There are three main categories of players in the game of entrepreneurship: sellouts, hustlers, and lucky folks. Players are those who get to show up every day and do their thing (or try to). A sellout is a pretty dirty word. In some circles, hustler used to be, too, but by and large is no longer. Lucky folks are the people who can do without selling out and engaging in the hustle. They usually only exist in fairy tales and don’t need my help, so I will not be focusing on them much. Sellouts and hustlers are interesting to me because they both work, hard. They are united by effort and separated by their values.

To sell out is to sacrifice authenticity, or as Wikipedia says:

“’Selling out’ is a common idiomatic pejorative expression for the compromising of a person’s integrity, morality, authenticity, or principles in exchange for personal gains, such as money.[1] In terms of music or art, selling out is associated with attempts to tailor material to a mainstream or commercial audience; for example, a musician who alters his material to encompass a wider audience, and in turn generates greater revenue, may be labeled by fans who pre-date the change as a ‘sellout.’”

So you can sell out by literally accepting money for shady behavior, or by catering to the masses and their painfully unsophisticated taste. There is a pretty clear moral judgment in this and most of our definitions of selling out. The good guys stay true to themselves, and the questionable guys take the money and/or the acclaim.

Personally, I am always on guard, looking out for if and when my sharing and selling will turn into selling out and force me to abdicate my high holy ground. I am also a little suspicious of the idea that there is a moral or artistic high ground. The problem is that sounds a lot like elitism. Luckily, we have the term “hustler” to put a positive spin on sellouts and acknowledge that ethics get ambiguous when they enter reality.

The hustler is someone who works hard

Hustler comes from “Hussein” which is Dutch for “to shuffle.” It’s also slang for a prostitute. Wikipedia defines the hustler as someone who “work[s] hard from the bottom to the top spot (legal or illegal),” i.e., the American Dream in action. Hustlers are rule breakers, Mavericks: real estate scions, pizza delivery guys.

Sometimes, legality is beside the point. Hustlers can be shady, or not. Hustler hangs out on both sides of ambiguous moral terrain. “Hustler” is both a fitting gateway term to sellout and an ode to sacrifice, grit and the grind.

The easiest criticism to throw out about the social media hustler is that they’re all sellouts, but that’s not all that fair. It’s a privilege to do what you want, when you want, how you want and still be relevant. Social media superstars & celebrities can do without hashtags and embarrassing endorsements because they have a built-in access to the audience.

Instagram algorithms and the laws of the universe seem to favor popular people, so once an influencer achieves a substantial following, much of the growth & outreach take care of themselves, so the influencer gets to be themselves in front of an audience. That said, by and large, those same audiences were hard won.

Have you ever used a hashtag to get an extra on like a photo of yours? Have you ever judged the tan blonde girl in a crop top waxing rhapsodic about a cup of magic detox tea? My answer is yes to both, and I’m not particularly proud of doing either. I know better than to forget that we’re all part crooked, part principled. I can’t imagine that there’s a person who hasn’t had a moment of inauthenticity in pursuing any kind of dream.

Biting your tongue, kissing butt, brown-nosing, people pleasing, and putting in time are all kind of the same thing. They’re all steps that people take to gain just a little bit of ground. I think transparency and accountability are what distinguish the acceptable from the un(acceptable).