Warby Parker’s leap: From affordable glasses to AI game-changer

Dave Gilboa is co-founder and co-CEO of Warby Parker, the eyewear brand that started with a pair of lost glasses while he was studying at Wharton Business School.

In 2010, he and three friends pooled their savings and bought the company’s URL for $9. Almost everyone they spoke to said the idea would not work.

Dave joins us to talk about the brand’s early days, being so frugal they practically refused to buy pens, experimenting with retail, handling rejection, raising more than half a billion dollars before going public, and staying focused on mission and purpose.

He also shares new details about Warby Parker’s partnership with Google to develop AI-powered eyewear, and why he believes smart glasses may finally become a reality. 

Topics discussed:

| 00:00 – Introduction
| 02:14 – Dave Gilboa’s early life: from Sweden to San Diego
| 03:10 – From pre-med to management consulting at Bain
| 04:57 – Working in finance and realizing he wanted more meaning
| 05:44 – Losing his glasses and discovering a billion-dollar idea
| 07:32 – Turning frustration into the Warby Parker startup
| 08:45 – Why glasses are overpriced and ripe for disruption
| 11:14 – How “Warby Parker” got its name from Jack Kerouac’s journals
| 14:49 – Bootstrapping with friends and pooling $120K in savings
| 16:13 – Spending every dollar wisely: the three-spend rule
| 18:16 – Launch week chaos and the 20,000-person waitlist
| 25:36 – Rejection at Wharton and early pushback on pricing
| 32:29 – Fundraising journey: from seed round to Series G
| 32:58 – Taking Warby Parker public through a direct listing
| 34:06 – How to raise capital the right way and keep control
| 36:12 – Protecting the mission by walking away from wrong investors
| 37:43 – The “Buy a Pair, Give a Pair” program: 20 million glasses donated
| 40:24 – Home Try-On and inviting customers into their apartments
| 41:14 – The yellow school bus pop-up tour that drove national buzz
| 44:11 – Scaling brick-and-mortar retail across the U.S. and Canada
| 45:13 – Expanding into contacts, exams, and full-service vision care
| 45:48 – Partnering with Google to build AI-powered smart glasses
| 46:57 – Why Dave believes smart glasses will finally go mainstream
| 48:27 – How to grow a brand with no marketing budget
| 50:45 – Rapid-fire round: habits, hiring, and advice on focus

About Behind the Business:

Behind the Business is a video series and podcast hosted by Michelle Toh, CNN and Fortune alum, that explores the decisions and philosophies behind today’s most influential leaders. Recorded in studios across the US, the show is grounded in the belief that business is in fact personal, providing the backstories of founders, corporate leaders, investors and creators and how they push through to make the most of both work and life each day. What’s the worst day you’ve faced at your company? How do you cope with crisis or rejection? Or what’s a pinch-me moment you’ll never forget? In each episode, guests get into it all. New episodes every Thursday.

About Michelle Toh

Michelle Toh is an award-winning international journalist. She has covered some of the top stories in global business and tech, most recently as a reporter appearing across CNN’s digital and television platforms. Before joining CNN, she was an associate editor of Fortune Magazine, and her reporting has appeared in TIME, USA Today, and the South China Morning Post..

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