Gary Trauner

Gary Trauner

As I write this, six finalists are hard at work preparing for Silicon Couloir’s Pitch Day, and an integral part of their preparation has been intensely focused coaching sessions.

Most people think of entrepreneurship — starting and running one’s own business or venture — through a somewhat romanticized lens. Yes, intellectually they may know it takes long hours and hard work, but it seems the Hollywood view is of employees shooting Nerf hoops from a beanbag chair while somehow magically growing a business that makes millions.

The truth is much different than most who’ve never been entrepreneurs will ever know.

Entrepreneurship is not just hard work, long hours and daily stress over everything from finances to staffing to operations. It also tends to be an incredibly lonely undertaking by those willing to risk it all for their vision.

In the words of Teddy Roosevelt, “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena ... who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but … who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

Those words, while delivered by Roosevelt in the context of “Citizenship in a Republic,” apply just as well to entrepreneurship. Striving against odds to succeed, all while usually toiling in relative anonymity and bearing the burden mostly alone.

A quick parallel story: I’ve been both an entrepreneur (with success and failure — welcome to that world) and I’ve run for elected office at the federal level (sadly, at least for me, unsuccessfully).

In my first political campaign I ended up wide awake in bed at 3 in the morning on election night, behind by a mere few hundred votes out of several hundred thousand. With my spouse sleeping beside me I spent time on the phone with campaign staff, D.C. lawyers and D.C .officials working to figure out what we should do next.

As I listened in — mostly silent — a realization suddenly hit me: The true burden of that campaign was on me alone as the candidate. Not my family or friends or staff. Winning or losing was mine to own, and, as I now advise future candidates, make sure when you’re sitting in bed on election night you’ve run the race you want to run and done the things you want to do. No regrets.

My experience in entrepreneurship, while not quite so dramatic, follows a similar theme. When all is said and done, it is the entrepreneur on whom the burden of success or failure rests. Not staff or vendors or consultants or board members. Difficult decisions fall on the entrepreneur: when and how to raise money, how to grow, who to hire, when to cut back or lay people off (if necessary). The entrepreneur must live with his or her decisions in perpetuity.

And that’s where mentoring and coaching come into play. Successful entrepreneurs almost universally find someone or several people who help guide them along their journey.

The best and most effective coaches, or mentors, generally have several traits in common: (1) As expected, they likely had prior success in business or in starting a venture; (2) they have a desire to help others follow their path to success and are not looking for compensation or public visibility; and (3) the truly good mentors take the time to understand their mentee’s values, business model and ultimate goals before providing relevant advice and guidance.

Mentorship can take many forms. Silicon Couloir has followed a successful model in which each entrepreneur in the TEAMS program is assigned three mentor.” Regular meetings are scheduled to discuss ongoing and new issues encountered by the entrepreneur. Critical in this model is that while the mentors make suggestions and problem-solve with the entrepreneur, it’s the entrepreneur who must do the work.

Another key aspect of Silicon Couloir’s mentoring model is what I’ll call the “next go-round” concept. Unfortunately, most startups don’t succeed. So while mentors focus on coaching for the immediate venture, they are also working to impart expertise and experience to better prepare the entrepreneur for future efforts should the current one fail. Entrepreneurship is a unique undertaking, and TEAMS aims to increase the odds of success, both now and in the future.

The Tetons region is filled with people willing to risk it all in the arena. But they cannot do it alone. Finding and cultivating mentors or coaches — not usually something entrepreneurs put at the top of their list — can be the difference between failure and the “triumph of high achievement.”

Gary Trauner is the executive director of Silicon Couloir. Visionary Ventures runs once per month. Contact him at

Editor in Chief Johanna Love has covered the Jackson Hole community as part of the News&Guide staff since 1998. She took the helm of the newsroom in 2017. She fields story tips and kudos as well as criticism and questions.

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