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10 Visionary Leadership Tips from Warby Parker's Dave Gilboa

What he's learned in the 10 years spent building the direct-to-consumer giant now worth $3 billion.

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Thanks to a new series Comparably has in partnership with Entrepreneur, "If I Knew Then: Leadership Lessons," I have the regular privilege of hosting virtual fireside chats with high-profile CEOs of major brands like Indeed, Blue Apron, Waze and the Dallas Mavericks. During these sit-downs, I ask these incredible leaders to open up about some of the invaluable lessons they learned as they climbed the ladder of success, as well as to offer some practical career advice they might give to other entrepreneurs.

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Recently, for the sixth episode in the series, I had a great conversation with Dave Gilboa, co-founder and co-CEO – along with Neil Blumenthal – of the hugely successful eyewear lifestyle brand Warby Parker. Gilboa and the other co-founders had their brilliant idea in 2009 while still in business school at Wharton, to respond to a genuine need in the market to fix the expensive, needlessly complicated process of finding the right pair of prescription glasses without breaking the bank. Although buying other products online had been normalized at the time, eyewear was still a new frontier.

Flash-forward to 2020, and Warby Parker is the leader in bringing U.S. consumers luxury eyewear at an inexpensive price point, with a successful online business and 120 brick and mortar locations, not to mention a new line of contact lenses called Scout. The company has also done good work, supplying over seven million pairs of glasses for those in need with its "Buy a Pair, Give a Pair" program. From seeing a need in the marketplace to building one of the best and most trusted direct-to-consumer businesses – that's the kind of success any student of entrepreneurship would love to hear about directly from the source.

Related: 5 Tips to Scale a Successful Direct-to-Consumer Brand in 2020

In fact, Gilboa's origin story as co-founder and co-CEO of an eyewear company is perfect in its own right: During a college backpacking trip around the world, he had the misfortune of losing his eyeglasses. Upon returning to the states, he wanted to buy a new phone and needed to get a new pair of glasses: "The iPhone 3G had just hit, so I went to the Apple Store and bought this magical device for $200 that did all these things I couldn't imagine were possible a few years earlier," Gilboa told me. "And then I was going to have to pay $700 for a new pair of eyeglasses, and that's a technology that's been around for 800 years."

Related: How Entrepreneurs with Social Vision Secured Venture Capital

Gilboa knew that something had to be done to fix this problem and discovered others who felt the same way (his three business school classmates who became his co-founders). Little did these entrepreneurs know that they would transform the market forever. Even as the game-changing startup scaled, Gilboa's mission to help make the world a better place never changed. Here are 10 essential highlights from my chat with this incredible leader:

1. Don't underestimate the value of people management

While in business school, Gilboa says he was able to test out of having to take a few management classes in the name of freeing up electives, but he now realizes these skipped classes were among the most important when it comes to running a business in the real world.

2. The co-founders you start a company with should be aligned with you in terms of values and visions

The early core founders need to be a close bunch of like-minded dreamers who believe in each other deeply. "When people told us reasons why Warby Parker wouldn't work, we had enough confidence in each other to bounce back from demoralizing feedback," Gilboa says.

3. In order to inspire customers to change their long-time habits, it's important to offer something dramatically different

Warby Parker's co-founders knew most consumers had never even considered buying eyeglasses online before. Gilboa and his cohorts had to offer dramatically better value and a notably improved experience.

4. Start doing 360-degree reviews with key team members before the company is even off the ground, and stick with them as you scale

Prior to Warby Parker opening for online business, Gilboa and his team were doing monthly 360-degree reviews: open and honest conversations designed to figure out where improvements need to be made.

5. Once your startup has reached a workforce of a few dozen or more people, settle on a set of company values that truly represents the team

At about 20 people, everyone at Warby Parker was asked to volunteer some values they believed in that might potentially make the company creed. From a pool of 200 suggestions, and after much discussion, the business' core values were determined.

6. It's impossible to attend every single meeting as you grow, so prioritize

Many startup founders feel compelled to remain part of everything that happens at a company, and Gilboa says the inflection point for him was when the company hit about 200 employees. He had no choice but to make hard and fast rules for himself regarding which meetings he needed to attend and which ones he didn't. Remember, if scaling is successful, you'll eventually have people working for you that are the best at what they do. Trust them to handle it.

7. The three most important parts about being a leader, according to Gilboa:

  • Set and hold the vision, and make sure never to lose sight of the big picture.
  • Establish clear priorities. This will help settle many conflicts.
  • Harvest continual feedback. This is the only way teams improve over time.

8. You have to take great risks early in your career.

Early on, even failures will still be massive learning opportunities that will set you up for success down the road. Gilboa reminds us that "any safer options are always going to be there" and can be taken advantage of later if need be.

9. Don't be afraid to adjust your core values.

Warby Parker's core values are its Constitution, and that means it's open to the occasional necessary adjustment. The company's Golden Rule was initially, "Treat others as you wish to be treated yourselves," but has been changed to "Treat others as they want to be treated." Gilboa says, "It's small, but I think it's a pretty powerful change that's built on empathy."

10. A co-CEO structure is not for everyone, but it can work if you prioritize what's really important.

Most leaders would scoff at sharing the reins, but Gilboa and Blumenthal prove it's possible to do it successfully. Because Warby Parker was started by a small group of friends who were equally passionate about the brand they were building, they pledged two things to one another: One, friendship would always take precedence before the business, and two, they would constantly revisit the co-CEO roles to make sure it still made sense. The fact that they've led the company together over 10 years later is a strong testament to their admirable and ego-less partnership. It's important to note that the other two co-founders also remain present in their lives and on the board today.

Watch the full webinar to hear the compelling story of the birth and success of Warby Parker, as well as more management lessons Gilboa learned along the way, in addition to the company's focus around racial equality, civic engagement, and people-first leadership during the pandemic. Entrepreneurs will be inspired by this uncommonly thoughtful and socially conscious leader.

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