Kevin Ryan

AlleyCorp Chairman & CEO

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How Do You Compete With Rivals?

Every company I start is competing against other people, so you want to be studying them all the time. You want to be as objective as possible because there's some reason why they're winning lots…

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What Mistakes Do People Make Over and Over Again?

A lot of our interpersonal skills. I find that as people get more and more senior, the hard skills become a little less important and soft skills become more important. So you know, your reputation…

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How Do You Make Meetings More Effective?

You know, I don't think the goal is necessarily that things go faster, it's that you're there for a purpose. A single question you can ask at the meeting is, you know, "Was this meeting…

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How Do You Deliver Bad News to Your Team?

Bad news should just be delivered as objectively as you can and as quickly as you can, and put in a context, not just, "You're a terrible person." Or, "There's a big a mistake," or,…

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How Do You Fire Someone?

The key in firing someone—assuming it's not for an ethical problem, it just occurred—is that it should not be a surprise to the person. If it is a surprise, you haven't done your job as…

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What’s the Biggest Mistake When Raising Money?

It depends on your choices. The mistake that people sometimes make is choosing money from the wrong people, but that assumes you have a choice. Sometimes you need to get money anywhere you can, and…

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What Is the Most Important Soft Skill for a Manager?

An important soft skill is to, their employees need to feel like the manager wants them to succeed. We've all been in situations in our career where you just thought your boss doesn't like you,…

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How Do You Talk to Someone About Sensitive Topics Like Personal Hygiene?

In general, more honesty is better. You want to be giving feedback to people. You want to give it to them not in front of a big group, but in feedback I've had conversations with…

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What Was the Low Point in Your Career?

So probably the biggest challenge in my career was post-2000 at DoubleClick. We had gone from zero to 2,000 employees in four years. The Internet bubble collapsed, and, over two years, 70% of our clients…

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What Is Your Idea of Work-Life Balance?

Work-life balance is extraordinarily important to me. So, I have three kids, and I have structured my life for the last 20 years, even when I was running a startup, to make sure that I…

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How Do You Find a Needle in a Haystack?

I think you have to start pulling off hay one by one with your pitchfork. You have to spread it out. You have to spread out the hay as much as possible. That's your only…

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What Advice Would You Give a First-Time Manager?

A first-time manager, as I said earlier, just needs to build trust among their employees. They need to set an example, so you want to know that, as an employee, your manager is willing to…

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When Is It Okay to Yell at Someone?

I don't yell at people. I think it's inappropriate to yell at people. People understand that you're upset about something, but I don't see any reason why you have to yell at people. Generally, people have…

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What Do You Do When You Hit a Wall?

You know, I look at business, and I don't take it that personally. You know, for me, most of business is going to be a little bit like, you know, playing sports. You have a…

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Are Entrepreneurs Born or Can They Be Made?

There are many people who are thrust into being an entrepreneur, because they lost their job, because all of a sudden one day they had a great idea, because they were frustrated working for a…

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Was There a Moment You Realized You Made It?

DoubleClick for me was a pretty seminal moment because, you start with this young company. I was 32 in the beginning and then all of a sudden we became a major, major company in the…

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How Do You Deal With Enemies in the Workplace?

When you're chairman, you don't have as much of a problem with enemies in the workplace, because if you have an enemy, you would have them leave the company. So actually that's not a particular…

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What Is the Best Advice You’ve Ever Received?

Tom Murphy was on the board of DoubleClick, and Warren Buffet called Tom Murphy probably the best manager in the United States. And at one point, I was explaining a very difficult, thorny situation in…

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What Is Your Must-Ask Job Interview Question?

Sometimes I'll ask them, what were they like in high school? What did they like to do? I want to know just who they think of themselves being in high school. And also high school,…

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How Do You Conduct Performance Reviews?

The most important thing in a performance review is...what I start with always is, "We're gonna sit down and review your performance in the last six months, and you're gonna realize that we've already talked…

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What’s Your Biggest Career Mistake?

I think early on, I didn't take enough risk, actually. I didn't start my first company until I was in my late 30s. I had joined an internet company when I was 32, but in…

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How Do You Come up With Your Best Ideas?

I come up with the best ideas really [from] talking to other people. Most ideas are tangential, where you're thinking, "Oh, there's a trend happening in this market." But actually you think in your mind…

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How Do You Give Critical Feedback?

Giving critical feedback, the important thing is to do it one on one and to set the context as much as possible because it's always going to be hard for most people to hear. I…

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What Is Your Biggest Time-Saving Trick?

I don't think there's any one trick. I think that you are always trying to think as a manager, "What am I doing that I need to do?" Because most of what you're doing the…

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"Named Entrepreneur of the Year by Ernst & Young in 2009"

Kevin Ryan is a technology innovator and entrepreneur who is perhaps best known as the former CEO of DoubleClick. Kevin spent 9 years as President and then CEO building the interactive ad giant into a multi-billion dollar global industry leader, which was ultimately acquired by Google in March 2008 for $3.1 billion.

Kevin is chairman and chief executive officer of AlleyCorp LLC, an incubator of technology and Internet companies based in New York's Silicon Alley. As part of this role, Kevin serves as chairman of the juggernaut fashion site Gilt Groupe, as well as of Henry Blodget's Business Insider. Kevin is also co-founder of the other companies in the AlleyCorp network, including MongoDB, a scalable and manageable data persistence platform for cloud computing.

Aside from his professional responsibilities, Kevin serves on the boards of Human Rights Watch, the NYC Investment Fund and INSEAD. Kevin is also a member of the Council on Foreign Relations and the Yale International Council. He was the first angel investor in TheLadders.com and previously served on the boards of the Direct Marketing Association, The Ad Council, HotJobs and the advisory board of Doctors Without Borders. Kevin received a B.A. from Yale University and an M.B.A. from INSEAD (The Business School for the World).