17. Why would you start two businesses when starting one is hard enough already?

Thinking about launching a product or service and building a company around it? Here’s an extra thought for your consideration: why not start two? I will caveat that this is likely not a good idea. But let’s humor it for a second, as I think you can make a plausible argument for having two projects at the very beginning of starting a business rather than one.

  1. Working on multiple concepts can help prevent “dog-on-a-bone syndrome.” Starting a business is really hard and is mostly a low-likelihood-of-success proposition. And it hurts like hell when you pour yourself into something, and it doesn’t work or people don’t react to it in the way you hope they will. It starts to feel very personal. It is a normal reaction to retrench. But that turns out to be mostly non-constructive. The intellectual flexibility instead to allow at least for the thought that says “welp, we learned something and can now incorporate that learning into what’s next” is really valuable. When you launch a new product then, even the smallest of side projects will help force you into a broader mindset. It will give you just one more perspective from which to evaluate your outcomes. It will force you out of blinders-on tunnel vision. It will put even a tiny little bone next to the one you’re chewing on, which in turn will force you to consider even briefly whether doubling down on your current one is the best alternative. This is healthy and worthwhile (even if it will sound a lot like not “going all in” which is in itself also important).
  2. Repetitions are really important, and different products will have more in common than you think. When you’re creating services, it’s amazing the similarities that are shared between what would otherwise seem like very different projects. Experiencing these similarities (and not just intellectualizing them) is very valuable. Working on at least a side project then while starting a business can help you compile a perspective on what you personally or as a team do best, what tools are most effective, etc. And you can have confidence in those perspectives because you have seen them play out in more than one context. This is especially true for first timers. You may not know what you know until you have been forced to apply yourself to more than one problem or solution.
  3. Tired thinking is not always cured by thinking more. There are times when working harder is the solution. When you’re creating something from nothing, this will be true as it relates to getting to market more quickly, speaking with more customers, doing the unscaleable things that you need to do before you build systems to scale them, etc. Thinking more about your thesis and the specific fact pattern that you have in front of you will not always add clarity. Clarity instead often comes from thinking about something else, even if just for a day at a time. Creating that kind of separation between your mind and its pet creations can be exactly what you need to realize which of your ideas is misguided and which actually might have legs. It can help you recalibrate priorities and regain focus on the bigger picture. There are of course other ways to do this than having a side project or second business. But for those who want to feel like they’re always (or almost always) being productive, those vehicles are good ones for achieving this outcome.

Not saying that this as a generalization is good advice. But the thought process should be undertaken, especially by first time founders, because the problem of stale, singularly focused, perspective-less thinking can be very real and is hard to diagnose once you’re down the rabbit hole.


Note to reader: This is day 17 of 92 in my commitment to write for 30 minutes each day from October 1 through the end of 2015.