5 Ways Entrepreneurship Is Like a Demanding Professor

Rusty Shelton, an Entrepreneurs’ Organization (EO) member from Austin, is president of Advantage Marketing and co-author of Mastering the New Media Landscape: Embrace the Micromedia Landscape. We asked Rusty about what he has learned during his entrepreneurial journey – here’s what he had to say.

Entrepreneurship is a lot like a demanding professor: She can be unfair and will ask more of you than just about any other challenge life has thrown your way. Yet somehow, more people want to take her course than ever before. Her classroom is a revolving door– she flunks would-be entrepreneurs without a second thought if they run out of tuition money or don’t pay attention in class. But for those who manage to hang on to their seat, she’ll teach some of life’s greatest lessons and reward engagement, innovation and hard work with a level of fulfillment that goes unrivaled.

I just wrapped up my first run through her “class” when my agency, Shelton Interactive, was acquired earlier this year by Advantage Media Group. I’m proud to join the Advantage Family and look forward to many great years ahead, but I learned a lot that I hope can help future students of entrepreneurship. Let me start by stating the obvious– signing up for this “entrepreneurial course” is a very scary thing to do. We hear stories from castaway students about long hours, missed opportunities and even bankruptcy, and we get nervous about signing up.

I remember staring at the ceiling many a night going back and forth on the decision to start my company. It felt risky and selfish to make the jump at the time. I had a good job and was doing well enough that my wife, Paige, could stay home with our infant sons, which was a big goal for us when we decided to have kids. Paige had far more courage than I did about it, and she would encourage me by saying, “What’s the worst thing that could happen? If it doesn’t work, we’re going to be fine.” I knew in my gut that was true, but I was scared to death to jump out and start the company.

Here are some lessons I learned after I jumped:

Fear is the biggest road block for would-be entrepreneurs, and you must be self-aware of that reality. As one of our clients, Jon Acuff, says, you have to be willing to “punch fear in the face.” For a long time I wasn’t ready to throw that punch. There are some good things about fear. It can prevent us from doing stupid things, and I had good reason to be scared of what would happen if it didn’t work. My biggest fear was knowing that if I failed, the boys were headed to daycare because both Paige and I were going back to work. So I talked myself out of it month after month. We had less than US$8,000 in the bank. We had a new mortgage, college funds, car payments and diapers to buy. We were comfortable, and I didn’t want to rock the boat. I was also afraid I couldn’t do it, that I wasn’t ready for the course– but my wife encouraged me to get over that fear and make the jump.

Oftentimes, wisdom, insight and encouragement will be the things that give you the confidence to start your business. Surround yourself with people who can provide that support for you. On 1 July, 2010, Shelton Interactive was launched to zero fanfare or media attention. I would love to tell you that it was a success from the start, but those first two months I was a case study for how not to start a business well. In the first month, I was defrauded of US$4,000 of the first US$6,000 in the corporate bank account. As if that wasn’t enough, each of my first two part-time employees quit within three weeks of me starting the business. I think neither thought anything was going to come of Shelton Interactive, and I had a hard time arguing my case at the time.

Be prepared for everything to go wrong in the first few months, and use it as fuel for the long hours needed to be successful. Don’t drop the course! I think my wife quickly realized that getting my business going was going to be way more work than we both thought. I was working 60-70 hour weeks, and she had to step up in so many ways with the boys. It was very hard on her, but we “studied” together and got through it, coming out stronger than ever before.

The course is so much easier when you are on the same page with your spouse or partner, and can tackle it as a team. What was counter-intuitive for me was that the early challenges didn’t discourage me; they fueled a competitive fire to hustle more to prove the naysayers wrong and those who believed in me from the start. I didn’t want to fail this course, and I knew we would pull out of it … we soon did, thanks to help from friends. We were off to the races, not due to what I had accomplished (screwing up was the only thing I had done well in those early months); rather, it was thanks to the help of good friends and, most importantly, an awesome team at the agency.

As a young company, it’s impossible to hang onto great talent if you don’t commit to making great culture the central foundation for the business. As Peter Drucker says, “Culture eats strategy for lunch,” and every bit of attention we paid to our culture paid off in spades. It’s surreal to sit back and think about all that was put in by so many to get me through one of life’s toughest courses. It’s taught by a tough professor, but this journey, which I almost talked myself out of beginning, came to be one of the greatest joys of my life.