and held jobs. I always respected them because they are smart and productive. Doing your best and working hard was just part of the program.
Where did you go to college?
The University of Wisconsin – Madison.
Did you pay for college yourself?
Yes between summer earnings and student loans. This was a different time, where you could earn enough in a summer to pay for a year of tuition.
What did you study in college?
The first couple of years I was pretty lost to be honest… I was really into music back then – and I still am today – and my hope was to build a career in the industry, with college and the degree as a fallback.
One of my favorite memories was going into Smart Studios in Madison, owned by Butch Vig – who went on to produce Nirvana’s Nevermind album, and Foo Fighters stuff. He was such a simple humble guy and he did our first demo.
I remember taking a semester off and going out west to California for the first time during college, promoting my demo tapes and exposing myself to the scene.
But that didn’t go very far at the time, I thought it would be easier than it is. But when I came back to school I was pretty motivated for my degree. I loved studying history and was became a history geek, still am to this day.
What’s the genesis of your musical interests?
My father was also a singer/songwriter, so it’s in the genes, but I remember when I was 14 it hit me. I taught myself piano so that I could write my own songs.
When did you first make any money from your musical abilities?
At 16 I was in a band called Innocent Bystander. I remember our first gig on Halloween of 1986 and we got paid $200. It was amazing to get paid! I remember doing weddings for a time, we had some good gigs and depending on the show, would bring home some good earnings. It’s always been a driving force in my life, writing lyrics, songs, and dreaming about it.
I recall in 1989, we rented a house for the summer and cleared it out only to replace it with all our musical instruments, it was such a blast playing whenever not studying or working.
I was always the one putting together and organizing and maybe even motivating the bands.
How did your reconcile the potential income and lifestyle of becoming a professional musician with the actual small time jobs you were doing throughout high school and college?
Yeah. It’s expensive to even be into music, such as instruments and studio sessions. Any money I made from music went back into music and the side jobs were to cover tuition, food, gas and the necessities.
When was the first time you used a computer?
In the sixth grade, we had an Apple II and then I actually had a computer science class in highschool, but I didn’t think anything of it. And then in college I remember using theirs to write papers. I was probably 24 or 25, well after college, when I was able to purchase my own computer for the first time.
What was your first job outside of college?
My last couple years of college I worked in an apartment community as a leasing agent, and got free rent for a bit after graduating. My then girlfriend, now wife, went backpacking in Europe for a few months…and when we got back, we wanted to leave Madison and we were choosing between Chicago and Minneapolis. She was offered a job in advertising in Minneapolis and one of my songwriting partners was also living in the city at the time.
So we moved to Minneapolis in the winter of 1994 and my plan was to really dig into music teach some social studies and get ready for graduate school, while I got a job at Guitar Center.
What happened next?
I remember waiting for my financial aid check and it never came. I went into the office of financial aid (after school had started mind you), and found out that my paperwork never went through and subsequently made me ineligible for financial aid. So they held my spot in the program but I actually had to drop out. We were really poor right around that time, couldn’t even pay rent, and things got desperate.
So I went to a temp agency the next day and the first place they sent me was this random startup company run by Steve Shank called The Graduate School of America, which would later became known as Capella University. That ended up being the greatest accident of my life when I became a temporary receptionist answering phones and making coffee.
I’ll think about that to my dying day – how did that happen?
But it was in education, it was using the internet, and I got intrigued. When I started to realize who Steve Shank was, what he had previously done and the fact that I was working for him now, I thought holy crap, there’s not a lot of guys like him around, so I stuck with it, basically stalking Steve and pushing for more responsibility.
So I opted not to attend grad school and finally they relented and hired me full time as an assistant to Steve’s cofounder who was president of the school. I knew I could always go back to school, but for the time, this was the opportunity. That, and one of the bands I was involved in started taking off so I became very immersed in both of those pursuits for the next few years.