Using side projects to have fun, build skills, develop relationships, and maybe your next company…

Starting a company is hard. The variables of selecting the best idea, finding co-founder(s), unknown duration of customer discovery, product/market timing, and financing strategy/timing makes it even harder. And, starting a company takes skills, functional practice, and a little luck. In my experience, a good way to get started in all of these areas is by doing a “side project.” I’ve done this many times with success including Rival IQ, my most fruitful side project to date.

Firstly and perhaps most importantly, keep your day job while you work side projects. Sure, one of them might turn into a company at which point, you can focus on it full-time, but wait until that is absolutely necessary. This gives you infinite financial runway and will force you into doing the most important things in your limited off-hours. This will be true for your other co-conspirators too. And, while you might not think you have the time, you and your founding team should get used to working on nights, weekends, and lunch breaks to get everything done. It’s just another part of the “startup training” regimen.

If you are functioning as the “CEO” (read more about the 5 jobs of the CEO here) it’s your job to set out the basic vision for the project/idea and plan. It’s also your job to set up the conditions for your team to work together and succeed. Here is where some structure makes all the difference;

  • Set the right expectations – doing side projects is more about hanging out with fun, interesting people, making things, and learning. Like playing in a band. Sometimes what you make finds a great audience and can deliver commercial success, but side projects should feel more like jam sessions vs. trying to be a successful rock band, at least when you start out.
  • Outline the vision for what the offering should be. Using my simple CVFB method is a good way, but you can use Lean Startup or Business Model Canvas too, I just find them too “heavy” for a side project. Knowing what you want to build, for whom is pretty important and will help you make progress toward a real thing and audience. Be open to modification of the vision on a weekly basis. Read it and refine it and restate it, every week as you set and reset direction and activities. (this is another part of leadership and structure).  If you’ve picked right, there is usually limited modification and the same CVFB might last years, but when and how you perservere or pivot is important.
  • Set time and commitment expectations from everyone – I like to suggest 3-5 hours/week for everyone on the team. This would include one hour of planning (what are we going to do for the week), 1-2 hours of working together/collaborating on key deliverables, and 1-2 hours of everyone’s personal time working on personal deliverables. If someone on the team has more time and wants to spend it on the project, make sure the others don’t feel guilty about their level of commitment or time. Five hours/week times multiple team members can make pretty massive progress.
  • Develop a weekly working cadence – I suggest something like “we meet on Tuesday nights from 6-8, then we squeeze in the additional three hours when we can during the week.” You could set up a “check-in” on Friday as people are likely going to be doing work over the weekend and you want to show up on Tuesday with all the work completed so you can start again the following week.
  • Give people an “out” – As you meet new people you want to bring onto the team, encourage them to just commit for one month or four “sprint weeks.” And, at the end of the month, everyone can evaluate how it’s going and if people aren’t having fun or learning, it’s totally fine to “break up” or leave the project with no hard feelings. This monthly cadence will also allow the team to reset a vision, what they might want to achieve given the team they have, and how well the project is progressing. There are many reasons why people might want to leave; they don’t like the team, they don’t like the direction of the project, they don’t have the relevant skills needed, they can’t manage the time commitment…but as the leader/CEO, you need to make it easy for people to join and to leave without stressing them or the rest of the team. Remember this is a side project.
  • Know when to quit/pivot/restart – most ideas don’t work, usually due to customer demand — you just can’t find a set of early adopter customers who really want your thing and are willing to pay for it in the way or amount you imagined. You need to spend enough time trying to find out. Who knows how much time this might require, so the monthly cadence of “what are we doing, why, for whom…(CVFB) and the personal team commitment (are we having fun hanging out, doing this work and do we want to continue) is a good forcing function. Sometimes teams disband, sometimes they kill one idea and start working on another, which might mean some members of the team want to leave…all of this is good learning and good to reflect on during the first meeting of the month.

I give this advice to lots of people and a few years back, I gave a talk to a bunch of entrepreneurially-minded students at Purdue’s Anvil (the hub of entrpreneruship) with similar recommendations. I recently connected with my friend Akash Raju, who led many of the entrepreneurial efforts at Purdue and has used this approach to launch his new company, Glimpse which made it into and just completed YCombinator. It worked for him and it’s worked for others too!

For me, Rival IQ was a side project that turned into a successful, venture-funded company. How to Live to 200, our podcast about health, longevity and human performance started as a side project, we recorded a bunch of episodes and then “paused” mode when we all got too busy. PersonalScience is another one, in this case, we had many people come in and out and I left the project when I joined PSL, and Richard and the remaining team continue to drive this forward. Prepared, “a better way to prepare for your business meetings” is a side project for me that I am still dabbling with so feel free to sign up, test it out and give me feedback. Each of these gave me a chance to hang out with smart, motivated people I wanted to spend more time with, in a low stakes kind of way. We learned new things, we learned about each other and we made some cool products. Give it a try yourself.

PS – if you’re a rockstar software developer or product designer and want to consider a side project with me, I have lots of other ideas! Send me an email –

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