In hindsight incredible success often looks inevitable. Take Amazon, for example. The founder is clearly a super smart guy with a track record of success and the concept for the business was both a clear winner and well timed. Of course, launching an online bookstore in 1994 would be a success, you might think.

But while success can appear straightforward in the rearview mirror, in reality it's nearly always a twisting path full of uncertainty and setbacks. It's helpful to remember that no one rockets along with perfect confidence and a foolproof strategy -- not even Jeff Bezos.

Don't believe me? Then check out the highly entertaining and in-depth interview with Shel Kaphan, employee number one at Amazon, that appeared recently on Y Combinator's blog The Macro.

Everything seems like an uncertain bet at the beginning.

Kaphan kicks of the interview by telling the story of how he ended up somewhat reluctantly relocating from Santa Cruz to Seattle in 1994 to start an online bookstore with a guy named Jeff Bezos. "At first I was a little bit tentative about it-I kept my house in Santa Cruz and I only moved the minimum amount of stuff I needed to live," Kaphan relates.

"I thought, 'Okay, I'm going to be building this website to run a bookstore and I haven't done that before but it doesn't sound so hard. When I'm done with that I'm not sure what I'll do.' At that point there was no idea of doing anything but a bookstore. I thought maybe I would be able to go back to Santa Cruz and monitor it from there. I was pretty wrong about how the business would develop and how ambitious Jeff was," he continues.

The interview digs into the technical details of the first iteration of Amazon for those who are interested, but it also goes on to reveal plenty of funny and telling details about the company's early days, including lots of missteps and tons of hard work.

For instance, when the interviewer asks Kaphan, "How did you troubleshoot? Today I use Stack Overflow constantly. What would you do when you ran into a bug that you couldn't figure out?" Kaphan responds simply: "Stay up late," eliciting laughter. Other interesting topics discussed include:

  • How Bezos refused to invest in hardware rather than customer-facing features early on, leading to several issues.
  • Bezos' apparently hands-off approach in the early days. "We never even had a written business plan that I know of," recalls Kaphan.
  • The lucky personal connection that helped introduce Amazon to the world.
  • How startups have changed in the popular imagination. "Those days were still before everything that's happened with glorifying startups. If you were going to do a startup business, there wasn't a huge expectation that it was going to be glamorous," says Kaplan.
  • How any sort of commercial endeavor on the internet was still controversial when Amazon got started.
  • Kaphan's concerns with the direction tech has since taken.
  • The eventual falling out between Kaphan and Bezos, and the lessons Kaphan took from his years at Amazon: "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."

Check it out in full for an interesting glimpse of the early days of one of tech's most iconic companies.

Published on: Sep 15, 2016