People often ask me what I would do if I had to start from zero, with nothing in my pocket, and rebuild my fortune from scratch.
My answer hasn’t changed over the years: I’d still be an entrepreneur.
And it’s not because it’s the easiest route to wealth – far from it.
In fact, entrepreneurship is one of the riskiest ways to make a living.
Most people opt for the safer path: a steady nine-to-five job, investing consistently, and hoping to retire with a comfortable nest egg.
That approach works for many, but it takes time, patience, and discipline.
Entrepreneurs, on the other hand, thrive on risk.
I like knowing that my success is in my own hands. If you can spot a market need and meet it, the rewards can come faster than almost anywhere else.
Skate to Where the Money Is Going
One of the best pieces of advice I’ve ever received comes from Walter Gretzky, Wayne’s father: skate to where the puck is going, not where it is. In business, this couldn’t be more relevant.
If I were starting out today, I’d focus on where the money is flowing. Take AI, for example.
Meta plans to spend $600 billion on AI infrastructure over the next three years and just committed $1 billion to a new data center in Wisconsin.
Microsoft has already invested nearly $35 billion this year on AI centers.
Every sector in the U.S. is using AI to cut costs and improve margins, but it all relies on land, energy, and infrastructure.
That’s where I’m placing my bets for the next two decades: the foundations that power AI.
Learning to Fail Without Losing Confidence
Here’s a tough truth: about 80 percent of start-ups fail. That hasn’t changed since the 1950s.
And yet, young entrepreneurs often charge ahead with single-minded determination, convinced their idea will succeed against all odds.
Persistence is good, but stubbornness can be costly.
You need the ability to step back, listen to the market, and know when it’s time to pivot or walk away.
Often, success comes on the second, third, or fourth attempt.
Failure isn’t a roadblock – it’s a teacher. The sooner you learn that, the sooner you can move toward something that actually works.
Education Is Evolving
I’ve also changed my perspective on education.
I used to say that engineering degrees were the only ones worth pursuing, but that’s no longer true.
Creative storytelling and social media skills are now among the highest-paying talents in the market.
Companies are willing to pay top dollar for people who can craft content that converts audiences into customers.
Many of these social media experts work for multiple companies at once, often earning four times what a typical employee would.
Content truly is king, and the ability to market it effectively can give you a huge advantage.
Success Can Be a Double-Edged Sword
One lesson I keep repeating to successful entrepreneurs is this: don’t ignore diversification.
I often ask, “Do you have $5 million in Treasury bills?” Nine times out of ten, the answer is no.
Even brilliant business minds can struggle with investing because they get consumed by one big idea and neglect broader financial strategy.
No more than 20 percent of your holdings should go into a single sector, and never more than five percent into one stock or bond.
It’s a lesson every generation must learn the hard way.
Buy, Rent, and Timing Matters
When it comes to real estate, buying isn’t always the right move.
If you’re young, single, and just starting out, renting near your work is often smarter.
You’ll save on commuting costs and can direct more money toward retirement savings.
Buying a home makes sense later – typically in your late twenties or early thirties – when you need more space.
Higher mortgage rates today mean first-time buyers may need to start smaller, but it’s still possible to get a foot on the property ladder.
Timing and planning are everything.
The Bottom Line
Starting over is never easy. But entrepreneurship offers a path where your effort directly shapes your results.
Stay alert to where opportunities are heading, embrace failure as a lesson, invest wisely, and make thoughtful choices with property.
Do all that, and even starting from scratch, you can build something extraordinary.
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