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Startups Anonymous: Founders Confess Their Worst Decisions

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[This is a weekly series that brings you raw, first-hand experiences from founders and investors in the trenches. Their story submissions are anonymous, allowing them to share openly without fear of retribution. Every Wednesday, we’ll run one new story chosen by Dana Severson, who operates StartupsAnonymous, a place for startups to share, ask questions, and  answer them in story-length posts, all anonymously. You can share your own story here.]

Every founder, at some point in the life of their business, makes the wrong call. 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 founders to share with us their worst decisions and the moments they wish they could take back:

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.”

 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 forgoing 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.”

[illustration by Hallie Bateman]

PandoDaily

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Startups Anonymous: Founders confess their deepest secrets

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[This is a weekly series that brings you raw, first-hand experiences from founders and investors in the trenches. Their story submissions are anonymous, allowing them to share openly without fear of retribution. Every Wednesday, we’ll run one new story chosen by Dana Severson, who operates StartupsAnonymous, a place for startups to share, ask questions, and  answer them in story-length posts, all anonymously. You can share your own story here.]

If you were to ask, you’d probably discover that most founders have a secret or two following them around. In most cases, those secrets are probably nothing more than just your run-of-the-mill, most embarrassing moment.

However, for some, revealing their secret could mean they’d lose the trust of their cofounders, confidence of their employees, or possibly their career.

On the other hand, remaining quiet can be damaging as well, especially mentally.

To give these founders an opportunity to free their mind and speak openly, we asked them to anonymously share what they’ve kept quiet. Here’s what they had to say:

  • I have OCD and ADD, but do a really good job of hiding it! I tell them I’m a great multi-tasker when truthfully I can’t focus on just one thing because of my ADD. OCD is a little easier to hide because it’s mostly germ related. I can usually find excuses to avoid sharing food and haven’t had to exchange much physical contact with my team. I do say I need to use the restroom frequently as an excuse to slip away and wash my hands whenever I am feeling contaminated. “
  • “My partners believe I’m an extrovert when really I’m an introvert. Not that big of deal, except I’m the face and voice of the company. I really, really hate talking to groups of people, which is a big part of my responsibilities.”
  • “My coworkers don’t know that, after closing time, I’m a stripper. Yes, a stripper, not a dancer. I take off my clothes and give lap dances for extra cash. It doesn’t affect my day-to-day work, but if word got out, it would be career suicide.”
  • I start everyday with a bottle of champagne and then make 10 phone calls I was too sober to make the day before.”
  • I am dyslexic. I can read and write and no one would ever guess, but try as I might, I’m famous for my random typos. I usually blame technology and make a joke out of it, but mostly I just don’t see things right when typing.”
  • “I was born into a single parent home. No one in my family went to college, in fact, most didn’t finish high school. I lived in Meadowview (in Northern California), dubbed “danger island” by locals. Danger island was full of drug addicts, drug dealers, gangs, and gang wars. Drive-by shootings and home invasions were commonplace. My brother was a Meadowview Blood. His gang activity resulted in our house being shot up–twice! My first sexual experience was at 15…forced at gunpoint. While I broke the cycle by completing high school, and enrolling in and subsequently finishing college, I was a young, unwed mother at the age of 20. I landed my first corporate job at Intel Corporation, excelled at the beginning of my career, then faced an unbreakable glass and racial ceiling. This was my catalyst to leave Corporate America and launch a business where I could own my own destiny. Little did I know I would be a pioneer in the natural hair care market!”
  • I’m deathly afraid of flying, but need to do it constantly for my work. The only way I can fly is when I’m drunk. Suffice it to say, I’ve had plenty of early morning flights and had to show up to meetings while I was hammered. I try to disguise it as best I can, but I’m sure that my clients can tell.”

[illustration by Brad Jonas]

PandoDaily

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