Shel Kaphan was the very first employee hired by Amazon CEO Jeff Bezos, in 1994.
He was responsible for building the technical infrastructure in the early years of Amazon and played a critical role in growing the e-commerce site into a multibillion-dollar business.
But despite his early contributions, Kaphan didn't last long at Amazon.
He left just five years later, after Bezos hired two new technical managers and significantly reduced Kaphan's role at the company. Bezos and Kaphan are believed to no longer be in touch.
In an interview with The Macro's Craig Cannon last week, Kaphan reflected on his experience at Amazon and offered one big piece of advice that any startup employee could benefit from: Always think the company could get bigger than you ever imagined, and prepare for the changes by figuring out how you would fit in to the new environment.
"One thing that the Amazon experience taught me is try to imagine what a project or company would be like if it was more successful than you could ever possibly imagine. It's very unlikely but it's possible. You have to think about what the environment will be like if that happens, and how the people involved in it might change.
"When I was joining Jeff to form Amazon in the beginning, I didn't even allow myself to go there. I'd worked for a lot of startups so it almost felt like a jinx to think too much about what might happen if it really succeeded in a big way. That was my mentality. I was like, I hope this makes it and is a moderate success. Maybe it even generates enough cash to let us retire at some point.
"You don't really want to think about massive success beyond what you can imagine. Then, if it is successful, you have to start thinking, what's my role in enabling this? Is that something I really want to be doing?"
As Brad Stone wrote in his book " The Everything Store," Kaphan was devastated when Bezos removed him from the day-to-day operations of the company. Despite giving Kaphan the CTO title and later calling him "the most important person ever in the history of Amazon.com," Bezos essentially took him off the front lines, causing him to walk out on his own.
Kaphan described Bezos' decision as "a betrayal of a sacred trust" and "one of the biggest disappointments of my entire life," according to Stone.
Still, Kaphan seems to have fond memories of his time at Amazon. He told The Macro that the first couple of years at Amazon were a "high point" in his career and a "great time in my life."
And perhaps if he had thought more deeply about the changes taking place at the company, he could have done things differently, too.