When 2 CEOs walk into a bar ...

Betsy Alexander, CNBC
How to be a leader: Lessons from two top execs

Each week CNBC's "Raising the Bar" series will provide insight into the minds of business leaders as they talk candidly in some of Manhattan's most interesting watering holes about everything from making mistakes to making it big.

When two CEOs walk into a bar—in this case, DailyMail.com North America's Jon Steinberg and Warby Parker's Neil Blumenthal—the talk turns to everything from micro- vs. big-picture managing and to whether a college degree, particularly one from an Ivy League School, matters these days. (The answer: Not so much.)

Is college even worth it for entrepreneurs?

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.

Read MoreA phone case that corrects your flaws?

"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?'"

Read MoreWarby Parker co-founder on disrupting his own model

And if you're interested to know what CEOs are drinking these days ...

The Cocktails


6 oz. Booker's 12-year-old Bourbon

2 oz. Sweet vermouth

2 splashes "Bitter Truth" Orange Bitters

Stir, don't shake! Present in a martini glass over 1 ice cube, with a cherry and an orange twist


Pour Johnny Walker Black Label over 1 extra large ice cube into a rocks glass. Garnish with either a lemon or orange twist.

Look for two more business leaders "walking into a bar…" each week on RAISING THE BAR.

Related Tags