There weren't too many investors arguing that (NASDAQ:AMZN) was a bargain in 1997, but that didn't stop Motley Fool co-founder David Gardner from buying into the fast-growing online retailer for the original real-money Rule Breaker portfolio.

Amazon was losing money, and a market cap approaching $1 billion seemed misplaced for a company founded on the premise of offering books online, even if the e-tailer's Seattle warehouse was brimming with an unmatched 2.5 million different titles. Buying roughly $11,000 worth of the stock at a price of $38.22 seemed risky, but the shares were starting to move. Amazon went on to push out three stock splits -- 2-for-1, 3-for-1, and 2-for-1 -- over the next 24 months, pushing down David's cost basis to $3.185 a share. When the stock wrapped up last week with a new closing high of $328.93, it became a 100-bagger.

Semitrailer with Amazon Prime logo on the side

Image source: Amazon.

Bigfoot and the Loch Ness Monster may not be real, but the 100-bagger beast is apparently legit.

Portfolio-altering investments aren't always obvious right away
This isn't about bragging. 

David went on to sell partial stakes in Amazon as it raced higher during the sudsier days of the dot-com bubble. The Rule Breaker port went on to raise $46,394 by cashing out of chunks of that blazing-hot investment. In other words, it's not as if we can say that this $11,000 purchase in 1997 would've been a millionaire by now. David decided not to be greedy by working some allocation magic to buy into new growth stocks.

Nobody's perfect, and David learned a lot through those trades.

I was fortunate enough to have been invited to the birth of Amazon's entry into the portfolio. I've been with the Fool since 1995, and I would occasionally pitch in with the daily portfolio recaps. It was a lot of fun to see Amazon double and double again, but I had my doubts. Where was the profit? Where were the positive gross margins? As it would go on to expand from books to music in 1998 -- and video shortly after that -- was Amazon spreading itself too thin as the online king of all media? 

I was asking all of the wrong questions. 

David was willing to look beyond the worrywart concerns, making a wager on what Amazon would become rather than what it was at the time. Wall Street burns so many investors and speculators who miss out on that important lesson. They spend too much time reflecting on the rearview mirror, missing out on the bargain of their lifetime disguised as an overvalued growth stock.   

To be fair, even Amazon CEO Jeff Bezos didn't see it coming -- and this guy oozes visionary mojo. 

"Maybe one of the things that we can do is when you come in and if you search for books on kayaks, we'll show you the list of 225 books we have on kayaks, but we'll also show you an advertisement for a company that sells kayaks," he told Upside magazine shortly before our purchase, explaining how the virtual bookstore could have a future in online advertising. "And you can click on that and go to their website and buy a kayak."

Well, Amazon has 1,123 books on kayaking now, but -- more important -- it's also offering up 1,355 kayaks!

Holding out for the next 100-bagger
Will David nail another 100-bagger? Why not? Naturally, you can't judge these events with egg timers. It took Amazon 16 years to play out that way here. His next blowout investment may take even longer to flesh itself out.

It also won't go up in a straight line. Does anyone remember what happened to Amazon after the dot-com bubble popped? The stock shed nearly 80% of its value in 2000 alone.

However, as surely as you'll find David warming up to a stock that too many investors hate -- bypassing the upstart because they're too stuck on the past to visualize the disruptive path of its future -- there will be more 100-baggers to celebrate.

Oh, and when Amazon doubles again, keep in mind that we'll be toasting this as David's 200-bagger. Getting in early has its compounding advantages. Staying in late -- something that David didn't get entirely right in the Rule Breaker portfolio -- can sometimes be even better.