What I Learned Running Two Startups At the Same Time

And why almost every entrepreneur has at least two jobs

Joe Procopio
7 min readOct 22, 2020


Should you quit your day job to start your own company?

Should you shelve an existing startup to pursue a new startup idea?

Let’s knock the elephant out of the room right away. If you’re uncomfortable juggling two high priorities at the same time, entrepreneurship is going to be a very uncomfortable lifestyle.

Unless you find a way to make it work. I can help with that.

Why entrepreneurs end up running two companies at once

For the longest time, I thought I was an outlier. Looking back on a 20+ year career as an entrepreneur, I can count at least five times I found myself actively running two companies at the same time.

Every time it happened, I believed it to be a simple case of bad timing: Two opportunities would gel quickly in parallel. Or a succession plan blew up in my face. Or I found myself caught in a fun little opportunity that turned into a job.

Turns out I’m not such an outlier. In fact, since I’ve been advising other startups, I get this question at least once a month:

“How do I run two startups at the same time?”

And I get this question quite a lot too:

“How do I know when to quit my job and run my startup full time?”

Look, I don’t want to be the guy that preaches against loyalty, whether that loyalty is to the people you’re paying or the people who are paying you. But I will tell you this:

If startups were only founded when the timing was right and all the conditions were perfect, no one in their right mind would ever start a company. Opportunity doesn’t check to see if you’re dressed before it knocks.

Almost always the first question: How do you split work time?

Here’s the first thing you need to know.

Running two companies at the same time is almost exactly like having a full-time job plus a side gig, even when considering where to prioritize your time. There’s no “choosing”…



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building TeachingStartup.com & GROWERS. Write at Inc.com and BuiltIn.com. More at joeprocopio.com