THE BLOG
05/06/2014 09:29 am ET | Updated Jul 06, 2014

From the Food Bank to Making Bank

Sophia and I met the same way everyone like us met: Loitering somewhere in public where we wouldn't have to spend money. In this case, it was at a (free) anarchist film fest in the back room of a dingy Olympia, WA, café. At that point in my life, I divided people into three categories: Those who allowed me to sleep on their couch, those who smuggled me free food from their restaurant jobs, and those to have mostly illegal adventures with. In one conversation, I put Sophia in the latter category. And, in a matter of weeks, I was sleeping on her couch as well.

We were quickly inseparable. Together, we ran wild through Olympia, wreaking turbulence upon the tranquil streets. Before setting out for our daily (or nightly) adventures, we put it to a two-question test: One, was it free? Two, could it get us arrested? Aiming to satisfy both, we'd usually settle for the first one.

I authored a book Sophia had read titled Evasion, a memoir of my life dumpster diving, shoplifting, hopping freight trains, and hitchhiking in my effort to "live free or die trying." Not a book your mom would have read (or approve of), but by 2002, most anarchists had. Her familiarity with my writing saved us any awkward screening process. So, you read about the time I went to a supermarket dressed like an Odwalla delivery guy and pushed a cart of juice out the door? And you're still talking to me? Let's hang out.
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This is where I'm supposed to reflect on every clue that eighteen-year-old Sophia would go from #GIRLTHIEF to #GIRLBOSS, but truthfully, there were only two. One, she was always the smartest person in the room. Two, I never saw her go after something and not get it quickly and efficiently.

The entrepreneurial foreshadowing in Sophia's history was more subtle. Flipping shoplifted books on Amazon is arguably the crime of a calculated entrepreneur (favorable risk-to-yield ratio). There was the time she furnished my entire apartment with dumpster-dived furniture (classic bootstrapping). And the night we wanted to explore an office building after hours, and found it locked, Sophia got us in anyway (framing everything as a challenge, never a failure).

We were vagabonds without road maps, outlaws without swagger. Both of us on the fast-track to paying for the frivolity of our post-high school years with the harrowing fates of our contemporaries: ending up in bad punk bands, as "political graffiti artists" or even worse - armchair radicals big on rhetoric and short on relevance. Kill us now.

Against the odds, Sophia went big and scored big. If I had to sum up the fundamental shift undergone by anyone who takes the (very few) good parts of anarchy-ism and brings them onward to greener pastures, I think it is best captured in this quote from serial entrepreneur Eben Pagan: "[the transition requires] moving from a value extraction paradigm to a value creation paradigm."

Oh man, did we "extract." Back then, we were so deep in value extraction mode, I remember not having the money for a 69-cent Boxcar Willie cassette at the thrift store. Sophia rose up to remedy this injustice by just stuffing it in her purse and walking out.

Then things got really weird, for both of us. I built a criminal record, Sophia built an empire. And we didn't cross paths for a decade.

Fast forward to 2013. I check my mail and find the new issue of Inc. Magazine. And there was Sophia -- on the cover. At least that's what the caption said, but nothing else was checking out. Makeup, form-fitting dress, hair a brush could pass through without much resistance. I was suspicious. So I did what anyone foolish enough to think they can contact a high-profile CEO does: Google "[name] + email," and fire off a one-line message to the first address that comes up. Before I could finish the article, my phone was ringing.

(Actually, it's not that easy. If you want the real secret to bypassing a CEO's gatekeepers and getting her on the phone in less than 30 minutes, I'll give you one hint: Sophia covers "social engineering" in Chapter Four.)

I have an obsessive interest in people who came out of the punk rock scene and became famous magicians, hip hop moguls, deca-millionaires... anything big. Problem is, there aren't many.

Some of what our subculture had taught us was empowering ("Don't wait for someone to do it for you, do it yourself"), some of it took a privileged sense of victimhood and inadequacy and spun it as "radical politics." ("Rich people are evil.") And much of it was a major liability for anyone who had dreams bigger than an anarchist bookstore.

From the food bank to making bank, we came out the other side of all of it, me with an Inc. Magazine subscription, Sophia on the cover.

Soon we were sitting across a table at a Hollywood restaurant, a decade since we last crossed paths. Just two old co-conspirators, reliving war stories.

"Remember our tag-team manipulation of Michaels Arts & Crafts cashiers? And that time we infiltrated the Olympia High School prom?"

She did.

"You know, those tricks we used to do... I use them in business every day."

And that, my friends, is a true #GIRLBOSS.