Early Lessons From a Serial Entrepreneur
What’s common about entrepreneurs and what can we learn from them?
Business ownership can be both rewarding and daunting; however, it’s rarely boring. I’ve spoken to hundreds of entrepreneurs over the past twenty years, and most are driven by a common thread.
Yes, purpose and money are high on the list, but it goes deeper than this. I can relate to a lot of the stories I’ve heard because I’m also a business owner. I made the leap and have seen first hand the good and bad of starting and running a company.
Entrepreneurs come from all walks of life and backgrounds, but what do they have in common? Since one of the best ways to learn is through the experiences of others, I’ll share my short story which I’m sure is similar to many entrepreneurs. I hope you’re able to take away a few nuggets of wisdom.
In the Early Years
My entrepreneurial journey began when I was eight or nine. This was around the time I started selling Blow Pops at school for a quarter each in the hopes of buying the latest Transformer or G.I. Joe action figure. Blow Pops were cherished when I was growing up (lollipops wrapped around a chewy bubblegum interior — need I say more?).
I would buy a 20-count bag from the nearby gas station for a few bucks and resell them to sugar craving kids during recess. This fueled our days of dodgeball and excessive amounts of tag, which many times turned into wrestling matches. It was good money for a kid in the 80’s, allowing me to subsidize my $5 dollar per week allowance. It was sure easier than some of the chores my parents bestowed upon me.
Back then, we didn’t have the distraction of the Internet, and our choices on TV were limited. If you weren’t in front of the TV at a specific time, you never saw your favorite show again (until the reruns aired 20 years later). We watched commercials with patience because we didn’t have a choice. It really didn’t matter anyway because most of our time was spent outside doing what boys do from dawn till dusk or until our parents tracked us down.
As kids, we had an unbelievable amount of freedom to roam around and come up with little side hustles to make a few dollars. We explored excessively and sometimes found ourselves on the wrong side of luck. I didn’t realize this at the time, but I was learning at an early age the fundamentals of business and making money.
Find something in demand that people want, and sell it to them above cost — this sounds simple enough.
Another venture that I look back on with tribulation was jumping head first into golf course lakes to retrieve golf balls — probably not the best idea, given that I grew up in Florida (gators were considered neighborhood pets back then). I would sell the white ones for 25 cents, the orange ones for 50, and the yellow for 75 (I’m not sure why I priced it this way, but it made sense to me at the time). On occasion, a golfer would come by and offer me five bucks for the whole lot. I would quickly take the money, run to the gas station, and buy more Blow Pops. At least I had the foresight back then to weigh out risk and reward.
Making the Leap to Starting My First Real Business
Somewhere between the dot-com collapse and the invention of the iPhone and social media, I made the leap to start my first real business. The year was 2005, and it was a great time to be in the technology field. We had learned from the mistakes made just a few years earlier by overzealous entrepreneurs, but we were still on the cusp of technological breakthroughs.
At the time, I, like millions of other knowledge workers, was commuting to my 9:00–5:00 job, where I helped design software applications for complex commercial and government systems. It was meaningful work that I enjoyed doing, but there was always a lingering tension to do more, to rely on my capabilities and decision-making. These were the same feelings I had as a kid. I wondered if I could make it and if I had what it took to be successful on my own. I worried about the risks and the potential failure that might come.
Business ideas came and went on my commute, as quickly as the passing cars on the highway. I longed for the day I would be running my own company. The sense of freedom that came with owning a business had been a never-ending vision in my mind since those early days in Florida.
Entrepreneurs are driven by these feelings, a feeling of control and dependence on their own efforts.
Maybe these thoughts start at a young age, as they did for me, but become muted as we age and life sets in. Aspirational life goals came to fill the voids between business ideas as I inched closer to starting a business. After all, graduating from college, landing a job, meeting the woman of my dreams, and buying a house are all big goals worth pursuing. In many cases, these are the dreams of the parents who have their own motivations for making sure their children make it in life.
I had a loving wife and family and weekend hobbies that I enjoyed. We built our first house and spent countless hours decorating it. Things were good, so why did I continue having the itch to break out on my own? Why would anyone want to introduce risk and uncertainty into their life? Fear, after all, is something every entrepreneur faces at one time or another.
I had a friend when I was in my 20s that used to skydive on a weekly basis. He tried to get me to go on several occasions, but I valued land-dwelling too much. I asked him why he was drawn to it, why one would put oneself at risk unnecessarily. For him, it was the rush of the unknown and knowing that he could control his fate if he prepared, had the right equipment, and planned his jumps. This attitude crosses over into any number of risky endeavors. It’s similar to the theme I had as an entrepreneur, except I was less likely to die doing it, and the rush wasn’t as intense. Being an entrepreneur is a journey, just like anything else in life. It takes patience, hard work, determination, and courage to succeed and expose yourself to risk. I respected business owners and their willingness to take the leap.
Complacency is a Death Sentence
As I navigated through my professional life, I became distracted at times with how exactly to make the switch from a great paying job to the land of uncertainty that quickly follows new business ventures. Months would go by, and no momentum would be made; then there would be a spark of insight, maybe through something I read or a conversation I had. Life had become comfortable, and to a degree, I had become complacent.
Complacency is like a death sentence to an entrepreneur; before you know it, years have gone by as your business idea collects dust or is replicated, copied, and launched by someone else.
I came up with one idea called Tote-a-Tot that, at the time, I thought was brilliant. It was a child seat that would attach to a rolling suitcase. I was doing a lot of traveling at the time and thought this would be an excellent way for parents to confine their children and make it easier and safer for them to navigate through an airport. This was just one of a dozen different ideas I sat on for years. I performed patent research on the product and looked into manufacturing. I investigated the legal liability of such an idea. What would happen if a child got injured? How would the seat attach to different size suitcases? As I went deeper and deeper, I started to lose interest, and another idea surfaced.
The process of coming up with business ideas is exploratory. I would come up with one, perform market research, and talk to friends and family. I would bounce ideas off of acquaintances and pay close attention to their initial reactions. “Would you put your child in this seat?” I would ask.
Don’t be too married to one idea. There’s another one coming just around the corner.
I became highly efficient at iterating new ideas, which is critical for new entrepreneurs. I tried not to dwell too much on a single one. Giving equal weight to each and putting them through an evaluation process really helped me filter out good ideas from bad ones.
Just Get Started Already
There’s no question that becoming an entrepreneur can bring about discomfort and stress. You have to embrace and get comfortable with uncertainty. Looking back on my journey, it wasn’t so much about the financial reward; it had to do more with controlling my destiny and outcome. It had to do with safety and security — at least as a business owner, I had better insights into job security. I knew if I was going to make money or not. If not, I could always find another job, after all.
I’ve had several business failures over the years that I learned from, but I kept at it. The important thing is to jump in and get started. Find an idea you can realistically achieve and try to grow it on the side if you must. You don’t need to have a full business plan to get started — plans change. All of my businesses were started on the side, and this allowed me to reduce the risk and test out multiple ideas. Once I found one that worked and I knew I could make a living from it, I made the leap and haven’t looked back.
