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Seven Questions with Kate Ryder

Classic advice for founders from the Sequoia community.

Kate Ryder is founder and CEO of Maven, a virtual clinic dedicated to healthcare for women and families. She is also a card shark—she’s played bridge regularly since childhood and once surprised colleagues at her previous job by winning the company poker tournament.

What advice should first-time founders heed?

I think the number one quality every entrepreneur needs is persistence—and to be persistent, you have to truly believe in what you’re doing. Founding a company is a very long journey, and conviction is what will carry you through the ups and downs. Maven is a good example, because when we started, women’s and family health really wasn’t a market yet in venture capital. No one had a thesis on the industry the way they do today. So fundraising was difficult in those early days, and it was the patient stories that kept me going. I remember one day in particular, right after we launched. I’d just been rejected by an investor, but then I got a text from a user I’d met. She was 18, she’d just moved to New York and didn’t know anyone, and she’d been able to get a birth control prescription through Maven. She was so grateful and had told a bunch of her friends about us, too. I forwarded her text to the team and said, “Our product is making a difference.”

What question are you asked more than any other?

Both of my kids were born while Maven was scaling, so I’m often asked some version of, “How do you do it all?” My response depends on the situation; I do think it’s interesting that my husband never gets a question like that, even though he’s changed as many diapers as I have. If I’m the only woman on a panel, and all the men are being asked about their companies while I’m asked how I balance motherhood with being a founder, I usually say something like, “Not gracefully!” and change the subject back to business.

But when I’m getting to know someone one-on-one, I’m happy to talk about it—and to hear how they do it all, too, because we can learn from each other. One thing I’ll tell them is I don’t blur the line between work and the rest of life they way I did before I had kids. I may work until 1 a.m. after the kids are in bed, but from 6:30 to 8:30 p.m. and on weekends, I’m with my family. The other key for me is that age-old cliché, “it takes a village.” My husband and I are very lucky to have an amazing nanny and family and friends who are around a lot to help. We’re all a team.

What experience shaped who you are?

I spent the early years of my career as a journalist, and that’s shaped so much of how I operate today. Back then, I needed a great network of sources to help me tell stories. Now I need them to help me make good decisions. I’m never shy about picking up the phone to ask for some expert advice.

In general, I think there are lots of parallels between reporting and building a company, especially if you’re creating a category. A journalist starts out not having any idea what the story is about—then just when you think you’ve got it, you talk to someone else and that changes the arc completely. You’re problem-solving; you’re creating structure from chaos. That’s true as a founder, as well.

What’s the best interview question in your toolbox?

Once a candidate has spent some time with me and the team and has a good idea of what the job will be, I like to ask them what they think the three most important qualities are for the person who fills the role—and to rank themselves on those qualities. I definitely have my own three in mind, but hearing people’s answers also helps me define the role. There is such a thing as a wrong answer; if it’s an operations role, they shouldn’t talk all about sales. But there can be more than one right answer. It’s interesting to hear how different candidates describe the same basic qualities, too. If one person talks about process improvement and another says “KPI frameworks,” that tells you something about how each of them thinks.

The ranking is important for a couple of reasons. For a leadership role, they usually do need to be relatively strong in each area. If the position is all about data and analytics, that can’t be what they’re worst at. But it also tells me how self-aware they are of their own strengths and weaknesses—intellectual honesty is one of the most important traits in any executive.

What book should every company-builder read?

There are so many! I’m always recommending books to people. One good one is The Cluetrain Manifesto, by David Weinberger. It’s basically about how the internet and the markets are just a series of conversations. When I was changing careers from journalism to tech, it helped me understand how to shape a narrative and think about messaging—and how to find the signal in the noise.

I often recommend essays, too. I had a team member who was great, but she was struggling with confidence, so I sent her Joan Didion’s On Self-Respect. Another one I share a lot is This is Water, David Foster Wallace’s commencement speech at Kenyon College. It’s such a good reminder to walk in someone else’s shoes and that things aren’t always as they seem. Empathy is important when you’re growing a team—and I think it’s something American culture in general is struggling with right now.

What’s a lesson you learned the hard way?

I’ve learned not to be over-prescriptive when I’m giving feedback. As a founder, sometimes it’s your job to know exactly how something should be. But there are other times, especially on the creative side of the business, where you should give more room for exploration. In the early days of Maven, we had a lot of freelance designers, and I had to be much more specific. Now that we have amazing designers in-house, my job has shifted more to setting the broader vision and letting them design the product. They have lots of great ideas of their own.

Of course, we do need to balance a product and design culture with moving quickly and getting things out the door. But even when you’re on a tight timeline, you can offer more nuanced feedback and give someone the opportunity to take it from there while still saying, “but we need to start on Friday.”

What invention do you hope to see in your lifetime?

I don’t know what kind of invention it would be—maybe a public policy, a new form of government, even a biotech advancement—but I’d love to see something that promotes our most benevolent and charitable impulses and curbs the worst ones. When you read a book like Sapiens, you realize how both of those extremes have shaped human history. And the internet sometimes doesn’t seem to be pushing us in the right direction. People get entrenched in what they think and forget to take a moment to understand the “why” of someone else’s experience or point of view.

There’s also a lot of good in humanity, and there are a million examples of people trying to embrace that already. But if there were some sort of mic-drop invention that solved the problem, a machine where people could just go in, push a button and come out ready to promote more of the good, that would be amazing.