"I have a resort in Fiji, and there was a little company that bottled water. The bottle looked cool, and the water tasted really incredible — you could tell the difference. I hired a guy to give me research [on the business]. He was a so-called 'expert.' And I said, 'I think I can make an investment in this. I think I can get 30% of the company for half a million dollars.'
"He came back to me and said they don't have the resources or capacity to make it. And I accepted that. I look back on Fiji Water and anytime I grab one I say, 'Holy shit!' So use your experts as coaches and do your own homework and dig deep."
"In 2008, I bought shares of WaMu two days before they collapsed. At that time, I thought that it was panicked selling and that a bank like WaMu wouldn’t or couldn’t go under.
"Clearly, I was wrong. It did teach me a valuable lesson about how fast things can change in business."
Jon Stein, founder and CEO of Betterment:
"I wasted so much time and money by overthinking investing. Whether it was opening a dozen brokerage accounts, getting too concentrated in individual securities (thanks Enron), and attempting to do overly complicated transactions — it was a waste.
"I should have just taken the index route in my younger years. I'd be in a better place for retirement now, and I would have been able to spend more time with friends and family.
"The money is one thing, but I'll especially never get back the hundreds of hours I poured into trying to beat the market."
Being rushed into a job.
Sallie Krawcheck, Chair of Ellevate Network and former Wall Street executive:
"My biggest financial regret is being rushed into accepting a job and thus not being allowed to do full due diligence or get the details fully set.
"I was brought in to turn around a business; I had met the CEO and three others at the company. My requests to meet some of my peers were denied because they had not been informed of my hiring; my requests to meet members of the Board were denied because 'we don't do that.'
"The CEO told me that he would stay in his job for two years and that he would help in my transition to the company. I was told that the announcement had to be made quickly because it was part of company-wide reorganization that was tee'ed up; thus my agreement was being negotiated until after midnight the day of the announcement. Our financial agreement was not a guarantee but a 'handshake.'
"Gee, what could go wrong? You can guess the outcome: The CEO was gone a few months later. And this turned out to be the biggest financial mistake of my life ... by good measure."
Kip Tindell, cofounder, chairman and CEO of The Container Store:
"When were young, just married, [my wife] Sharon and I didn’t have any money. We could have bought this piece of real estate in Telluride, Colorado. We wanted to open a little food and wine place. It wasn’t much money — about $55,000; it would have been a great investment.
"If we had figured out how to wrestle up the money, it would have grown exponentially. Telluride became Telluride, and even Oprah Winfrey got a place there. So I regret it. But at the same time, I’m glad I didn’t do it, or I wouldn’t have started The Container Store. And I’m so proud of the financial performance of The Container Store."
Letting other people have complete control over your money.
Scott Adams, creator of long-running comic strip Dilbert:
"Early in my career, when I was super busy, I allowed professionals at my bank to manage half of my money for me under the promise that they would do deep in-person research on companies before investing.
"They bought for my account Enron, WorldCom, and a few other gems.
"I learned the hard way that professional investment management of the stock-picking kind is a scam. (Always. Not just my guys.)"