I met with a few entrepreneurs recently who left interesting companies to pursue their own ideas.  In both cases, they wanted to experiment with a number of different concepts and had plenty of runway to figure out where they ultimately wanted to devote 110% of their efforts.

This is an exciting and liberating time for an entrepreneur.  The world is suddenly your oyster, and it’s a time to start exploring brand new industries and problems.

The problem is that these expeditions often end fruitlessly.  It’s also very hard to “force” inspiration to strike when it could happen anywhere at any time.  Now that an entrepreneur is a free agent, how does one come up with an idea or decide what kind of company to start?

I was able to chat about this a bit with a friend of mine who is a 4x serial entrepreneur.  He is in the midst of one of these searches now, but gave some pretty interesting guidelines that I thought were worth sharing.  I originally had a few points I thought were interesting, but ultimately realized there was just one major lesson:

Don’t “brainstorm and filter”.  Operate in short sprints. 

It’s very natural for people to try to collect a bunch of ideas up front, filter them based on some research and/or personal conviction, and then choose a few to try to pursue simultaneously.  It’s a decent way to start, but the pool of ideas dries out quickly.  I find that few good companies originate out of a brainstorm-and-filter approach.  Couple issues: 1) too theoretical.  2) too easy to kill an idea when it’s an idea.

Instead, operate in short sprints.  You do do some idea generation of course, but the goal isn’t to decide what you are going to work on for the next few months.  The goal is to figure out what you want to devote 1-full day on.  It’s amazing how much you can accomplish in a day – talking to customers, reviewing competitors, trying substitutes, etc.  Also, the bar is low.  A lot of cool ideas are worth one day of exploration and real diligence.

If that goes well, decide whether to invest a week on the concept.  Again, it’s amazing what you can do in 1 week – do a quick customer acquisition test, take users through hand-drawn mockups, talk to more customers, etc. 

If that goes well, decide whether to invest a month.  And so it goes.  Many ideas won’t make it this far, but the idea is to engross yourself into something and know you are only investing a day or a week.

There are many benefits to this approach but the most important is that it maximizes learning-by-doing.  That’s not only the best way to begin building a company, but it’s also the best way to encounter new problems that may not be obvious at first blush.  I really really believe that inspiration for companies come from authentic needs that one faces or experiences in their personal or professional life.  Doing these sprints allow you to get deep enough into a project to uncover other needs or problems that aren’t as obvious to someone who is “brainstorming and filtering”. 

An entrepreneur may even want to go as far as doing some advising or work 1-day a week with a company in a completely new or unrelated sector.  It not only helps with some of the loneliness of the process, but it also allows you to be exposed to a brand new set of problems that you probably never knew existed.  Especially for an experienced entrepreneur, a lot of companies would be excited to have a little bit of their time in exchange to the opportunity to encounter new authentic problems.