How Warby Parker Co-Founder Dave Gilboa Balances the Art and Science of Looking at the Future

How Warby Parker Co-Founder Dave Gilboa Balances the Art and Science of Looking at the Future

Dave Gilboa is the co-founder and co-CEO of Warby Parker. An online retailer of glasses, sunglasses, and contact lenses which was founded in 2010. Today Warby Parker is a publicized traded company with a market cap of almost $2 billion and over 3,000 employees.

In today's discussion we look at the importance of values and vision in growing and running a business, how to turn an idea into a product or service, and how Dave sets personal and professional goals. Subscribers to Leading the Future of Work + will also get a bonus episode where Dave talks about how to create trust, the importance of vulnerability, and the one hack he uses to stimulate creative ideas.

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Get ad-free listening, early access to new episodes and bonus episodes with the subscription version of the show The Future of Work Plus. To start it will only be available on Apple Podcasts and it will cost $4.99/month or $49.99/year, which is the equivalent to the cost of a cup of coffee.

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Over the last 15 years, I've had the privilege of speaking and working with some of the world's top leaders. Here are 15 of the best leadership lessons that I learned from the CEOs of organizations like Netflix, Honeywell, Volvo, Best Buy, The Home Depot, and others. I hope they inspire you and give you things you can try in your work and life. Get the PDF here.

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Get the latest insights on the Future of Work, Leadership and employee experience through my daily newsletter at futureofworknewsletter.com

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Episoder(1186)

Anthropic Built an Early Warning System for AI Job Loss, Here's What It's Already Detecting

Anthropic Built an Early Warning System for AI Job Loss, Here's What It's Already Detecting

March 5, 2026: The company making AI (Anthropic) just published real data on what AI is actually doing to jobs — and the finding that should concern everyone isn't layoffs. It's that the hiring door f...

6 Mar 48min

AI Is Hiring, Gen Z Is Struggling, Your Meetings Are Fake, and Our Schools Are Broken

AI Is Hiring, Gen Z Is Struggling, Your Meetings Are Fake, and Our Schools Are Broken

March 4, 2026: The ECB just released new data showing companies that use AI are hiring, not firing — but the full story of what happened to bank tellers reveals why that optimism has a shelf life. USA...

4 Mar 41min

The CEO AI Paradox, Job Hugging, and Why Electricians Are the Hottest Job in Tech

The CEO AI Paradox, Job Hugging, and Why Electricians Are the Hottest Job in Tech

March 3, 2026: The hype around AI and jobs is loud. The actual data tells a more nuanced story. This week, Stanford economist Nick Bloom released the most rigorous study yet on AI's impact on employme...

4 Mar 37min

Solving the $2 Trillion Student Debt Crisis with U.S. News & World Report CEO Eric Gertler

Solving the $2 Trillion Student Debt Crisis with U.S. News & World Report CEO Eric Gertler

Many parents and leaders are wondering if a college degree is still worth the high educational costs. With student debt reaching nearly $2 trillion and the AI impact changing the future of work, the t...

2 Mar 48min

Jack Dorsey Just Fired 40% of His Company. Stock Soared 24%. He Says You're Next

Jack Dorsey Just Fired 40% of His Company. Stock Soared 24%. He Says You're Next

February 27, 2026: Jack Dorsey cuts 40% of Block's workforce — 4,000 jobs — credits AI, and predicts most companies will follow within a year. We do a deep dive on whether this is genuine AI transform...

27 Feb 38min

Engineers Are Burning Out, Young Workers Are Shut Out, and Trade Schools Are Suddenly Elite

Engineers Are Burning Out, Young Workers Are Shut Out, and Trade Schools Are Suddenly Elite

February 26, 2026: Engineers are facing a productivity panic as coding agents accelerate output — and pressure — at the same time. Nvidia just posted a staggering quarter, underscoring how fast the in...

26 Feb 36min

Anthropic Abandons Safety Promise, JPMorgan Replacing Workers, & The Top Skills for 2026

Anthropic Abandons Safety Promise, JPMorgan Replacing Workers, & The Top Skills for 2026

February 25, 2026: This week Anthropic — one of the companies most associated with responsible AI — gutted the safety commitment it made in 2023. The same week the Pentagon gave its CEO a Friday ultim...

25 Feb 37min

Anthropic Moved Into Your Office, the Fed Admitted It Can't Help, and Goldman Said It Was All for Nothing

Anthropic Moved Into Your Office, the Fed Admitted It Can't Help, and Goldman Said It Was All for Nothing

February 24, 2026: Five major stories broke in the last 24 hours at the intersection of AI and the future of work — and they're all in conversation with each other. Anthropic launched Claude directly...

25 Feb 47min

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