The Inspiring Story Of The Man Behind SmugMug And FatBrain – with Chris MacAskill

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About Chris MacAskill

Chris MacAskill is the co-founder of SmugMug, the premium photo sharing site. Previously, he co-founded Fatbrain,  the online bookseller which sold to Barnes & Noble, worked for Steve Jobs at NeXT, produced an award-winning PBS documentary on Geophysics, and traveled the world for 10 years doing Geophysics until his family said, “Stop traveling!”

If you appreciate this interview you can thank Chris on Twitter, like this.

Raw transcript


This is a raw, mechanical transcript.

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Andrew: Hey everyone its Andrew Warner founder of mixergy.com home of the ambitious upstart. How many guys remember fatbrain? how many guys are members or have seen pictures on smugmug? I’ve got the founder of- the co-founder of smugmug, the founder of fatbrain, and mightywords and this guys had a very interesting career. I’ve got with me Chris MacAskill. Chris, I’m going to ask you this right up front. How much revenue do you have at smugmug?

interviewee: Well we used to give that number out and then 2007 i think “business week” quoted us as having 12 million, and its grown since then obviously. We don’t give it out anymore because we have been engaged in some lawsuits and our attorneys told us to shut up.

Andrew: lets see here.. what is smugmug for people that don’t know it?

interviewee: So its online photo sharing and it also includes video now all the way up to 1080p. the difference between smugmug and a lot of the other sites is that your photos look really great. Its designed around making your photos look spectacular and you can customize it like you customize a blog. Its a little bit like flickr but flickrs’ built around social networking and we’re built around good looks.

Andrew: And how much funding did you get to launch this business?

interviewee: Zero, zip, nada. no one would fund it for a lot of good reasons. One is it was 2002 and the venture capitalists thought the internet was kind of over back then. And secondly we had to go against blue chip brands, you know that were: Kodak, and Sony, and Yahoo and all those people. they were saying “well these are your priceless photos, the second thing you’ll rescue from your burning home when it catches fire. your going to trust them to a blue chip brand, and besides those blue chip brands are absolutely free. so what part of this internet business don’t you understand? Go away”

Andrew: What part didn’t you agree with?

interviewee: Well

Andrew: What was the opportunity?

interviewee: We thought that there was a premium brand in every market space. So, when you think about cars you probably think about Toyota, GM, and ford, but BMW does really well as a premium brand. I mean everyone thought for a long time- I used to work for Steve Jobbs- and everybody thought for a long time that Apple was dead, because they had such small market share and so on. But there is always a place for a premium brand, if you do well. So we thought we could charge some nominal fee for an annual subscription, which would get you free of adds, and give you unlimited storage, And a lot of things, big photo displays and so on, Being able to get your originals back and so on. That the free sites didn’t give and it worked because its a huge market, and if only a small percentage are willing to pay, its still a huge number of people.

Andrew: Can you say how much money you invested in the business to launch it?

interviewee: So i put in an initial $200,000 in the fall of 2002 and then about 2 years later we were sort of anxious to hire faster than we were hiring. We hired a couple of guys that made me put in another $300,000. So I went into it a total of $500,000 of my own money, but then after that it started making positive [unintelligible] which it does when you’re your own entrepreneur and you have to sweat and you have little sticky pads on the fridge that tell you how much money you have in the bank.

Andrew: did you really have sticky pads on your fridge saying how much money you had in the bank?

interviewee: I had sticky pads on my desk. i guess i don’t remember having them on the fridge i shouldn’t of said fridge. But i had little notes scribbled all over the place.. i mean our mantra has always been that “profit is accounting opinion but cash is fact.” So we would always check the bank very carefully and- my wife doesn’t like me saying this- but she is the countess of cash by the way, its a family company. She wouldn’t like me saying this but I always said “cash is more important than your mother.” when we started the company.

Andrew: How close did you guys get to not having any?

interviewee: Well probably $50,000 in the bank.

Andrew: Wow!

interviewee: That was probably the lowest.

Andrew: So 10% of what you put in total?

interviewee: Yeah, but we- but i was ready to put in more if i needed to. But the key thing is we didn’t think we could take any risk with anybody’s photos, because they are their priceless photos and we were using terms like, “like Fort Knox for your photos, keeping them really safe.” So we didn’t do any leases on our equipment, we paid cash for equipment, we never have done leases on equipment. The only lease we have is on the building, we never took any debt or anything like that because we just couldn’t risk it. It wasn’t just our money it was peoples priceless photos, their story’s, their legacy.
minute 5 to minute 10

Interviewee: ÖIt wasn’t just our money, it was people’s priceless photos, their stories, their legacy.

Andrew: You’ve got a co-founder in the business, can you tell people who that is?

Interviewee: Yes, he’s my boss and he’s my oldest son, Don. He started the company six months ahead of me, and then spent about four months trying to convince me to join. He succeeded and we’ve been partners ever since. But he’s the CEO and Chief Geek and the boss.

Andrew: I’m actually going to have him here on Mixergy to do an interview about SmugMug where we spent, I think, 90%-100% of the interview just talking about SmugMug. But I wanted to get to know both of you and you’ve got a rich history before SmugMug, so I thought why don’t we do this? Why don’t we talk to you about how you were able to fund the business with half a million dollars? And then, talk to him about how you’re both able to build this business into a profitable business with lots of raving fans. I remember reading Robert [xx] talked about you, guys, like he invented it himself, like SmugMug was his baby. I’ve seen other people talked just that passionately about SmugMug. So I figure I’ll have Don on to talk about the story of SmugMug in more depth. With you, maybe we can start off with what you said before to get to know your history. You worked for Steve Jobs. How did you get a job working with Steve Jobs?

Interviewee: That’s a crazy story. I mean, half of my story is not to be believed, but it’s true, there were witnesses. So, I got a master’s degree in Geophysics, of all things, from Stanford and then went to work as a geophysicist, and for ten years I trotted the globe. One scary incident happened in Colombia that caused me to be away from home for 11 days and missed trick or treat, which was my kids’ favorite thing. I promised them that I would be home for it and I didn’t make it. So we had a family caucus when I got home, and Don, whose idol was Steve Jobs, still is, had done a book report in junior high, ‘The Journey is the Reward.’

He said, ‘Dad,’ during that time of the caucus, ‘why don’t you go into the computer industry? It would be so cool and we could understand what you do,’ and all that stuff. I tried to explain, ‘Oh, you know, I’d been ten years, I’m comfortable, blah, blah, blah.’ They just looked down and they couldn’t understand. I think Don was 13 years old and his younger brothers were 11 and 9, and his sister was 5. So I, after six months, quit, rented a UHaul truck, moved to Silicon Valley, rented a home in Mountain View, and started looking for a job. Fortunately, I had bought a NeXT machine because I was in love with the idea, and the salesman, that I bought it from, hooked me up with interviews, and fortunately, NeXT took a chance on me.

Andrew: So, beyond what your son was telling you about how much he loved for you to work in the computer industry, what was it about the industry that drew you to it?

Interviewee: I think the main thing is someone told me, when our kids were first born, I went to a parenting lecture and some guys said, ‘Most parents try to get their kids interested in what they’re interested in. You don’t do that.’ He was wagging his finger around over the podium, ‘You get interested in what your kids are interested in.’ So Don was a little bit rebellious, he’s got a mind of his own, and his great passion was always computers. So, we would go down, that would be what we do together. We’d go down to CompUSA and buy a motherboard, a hard drive, and some RAM and make our own computers, and that was bonding. I’d buy him a modem and he’d get a BBS(?) set up. From the very beginning, the more I could feed this habit, the more we bonded. So that’s just what I did. It got me interested. Of course, geophysics is pretty technical so I was on computers a lot, it got me interested and him interested and off we went.

Andrew: What is geophysics?

Interviewee: Geophysics is mostly sending down sound waves into the earth and listen for the echoes to come back to determine where earthquake faults are, oil is, gas, and things like that. I often say, there are lots of HDR haters, high definition photography haters, I was doing it as a grad student at Stanford in 1979 in satellites because we had cameras circling the globe. When you took photos of outer space like NASA does or something like that, you had no choice but to do HDR. You’d combined several definition exposures so the stars wouldn’t be too bright and you could bring up the planets and so on. They’re some of the world’s most popular images, but the HDR haters, for some reason, I don’t know why.

Andrew: If you, guys, are haters in the audience and can help us understand, please type it in the chat room or in the comments on the post. What was it about NeXT that drew you to it? You said that you fell in love with the idea behind it.

Interviewee: It’s funny, I was in Calgary, Canada at a bookstore and I was in the oil industry. I just happened to see a book on display that said, ‘The Macintosh Way.’ I’d read the IBM Way and I like to play on words, so I picked it up and started reading it on the plane on the way back to Houston. It was Guy Kawasaki and he was talking about being an evangelist at Apple and how cool that whole thing was.
from minute 10 to minute 15

Interviewee: ÖIt was Guy Kawasaki and he was talking about being an evangelist at Apple and how cool that whole thing was. Just on that plane that I had this little bit of envy like I was missing something really exciting. It must have been so cool to invent the Mac. Those people are so passionate and they sign their names on the inside. Andy Hertzfeld would say, ‘We put love into it and then love would shine back on the screen.’

As I was flying, there was a guy beside me who worked for Novell and he was getting off the plane in Salt Lake and I was continuing on. We got talking about it and I just sort of felt like, ‘Wow! What a cool industry that would be, much more exciting than offshore, joining rigs and things like that.’ That got me interested, and then I bought a Next machine and I love the user interface. I love that the Mac had Cherry balm(?). They were solving the Mac’s biggest problem which is it wasn’t that secure and it wasn’t that stable. They were solving Unix’s most vexing problem which was it was hard to use. It just seemed like what transform the world, and it did. When Apple bought NeXT, the NeXT operating system became the basis of OS X which drove the renaissance for Apple.

Andrew: Yes, that’s what I’m using right now to talk to you, and I’m assuming you’re on the Mac, too.

Interviewee: I am, too, of course.

Andrew: I love this LinkedIn quote, and usually LinkedIn is just dry information, dry information, dry information. When somebody brings it to life, it’s so much more interesting as I do my research on them. I love this line from you about your experience at NeXT. You said you applied the reality distortion field of the ëMaster,’ Steve Jobs, to developers like, and then you list Lotus, Microsoft and others. What did that mean?

Interviewee: So, when NeXT first made me an offer, they made me an offer to go into sales. I can’t believe it but I had the guts to turn it down because I was holding out for developer relations. I’d read Guy Kawasaki’s book and I thought that would be the most exciting thing because you get to see all these developers on what they’re doing. I didn’t realize that developers relations meant you’re talking to Steve a lot. He would call up the President of Word Perfect and say, ‘You, guys, have to do the most revolutionary, greatest app ever on the NeXT machine. It would be the next thing because we provide tools to do software like you’ve never seen before.’

He made that pitch to Lotus and they did this revolutionary spreadsheet, Improv, but didn’t succeed in the market, but it was pretty interesting. He made the pitch to a lot of companies while I ended up being Director of Developer Relations. I ended up chatting around with Steve quite a bit, like companies like AutoDesk and, you name it, Intel, to get them to help us port OS X to the Intel architecture which is the reason that Apple decided to buy it. There’s a story about that.

So I got to see Steve in action, I got to see him sell the idea of doing a movie with Pixar. That was an amazing sales, I got to see him sell an investment to Canada for about $100 million in NeXT, that was amazing. I mean, he’s the best this industry has ever seen. I don’t know if we’ll ever see anyone like him again when he gets up on the stage or in front of an audience.

Andrew: You mentioned a few stories, I’d love to learn from your experience with him. Let’s talk about them or let’s have you share some of them. How about the Canon story? How did he sell Canon on investing in his business?

Interviewee: I’m not sure he’d appreciate me telling this, but I wasn’t as close to Canon as some of the other stories, but I do remember that he put on quite a show and started crying in front of the Canon guy. When Canon wanted to put up some much lower number than Steve hoped for, and I thought the number was pretty big, something like $25 million. I don’t remember exactly. But he started crying and I think he would have been an A-list actor if he could have been. Whether it’s genuine or not, I don’t know, but I [xx] suspect it was part of Steve’s act, but he does it all so very well. Anyway, he came up with this $100 million, and I could give you a few other ones that he did that were just phenomenal.

Andrew: I’d love it, but I’m going to ask you this crying. Usually, if there’s crying in business, people lose respect, the crier lose respect. How did he do it in a way that got him the deal instead of getting him laughed at?

Interviewee: I’ve heard it told that it was a manner of losing face for the Japanese. This guy was sent to do this deal and he’s got the CEO breaking down, one of the great ones of the industry, who’s larger than life, who founded Apple and so on. He’s got him breaking down, and there’s a lot of face lost there, so that’s how he did it.

Andrew: What are some of the other stories?

Interviewee: So, I had a friend who was Vice President of Engineering for Quantum Computers.
Interviewee: Well, so, I had a friend who was Vice President Engineering for Quantum Computers and, as you know, Apple didn’t want a hard drive in the original, or Steve didn’t want a hard drive in the original Mac. Everybody else did and they were hiding an engineer from Sony and so on and Bill tells the story the following way: when Steve showed up at Quantum to see about getting a hard drive when he finally realized it was important, instead of going to the front door and park in the visitor parking lot like anyone else would do, Steve went to the back door and then he waited for the door to swing open and he went in. It was a secured area where you were supposed to have a badge and all that and he started looking around back there at people soldering and working and putting components together and so on and Bill was paged to go back there and get him and said ‘Steve, you can’t be back here’ and took him into the conference room where the CEO was and Bill was and so on, and this is so like Steve ëcause this happened with me in so many meetings. SteveÖ there was a slide projector back in the old days when they had slide projectors sitting on theÖ and a screen set up and everyone sort of dressed up and they wanted to do a presentation to Steve and he says ‘No, I’m not wired that way, I just can’t sit . I can’t do a presentation. I just want to know three things: I want to know the price, I want to know the mean time between failure and I want to know the data transfer rate,’ or something like that, big time. And they said, ‘Well, OK Steve, we’ll just shorten it and give you a few slidesÖ’ and Steve said ‘No, you don’t understand.’ He jumped up and he grabbed a white board marker and he drew three lines on the board. One had a dollar sign in front of it, one had MTBF, mean Time Between Failure, whatever, and handed it to the CEO, and said ‘Fill these blanks in.’ The CEO reluctantly said, ‘OK, Steve,’ and when he filled them of course Steve exploded. ‘
No, that’s crap’ you know, except he usedÖ other words and pounded on the table and said ‘That’s why Apple has to build everything, it’s no good!’ and he ran out and got in his car and drove away. Well, you’d think that’s the method of a madman but I think it’s pretty shrewd actually. I’ve seen it work a lot of times. They’re on the defensive now, they gotta go back to Apple and they sort of grovel if they want this deal and it worked for Steve, I’m telling you.

Andrew: And so they did come back to him?

Interviewee: Oh yeah, Quantum drives ended up in Macs like crazy. But there were ones I could tell first hand, likeÖ how about Unix Expo? SoÖ

Andrew: Before you go to Unix Expo, why do you think that worked for him? Anyone else who does that will be called a baby, will be considered aÖ it just sounds like throwing a tantrum and business people don’t want to do business with people who are tantrum throwers. Most other entrepreneurs who would do that would just be dismissed. Why does it work?

Interviewee: You know, I think it works because Steve makes great products and he can get so much attention for them. Bill Gates used to come down to us every year and I remember he made one crack when he was visiting and he said ‘Only Steve could get this much attention for a black and white education machine,’ and, you know, that was sort of true but, Steve, I mean he’s the best in the world at getting attention and a lot of these stories just increase his legend, I think. But at the end of the day, you know, he doesn’t really hire MBAs that I know of, I don’t know if he still doesn’t, he didn’t back in the day when I worked in his company. He hired people who were product oriented and all the senior execs were product oriented and he himself is intensely involved in every product to get it right because the philosophy was, if you’re a product company, you’d better make the best products in the world because people are going to find out really fast if you don’t have the best products, you know, and you’re a product company, there’s going to be a problem. So when you make products that great, people tolerate you as this creative artist and so on.

Andrew: I see.

Interviewee: There’s a lot of people who wouldn’t tolerate him and who wouldn’t do business with us back in the NeXT daysÖ
Andrew: OK, you were going to tell usÖ I’m writing notes as you’re talking so that I can remember to come back to things that you’re sayingÖ and you said earlier there was a story you were involved in first hand, that you were going to tell before I interrupted youÖ what was that?
Interviewee: So this was Unix ExpoÖ the issue I didn’t expect to have when I joined NeXT was that there would be a lot of haters from the Unix field who didn’t like what we were doing. They felt we were dumbing down the UI, that it was going to be like that Mac, it wasn’t going to be as accessible, that we were going to slow it down, bog it down, complicate it, and take away from the purity that was UNIX where you just have a terminal window open and learn the commands, we’re dumbing it down for Grandma. And I thought, and I know Steve thought, we were doing the greatest thing that could happen to computing, we’re taking a secure multi-user operating system and making it easy to use and making it available to the masses.
Interviewee: …and making it easy to use. And making it available to the masses. So anyway, there were a lot of haters from the Unix community, and they were fan boys at Sun, and Silicon Graphics, which was big in the day. Anyway, the head of Unix Expo asked me if I could get Steve to keynote at Unix Expo. And he said that McNeilly had had 2,500 people the year before. It’s a big crowd. It’s in the Javitt Center in New York, and could I get Steve to do it? And I went into Steve’s office, and he was very doubtful about it because he likes to be well-received. He likes to feel the energy of the crowd. I think he gets at least uncomfortable, but I think he gets nervous if he gets in front of a hostile crowd, and just doesn’t perform, you know, as well as he otherwise would. And his standards are so high. But I convinced him to do it. Money was tight at Next, and he insisted on taking all his gear, the Next Machine, and the desk, and everything else that had to go out there, which was expensive to get them out there. And we set it up, and the conference organizer told me, “We set up 4,000 seats, and there’s people lined up around the blocks in New York. They’re not all Unix Expo people, but they’re Steve Jobs fans. And this is really going to be big.” Well, I was setting up his machine, and he always like to demo the leading-edge stuff, so I would have to sit there in the audience pale, you know, with my hands sweating about whether it was going to crash, and whether he was going to be in a good mood, and show up, and all that kind of stuff. And about 30 minutes before we were going to go live, with those 4,000 seats out there, and people pushing on the doors to get in, he was starting to get pretty pissy. And I would even say, towards a tantrum. And eventually, about ten minutes before the time came, he did blow up. And he took off, and said, “Well then, you give the demo.” Well, this had happened to me before. And I thought, “Oh no, I’m fake St
eve Jobs, but not just in a blog, you know, on stage, in front of 4,000 people. They’re going to be so disappointed. And I don’t even have this demo set up.” And so I’m trying to rehearse it, and figure out what I’m going to say, and why isn’t Steve there. And is he going to be spotted in the halls somewhere, and they’re going to wonder why he’s not in his keynote, and so on. So I told them not to open the doors until I was ready. And when 1:07 came along, seven minutes into it, overtime, and the conference organizer says, “You’ve got to open these doors.” So people poured in, and my heart was 140 beats per minute. And just before it came time to go on, Steve showed up with a big smile, and said, “I’m ready.” And we did all the normal things. You know, he stands in the back by the curtain, and the spotlight has to fall and match his desk. His desk is turned 28 degrees to the front of the stage because the logo is tilted at 28 degrees. No one ever picked up on any of this stuff, except Steve, but that’s the level of perfectionist that he is. The only thing I asked him, and what caused him to blow up, is don’t demo Lotus Improv, because it’s probably going to crash, and we’re not ready for it. And nobody in the Lotus booth knows anything about it. So 35 minutes into this, he was charming everyone. I mean the fans were just so adoring. I’ve never seen anybody able to do this, you know, in the computer industry, in front of an audience. And he pauses for a minute, and looks down at me on the front row, with a little Steve Jobs’ twinkle in his eyes. And he said, “Can I see by a show of hands, who would like to see the most revolutionary spreadsheet that has ever been invented?” And of course, the whole audience went wild. They just went crazy. And I sunk down in my seat. And he smiled at me. And then he did a genius job of demoing Improv. And it held up. And then of course, 2,000 people piled out of there, and went to the Lotus booth. And they
said, “Improv? What’s that?” [Laughs] But it was vintage Steve. You know, I have a thousand of these stories to tell.

Andrew: [Laughs] Wow, I would love to come back and do an interview with you every week, just to get more stories from you.

Interviewee: [Laughs]

Andrew: Who was it? Doctor David, of Wolfsnap.com, is in the audience here.

Interviewee: Yeah.

Andrew: And he said that he just loves to hear you tell stories and explain things. Let me read it directly. “Hey, Chris. Love listening to you explain stuff. You do such a good job.” And I agree. It’s really hard to get people, when the light is on, to come up with their best stories, and to tell them well. And you just give me story after story. No wonder people are loving it. There was one more that you said that you’d tell of Pixar. I’ve got that in my notes. Can you tell that one?

Interviewee: Sure.

Andrew: About the first movie?

Interviewee: Yeah, Pixar was interesting, too. But I think the Intel one is more significant.

Andrew: OK.

Interviewee: I think I told you the one. So we had on our Board of Directors three people, Ross Perot, and a guy who was head of Georgia Institute of Technology, or something, and the Canon guy. Three guys. And I had to set up the board meetings, with all the demo stuff, for Steve one time. And one of the things that had bothered me was that we didn’t show much support for IBM, who had licensed Next Step. They were running it, they were hoping to run it, on their work stations. And we were showing tremendous support for George Fisher at Motorola, who was then the CEO at Motorola, and the Motorola 68000 line, which we were based on, which a lot of us thought was running out of gas. And they announced the end of the line…
Interviewee: …a lot of us thought was running out of gas. They announced the end of the line of the 68040, and then they were going RISC Remember that? They were going to go with the 88110 chip. And so, a lot of companies were bidding on the 88110, and how do you talk Steve out of this position, because when Steve’s wrong, it’s a really difficult thing. He’s right a lot of the time, and we used to say, that he can see what no one else can see, because he’s genius. But he can’t see the obvious. Like when there were 350 employees, 349 were against putting that magneto-optical drive in there that almost killed Macs that we shipped with, that slow, clunky, expensive thing, and only Steve wanted it in there. He later regretted it and said ‘I wish people would have talked me out of it, because I had such a great thing, this Graphics User on top of Unix. The next step was so great. Why did I bet it all on magneto-optical drive and put that in the critical path? It was just stupid.’ So, anyway, I decided to just take some guts and call Andy Grove, because I thought Andy Grove could talk Steve into possibly porting over to… Steve, it was my opinion that Steve related well with older men who admired him, like John Warnick at Adobe, he loved him. He loved George Fisher at Motorola, and I didn’t know what his relationship with Andy Grove was, but I thought Andy was the kind of guy. So, I called him, I don’t think I ever told this story in public. I called him and got his assistant on the line who is an executive in training for two years, 30-something I think, executive that got to work for Andy Grove for two years. And he’s a really nice guy, and I said ‘hey, if you ever reveal to Steve that I’m making this call, I’m out of a job. But I think it’s in his best interest because I think you guys have chips that we don’t have to convert to RISC, or something like that.’ And so, I explained the whole thing, and he arranged for an audience for me with Andy Gro
ve. So, I went down there and sort of under cloak and dagger, secret circumstances, saying, here’s the way to appeal to Steve, and here’s the way I think it will work. One, I don’t think he wants a big team to work on this, but he needs a couple of really bright engineers. Get your best guys. Don’t compromise. They just have to really be great. And get them to work up at our place to help us port this over. They have to know all the nuances of all the primitives, and so on. And a little bit of funding would help, I don’t know what you can spare there. And admire Steve for what he has done, for what he has done is brilliant, and he’ll feel a lot better about it if you do. And
Andy came up in the meeting that I knew about, because Steve told me about, but I wasn’t professing to Steve that I had helped precipitate it. And with, I think, every Intel Vice President, and Steve met alone with them in the conference room. As far as I know, this story is dead accurate. And they came to a deal. There was some number of millions of dollars that Intel paid, and there were two engineers who were great guys who came up and worked on it. And on a Cray 8486 66 MHz machine, in 6 months, we had Nextep running on my desk and we had a black blanket over it, because I wasn’t showing anybody. And everybody predicted it would be slower, but actually, it was twice as fast as it was with the Motorola chips because the clock rate was twice as high. And the graphics primitives began. It just, it didn’t matter, it all went by clock rate. And once we had that, I thought it would be so clear to go to Intel architecture. Well, we didn’t go to Intel architecture, I don’t know why, but we had the port running. Well, along comes Gillimilio, the CEO of Apple, he’s got a problem, because there’s cherry bombs and instability with Mac OS, and he goes shopping for another OS. And who should they get, the vanquished hero Jean-Louis Gascet with BOS, or should they get this guy who’d been so difficult for them, Steve, who had been really pushed out, and a lot of engineers were afraid of him with Nextep. Well, I did an intro when Gillimilio, when he wrote a book on how he saved Apple in a computer literacy bookshop in San Jose. I was sitting by John Marcov of the New York Times on the front as I sat down and Gill gave his talk. John asked the first question, which is ‘Gill, why did you buy Next, the operating system, or Next, instead of B?’ And Gill responded ‘well, that’s a very good question, and that was a big debate within Apple at the time, because a lot of the engineers wanted BOS. It was technically a very good operating system. And people felt a very
strong bond for Jean-Louis Gascet. But the answer was that Nextep already ran on Intel architecture, and that was important to us, and that was what made the difference. So, we bought them.’

Andrew: Wow.

Interviewee: That was, John Marcov sitting beside me and I thought, nobody knows this story. I’m going to have to sit on this story for ten years, and I think it’s probably been more than that now. And it’s that call to Andy Grove that helped precipitate it. So, maybe Steve should give me…
Interviewee: And it’s that call to Andy Grove that helped precipitate it. So, maybe Steve should give me one share of stock or a new i-Pad or something like that because I think that was the purchase that changed the world. Certainly changed the computer industry.

Andrew: Why did nobody know about it for so long?

Interviewee: Well, I wouldn’t tell anybody.

Andrew: Why?

Interviewee: Because I did something that probably would have got me fired. And, I used to have a notion about what you do if Steve’s wrong. How do you talk him off the ledge if you really think he’s wrong? And I used to be one of the designated guys who used to go in there and try to do that. And he has so many ways of getting his way when he’s right. First off, he’s larger than life, because he started Apple and you didn’t. So, you give him a lot of room. Second, his clock speed is faster than yours is, except for Ross Perot’s. For some reason, Ross Perot could debate with him in real time. For most of us, he’d get ahead of us, anticipate what we were going to say, cut us off midway in our sentences, and we would have to go out, collect ourselves and go back in. Third off, he has access to information you don’t have, because he says ‘Oh, I just got off the phone with the CEO of IBM. He said blah, blah, blah.’ And well, you don’t have that information. And then he’s, and he’s more charismatic than you are. He’s more charismatic than anyone. So there’s four ways he can get his way when he’s wrong. And the fifth way, which he will use, is if the first four don’t work, then he will start challenging your heredity and get all personal about it, which you can’t do in return. So, I used to hold the corners of my mouth down when I was talking to him, and he’d start to challenge me, saying I was immature and all that. Because I think if the great Steve Jobs has got to use that to win his argument, then you know you’ve won the argument. Just get out of there. And three days later, he’ll send out an e-mail, maybe, and say, ‘hey, I’ve been thinking, maybe we should consider this.’ And if that happens, that’s a great thing. So, I just never wanted to go around and say, ‘see, Steve, I was right.’ I never wanted to put it in his face, because I wanted to make it easy for him if he was wrong, because he’s a celebrity, and in those days, it was hard for him
to be wrong. Probably now it’s not hard for him to be wrong. But in those days, it was. So, I didn’t want to go back to him and say ‘hey, I played a trick on you with Intel, I just heard some credit. Nothing seemed right about that, so I just let it lie.

Andrew: There’s a whole chapter in Dale Carnegie’s ‘How to Win Friends and Influence People’ about that. I can see it. I can see why you have such a good relationship with him. Why didn’t Next take off?

Interviewee: The operating system was pretty pitty. And back in those days, it was $7500 per workstation. We were able to sell 3000 of them a month at its peak, but Apple was selling their high-end MacIntosh 75000 a month, so it was hard to compete with that. [lost audio] it would normally cost $8000, because it would take…

Andrew: Why so much? If this is supposed to make you much more accessible, why such a high price tag?

Interviewee: Well, all Unix machines were at a high price tag, because the operating system took a lot of memory, by those days’ standards. 8 MB was a minimum, and in those days, if you had an 8 MB station with a 40MB drive that had a fast enough processor to run it, you were up around 6, 7, 8000 dollars. And you could buy a PC for $2000 that ran Windows. So that was a big problem. We had to sell it to the financial sector that wasn’t too price sensitive and directly, on Wall Street and the Chicago trading floor and things like that. Now, I mean, it took more resources than we had in those days. Now you can pretty much put a stripped down version on an i-Phone and have it in your pocket.

Andrew: What do you think the company should have done differently?

Interviewee: Next, should have done differently?

Andrew: Yeah, it goes out, it starts out business with one theory, and the theory ends up being too tough to execute. What do they do?

Interviewee: Well, it was a huge mistake to put that magneto-optical drive, which killed the first release of the product. And then, we were quite ahead of our time with the size of the operating system. But one little piece of insight. We had a focus group in New York City that Mike Sade arranged. He was the vice President of Marketing. He used to be at Microsoft. And he got Steve to go to the focus group. So, Steve himself was behind the one-way mirror. And we’re talking to all these IT directors about various different workstations. They didn’t know who was sponsoring it. And we asked, if workstations were cars, what cars would these workstations be? Well, they decided Silicon Graphics was a Lamborghini, and Sun was BMW, and that a Mac was an Accra Legend, an IBM R6000 was a Chevrolet, and HP was a Ford. What do you suppose they decided the Next was?
[Missing audio from minute 35 to minute 40. The transcribers are fixing it now.]
Interviewee: …before, you know, people really realized it was SEO. The publishers would provide links to us. Back then, O’Reilly and Prentice-Hall, and some of them would provide links to us, you know, to buy books. I don’t remember that traffic was the really hard part. Oh, we also had a corporate program that was really important. So the librarians, at places like IBM, and Sym, and Cisco, and so on, would set up an account with us. And so all the geeks to their company would be instructed to buy books through us, or encouraged to buy books through us, which was generated. I think that’s where we got most of our traffic.

Andrew: I see. I think Staples used to have something like that. But I don’t remember Amazon having it. That’s the program where you give a special landing page, just for people in that company. They could go in and buy it. I see. How did you come up with that?

Interviewee: You know, I think we just sat around and came up with it. We had to do something to fight off Amazon. Amazon was the fiercest competitor on the web, by far. We’d never seen a company like that. I mean they, after their six million dollars they raised, ten million from Planter Perkins, and John Dorr got on the Board, and they became the darlings of the internet. And then they were able to do that big public offering. And it’s always been an interesting company. And they were very talented. They did really good products. They were so good at everything. You know, something…

Andrew: So how did you compete against somebody so good?

Interviewee: You know, they used to terrify me. It’s funny now, that we’re very close friends with Jeff Basos, my son Don looks a lot like Jeff, and you know, they’re both sort of thin, and geeky. Excuse me. And sometimes they’d end up at conferences together, like HEAD, and they’ll switch badges with each other. And Jeff will put on Don’s red hat, and Jeff will answer questions about SmugMug, and Don will answer questions about Amazon. I mean, don’t know the difference.

Andrew: [Laughs]

Interviewee: I think we’re one of Amazon’s biggest customers now because we store all our images. We do all our image processing at Amazon, and so on. But back then, they were just so fierce. I didn’t think anybody could compete against them. What we tried to do is, there was an ad up on my wall that we still have. We had this attitude for geeks. The ad said, “When your IQ is higher than your body weight, you can’t always find what you need at the family bookstore.” And a lot of provocative ads like that. And we had selection far beyond what they had. We printed on demand, like all of Amazon, or all of IBM’s technical manuals for their systems, and all of Sun’s technical manuals. We sold CD-Rom training, which was big in the day, and just a lot of stuff like that.

Andrew: Is this true? Doctor David is saying, “These days SmugMug is the single largest customer of Amazon, due to S3.”

Interviewee: You know, it’s possible. I’m not sure because Amazon doesn’t disclose those numbers. We had two pedabytes of storage up there. I had thought I heard rumors that Dropbox was going to blow by us. But I don’t know the whole picture because we use an awful lot of EC2, for video encoding, and for image rotation and sizing, and all that kind of stuff, too. So the total bill from Amazon, I don’t know. I would think we’d have to be one of the biggest, but I don’t if we are the biggest.

Andrew: Oh. Andrew SG is asking, “How big is your Amazon bill at SmugMug?”

Interviewee: Huge. It stabs me in the heart every time I see it.

Andrew: Really? Is that…

Interviewee: [Laughs] It’s big. I…

Andrew: Can you give us a sense of it?

Interviewee: I don’t think I can because I think the contract we signed with Amazon wouldn’t allow it. And I’m just not sure about that. I would have to know that first. But it’s a huge bill. Just think of, you know, you could do some of the math because you could figure out what two pedabytes of storage costs up there, from their published storage rates.

Andrew: But we’d also need to know how much is going back and forth to really know the number, right?

Interviewee: So there’s a lot.

Andrew: So they charge for storage, and they charge for in and out.

Interviewee: That’s right.

Andrew: All right. Maybe somebody in the audience can give us a number on what the storage costs would be at least. And obviously, the in and out’s pretty expensive.

Interviewee: And you have to predict how much image processing we do. You know, we do a lot of it with them.

Andrew: Right.

Interviewee: Every image. You know these images are pretty big. And they have to be, you know, a lot of things happen to the image, before they get inserted into our database. So we use a lot of EC2 time.

Andrew: Fair to say that over half of your expenses are Amazon?

Interviewee: No, no.

Andrew: All right. Let’s go back to Fat Brain. You launch it. There’s a company called Computer Literacy Bookstore that apparently is big in the computer industry. Everybody loves them.
Andrew: …apparently is big in the computer industry. Everybody loves them. They sue you. How do you end up buying them after they sue you?

Interviewee: Our domain name, you’ve done your research. Our domain name was cbooks.com. And their domain name was clbooks.com. We had no idea when we got the domain name. So, they tried to sue us for poaching off their domain name, from misspellings and things like that. It was a pretty weak lawsuit. But, it was an introduction, we got talking to them. Our venture capitalist liked them because they just drew so many geeks into the stores, and they had so much inventory, and they could ship right away, and they had a good reputation. So, our venture capitalist wanted to buy them and he stepped up some money to buy them. I told them in retrospect, I wouldn’t have done it. I would have just focused on the online presence, but we did it. And it sure stepped up our sales.

Andrew: It did. It helped. It took the company public. Why? This was ’98, before everybody was taking their company public, just as that trend was starting to get big.

Interviewee: The way I recall it, there, public offerings waxed and waned. They waned before Amazon went public, and then when Amazon went, they sort of broke the logjam for a while. Yahoo broke one of the logjams, I know Amazon broke another, I can’t remember. We were the only, there were out going public when we went public. One of them was e-Bay, and one was us. We were best friends with e-Bay. Gary [Majaro] used to work for me. He was a tech support engineer. I gave permission to use the MacIIci, that’s all another story, at our company to do e-Bay. It was Auction Web, I think, at the time. E-bay was in the [bola] web site. Anyway, we were on our road shows at the same time, and we were asking ourselves why we were going public. And basically, it was to raise more capital, to raise the profile of the company. Amazon had raised more money than God. They had raised $3 billion by that time. We just needed more capital for expansion, that is what it boiled down to.

Andrew: Here’s something I saw too in the research. In 2000, Barnes & Noble buys you for $62 million in cash and stock. At the time, the company had a loss of $10 million in that quarter. With but 5 out of 6 analysts who were following you had either a buy or a strong buy on the company. So with Amazon in the business, and with Barnes & Noble in the business, and with your loss, you were still able to win over the analysts. How hard were they to win over at the time?

Interviewee: No, they weren’t very hard, and the reason is that Amazon had such huge losses. And their $3 billion in debt that they went into was accepted pretty much at the time. Amazon, or Barnes & Noble, raised $450 million in their public offering. And everyone thought there would be 3 survivors. The consumer could remember 3 brands. There would be 3 brands that fought, and two of them would, one would be Amazon, one would be Barnes & Noble, and the other would be us. And in order to do that, we had to spend and endure losses to make that happen. That was just the thinking of the day. And that thinking for the day did work out for Amazon. I mean, they ended up building a big, great company. I mean, even Google, lately, they raised a lot of money and they had a lot of losses before they ever started to make it profitable. So, that is just what was thought you needed to do to start an internet company in those days.

Andrew: Why did you sell?

Interviewee: Because it was 2000 and everything was collapsing. We had to. The stock was down, basically. And I had already gone to start Mighty Words. I know you mentioned Mighty Words before. So we had made Dennis [Peppegillo] the CEO of Fat Brain, and he continued on after it was sold to Barnes & Noble. And Barnes & Noble [lost audio] Mighty Words because they were interested in electronic, sales of electronic media.

Andrew: Barnes & Noble invested in Mighty Words, you said. Sorry, we lost the connection. Has that happened?

Interviewee: Oh, sorry. Yeah, so Barnes & Noble invests $20 million in Mighty Words, which was a spin-off of fatbrain.com. And they wanted me to run it.

Andrew: I see. What happened to Mighty Words?

Interviewee: So, that’s an interesting story too. I have lots of stories to tell about that one. So, the idea behind Mighty Words was that there was, at least my founding idea was, there was no way to publish something for sale that was longer than 3 pages or shorter than a book. In other words, if it got longer than a magazine article, there was no way to publish it, unless it was long enough to be a book. And the internet provided this mechanism to where you could sell content that was in between.
interviewee: The internet provided this mechanish to where you could sell content that was inbetween. that day had died back when charels dickens wrote a christmas carol and cerealized it in the london times, he was able to do it because cerealization at the time so he could sell a short story but it would all be die. you and I and everyone else can site all of the buisness books that we want to buy, the intivators delema and so on by clayton christinson, he’s a harvard buisness professor. It is a great book but he said you know i really thirty, fourty, fity pages in the manual script of really good stuff and what most people wanted to read. But i had top blow air into in order to make it a book so the spind would be think enough and the price high enough to sell through barnes and noble, and borders and everything else like the kind of merchindiseing they did. so that was the founding idea, that we would sell PDF’s basicaly and any other electronic media that came alone and who knew what would happen i books and i phones and everything else but it would enable you to sell electronic media for cheaper. well the problem we ran into was the publishers not wanting to give their content and Amazon has only been able to crack that code with the way they did kindle, major credit to how the have done it but we werent able to do that, not with the publisher we would go in and if people wanted to copy then you know how it is.

Andrew: you where also trying to get new content created just for sale through this new medium right?

interviewee: we where

Andrew: and how did that go?

interviewee: we had some sucess with that, but for example we decided for a launch that a good way to show medium lenght content was compeling was to write about the ten amendments because it is still valid today they are contriversial. lets call on ten great authors to write about the ten amendments, i didnt think to go through book publishers because this wasn’t book content, it was twenty and thirty pages, so we just contacted the authors directley that we thought could write about these ten amendments and we got some verry amazing authors, dorse curnes was a good one who wrote team of rivals which was about Abriham lincoln that obama sofanda. i didnt know it at the time but she is in the midst of the book one of the ones we called and she instantly said yes and asked if she could get help from her husband a great constitutional scholar. they wrote the first amendment then the next thing i got was a frantic phone call from the CEO of simon a chewster, and my wife handed me the phone in the shower and he said i want to see you here tonight, so i went to the top floor of the simon chewster building and this guy sits me down. I’m low and the couch and this guy is up high and he is acting like i just commited this enourmous crime because she is behing in he lincoln biography and i am setting her farther behind, and they have rights to her and who did i think i was. He said he was going to poison my name to all publishers in New York. it was just the worst talking i have ever had in my life and i used to work with steve jogs and that says alot, i got treated likewise by other publishers you know we had steven king write a short story and as soon as his publisher heard he acted like i comited a crime and it just kept going down the line and it was agents against publishers

Andrew: in 2002 you shut it down, can you explain your thinking behind that, here you are a guy who had a sucessful track record and now you are on to the new new thing that that was suposed to change the industry and now it’s not going so well. What was that like?

interviewee: it was the hardest thing i have ever done, we still had alot of money in the bank and we didn’t have a high burn rate, so we could have lasted a long long time but i had taken alot of money from investors like barnes and noble. Steve richio had become a verry good friend and he had become president of barnes and noble. i just called Steve up and said look i don’t know what to do because the publishers were so against stuff and they were going to stop their offers from coming to us, the kind of content we were coming up to with an open sort of mind, and the submit your own content wasn’t compelling enough and they didn’t have the marketing behind them.
Interviewee: …you know, submit your own content is not compelling enough. And they don’t have the marketing behind them. And you know, it’s hard to be an independent author without a big history machine marketing partner. And these guys just won’t do it. They’ll blackball any publisher. Even Arthur C. Clark they blackballed, for coming and writing a short story for us. So Steve, I really think, rather than follow it all the way to bankruptcy, and everything, the inevitable conclusion, this is something ahead of its time. And maybe Amazon, or someone, Barnes and Noble, can solve this years down the road. But I can’t solve it today. So I eventually convinced him into taking his money back, and liquidated the company. It’s a most unusual thing. And no one ever does that. But I just thought I’d rather work on something that I could succeed at. I’d seen a quote from Warren Buffett, where he’d said… Ah, I’m going to butcher this quote. I remember him saying that for some companies, the CEO running them is like putting the CEO in a speedboat, with you know, a V-12 engine. And it just… And for other companies, you know, it’s a rowboat for this very same person to run it. And this one just looked like a rowboat, a leaky rowboat.

Andrew: I see. And did you know what you would do next?

Interviewee: No, I thought I would take some time off and travel around the world.

Andrew: And that’s when Don got you.

Interviewee: That’s when Don got me. That’s why he had trouble convincing me to do this because, first off, you know there were a couple of things that had happened in the meantime. I was at Ground Zero on 9/11, which was a big influence on me. We had a board meeting, a Mighty Words board meeting, that was in a BarnesandNoble.com conference, that was in the south of New York, and overlooked the Twin Towers. And Steve Rizio, my good friend from Barnes and Noble, saw some smoke coming from one of the Towers. He said, “Oh my gosh, you know, my aunt works on the 104th floor there. And he got all flustered, and so we decided to cancel the board meeting. And then, while I was on the phone with him, on the way to the board meeting, they said, “Oh, there’s another plane coming to help. I guess it’s a military plane.” And they were describing it. And then they described it with gasps, as it ran into the Towers. And here I was, you know, down there by the Towers, and that was quite a day. It was quite a week, we spent with the Rizios and with various others. We were trapped in New York for eight days. It’s kind of a life-changing thing. And so that, I did a lot of soul searching about having to be in New York all the time, with those publishers yelling at me all the time. And you know, how I was having trouble getting Mighty Words to get traction, so I was thinking at that time about winding it down. And that might have been the precipitating event that really got me thinking along those lines. And then, you know, I thought I would take some time off. Get over it all. Travel around the world. And then Don filled me into SmugMug.

Andrew: Before I take questions from the audience, I’ve got to ask one of my own. And guys, if you do have any questions, just type them into the chatroom. What’s it like to work with so many family members? How many guys do you have now? How many family members at SmugMug?

Interviewee: Nine, if you count two of my daughters-in-law. [Laughs] So that’s a very good question because I worked for Don, my oldest son. Then we hired Ben, which is his brother, two years younger, who became in charge of help for awhile. And I was in charge of testing. He is doing a really good job. And so my office is right across from his and Don’s every day. And then we hired Mark, two years younger still, and he’s in testing, working for Ben. So my kids are not shy about saying what’s on their minds, and you know, when they’re frustrated, they speak up. It’s just like a family. So when people come into the company, and they see us in active, spirited debate about “Shouldn’t we do the UI this way, on the new iPad app, instead of that way”, and everybody’s arguing about it. We don’t see it as a family argument. We see it as a very engaging, active, spirited debate, but it takes a little while for other people to see it the same way. Of course, I came from working with Steve Jobs, so everything seems milder after that. But sooner or later, the other members of the “family”, as we call them at SmugMug, become like the brothers. [Laughs] Mostly, and they speak up about anything that’s on their mind, all the time. And you know, I don’t remember ever having any real family meltdowns, although Annie, who is the fourth one, the girl, she annoys the brothers a little bit, like she did growing up. But everybody else in the company loves her, so it’s all fine.

Andrew: Wait. You see when family members get together for the holidays that they all go back to their old roles because that’s just the family dynamic takes over everything else. Does that happen at work?

Interviewee: I’ve never been asked that question before, and I’ve never really thought about that, that way before. You know, I guess we just see work diffferently than we see family.
this audio has been very useful for educated persons.becase checking their mind power.
Interviewee: …graduated with a Master’s in organic chemistry. She got the dream job of her life, which was cancer research. She had a son, which was me, which she always dreamed about. But she, unfortunately, was struck with adult schizophrenia, which is a devastating mental illness, and probably responsible for 50% of the street people. She got to California, I presume, because of the liberal mental illness laws where you can’t be detained against your will for longer than 3 days. And she sent a telegraph to my parents and got me out here when I was, whatever you are in second grade. And then, we couldn’t maintain our apartment, she thought the communists were going to get us, she put me out of school, and so on and so, for some years we lived on the streets. And so, I ended up in later years having to speak about that, even at Stanford, in front of a huge audience and so on. And it was so frightening to tell those stories that I went and bought books and checked them out of the library, on public speaking. And I practiced for hours and hours and hours. So, this is a true story. When I went to Stanford, my professor was Dean of [??] Sciences, and huge reputation, and he asked me to speak in front of the largest donor that the university had at that time, with a huge audience. It was Cecil Green, that’s who the Green Library was named after. I think David Packard has since become larger. So, I was his host for the day, and I had to give this 10-minute talk, and it was on why I appreciated being at Stanford. And I wanted to, for the first time in public, tell people that I used to be a street person. And my mom dreamed, that the one wish she had for me, that I would go, like she did, to get a Master’s like from Cornell. And the thought of that talk was so terrifying. I was asked to speak in May for a talk in August, that I read every public speaking book, I walked down sidewalks to and from work speaking to trees and parked cars. I set up tin
cans in a closet and I spoke to them to get used to audiences not laughing at my jokes. And I just really worked on it.

Andrew: Wow. What was, well, do you have any advice for somebody else who wants to make that kind of dramatic improvement?

Interviewee: Well, so I…

Andrew: …or resource?

Interviewee: I’ll tell you what it’s coupled with. When I was accepted to Stanford, I was in the 33rd percentile on the writing and reading comprehension tests. And so, when I got to Stanford, I had Don, the CEO of SmugMug on my shoulders, he was two years old at the time. He was just something I could fiddle with, because I was nervous, because I was meeting this Dean of Sciences who was my advisor, who was larger than life. And I had never been on the campus before, and I didn’t feel I belonged there. And I even had to bring my letter in my top pocket, to justify, to remember that I had really been accepted. And when I got into his office, Dr. Cox said ‘Chris’. He was a man of few words. And he said ‘Chris, can you tell me about your low achievement test score in English, because we debated that a lot before we accepted you’. All the other students were from Cornell and Princeton, and I was from the University of Utah. And I was feeling like I didn’t belong in, when he leads off that way, I thought I would vomit on the floor. And so I laughed nervously and said ‘I don’t do English sentences, I do equations. That’s why I chose your physics, to get as far from English as I could possibly get. I never want to take another English class as long as I live.’ And he had reading glasses on because he was looking at my file. He took them off, set my file down, and looked at me for a minute. And I thought time would stand still, and that I would wet my pants. And he said ‘well, I have some very bad news for you.’ What I thought he was going to say is, we can’t accept you to Stanford after all. Or, we made a mistake. Or, we didn’t notice this. Or, something like that. And what he said is ‘in order to become a great scientist, which is what you come here to become, you have to become a great writer, because it won’t do you any good to become a great scientist if no one knows about your science. You have to write great in order to get your writing accep
ted. And you’re here for two years. You have to write your own master’s thesis. No one can write it for you. And I have to grade it. And if it’s not great writing, I’m not going to pass you.’ And that was it. I thought about telling him about my mentally ill mom and the communists, but he didn’t seem like the man who would understand. I never really told that story before. I thought about running, like I used to do, when I started elementary school again, and in the sixth grade. And I just didn’t understand what they were saying in there, and I’d get scared, and I’d just run out of the classroom. I didn’t know what to do, but he had me trapped. So, the only thing I could do was decide I’m going to make a 3-hour a day study of English. I’m going to, whatever it takes, [Strunth & Weyth], ‘The Elements of Style’. I’m just going to go to the same place everyday and study for 3 hours and do this. And I picked writers who weren’t trained to be writers. Abraham Lincoln and Winston Churchill and Mark Twain, and decided I was going to learn it on my own terms, not on the terms of some English Literature class that taught Shakespeare. And it was just survival. It was desperation, it was street instincts kicking in, and it’s paid off for me ever since. One of the greatest writers I know is Steve Jobs. He’s, I don’t know how he got so good.
Interviewee: One of the greatest writers I know is Steve Jobs. I don’t know how he got so good. But if you watch his Stanford Commencement Address, you could see how good he is. And he used to have me write some things for him. And I think, “Oh if you only knew. You know, I’m the retard kid who got Ds in English in high school, and got expelled from UC Santa Barbara my freshman year because I couldn’t pass bone-head English. English 1A, I couldn’t pass it in three attempts. And here I am writing some press releases for you. This is crazy.” But now I love it, and I study it, and everything else. But it just took fierce determination.

Andrew: I’ve noticed… Hmm-hmm.

Interviewee: That leads to good story telling.

Andrew: I’ve noticed that. The entrepreneurs who I interview who are the most persuasive, the most enjoyable to listen to, end up being writers first. And that’s why they can share their ideas so well here because they’ve thought them through on paper. And they’ve had the skills, and the time to learn how to think ideas through enough, to communicate them, at first to a piece of paper, or a computer, or a blog. And now to just talk to me, it’s a lot easier.

Interviewee: You know, Robert Redford said something that stopped me in my tracks at the Sundance Film Festival. Somebody asked him, “What’s common among the filmakers who succeed at Sundance?” And he said that it’s the script; it’s the writing. That’s the bottom line. Most people think it’s the cinematography, the acting. And they’re very self-conscious about that. And that’s where they spend their effort, not that it’s the story or the script. It’s how it’s written. And I’ve always clung to that and thought, “Wow, that’s right, isn’t it?”

Andrew: How did you and your mom get off the streets?

Interviewee: Oh boy, I got caught shoplifting, and went to Juvenile Hall, and had to face a juvenile judge, and everything else. My mom, I knew she was mentally ill. She and I always adored each other. And then I don’t know why, we just always adored each other. And I don’t remember having an argument with her. I loved her with all my heart. Even as a young kid, I didn’t argue with her about… Maybe I was sympathetic because she was mentally ill. And I knew not to believe anything she said, except for this one thing, which was she said, “If you ever get caught by the truant officer, playing hookey, you’re going to go to San Quentin for life. We can’t let that happen.” And it’s like well, “Of course I’m playing hookey because you don’t let me go to school. And you know, who is this truant officer? He’s going to come and get me and take me away.” And I thought that’s where I was, you know, when I was in Juvenile Hall. And somehow they, I’m not sure exactly, but I think they found my father, who I thought was living where I was from. And he lived in Winda, which was an upper middle class neighborhood across the hills from Berkeley. And they put my mom in a mental institution in Martinez. And then my dad took me to start sixth grade, two weeks into it. And I wouldn’t tell anybody about, you know, the school that I lost. So I went in the classroom, and when I walked in, the kids were doing times tables. Seven times eight is fifty-six. Seven times nine is 63. I was like, “What are they doing?” And then Mrs. Gibbons asked one kid to go to the board and diagram a sentence. And they went up and drew these lines on the board, and filled in some words, and said one is a prepositional phrase. And I just, that’s one of the first times I ran, you know, when she asked me to do that. Because it’s like, “I don’t know what you’re talking about.” So I got put in all the slow learning classes. I was diagnosed as having a learning disabililty. And that sort
of got me back on track, you know, all these angels, in the form of teachers who work with special needs students. You know, I wish I could go back to them today and tell them how grateful I am. But they sort of… And I got held back a year. But they got me into high school, and from there, I sort of gradually made progress.

Andrew: Michael Okowski in the audience is saying, “It’s incredible you overcame all that. I can’t imagine how difficult that would be.” I can’t, either. Andrew SG is asking if you’ll be writing a book eventually. Have you considered it?

Interviewee: I’ve considered it, and people have asked about it, yeah. I’ve thought about it. I actually, you know, as many times as I’ve told the story, it’s still hard, a little bit, to tell. You know the first time I ever really confessed to anyone was when I was dating my wife. I met her at a summer camp, after I got basically expelled from UC Santa Barbara for not passing English. And it was a ten-week summer camp. And we were falling hopelessly in love. And eight weeks into it, I had to kind of say, you know, she had a Bachelor’s degree already. And she was 21. I was 19. And she got a Bachelor’s degree. Phi Kappa Phi, that sounded fancy, like fancy. You can’t be a male and be a total flop-out, and have your best girl be a college graduate. I mean what is that. But I had sworn I’d never go back to college. I was so angry after I got expelled, I just would never do it. So I had to kind of gradually, you know, confess to her a little bit of what had happened, that my family is crazy. And that I, you know, couldn’t go to college anymore because I was expelled. And she took enough sympathy on me, and tutored me, and got me back into college on a non-degree seeking basis, until I could get my grades up.
Interviewee: . . . until I could get my grades up and we’re still married today, thanks heaven.

Andrew: Wow.

Interviewee: So, but, anyway, when I’m asked to speak about I sort of have this hangover for about two or three days, you know, just because it’s, you know, some of the stories I can’t tell and it go back to sort of a dark time.

Andrew: Does your family know? Do they know the stories?

Interviewee: No. I’ve told them repeatedly there are a dozen of stories that I’ll just never tell. I just never will.

Andrew: Never?

Interviewee. Never. And so Don actually coached one out of me on instant messenger, one time. We weren’t in the same room. And so I, I had spoken, you know, he and another guy had started a business club called The Bomus [sp] Club and it’s open now for a while. And they had me as one of the speakers. And it took me a long time to get ready for that talk and then give it and then get over it. But, of course I wouldn’t go to some of the darker stories.

So, that night after he was thanking me on instant messenger I finally said, ‘Okay, there is one story I will tell you. But, I’m only going to say it once and I’m never going to tell it again. And so I told him and I was weeping and then I managed to tell it a couple of years ago to my daughter. And, but, they understand after hearing that story why I would never tell it anymore. So, that’s just the relationship we had.

Andrew: Why wouldn’t you? Not that specific story, buy why there’s stories you still wouldn’t tell?

Interviewee: You know what? It’s funny because we live around some World War II veterans and many of them won’t tell stories about their World War II experiences. So, I went to one of them who was a Balladeer over Italy and had amazing experience, to ask him to speak to a group of teenagers and he wouldn’t do it. And then I said, ‘You know these memories are priceless and they’re going to be lost and people won’t know. This generation needs to know. And it would be such a great public service if you would do it.’ He finally agreed and he gave the talk and he was glad he did it after he gave it. But, it took him 50 years before he would give that talk.

And now he gets asked to speak a lot and he rarely does. He’s in his 80’s. I asked my father the same thing. He was a World War II vet. He was a Canadian in North Atlantic (xx). I asked him, ‘Why won’t you ever tell me stories about the war?’ And he said, ‘I’ll tell you one, then you can understand why.’ And he said, ‘I was the Left Tenant’ they called them Left Tenants, ‘in charged of the flight deck

And in the North Atlantic we couldn’t turn on our lights at night because the Germans would find us. And the ship was pitching in great seas and high winds and so on. And my best friend in line was a pilot and he landed his plane on the deck okay, but the plane caught fire and I had to follow procedure and push him overboard, order him to be pushed overboard.’ And he said, ‘I never got over and I never want to talk about it as long as I live and I don’t want to talk about any more stories either.’ And he was mad at me for asking, basically. So, I shut up and never asked him again.

So, that was that. So, I learn what I can, what I’m able to tell and what I can’t. A few years ago I took a long term in Oakland and I went back to my old neighborhood in Oakland and I just wasn’t prepared for it. I don’t think of myself as someone who would have post traumatic stress or anything like that, but I remember I started breathing hard and sweating and all I could think about was driving out of there.

Andrew: I hope, and I know your family does and I can see that anyone who has heard us here today does to, we hope you will tell some of these stories. But, I can now understand why you wouldn’t want to. Well, how about this? Let’s end it with Don. I’m going to get to interview him next.

Interviewee: Okay.

Andrew: I don’t ordinarily interview two people from the same company, but I heard a little bit about you for years. I said, ‘I’ve got to talk to each one of them separately.’

There’s too many stories here in Chris’s experience and I obviously didn’t know how many exactly. And then of course, Smodmothers [sp] is such a successful business. And such a beautiful business in that it started off so simply and that it caters, it gives people what they need so elegantly that I’ve got to figure out how you did it. And so I thought I’ll do two separate interviews. So Don, I’m not sure when, is going to be here in a few days. Do you have a question that I should ask him?

Interviewee: You’re asking me?

Andrew: Mm-mm.

Interviewee: That would be . . . good question . . . I would to hear why he worked so hard to get me to join the company. [laughs]

Andrew: Okay.

Interviewee: Because he spent about three to four months and I thought I was sort of damage goods, you know, after the 911 experience and everything else and shutting down Mighty Words. And he was really starting to gain companies, it’s called (xx) and we renamed the company.

Only a piece of it was photo sharing.

I’d love to hear what was going on in his head.

Andrew: I’ll absolutely do that.

Thanks for coming on here.

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[This interview was suggested by my friend Jason Baptiste of Cloudomatic.]

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  • http://www.girlstartup.com Girl Startup

    Fantastic. Such great insights into Steve Jobs. Chris sounded like he was a bit like Steve's good little angel. I would of loved to hear Chris' full story on his life as street kid. What a great story teller, he's so articulate, and his voice draws you in.

  • http://twitter.com/mrakowski Michael Rakowski

    I liked the Steve Jobs stories too. I thought I had read every Steve Jobs story but these were new to me. An entertaining insiders perspective of the NeXT days.

  • briteguy

    It is a very moving interview, especially the parts that they lived on the street and about his father and world war II. I like this type of interview as it shows the REAL person and very touching stories.

    Thanks Andrew, you will become the best interviewer ever…

  • http://www.jamesphart.com James P Hart

    I really enjoyed the storytelling theme to this interview. Storytellers always seem more interesting and the ideas are bought to life. Thanks Chris and Andrew.

  • mjohnsonperl

    Awesome interview. Loved hearing from Chris MacAskill as always. I like to keep an eye on Chris and Don's blog to see what is happening at SmugMug and technologies in the industry. I'm anxious to see your interview with Don, and would also like to see another interview with Chris at anytime.

  • dpatru

    Fantastic interview. Great job Andrew!

  • aaroneden

    Wow! That was an amazing interview, great work!

  • Chu Muonelo

    Man, an amazing interview. I'll read whatever book he writes. But I would like to hear more personal stories. Coming from somebody who was in a somewhat similar situation, I can understand why he wouldn't wanna tell. But I'm still curious, to see if there are any similarities.

  • http://mixergy.com Andrew Warner

    I really hope he writes a book to.

    I'd love to do a series of biographical interviews with him too.

    There's so much more that I want to hear.

  • http://mixergy.com Andrew Warner

    I really hope he writes a book to.

    I'd love to do a series of biographical interviews with him too.

    There's so much more that I want to hear.

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