Leaning back on their bar stools and dressed casually in jeans, these two CEOs are major players in the digital world.
Blumenthal's online eyewear company offers designer prescription eyeglasses and sunglasses directly to consumers via its website, providing consumers with a boutique-quality alternative that's more affordable. Through its Buy-a-Pair, Give-a-Pair program, Warby Parker has donated more than 1 million pairs of eyeglasses globally to people in need. Steinberg's Daily Mail.com North America is the largest English language newspaper site in the world. Covering everything from politics to pop culture, it's visited by 225 million readers every month.
Now, at Fresco by Scotto in Midtown—where on any given night you may see the likes of Bill Clinton, Jennifer Aniston or other boldface names—Blumenthal and Steinberg share a drink, along with their views on leadership style, college, the next generation and more.
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"I tend to try to be motivational and give sort of the big vision," said Blumenthal.
Steinberg said he prefers to "stay in the foxhole" and "then do the strategy memo, set the direction, do the weekly readouts where we are going over the core metrics. I don't think of myself as a micromanager."
Yet both are concerned about the next generation and know that disruption to their industries could be a threat at any time.
"It's scary," said Blumenthal, "because the [next generation] right now is in their dorm room and they are figuring out a way to unseat us. It's really scary. The question is, What do you do about that?"
"I'll tell you what I do about that," Steinberg said. "When young people email me, I always write them back. I ask them, How can I help? What is your question? I think to myself, 'I could be asking myself for a job in the next five or seven years,' and I have the humility to recognize it. I've seen it happen."
Blumenthal's competitive philosophy is simple: "The Number 1 thing is how do we keep customers happy. ... If customers are happy, they're going to tell other people about us. We're going to grow. We're not going to have to spend a ton of money on marketing, because we have this sort of referral and viral effect," he said.
Both believe the world is changing and so are the opportunities, and it's not where you went to college that counts.
When a kid walks in with a Harvard degree, I don't really care," said Steinberg. "I'm like, 'Well, what do you know how to do? What are you passionate about?'"