Connections: The Raw Material of Entrepreneurial Imagination

If the secret to entrepreneurship is a well-developed inwardness, then how does one develop the inwardness of an entrepreneur? What is the nature of the foundation on which an entrepreneur is built? How can you increase your natural stockpile of imaginative raw material? How can you connect the dots that you otherwise would not know are there?

IMAGINATION

What defines an entrepreneur is her ability to conjure into existence a brand new product and then to bring that product to market. That initial conjuring is the deepest mystery and the first and most-important step on an entrepreneur’s journey. You can learn marketing and pricing strategies from others, but there is no sure-fire way to generate a million- or billion-dollar idea and then to recognize it as such, so much so that you devote your life to it.

The poet Rilke understood imagination as the “the spirit that makes connections,” and so did Steve Jobs. Jobs famously said creativity is just connecting the dots. He said:

Creativity is just connecting things. When you ask creative people how they did something, they feel a little guilty because they didn’t really do it, they just saw something. It seemed obvious to them after a while. That’s because they were able to connect experiences they’ve had and synthesize new things. And the reason they were able to do that was that they’ve had more experiences or they have thought more about their experiences than other people. Unfortunately, that’s too rare a commodity. A lot of people in our industry haven’t had very diverse experiences. So they don’t have enough dots to connect, and they end up with very linear solutions without a broad perspective on the problem. The broader one’s understanding of the human experience, the better design we will have.

So what types of things should be connected? Of course, the answer is everything, which as true as it is unhelpful. But when looking for a business idea, there are certain types of connections you can seek out.

Sometimes business ideas come out of need; you simply want a product that doesn’t exist. Other times, they come because you realize you have some relatively unique skill and decide you want to monetize it. And sometimes, a business idea is born consciously, willed into existence by an entrepreneur looking for just such an idea. These are the most interesting, because they suggest the possibility of following repeatable steps to conjure significant businesses into existence.

In 2005, I was very much looking for an idea. I had just sold and exited my first company, and I was mourning it, with too much time on my hands to question if I had sold it too soon. I needed that void to go away, and starting another business was the only cure. My first instinct for a new business was college guides, but from an insider’s perspective. My second was a marketplace for affordable, original art, and my third was a social network for meeting new people, named myYearbook.

There’s an old leadership proverb that says – if you want to be a leader, find a parade and jump in front of it. I came to realize the advice is actually sound, especially when modified to add the concept of connections: if you want to be an entrepreneur, find two or more seemingly unrelated parades and jump in front of them all.

By “parade,” I am referring to industries, technologies, and sectors with natural tailwinds, areas where with near certainty you can predict that two years, 5 years, and ten years out that area will be bigger, substantially bigger, than it is today. By definition, then, a number of fortunes will be made; yours just needs to be one of them. In 2005, I recognized that social networking would be dramatically big; it seemed, even at the time when Facebook was only at Harvard and I was one of the first thousands of users, that it would be a billion-dollar idea.

My intuition dramatically underestimated the opportunity, as it turned out, but it was good enough. Put simply, I thought if Facebook could be worth billions than there would be players that would be worth millions. At that time, Myspace was already dramatically valuable but flawed in almost every way a product could be flawed; Friendster had been valuable but flamed out for mostly technological reasons; it seemed to me the parade of a “social network for friends and family” could be combined with an unrelated parade, in this case a social network for meeting new people, which would eventually turn into a social network for dating, which myYearbook, now MeetMe, is today. Today, we would liken it to the bar or the coffeehouse, a social gathering place, but at its core it is a social dating network.

When I started another app in 2019 called Podcoin, I also consciously looked for seemingly unrelated parades to connect. In that case, I connected the disparate parades of podcasting, gamification, and virtual currency. The app incented users to listen to podcasts by rewarding virtual currency, called Podcoin, which translated to a few pennies per listening hour and was paid out in gift cards for Amazon, Starbucks, and a dozen other brands. The incentive drove significant adoption from new users and proved to be extremely cost-effective marketing.

The business insight was that through variable earning of Podcoin I could direct listeners to discover podcasts that they never otherwise would; enabling a potential monetization driver for podcast discovery where podcasters pay for new users by listening hour. The app grew quickly until it blew up for an unrelated reason, which I'll cover in a post about gatekeepers. Nevertheless, the concept of connecting multiple parades led to an idea that quickly grew virally and showed signs of life, including 20% day-30 retention.

If creativity is simply making connections, then you can drive creativity by listing the industries and sectors that interest you and that are experiencing tailwinds, like gene-therapy, artificial intelligence, audio, home automation, clean energy, workplace wellness and sanitization, etc. and then looking for novel connections to make among the industries. For example, maybe you should create a line of sanitizing UV-C light robots that ride around homes like Roombas or a line of UV-C refrigerators where the lights turn on when you close the door. With this method, you still must imagine a concept into existence of course, but you can limit your brainstorming to particular segments and industries which may prove useful.

If creativity is making connections, it means you must learn to sweat the small things, which so quickly become huge and immeasurable. For connections to be made, you must combine the forest-through-the-trees perspective with the view from the forest floor. Sometimes the connection between two parades is a seemingly small tweak, the kind that would invite scorn from your family when you tell them you are leaving your job to pursue your startup dream. 

Snapchat’s well known hook, the ephemeral photo, is just such an example of a seemingly minor tweak creating an empire. Snapchat connects the disparate parades of “messaging” with “privacy” with “nude selfies.” While the hook, a disappearing photo, may seem like a small feature, it was actually the seed of $30-billion-dollar media empire.

Bumble, the dating app where women make the first move, is another seemingly small hook that ingeniously jumps to the front of two parades: mobile dating and female empowerment. While larger dating/swiping apps could and did eventually copy the feature, the power of the feature was in the brand and marketing power, not in the user benefit, and so Bumble’s small hook became a $3 billion dating behemoth assembled by a Russian entrepreneur and now owned by a global investment firm.

An entrepreneur’s inward nature can either throttle or amplify her ability to imagine something truly worthwhile. By actively seeking connections across seemingly unrelated concepts and concerning yourself with both the big and the small things, you can increase your natural stockpile of imaginative raw materials. By casting both wide and deep nets crossing industries, business models, and technologies and accumulating knowledge and experiences about human experience, you can ensure the broadest possible perspective on your startup idea and connect the dots that you would otherwise not know are there.

In the next installment of the Inwardness series, I will examine how solitude can aid in the act of making connections.