Some people see things as they are and ask why, Founders dream of things that never were and ask why not?

At 64 and four years into my 'very last' startup venture, it was suggested by an audience member at SXSW Sydney, where I was speaking this year, that I write about some of my journey and experiences during my life as a serial entrepreneur.

This will be the first of a ten part series.

Entrepreneurship requires a guiding light, and for me, George Bernard Shaw’s famous words have always been a beacon:

“Some men see things as they are and ask why. I dream of things that never were and ask why not.”

This quote captures the essence of entrepreneurship—looking beyond what exists to imagine what could be.

It’s what keeps you pushing when the odds are against you, and it’s why you keep coming back to the drawing board after every setback.

In founding a company, I’ve found the word “founder” to be a double-edged sword. As a noun, it’s glamorous—“Bill Gates, Founder of Microsoft.”

But as a verb, it’s disastrous—“the ship was seen to founder.”

Founding a startup, as I’ve learned through over 20 ventures and 50 years, is about riding that fine line between triumph and disaster.

Sometimes the two feel indistinguishably close, as many of today’s unicorn founders would tell you. Take Elon Musk, for instance. When he faced financial ruin in 2008, he made the bold choice to pour his last dollars into Tesla and SpaceX.

Musk’s mindset resonates deeply with every entrepreneur who has faced that make-or-break moment: betting on yourself, your team, and your vision, even when the odds seem impossible.

An entrepreneur is born that way. You can’t teach it in a university—no amount of Harvard case studies or neatly typed-up MBA notes will prepare you for the strange, exhilarating, and sometimes absurd journey of starting and running a business.

Trust me, no professor ever warns you about dealing with a supplier who “only works Thursdays” or a client who insists their payment is “in the mail” for months on end. In the U.S., they’d call it “giving it a shot”; here in Australia, we call it “giving it a crack.” But wherever you’re from, once you’re on the ride, it’s far more than just a title.

No textbook ever taught me how to come up with Monday’s payroll when, by Friday, the bank balance was looking grim. But somehow, every weekend, a true entrepreneur finds a way.

When others might panic, an entrepreneur digs deep, taps every resource, and scrapes together what’s needed to pay the team.

Brian Chesky of Airbnb knows this feeling well. In the early days, he and his co-founders maxed out credit cards and sold novelty cereal just to keep Airbnb alive. Like Chesky, I learned that when things look bleak, you double down, hustle, and innovate your way through.

I learned my lessons early.

In 1974, at 14, I borrowed $35 from my parents to buy a surfboard, seeing an opportunity in the seasonal cycle of Melbourne summers and winters.

Melbourne is, of course, only 100 km east of Bells Beach, which every Easter runs the world’s most prestigious surfing competition.

In the heat of each summer, teenagers would rush to buy surfboards; six months later, with the Southern Ocean winds howling, the same boards would collect dust.

I bought, cleaned up, and flipped boards for three seasons, reinvesting every profit, until, by Christmas Eve 1977, I’d sold all but one of the 115 boards stored in my parents’ backyard from that year.

Sixteen years later, in 1993, proudly one of my hotel businesses would go on to sponsor the world’s most prestigious surfing event, the ‘Sugar Shack’ Bells Beach Classic, a full-circle moment that crystallized my “why.”

Now, Simon Sinek might tell you to “Start with Why,” and I wholeheartedly agree. Your “Why” is your anchor, your North Star, your purpose when things get murky (and believe me, they will).

But Sinek doesn’t mention the all-nighters fuelled by bad coffee or the times when your “Why” seems to have wandered off, leaving you staring at endless spreadsheets wondering if you’re completely nuts or about to become a "Was".

Just like Jeff Bezos, who early on was obsessed with perfecting every part of the customer experience—even observing Amazon’s warehouse packers to understand where delays occurred—founders have to stay deeply connected to every detail and endure long hours to bring their visions to life.

Beyond the “Why,” though, entrepreneurship requires a mindset of seizing moments—what I call the “Sliding Doors” doctrine.

Life is full of those moments, split-second decisions that can change the course of your business or even your life. Whether it's taking on a risky new market, deciding to partner with a long-shot investor, or seizing an opportunity you almost overlooked, these doors open and close in an instant. Jack Ma, the founder of Alibaba, faced countless “sliding doors” moments. After being turned down for dozens of jobs, he kept pushing forward, certain that his “why” would open the right doors.

Knowing when to step through is a skill in itself and one I’ve come to value just as much as the “Why.”

What this series will offer isn’t another pep talk or a textbook. Think of it as a collection of true tales from the entrepreneurial battlefield.

Each story captures moments of grit, comedy, disaster, and triumph. Whether it’s navigating a disastrous product launch, landing that make-or-break deal, or figuring out how to tell your family that, yes, you’re starting another venture, this series will give you the real picture—with a laugh (or ten) along the way.

Because in the end, being a founder is about staying nimble, trusting your gut, and never letting the ship—or the vision—truly founder.

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