The 10 Most Eligible CEO Bachelors

Pete Cashmore with girls

This is part of our series on The Sexiest CEOs Alive. 

They’re sexy. They’re smart. They’re powerful. They run big companies. And they’re single.

These CEO bachelors have it all—and women are lining up to meet them. 

Many of these bachelors are in the tech world, but there are some in fashion and entertainment.

Jeremy Stoppelman

Company: Yelp

Age: 34

Hometown: Arlington, VA

Fun fact: Stoppelman has a dog named Darwin.

David Karp

Company: Tumblr

Age: 26

Hometown: New York City

Fun fact: He dropped out of high school at the age of 15 and was home-schooled after that.

Daymond John

Company: For Us By Us (FUBU)

Age: 43

Hometown: New York City

Fun fact: He started out making and selling tie-top hats on the streets of Queens, NY.

Jack Dorsey

Company: Square

Age: 35

Hometown: St. Louis

Fun fact: The creator of Twitter recently bought a gorgeous $10 million home in San Francisco, but fantasizes about living on a houseboat.

Matthew Flannery


Age: 35

Hometown: Lake Oswego, Oregon

Fun fact: Flannery founded the micro-finance site in 2005 with his (now ex-)wife Jessica Jackley.

Pete Cashmore

Company: Mashable

Age: 27

Hometown: Banchory, Scotland

Fun fact: Cashmore lives in New York City, but splits his time between Scotland, San Francisco, New York and Los Angeles.

Ryan Seacrest

Sean Combs

Company: Sean John

Age: 42

Hometown: New York City

Fun fact: Combs has said that he got his nickname 'Puffy' because of his bad temper as a kid. 'Whenever I got mad as a kid, I used to always huff and puff,' Combs told Jet magazine in 1998. 'I had a temper. That's why my friend started calling me Puffy.'

Tony Hsieh

Company: Zappos

Age: 38

Hometown: San Francisco's Bay Area

Fun fact: Hsieh is currently investing $350 million of his own money into revitalizing downtown Las Vegas, where Zappos will be moving in 2013.

Ben Rattray


Age: 32

Hometown: Santa Barbara

Fun fact: Rattray founded, a company that promotes social change, after his brother told him that he was gay and described the discrimination that he faced.

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