Major Major Major Major: The Catch-22s of Start-ups


“They’re trying to kill me,” Yossarian told him calmly.
“No one’s trying to kill you,” Clevinger cried.
“Then why are they shooting at me?” Yossarian asked.
“They’re shooting at everyone,” Clevinger answered. “They’re trying to kill everyone!”
And what difference does that make?”

- Joseph Heller, Catch-22

Clouded, convoluted lemmings are continuously running through the endless scenario trees in my head, each one a different start-up decision to make for tomorrow, or if I’m lucky, two days from now.  My constant fear is that one of the individual lemmings will drop off a cliff from a wrong, poorly timed arrangement, smashing into the ground below, creating a chain of events I’ll have to backtrack through the mud to clean up.  And, this might happen not necessarily because I did something inherently wrong–but because one of my actions simply contradicted another.

Welcome to the catch-22s of start-up land, where what often seems like the best call today can be the devil on your shoulder tomorrow, even unexpectedly.  People move fast; team members may lose interest.  Technology evolves, and can fall apart in the blink of an eye if a feature goes down because it was built poorly, or because a competing engineer abroad decided to build it better, strong, faster.

Catch-22s in start-up decision making can relate to anything, but in this case the examples deal with developers, teams and customers.  These scenarios I’ve unfortunately (and fortunately) experienced, while others I’ve simply observed:

1.  The “I love your team right now (until I get bored and move on to something else)!” developer.

Those most attracted to the world of start-ups, even in joining your lovable, tight knit team, may be the first to jump ship out of the world of start-ups.  The world of young business is extremely exciting, but has a short attention span.  You attempt to create something out of nothing on your own terms, often with little capital, relying on pure creativity and hustle.  However, it often forces you to focus on one task for a long period of time, specifically on the technical end of things.  The same guy that was dedicated to “your cause” today, has suddenly become bored, lost attention, and on to his next project tomorrow.

2.  The “we need a developer to raise money, but we need to raise money to hire a developer!” team.

There will always be a roadblock to raise capital.1  The trick is in prioritizing, or at least faking like you are prioritizing.   The easiest workaround is to hire a developer on equity2, as often these guys are the most dedicated to the cause and long-term vision of the company.  This can solve both problems.  But, if you understand the technology well enough to talk about it coherently without a developer, you may be able to raise capital in a strong economic market.

3.  The “I want to test this product because I might use it, but I might never use it because I don’t understand it!” customer.

This one is nearly impossible to loop around.  And, it happens in most businesses, technology or otherwise.  The situation is that usually a group of technologists create software they are rightfully familiar with, and they spend time testing it with customers who don’t understand technology in the first place.  This can misguide the product vision, especially if you test with the wrong type of noisy, irrelevant customer.  The issue is in figuring out the proper people to test with, which can be guided by lousy feedback if you’re not careful.

Catch-22 did not exist, he was positive of that, but it made no difference. What did matter was that everyone thought it existed, and that was much worse, for there was no object or text to ridicule or refute, to accuse, criticize, attack, amend, hate, revile, spit at, rip to shreads, trample upon or burn up.

I’m not complaining.  People don’t start businesses because it’s supposed to be easy, or even because it’s always fun.  It’s because of all the other rugged emotions bagged up along in the trunk, like the dignity of being in control each step up and down.  There is pride in knowing that if you fuck up, it’s your problem to figure out how to fix it.

Start-up land is a place where decisions can be indecisions, and success can be a factor of what you don’t do just as much as what you do.  And although I hate to admit it, sometimes just plain luck is all you need to make it to the next round, the next stage or the next ambiguous level of contradicting success.

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  1. Unless your engineering team is from Google or Stanford, which is basically saying the same thing. []
  2. For potential problems with this, see issue #1 []

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