This Entrepreneur Quit His Day Job To Make A Little Rubber Thing For Your Headphones

A cursory search under “headphone management” will bring up virtually hundreds of products. Spoolee’s novel contribution to the category is a twig adrift in an ocean of competition. This seems like a small and unusual product for us to cover but there are three things that make this product stand out and that are worth mentioning:

  1. The industrial designer who created it—Ray Walker—quit a lucrative day job to go after this startup dream of his. That’s mostly what I want to talk about.
  2. It is pretty clever…definitely filed under “holy crap, why didn’t I think of that.”
  3. It mostly works as advertised.

But first the basics: what is it and how does it work. According to Ray, the idea for Spoolee came pretty quickly as he was solving a problem mentioned to him by his wife: her headphones kept getting knotted up and that was annoying. We’ve all been there.

So Ray created Spoolee—which recently completed it’s Kickstarter for funding—to solve this problem. Spoolee is a neoprene loop that fits on your finger, like a ring, and makes it super easy to roll your headphones around it until it’s fully wrapped. A Velcro loop, keeps it from unwinding.


The best part is unwinding it, which consists of pulling on the headphones and watching the whole thing smoothly unwind, rotating around your finger. That’s really all there is to it, but it pretty much works and solves one of the more frustrating (first world) problems of the earbud generation. Actually this problem existed in the technological Precambrian era of Walkman headphones too but alas, we of that ancient era were forced to suffer.

You can wash Spoolee. You can squash it. It’s durable. Even in the prototypes, the quality is good and gives it—as they teach you in business school—a solid sand cone foundation. It seems like a random product but I have to admit, Ray really thought this thing through.

His design is interesting and effective. The materials are right (and we can look to my high school pal John Roscoe Swartz’s company BUILT to see what kind of runway there is for neoprene…quite a bit actually). The price seems about right. The need is actual, albeit not critical. This all makes sense.


But what doesn’t make sense is what it is that drives a person give up a good, stable job in order to make little neoprene rings? It seems like a big risk for something so small.

I’ve been thinking about it since I met Ray and we talked about this many weeks ago. What are the contributors to this little bit of irrationality that fuels action of this sort?

Part of it is probably the same force that made this guy become an industrial designer in the first place—a need to create. There has to be more to it than that, though…more than just a need to create and solve problems. What is the intangible force that caused this enterprise become a startup? Where did that transition to entrepreneur happen? What pushes a person over the edge to burn the ships on the shore and commit?

I’m sure not having any kids or dependents mixed in with an alternate income helps, but I’m betting the real culprit is the quest for discomfort that seems to accompany so many entrepreneurs and I’m thinking that likely contributed the final push. Let me explain.

Steve Siebold described the wealthy in his contentious and possibly mistitled story for Business Insider, by saying that “the wealthy are comfortable being uncomfortable” and “the wealthy dream about the future”. His hypothesis, while generalized and simplistic, is still interesting to me somehow and resonated more as a story about entrepreneurs than anything else.

As was echoed in many of the comments of his story, I instead like to think of those points in terms of entrepreneurship—restating them as “[entrepreneurs] are comfortable being uncomfortable” (read: capable of embracing uncertainty) and “[entrepreneurs] dream about the future.” When I think of Ray’s enterprise from that standpoint and within the context of those two modified statements, it sort of all makes sense to me and answers my question about why many people become entrepreneurs.

I’m sure there is probably a bigger product picture in Ray’s mind. Undoubtedly, there are bazillion products he could make and this is surely the beginning. And he may be thinking “if not now…when” as the future is always swiftly becoming the present.

Or I could be massively overthinking this and Spoolee is a one-off. There’s no doubt though that Ray really put in some effort to make this thing come to life: prototyping and producing it in China, investigating domestic production, funding a successful Kickstarter campaign. It’s a little piece of hardware but it takes a ton of time and effort to bear it forth as a business.

I think once an effort like this gets started—even something super simple like Spoolee—that effort is obviously infectious. We wouldn’t see so many startups out there if it weren’t.