Why Every Entrepreneur Needs a 2nd Startup

When your side project becomes your day job, pick up another side project
click an icon above to see more posts on that topic

Go To Comments

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.


Join Teaching Startup

Teaching Startup is a free on-demand digital accelerator for entrepreneurs at any stage.

INTERACT with other entrepreneurs.

LEARN from other entrepreneurs.

THE STARTUP SHOW to keep you motivated.

Get started by entering your email address. You'll get an email which will guide you through the rest.

Email Address
Caveat: By joining, you'll opt-in to our weekly email update. Cancel at any time.

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.

Q&A + Comments
You must be logged in to participate in Q&A or post a comment.

Your Email Address
Leave it blank to be anonymous
Your Thoughts?


Join Teaching Startup and we'll customize a lesson plan for you. Follow Teaching Startup and you'll get a heads up whenever we post new content. If neither of those appeal to you, here's some stuff we're guessing you might learn from.

If VCs Want To Survive, They'll Need To Evolve
Send me your pitch deck is very quickly being replaced by Send me your dashboard. And it's going to say a lot more about how fundable your business is.

How To Find a Problem For Your Solution
In Episode 6.7 of The Startup Show, we talk to NeuroPlus founder Jake Stauch about how his amazing brainwave tech struggled to take off until he found the right problem for his solution.

Tatiana Battles the Big Boys
In Episode 6.6 of The Startup Show, we discuss the challenges of taking on entrenched players in retail with Mati Energy founder and CEO Tatiana Birgisson.

Entrepreneur Isn't a Job
In Episode 6.5 of The Startup Show, we talk about how people who aren't entrepreneurs rarely understand what entrepreneurs do, let alone respect what we do. But it's also rare that they love what they do as much as we do.

How to Start a Company Outside of Silicon Valley
In Episode 6.4 of The Startup Show, we're kind of done with all the thinkpieces coming down from on high pleading that every startup ecosystem that isn't Silicon Valley should stop trying to be like Silicon Valley.

Pick a Topic
Get Educated

Teaching Startup has lessons -- written, video, and audio -- covering 25 important foundational areas of startup: Stages, Roles, Kinds, Funding, and Reasons.

Each lesson on the site covers at least one and up to five of these areas. Pick and choose what you need to know and how you want to learn it.

Click here. Choose a topic. Read, watch, listen, and learn