Being a Startup Founder Sometimes Feels Like Being Alone in a Cave and Looking Out.

8 Reasons Why Startups Don’t Succeed

Cynthia Wylie
7 min readAug 20, 2018

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I am a founding member of an active startup founders group. We started with a dozen or so entrepreneurs and I appreciated it because being a startup founder without a partner can be a lonely endeavor. I’ve seen a lot of fellow entrepreneurs walk in and out of the doors over many years. I can now tell if someone is going to “make it” after about three meetings. Here are my observations of why they eventually don’t succeed:

1. They don’t show up. If you want to be successful, you have to show up. I mean that literally and figuratively. You have to show up on a consistent and regular basis. Even if you are tired and can’t seem to find your customers, you are not booking sales, you are getting rejected and you know deep inside your gut that you probably have to pivot your plan, even though you are exhausted. You must keep going — putting one foot in front of the other, executing the marketing plan, calling on customers, pivoting if necessary — you just keep at it. Do they show up on time? If you can’t show up at our meetings on time, what about their business meetings? What if you have a meeting with a venture capitalist? Are you going to be late? Are you going to flake and not show up? Because you and your husband had a fight? Being a C.E.O. of your own startup company is being a self-starter in the truest sense. If you aren’t 100% committed to this, you just won’t make it.

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Cynthia Wylie

Founder of Bloomers Island. Published children’s book author at PRH. Writes about big kid’s stuff like economics & business, too. TheProjectConsultant.com.