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Everyone, at some point in their business life, makes the wrong call on a decision. Most often, they're minor calls with minor consequences. In those cases, you generally chalk it up to a lesson learned and move on with your life.

However, there are those times when you end up making the wrong decision and it unfortunately leads to a devastating result. Those are the ones that tend to follow you forever and serve as the moments you wish you could take back.

We asked entrepreneurs to share with us their worst decisions and the moments they wished they had a second chance:

1. "I was shipping my board games to a chain toy store in California. The owner complained about the shipping costs. I only charged the owner what I was charged by the freight company--but I made the decision of not absorbing the costs myself, or at least asking to split the difference. Huge mistake. I lost the business."

2. "I regret paying for an expensive marketing suite. My children's product was finished and I was looking for it to get more national attention. After a year of using the marketing suite, I am still paying off the credit card with not much return or sales to show for it. I would recommend that startups use a more focused approach and hire someone locally to help with PR for a specific purpose. This is my only regret."

3. "If I was to do it all over again, I would NEVER launch a business without a partner. Especially if it's a bootstrapped startup. You need someone who has the same goals, who can help keep you accountable, that isn't a financial drain on the company and who can help the yin-yang dynamic needed to launch a successful business.

Being a founder can be lonely. Might as well have a partner to help carry the workload--and the mental load of being a founder."

4. "One of my biggest regrets was foregoing vesting. I started my company with a long-time friend and his family friend, a lawyer. The lawyer wanted equity for his indefinite work (mistake #1) and then sweet talked me out of vesting (mistake #2), because we were all friends and could trust each other. I learned very quickly that friendships are broken a lot easier than binding contracts."

5. "I wish I hadn't started working on a huge specialty order for a very large grocery store chain before I received the official PO.

After dozens of hours getting setup with their system, ordering 5000 custom made packages and buying the raw ingredients to fill the order, they went radio silent. My buyer didn't even have the guts to tell me that they had changed their mind. It nearly bankrupt me and almost ruined my plans for growing the business.

Nine months later and I am almost out of that hole. I got greedy and paid the price. I will never build the order for a large PO without the official PO."

6. "I wish I had taken the job offer from Sheryl Sandberg at Google in 2003. I took the entrepreneurial path instead, which was very rewarding, but not as lucrative as a slot at Google Pre-IPO."

7. "I took on my best friend of 15 years as a business partner, and though she seemed sure she could handle the financial and time burdens of starting a new business, I felt less sure. I ignored my gut and brought her in as a co-founder of my business.

Within just months, she was no longer living up to financial or time commitments and was taking money from the business for personal use. Her leads and promises evaporated into nothing and both our business partnership and friendship ended.

That mistake cost me a friendship, $25,000 and months of catch-up and restructuring. Had I gone with my gut, the business would have been organized on much firmer ground from the very beginning and I would still have her as a friend."

Published on: Aug 26, 2014
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