I’m often asked what I would do if I had to start over – without a penny in my pocket – and re-make my millions from scratch.
My answer? I’d still be an entrepreneur – and not because it’s the easiest path to wealth.
In many ways, entrepreneurship is the riskiest way to make a living and it certainly isn’t the only way to become a millionaire.
Two-thirds of the population will choose the safer course: the nine-to-five job. With hard work, a focused investment strategy and a little luck, most people should be able to build a million-dollar nest egg by the time they retire.
It takes time, discipline and patience, but it can be done.
Entrepreneurs are different. We’re risk-takers. Personally, I like knowing that my destiny is in my hands. For if an entrepreneur can identify a market demand and meet it, they’re capable of reaping the fruits of their labor very quickly.
So, here’s my advice to anyone contemplating a fresh start:
I’m often asked what I would do if I had to start over – without a penny in my pocket – and re-make my millions from scratch
Skate to where to money is going
To paraphrase a great Canadian philosopher: skate to where the puck is going to be, not where it is.
These wise words, often incorrectly attributed to Wayne Gretzky, originated with his father Walter. They are as true in business as they are in hockey.
If I were just starting out as an entrepreneur or investor, I’d have my eyes on where the money is going.
Earlier this month, Meta – owner of Facebook and Instagram – announced that over the next three years it expects to spend $600 billion on the infrastructure that runs artificial intelligence. On Thursday, the company pledged $1 billion to build a data center in Wisconsin. Microsoft spent almost $35 billion on AI data centers in 2025 alone.
All 11 sectors of the US economy now use AI as a tool to reduce costs and enhance margins, but none of this is possible without infrastructure, the land to build it on and the energy to power it.
I’m focused on AI infrastructure and the land that is necessary to build and power AI, because I believe those investments will provide the most extraordinary returns for the next 20 years.
All 11 sectors of the US economy now use AI as a tool to reduce costs and enhance margins, but none of this is possible without infrastructure, the land to build it on and the energy to power it
Learn to fail
The greatest fault that I see in young entrepreneurs can, ironically, be disguised as their greatest strength.
Driven people can become so enamored with an idea that they pursue it against all odds, overcoming seemingly impossible barriers and tuning out the naysayers.
Indeed, successful businessmen must live and breathe their ideas, but that impulse can also be destructive.
The brutal reality is that 80 percent of start-ups fail. That has been the case in the United States since the 1950s.
Entrepreneurs – and really anyone trying to build a life for themselves – need to know how and when to call it quits. I’ve seen people continue to push an idea, even after the market tells them that it is a dud. But they keep going, even to the point of bankruptcy.
Develop the ability to step outside of your own mind, read the room, listen to the market, take good advice and realize when you need to abandon an idea and try something else. Often you’ll strike gold on the second, third or fourth attempt.
You’re going to be wrong far more often than you’re right. Rather than seeing failure as a deterrent, let it be a teacher.
Making education count
I’ve recently had a change of heart when it comes to education. I used to say that the only post-secondary degree that is worth pursuing was an engineering degree. But that’s not the case anymore.
The highest growth rate in terms of salaries and compensation is occurring around creative storytelling and social media.
Businesses are recognizing that they can reduce their customer acquisition costs and increase their return on ad spending by employing talented story tellers. And they’re willing to pay these people a lot of money.
In my experience, some of these social media ‘artists’ won’t even take a job because they can work simultaneously for multiple different companies and can make four times as much.
The old adage is, indeed, true again: content is king. If you can learn how to market that content, you’ll be ahead of the game.
The old adage is, indeed, true again: content is king. If you can learn how to market that content, you’ll be ahead of the game
Success can destroy
After an entrepreneur tells me how wildly successful they’ve been, I often ask, ‘Do you have $5 million in Treasury bills?’ Nine times out of ten, the answer is no.
The reason great entrepreneurs are not necessarily great investors is that they usually spend so much time focused on one thing that they ignore the concept of diversification.
Like everyone else, I once thought that I could beat the market and pick my own stocks. But it’s almost impossible to do that consistently.
What you think is your darling one day is your dog the next. That’s just how it is. And it seems like every generation must learn this for themselves – whether they are common investors or successful businessmen.
No one should ever put more than 20 percent of their holdings into any one sector and never put more than five percent into any one stock or bond in her portfolio.
After an entrepreneur tells me how wildly successful they’ve been, I often ask, ‘Do you have $5 million in Treasury bills?’ Nine times out of ten, the answer is no
Buy or rent
While I often advocate owning property, there is a caveat: you should only buy if you’re going to stay in that property for at least five years.
Otherwise, you’re better off renting.
Let’s say you’re young, you’ve just got your first job, you’re single and you can live close to where you work – that makes renting the obvious choice.
If you can walk to work, you’ll save a fortune on transportation costs. Then, take those savings and put the money towards the 15 percent of your income that you put toward retirement every year.
If you’re married and contemplating thinking about starting, that’s a better time to buy a home. Simply put, you’ll need more room than a rental can typically offer.
While this transition typically happens when people are in their late twenties and early thirties, the median age of first-time home buyers has slowly crept up over the years.
For nearly a decade, mortgage rates hovered between 3.8 percent and 4.5 percent. But today’s rates of six percent or more don’t mean that first-time buyers are left out in the cold entirely.
It does means that they’ll have to settle for a smaller starter home.