Business Tips from the Underground: Alexa Clay Gives Lessons In Creativity from Hackers, Gangsters and Other Offbeat Thinkers

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Business Tips from the Underground: Alexa Clay Gives Lessons In Creativity from Hackers, Gangsters and Other Offbeat Thinkers



In Alexa Clay’s book, The Misfit Economy: Lessons in Creativity from Pirates, Hackers, Gangsters and Other Informal Entrepreneurs (Released June 23, 2015) she shares what she has learned about creative thinking by talking with bootleggers, counterfeiters, hustlers, and other misfits living and working on the fringes of society. Like a Boss Girls spoke with Alexa about how misfits can inspire today’s up-and-coming entrepreneurs.

How did you get interested in misfits?
I think I always had an interest in misfits or iconoclast type personalities. Growing up, I think everyone wants to be the cowboy outlaw or the robber in cops & robbers. I thought Joan of Arc was amazing. These are people, who as you get older, maybe, become viewed as crazy and “bad” in some way.

I think I always had a real appreciation for the risk taker, and I started doing interviews. I met with the former leader of the Latin Kings in New York, and I met with a bunch of guys who had been drug dealers as well, who then were working to develop formal ideas for entrepreneurship—someone for example who used to deal heroin who then wanted to start a food catering company or something like that. I became interested in this idea that ex-cons have all these amazing talents from their former lives, but how can they use those entrepreneurial skills within the mainstream economy?

How did you get in contact with the misfits in your book?
It varied. Sometimes it was as simple as talking to people or finding a drug dealer in the city and that would lead to an opportunity. There’s no LinkedIn type of thing for the underground, so it was really asking as many types of people as possible, and then going exploring, being out on the streets in all of these different markets and talking to people, and saying “Hey, do you know anyone who meets this profile?”

Only a portion of the stuff that we looked at were really illegal enterprises. We also talk a lot about different types of misfits. I was just in Indiana, for example, because a friend of mine had done a bunch of work with the Mennonites, and so we got to stay with an Amish family there, and they had a camel milk trader who was their neighbor. An Amish camel milk farmer, so that was nice. And just like, embedding yourself, sticking around for long enough to talk and explore, because I think if you’re just there for one day, you get some version of the story, but spending a bit more time, you get the richness of someone’s life and what they’re about.

Was anything really surprising to you about meeting with them?
Everyone is like “What was the scariest moment?” and I didn’t really feel fear at all in the research, you know, hanging out with the kid of a mafia family or meeting with some of these gangsters. There wasn’t ever a moment where I felt afraid or unstable. I think I was really surprised by how much empathy I felt, and how I discovered kindred spirits.  How a guy who has been in a gang for twenty years had so much common with my personal philosophy, and how there were similar characteristics between people who were coming from such different worlds.  I was just really surprised to uncover folks who really resonated with me.


What does it mean to think like a misfit?
I think it’s all about hustle. It’s all about entrepreneurship, just really having the grit to go for something, to take destiny into your own hands and not just conform to an existing job description. A lot of it, too, involves the spirit of hacking, so you know, taking on the establishment in some way, whether that’s creating a new type of company or trying to change the way something is done.

We profile misfits who are hacking our education system, asking whether or not we even have to go to school and reimagining what that would look like. We talk about the need to provoke and ask challenging questions, to spark dialogue and do that sort of myth-busting that needs to happen within the system. I think too often we take the status quo for granted and we don’t question really arbitrary things. All the misfits that we profile are not just born into cultures, but they’re really trying to hack the cultures around them, so they’re asking hard questions in that way.

Do you think most entrepreneurs play it too safe?

I don’t know about “most.” I think even entrepreneurship is becoming a little prescriptive in its path, so there’s a question for me with entrepreneurs of like, how do you do something really meaningful as an entrepreneur? How do you develop something that’s not just a sort of mindless app, or an addictive digital technology, or the next Facebook, but how do you do something that’s really meaningful and purposeful? As well as, how do you think about entrepreneurship more broadly, outside of just a Silicon Valley model? Like, how do you think about developing community entrepreneurship?  I was just on a tour of the U.S. and I met an amazing woman who started a charter school that’s built from scratch in Waco, Texas where the [city’s] graduation rate was only like 10% or something, and she’s a total entrepreneur. The entrepreneurial mindset isn’t just for mainstream businesses. It can be a part of a lot of different contexts.


How do you overcome the fear of getting in trouble if you’re going to stretch or test boundaries?
I think one of the things that we noticed was a behavior trait among a lot of the folks that we interviewed was that they cared less what other people thought of them. I think that’s just about really understanding your mission and not letting other people dilute your mission. That doesn’t mean you should ignore the world and not stress test your ideas, but really staying true to your own conscience.

One of the misfits that I love, because I grew up in Boston near Walden Pond was Henry Thoreau and all of his writings about self-reliance. The power of learning from hermits. You need to do some deep lifting with yourself and explore what you’re really about and what your legacy should be, and I think if you have that crystallization or distillation of your vision, then it’s easier to commit to that and be less concerned with what other people think.

What do you think Like A Boss Girls readers will take away from your book?
I think it’s really about: How do you create your own job? How do you develop a capacity to sort of walk an uncharted path and create that for yourself?  I think all the characters that we profile were able to do that—they were able to tolerate uncertainty and ambiguity and stay true to themselves. I think it’s hard. I think it takes enormous resilience to not just take a cookie cutter approach to life, but actually value your uniqueness, and figure out what makes you special and use that as a basis for orienting your life.  I think for young people, it’s not just about plugging in and doing something because you think it’s required of you or looks good on your CV, but really listening to yourself and taking risks. The most successful people that I know are ones that are able to deal with uncertainty and ambiguity, and aren’t afraid to figure it out as they’re going. They aren’t afraid to improvise.

For more on misfit thinking and Alexa Clay’s book, The Misfit Economy: Lessons in Creativity from Pirates, Hackers, Gangsters and Other Informal Entrepreneurs, visit

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