This article by VerticalResponse CEO and founder Janine Popick originally appeared on

I went to a great tech event called VatorSplash. It’s an event where tech entrepreneurs claw their way to center stage in hopes of getting their demo seen and receiving the coveted Vator award. The real benefit is they get in front of some impressive VCs that might love their idea enough to fund it to the next phase. The night I went, I was lucky enough to get to listen to the CEO of Evernote, Phil Libin speak. And as I write this, I’m using his great tool.

Libin walked us through his beliefs on entrepreneurship; specifically who should be an entrepreneur and where they should launch. As he chatted about the “who” part, I pulled four reasons why anyone thinking they want to start a business should NOT DO IT and related it to my day-to-day and boy, was he spot on. So here’s my take on his words. Don’t start a biz if…

1. You Want to Be Your Own Boss

In general, most boss’s report to someone on some level. Yet even if you fund your company yourself, you still have people to answer to. You need to understand that your No. 1 job is making sure people in your company are successful. I have a bunch of people who report to me at my VerticalResponse. Their biggest problem? Getting s*it done. My to-do list? Removing obstacles for them so they can get stuff done, which benefits our team. I report to them and they know that.

2. You Want More Flexible Time

It’s such a great thought, “If I have my own company I can come and go as I please!” (LOL). For what it’s worth, if you want more flexible time, you should not be an entrepreneur. As I sit here at 9 p.m. writing this, I owe this article to the person who manages content for us. (see No. 1). You live and breathe your business, you can’t think of anything else and your time is your business. Get used to it.

3. You Want to Make Money Overnight

When I started VerticalResponse, I wanted to commoditize email marketing for small business. In 2001 there wasn’t a tool for small businesses to do their email marketing affordably, so I wanted to ensure there was something reasonable that would help their business grow. Do I want VR to be successful? You bet, whatever format it comes in, be it an acquisition, IPO or simply making it on its own.

4. You Can’t Afford to Fail

If you want to start your own business, you have to be okay that you’ll lose your own investment. And if you’re lucky enough to have them, you’ll lose your investors investment and you’re still okay with that. If you’ve got a soul, you’ll lose sleep. For me, every time I went back to my friends and family for investment money, I made sure to put my money where my mouth was and invested alongside them. I couldn’t see taking friends money if I wasn’t willing to put more in myself!

All in all, a great gig, thanks Phil for an awesome chat, and for bringing to the surface the realities of running your own business. What you talked about was complete reality, but I wouldn’t trade if for the world!

Do you agree with who should be an entrepreneur? I’d love to hear about it!

© 2013 – 2018, Contributing Author. All rights reserved.

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