From the Garden to the City: The Epic Entrepreneur’s Story

Every entrepreneur has their own version of the classic “entrepreneur’s journey”. They usually share this story at the beginning of an interview or podcast. I’ve never been interviewed or been on a podcast so I decided to write my own. I’m choosing myself. 🙂

White Lamborghini Toy Car

Family Background

From the time I was born my family moved about every four years. Two of those houses were in Missouri and two were in Indiana. When I lived in Missouri I was young, but I remember I had this white, Lamborghini Hot Wheels car. I remember telling my dad I wanted to start a Lamborghini car dealership when I was older so that I could sell Lamborghini’s to kids like me for a $1. I remember my whole family laughing at me.

My mom volunteered at church events as a clown. She would come up to me and say, “I’m your mom,” and I’d say, “No you’re not!” and run away in fear. She sold Tupperware on the side. I remember her having Tupperware parties, but mostly I remember how much Tupperware we owned. I still use some of it today in my own house. This was my first view into entrepreneurship, which I sort of later followed when I was in Amway for a year.

My dad worked at GM during the night and during the day would volunteer at the church doing maintenance work. He would change out light bulbs in the ceiling of the sanctuary using a giant ladder. I remember watching him and wondering if he was going to fall. I’m scared of heights. We did a lot of land sculpting at every church we ever attended. For some reason, my dad just liked moving dirt around. He liked how dirt shaped water’s direction.

My First Businesses

One day after moving to Indiana I was walking through a shopping center with my older brother and we went into a Hooks Drugstore. He bought some baseball cards with his allowance and I was hooked. I collected baseball cards, bought Beckett Magazine price guides, and traded with friends. I never made any money, but this was my first experience with buying, collecting, and curating something with the intent of future earnings. I had a trader in my neighborhood in Southport that shared with me his dream of opening up his own baseball card store. This inspired me. I wanted to open up my own baseball card store. One day he setup a professional-looking stand in his garage and operated a neighborhood store for a day. I really looked up to that guy and always wondered how he turned out. I don’t remember his name though.

I also had small stints in buying candy and gum from the grocery store to sell at school. There was a time when “sour balls” just came out, which weren’t available from vending machines at school. I’d go to the grocery store, buy a bag, and sell them at school for 10 cents a piece. I actually didn’t sell any though. It was a complete failure. By the time I got into the game, I was already too late, the market was already saturated with other sellers. You see, it wasn’t my idea. I stole it from someone else – someone who had greater access to capital (their mom) and more prone to risk (willing to ask for the sale). Not only did my competitors have these things, they had prior experience selling Big Red and other types of gum. This is the same guy who later shot me in the back with his BB gun and gave me a bad haircut.

His name was Joey. We were both in 5th grade and one day Joey and I were walking home from that same strip mall in Southport. We started to come up with a plan for a new type of business. We both liked going to the local Putt-Putt and playing arcade games so we thought it’d be cool to start a small theme park or game center where you could do things like ride go-carts or fly small aircraft in addition to your standard arcade. We drew out pictures and made grand plans. We were doing it for kids like us who didn’t have a place like that. We were our own customers. We were scratching our own itch. It was “selling Lamborghini’s for a dollar” all over again. It never happened.

Business Education

Middle school was pretty much the dark ages of my entrepreneurial journey, but in high school I really ramped up. I started an antique business with a friend, started taking business classes at school, began editing websites on the side, started a band, and subscribed to INC and Entrepreneur magazines. When we had Career Day at school I told a speaker I wanted to “own my own island”. I was rude and full of hot air. I didn’t understand at that time how much value I would have to provide the world in order for me to one day afford my own island. I didn’t learn that until much later.

I kept studying business in the various colleges I attended. Each one taught me a little something different. At Kentucky Christian College I learned about how much I don’t like accounting. At Milligan I learned that first impressions make a lasting impression. At Ball State I learned about art. And at IUPUI I learned about computer science. I took 3 classes on Microsoft Office, 2 speech classes, and 1 marketing class. I took 2 years of Accounting in high school and 2 years of Accounting in college. I joined every business club I could find and failed 3 out of 4 of my math classes.

I don’t feel that I learned that much from college, but there were a handful of professors that made an impact on me. Dr. Charlie Starr, a literature professor at KCC, taught me about symbolism in movies, and although I can’t remember all of their names, the most impactful teachers were my literature teachers. Those were the ones I seemed to connect with the most in high school and college. The other most impactful professor was Andy Harris at IUPUI. He taught me about computer science and STAIR, which is an iterative method of problem solving, similar to customer development.

Business Development

I made the mistake of thinking that a college education was the key to any sort of financial windfall. In fact it had the opposite effect. I became debt-ridden and after I graduated I was no better off in the job market than the day before I graduated. I even asked my employer at the time, Old National, for a raise, but they said no. It wasn’t until I went back to school at a technical school for a specific skill set that I was able to get a higher paying job. However I later learned that the thing that actually helped get me that job was what I was doing on the side: web design. They wanted someone who could do IT work and help out with their website.

In my last year of IUPUI, Jason and I worked together to build a computer repair company called Neighborhood Geeks. After I graduated college, instead of going to classes in the morning I started going on IT service calls. I had no formal education as an computer technician, but I knew a lot about how Windows XP worked and had a good idea of how to troubleshoot problems. Google, like now, was our friend. After two years of not getting ahead in my day job at Old National, I started get CompTIA and Microsoft Certified. I still couldn’t find a better job so one day, I just quit.

A coworker asked me what my boss, Corey, said when I quit. He said, “You filled out the wrong form.” I couldn’t help but laugh. Old National didn’t use to have a formal “2 Weeks Notice” form so years earlier Corey had me make one up for our department. I used the form I had made, but by the time I quit, Old National’s HR department had come up with their own form. I had worked there full time for 6 years. It literally took me an hour 1-way to get to work everyday. I drove through rain storms and snow storms. I made stupid mistakes that will haunt me for the rest of my life. I essentially grew up there, but it was time to move on.

Career Development

2 days later I got a job at a call center helping teachers learn how to use web-based software to make tests and quizzes for their students. It was brutal, but even in that environment, I added value. There was a particular problem that no one knew how to fix and people would often call in about it and we’d have to say we didn’t know. One day I decided to dig into the problem and I discovered what was causing it and how to work around it. I was one of the few people who didn’t get laid off during the slowdown, but that’s when I got the opportunity to work at IBM’s call center, so I left after working there 2 months.

I worked at IBM 3 days before I got the job doing IT full-time. The first job I ever had was washing dishes for $4.25 an hour. I started Old National in Muncie at $7.47 an hour and ended in Indianapolis at over $12 an hour. The call center in Lebanon paid $10 an hour and IBM paid $11 an hour. My new job as an IT professional paid $20 an hour, which was quite a big jump for me at the time, but I stayed at that same rate for 5 years. Despite moving on to a business analyst position at another bank for 3 years and working as an interim manager at a dental office for 9 months, I stayed at that same rate until I went back to being an IT professional for a new rate of $25 an hour.

But I was tired of “trading dollars for hours” like Robert Kiyosaki talks about in Rich Dad, Poor Dad. Even for the year in which I ran my own consulting business doing IT and web services I was still trading my time for money. I longed to move beyond the employee or self-employed roles (or the technician role in The E-Myth Revisited) and into the business owner or entrepreneur role, respectively. I needed a product or service I could sell systematically that took my time out of the value equation so that I wasn’t the one holding myself back from earning the income I wanted to fulfil my vision for the future.

Vision and Mindset

I’ve spent a lot of time learning about how to start a business. I’ve read Guy Kawasaki’s The Art of the Start. I know you need to start with a mantra, make meaning, and have milestones. I read Jim Collin’s Good to Great. I know that you first have to get “the right people on the bus.” Eric Ries’ Lean Startup says to start with the product and ask people if they want it. There are many ways to start a business, but I know some of the worst include choosing a business name, buying business cards, incorporating, and designing a logo. None of those things bring in new customers or revenue. That’s how I developed the theme of #SellFirst, and it’s a tag I own on Twitter.

Sell First” is a mindset that says, “before I invest more time, energy, and money into this new business, I am first going to ask someone if they want to buy it.” I believe that sales is essentially “asking someone to buy something.” In high school Jason and I called this “spontaneous asking”. We found that when we asked for something, we were much more likely to get it than we did not ask for it. This seems obvious after the fact, but there is much fear in asking, which may be part of the fear people have of selling. I certainly still have that fear, but it’s something I’m learning to get over as I view it as more important than marketing. Marketing Supports Sales.

I’ve been listening to a lot of podcasts and motivational speaking lately and several reoccurring themes have emerged. The first one is the need for a vision of what you’re future will look like. This sets your mind in the direction it needs to go. The second is the need for mentors and education that gives you the information you’ll need to get to where you’re going. The third thing is hard work and the ability to temporarily discomfort yourself now for a better future later. Extraordinary effort now is greater than the same amount of effort spread out over time. The fourth thing is your product. When given the choice between working on anything else and your product, always choose to improve the product.

Product Development

I live in Tipton. I’ve lived there for most of the last 10 years. It’s a small town with little to nothing going on. I have to drive at least a half hour in any direction to see anything other than cornfields and pickup trucks. But it’s from this location that I’ve worked professionally for 10 years, developed and ran side and full-time businesses, and raised a family (I now have 5 kids). It’s out of this desolated place that I’ve come to shape my ideas of place and community. It’s how I came up with the ideas for Seektivity and Outure. I believed that it didn’t matter as much where you were, but who you were hanging out with and what you did with the situation. Even Tipton could be a cool place with the right people, the right knowledge, or the right stuff.

I had a vision of a mobile app that allowed you to post and activities and things to do around you. If you discovered a tennis court you could add it to the app and tag it with “tennis” and the next person who came there might add “badminton”. In the same way, someone might find a baseball diamond and first tag it with “baseball” while someone else might tag it with “Wiffle ball” or “softball”. If Foursquare is for tagging places to go, Seektivity would be for tagging what there is to do at those places. There may be a hundred different fun things to do in Tipton, but without an informational tool like Seektivity, I would never know about them. In this way, people can transform their communities into more active and happier places to live.

In late 2012 and early 2013 I started getting interested in physical products and ecommerce. That’s when I got the idea to create products to help Seektivity users get more out of their communities. Outure was developed out of a need to facilitate “activity in your own backyard.” I felt that outdoor adventure companies often glorified exotic places like mountaintops and sunny beaches while most of America lives in mostly flat, mostly dry areas of the country. That doesn’t mean there isn’t fun things they could be doing if they just had the right information, similarly interested people, and the right equipment. By providing the people with the gear to have fun in their own backyards, my mantra in both products is to “facilitate play”.

Outdoor Adventure with Outure

The Reality

The reality is I’m not as great as I thought I was. I never finished making Seektivity. I got a minimally viable product (MVP) and stopped working on it in February of 2013. That same month I stopped being an entrepreneur and went back to work for a company that made me extremely uncomfortable for 7 months. In August of 2013 I switched jobs and began working on Outure and everyday I take a little step forward by posting a picture to Instagram or commenting on Facebook or tweeting on Twitter. I hired a VA in November to help write reviews of urban activity equipment sold on Amazon as an affiliate, but hope to one day open my own e-commerce store. That’s my vision and this is my reality.