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Seven Highly Successful People Share Their Biggest Financial Regrets

Let’s face it. When it’s about your hard earned money which is to be spent, nobody is proud of it.  Taking pride in spending money is useless. It doesn’t get you as much as you give away.  We all have done things that we aren’t proud of with our money. Whether it’s about selling the stock right before the prices are about to skyrocket OR even shying from negotiations for a salary raise or even dragging your heels to open a retirement savings account. Even the best of us are in the habit of making mistakes. It is inevitable. Successful people are also counted in the list of people who’ve made mistakes.

7 CEOs, multimillionaires, and executives were interviewed to find out which one of their financial choices forced them to not sleep at night.

Read on to find out in what manner did these high achievers answered a single question, “What is your biggest financial regret?”

01. Tony Robbins, the multimillionaire life coach: 

“I have a resort in the town of Fiji, and there was this small company that bottled water. The bottle had a very calming appearance, cool if you must, and the water tasted exceedingly well- you could pinpoint the difference. After that, I hired a guy to give me some research on the business. He was per say, an ‘expert’. And I said, “I think I could purchase 30% of this company for at least half a million dollars. I think I can make an investment out of this”. “He soon came back to me and said that they don’t have the ability nor the resources to make it. I accepted that without doubt. Now, whenever I grab a bottle of Fiji Water, I say to myself, ‘Holy Shit!”. Lesson- uses your experts as your coaches and dug in deep yourself.

02. Ken Lin. CEO Credit Karma just reached a valuation of $1 Billion: 

“In 2008, I bought shares of a company called WaMu two days prior to their collapse. Then, I thought that it was panicked selling and that as a bank, WaMu wouldn’t or couldn’t go any under. Visibly, I was wrong and foolish. But, it did teach me a valuable lesson about how anything can change so quickly, in a blink of an eye.”

03. Jon Stein, CEO and Founder Betterment: 

“I wasted a lot of money and time over thinking investing. Whether it was about opening a wholesome of brokerage accounts, or getting too strenuous in single securities, and trying to achieve transactions that were too complicated. All of it was a waste. Opting for the index route in my yesteryear would’ve put me in a better position for retirement. I would have also been able to spend more time with family and friends.” “The money is on one side, but I would never be able to get back those 100s of tenuous hours that I wasted in an attempt to beat the market.”

04. Sallie Krawcheck, former Wall Street Executive and Chair of Ellevate Network: 

“The biggest financial regret I have is being pushed into accepting a particular job and not being honest about it. While not being able to work diligently, I couldn’t complete the set of desired tasks asked out of me”. “I was responsible for turning the business around. I only met the CEO and three other people at the company. I was not allowed to meet my peers because they didn’t know of my hiring; I wasn’t allowed to meet the board either. Because ‘we don’t do that.” “All the CEO told me that he had two more years at the company and that he would help me with my transition.  It was also told to me that the announcement for the same had to be made quickly because it was a part of a company-wide reorganization. Due to this, my agreement was being negotiated and discussed until after midnight the actual day of the announcement. We agreed to shake hands on the financial aspect of it.” “What could go wrong? The outcome is a no-brainer: the CEO was out after a few months. This made it my biggest financial mistake throughout my life and by a good measure.”

05. Kip Tindell, chairman, Co-founder, and CEO of The Container Store: 

“When I was young, my wife and I had no money. We could’ve bought this piece of land in Telluride, Colorado.  We hoped to open a little wine and dine place. It didn’t cost much- about $55,000. It could’ve been a very good investment for us.” “If only we could’ve figured out a way to gear up the money, we could’ve expanded exponentially. Telluride soon became Telluride, and now Oprah Winfrey owned a piece of land there. Thus, I regret that, but I’m also glad that I didn’t go for it otherwise there wouldn’t have been a Container Store. I’m glad about the financials of this company.”

06. Scott Adams, Creator of long-running comic strip Dilbert: 

“Early in my career, when I was super-busy, I allowed many professionals at the bank to take care of half of my money for me, given that they would dig deep into the companies and perform research before investing”. “They bought in my stead WorldCom, Enron, and a few other ‘gems.’ I learned it the hard way that professional wealth management is just a scam, and this goes not only for my guys.

07. Ron Shaich, CEO and founder, Panera Bread: 

“From a personal aspect of life, my biggest ever financial regret has been selling my stock of Panera Bread because this has been the most major asset of my life.”

Muzahed I.
Muzahed I.
I am Muzahedul Islam. Executive Editor of Reach me out for writing opportunities on this website.
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