“My Biggest Mistake”

The folks on Fortune’s 40 under 40 list may be rising stars, but they’re not perfect. Here are the most regretted decisions from six of the most successful business people under 40. For young leaders to ignore the lessons they have learned would be just the beginning of a future regret.


Steve Stoute, Translation Advertising Founder

My biggest mistake was when I was a record executive I didn’t sign Alicia Keys as an artist. ([In my defense], she didn’t perform for me with a piano; I didn’t know she was a complete musician.)


Wendy Clark, Coca-Cola SVP

My biggest “almost” mistake was that I almost declined to interview with Coca-Cola. The headhunter said, “Are you crazy?” My husband said, “Are you crazy?” My mother said, “Get in there and dial that phone.” So I did. Thankfully.


Charles Best, DonorsChoose.org Founder

Deciding on DonorsChoose as our brand name. It works as a literal indication of how our website works, but it doesn’t stick in people’s brains. Folks often change it to “DonorsChoice,” and sometimes they simply can’t recollect the brand at all.


Raul Vazquez, Walmart.com CEO

When I was an engineer at Baxter, we developed a new cap for an iodine bottle that would save hundreds of thousands of dollars. We did a ton of analysis and were confident that the caps would work, so we decided to make the entire change at once.

Then, we started hearing reports that the caps were leaking — it was very stressful. I learned that it can pay to be patient, and do things in a planned, rolled-out fashion.


Rio Caraeff, VEVO President and CEO

When I was much younger, I was traveling on a business trip when a close family member passed away at home and I decided to not travel home for the funeral as I had made the decision that my work was more important at the time. I look back in regret at that decision frequently and have now since realized that family does come first.


Premal Shah, Kiva President

I got some great advice once: “The relationship trumps the issue.” Like a lot of entrepreneurs, and especially social entrepreneurs, I get pretty fired up and attached to my own viewpoints. At times when I have disagreed with someone, when the stakes are high, I can take it personally and it’s added distance between me and the person. Remembering that the relationship trumps the issue is key.

1 Comment

Filed under Leadership, What I'm Learning

One response to ““My Biggest Mistake”

  1. Hi, I found this blog post while was searching for products related information on yahoo and found it very good article, thanks for sharing, best regards and cheers!

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