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There are many risks involved in starting a business, and entrepreneurs know that there’s a good chance their ventures will fail. In fact, many entrepreneurs talk about how failure is essential to success. Few in the world have experienced as disproportionate a ratio of successes to failures as Kevin Ryan. Fashionistas know and love his ecommerce brainchild, Gilt Groupe. Those in the ad world know him for his work at DoubleClick. And if you’re well read on business content, you’ve probably clicked through Business Insider. But Ryan also is (or was) the man behind other companies, too, including 10Gen, Music Nation, ShopWiki and Panther Express.

He earned an economics degree and an MBA, did a stint on Wall Street and spent some time at Disney. Ryan realized in the early years of his career that he’d rather be in a small company and have more responsibility than be a cog in the machine of a larger one. With more than two decades of management, entrepreneurship and tech tycoon status under his belt, he jokes that “by now I’m completely unmanageable — I have to be an entrepreneur for the rest of my life because I can’t easily work for anyone.”

Mashable spoke with Ryan about how he manages his three businesses, became a tech leader, and outruns the competition.

Name: Kevin Ryan

Companies: Gilt Groupe, Business Insider, 10gen

Employees: Gilt Groupe – 830, Business Insider – 65, 10gen – 50

Fun Fact: “Don’t laugh, but I play competitive ping pong. We’re setting up a tournament now which I’m going to start training for. I was the DoubleClick ping pong champion for many years.”

Q&A with Kevin Ryan

You’re a serial entrepreneur in the tech arena — what first drew you to tech?

It was somewhat accidental, because I was working for a large media company, E.W. Scripps in 1995 — we sold comics, columns, crossword puzzles to newspapers. We thought, how could we expand our business? I thought, there’s only one newspaper in every town, but there’s a concept called the Internet, and maybe if we put everything on there — which sounds so obvious now — then people everywhere would love Dilbert and Peanuts. So we set up a website, and the Dilbert website, through a little bit of skill and a little bit of luck, became one of the most successful websites in 1995. It was profitable, ad-supported and commerce-enabled, and it was one of the top 10 websites. So in the beginning of 1996, I thought, this thing “the Internet” is going to be one of the most fundamental trends in my lifetime.

I went to the parent company and said, “you should give me a couple million dollars, and I’ll build up an Internet business.” They said “I don’t know, it’s risky, it might cannibalize our current business.” I said, “Forget it, I’m going to go start a company then, because this is really big.” And that’s how I really, full-time got into it. I went out and I was going to start DoubleClick. As part of this process, I came across a company called DoubleClick that had 20 people and had developed a really great piece of technology. And I realized I didn’t know that much about technology as these two engineers who had this dynamic ad-serving thing, and I thought, “Wow that is really important, really cool, I didn’t think of that.” So instead of starting on my own, I decided to join them. And then I became president and then I became CEO. We started with zero people and four years later we had 2,000 in 25 different countries, and we had gone public and made four acquisitions — it was crazy and incredibly fun.

What about your startup ideas — and there have been a few — were game-changing?

You have ideas within the company that end up being very important, and then there’s the idea of a new company. So Gilt has worked really well — we started it four years ago, now we’re up to 800 employees and $500 million revenue — so it’s really taken off, and it’s exciting to see the passion the consumers have for it. I feel really great about Business Insider — we have 12 million [monthly] uniques, and I came up with that idea four years ago — it’s a pure example of execution. Most people think that for startups, you have to have the best idea ever, one brilliant idea. It turns out actually that most entrepreneurs don’t have a brilliant idea.

You’re going to start an ad agency or a restaurant — is the idea that great? If you open a restaurant across the street and it’s great, everyone will go eat there, and you’ll be really successful without a great idea because it’s great execution. Any time I’ve started an idea, including Gilt, if it’s any good at all, there are 20 people doing the same thing. DoubleClick had 37 competitors after a year and a half of being in business. It’s all about doing it really well. In Gilt, we’re not even the first person to launch flash sales — ideeli was there two months before us. Yet we became much bigger and faster because the product is better. 10Gen is the only one that people don’t really know about, and it’s going to be very valuable and game-changing in parts of the technology industry. Tens of thousands of companies have downloaded that database and are using it right now.

In what ways are your companies symbiotic?

They’re not. In the beginning, we started six companies in about three years, and we shared office space. There were about 20 people working for each company, each with its own CEO, and I was the chairman. There were 10 people who did finances for everyone. So they were all independent companies from a financing point of view with different investors, but they shared a back office, which made it much easier. If we started a new company, we’d already have payroll and finances set up. So you would just focus on the actual business — hire the engineers, build the product, focus on the core.

But Gilt got to be very big very quickly. We had six business, and I thought a lot of them wouldn’t work because most companies don’t work. Turns out a lot more of them worked than I had planned. I couldn’t have 12 of these and still play the same role. So two decisions were made: I wouldn’t start any new companies, and I’d focus as much of my time as possible on Gilt. I sold off Panther Express and ShopWiki, went off the board of Music Nation, and I became CEO of Gilt and chairman of [Business Insider and 10Gen]. I spend 90% of my time on Gilt, and I’m an outside board member of the other two, so I spend two hours a week on each of those — hiring senior people, raising money and strategy conversations.

What have you learned from launching all of these businesses?

That there’s still just great opportunity on the Internet in so many different areas. One of the interesting things about my companies is that they’re completely unrelated — super-technical company, ecommerce, consumer company and a media company, not to mention a search function for shopping and technology infrastructure. It’s all about people. Your concept’s not worth that much, but if you can get a great team, then you’ll be successful. So that’s what I do all day long, I hire. I’m interviewing people all day long and retaining, making sure that our good people stay and are in the right spots.

When you’re starting a company, what’s your vision of success?

You start by focusing on the consumer, or the client, if it’s B2B. I don’t think about exits or profits, I think that I need to create a product that people really want. If that works and people are buying it, then over time, each year you spend a little time tweaking the business model, optimizing it. Year two, you think a little about that. It’s not winner takes all, but it’s not far off. Who’s the number two player to eBay, to Amazon, to Google? That’s why I’m always pushing as hard as possible to be that number one player. You get all the PR, which is self-reinforcing. No one writes about number two. People want to work for the leaders — so do vendors and investors. It’s about being there and going really aggressively in the beginning. I always end up raising more money than my competitors, spending more, hiring more people and hiring them faster to make sure that we win.

How do you raise so much money?

There’s no question that it helps when you’re raising money if you have a track record. It’s a safer investment for people — all of these businesses are risky, and they know they’re betting on people. They want to know that you’re someone who can hire and make decisions. And then the rest of it is the team. When I put the team together, I think about that — they’ve gotta be good because that’s the value of the company — you don’t have anything else.

Where is an entrepreneur supposed to find top talent?

In the very beginning, you’re not even using search firms because you don’t have the money to do that. You’re going out and finding people yourself. If an entrepreneur comes to me and says they can’t find a person or can’t convince people to join, I would say, “Unfortuantely, that’s the job.” If a sales person can’t sell, then you can’t be successful. If you can’t convince people to join you, you shouldn’t be doing this because it’s very hard.

Think of all the people you know, the friends you have. Let’s say one of them suggests that you quit your job and join him in a startup. You’d be thinking, “Do I really want to work for this guy?” Think about it: Who would you do that for? You need someone who’s smart, charismatic, successful — a lot is just about that person, and a big part of the skill is inspiring people.

What makes someone a great entrepreneur?

You’re going to have to have a high level of passion, a high level of energy, you need to be pretty smart, because you need people to follow you. Every day people are going to think, do I want to keep working here, or do I want to work somewhere else? Everyone here can work somewhere else like that. They have to feel like what we’re doing is going to be successful, they have to like the environment and think it’s good for them — and a lot of that comes from the top. You need to inspire that feeling among employees.

When you run startup companies, things go wrong every day — that’s what I do all day. You want to be moving really quickly because speed is essential. I find so much about business is really just about judgment. You’re faced with suboptimal choices all the time, and you just have to make a judgment call.

You’re pretty involved in philanthropy — why is that important to you?

You need to be doing what you want to do and like to do, and it has to be a balance. If you want to be a CEO, you can’t spend all of your outside time on philanthropy. I think not only is it a great thing to do, but I find it good to have little breaks for tangential thinking. If you immerse yourself all day long in something, you get too close to it. So once in a while, it’s good to pull yourself out and be around a separate group of people. You come back with a fresh perspective. I always have thoughts for my own businesses coming out of other business meetings or non-profits. And it’s just intellectually interesting. I do think it’s very important, and it’s always nice to feel like I can add value [with my knowledge of the Internet space].

Gilt is your most famous venture — where did the idea come from?

I had seen this business model in Europe. Vente Privee is the biggest one, but it’s not the only one — there were three or four people doing it. It was the first time I saw a concept somewhere else that should be here [in the U.S.]. Usually it goes the other way, and most of the things I’ve launched in the past are just new ideas here. I’m always thinking of new ideas, and I was thinking, “Why would that work there and be doing a billion dollars in revenue, and yet no one’s doing it in the U.S.?” I spent two or three weeks thinking about that — I never do a presentation — but I think about the model, I spend time on the site, I think about economics and what works for the brand, what works for the consumer, what works for the company. And I just concluded that no one had done it, and that it could work here. I threw the idea out to a couple people, and some thought there were structural reasons why it would not work here, saying that France is a different market. And I just thought, “No, I think they’re wrong. I think it’s gonna work.”

Series Supported by Diet Coke®

The Extraordinary Entrepreneurs Series is supported by Diet Coke®. Now, the drink that helps you stay extraordinary brings you extraordinary people. Find Diet Coke® on Facebook for access to a whole lot of extraordinary.

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