I suppose I’ve always had the “entrepreneurial spirit.” My first taste of being in business likely occurred prior to this, but the first time I *remember* really enjoying building my own business was in the fifth grade.

Little Thing #1

For Christmas, I had gotten a new handheld electronic game. I suspect that most readers here will not remember these, but the one I had gotten was the race car game. It was a game with a button that slid only left and right, the goal to be to dodge the oncoming LEDs with the LED you controlled with the slider. It was a simple game but fun. I brought it to school and started charging people .25 per game to play. I averaged $9.00 a day. That’s a lot to a fifth grader. I learned about profit and expenses (batteries do, after all, cost money). I learned about friendly competition when a friend of mine and classmate brought his electronic handheld football game to school and charged .50 per game. I learned about volume sales (my game would last about a minute or two whereas the football game lasted substantially longer). I also learned about charging what the market would bear (I couldn’t get .50 per game but I could do .25 all day long). And lastly, I learned about “The Man” and how something that is going so well can go away in the blink of an eye when the school, after about a month of my enterprise, decided that these games were too much of a distraction to “real learning” and shut both myself and my competitor down.

Little did the school know that I learned more with my business experience in that short time than I did my whole fifth grade year

(it was my worst experience in elementary school, yet one of my most formative). When all was said and done, though, I had made a couple hundred dollars from a game that cost about $40 (which I hadn’t even paid for). Not a bad return.

Little Thing #2

In High School economics class, we learned how the stock market worked. We split the class into several groups and formed “corporations.” The members of these corporations then bought stock with real money. This money went to buy product that we would sell to the student body over a period of a couple weeks. I had been asked to be a member of the one corporation due to a previous simulation in which I had almost successfully beaten another team by coordinating an uprising against them (the other team was far more powerful) by secretly putting several of the smaller, less powerful teams together to try to take out the big team. It almost worked. Almost.

This team asked me to be part of this new corporation because they were impressed. We decided that the thing we were going to sell to the student body was going to be candy. I invested $9.00 into the company. Of the members of this newly formed team, I invested the most. We talked about what types of candy to buy. It mostly involved peanut butter cups and skittles as I recall.

I don’t remember what the other corporations sold. It didn’t matter. It was not true competition because we each were exclusive with our products. During breaks, lunch, and after school, we all had our tables set up in the quad and sold our goods. Our corporation slaughtered all the others. It wasn’t even close.

At the end of it all, we determined the stock value based on costs of goods sold and profit left over. We sold our stocks for what they were worth. My $9.00 had turned into about $75.00 in the two weeks. I made, far and away, more money than anyone else in the class (and according to the teacher, more than anyone ever had in that simulation). Making money was easy, and it was what I was meant to do. Or so I thought.

Little Thing #3

Back to Fifth Grade. At the time, my best friend, Jack, had introduced me to Basic programming. My dad worked at a local University and as a result, the head of the Math & Computing Department granted me a student account on the mainframe (their department was right across from my dad’s “Modern Languages” Department). It was here that I learned that a simple Basic statement such as “10 goto 10” could actually take down a campus-wide system as these mainframes were really not built to do multi-tasking. The joy of an endless loop. I hate to admit that there were times that I would laugh maniacally as other students in the lab would start literally banging their keyboards because nothing was happening. To all of you, I most humbly and heartily apologize. I was a jerk. I blame Jack.

None the less, I had been bitten by the programming bug.

I expanded my knowledge beyond causing others brain damage for fun and actually started to program useful things. My dad hired me at .50 an hour (which I’m pretty sure came out of his own pocket) and I worked on programs that would quiz his students. It’s also probable that he did it to keep me out of trouble.

My brain wrapped itself around programming rather quickly and, as a general rule, every day after school, you’d find me back up in one of the University labs hacking away. It wasn’t a bad life. I liked it a lot. My favorite lab was the one right outside the server room. I got to know the students who kept the systems up. I remember when they got some new storage. I want to say it was a drive that could store 20 megabytes. It was literally as big (and heavy) as a washing machine. Oh. . . the good ol’ days.

Little Thing #4

I believe it was during the summer between Eighth Grade and Ninth Grade (circa 1980-81) that a representative from a company called Commodore came and demonstrated this great new personal computer. It was better than a TRS80 and far more affordable than the Apple ][. It had color and a whopping 5 KB of RAM. That is pretty impressive. All you needed to do was hook it up to your TV. I don’t remember what I paid for it, but I knew this was the machine for me, so I ponied up with my hard-earned money for the computer that looked like nothing more than a keyboard and a tape drive. Before I knew it (well . . . four to six weeks later), I was a programming fool from the comfort of my own home. I could get used to this. It was a few months later that I had saved up enough for a 300 baud modem (If you don’t know what 300 baud is, let me explain: It’s SLOW) and learned how I could hook up to my account at the college. It was my first taste of remote work and I knew that, one day, it was going to be the life I’d be living. The world would just have to catch up (ya, I was just a scosche cocky back then).

A year later, I upgraded to a Commodore 64 and purchased my first Commodore 1541 5.25” floppy drive. I learned about sprite graphics and created a game based on the Saturday Night Live character, “Mr. Bill.” The game totally sucked, but suffice it to say, Mr. Bill died a LOT at the hands of Sluggo. A LOT.

Little Thing #5

Between my Junior and Senior years of high school, I was going to take a trip to Europe. I knew that Europe was no place to take my computers, and what I really needed was to make memories. I had always envied my sister’s camera and decided that it was time for me to dive into 35mm photography, so I sold my whole computer setup and purchased my first 35mm camera; a Canon AE1-Program with a couple of lenses and some books and accessories. I quickly learned how to actually use the thing and gained a basic understanding of the math behind the exposure you want. During that trip, I shot as many rolls of film as I could afford and discovered that maybe a life in photography was what I really wanted.

I came back, my senior year, where I was the head photographer for the yearbook. I was rather proud of that yearbook and I put a lot of time and effort into it. So much so, that the yearbook staff felt obligated to give me an award. As mentioned earlier, in my younger years, I was sort of a jerk, so I cannot remember what the award was. At the time it meant a lot to me, though.

I loved photography and I loved technology. If only there was some way to combine photography with technology. . . Maybe one day.

Little Thing #6

After high school, I went to about one semester of College. I say, “about,” because I think the only class I regularly attended was the photography class I was taking. I really enjoyed the class and the teacher. But most of all, I enjoyed the full access to the dark room where I was the head know-it-all and all the other students came to me for assistance. My ego was riding pretty high around that time.

Little Thing #7

After deciding to drop out of college (much to the chagrin of my dad – did I mention he was a University Professor?), I knew I needed to make money. I applied for (and got) a job with a company called Lifetouch National School Studios. Many of you might be familiar with this company. They specialize in school photography. I worked there for two school years, the first being an assistant and general runner and then the next year I did a lot of darkroom work. I was in my zone. I got to be good friends with a guy named Gene who was the world’s biggest Raiders fan and even got me a press pass a couple years later to shoot from the sidelines.

During that game, I met people like Howie Long, Bo Jackson and Bob Golic.

I also met James Garner who got to stand by the bench because, well, he was James Garner. Incidentally, he was exactly what you’d have expected him to be. Gene also introduced me to the world of Santa Claus mall photography; possibly the worst job I ever had. No, I was not the Santa. I was the photographer. The problem was never the kids. It was always the parents. You try telling parents that their kid is hysterical, will never calm down, and will never smile for Santa because he or she is scared to death of the man with the beard. Or, maybe, try to find something to clean up the pee on the floor because some parent made their kid wait in line for two hours while he had to go to the bathroom (usually the two hours was because of a number of the aforementioned parents living in their dreamland of a smiling child). Or, having a parent make you tell their child that Santa has gone home for the day (because the parents waited until after the mall closed before they decided to get in line). All true stories. Ya – I only did it one Christmas. Ironically, I lasted longer than most.

Little Thing #8

I quickly realized that I needed to be making more money and that commissioned sales was where I needed to be. I applied for (and got) a job at a company called Circuit City. They sold electronics of all sorts. I originally wanted to work in their Camera Department, only to discover that they didn’t have one. So, it was Small Electronics for me, where I quickly became Assistant Manager of the department.

After cutting my teeth in electronics, I figured out that where I really wanted to be was in the Video Department. It’s where the money was. So I put in for a transfer and that’s where I got to be good friends with Gregg Franklin. Gregg and I forged a strong friendship and discovered that neither one of us ever really had a desire to work for “The Man,” so we decided to look for business opportunities. This was around 1987 or 1988.

Little Thing #9

In 1989, Gregg and I decided to venture off from Circuit City and we bought a little camera store for $10,000.00. It had been around for a while and, honestly, neither one of us did much due diligence. Had we done so, we would have discovered the reputation the owner of the store had. We spent the next two years working on re-branding, building up a local reputation of supporting schools and professional photographers in the area, and eventually became a reputable business in town. The local photographers would come and chat for hours on end with us and we became friends with many who remain our friends to this day. During this time, we built a darkroom and did a lot of custom work.

Additionally, a friend from school had started his own company in which he built custom PCs. It was time for me to return to the world of computing, where, after purchasing an XT PC running MS-DOS 2.0 (I believe), and a piece of database software called Q&A, I developed a fully operational Point of Sale system. It was my first foray into data mining. I had finally figured out a way to combine my love of photography with my love for computing. It wasn’t what I initially imagined, but it would do.

During the time of the camera store, I also started my own WWIV BBS called “The Dragon’s Tavern”, a precursor to the Internet. It had software and games (can you say, “Global Thermal Nuclear War?). At one point, I was the only one in the area with a BBS and ONE GIG of storage space. Modem tech had advanced and I got myself a USRobotics 14.4 Courier HST modem. I was the king of the local BBS world. WWIV was an open source BBS platform and I spent a lot of time writing mods for it in Turbo C++. I met people from all over the world and spent hours on the phone with some of them as we worked through programming issues and ideas. It was my first experience with remote collaboration.

The camera store lasted a couple of years, but we suffered a bit from trying to do too much too fast, along with a failing economy, and we realized that our model was not really sustainable. Rather than getting buried under a mountain of debt, we made the choice to shut the place down.

From there Gregg and I tried our hands at a few things, the most significant being a sign company (we had actually been running it as a side business from the camera story for some time, to help bolster our income). To be honest, I didn’t like that job that much. Gregg got to have all the fun doing the creative work, then he, our alcoholic partner who showed us the ropes, and myself would go and install them. Vinyl cutting was fun and the tech behind it still fascinates me, but it didn’t take long for us to learn that we were not the right fit with the third partner, so Gregg and I split from him.

Little Thing #10

Fast forward a couple years. Gregg and I had been doing our own things separately for a while, trying to find our place in life. Owning and shutting down a couple of businesses does make you realize that you’re not as perfect as you think you are and may even be a bit of cause for some soul searching. I cannot speak for Gregg, but I know that for myself, that was the case.

I was burnt out on photography.

Doing something for a couple of years for others and none for yourself sort of takes the passion out of it.

Running a free BBS was not exactly a business model that worked. I think it was around 1995 that I discovered Netcom. It was one of the first real internet providers. I bit. I was hooked. It was *like* a BBS but SO much more! The world had opened up to me and I saw my vision of one day becoming a remote worker come that much closer. Before long, a feeling had returned that I had not had in awhile: the desire to learn something new in technology. I wanted to gain an understanding of how the back end of this wondrous new tool worked. I knew it was the future, and it was within my grasp. It had been a while since I had been that excited about anything.

It was then that Gregg and I reconnected. Gregg had told me that some other mutual friends of ours were about to embark on starting a regional Internet Service Provider, servicing schools and running a digital technology called ISDN. They had invested in the equipment but needed someone to run it. They had asked Gregg, and when I expressed interest, we formed a partnership and got to work. During this time, I learned about routers, IP traffic, DNS, collaboration with people on a global level, scalability, building departments and efficiently servicing customers through no more than email and a telephone connection. I learned about the value of good documentation and I learned how to deal with big, huge companies and their lawyers. I learned all of these things and yet, I wouldn’t say that any of those shaped my future and my life and business operating philosophy more than the epiphany I had once I hired our first employee.

Until this point, I had always been about making money and a name for myself. It was ALWAYS about the money for me. Always. But I remember that moment like it was yesterday. That moment I looked at the empty desk of our first employee and realized that we were embarking on something great. We were building a company that would help sustain the lives of others and their families. If all went well, it wouldn’t be just a few. It would be many.

In the blink of an eye, it went from being about me and what I could take home, to being about them.

To being about us. All of us. That one moment changed everything for me.

Little (ok BIG) Thing #11

In 2003, my wife and I decided to move to Wisconsin from sunny Southern California. I was going to continue to work remotely with the ISP we had built up to over 40 employees and my wife Jessica was going to also work remotely with the Electronic Funds Transfer company she had worked to build up while in California (she was their first employee). Wisconsin was a nice break from the rat race of Southern California. We bought a house, set up our office and before I knew it, I discovered that the people back home at the ISP didn’t understand the concept of remote work. I was a shareholder of a company that had no use for me sitting a couple thousand miles away. Sure, from time to time they’d call me, but overall, out of sight meant out of mind where I was concerned.

We moved to a pretty small town where we were happy to have high speed internet, but there was not a lot of demand for a network engineer or software programmer. I had, once again, found myself somewhat without a professional purpose.

Soon after our first year there, we found out that Jessica was pregnant. Our main purpose in moving to Wisconsin was to start a family, but Jessica had always had issues carrying a pregnancy to full term. It was heartbreaking to deal with multiple miscarriages, but we had found a doctor in Green Bay (2.5 hours away) who thought he might be able to narrow down the issue. He was right, and nine months (and two weeks) later, we were introduced to our son, Eli. Hard to believe it’s been 11 years. And while I was struggling to find my place professionally, there was no doubt that I knew my place personally, as a father.

I was 38 and suddenly felt it was what I was meant to do.

I attempted to work for a local computer place during this time, but that simply didn’t take. I had, for a long time, said that employment may not be for me and certainly, in that situation, I was proven right. I am not, and never have been, a “Yes” man, I would tell people. I needed to reinvent myself and I needed to figure out my place.

This time put a lot of strain on my marriage to Jessica. She was the main bread winner and while she was appreciative of the fact that I was really good with taking care of Eli and doing things around the house, she felt the pressures of being responsible for the family’s financial well-being. “Just find something – anything,” she’d say. She wanted me to find something that made me happy. She knew that while I loved being a father, I also felt the pressure to contribute to our stability. I struggled. A lot.

Little Thing #12

During the short time that I worked for the computer company, we moved again. This time, we bought the home of one of the city’s founders. It was on the river and while the place needed work, it was on about 3 acres of land and was a pretty nice place. I had my eye on the house next to it which was a big Victorian (and at one point, part of the same property). It was owned by a couple of empty-nesters and I knew that owning the house we had just purchased would put us in a prime position to buy it when it became available. It was my five year plan.

Two years later, I was approached by our neighbor. We bought the house and moved in. We still had not been able to sell the first house that we bought and it was sitting empty. We were about to have two empty houses. I had been doing tech work as I could, but still was without a purpose. Fortunately, Jessica was still plugging away. Throughout it all, she was supportive of my desire to find something. I admit, there were those moments where I was just happy to be a dad (that’s my way of saying I might have gotten a little lazy looking for an income).

In the new house for a bit, I was talking to one of my friends back in California. He was going through some pretty major life changes and was looking for his own purpose. I remember asking him what he’d like to do and he said that he enjoyed going to motorcycle swap meets, buying parts and then selling them on Ebay. And just like that, a business was born. He needed a new start. I needed something to do – a way to make money. And I knew Ebay and tech really well. It seemed like a match made in heaven.We moved him into the empty first house that we had and ran the business out of that house for a while. We made contacts and started buying larger and larger lots, liquidating them almost as fast as we were getting them. We were starting to make a little bit of money, but we kept turning that money into bigger lots, which meant we needed more storage, which meant it was time to get office space. Our specialty was Harley Davidson parts and it only took a short time for me to go from only knowing that most Harleys had two wheels to being able to identify the part, year and bike it came from; to know its value; and to have an idea on its demand. I became a tougher negotiator and walked away from a deal or two that just didn’t feel right. The biker world was definitely a world I never imagined myself within, but I certainly, for the first time in my professional life, actually felt like I was part of a community.

Soon after we started that company, though, the company Jessica had been working for shut its doors, literally overnight. She was not making money, in an industry where there was no local demand, and I was trying to grow a company. For those wondering, that is not a sustainable personal financial model. The housing market crashed, and I was spending nights doing database patient record merging at the local hospital.

Before we knew it, we were flat broke. We literally lost almost everything.

The two empty houses were taken by the banks and we were just fighting to keep the house we were in. It was also about this time that Jessica announced that she was pregnant with Brenna. It was the only good news we had at the time. I was 42 and, for the first time in my adult life, had to actually go to my parents and ask for help. I honestly don’t know where I’d be today if I didn’t have them.

The company we had was starting to see dwindling sales. When the economy crashes, people suddenly learn to live with that little ding in their gas tank or that other non-critical noise their bike may be making. Ebay started raising their fees and our business model became unsustainable.

Little Thing #13

With money quickly dwindling away in our bank account, I suddenly had this wonderful idea to start making money off of our competitors on Ebay. They had an affiliate program and I needed to figure out a way to leverage that. But how?

It was then that I discovered WordPress.

Like many, I had always thought of it as a blogging platform and nothing more. But then I discovered a plugin that would read in a feed from Ebay and worked within WordPress. It took me about an hour to set up a WordPress site and another minute to figure out how to install the plugin. The next two days was spent populating categories, and a little over a month later, I got my first direct deposit from Ebay. This could work. But even more importantly, for the first time, I saw that WordPress could be so much more than a blogging platform.

It wasn’t much longer before I was starting to develop websites for others. My design skills have always lacked, so to start, it was mostly out of the box themes, but as I got more seasoned, I learned more and more about the power of WordPress.

Eventually, we closed down the motorcycle liquidation business.

We tried our hand at running a Renaissance Faire booth (along with touring the country), but that, too, was not really sustainable.

I even drove a truck with staging equipment for Fox Sports a couple of times. Anything to pay the bills.

Little Thing #14

During one of my driving trips, I had been talking to Gregg. Turns out he had been doing WordPress development for a while and he was looking for some help. I was not a good designer, and I had barely dipped my feet into being a developer, but Gregg was willing to teach me everything he knew. Every morning, I’d wake up, Gregg and I would get on a call and he’d explain really cool ways to customize WordPress. We’d strip a theme down to the bones and build it up. We’d find frameworks and build them out. We’d bang our heads over CSS (something, I think, neither of us ever really were able to wrap our minds around), and we had work. Lots of work.

Though financially ruined, Jessica and I were finally starting to see some light.

I had finally found something I really liked and she had finally found herself with a position working for another company. We had lost all our homes except the one in which we lived and had depleted all our bank accounts and college funds, yet we were hopeful. We had our two kids, a roof over our heads and work which generated income.

Most of the work Gregg and I did was working with agencies. We liked it that way. Neither of us really enjoyed pounding pavement, so it was nice to have people who specialized in sales do that part of the lifting. But despite the fact that we were getting busier, we knew that we needed to work on passive income possibilities.

Little Thing #15

In 2012, Gregg brought up the idea of me going to WordCamp San Diego. Now, I hate conferences and conventions. This sounded to me about as far from fun as I could get. He offered to pay for the badge if I paid for my plane ticket. Not knowing *really* what a WordCamp was, I figured it was a fair deal. It was only after I spoke with Jessica about going that I realized the cost of the ticket. I tell people that I still feel like I got the better end of the deal.

That trip to WordCamp San Diego changed everything for me.

I had always believed that businesses could succeed while also being part of a community that supported and built each other up. For the first time in my adult life, I got to witness it first hand. I had a blast! WordCamp was not a conference, it was a sharing of ideas. It was not a convention, it was a place to build actual relationships. It was a business event, educational event, and social event all in one package. I knew I was in the right place (finally).

44 years old and I finally found my place.

But how could I actively participate? Part of being in a community is that desire and need to give back. I was green and hardly knew anything.

Little Thing #15(a)

One of the people I met while in San Diego in 2012 was Stephen Carroll. He had developed this really cool tool called DesktopServer; a tool Gregg and I used almost every day during our development days. Gregg was having an issue with a site we were building and Stephen offered to help us figure it out. I was blown away that someone would give up their time so freely with no interest in remuneration. He just wanted to help. Stephen and I spoke a little bit, but he mostly focused on helping Gregg get through the issue he had. He was kind and generous, and I liked him immediately.

Little Thing #16

In 2013 Gregg and I were working together on a project and, as often happened, the conversation turned back to what we could do for some passive income. He and I came up with an idea for a theme we wanted to build. It would be unlike anything anyone had seen. Robust, clean code, efficient. In other words, it was a theme that was above our skill levels, over our heads, and somewhat out of reach. We needed a developer with a skill that far exceeded our own. Gregg said it: “We need someone like Stephen.”

I totally agreed with Gregg and so the call was placed. Gregg was to get in touch with Steve and see if he’d be interested in helping us out. It was a good plan.

An hour later, Gregg called me back to let me know the result of the conversation. Steve was, indeed, anxious to work with us (if pressed slightly, I think he would tell you that he was anxious to work with Gregg since he only really knew me through Facebook). But what he wanted was for US to help HIM at ServerPress. He wanted to simply code while we handled the rest. I contacted him directly to ask him some questions, set up a path for the company under the new structure and the rest, as they say, is history.


This past June marked three years since we re-formed the company and it’s been a thrill ride to say the least. Since then, we’ve grown the company by over 400%, I’ve had the opportunity to travel the country and speak at several WordCamps (2014 saw me at over 20) and I actually look forward to Mondays every bit as much as I look forward to weekends. ServerPress, LLC is a company that’s respected within the WordPress Community, and it has afforded me the ability to help financially sustain my family.

In 2013 Jessica, Eli, Brenna, and I moved to Milwaukee where we bought an older home (117 years) with the purpose of restoring it, building it out (and up), and fostering to adopt sibling groups (you can read about it on my blog, http://twotofive.us).

We currently have six foster kids which puts us at a family of 10.

None of this would have been possible without all the little things, a couple of big things, and WordPress (the most important of which, is its Community).

While we’re still digging ourselves out of the mess of a few years ago, that light is getting brighter every day.

The post 16 Little Things That Grew Into Big Things (My Life in a Bunch of Words) appeared first on HeroPress.

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