In Defense of Bootstrapping or Why Asking For Permission Sucks

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Dan Oshinsky
Dan Oshinsky



Some things I like asking for. I like asking for help. I like asking for favors.

I hate asking for permission.

This presents a sort of problem for me, as far as working in a bureaucratic environment is concerned. When I worked for a big company, I tended to do first, ask later. I took on assignments of my own curiosity. I wrote memos my bosses didn't ask for.

I got a lot of death stares.

But what I discovered along the way is that I'm a particular type of worker: I'm a bootstrapper.

That's a word that doesn't get used often enough in the workplace, probably because it's misunderstood. Here's what bootstrapping really is: A way of getting things done without having to ask for permission.

Meet Brandon and Lance

Take the example of Brandon and Lance Kramer, the two twenty-something brothers behind Meridian Hill Pictures, a Washington, D.C.-based film company. They're bootstrappers. They started 18 months ago with some savings, an office in Lance's basement and this thought:

1. D.C. has a lot of needs.

2. We're non-fiction filmmakers.

3. There's a lot of non-fiction film, but not about D.C.

So they came to a simple conclusion: We need to make films to serve our community. And better still: We need to build a community around these films.

So we should start a community theater to show films about D.C.

But how to get from Lance's basement to that vision? The Kramers started working on small films with local non-profits. Brandon remembers sitting in meetings, pitching his company. They were a bit short on experience, but long on vision and enthusiasm.

"I'm saying, 'We can make a film!'" he remembers saying back then. "Well... we can kind of make a film."

But one successful pitch led to another, and another. Now it's 18 months later, and the brothers have an (above-ground) office and a small team. With funds from previous projects coming in, they've started to move towards bigger things. In 2011, they started working on an independent, self-funded film. To get it to the quality they'd like, they're launching a Kickstarter campaign this month to help pay for the pricey post-production work.

Note the order there: They started work on the film, and only once it started growing did they seek outside funding.

The brothers are true bootstrappers, keeping one eye on their vision and one eye on their balance sheet. They're figuring out ways to do the projects they want, thanks to the backing of a bootstrapper mentality.

"The value is in the doing," Lance says.

Best yet, the Kramers took a step towards that dream of community theater with the fall launch of The Picturehouse, a screening series for D.C.-centric documentaries. Watching the crowds come out for the screenings, the brothers were able to really see that they were building something far beyond them.

All that from two brothers who started out 18 months ago with a little money and a basement office.

Bootstrapping From Work

That's bootstrapping on a big scale: making movies and building a business. How do you do it within the limits of your job?

Here's the story of Ben Barry, who took a job at Facebook, and then "kind of secretly built out a little screen printing studio" for himself. Writes Barry, "I didn't ask for permission, I just did it." Now it's part of his job to make posters for the office.

Here's the story of Amber Rae, a New Yorker who decided, in her spare time, that she wanted to help others find their passion. She launched The Passion Experiment on her website. In three months, 180 people applied to seek her advice.

Here's the story of Derek Sivers, a musician who decided to help some friends sell their CDs online. He started with just a bit of code on his website. He ended up with a multi-million business called CD Baby. His advice: Start now. Start small. That'll help you focus on the problems you really want to solve.

Point is, bootstrappers get things done. Even before the money starts coming in. Even before others start recognizing the full value in your work.

And long before anyone gives you permission to solve the problems or do the things you really want to do.

Continue the Discussion

  • Take baby steps: You don't have to have a million-dollar idea. Just something you're passionate about.
  • Look for little problems: What is it that slows you down? That keeps you from achieving all you want to achieve? Focus on solving those problems.
  • Find a team to support your efforts: You might not have a lot of money to start your bootstrapped project. You'll need a support system to help you find answers for the things you can't pay for.
Topics: Office Politics

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