The thing about failing, is that if you didn’t start on day one..you have already failed.

At the end of my Sophomore year at The University of Iowa I found myself in the midst of a personal struggle. I was taking electives to fulfill an education in business, and I never understood that. I was filling in classes I could give two shits about so I could focus only on what I knew my brain was wired to do: build. This is why today, many entrepreneurs drop out of college. It’s not challenging when you are wasting young minds.

My brother, sister and I were fortunate enough to have the full support of our parents who paid all of our expenses during college. Tuition. Money to live on for apartments/condo’s. Charge cards for lunches and other things you could purchase at the Memorial Union. I knew I had to press ahead through this struggle because of the unbelievable support and I got lucky. Around this same time, the John Pappajohn Entrepreneurial Center (JPEC) started at The University of Iowa. Finally, a resource I could use.

I switched out of the business school to the liberal arts and began my last two years of studying economics/business administration and working towards my certificate of entrepreneurship through JPEC. Looking back on it, a certificate is a funny way to give credit for the way your brain is wired.

Because of the struggles I found during my first two years in college, I had an idea. An online portal to simplify communication between professors and students. I spent the entire summer after Sophomore year building a business plan. About 3 months later, while reading the Wall Street Journal (geek out college kid!), I learned of a company called Blackboard. Doing. The. Same. Thing. I had never heard of Blackboard, but they were building almost the exact same product as I had in my business plan and received press for raising a large round of funding. I knew then, I had passion for solving problems. I knew then, I was an entrepreneur.

Upon graduation, I moved back to Des Moines to start working for several of our family businesses. At the time, my father was running a prepaid calling card company called Dynamic Telecard. I came on board as a Financial Analyst, which really was a fancy word for making sure the calling cards we were selling were not losing money. And we got lucky. After about 4 years we had gained enough traction to be purchased for $10mil by a publicaly traded company. I knew then, building a company, finding strategic opportunities and solving consumer problems — ultimately lead to the best part of being an entrepreneur — an exit.

Fast forward to where I am today as the Co-Founder/CEO of Goodsmiths, I have failed at building 5 different Internet companies. Each of which I learned and made myself a better entrepreneur. And the bottom line, is that in all of these businesses — I have learned more than I could have ever imagined as a 34 year old.

Companies & Lessons Learned

• Prepaid Tele-Solutions was a company I started during my time at Dynamic Telecard. We didn’t have a way for people to refill calling cards online. So I built it. Lesson learned: online fraud is insane. We had people refilling cards with stolen credit cards. Using all the minutes (which cost us money), then the chargebacks..sometimes $20+. Brutal online fraud lesson. Shut it down immediately.
• FilmFitti was a company I started shortly after YouTube launched. I kept getting the same videos emailed to me from friends of dogs doing stupid human tricks. Soon I noticed these videos were receiving crazy amounts of views..millions within a few days. However, the content provider wasn’t making any money. So I built a website that gave advertising space next to a user generated video to the content provider, filed a patent and then boom..Youtube was purchased by Google. Took them a while, but now obviously content providers are making money on Youtube. Tons of it.
• Twittad was a company I started shortly after learning and joining Twitter. Much in the same way I saw Youtube not providing monetization, Twitter users couldn’t make any money off their reach. We used the open Twitter API to build Twittad, filed a patent and a trademark. We got somewhat lucky here, which I can’t discuss. Legal.
• GeoClip.it was a company I started while running a consulting company called Eliason Media for advertising agencies who do not have backend development teams. GeoClip.it was created as a mobile application to deliver nearby coupons to people who opt-in after sending a Tweet with a location attached, or a Facebook update with location. Again, filed for a patent. We built a relationship with Yellowbook to distribute over 150k coupons from their customers into our mobile application, but we couldn’t reach the all important metric: user downloads. That, and our partnership with Yellowbook proved to be a unlucky bet that they would be interested in our technology.
• Gordilla was a company we built at Eliason Media that would aggregate daily deals from all of the available providers. Groupon, Living Social, etc, etc. There were literally hundreds of these companies popping up everywhere giving you deals on nail salons when you are a dude. We thought there should be a better solution, so we created it. Ultimately, the economics of the business didn’t make sense. The cost to acquire a user did not equal the revenue made on a purchase. Sometimes, below 1% on the transaction size.

Where I stand today, is because of these failures mentioned above. Where will these failures take me? I have no idea. But I know one thing: If I wouldn’t have started them, I wouldn’t be in the position I am today.

Keep building. If you happen to fail and you don’t get lucky. Pick up the pieces and fight. It’s the entrepreneurial way.