Don’t Buy into Kevin O’Leary’s Definition of Success

Kevin O’Leary, the Shark Tank star and millionaire entrepreneur also known as Mr. Wonderful, ignited a firestorm over his tweet voicing his opinion about what it takes to become financially successful.

“You may lose your wife, you may lose your dog, your mother may hate you. None of these things matter. What matters is that you achieve success and become free. Then you can do whatever you like.”

You may lose your wife, you may lose your dog, your mother may hate you. None of those things matter. What matters is that you achieve success and become free. Then you can do whatever you like.

— Kevin O'Leary aka Mr. Wonderful (@kevinolearytv) February 11, 2023

After facing media backlash and criticism for encouraging monetary gain over family life and quality of life, O’Leary defended his views. Speaking to a talk show host, O’Leary said, “If you’re an entrepreneur, you know exactly what I am talking about. You’re going to work 25 hours a day, eight days a week. They wrote about it when the Beatles first put it out there. This is what it takes to succeed as an entrepreneur. If you can’t do it, if that statement makes you uncomfortable, don’t even try.”

Despite being roasted online, Mr. Wonderful doubled down on his opinion. “You’re going to sacrifice quality of life with your family in your early years. And the reason you do it, and what’s inherent in that statement is, you’re buying freedom for yourself and your whole family. That’s the whole idea.”

O’Leary’s words prompt us to reflect on the meaning of success and genuine freedom.

Many define success as the person who is living a first-class lifestyle. You have the best of everything. You can afford expensive, designer clothing. You drive the latest model car. You jet-set around the world. You eat in the trendiest restaurants. There’s nothing you want that you cannot have.

O’Leary suggests that you sacrifice love for the sake of money. You’ll catch up on the family life you have forfeited. Bad advice.

But lacking quality time with family, “losing your wife” while your bank account grows, does not qualify as living life successfully. After all, what do you have from all that money if you come home at the end of a workday to a dark home where the silence is painfully loud?

The happiest people on earth are those who have someone to share their life with. Sacrificing your spouse and your children for your fortune will not bring you fulfillment. How much pleasure can your most expensive attainment bring if you’re all alone?

There are some things money can’t buy: family, tenderness, serenity, and soul. O’Leary suggests that you sacrifice love for the sake of money. He believes that you’ll catch up on the family life you have forfeited.

Bad advice.

You can’t turn the clock back. I have met too many people who live with deep regrets over their life choices. Time is one of your greatest gifts. Once lost, there’s no way to relive the moment. There is no catch-up. Children grow. You’ve missed their bedtimes, their little league games, their childlike wonder.

Marriages move on. The many nights you spent away on business trips or catching up on emails and making the deal of your lifetime cannot be replicated. The endless energy you put into your work was redirected from your partner. You’ve disconnected. You’ve lost the ability to create boundaries. Is that success?

To O’Leary, this kind of success brings freedom. His freedom means that you have a credit card with no limits. Or you are free from having to spend time with a spouse or children. You can get into your convertible, the top down, music blasting, and there is no one to stop you.

Judaism has a different understanding of the meaning of freedom.

In Egypt, under the tyranny of Pharaoh, Jews were physically and spiritually enslaved. In Hebrew the word for Egypt is “Mitzrayim,” which means constriction, narrowness. Slaves are stuck in a confined, dark place with no ability to choose how to spend their time. Then came the miraculous moment of exodus. Jews were given the freedom of time, the freedom of living a life filled with fulfillment and purpose. For without purpose, what is life all about?

Today people are enslaved by a different form of constriction and narrowness. They lose themselves to financial success at all costs, working at all hours. They become weighed down by careers, laptops, and emails. Instead of discovering contentment and fulfillment, the incessant drive to make a fortune is a relentless, unforgiving taskmaster that slowly destroys one’s soul.

“A long life is not good enough. But a good life is long enough.”

O’Leary’s never mentions ennobling acts of kindness or striving to make the world a better place. Eight days a week means that you never have the opportunity to spiritually detox and recalibrate, to step away from the rat race and reconnect to all that you truly cherish.

After my father left this world, I was in my childhood home sifting through some of my father’s papers. On top of the pile was my father’s handwritten words: “A long life is not good enough. But a good life is long enough.”

Think about your definition of genuine success and freedom, and ask yourself: Will this lead you to living a life that is truly good?