‘The dead bird under the nest never learns to fly’: Kevin O’Leary once set up a trust fund for his kids — and it stopped giving them checks after college. 3 lessons that changed his life

Leaving the nest

O’Leary has frequently mentioned how his mother, Georgette, was one of the most influential people in his life.

She owned and managed a successful children’s clothing store called Kiddie Togs, which allowed her to support O’Leary through college.

However, when his mother visited him for his graduation ceremony, she informed him that the financial support was coming to an end. When O’Leary pushed her to explain, she offered him an analogy: “The dead bird under the nest never learns how to fly.”

As far as she was concerned, she had done her work — it was O’Leary’s turn now to leave the nest and support himself. The sudden lack of a safety net drove O’Leary to start making money independently, which eventually led to his many business ventures.

He said he now has a similar rule for his children which could motivate them to seek their own path to success.

These days, 65% of parents provide some sort of financial support to their kids between ages 22 and 40.

However, many wealthy investors and entrepreneurs subscribe to Georgette’s philosophy and limit the financial support they provide to their children.

Ingvar Kamprad, the founder of IKEA, famously didn’t leave the company to his family when he died in 2018.

Warren Buffett has a similar outlook. Buffett’s philosophy — to leave his children enough so that they can do anything, but not so much that they can do nothing — as he once explained, comes from the belief that the most important inheritance parents can offer their children is a solid example on how to behave.

While a safety net can be helpful, many successful entrepreneurs see the value in being self-motivated and seeking success independently.

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Guest speaker’s tip on experience

The second piece of life-changing advice came from a guest lecturer who appeared at University of Western Ontario during O’Leary’s final year.

The unnamed lecturer had some blunt words for the class, predicting that only a third of them would be successful while the majority would either fail or have mediocre outcomes in their career.

“He said, ‘You guys think you’re so damn good, don't you? Well when you walk out of here the real world is going to kick the living s— out of you and you won’t know what hit you. It’ll be brutal,’” O’Leary recounted.

He also said the lecture taught him about the value of gaining real-world experience, which has been instrumental to his business success.

“That experience is distilled to intuition,” he said.

“The only way to get to where I am today is having spent 30 years doing it, it’s the only way you can do it. You can’t buy it … you need the experience that the road traveled gives you. That turns into intuition and that becomes a very powerful tool.”

In 2023, 40% of business leaders surveyed by Intelligent.com said they believe recent college grads are unprepared for the workforce. This lack of tangible experience could be one of the reasons many young graduates struggle to find work.

Meanwhile, those with experience had a clear edge. According to a landmark 2018 study by Harvard University, the average age of people who founded the highest-growth startups is 45, challenging the popular notion that younger, inexperienced founders were more likely to succeed.

Stepfather’s tip on optionality

O’Leary revealed he’d initially wanted to become a cinematographer after graduating college. However, his stepfather talked him out of it.

Knowing that the industry was competitive and there was no guarantee of success, his stepfather encouraged him to complete his MBA, so he’d “have the toolset as an entrepreneur to choose any direction” he wished.

“And that was very good advice because it gave me time to mature a bit and learn the things I needed to know about running a business,” O’Leary added.

Many successful entrepreneurs had a similar safety net before setting off on their business journey. Buffett is a graduate of the prestigious Wharton school while Jeff Bezos reportedly once said he “would be an extremely happy software programmer somewhere,” if Amazon had failed.

Because success is never guaranteed, a backup plan could be invaluable for any investor or entrepreneur.