The Ladder periodically takes a break from solving readers’ workplace problems to ask successful people about career advice: good advice they’ve gotten, bad advice they’ve gotten, advice they’d give their younger selves, and more. This week, I talked to Dave Gilboa, the co-founder and co-CEO of the eyewear company Warby Parker. Gilboa helped launch Warby Parker in 2010, when he was finishing his MBA at the University of Pennsylvania’s Wharton School. Last year, investors valued the company at $1.2 billion.
Anderson: Did you get any advice when you were growing up that stuck with you over the years?
Gilboa: Both my parents are doctors, and my older sister is a nurse practitioner, and my family instilled the idea in me from an early age that your profession shouldn’t just be an opportunity to earn a paycheck, but you should use that time to help make the world better. I thought, growing up, that I would become a doctor. I ended up diverging from that path, but always kept that advice in my mind as I was thinking about what I should do as a profession and career.
What advice do you wish you’d been given when you graduated from college?
Our education system gets young people to believe that they need more education or experience before they’re able to take on the career and the job that they actually want to be doing: taking an entry-level job, working there for two years so you can get yourself in the door at another job, so you can work there for two years, that allows you to go to business school for two years, so that you can take another job for a couple years … I’ve come to realize that at no point are you fully prepared. At some point you just have to take a risk. I started Warby Parker after having a couple of jobs out of college and business school. I probably could’ve taken that leap a little earlier in my career. I would try to encourage a younger version of me to have more confidence and understand that you can figure things out as you go along. You don’t have to have every box checked before you take that leap.
What is the worst advice that you’ve ever gotten?
I’ve gotten a lot of bad advice. Something that we heard from a lot of people as we were talking about the idea that developed into Warby Parker was, “If this was such a good idea, someone would’ve done it.” There’s a natural tendency for people to look for reasons why something won’t work. But it takes courage and belief in yourself to blaze a path that doesn’t exist. You need to ignore those naysayers, and understand that most people are pretty risk-averse and are going to find opportunities to poke holes in something. I’m glad we didn’t listen to all those people in the early days.
You seem like an amazingly productive person. What’s the first thing that you do when you get to your desk every morning?
I usually don’t have time to sit down at my desk. My calendar is pretty full, and I’m kind of running from meeting to meeting. One thing that I do: I can spend 24 hours a day just responding to email, so I try to limit how much time I’m looking at my email—recognizing that every email I send out is just another opportunity for an email to come back. I view my inbox as a to-do list that anyone from the outside world can put items on, and just responding to that to-do list is not a strategic, efficient use of time.
At this point my day is generally back-to-back meetings, but I try to reserve at least 90 minutes a day for just “Dave time”: an opportunity to think, to reflect, to review materials before going to meetings, to walk around the office, talk with the team, get the pulse of what’s going on in the company.
And at the end of each week I try to look at my calendar and review all the meetings that I had that week and rate them zero, one, or two. Zero means it was a really bad use of time and, if I had to do it again, I wouldn’t have attended that meeting at all. Two is a great use of time—I wanna spend more of my time in those types of meetings. And one is somewhere in-between. And then I’ll connect with my assistant and make sure she understands which of those meetings I want more of and which ones could be filtered out so that hopefully over time my schedule becomes more and more productive.
What did you do with your 90 minutes of Dave time today?
Today I just reviewed a bunch of materials that leaders from different departments had sent me. It was an opportunity to reflect and catch up on what’s going on in the business and give feedback to some different departments.
One of the pieces of advice you and Warby Parker co-founder Neil Blumenthal gave in your commencement address at the Wharton School last year was “Always be tired.” How do you balance being tired in a healthy way without crossing the line into burnout?
We said that a bit tongue-in-cheek, but the advice we wanted to give to graduates was, you should be working on things that challenge you and excite you and things that you have to force yourself to stop doing to go to sleep at night—because that’s the only way that you can have a massive impact. That said, I definitely do try to balance that out more than we did in the early days—whether that’s finding time to exercise or meditate, to recharge and ensure that even though the goal of each day is not to be so tired that you wake up not able to function but to feel that the day has been fulfilling and just tiring enough that you lay there and immediately fall asleep and feel like you had a superproductive day.
Warby Parker was one of the first e-commerce sites that disrupted traditional retail models by cutting out the middleman. What did you learn about manufacturing that some of your imitators could learn from?
Manufacturing is really hard. Right now every company operates with a global supply chain, and coordinating partners from all over the world to meet schedules and quality standards can be really challenging. And ensuring that the partners around the world are operating along the same values—how they treat their employees, how they treat the environment—is critically important. A lot of companies use a sourcing agent, but we build direct partnerships, negotiate deals with manufacturers, raw material suppliers. … We’ve taken a very hands-on approach, to ensure that we’re getting the best quality, and that we’re working with partners whose values are aligned with ours. Those are things that are important to our employees and our customers. That requires a lot of hand-holding, a lot of flying all over the world, but we think that that’s worth it.
This interview has been edited and condensed for clarity.
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