Why Every Entrepreneur Needs a 2nd Startup

When your side project becomes your day job, pick up another side project
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In Episode 6.1 of The Startup Show, Joe Procopio (Automated Insights, ExitEvent), Andy Roth (RocketBolt), and Jon Colgan (Veeto, Cellbreaker) propose that all entrepreneurs need two things to work on at the same time.

A lot of entrepreneurs get started by building their own business on the side while still working at their day job full time. This is a hard path to walk, but for the sake of creativity and motivation, every entrepreneur should continue on with a 2nd thing, something between a hobby and job, once their startup becomes their full time job.


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While Joe was building Automated Insights, he had already started working on a side project, ExitEvent, to help consolidate and strengthen his local startup community. Somewhere along the way, ExitEvent started making money and became something like a 2nd startup. Joe was able to use concepts and ideas from one startup to help the other, and it also gave him an escape, something to put another side of his brain on for a little while when things got complicated.

Teaching Startup is actually the 2nd thing for all of us, including the guys who shoot and produce The Startup Show, and it's paying dividends for everyone. We get to experience doing startup with other entrepreneurs, and since Teaching Startup is a startup, we're all gaining an education on concepts we might not come across in our "day job" startups.

Furthermore, because Teaching Startup still walks the fine line between side project and full-blown startup, we kind of skipped all of the logistical elements of starting a company and went straight into building a beautiful product. Joe likens it to a flaming car speeding down the road.

But the Teaching Startup team was chosen carefully, the product is being painstakingly constructed, we're constantly mindful of whether or not we're providing value. Since it's still indeed a 2nd thing, we can experiment a little more and take more risks. Then we can take those lessons back to our first thing.

There are drawbacks, of course. We're all aware that our 2nd thing is going to have its own problems and headaches. We have to be very careful that our 2nd thing doesn't turn into a 2nd mess, and that includes caution when making commitments or setting deadlines that we might not be able to keep.

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