Kevin Kelly on futureproofing your side hustle

Years before crowdfunding platforms emerged to give entrepreneurs a new way to turn side hustles into viable businesses, Kevin Kelly laid out a vision for the not-yet-named passion economy. 

In an influential 2008 post, Kelly crunched the numbers to show that you don’t need a million supporters to succeed as a musician, photographer, author, designer, entrepreneur, or inventor. You only need 1,000 True Fans.

It was an idea that caught fire in the creator community. At that point, despite the democratizing power of digital distribution, it still felt like a winner-takes-all environment. But there were signs the tide was turning.

As the co-founder of WIRED magazine, founding member of The Long Now Foundation, and author of the best-selling books New Rules for the New Economy and What Technology Wants, Kelly had become famous for his ability to put epic scale into perspective. 

So when he decided to hone in on the needs of makers and solopreneurs, early proponents of the passion economy like Li Jin paid attention. Then Jin paid it forward by investing in new platforms that help people turn niche skills into new businesses. 

Kelly says 1,000 True Fans was inspired by a key insight in Chris Anderson’s book The Long Tail—the sum of the tail of small creators represents a market that’s actually as large or larger than the market of the hit makers. “My response was, that's great news for the aggregators, but that's not good news for the creators.” 

Then Kelly started thinking about the internet’s capacity to provide creators with something truly new and powerful—disintermediation. “The same technology that allowed you to have a long tail also allowed you to have direct contact with your fans,” he says. Creators have always had fans, but those fans were mediated through the publishers, broadcasters, and record labels.

As Kelly points out, the ability to reach people directly also means having to tend to their needs. “That’s a full-time job, and it’s not for everybody. There are creators who would much rather just be painting or dancing or whatever, instead of having to deal with fans,” he says. “That's a perfectly legitimate take. But if you do that, then you have mediation, and the numbers are different.”

Kelly’s view of the future is that 1,000 True Fans is a viable option that did not exist before—but it doesn't mean it will necessarily become dominant. “Most makers will probably have hybrid versions where they have an inner core of fans, then other fans around them.”

In the 13 years since he introduced the idea of 1,000 True Fans, Substack, Patreon, Kickstarter, and Indiegogo have made the concept even more viable. For Kelly, these platforms seemed like a natural evolution of a business model he had a hand in developing decades ago.

“Before I came to Wired, I was publisher/editor of a magazine that had no advertising,” says Kelly. “It was originally called CoEvolution Quarterly, then Whole Earth Review. It was user-generated content for the most part, and totally subscription supported. So the model of having a completely subscriber-supported publication is no surprise to me. It feels very natural. It's just been waiting for the technology, in part, to catch up.”

But how do you convince people to start paying for content they’re used to consuming for free? 

“There are certain advantages to paying for things,” says Kelly. “I did a piece on my blog, which was about the ways you would have to make things better than free so people would pay in a world where you can have a free perfect copies of things.”

One way to begin is by looking at what you’re selling. In some cases, it’s immediacy.

“Say with music, you can get the free copy, but if you want it as soon as it comes out, you're gonna pay for it,” he explains. ”We're still moving towards the subscription model and figuring out what people are getting that they wouldn’t get otherwise for free. Patreon is part of that, but I think Substack is closer to the model of having an explicit bargain with people saying, ‘Okay, I'll give you this, you'll give me that.’”

Kelly predicts the next step is for websites to have a system of subscribing beyond individual paywalls. “I want to have a visible system where I just have one pass. I can imagine many technological ways we could have content be regulated in a certain sense, sold in a much more transparent system. We'll have this whole ecosystem of an all-transparent and paying aggregator sites. I think we're headed into a very exciting moment where that ecosystem can prosper.”

So maybe you’ve got a side hustle of your own. You’re reading this and thinking, “Sounds great. But where do I start? How am I supposed to find 1,000 true fans in the passion economy if I don’t even know what my passion is?”

Before he became a best-selling author with a long career of accomplishments, Kelly had to ask himself the same thing.

Photography was one of his first passions. It never did become his career. But it did teach him to pay attention to what he was interested in. And it helped instill a core belief that the most important skill to learn is the meta-skill of how to learn. 

Finding your niche in the passion economy requires you to keep learning about yourself by having the curiosity to explore and experiment. If you’re laid off, you might not feel like you have that kind of time and freedom. But Kelly says the key to discovering the one thing you can do that no one else can is to pay attention to what you do in your spare time.

“Marc Andreessen, the well-known VC guy, says that when he’s scouting around, the thing he likes to ask entrepreneurs is what they do for fun,” says Kelly. “What do they do as hobbies? That is usually where some of the best stuff is coming from, because they're doing it for fun, for play. They're doing it for free. They're wasting time. They're inefficient. Those are the qualities I think that you want to pay attention to in your own life.  Where am I spending a whole lot of time—the more time, the better?”

It’s in those moments you’re likely to notice the tasks you find easy that other people find hard.

“Maybe you can move what you're being paid to do in that direction from what you learn by when you're not being paid,” says Kelly. 

It’s also possible that the job you’re born to do doesn’t have a name yet. So if you’re an aspiring entrepreneur, what can you do to futureproof a new business venture? 

“If you’re trying to do something innovative, it's the brand new that has the most potential,” Kelly says. “You're not going to win with an existing occupied vertical or occupation or game. If your ambition is greater than that, you have to head out into the place where there isn't even a game being played right now. If you're willing to do something there isn't a name for, you're much more likely to have greater success.”