Bootstrapping is thinking long, not small

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Adrian Holovaty, the founder of Everyblock and one of the creators of Django, put up the notes for a talk he gave about how Chicago needs to stop playing by Silicon Valley's rules.

His points are extraordinarily well articulated and he outlines the case for why the Chicago tech community should brand itself as the city for bootstrappers. 

I wanted to just stand up an shout out loud 'THANK YOU THANK YOU THANK YOU' as I read his write up.

I loved just about everything he wrote and a lot of it reminded me of the commentary I had on past hack job press coverage of the Chicago tech scene.

But there's one particularly disturbing thing I noticed happening in conversations after his talk - which is that some people equate bootstrapping to 'thinking small'.

And in fact - bootstrappers often seem to give in and accept the meme that bootstrapping equates to thinking small.


But this is wrong.

Bootstrappers don't think small, we think long

This is an important distinction because thinking small implies that you've set limits on your growth and the impact you want to have. I know a lot of bootstrappers, but I know of none who want fewer customers or who care any less about wanting to make their dent in the world.

What we do care about however is how we get those customers, who we have to partner with on our way to acquiring these customers and what kind of day to day existence we have as we build our companies.

This is thinking long, it's not thinking small.

When you start having a time horizon for success that spans 15 or 20 years, you look at the world and the opportunities it presents differently.

You know that in order to be strong you need deep roots, which are unsexy and usually go unnoticed and unappreciated until they finally take hold when suddenly everyone recognizes your 10 year overnight success.

It's silly to accept the notion that bootstrapping is thinking small, especially when the very people who claim that it is are building their products with a framework created by bootstrappers (Rails or Django, take your pick) and committing their code into a central repository created by bootstrappers (GitHub).

Bootstrapping definitely isn't easy, it certainly doesn't hockey-stick and it probably won't save an otherwise worthless portfolio of investment assets.

But to call it small is to misunderstand the very mindset of the bootstrapper.

We think long, not small.