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Sky Dayton

Sky Dayton, 38, has had something of an accelerated life. Voted “most likely to succeed” in his fourth-grade class, Dayton began making good on that promise early by graduating from high school at 16; running the digital imaging department at two ad agencies by 18; and, one year later, starting his first business, a coffee shop on Melrose Avenue frequented by Quentin Tarantino and featured on MTV. He was far from done. He formed a computer graphics company specializing in advertising and design at 21. But all that paled in comparison to his next success, when he founded Internet service provider Earthlink in 1994 at 23. Earthlink grew into one of the largest dial-up providers in the world during the 1990s, though it has since seen its customer base shrink in the age of broadband. In 1999, Dayton stepped down to nonexecutive chairman at Earthlink; he left the board of directors in 2008. Since then, he has focused on being an ideas man, co-founding incubator and venture capital fund eCompanies and founding Wi-Fi provider Boingo Wireless, while still having time to surf and take his kids snowboarding. At ease and in good spirits in Boingo’s Westwood headquarters, Dayton, sporting a long-sleeve shirt and laceless Chucks, talked with the Business Journal about Thomas Edison, the aesthetics of business and the influence of Scientology on his life.

Question: What are you doing with your time these days?

Answer: Well, right now I help Boingo however I can, but this is an amazing management team here. Dave Hagan, the CEO, is just world class. It’s kind of a principle I have of start something and then work myself out of a job. (Laughs). I have been doing a lot of investing, mainly in public companies, so I spend time these days looking at a lot of different ideas on the investment side. On the entrepreneurial side, I’m incubating some ideas. But I can’t really talk about the stuff I’m working on.

They are Internet-related ideas, though?

Yeah. (Laughs).

Why do you like the idea of starting businesses so much?

This idea of bringing life to something that didn’t exist before. To take something that’s already at one and make it 100 is 100x. That’s big, right? But to take something from zero and make it one is infinite. There’s infinite value creation, to take something that did not exist and make it one. And that’s in many ways the hardest thing to do.

Do you consider what you do creative or artistic, then?

It’s sort of this idea of aesthetics, which can take on many forms. You can think about aesthetics purely in the field of the arts or fashion or film or music, etc. But you can also apply that idea to any pursuit. And it really to me means you care about how things look and feel; you care about what the message is; you care about all the details. And I think that’s kind of an X factor that is a difference between good and great in anything. An artist thinks about how the audience is going to receive the communication, and they’re able to assume the viewpoint of the audience. I think that’s something in business that is really a key to success.

What are things that are aesthetically beautiful about a business, then?

Wow. (Laughs). That’s pretty philosophical. Take Earthlink, for example, OK? The logo ties in with the customer care experience, ties in with the experience that you have when you connect to the network, ties in with the way it’s priced, ties in with the way it’s marketed, you know. It all like flows and works together. And the magic of that arrangement is what made us supersuccessful. I think other entrepreneurs that went into the Internet providing business thought about one of those things. They thought, “Oh, I just gotta price it right, as low as possible.” But they didn’t think about customer care, they didn’t think about how easy is it to connect.

So it’s about having a vision for how everything works together?

You’re gonna have fun editing this story. Howard Schultz at Starbucks said everything is important. And it’s true some things are a little more important than others, but everything is important. It’s down to how your product feels when you pick it up, the tactile feeling of it, the smell of it, the sound it makes, you know? So anyway, all those things are aesthetic. And I think that’s something I try to bring to any business I’m involved with.

It’s interesting you mention Starbucks, seeing that you were a coffee shop owner.

You know, I told Howard Schultz this: Earthlink was the Starbucks of Internet providers. You take something, you do really great customer care, you really care about the experience and you scale it as rapidly as possible. And that was the Earthlink model, but it took me a while to learn that.

Is it just the act of starting a business you enjoy or is there something about what kind of business it is?

Well, I’ve always been fascinated with communication. I guess if you were to try to distill a common denominator, whether it be art when I was a kid or working at an advertising agency, or a coffee house where we had poetry readings and salons and concerts and things like that to the Internet itself, I’m passionate about communication and enabling people to communicate. So I guess that means it’s harder for me to get as excited about businesses that don’t involve that.

Not everyone’s like that.

Yeah, some people are passionate about business just for business. I think that can make an amazing entrepreneur as well. You have people that can have a local TV affiliate and a concrete mixing company. They can have a plumbing supplies business and own a soccer team, and they just love it, they just love the business, right? I love business, but I really love communication.

Why?

I think that’s to me the most powerful thing that we do as humans. In many ways it’s what defines us. So that’s what’s so amazing about the Internet. It’s the greatest communication medium ever invented. You can go back in history and each major advance, each major turning point in civilization involves or was spurred on by an advance in communication technology. The earliest invention of language, the invention of the printing press, the invention of the telephone and radio that ushered in the information age that we’re in now, and the Internet age really began in the last 15 to 20 years.

What Internet trends excite you?

We have four or five things that are multipliers of each other. One is the number of people that are on the Internet. We’re not there yet, having everybody, but ultimately it will be more than everybody on the Internet. You’re going to have more than one Internet connection – you already do today. So billions, tens of billions of connections, of connected devices. The incredible increasing power of those devices. And finally, mobility, the fact that we now have the Internet in the air that we breathe. So all those add up to an incredible platform for innovation and for new types of devices and services.

Where do you see it going?

I’ve said this consistently for 16 years: It’s like trying to predict the uses for electricity at the time that electricity was invented. I mean electricity’s been around, but when it was harnessed, if you sat down with Edison and said, “Hey, what are all the things that people are gonna do with electricity?” well, I don’t think he would have told you about the smoothie machine, you know? Or the electric car. Or the MRI machine. These things both sort of prosaic and incredible, that was left to the entrepreneurs that followed the invention of the basic platform.

Maybe not the smoothie machine, but you could have asked what people might be using electricity for in, say, five years.

Yeah, he’d probably say the light bulbs and heating and stoves, you know, some basic things.

So…

So you want to know what the light bulb equivalent is? (Laughs). Social networking is just getting started. Marrying that with location-based services, that’s just getting going. We haven’t reached a point yet where, here’s a very simple thing: You’re at a movie theater and a dear friend is three rows back and you don’t know it. And the privacy and everything you would have totally allowed: I want that guy to know that I’m here. That’s like my best friend, you know what I mean? And we haven’t cracked the code on that – so, duh, right? (Laughs.) All the pieces are there, right? We haven’t done that yet. That’s just one.

I understand you didn’t go to college. Why not?

I applied to CalArts. That was the only college I applied to and I didn’t get in.

Why CalArts?

I was interested in animation at the time. I had done an apprenticeship in high school in a special effects house.

Animation?

My parents are both artists. I grew up with art, and I was in an environment that really encouraged artistic pursuits. I just loved the idea of taking something that was static and bringing it to life.

Instead of college, you worked at two ad agencies, opened a coffee shop, and started a computer graphics company, all within a few years.

I was in the mode of try a lot of things. I think a lot of kids today maybe get worried about, like, “I picked that thing, and I’m gonna get that job and I’m gonna be in that job for 15 years.” Doesn’t mean you should just hop around – you should show some commitment, some loyalty – but at the same time, there’s so much choice. There’s so much just amazing opportunity in the world. And so, try stuff. Throw stuff against the wall and see what sticks.

Maybe college isn’t all that it’s cracked up to be?

I think for a lot of people it’s absolutely the right move, it’s just a question of going with a purpose. What are you going to accomplish when you’re there?

As for your formal education, you graduated from the Delphian School in Oregon when you were 16. I’ve read that Delphian School is connected with L. Ron Hubbard. Is it a Scientologist school the way that some schools are Catholic schools?

No, it’s not a religious school. It uses the study method that was developed by L. Ron Hubbard. Some of the kids who go there are Scientologists and to my knowledge most are not, but that’s sort of neither here nor there. I got an amazing education there. Really the first thing about the study method is that you learn how to learn.

How so?

One example is ensuring you have a balance between the theory of what you’re learning and the practical application of it. So, for example, if you’re studying how to fly an airplane, you would read a certain amount, you would get to a certain point, but then you really need to get into an airplane. You need to get that balance.

What’s an example of how that worked at your school?

A great one would be the apprenticeship we talked about at the very beginning. I was studying animation, I was studying special effects, and then they said, well, let’s get you an apprenticeship. Let’s get you out actually working in the field of your study, of your interest. So from a young age I was able to see how what I was learning was applicable, and not just the learning that was directly related to the apprenticeship, but everything else I was studying.

How did you manage to graduate at 16?

It uses the English form system instead of grades. Are you familiar with forms? They have that in England; basically, form eight is like 12th grade. Each student can take courses and progress at their own speed, and so I did these courses a lot faster than other kids, so that’s why instead of graduating when I was 18, I graduated when I was 16.

In other interviews I’ve read, you didn’t want to talk about Scientology. Is it something you want to talk about today?

I’m happy to talk about it. I think it’s something that’s been tremendously helpful for me and my family. I think if somebody wants to learn more about it they should buy a book or check it out.

You would consider yourself and your family practicing Scientologists?

Sure. Both my parents were Scientologists.

What about it has been helpful to you?

It’s really helped me to not accumulate baggage as I’ve gone through life. You have different experiences and some of them are good and some of them are bad. And I think that bad experiences tend to kind of stick to you. And so you find people that later in life, you feel sort of weighed down. And it’s helped me to just not have that baggage.

Is that one of the principles, that you don’t let things accumulate?

One of the principles is that you address them and that you’re going to experience things in life and they may not be that pleasant, and you are able to address those so that they don’t impact you and you’re able to keep your original goals and purposes and your drive towards them really fresh.

How does your family fit in all this?

I love doing stuff with my kids. I play basketball, but I’m not very good to be completely honest. I’m a good skiier and snowboarder. I can do that. That’s a great family activity. We live in a great place because we’re so close to the water and the mountains.

I understand you are a huge surfer. Where have you surfed?

I love surfing. Surfed all over the world. Probably going back to Indonesia in the late summer for a couple of weeks. I’ve surfed in Hawaii, I’ve surfed in Fiji, I’ve surfed in Mexico and right here at home. Surfing is great.

What is your favorite surfing memory?

I don’t have a favorite one, but the first wave where I really felt the power of a bigger wave was up in Ventura, and it was maybe a 10-foot face, something like that. And I remember being on this wave and feeling it under me and being like, wow, there is so much power here, and just being able to ride that is incredible. You think about a wave, right, it’s actually, the water’s not moving. It’s actually a wave form. Did you study physics or anything in school?

Only in high school.

Alright well it means literally a wave of energy, of just potential. So it’s this potential that’s moving and it’s causing the water to go up and down. What happens is as that wave gets closer to the shore, it actually runs into the bottom as it’s getting shallower, and it starts to back up on itself until it’s got nowhere to go but up. And that’s why these waves, they hit the shore, they come up, it pushes the water up, and it sort of topples on itself. When you are riding it you are riding this pure energy. Where else can you do that? What other sport do you get to do that?

Sky Dayton

TITLE: Founder and Chairman

COMPANY: Boingo Wireless Inc.

BORN: 1971; New York

EDUCATION: High school diploma from Delphian School in Sheridan, Ore.

CAREER TURNING POINT: Taking Earthlink public in 1997

MOST INFLUENTIAL PEOPLE: Garry Betty, former Earthlink CEO, who taught him how to read a financial statement

PERSONAL: Lives in Brentwood with wife, science-fiction writer Arwen Dayton; two daughters, ages 4 and 8; and a son, 9

ACTIVITY: Surfing, snowboarding, skiing, Texas hold ’em

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