Jeff Bezos Gambled on a Garage Startup. It Paid Off Big, But No One Saw This Coming

Jeff Bezos’ risk-taking and long-term investment has been a driving force behind Amazon’s rise to global dominance. His vision helped the company not only survive the dot-com crash of the early 2000s but thrive in the years that followed.

It all Started in a Garage

Launched in 1994 as an online bookstore from his garage, Bezos’ startup has grown into the fourth most valuable company in the world. Today, Fortune estimates Amazon’s worth at $2.4 trillion — a testament to the power of patience, innovation, and staying the course.

Today, it drives how we shop, collect data, and stream, serving as the go-to destination for everything.

Bezos, who left Wall Street to sell books in Bellevue, Washington, with his then-wife MacKenzie Scott, followed a dream of dominating the internet.

With a motto like “Get Big Fast,” he started with books, a product that was easy to ship and had broad, universal appeal.

It wasn’t easy in the beginning. Operational costs were a major challenge, and Bezos had to cut corners wherever he could. 

To save on expenses, he held early Amazon team meetings at Barnes & Noble.

By 1996, as the internet was beginning to reshape how people consumed media, Amazon’s growing momentum caught the attention of Barnes & Noble founders, the Riggio brothers: Leonard S. and Stephen.

The irony of meeting inside their stores was not lost, and the bookstore giants saw Bezos’ startup as a rising threat.

Even after being warned that Barnes & Noble would eventually crush Amazon, Bezos stayed committed to his bold vision. 

His “Get Big Fast” mindset pushed him to look far beyond selling books.

By 1999, the goal was clear: expand Amazon into a platform where customers could buy just about anything — games, movies, music, and all the everyday essentials — delivered right to their doorstep.

The dot-com bubble burst between March 2000 and 2002. Many websites launched quickly, got a lot of attention, and then failed, according to Ava Trade.

Overhyped and oversaturated, sites like Pets.com and Webvan went under early. Only a few, like Amazon.com, survived and came out stronger.

Unlike many others, Bezos didn’t chase quick returns. 

He followed a motto he called the “regret minimization framework” — the idea that real rewards come from accepting early losses and taking risks the right way to achieve long-term goals with minimal regret.

The risk the company weathered through, being one of the first major companies online in the 1990s to offer fast shipping, low prices, and a wide selection, was an unfamiliar concept back then, but it quickly changed how people expected to shop forever.

Between the 2000s and 2010s, Amazon added Prime, Kindle, and Amazon Web Services (AWS), turning the company into more than just an online store. It became a streaming service, a hardware maker, and a major player in cloud computing.

As his company exceeds a $2 trillion valuation, putting it on par with Microsoft, Apple, Nvidia, and Alphabet, Bezos’ net worth is estimated at $209 billion, according to Forbes. 

That makes him the second-richest person in the world behind Tesla CEO Elon Musk — but the gap between them isn’t all that wide.

Barnes & Noble has experienced a massive decline over the years, despite its founders once believing that the company would easily surpass Amazon.

Valued at $800 million in 1999, Barnes & Noble is now worth only $300 to $330 million as of July 2025, according to Bloomberg.

The late Leonard Riggio, who stepped down as CEO in 2002 and retired from the board in 2017. He died in August 2024.

His brother, Stephen Riggio, who served as CEO from 2002 to 2010, has largely stayed out of the public eye, and his current net worth is not publicly disclosed.