But this week as Apple, the much-loved technology company, became history’s most valuable public corporation, I allowed myself a look back at what might have been.

Some 15 years ago, almost to the day, I ruefully recall, I was the owner of around 400 to 500 shares in Apple.

Today, with its market capitalisation of around $630 billion, if Apple were a sovereign nation it would be a G-20 member, the value of its gross domestic product slotting in around the world’s 19th to 20th biggest  — alongside Switzerland, Sweden and Saudi Arabia, almost three times the size of Singapore, 11 times bigger than Syria and Sri Lanka, near 50 times Senegal.

And I owned a modest chunk of it when the entire company was valued at just USD2 billion, when Seychelles and Sao Tome and Principe could’ve given it a run for its money.

If I’d hung onto my Apple shares — and I tend to philosophically subscribe to that old ‘if’ aphorism about aunts and uncles’ testicles — then with subsequent dividends, splits and re-investments, not to mention its virtual reincarnation from a near-death experience in 1997, I calculate the holding would be worth around USD2 million to USD3 million today.

I recall that Rupert Murdoch’s mate, the Saudi financier Prince Alwaleed bin Talal, also bought Apple shares about the same time as me, acquiring some five per cent of the company for about USD115 million in April 2012.

He was educated in Silicon Valley and he’s still got them, two more reasons why he’s a billionaire and I’m not. But he also owns a lot of Citibank shares, and they’ve been mercilessly hammered since the 2008 financial crisis. And I’ve never been so naive as to much believe bankers.

With the bounty from my Apple portfolio that I once had, I could today buy about 2,000 Mac Book Pros, 10,000 iPads, 150,000 iPod Shuffles and who knows how many tunes of iTunes. And I’d be writing from a luxurious condo at an Aman resort somewhere expensively exotic, surrounded by all things divine and perfect. That I owned.

Instead, as pissed Poms on a stag party puke their Grolschs and haring onto the pavement outside my window, I write it from an apartment in Amsterdam. Which I don’t own.

I REMEMBER making the Apple trade, less for the head-spinning wealth that would (not) follow but for the amount of money I risked at the time — USD10,000 from memory, then as now a ridiculous amount for someone who’s tended to think trading the stockmarket a mug’s game.

I made it sometime in mid-1997. I was then an Australian Financial Review staff correspondent in the US, based in San Francisco, with a brief to cover California, supposedly modern society’s laboratory. I was planning to write a story about online share trading.

Initially sent to Los Angeles, I quickly became aware that Corporate Hollywood wasn’t where the world was being re-invented. That seemed to be mostly happening a few hours up Route 101, just south of San Francisco in a place insider hipsters liked to call Nerdistan — a place the world knows as Silicon Valley.

Sick of the long drives from LA, I moved to San Fran to be closer to this rise and rise of the post-industrial ‘New Economy,’ where this amorphous thing called ‘The Internet’ was being defined. I was reporting on how it might affect the traditional pillars of the economy, particularly for — pace the bulk of the AFR’s readership — banking and finance.

The whole area was — and is even moreso today — as much a feeling, an ideal, as it was a sprawling conurbation either side of the Bayshore Freeway from San Francisco to San Jose.

I lost count of the times I drove up and down the 101 during these years seeking stories and interviews with people few beyond the Bay Area had ever heard of. Many of those interviewed are now billionaires: people like Eric Schmidt, today Google’s boss, then an executive at Sun Microsystems. And John Doerr of venture capitalist Kleiner Perkins Caulfield and Byers, which seeded Google, Amazon and Netscape among many others. And Intel’s Gordon Moore, he of the legendary Moore’s Law.

They lived and worked in places like Redwood City (home of Oracle), Menlo Park (Sand Hill Rd, Nerdistan’s Wall St, and today Facebook), Palo ‘Shallow’ Alto (Stanford University), Mountain View (where Steve Jobs lived), Sunnyvale (Google and Yahoo), Santa Clara (Intel), San Jose (Cisco, eBay et al) and Cupertino (Apple).

Mostly low-rise suburbs, Nerdistan was all so remarkably unremarkable. But no less aspirational. Once, tapping out an email while my room service breakfast was being unpacked at the Fairmont in San Jose, the Vietnamese-American waiter asked me if my Compaq (remember them?) laptop “was powered by Pentium?” It occurred that only a few hours south down the 101 in LA, hospitality staff ‘wait’ to be discovered by Hollywood moguls. In Nerdistan’s dream factory, they’re waiting to be Steve Jobs.

I’d noticed emerging phenomena such as ‘online trading’ and ‘online banking’ taking off and figured it would be good to road-test them for a story about how technology was transforming the financial sector.

Soon after arriving in the US in late 1996, I signed on for an account with America Online, then the world’s biggest internet provider. On near perma-clogged 14kbps telephone lines, I later managed to open accounts with Bank of America and start-up broking companies called eTrade and Ameritrade.

That I should buy Apple for the online trading story was unsurprising. It was the gripping story of the day, the company famously founded in Jobs’s garage, the company which had made modern gadgetry cool, even sexy, with its design ethos.

But it had fallen on tough times. It was losing billions, and Microsoft, the interloper from Seattle portrayed as the evil empire in the Jobs-obsessed Silicon Valley, had easily eclipsed it in the software market, and the booming internet economy was passing it by. Though posters of Jobs adorned the bedroom walls of many Nerdistan geeks, he had been long ousted as Apple boss.

Nerdistan facsimiles were springing up around the Microsoft campus at Redmond in the US Pacific Northwest, along Boston’s Route 128, in Colorado, Utah, Texas and Virginia, indeed around any American educational and military heartland. Many experts and techno-hacks portended the demise of this landmark company of American innovation. Momentum seemed to be slipping away from Silicon Valley.

But rumours began to build through June 1997 that Jobs was coming back, in search of The Next Big Thing for Apple. In July he was welcomed as an Apple ‘advisor’ and on August 6, 1997, he appeared, to jeers from Apple cultists, on stage at the Macworld Expo in Boston with Bill Gates, who announced a USD150 million investment by Microsoft to ‘save’ Apple. In my report of the deal, I quoted an analyst who likened the Gates-Jobs show as “like putting Darth Vader up at a Star Wars convention”. The rest — the funky iMacs, Jobs’s myriad other must-haves, and his death last year — is history, USD630 billion worth.

I remember my Apple transaction not for the missing millions, mostly, but for the principled outrage it generated for me.

I recall intending only to buy a modest 100 shares, about the smallest parcel one could buy. But with a slip of the finger on a keyboard on a ropey 14kbps dial-up connection, I managed to buy 400 to 500 instead. The deal cost about USD10,000 from memory, executed moreover at a price way higher than I believed I was buying.

I complained to the customer service automaton that it was all his company’s crappy software’s fault. The response was ‘caveat emptor‘, saying there was a long delay between my trade and their executing the order, and they can’t be held responsible and, and, and…

Some 15 years on and without any supporting paperwork to hand, my abiding memory is being worried for a few months about having USD10,000 at risk as Apple wobbled.

But the fact is, had I hung onto those shares, I wouldn’t be writing about it at all today. I’d be luxuriating in my good fortune, which I wouldn’t be calling good fortune but perspicacious investing during 10 of the worst years to be an investor in stocks. Except I wouldn’t be doing that either, because shares only become cash when they’re sold. And, in an ideal world, I wouldn’t have sold them.

Truth be told, if I was still an Apple shareholder, I’d likely be a nervous obsessive and even more boring than my wife says I am when I’m reminded, as I was again this week, about my Apple-fortune-that-got-away. My Apple shares would probably be the only thing I’d talk about. I’d be equipped with every known device to monitor the share price and sell as the price — and my nerve — faltered.

As it did. Some 15 years after being, for a few months, an Apple shareholder, the reason I no longer have any — to the best of my knowledge — is because I was always nervous owning them, about owning any shares for that matter. Journalism is professional scepticism and I’ve reported too many company collapses, scandals and corruption to believe trading stocks makes one rich. And, of course, one should only invest what one can afford to lose.

Conflict of interest has also been a concern. I also remember the general relief after selling them later the same year, to help pay for a week’s skiing at Lake Tahoe with my then soon-to-be wife, even though I took a 20 per cent loss doing so.

And I never wrote the story about online trading, because AFR readers aren’t supposed to be nervous shareowners. Isn’t that who read the AFR? Nerveless Masters of the Universe?

Still, as a bill-paying wage slave, I hold out some hope that I might yet be one of Apple ‘millionaires-next-door,’ everyday people like Rich and Mary Bleyle of Buffalo, New York, who also bought their Apple stock in 1997 and, USD2 million later, still have them. Or the soldier who began accumulating Apple at USD33 in 2005 for his retirement fund and now has USD6 million worth.

My fortune-that-never-was recollections above are from memory. I’ve moved five countries and six houses since 1997, and my records are patchy at best. When I saw Apple become the world’s most valuable public company this week, I went on a slightly manic search for my account statements of the day, to see how many I did once have.

And maybe, just maybe, if I still had some, hoping that my memory isn’t as good as I think it is. At the very least, I finally got around to writing my story about online trading, which is better than being boring about Steve Jobs.

Do I regret selling? Not really — I had a memorable Thanksgiving ski with the woman who became my wife.

And as Cranky Franky also once put it, “flying high in April, shot down in May”. That’s life, 15 years on.

Read more Eric Ellis reports on France’s rightward turn, another great wave of Irish immigration to Australia, and an ailing Spanish town that caught — and kept — the post-Gaddafi blues.