All Articles Leadership Careers Q-and-A with entrepreneur, author and Webbmedia Group CEO Amy Webb

Q-and-A with entrepreneur, author and Webbmedia Group CEO Amy Webb

8 min read


Amy Webb is CEO and founder of the digital strategy agency Webbmedia Group, a co-founder of 501(c)(3) Spark Camp, a lecturer at Columbia University Sulzberger Program and a board member and adviser to various organizations. She also wrote the memoir “Data, A Love Story,” published this year. I recently asked her about being an entrepreneur and about her various endeavors.

You’re CEO of a company, a co-founder of Spark Camp and this year published a memoir that, in part, is a telling of your online dating life. At this point, it’s obvious you’re able to take risks, try new things and put yourself out there, but was it always that way? How different was your mindset before founding Webbmedia Group than it would be, say, for founding a company now?

I’ve always been a risk taker, but I’d argue that my risks are now very calculated. I try to determine likely costs and outcomes and compare those to expectations, whether they’re mine or a partner’s. I incubate new projects all the time. Some become companies, some don’t. The biggest risk, I think, is in not exploring a fresh idea and giving it a little space to see what might sprout.

In that vein, mistakes are inevitable when starting a business. Are there any that particularly taught lessons that have stayed with you?

One thing that I’d do today that I didn’t initially with Webbmedia Group would be to ask many more questions and to see everyone as potential collaborator rather than as a competitor. I see a lot of bright founders miss great opportunities simply because they were too embarrassed to ask for clarification.

Recently, I was sitting in a meeting with a startup CEO and a large publisher.The publisher said “well, you know so-and-so and how they built such-and-such…” I could see it on the startup CEO’s face – he had no idea what the publisher was talking about. So he just nodded and responded “of course.” The publisher finished her sentence and then they went on to another topic.

The thing is that the person the publisher was referencing would have been a dynamite connection for the startup CEO — in fact, I’d bet that it would have meant a substantial new contract. If the startup CEO had just said “you know, I recognize the name, but I don’t know much about her. Can you tell me more?” that would have given the publisher an opening to talk, and then the startup CEO an opportunity to say “wow – would you be able to introduce me to her, because I think we could offer them a solution to that problem?”

There’s a big difference between confidence and hubris. It’s easier to be flashy and act cocky. It’s a lot harder to find quiet inner confidence and to be comfortable asking people for help, or admitting when you don’t know something. This is something that I (fortunately, I’d argue) learned the hard way. I operated in hubris mode until I was in my early 30s. I’m now extremely comfortable asking all those questions, being openly curious and inquisitive, asking for connections and help when I need it. I’m much more open and inclusive in my late 30s than I ever have been before.

Your work includes serving on boards and other advisory roles. For leaders looking to serve such a role, what advice do you have for getting started? Anything that you’ve found that especially works (or doesn’t)?

Board work can be very rewarding. Every industry has professional associations, and that’s a terrific way to get started. It’s usually best to start as a volunteer, helping to coordinate a conference, for example. If it’s a professional board that is elected by membership, it’s a bad idea to join the group and run immediately without having put in any time to the organization. Not only will members probably not want to vote for someone that new, you don’t know what you’re getting yourself into — the board could wind up taking too much of your time or be outside your area of expertise.

It’s also a good idea to try and marry your professional skills to your outside interests. For example, I’m thrilled to serve on the board of the Baltimore Symphony Orchestra. I’m able to advise them on digital strategy and brand outreach, but as a clarinetist, I’m deeply interested in helping to ensure the legacy of this world-class group. I have a strong emotional attachment to the BSO, which means that I’m highly motivated to do whatever I can to help it succeed. When both the board and the member have equal amounts to gain from each other, that’s a good match.

Spark Camp, as the site says, “is a weekend of intimate conversations, idea development and problem-solving, with a focus on a specific theme involving the future of media.” How does this format fuel ideas and, additionally, enable the implementation of those ideas?

We’ve spent the past three years creating a format that brings together smart people from varied backgrounds. We’ve actually just released a manifesto of sorts, which is free and available to download. Our process involves significant curation of attendees, thinking in terms of discreet events throughout the weekend and fostering highly intimate conversations.

As we explain in our report, the more varied the group, the more valuable the connections and outcome. For us, having a diverse group of attendees is about hosting a better event. When people bring together a true variety of backgrounds and experiences, they also bring a variety of ways to frame issues, find opportunities and identify solutions. Our mix of Campers was once perfectly described as “Everyone I never knew I always wanted to meet.”

Before we decide on our individual invitees, we create what we call an “attendee matrix,” which describes our desired composition of the group, their industries, experience levels and backgrounds. More than 50 percent of the attendees at every Spark Camp we’ve hosted have been women. Roughly a third are people of color. Campers have been associated with a vast range of institutions and companies, from large news organizations to scrappy tech upstarts. Some are individual achievers — playwrights, poets or project managers.

Some approaches to further increase each camp’s diversity have been unsuccessful. At our first two Spark Camps, we asked attendees to suggest a “+1.” We thought this approach would necessarily introduce us to new people, and help organizers break out of their own professional networks. Instead, Campers tended to invite friends or former colleagues. People often doubled themselves demographically. For example, white men almost always invited other white men.

We also found that attrition almost always comes disproportionately from groups that are underrepresented at media events. So we plan for it, and adjust our invitee list accordingly. As we’ve said, finding great guests takes a lot of work. Assembling a diverse group of great guests takes more than double that work — and it’s well worth it.

We value discussion over presentation. When event organizers put a speaker in front of a podium, they presume that the speaker has access to a unique and timely body of insight that the rest of the crowd is there to hear. The presentation model is valued for its efficiency — it allows a single person to dispense their latest learnings to an unlimited number of people in an hour or less.

But because we put so much work into bringing together people with unique perspectives, we find discussions to be a much better fit than presentations. We’re not gathering to merely trade conventional wisdom or share best practices. The value of having all the different voices around the table is that it affords a better, stronger platform to debate, discuss and build on each other’s assessments, to enable conversations we can’t (and don’t) easily have online and in public. And so at Spark Camp, we set only a schedule in advance, not the session topics. Instead, we carefully help the participants form their own sessions collectively using a convening framework that we developed.

We value intimacy over publicity. We’ve learned that there’s a trade-off between in-person sharing and social buzz — the more publicly attendees share what they learn during an event, the less inclined they are to disclose valuable pieces of private knowledge. We want attendees to feel safe discussing failures as well as successes, to talk in real detail about processes and outcomes in their work.

At the start of each Spark Camp we ask attendees to consider what they hear as protected by ‘FrieNDA’ (an informal non-disclosure agreement we discovered at NewsFoo, a convening put on by O’Reilly Media, Google and the Knight Foundation). The FrieNDA equates to a social pact — the understanding that conversations are meant to be private. We also ask attendees to shut off their devices and focus on the conversations at hand. Instead of a trail of tweets, we ask Campers to write down flashes of insight on cards and post them in a prominent place during the event. There are certainly drawbacks to this approach. We miss the rich online buzz that builds around events that are fully on-the-record. And it reinforces a perception of exclusivity we’re not trying to foster.

But because of this policy, numerous attendees have told us that they gleaned unique insight and understanding from Spark Camp, knowledge that likely wouldn’t be shared if everything were public.