The Fundamental Entrepreneurship Challenge

entrepreneurship zen general

Thrashing n. To expend a disproportionately high amount of energy relative to the quality of output you receive

When I was younger and looked at successful companies, I simply could not for the life of me understand how they ever went from NOTHING to what they were today. The modern equivalent would be like asking “How did Jamba Juice launch hundreds of stores across the country? How did that start?” It made sense to me that if you raised a massive amount of money and then immediately bought all the capital equipment and hired all the people you needed then you’d at least be capable of serving all the customers, and that the massive revenue from the customers would balance out your massive expenses…but how did it all come to be from NOTHING? It seemed like magic to me.

And from this line of thought I embarked on what I believe is the fundamental fallacy of entrepreneurial thinking: asking the question “what does a company need to do to succeed?”

What’s wrong with that rather innocent question? Well, it’s missing a critical component that ultimately matters more than anything else.


If I were speaking to my self from 10 years ago today I would make a very important point of clarifying that the real question is not how can you grow a company to be successful. The real question is, how can you learn to be successful in the shortest possible time?

A college professor once told me: “Given enough time, every single one of you could completely master the subject I’m about to teach. But the problem is you don’t have enough time and neither do I. So you’re going to have to figure it out in one semester while you take all your other classes, too.” What a perfect example of the same phenomenon. When you go to school, the question isn’t “what can I do, no matter the cost, to get the highest possible grade in this one class”, the question is “how can I get the best grades in all my classes this semester while still having lots of time for fun?”.

I would say for myself that I have experienced more personal and business growth in the last 12 months than in the prior 3 years combined. One of the fundamental differences? I’ve started imposing more constraints on myself than just “learning how to be successful.” I think about how I spend my time on each of my days. If I feel like I’m thrashing a little bit (see definition at the beginning of the article), then I know something’s wrong and I invest some time to assess what’s going on.

I think one of the main differences for myself is that in the past year I’ve been fortunate enough to find some amazing mentors. These are people whose accomplishments I am blown away by, who I have a great personal relationship with, and who are willing to give me input on ambiguous issues that come up. After enough conversations, you basically start to pick up the same patterns of learning and the lessons that they accumulated over a lifetime. Mentorship, I’ve come to realize, is literally the primary mechanism through which society evolves itself.

I mean, think about it. If you didn’t know how to write but you knew how to speak, how ridiculously hard would it be to invent this concept of an alphabet, which combines different “letters” together to form “words” which are expressed in “sentences” which are organized in “paragraphs” and annotated by “punctuation.” Writing is such a basic thing and yet figuring out writing from scratch would take probably a millennium. But learning writing? Well, a few years in school.

That’s how it feels since I’ve been fortunate enough to find mentors. The “learning on my own” process is shortcut by about 99%.

When I think about how much thrashing I’ve done at different periods in my business career, it just makes me sad. As Mark Cuban says, you can make as many mistakes as you want in business as long as you don’t make a really big one. So, yeah, I avoided a really big mistake, but I think about how much time I spent on some things that one great conversation with the right person could have saved me from. I mean, really, think about it. The idea that a single 1-hour conversation could save you months of work?

And that’s really what it comes down to in the end. The enemy of entrepreneurial success is not failure. The real enemy of entrepreneurial success is thrashing. What would you rather be? Moderately successful at age 30 where you have another 70 years to apply the lessons you have learned, spend money, earn money, love, live life, grow, etc. Or ultra-successful at age 80 where you’ve spent the bulk of your life learning how to actually figure out how to be ultra-successful.

Life, of course, rarely presents such black & white choices and the greater point here is really about how given enough time, sure, just about anyone could learn to be as successful as they wanted, but that time is precious, and scarce, and should be spent thoughtfully and purposefully. A day spent making awesome progress on something you care about is infinitely more satisfying than a day spent thrashing.


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