Learn From My Entrepreneurial Mistakes

I’ve been an entrepreneur for as long as I can remember. I was selling lemonade the minute I learned about money. I always had a strong thirst for freedom and was constantly looking for ways to manifest it.

I launched my first official business venture, Green Lawn Care, Inc., when I was 15 years old. By the time I was a senior in high school, I employed my brother and a handful of friends to help with the workload.

But just because I got an early start on entrepreneurship didn’t mean early success. Being young, brave, bullheaded, and naive, I tended to do things the hard way.

I made every mistake imaginable, but my stubbornness kept me going. Lucky for you, my mistakes mean that you don’t have to go through the pain that I did. (That’s if you decide to learn from them.)

Lesson 1 :: Business is Business

When I went off to college, I made a deal with one of my best friends in order to help him pay for college. I lent him the company truck and gave him some of the accounts that I didn’t sell. He didn’t have a car or money and this way he could work to get back on his feet.

Since he was a good friend, I didn’t bother to write the agreement down or emphasize my expectations. I figured our friendship would be good enough.

Anyone who has been to college knows that the first semester of your freshman year is an exciting and overwhelming time. I was busy (school, fun, etc.)and only spoke to him about once a month. He assured me that everything was going as planned, and his word was good enough for me.

I went back home for Christmas break and was finally able to relax. I decided to make a visit to my old friend and check up on my truck.

To make a long story short, it turned out that he wasn’t the friend I thought he was. He had abandoned the accounts, dropped out of school, and wasn’t working period. He had taken to a life of partying and running around in the truck that I had entrusted to him.

I took the keys to my truck and drove away, never to speak to him again.

Lesson Learned

The lesson I learned from this experience was to always treat business as business, especially when it involves your friends. Write agreements down, hold people accountable, and don’t try to fix someone else’s life with your business.

Compartmentalize Your Money

In college, my entrepreneurial choice was T-shirts. I started a custom T-Shirt company where I designed and delivered T-shirts to various college organizations. I quickly became the go-to man on campus for T-shirts.

Most who have been to college, leave with a closet full of T-shirts. College kids love to commemorate every event they attend with a custom T-shirt.

I would design the shirt on my computer and then pass it off to my screen-printing partner. After the printing was finished, I picked up the boxes and delivered the shirts. I usually made a few bucks a shirt and each party sold 20 to 50 shirts.

I once figured that I had delivered over 20,000 T-shirts over my career as the campus T-shirt guy. My peers looked up to me as a go-getter. I was constantly busy, almost to the point of missing out on my college experience.

Any outsider would expect me to be making a ton of money, and according to my books, I was doing pretty good. The problem was, I didn’t know where any of it was going.

Lesson Learned

Since I’d never bothered to open up a separate business checking account, I never compartmentalized my money physically or mentally.

At the time, I didn’t see the rush. I thought “money’s money, right?”

I was spending my business money right along with my regular money and somehow I spent it all, which isn’t too hard as a college student.

The Power of Leverage

Not only did I have nothing to show for my labor, the labor I put into each order was immense. I was acting as the salesman, the designer, the account manager, the delivery guy, and the customer service representative for each order.

Although I looked extremely successful, I was pretty miserable. Once I shipped the T-shirts and collected my check for a few hundred dollars, my income stream was cut off. All of the creative power I had put into that project was now put to rest. If I wanted to make more money, I would have to recreate the process all over again.

I became a slave to that job. Just because I owned the company didn’t mean that I didn’t have a job.

Lesson Learned

I soon realized that I had picked the wrong marketing strategy for my business. Since I was doing custom work, I was forced to re-invent the wheel over and over again.

Since I was trading my time for dollars, I was still working a job.

I vowed from that day forward never to start a business that didn’t have a passive component.

A passive component means that the hard work you do once yields dividends over and over again while you spend your time finding new streams of income.

Just Say No

After I graduated, my brother and I started a “dot com.” Our idea was to make a website where a user could customize their own motivational poster. We would offer a number of photos, quotes, borders, and colors; leaving the decisions up to the consumers. (see an archived version of our site here)

I rushed out and bought a bunch of computer equipment, printers, cameras, etc. I put it all on my credit cards with the promise that we would easily make our money back. I exercised no restraint at all when it came to expenses.

Lesson learned

Our business never got off the ground and I was left with a pile of debt. I could have produced the same website without all the crazy equipment. Plus, it would have been perfectly reasonable to rent or sub-contract some of those functions until our system was proven.

Now, I am very weary about debt. I make myself prove an idea’s worth.

15 Years Later

The businesses I run today are much less stressful. I start small and build as I go. I look for marketing plans heavy on the passive side. All of my businesses are profitable. The best part is… I have a life to go along with it.