The $100 StartUp Life

All the bad days have two things in common: You know the right thing to do, but you let somebody talk you out of doing it.
– Tom Bihn as quoted by Chris Guillebeau, The $100 Startup

And you say to yourself, this is not my beautiful house…this is not my beautiful wife.
And you wonder to yourself: How did I get here?
– The Talking Heads

Jumping Headfirst

C'mon in, the...bracken's fine?

There are a lot of ways that I can say I got here. But one in particular stands out a day after Chris Guillebeau launched The $100 Startup. The book resonates with me, because once upon a time, I was a $100 startup.

Coming out of college I had a diverse set of skills. Moves of a Dancer, Eyes of a Designer, Technophilia of a Geek read my business card, and it was hard to figure out how to market that. My skills lay in video, sound, movement, theater, web and CD-ROM design, and I had clients in every one of those fields. So what did I call myself? Web designer? Theater Tech? Something weird like Experience Designer or some scifi term like Shaper (from Spider Robinson’s Stardance books, in case you’re wondering).

One thing was sure: I knew I didn’t want to go to work for some of the big corporations that my fellow graduates had migrated to, and I also was in over my head. While talking with my attorney-and-best-friend-from-high-school, he suggested that I “might want to look into an LLC.” That is, in case you’re wondering, a Limited Liability Company. It basically creates an entity besides yourself that is in charge of bank accounts, copyrights, taxes, a layer of separation between you as individual and your work. You also get to do fun things like create a Board of Directors with your daughters on it, and dream about corporate letterheads and the like.

Sounded great to me, the more I read about it. So I paid the fee – around $100, if I remember right – filled out the forms online and poof I was suddenly the Director of a Corporation! I called my lawyer friend up. “OK, so I registered the LLC,” I said. “Now what?”

This was pre-facepalm and headdesk memes, but I think my friend managed to do both simultaneously. He’s been very careful, since then, in recommending I “look into” things.

Playing at Being Grown Up

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I had no idea what I was doing. What followed – well, what has followed, since it’s still putatively in existence – was a series of triumphs and failures and struggles. At one time I had rooms full of expensive equipment, multiple cameras, pro sound gear, the latest programs and an office in my house with two desks and extra tables to hire contractors (aka my friends) to help with proofreading, transcribing, or whatever else needed to be done. I had trips to see my accountant, I had proposals and tax summaries and write-offs and depreciations…and I didn’t understand a blessed bit of it.

I didn’t have the guidelines, worksheets, examples and warnings that are between the covers of the $100 Startup. Instead, I did what any young person with little experience and big dreams and multiple children does: I did the best I could. The dirty little secret that it took me years to figure out was simply this: So does everyone else. Some of us are just better at pretending – to ourselves and to others – that we actually know what’s going on. That our plans of execution actually execute our plans. The reality is that the results – whether good or bad – only seem like they were inevitable because they were what actually happened. If something else had happened, we’d point to it and say “Oh, yeah, I saw that coming.

Success in Spite of Yourself

Was it good enough? Well, I guess that depends on your point of view. I can say “Still in business, 14 years later!” because I am still doing some of that work, for a more select clientele and with vastly scaled-down expectations. But I’ve also incurred debt, had to sell off most of my equipment to pay rent, and left more than a few clients disappointed and angry because I overextended myself. Unlike the people and companies profiled in the book, I’m still not making $50-$60k doing my passion. Heck, sometimes I can’t afford tortillas to go with the can of beans in my otherwise-bare cabinet.

But success. I have succeeded. I am, as Morpheus would have put it in the Matrix, STILL HERE. I am getting close to my 100th blog post on this, my most recent project, and I’ve got Very Special Somethings waiting in the wings to surprise you with come July. I have friends all over the world, with more trips to visit them and make new ones planned. I have days that are filled with interesting, challenging, and meaningful work, and if that means that sometimes I go tortillaless, it’s really kind of a small price to pay.

I wish I could say I was brave when I chose to take the road less traveled in my career. The truth is, I was clueless and reckless. I still have the urge to apologize to my kids for the hand-to-mouth existence they grew up with. But now, in a far less secure job market, the idea of working for yourself doesn’t seem quite as crazy. The realization of if not now, when? and If not me, who? in regards to your passion has become more urgent.

Unlike me, you can read something like The $100 Startup (or just visit the resources at and at least have some idea of what might be waiting for you when you take that leap. Whatever kind of leap it is – a new career, a new home, a new relationship – it’s going to be scary.

But it’s also going to be worth it. Who needs tortillas, anyway?

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