Dolemite And The Three Rules Of Bootstrapping

Rudy Ray Moore’s career, particularly as depicted in Dolemite is my Name, is a masterclass in bootstrapping. Set the bawdy humor and general chaos aside, and this is a story of how a struggling, early-40s aged musician and comedian created a lasting legacy in both fields. Moore finds the keys to his success when he stops looking to authority for direction and starts intensely paying attention to the audience he seeks to serve. The story is applicable to the work we all do (moderate spoilers ahead). 
Early in the movie he laments, “I ain’t got nothing nobody wants.” He’s moved across the country from Arkansas to Hollywood to “make it.” He’s borrowed money from family members to record albums as a musician. He’s gotten ignored on stages as a comedian. He’s begged the DJs, the record labels, and even the local club owner to let him do more – and they’ve all told him “no.”
Instead of pursuing the executives, why not directly pursue the audience? Instead of the people in power dictating what’s in style, why not pay attention to what the audience wants? This is the first step in bootstrapping. We don’t need an existing authority or power to pick us, we get to pick ourselves and build our own audience. We’ll still need to uncover work that matters to our people, but that’s how we convert them into our people in the first place. We don’t need to do work that matters to the powers that be. We have to do work that matters to ourselves and our audience. 
Moore adopts and adapts stories from local bums, elders, and people around the neighborhood. They’re lewd, but they are attention-grabbing, and no one else is quite doing what he’s doing. He tries the role out as an MC and it succeeds. He tries it out as a headliner. He takes it on the road. He borrows money to make an album. He gets a record deal and he charts on Billboard. He decides to make a movie and has to self-finance it using his recording rights as collateral. Its hard, hard work. Physically, emotionally and financially. But, it’s incremental progress every step of the way, even with the near countless setbacks. 
Instead of leaping straight to the top, it’s a slow climb. This is the second step of bootstrapping. In order to expand our audience, we have to understand not only what they want – the message, but how we get it to them – the medium. Moore was able to steadily build his audience through various mediums, the next one always building on the last. At first, it was face to face. Then it was on stage. Then it was via recordings sold at shows. Then it was on recordings played on radio and sold in record stores. Then it was movies playing in theaters he rented. Finally, he reached his audience in movies shown across the country. We have to understand our message and the mediums by which it spreads. 
In order to scale, Moore had to surround himself with people who shared his vision and were willing to grow. Perhaps the best aspect of the movie is the personal relationships he carries with him on his ascent. From his cashier friend at the record store to his female performance partner that he scouts when he witnesses her throw a punch in a bar. Bootstrapping requires community, and community includes not just a unifying vision, but one that combines the leaders, the players, and the audience. 
This is the third step in bootstrapping. In order to ratchet up, we have to gain the leverage of the entire ecosystem we are building. Moore’s relentless commitment to community building at each step of his journey is downright emotional to watch. We can seek to do the same with our coworkers and clients alike. Culture is not a set of beliefs, but a set of actions. Moore’s commitment to the work and his belief in everyone around him, even when he doubted himself, drove their growth. This is beautifully depicted at the end of the film. 
The movie and its subject matter may not be for everyone, but the underlying story is remarkable. Watch it with these rules of bootstrapping in mind:
  1. We can’t wait for someone to pick us, we have to first choose ourselves. 
  1. We have to understand how we connect with our audience, both in mediums and our message. 
  2. We have to constantly build a community around our ideas. The community involves the players and the audience as one ecosystem. If we seek growth, the entire ecosystem will need to scale together. 

H/t Seth Godin – these aren’t his three steps to bootstrapping, but they are directly inspired by his work. See his Bootstrappers Workshop for more.

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