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What Keeps Rock Star Entrepreneur Amy Webb Up at Night?

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As part of an ongoing interview series with successful female entrepreneurs, the first features a Q&A with Amy Webb, founder and CEO of Webbmedia Group

Amy, tell us about the Webbmedia Group and why it's so unique?

Webbmedia Group is a very unorthodox consulting firm. In fact, I hesitate to even use the word "consulting," because it really evokes a kind of work that we shy away from. I like to think of us as a team of digital Avengers. Each of the brilliant women and men who works with us offers a different super power (professional game building, behavioral economics, IP law, marketing, anthropology), and we join forces to both solve problems and to think big for our clients, who are some of the world's largest corporations. We focus on emerging technologies and try to understand how consumer behavior is changing. We're constantly evaluating very early stage startups and thinking about the future impact they might make on a community.

What led you to build such a company?

I'd been living in Tokyo and Hong Kong as a reporter, and I remember seeing the first widespread use of smartphones, which hadn't yet made it to America. I fell immediately in love with the technology, but I also recognized how much it would wind up changing consumer culture. When I came back to the U.S., I had a really difficult time fitting back in to a traditional newsroom. I wanted to convert and use audio into mp3s for use on websites, and to make documents I'd used for reporting more interactive online. I always faced a tremendous uphill battle with my editors, and eventually I decided that I'd be happier and more useful outside of a newsroom setting.

Because of my knowledge of code and hands-­on experience with emerging tech (which at the time was much more advanced in Asia) I was often asked for advice and to help others with their projects. My parents and then-boyfriend (now husband) kept urging me to charge for that advice, and one day I finally relented. It started with one very small arts and culture website client, and within the first six months I had three clients on retainer and another handful of projects located all along the East Coast in the works. By the end of that first year, I started recruiting my team. Since then, I've been quietly running a stealth firm that whispers into the ears of executives, helping them learn about the next big changes in digital communications and tech before everyone else has had the chance to figure out what's happening.

As a successful female entrepreneur, what are you most proud of?

I've launched several companies and I also advise a number of startups. Of everything I've done, I'm probably most proud of a project we just finished. Recently, we worked with the City of Chicago to re­‐imagine the library of the future. That body of work included a new organizational chart and new job descriptions, with an emphasis on digital. We also developed ideas and plans for cloud-based library cards, partnerships with local hacker communities, different ways to log and track the digital assets used at the library, and the first‐ever set of benchmarks (more than 80!) that a library can use to measure and prove its effectiveness and benefit to the community. With the blessings of the Chicago Public Library, we turned those benchmarks into a toolkit and distributed it -- for free -- to libraries all over the world. We've received tremendous feedback so far and know that the benchmarks are catalyzing serious change throughout numerous communities. I'm proud of the fact that there's a social good component to everything we do at Webbmedia Group.

What gets you motivated in the morning?

The opportunity to help disrupt something, whether it's a conference or an industry or just a usual train of thought, is what drives and excites me. One entire wall of my office is covered in IdeaPaint, and we use that surface to track not just ideas, but to map out changes that we see coming. So many executives fear those inevitable evolutions. My team is there to get in the sandbox, play around, get really messy and to then develop the winning strategies that ultimately put our clients ahead. We absolutely love it when a client tells us that XYZ is coming, and it's going to kill their industry. Or that they're in some kind of impossible situation, and they need great, big ideas to get themselves righted again. The messier my team can get, and the harder we're forced to think, the better.

What keeps you up at night?

Letting a client -- or anyone, for that matter -- down. We work with a very limited number of companies at a time, in order to immerse ourselves in their challenges. That means being available to them 24 hours a day, seven days a week. I've had a client wake me up in the middle of the night, because he was consumed with worry about a vendor meeting the next day. I made a cup of coffee, went down to my home office, and talked through strategy with him for more than two hours. We'll do everything in our capacity to make sure our clients are always the smartest people in the room, that they're executing on the most creative digital strategies and that they feel empowered to act on great ideas. If I thought for a second that someone we advise wasn't happy with our work, it would absolutely kill me.

I've been criticized before by my male counterparts for having this sort of emotional attachment to my work. And I see countless articles written about how men are more stoic, and are therefore better qualified to work in high-stress situations. I don't buy that at all, not one bit. I think I've been successful precisely because of how competitive I am, and because I express an emotion or two.

Whats next for Webbmedia Group and for Amy?

Since we launched, we've centered a lot of our work around media. This fall, we're expanding our services and client base to include law, publishing, government, health care and retail. With all of the changes we're seeing in social media, mobile, gaming, crowdfunding and digital education, we feel pretty strongly that those are the next industries that will experience significant disruption. In order to manage that incoming client base, we named a new Director of Operations and have brought on a few new Avengers this summer.

As for me, I have a new book coming out. In a way, it fits squarely with what I do every day at work. It's about how I gamed online dating in order to meet my husband. It's called Data, A Love Story, and it's on presale now and launches in bookstores nationwide January 31st.

Tell us something no one knows about your firm, but they should?

We are a completely virtual operation. We've created an internal management system out of Evernote, Google Docs, Dropbox, a few CalDAV accounts and instant message clients, and we operate as a distributed network. That allows my staff to live in cities that are most comfortable for them, and to work hours that accommodate their lifestyles. We have regular meeting times during the day and week, and otherwise everything happens in the virtual environment we developed. We work incredibly hard, but we do it in spaces that are comfortable and convenient.

If you have suggestions for future interview candidates, please ping me at @susanmcp1 on Twitter. Thank you.