9 Confessions From a Failed Startup CEO

A business degree, Wall Street background, and prior startup experience couldn’t save me from these grave mistakes.

Rachel Greenberg
Entrepreneurship Handbook
10 min readMay 12, 2021

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startup ceo planning and failing
Photo by Startaê Team on Unsplash

I knew something was wrong when I couldn’t get out of bed until 9, then 10, then 11 am. I had spent the prior years working 80 to 100-hour weeks in high-pressure investment banking jobs pitching and…

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Wall Street Investment Banker → Entrepreneur & Startup Consultant. “Top 10 Entrepreneurs of 2020” Yahoo Finance. CEO of Beta Bowl. Mom of 3 furbabies ❤