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Part 4: A larger mission

What allowed Bezos to see those opportunities? “He’s just a brilliant businessman. There’s no two ways about it. I think from having come from the big money world of Wall Street, and also the big ego world of Wall Street, just to be able to see a huge opportunity and go after it was part of his frame of reference.”

GeekWire Interview: Shel Kaphan,’s first employee

Why did you leave in 1999? “Two and a half years into the company, they hired two other tech managers, and basically my job was divvied up between the two of them. I was transitioned to being CTO, and still in charge of architecture. But right away, the projects that the new managers were doing were having significant architectural effects that I was not involved in overseeing, or being able to say no to anything or being able to instigate anything. I basically felt that I had been sidelined. There are other things that I probably don’t want to talk about. There was a lot that I still wanted to do, and I kind of felt like the position I was in after the new managers were hired, was not one where I could do the things that I wanted to do there anymore.”

Was it a good experience for you? “The first half (of my tenure) was probably the most fun I’ve ever had anywhere, building something from scratch up until about the time the company went public…. One of the things that attracted me in the first place about Amazon is that I could easily describe how we were going to make money, to anybody. We are going to sell books. People will send us money, and we will put it in the bank. And then we will ship them a book. And we will do that a lot…. It was so fun to be in a situation where people were using it, and liking it and telling us what they liked and didn’t like…. For me, having been in the back room as much as I had been in my career with most of the development work I’d done — just having that direct feedback from customers and being able to change things and have that effect what was happening in the business right away, and often in a significant way, was just amazing. It was so fun.”

The second half of your tenure wasn’t as fun? “The company started growing and we started attracting zillions of MBAs. (We’d) have meetings all day long about what was going to be happening over the next six months, and the fact that my responsibilities had changed, it just stopped being fun. So, after five years were up — and my stock was all vested — I probably would have left a little earlier if that had not been the issue. But I thought it was a good business decision to stick around, so I did. One of the things that happened to me in the first two and half years was that I was more hacking than managing, which being that I was in the position that I was in was perhaps not the smartest thing in the world. But I was in the middle of all the technical stuff that was going on, and technical operations as well. So, if there was any kind of hiccup, in the early days I would log in using a modem over the phone several times during the night, and if things were not working, I’d put my clothes on and drive down to Sodo and go fix the computers. I’d do whatever had to be done.

It was a very direct hands-on experience for me. Most of my personal background had been as a direct contributor. …I wasn’t an experienced large group manager, and so I was getting behind the curve on recruiting and some of those types of things, and once that happens in a situation where your company is growing quickly, that’s a bad place to be. I had so much that I needed to have my fingers in on a day-to-day basis that I couldn’t free myself from it easily to do the recruiting stuff, even if that had been something that I was good at or excited about, which I wasn’t. They did need more help to do that. And that is a lot of what the new guys they brought in were going to do, and they did.”

How much ownership did you have of “I think I’d rather not discuss that. We were not even partners. I was given a small fraction of what Jeff allocated to himself. … He did the fundraising initially, and some of those funds were his own funds and the rest were his family’s funds.”

But it is safe to say that this job made you a very wealthy person? “Yeah, it is safe to say.”

So, did you hang on to all of the shares because Amazon hit a rough patch just after you left? “I don’t know what the effect on morale inside the company was since I wasn’t there. But I did do a lot of selling during those times, because from the outside, without knowing what was going on inside the company anymore, I didn’t know if it was going to be a casualty of that era or not, so I cashed out quite a bit of my position. But I did hold on to some of it, and I continue to.”

Do you go to the Amazon shareholder’s meeting ever? “I have a couple times, but it tends to make me grumpy so I don’t like to go.”

Why is that? “It is just a style thing, I guess. I was never really a corporate type of person. And corporate events, even like all-hands meetings and that kind of stuff, always really rubbed me the wrong way. And shareholder meetings are kind of that on a grand scale. It is just a lot of show biz, basically. There is not enough content to make it worth the trouble.”

Does it surprise you how the company has transformed itself? “Some things have really surprised me.”

Meeting up with Shel Kaphan in a bookstore.

Like what? “The fact that they are selling hardware of their own, that surprises me. The fact of the whole cloud business, surprises me. In my time there, I guess I viewed it being really a challenge for us just to do what we were doing. For them to have gotten on top of so many other areas — and done well in them — it shows a lot of growth that had not happened or had not even really shown signs of happening during the time I was there.”

What have you been doing since leaving Amazon? “I have my longtime partner/girlfriend, Ericka, and she lives with me… I really don’t understand how I had time to work as much as I did. I had a 25-year long career of working 60- to 80-hour weeks, and that’s enough. I stopped working at a fairly young age … but I was pretty fried by the time I stopped. I needed a lot of time to regroup.”

What do you do for fun? “I have a little foundation that I do a few things through. And I am an advisor to the Grameen tech center downtown. Outside of that, not really that much. I am a keep-to-myself kind of person. But, you know, a lot of the last decade has been regrouping after spending quite a lot of my life sitting in front of a computer writing code. It was fine for me, but it may not have been the true love of my life to do that. I still like writing programs occasionally, but I don’t need to do it all day, every day anymore. I’ve been there, and done that.”

I can’t help but notice that you have a book here and it is checked out from the Seattle Public Library: “I would say 90 plus percent of my reading comes from the public library. Because a) they have a terrific online presence and b) they have a branch blocks from my house and, most importantly, c) they demand their books back, which causes me to finish getting them read. When I buy books, they sit in a pile. And when I check them out from the library, I get them read or decide not to read them. In any case, they go away.”

Do you own a Kindle? “I do.”

I must say when I came here, I thought you’d be easy to spot because you’d be sitting here with a Kindle. It is ironic that you are not only sitting here with a hardcover book, but one from the public library: “I appreciate the irony value of it, probably part of the reason that I do it.”

Do you like the Kindle? “I like it for traveling and for the ability to search. I like the ability to write notes in books that then can be invisible, even though writing notes is still awkward on the (device). I am kind of agnostic about them. All things being equal, I still prefer paper books. It is easier to flip through them. Technical stuff and graphics on the Kindle, it blows. Anything that has any mathematical typesetting, forget it, it is just unreadable.”

Do you use Amazon for anything else? “Yeah, it is a great resource. I am probably not one of their bigger customers, but I fairly regularly get stuff from them. And stuff that the library doesn’t have and can’t get that I really need to read, or if there are 100 people in front of me that are going to read the three copies that they’ve got, then sometimes I will break down and buy it.”

Do you ever talk to Jeff Bezos? “We are not in touch.”

Is there any bad blood there or was there a falling out? “Well, there are still some issues about my transition out of the original position that I had that I didn’t feel were handled in the right way. But that’s as much as I will say about that.”

What would you ask Bezos if you sat down with coffee for him today? “The first (questions) that come to mind are personal, but one that I’d like to ask him is whether, even after what’s happened in the economy since 2008, if he would still contend that less government regulation is always better.”

What is your favorite memory of your time at Amazon? “I think I remember more of a vibe, than an event. Being there, like, for example, late on a Friday night and sharing my office with one of the other programmers, Ellen (Ratajak), and we’d just have on some rockabilly (music) really loud or something crazy like that and just hacking away. And just getting stuff done, and being able to put it into the world.”

The way you describe working at in those early days is how so many startups operate. It doesn’t sound that different: “No, I wouldn’t think, other than they have better tools now.” (Laughs)

You mentioned that you like to spend time with a math professor friend tinkering with new mathematical methods and ideas, just for fun. Really? “People who don’t do that for fun don’t understand why it could be fun. It is actually one of the more beautiful areas of reality for people that have the tool box to be able to appreciate it.”

It really is a hobby. You aren’t trying to build something new? “It is not involved in anything commercial. There’s a paper I am trying to write, but that’s kind of going slow.”

Would have any aspirations in going to work for another company? “Every once in a while I think of some software that I’d like to build or see built, and usually the horror of startup existence dissuades me. And, also, given what’s going on on the Web these days in particular, if you think that you are on to something that nobody else has thought of, you’re probably deluding yourself. Usually by the time I’ve thought of something and I sniff around a little bit, there are already 10 different companies that are well on the way to doing the same thing, or better. I have some ideas. Even now, I am thinking about doing some stuff, but nothing active. My orientation, as I said earlier, is that I’ve never really been a corporate person. I had a strong desire to build something that was going to work, and the original mission the way that it was in my mind was a continuation of the Whole Earth Catalog mission. The updated version of (that mission) would be to make every book in print available to everybody, everywhere in the world, even if you are in Siberia or something. That part of it I am really proud of and happy that we succeeded. But, as far as shipping lawn furniture to people in Iowa, I really don’t care about that. I am glad that the company is successful doing that, but it is not something that is important to me personally. And that type of success is not important to me personally. I am glad that I was able to get out of the rat race, and have my time to myself more. But, beyond that, I really don’t have corporate aspirations.”

We’re sitting here outside a bookstore. So, for you, in those early days really was about a bigger mission related to books? “For me, it was. Or, at least, if not books, tools in the generic sense.”

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