I was at Amzn in 2000 when the internet bubble popped. Capital markets dried up & we were burning $1B/yr. Our biggest expense was datacenter -> expensive Sun servers. We spent a year ripping out Sun & replacing with HP/Linux, which formed the foundation for AWS. The backstory:

My first week at Amzn in '99 I saw McNealy in the elevator on his way to Bezos' office. Sun Microsystems was one of the most valuable companies in the world at that time (peak market cap >$300B). In those days, buying Sun was like buying IBM: "nobody ever got fired for it"

Our motto was "get big fast." Site stability was critical - every second of downtime was lost sales - so we spent big $$ to keep the site up. Sun servers were the most reliable so all internet co's used them back then, even though Sun's proprietary stack was expensive & sticky.

In 2000, brand new Sun servers started appearing on eBay for 10 cents on the dollar as VC-backed start-ups went out of business (this was pre-AWS when you had to roll your own datacenter). Amzn could have negotiated a better deal with Sun, but Jeff chose a more radical approach.

Amazon's CTO was Rick Dalzell - ex-Walmart, hard-charging operator. He pivoted the entire eng org to replace Sun with HP/Linux. Linux kernel was released in '94, same year Jeff started Amzn. 6 years later we were betting the company on it, a novel and risky approach at the time.

For @Codecademy's first 4yrs, we were in the 📰 every wk. Those weeks, we made $0. The past 4 years, we've been out of the headlines. Now, we've raised $40m, our first raise in ~4yrs.

How'd we go from the center of the hype cycle to the brink of bankruptcy and back? Read on...

We started @Codecademy in 2011. With software eating the world and few ways to learn to create it, we saw a huge opportunity. In YC, we built Codecademy as "the easiest way to learn to code." We posted it to HN as a Hail Mary before Demo Day and got 200,000 signups in 3 days.

We were off: the press loved it, we were on every 30 Under 30 list, won awards, and more. As a founder, all of this felt great...until we had to raise 💵 to stay alive. All the press clippings didn't add up to enough $ to demonstrate we'd built something people would pay for.

With a few months of cash left in 2015, we scrambled to build Codecademy Pro, our first paid product, with new courses and new features for learners.

Going from the center of attention to the brink of bankruptcy was a rude awakening.

We struggled, but hit $1m ARR in ~6 months to raise a successful Series C to keep the company alive.

On the way, we learned an important lesson: hype doesn't pay the bills.