“The Biggest Mistake I Ever Made”: Stories From 5 Women Entrepreneurs

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Every accomplished entrepreneur has their fair share of horror stories, no matter how successful they have been. Maybe it’s a story about the big hire that flamed out after just three weeks; an early deal where they lost big-time; a partnership they entered without a written contract that blows up in their face. Any successful entrepreneur has big mistakes in their past.

Hearing great advice from entrepreneurs who are at the top of their game is always great, but sometimes the most impactful lessons we can learn from them comes from hearing about these mistakes. Indeed, many view their personal failures as the most valuable experiences in growing their businesses – and aspiring entrepreneurs can learn from those experiences, however painful they were at the time. I asked 5 women, all of whom I admire greatly, about their biggest entrepreneurial mistakes – and how they made it to the other side.

Sheila Lirio Marcelo, Founder, Chairwoman and CEO of Care.com

We knew demand for Senior Care would be huge, and surveys and demographic data showed that. But when we launched a service in 2010 live in production, we found it was too early for consumers and had to shut it down quickly. There are many decision points along the way and we often go through a logical analysis, but it is important to figure out how to structure a small lean test live in production before investing significantly in something.

Named one of the "Top 10 Women Entrepreneurs" in Fortune Magazine, Sheila Lirio Marcelo founded Care.com in 2006. It has grown into the world’s largest online destination for finding and managing family care, with over 22 million members across 19 countries..

Alexa von Tobel, CFP, CEO and Founder of LearnVest.com 

“Many entrepreneurs live by the motto ‘go, go, go,’ especially since technology makes it so easy to stay connected to the office. I was certainly one of them.

But the hard truth is, you can't kill it on the job if you're not looking after yourself once you clock out—or if you're simply failing to clock out in the first place. I used to think it was selfish when I took time for self-care (think: gym, doctor’s appointments, vitamins, sleep). But I eventually realized it was actually vital. The more calm and collected I am, the more strategic I can be, and the better off my company is. When you're leading the charge, it's easy to skimp on sleep and exercise and forget about healthy eating.

But the more you have on your plate, the more essential those things become!”

Alexa von Tobel launched LearnVest in 2009. She was Named “One of the Coolest Young Entrepreneurs” in Inc. Magazine’s 30 Under 30, and is the author of the New York Times Bestseller Financially Fearless.

Linda Rottenberg, Co-founder and CEO of Endeavor Global 

“Starting out as a young CEO, I used to mistakenly think it was my job to sound steely and imperious all the time and to not betray any weaknesses. Then, one day I showed a draft of a showy speech I had written to my husband, Bruce Feiler (a writer and columnist, so he knew what he was talking about). He promptly tore it apart, saying ‘too much Superman, not enough Clark Kent.’

Unfortunately, it wasn't until Bruce got diagnosed with cancer that I finally heeded his advice because I had no choice – I couldn't hide my emotions from my colleagues and employees, so I let it all out. Much to my surprise, they respected me more for it! Since then I have strived to be ‘less super’ and ‘more human,’ which means exposing my vulnerabilities, embracing my flaws, and copping to my mistakes.”

Named one of “America’s Best Leaders” by U.S. News and one of TIME’s 100 “Innovators for the 21st century,” Linda Rottenberg is considered among the world’s most dynamic experts on entrepreneurship, innovation, and leadership.

Jennifer Manaavi, CEO and Co-founder of Physique 57

“Physique 57 had early success which we were happy about. We opened three studios within two years. The third location was twice the size of the first and I was not prepared for the onslaught of clients and commensurate operational issues. What I found was that I did not fully plan out the logistics of running three studios. I underestimated the need for a larger team and the need to better organize the team. Every employee was working too many hours and juggling too many responsibilities. While it was an exciting time for the business, the gang was exhausted and overwhelmed.

I hired an HR consultant to focus and align the management team, and I still work with him nine years later.

Jennifer Maanavi launched Physique 57, an international fitness company that promotes physical health and personal empowerment through dance-inspired exercise, in 2006.

Courtney Nichols, Co-founder and Co-CEO of Smarty Pants

“My biggest mistake was trying to save money by not hiring a headhunter for a couple of senior-level hires. When you are micromanaging cash, it feels like a luxury, so we did it ourselves and picked the best candidates from a limited pool. Even though we were not new to building businesses, we were new to consumer-packaged goods. So we should of been hiring people smarter than us in their respective fields.

My approach was a perfect example of “penny wise, pound foolish,” and I paid for it in spades when I had to step back in and start running parts of the business myself while we backtracked, hired a search firm, and replaced a couple of key roles with a better fit. Anyone who has run a high growth company knows the amplifying effect of not having the right people – the downstream impact is massive. Fortunately, we came through it fine, but it was avoidable.”

Courtney is the Co-Founder and Co-CEO of SmartyPants, a health and wellness vitamin company that was listed as one of Inc.’s 500 Fastest Growing Companies of 2015


JJ Ramberg is​ co-founder of Goodshop.com. Their browser plugin automatically activates the best coupons when you shop online.