I’m on My Sixth Company: Here’s Why I Still See Myself as an Underdog

I was pretty much destined to be an underdog. I grew up in a small town of under 5,000 people in rural, central Iowa. Whenever I traveled to urban areas, they were always ahead of us in terms of music, clothing and technology. I’m also adopted and a child of divorce, both of which, studies show, can drive kids to feel a need to prove themselves.

So between my small town upbringing and my personal history, I have always felt like I was playing from behind and needed to show people what I was capable of. That’s made all the difference in my career. In fact, even now that I’m on my sixth successful company I still think of myself as an underdog.

The power of being a perpetual underdog

Being an underdog means that, when somebody tells me something is impossible, it just motivates me to prove them wrong. When I started my current company, Vertex, I can’t tell you how many people told me that what we’re attempting to do just couldn’t be done. For me, their doubt wasn’t a setback. It just lit a fire in me to prove them wrong.

The same drive to prove myself helps with recruiting and customer acquisition. If I want to recruit somebody and ultimately it’s a no, that’s just one more person on my list that I’m going to prove wrong. It’s the same thing with customers. Always looking to show what I’m capable of keeps me relentlessly focused on the future and helps setbacks roll off me.

This underdog drive isn’t always pleasant. It’s not even always healthy (more about that shortly), but it is powerful. In Star Trek V, there is a character who claims he can take away people’s pain. But when this character approaches Captain Kirk, he resists. He says, “I don’t want my pain taken away. I need my pain.” That’s how I feel about being an underdog. (Yes, I’m a total geek, and this is the only good thing that came from Star Trek V, in my opinion.)

I came by my underdog spirit naturally, but it’s something I think every entrepreneur can cultivate. Conviction, commitment, and the determination to seize opportunity is essential when you’re building a business, and being an underdog helps with all of that.

Nurturing that drive is all about channeling your emotions to fuel your competitive spirit. It’s about how you conceptualize failure. When you experience moments of loss or disappointment—when other people tell you, “See, I told you that wasn’t going to work”—take those emotions and use them to drive you. Don’t let failure drag you down. Instead, use it to propel yourself forward.

The dark side of the underdog mentality

This mindset can be incredibly powerful but, as I alluded to before, it can also be destructive. It can leave you perpetually unsatisfied and looking for others’ approval. That’s not always a good place to be when it comes to both your mental health and effectiveness as an entrepreneur. Repeatedly knocking on doors despite hearing ‘no’ is a great skill for an entrepreneur, but you also need to have the ability to listen to what other people are saying. Always thinking about how to prove others wrong can get in the way of this crucial emotional skill.

Personally, I had to come to terms with the dark side of the underdog mentality after I left my last company, Workiva, and realized what a steep toll it was taking both on my own health and happiness, and the health and happiness of those around me. Working with a counselor, I examined what was driving me to prove myself to others. It sounds a little corny, but I realized I was searching for love when what I really needed to do was love myself.

Did that realization stop me from being an underdog? Did it dull my drive? Not at all. I just understand the healthy way to be an underdog now. Perpetually striving to prove yourself to yourself—to be a better version of yourself today than you were yesterday, to do more than anyone thought possible—can help entrepreneurs seize opportunity at any stage of their career.

Which is why, even though I’m on my sixth company, I still insist on seeing myself as an underdog.


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