Too Dumb to Quit - How Tenacity Pays Dividends in Entrepreneurship

Too Dumb to Quit - How Tenacity Pays Dividends in Entrepreneurship

   I am not an entrepreneur by training, but then again, who is? The best founders I know all cut their teeth not in a Harvard dorm or a fancy corporate boardroom, but out in the trenches. Building things, selling things, and never quitting when things got hard. The best founders are tenacious, and sometimes it is their most dominant trait. Sometimes even, it is their only skill.


This is a word I have often used to describe myself and one that others have used to describe me. Tenacious is what I consider so many of my peers in the startup community to be. It means the same thing as "relentless" and "persistent." Some might even say it means "relentlessly persistent," which is  more accurate still. 

Tenacity is not a nice-to-have quality for founders. It is a mandatory necessity. Without it, you will quit before you should. You will succumb to self-doubt, to criticism, to conflict, to fear and anxiety. Without tenacity, you will likely fail as an entrepreneur. 

This doesn't mean you need to be a jerk, or a narcissist, or an arrogant asshole, although there are no shortage of any of these personality types in the entrepreneurial realm. Jerks, narcissists, and assholes are often tenacious, and very motivated. They also think highly of themselves, which is a useful tool in a professional community that enjoys degrading founders at every turn, until most of them turn away permanently. 

The culture is as productive as it is toxic, rewarding those individuals without the normal societal filters that keep most people too politely ashamed to pursue their greatest dreams. When society tells us we are not good enough to succeed, that we should conform and be happy with the 9-5 ham-and-egg job, most people do. Where normal folks happily toil in the rat race, entrepreneurs head for the exits and make their own paths. It's really the way things have always been, a tale as old as time. 

When my entrepreneurial journey began, I suffered from an unshakeable case of imposter syndrome. I did not know what I was doing, and when I met some successes, I believed I wasn't worthy of them. I felt like a fraud, and like I didn't deserve to be there. It is a feeling most entrepreneurs wrestle with at some point or another, and it takes a long time to shake it. It's something that still haunts me from time to time. But throughout the better course of a decade, I learned to accept my shortcomings as normal. I don't always know what I am doing, but neither do most other people. There are themes and rhythms one gets attuned with. We experience failures, we learn from them and try our best not to repeat them. We experience success and learn how to accelerate those successes, and when to double-down on a good outcome. Timing is as important as tenacity. It is the acquired skill of learning how to identify opportunities at the most opportune moment. Seizing that prize before others in the space see it coming, and when an entrepreneur can be both tenacious and master the art of impeccable timing, the result can be a true thing of beauty.

In my experience, most people are not tenacious enough to be truly successful entrepreneurs. It is simply too hot in the kitchen for normal, sane, rational humans - and most of them can't stand it for long. I have had business partners and employees who buckled under the pressure of startup mayhem - the constant "do or die" realities are truthfully not fun to experience. But they can be addicting, and the pseudo-masochism of most founders keep us in the fray. It's akin to jumping out of an airplane - it's a real thrill so long as the parachute opens. But, jumping out of an airplane is not for everyone - and neither is entrepreneurship. 

I have worked with highly-skilled professionals from corporate backgrounds, kids fresh out of Ivy League business schools, and people with amazing ideas, who simply could not find success in the face-paced, chaotic, and high stakes world of entrepreneurship. Maybe they needed structure, or systems, or large budgets, or departments, or regularity, or security, or a reliable paycheck, and when they discovered that entrepreneurship offers few of these luxuries, (and often none of them), they fell to pieces. I've seen it happen time and time and time again. This is not to say that fancy corporate types and Ivy League graduates cannot be successful entrepreneurs. They can and they are all the time. But they still need tenacity and grit in order to survive. Skills and connections are usually not enough. 

I can gladly say the same sort of things about investors, especially venture capitalists and institutional investors of various kinds. In the past several years, I have pitched our business to hundreds of these folks, most of them rich, white men, who have never spent a day behind a shop counter or on a factory floor. I am not exaggerating when I say pretty much all of them told me we would fail. The margins weren't good enough, we would never be able to scale, there wasn't enough demand, and so on and so on. Of course, all of them were wrong, but being told "NO" a couple hundred times is degrading. It really wears you down. A normal, sane, rational human would probably have quit several times over. But I'm not normal or rational, I'm tenacious. I knew somewhere deep down that all of those Harvard blowhards were wrong about our business, and through years of not only surviving, but thriving, we've proven them wrong. Lots of people were surprised by that, but not me. 

It's not because we have been better or smarter than anyone else. It's because we never quit when people told us we should. We believed that what we were doing was important, and that it would change the world. Over time, lots of our customers came to believe that, too. People in our community believed in us, and then government officials and politicians, and then loads of customers, and then investors came out into the open and started putting their money behind our ideas. Belief and tenacity manifested our success. It is that powerful. 

In our business, Yaupon Brothers, we have a long way to go before we realize our ultimate goal of unseating imported tea from the cups of America's tea drinkers. It will be an arduous journey, and I'm sure many more people will tell us we should quit. We'll get shot down dozens, hundreds, or thousands of times. And it simply does not matter. It does not matter because along with adopting a tenacious spirit, we have also learned the science of running a good business. The fluff and pomp of self-confidence only go so far, and before long, good founders discover the fundamental need to develop a structurally-sound business with core values and a strong foundation. How often recently have we seen big tenacious founder personalities fail in spectacular fashion? We've been witness to the monumental implosions of FTX, WeWork, Theranos, and many others. All of the founders of these companies had tenacity nailed. They knew what they wanted, and they went out and seized it. But, they didn't give two bits about building a strong business. Eventually, the dog and pony show got tired and everyone could see that there was nothing of substance behind all the shiny objects. Tenacity, timing, and discipline - are tools every founder should learn to master. 

I know that this screed might come off as self-important, so I'll close with a caveat: 

The information I've shared above is not meant to be a manual or a field guide. It's simply a sample of things that have worked for me. I believe that they could work for others as well, but I'm wrong all the time. Another thing I have learned from entrepreneurship is that there are mostly no silver bullets - no hard and fast rules one should stick to without deviation. In my view, ours is a profession which rewards honesty, transparency, empathy, self-awareness, confidence, tenacity, timing, discipline, and risk-taking. It likewise punishes self-doubt, apathy, hesitation, indecision, and fear. 

I leave you with a delightful bit of sci-fi literature. The Litany Against Fear, from Frank Herbert's Dune:

"I must not fear. Fear is the mind-killer. Fear is the little-death that brings total obliteration. I will face my fear. I will permit it to pass over me and through me. And when it has gone past, I will turn the inner eye to see its path. Where the fear has gone there will be nothing. Only I will remain."


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