Dawn of the Parallel Entrepreneur

We’ve heard a lot over the years about entrepreneurs. They change the world, one product at a time. They deliver huge value to vast communities of consumers. Their crazy ideas seem like a passing cultural whim until seemingly all at once, they’ve accumulated 10mil followers and Wall Street is starting to notice.

Beyond that, we’ve heard about this idea of a serial entrepreneur. This is a person who starts with a dream, builds a company, sells it to another company, and re-invests the gains in a subsequent venture. This person is always working on one goal, building one product or making that one product better in some way. There is much innovation, but the path is linear.

I propose an alternative. Instead of slow-burn long-form projects that take 15+ iterations to see the public eye, I say we focus on lots of sprints, all at once, all in parallel. Work on only one project at a time, but carry several parallel ventures. As one venture’s needs grow, hire new employees to match. One skilled engineering VP can address the needs of many ventures by overseeing the efforts of whatever resources are allocated to the various ventures.

A wise professor of mine once said, “the ideal number of projects an engineer should carry concurrently is five.” At times in my life, I’ve thought him a fool, both for under- and over-estimating the ideal. Now, I think he’s spot-on. It’s no surprise that I’m juggling five projects at the moment and loving every minute of it.

I don’t want to downplay the significance of the efforts of those who choose to focus on a single project at a time. What I propose is not meant for everyone, and I have great respect for those who seek the serial path. However, for the select few who choose to seek to work in short bursts on a diverse set of projects, all concurrently, as project needs dictate, I present to you the path of the parallel entrepreneur.

I have previously written about the perils of what at the time seemed like biting off more than I could chew, being everything to everyone, and what an impossible task that is to undertake. I have since come to understand I was simply ill-prepared for the stresses of managing multiple fledgling businesses at the same time. It’s not like they teach that in high school or college. My mother did many things for me, but none of them was even close to sufficient to prepare me for the herculean task that is overseeing the operations of one startup company. I’m running five such companies right now, so I’d say she did a pretty good job.

The best part about parallelism, if you can keep yourself sane in the process, is that everything you do contributes to growth, positive change, and significant social impact. One need not rely solely on one Facebook-sized hail mary play for salvation. One need only invest in discrete efforts, each of which pushes the ball down the field for its associated project, and retain some equity in the process. Eventually, that ball reaches the endzone, and the project experiences a liquidity event. If you only have one ball in play at any given time, you limit your successes to a max of 100%. With five balls running down five fields, we have a max of 500% chance of success. The only thing we have to do is five times more work.

Sometimes, we fail. I might go so far as to say that failure is the goal. In a parallel system, though, each project can benefit, not only from its own failure, but also from the perspective gained through the failure of other parallel efforts. This effect is especially pronounced in projects with common infrastructure requirements. As architectural obstacles are encountered, and solutions engineered, those solutions can be applied across multiple ventures suffering similar effects. This is all made possible through collective vision at the top management level. Without a cohesive perspective, parallel efforts fail to leverage each other’s strengths, to meet in the middle, as it were, and everyone is left high and dry.

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