I consider myself a positive person and am always thinking optimistically about the future. At the same time, however, I am filled with a constant level of self-doubt.

Recently, I went to the doctor to get a check-up. It was my first check-up in over eight years. My prognosis was perfect, to which the doctor said,

“Of course it is, you exercise every day, do yoga, meditate, eat a vegetarian diet, and all around take really good care of your self. Why would you doubt your health?”

I still pushed him to tell me what more I could do, because something inside me didn’t allow me to believe I’m doing the best I could with my health. I know I could eat a lot more greens than I do, eat more fruits, exercise more…enter my self-doubt.

This self-doubt extends to everything in my life. I don’t think I’m doing enough for my business to grow it as fast as I want, even if I actually am. I don’t think I’m doing enough to keep my marriage healthy and happy, even if I actually am. I don’t think I’m doing enough to connect with close friends and family, even if I actually am…and on and on.

So where does it comes from?

Part of being an entrepreneur is to perpetually be at the beginning stages of new learning curves, and thus I think I’ve trained myself to always think I’m a beginner and there is always room for improvement. In addition, as the leader of a team, verses an employee, I hand out praise to others, but rarely does praise come back to me. It’s just the nature of the dynamic between a boss and employee. But couple the lack of external acknowledgment, with me always thinking I’m a beginner, and now I can start to see why I’m living in a state of self-doubt.

But I differ from many other people who live in the same self-doubt world, because for me, the self-doubt is a motivator, not a limiter. I use my self-doubt to challenge myself to do five extra push-ups and make one extra sales call because, in my mind, that’s what it takes to move past the beginner stage of the learning curve.

When it comes to marketing and selling, I’m happy to be known as an expert, but when it comes to self-growth, I want to constantly feel like I’m an amateur playing in the expert league.

(got this text from a friend today, but I haven’t responded yet because I don’t think I can accurately answer via text)

It’s such an innocent question, but yet can be so loaded based on the depth of my desire to answer.

Running a business really is a non-stop roller coaster of emotions. One day the sun is out and unicorns are marching along to a happy tune. The next day the world might as well come to an end as everything is ruined. It seems a bit dramatic, but really the swings are crazy in growing a business and can happen over the span of a few weeks, a few days, or sometimes even within the same day. I feel like I’m in a constant sensory overload.

One of the most valuable skills I learned over the years is the ability to manage my emotions and not get wrapped up in the swings. I’m also really good at putting things in perspective, because really at the end of the day, I still have my mental and physical health, with a great wife, and a roof over my head…see, now everything is better again .

On the worst days, all I want to do is rant about it to people (employees, customers, investors, Annie, etc), but many times that’s not possible because I have to keep the positive image for the sake of the company. Also, not everyone is built to deal with such swings and thus it’s not fair to dump on them because they might deal with it in a much worse way than me.

Today I walked to pick up Annie and thought about listening to a podcast on the way, but there was so much noise in my head that I needed to sort out, that I opted to walk in silence. I needed the walk to help me sort through my own thoughts. Taking walks really puts me at peace which explains why, rain or shine, I try and walk every day.

I wish I could say that such situations aren’t normal, but really I think every day I need some time, usually at the end of the day, to just white balance myself. Writing on this blog and mediation in the morning both help, but on the bad days, even all the skills I’ve built up over the years of being an entrepreneur aren’t able to help me cope. The stress is constant and usually coming at me from five different directions. It’s like I’m in a state of perpetual growth and challenge.

A friend of mine, Gary Tuerack, was the first person to tell me about the Entrepreneur’s Organization (EO) as a support group for people who have built businesses from the ground up. He didn’t just talk about it, he raved. So once my previous company, Red Rover, was qualified, I jumped in and joined EO.

EO is a non-profit and totally volunteer run. Fellow members told me that for every hour I put in, I’d get two back in many areas of my life. So, trusting their words, I quickly got involved in the leadership levels of EO. First as a Moderator for my Forum, then as a member of the NY board.

Three years later, I can say wholeheartedly that for every hour I put into EO, I’m easily getting two hours back. From business strategy, to personal development, to once in a lifetime experiences, EO truly has lived up to its hype.

I want to keep expanding my leadership experience within EO and the next level was to accept a nomination to become the President Elect Elect for the NY chapter. Three people, in total, were nominated this year, which I was excited about because I didn’t want to get the position by default, but rather by merit. I wanted to get the position because the board thought I was the right person at the right time.

After giving my speech to the board tonight, and them making me sweat it out a bit, I was officially voted in as the President Elect Elect! Not only was I voted in, it was a unanimous vote. Even someone else who was nominated, voted for me.

It’s a real honor and something I’m super excited about doing as EONY is the largest chapter in the world in an organization that is filled with almost 100,000 top notch entrepreneurs from around the world!

It’s also a lot of work, so the clock is ticking from now until I officially take my seat to set everything up in my life to be able to give my all to the role and gain the most value out of it as possible.

Several weeks ago, a student from Baldwin-Wallace College, Drew Thomas, asked, after a training I did at their school, if he could interview me for a class project. Today we conducted the interview while I was driving between Houston and Lake Charles. Here’s the list of questions he asked with some of my answers…

How did you get into this field or job?
I’m working on a longer post about this, but the short answer is a speaker, Patrick Combs, came to my school, College of Dupage, and inspired me. Around the same time, I won an academic award, All-USA Academic First Team, and was asked to tour around other community colleges in IL and tell my story. One school paid me a $50 honorarium. Then I saved up $2000 and attended a conference, APCA, where speakers go to get booked on the college market. It was a train wreck. So I went and worked for SuperCamp for three years to beef up my facilitation and speaking skills. While there I met Kevin Prentiss, who because my partner in Swift Kick. We built our Dance Floor Theory program, and came back to the market and it took off like wildfire. The rest, as they say, is history .

What do you enjoy most about your position?
Seeing students discover themselves and their passion through co-curricular activities.

What parts of your work are your least favorite, and why?
Rushing from one place to another while on the road. Taking one flight, to one rental car, to one hotel is fine, but doing that 100+ times per year can be exhausting.

What is your educational background?
B.A. in Business Management from Aurora University. The intangible skills I learned in college (time management, confidence, creativity, etc) I use far more than the tangible skills I learned (accounting, economics, etc).

What is a typical work day/week like?
Every day/week is different. I really don’t have a typical week. There are also travel days vs non-travel days. There really isn’t a normal day. I do however like to keep the same morning/night routine. In the morning, I wake up and drink a big glass of water, then do a combination of stretching, yoga, meditation, and pushups for 15 minutes. At night, I like to do a quick reflective journal on the day as well as set up my top 3 most important projects to get done for the next day.

What are the responsibilities in your position?
Everything. I’m serious, at this stage of a company I really keep a hand in just about everything. I have a team of two programmers who work on Student Launcher every third month, one full time assistant, and a part time community manager. It’s been said that the three most important things a CEO should do are to set the right strategy, hire the right team and support them to make the strategy happen, and make sure there’s enough money in the bank to make it all happen. I suppose I do that, while also taking the garbage out.

What can a person do to prepare to enter this field?
Whew. Honestly I don’t think someone can prepare to be an entrepreneur and start something from nothing. The learning happens as you go. As for professional speaking, the best thing to do is get training. Great speakers got great training to be great.

What is the work environment like?
My team is all virtual right now, so the work is done with a constant set of check-ins over daily, weekly, monthly, and yearly goals.

What are some of the problems you deal with on a day-to-day basis?
Cash flow is always on the top of my mind. How can I get everything done with limited resources. Specifically with spreading and growing Student Launcher.

What are the challenges you face with regards to communication in your job?
Since we are a virtual team and I’m often on the road, communication is key. Skype, IM, Email, and Texting are critical to our work flow and communication.

What kind of future is there for this type of job or industry?
As school budgets go down and academia is tightening the spending belt, fundraising will continue to go up, so Student Launcher is in a great spot. As for speaking, the requirements for assessment are increasing and thus speakers have to prove the value they give to a school, which I think is great as it weeds out the bad speakers.

What social, political and economic trends influence this field of work?
As I said above, smaller education budgets and requirements for assessment.

If you had it to do over again, is there anything you would do differently?
Hmmm, I would have grown our speaking business a bit longer before starting Red Rover. We were just starting to hit it big when Kevin and I opted to use our resources (time and money) to build Red Rover. Had we kept going with speaking a bit longer, I bet we could’ve built an amazing foundation from which to built out from.

What is the best advice you can give a person interested in this occupation?
As Nike says, “Just Do It!”

While presenting at the NCSL conference a few weeks ago, a fellow speaker friend reflected on how lucky we were to be able to do what we do. After a moment of processing, I shot back that I didn’t think luck had anything to do with it. I knew what he was trying to convey, but it isn’t about luck, it’s about hard work and dedication. In fact, crediting our success to luck actually serves as a disservice to all the students who look up to us. Because unlike hard work and dedication, luck isn’t a repeatable action that someone can copy. It makes my success seem like it happened to me, when in reality I made it happen. It wasn’t easy, and it still isn’t easy, but through hard work and dedication, I’ll continue to be the “luckiest” person in the world!

hat tip: Jonathan Hall

Blind Optimism:

“Huh, the sun isn’t out today. That’s ok, because I know it’ll be out by the end of the week.”

Determined Optimism:

“Huh, the sun isn’t out today. That’s ok, because I know it’ll be out by the end of the week, because I’m going to finish building my anti-cloud machine to make sure it happens.” 

Don’t confuse blind optimism and determined optimism. One will put you in the back seat and continuously set you up for disappointment and the other will put you in the driver’s seat so you determine your fate.

Six weeks ago the New York State Workers’ Compensation Board sent me a letter stating that I was in violation of their employee worker comp laws and thus fined a $10,000 penalty. I didn’t think I was in violation, but worried that I just forgot to file/pay for something and was thus actually in violation.

The Board gives you the option to petition the penalty in writing, but they warn you that the decision after the petition is final and can’t be changed. So I submitted and waited…and waited….and waited. Then finally received this letter from them a couple days ago:

Seeing the $10,000 fine go down to $0 was/is a great feeling. But this isn’t the first time I’ve dodged a business legal bullet. It’s not that I’m not on top of things, it’s just that there are SO many things to be on top of that, undoubtedly, something unintentionally slips through the cracks. My hope is that it’s a $10 mistake vs a $10,000 mistake.

Building something that people are willing to pay for is hard enough, but adding on layers and layers of legal stuff (State, Federal, IRS, Workers’ Comp, Insurance, etc) makes the job that much harder. Sure it can be outsourced (which for some I do), but that involves extra money that often times isn’t around, so you end up having to do it yourself.

“Pixar has been a marathon, not a sprint. There are times when you run a marathon and you wonder, Why am I doing this? But you take a drink of water, and around the next bend, you get your wind back, remember the finish line, and keep going. Fortunately, my training has been in doing things that take a long time. You know? I was at Apple 10 years. I would have preferred to be there the rest of my life. So I’m a long-term kind of person. I have been trained to think in units of time that are measured in several years. With what I’ve chosen to do with my life, you know, even a small thing takes a few years. To do anything of magnitude takes at least five years, more likely seven or eight. Rightfully or wrongfully, that’s how I think.” – Steve Jobs 1995

My first business was selling old edition textbooks online through a company called DiscountedDepot. It was very lucerative for me until the bookstores, I contracted with, realized they could do the same thing and cut me out. I really enjoyed growing the business, but I also really enjoyed growing my knowledge about how to grow a business. This was the first time I realized I had a love for not only the team (DiscountedDepot), but also for the game (business).

When Kevin and I started Swift Kick to do college leadership trainings, we got excited every time a new school booked us. In four years, we grew Swift Kick to be one of the top leadership training programs in the country and were voted top speakers on the college market for three years in a row. We loved seeing Swift Kick (the team) grow, but we also loved dissecting the game (college speaking).

My love for the team and game spreads beyond just business.

When I got engaged to ACbert, I started asking everyone around me, with marriage experience, what advice they’d give me as a male going into a marriage. Then, when we actually got married on Feb 5th, 2009, I continued to ask that question. In love, just like my textbook selling business, I’m extremely passionate about not only increasing the success of our marriage, but also about growing my understanding of what ‘love’ is. Once again I have a love for the team (me and ACbert) and for the game (love).

My knowledge hungry approach for the team and the game continues to stay with me as I ramp up Student Launcher. The better I understand the game, the more successful I can make the team.