I’ve Been Asking One Question, All Over the World

I’m incredibly passionate about startup ecosystems. In cities such as Ames, where more than half the population is in some way connected to the university, I started thinking critically about how one approaches entrepreneurship as a career choice. I believe choosing the path of entrepreneurship should carry a connotation as powerful as if one were to say they were to become a lawyer, or a doctor (how cliché of choices by me).

Since last October, I’ve been asking one question as often as possible, wherever I can.

How do you discuss and handle entrepreneurship as a career choice, when dealing with society and traditional education?

I’ve been fortunate enough to ask this question while attending the Startup Gathering across Ireland; while discussing startups in São Paulo, Brazil; while connecting with startup community builders on LinkedIn; while at entrepreneurial centers across Iowa; while at a recent business conference in Lincoln, Nebraska; while at the Iowa Startup Accelerator’s Ag and Food Innovation Summit; and yesterday, to Gary Vaynerchuck.

The responses have been awesome and full of wisdom beyond my years.

A few of my observations and thoughts are below.


Society pushes people to make early decisions on what their title will be. Especially here in the states, where we’re all to “Chase the American Dream.” We need to know NOW, what we’re doing. Otherwise we fall behind, and we can’t jump into going in high amounts of debt for that large house and fancy car.

Choosing entrepreneurship is going against all of this. The title, “entrepreneur,” sounds funny, because it’s too broad and can range from broke to billionaire. The American Dream becomes too messy and cloudy when working on your own path, because anxiety hits like a left hook upon your cheek bone, often forcing you to worry into quitting in order to find a “safer” path.


Traditional higher education’s system is not built to encourage or support entrepreneurship at a high enough level, in order to translate to high enough success rates. Traditional higher education will become less able to help in many areas, as we progress towards exponential technological times, and entirely reshaped industries. Education may look entirely different in five years. This is okay, as many people are capable of embracing change and then adapting.


No one wants to be continually pushed out of their comfort zone. Professors don’t want to put students on the spot, because that could warrant the next viral outrage. Public speaking is feared more than death. Life can be lived very comfortably from behind a “secure” job and all of the latest television shows (by the way, there will continue to be more and more shows, better and better options, until you die). Choosing the path of entrepreneurship at any age requires you to personally push yourself every step of the way, because no one else fully can for you.


When I left Iowa State in 2009 to play and coach poker full time, and when I left Denver to move to Dublin, to again play and coach poker full time in 2013, I had very little support. From the support I did have, the majority of it came from friends that are materialistic. This is due to how ESPN glorified poker by showing the profitable .001 percent of players winning piles of cash.

Education labeled me a failure and college dropout in 2009. Corporate America labeled me not able to cut it in 2013. Jumping into entrepreneurship will warrant similar labels, especially if you are young and in the middle of education and/or a career path. At times, it may be correct to finish your current focus, whether that is a degree or a contract. Far more often, though, there is no better time to switch paths than right now. Again, the world we live in is evolving faster than traditional education can provide for. If you’re waiting for the “right time,” you’ll be waiting the remainder of your life.


Traditional education is not the villain here. It is simply fighting for its survival. Educators, especially at higher levels, are comfortable and often respectable. Their earlier paths of hard work led them to where they are now. But now requires a majority set of new skills, adaptability, and the idea that one can discover over 90% of knowledge while sitting in front of a screen of pixels. Platforms like Udemy continue to cut into the physical world of traditional higher education. Yet college enrollment continues to rise, and more and more people are convinced they need to pursue a master’s degree, as a bachelor’s is becoming too common for job markets.


You don’t have to prove anything to anyone. Before you jump into the insecure waters of entrepreneurship with a business idea, you will likely ask your peers (often fellow students if you are younger) and those closest to you for advice. Remember, they’re closest to you now, because of your current path. If you change your path, you may lose touch and friendships. Those closest to you may have a subconscious reaction that will make them fight for their own survival in your life that both you and they don’t realize at the time. This is also incredibly difficult when dealing with parents. Parents want what is best for you, but that often leads to what they believe to be the safest and most comfortable route for you, in life. You need to have faith in your own decisions, in addition to having faith that your true friends and supportive parents will understand and accept your decisions. At some point in any journey, your decisions will lead to losing some amount of relationships. Again, this is okay.

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These are simply observations that have come about when asking my question in different settings, while on my travels within different communities. They may be right and/or wrong. These observations will affect every one of you reading this, differently.

As a note, I consume somewhere between 40–90 hours a week of hands-on entrepreneurial ventures that are of my own. I consume 15–50 hours a week of knowledge in the form of networking, reading, podcasts, interviews, and discussions with educators (there are more than a few that understand entrepreneurship as a careers choice here in Ames, and there are plenty throughout the world).

All of my entrepreneurial ventures and paths are meant to offer and create value for people. I simply want to build startups into sustainable companies, communities into fostering startup ecosystems, and higher education into a supporter of true innovation and creativity.

If you’ve made it to here and you think I’m crazy, that’s okay. I agree with you.