A “Third Way” in Entrepreneurship

Entrepreneurship is often portrayed as an endeavor in which the entrepreneur has to essentially go crazy to succeed. Extreme dedication, total distortion of the work/life balance, and very high risk are some of the hallmarks of our conception of starting a new business (or even more risky, starting a new business with a new business model or product).

Moreover, entrepreneurs are pressured to maintain a totally positive face to the outside world about the state of their company. In San Francisco, “we’re killing it” is almost now an inside joke because of the ubiquity of that response when someone asks an entrepreneur how their company is faring. Most of these companies are not “killing it”, and the entrepreneurs probably know that.

It’s actually almost folk-wisdom that this quality (believing your company is “killing it” at all times) is a necessary mental quality for an entrepreneur. If they could be completely honest with themselves, the thinking goes, they would never be able to face the consistent stream of failures and setbacks without giving up. But maintaining this facade is hard, and it only makes the risks higher; a less than satisfactory end result now means abrogating promises and not meeting expectations that you yourself helped create. 

One has to think that there is a way to run a company that doesn’t exact such a toll. Leaders in the field of startup management, especially Eric Reis, have outlined new ways of thinking about starting a new business that permit new ways of behaving. Instead of being deterministic (i.e., the entrepreneur is in control of what the company will be and do, and effort will determine success) and linear (i.e., there is constant progress towards success), most startups are nondeterministic (you may succeed but you will not control how) and nonlinear (you will experience small failures constantly until you succeed, perhaps wildly). Deterministic/linear thinkers (or those who perceive that others think that way) are under more pressure to maintain this facade relative to nondeterministic/nonlinear thinkers.

In all, I think there’s a different way to be an entrepreneur. One that encourages work/life balance. One that doesn’t demand a stark dissonance between your public face and private reality. One that recognizes and embraces the nonlinear nature of startups – i.e., that it’s ok not to be “killing it” all the time.  

  • Well said! The “killing it” phrase needs to be killed. The notion that you have to be blindly optimistic is idiot. We are humans – be a human – deal with the inevitable ups and downs – both functionally and emotionally.

    • A friend once relayed a story to me of a dinner meeting of ~20 early-stage high-tech executives he attended that was sponsored by a startup organization. The moderator asked one question as an ice breaker to kick off the night: “What is the greatest challenge that your startup faces today?”

      My friend was the first one picked to share. Being a very level-headed guy (who personally hates the term, “killing it”), he suggested that one of his biggest challenges was maintaining work/life balance & personal relationships, for himself & also for his employees, so that they don’t burn out on the job.

      The baton then got passed to the next entrepreneur, and, as my friend tells it, entrepreneur after entrepreneur shared their “greatest challenge”, though they were only “challenges” in the weakest sense of the word. For example: “handling all the new customers we have”, “scaling our servers for our massive user-base”, “hiring enough software engineers to keep up with the business growth”.

      He realized then that every entrepreneur was “positioning” the answer to make it appear that the greatest challenge faced was dealing with the company’s illusory massive success. I think this anecdote describes the “killing it” mentality quite well — even among peers and in a setting where people should be comfortable sharing their fears, this community prefers reality distortion.

      • It’s easy to change this. All you need is a few leaders in your startup community who will be honest about what is actually going on. Once this starts, it’s a cascade of real conversation that is awesome.

        • I don’t doubt it. I’ve noticed that great conversations happen in small communities I’ve formed of entrepreneurs who know each other for a long time and turn off the distortion field, even if only temporarily 🙂

  • John Rodley

    This reminds me of a study I heard of a while back talking about long distance runners. Conventional wisdom was to “ignore the pain” i.e. pretend you’re killing it. But this study of the most successful runners claimed that they approached it entirely the other way round. They embraced the pain, focused on it, studied it as if it was a key part of the experience. I don’t run enough to know if that’s true – the donut shop is not that far away – but there appears to be a parallel.

    Charitably, I’d like to think the “killing it” crowd is doing something a little different a la General Sherman as described in the Ken Burns documentary. “Sherman never admitted a mistake, or repeated one”. He was always “killing it”.

    • I think the running analogy falls short. The “killing it” runner ends up injured & in 2nd-to-last place coming out of his first marathon, and when asked how it went and what he could learn from the experience, he tells everyone he won and learned how to win repeatably 🙂

      • John Rodley

        Ha! True. I can’t resist an analogy even when it doesn’t work. The whole discussion doesn’t apply to me anyway. “It” is usually killing me, not the other way round.

    • I think your charitable interpretation is probably correct. Beneath the veneer, at least the good entrepreneurs are probably honest with themselves. But what I think is rough is the higher-level effect that everyone constantly saying they’re “killing it” does – especially to the entrepreneurs that need support.

      • John Rodley

        The higher level effect is exactly it. Each is potentially doing the right thing for himself, but holding back the community by doing so. Maybe there’s a “herd” analogy in there somewhere.

        I’ve only found a couple of entrepreneurs, peers, who’ll talk openly about the actual challenges they face. In both cases it came about as a result of a “give before you get” interaction. I’d helped these guys with things that I wasn’t going to get a return on. And none of these more open discussions would happen outside a 1 to 1 conversation. It’s never going to be a get-in-touch-with-your-feelings community imho. I think the best you can hope for is fierce, and frequent honesty one on one.

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  • Andy Monin

    I agree that “killing it” gets over used especially by the “posers” out there. “Killing it” has become the one line answer to the question “How ya doin?” from the acquaintance asked at the coffee shop. If you are an entrepreneur but not a natural optimist, fake it until you have brain washed yourself into believing you are. There are lots of battles to fight every day. “Killing it” may be an appropriate response to some of these battles, all the while losing others. I cant imagine a day when someone answers that “how ya doin” question with “Well… We are running out of cash, we built the wrong features, revenue is down 30%, costs are increasing, got an injunction from my former employer, and i ran over my dog backing out of the driveway this morning.”  All of this may be going on and the entrepreneur is too busy to focus on the negatives because there is a pivot right around the corner formed from the sum of his success and failures. It’s blind faith that a new direction will ultimately lead to “killing it”! Go get it!

  • MoreyBean

    Bravo! “Killing It” can be easily equated with “Killing Me”. I’m not crazy about the “non-” designations. How about Contextual instead of “non-deterministic” and Relativistic instead of “non-linear”? I also don’t think it’s an either/or situation. There are times when entrepreneurs need to be really fucking determined as well as times that call for ultimate laser focus and “linear” thinking, but always within a relative context, like life at home, exercise, meditation, eh?

  • Mike Volpe

    I lived in the Bay Area for 4 years, and I got so sick of the “killing it” talk and the complete lack of grounding in reality.

    I much prefer being an entrepreneur in Boston. People are much more grounded in their expectations and their rhetoric.

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