What I Learned Running Two Startups At the Same Time

And why almost every entrepreneur has at least two jobs

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.

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

Here’s the first thing you need to know.

Sharing resources: Same advice, different reasons

Whether you’re running two companies at once or running a side gig, never, ever use one company’s resources, time, and especially money and people, for the other.

The benefits of creativity and changing perspective

The truth is, if you’re truly an entrepreneur, and you want to be successful, you probably need the distraction of a second thing. You need that distraction like Coke needs Pepsi or Apple needs Google.

Transparency: Always be more honest than you have to

I’ve never done a side project that the world didn’t know about. An off-hours project that stays off hours is good for everyone. An off-hours project that bleeds into your day-to-day and has you constantly struggling is bad for everyone.

When to divest

If you’re good at what you do, at some point one of the entities will grow large and rewarding enough to force you divest from the other.

Can you hand the second company off?

In my newsletter I ask readers for their input into my next post. This response brought back a horror story from my past.

  1. You especially can’t do this with equity if you’re not 100% active in the venture. I understand that your time needs to be spent working on the first venture to fund the second, but even in that situation, you’d need to pay the employees of the second venture.
  2. I tried to hand off my PRIMARY priority company to start another company, and when the person I put in charge realized how hard it was to run that company without me, the lure of ownership was no longer worth it, and he bolted.

I’m a multi-exit, multi-failure entrepreneur. Sold ExitEvent. Building TeachingStartup.com & GetSpiffy. Former Automated Insights. More info at joeprocopio.com

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