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side-by-side of Elon Musk in PayPal's early days in 1999 and then in 2024

Elon Musk today runs several more companies than he did in 1999, when the photo on the left was taken. AP / Richard Bord/WireImage via Getty Images
  • Some of Silicon Valley’s biggest names are in their tech bro era.
  • It wasn’t always like this — many Big Tech CEOs have shed more nerdy personas from their startup days.
  • Here’s a look at tech’s most influential executives then and now.

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Mark Zuckerberg isn’t the only tech CEO whose style has noticeably evolved over the years.

Other Big Tech leaders have significantly changed up their looks since starting their companies; some are nearly unrecognizable (we’re looking at you, Jeff Bezos.)

Here’s a look at the style transformations of some of tech’s biggest names:

Jeff Bezos

Amazon has come a long way from just selling books, and its founder, Jeff Bezos, is also very different today. Getty Images

Bezos founded Amazon from his garage in Bellevue, Washington, in 1994. He attributes his new look partly to working out with a celebrity personal trainer and changing his diet.

Michael Dell

Dell founded his company, initially called PC’s Limited, in 1984 while still a student at the University of Texas in Austin. Dell / Errich Petersen/SXSW Conference & Festivals via Getty Images

Dell is another member of the college dropouts-turned-tech founders club.

Larry Page and Sergey Brin

Larry Page and Sergey Brin founded Google in 1998. Kim Kulish/Corbis via Getty Images / Getty

Larry Page and Sergey Brin founded Google in 1998.

Elon Musk

Elon Musk today runs several more companies than he did in 1999, when the photo on the left was taken. AP / Richard Bord/WireImage via Getty Images

The photo at left shows Musk in 1999, around the time the “PayPal mafia” was formed.

Musk has said he doesn’t care for exercise and “almost never” works out, though he’s credited fasting and the weight loss drug Wegovy with his appearance today.

Bill Gates

Fun fact: The photo on the left is actually Gates’ mugshot from when he got a speeding ticket without his license in 1977. Oklahoma County Sheriff’s Department/Getty Images / CHRIS JACKSON/POOL/AFP via Getty Images

Gates and the late Paul Allen cofounded Microsoft from a garage in Albuquerque, New Mexico, in 1975.

Jack Dorsey

Dorsey has been sporting a beard in the years since he stepped down as CEO of Twitter in 2021. Kara Andrade/AFP via Getty Images / Joe Raedle/Getty

Twitter was founded in 2006. Cofounder Dorsey has been seen with a full beard pretty regularly since departing as CEO and focusing his efforts more on cryptocurrency at Block, formerly Square.

Richard Branson

At left is Richard Branson in 1969, one year before he started the Virgin brand. PA Images via Getty Images / Brendon Thorne/Getty Images

Richard Branson started the Virgin brand in 1970 with a mail order record business.

At 73 years old today, Branson’s day-to-day life still features plenty of exercise, from tennis and cycling to kite-surfing.

Anne Wojcicki

Anne Wojcicki is the CEO of DNA testing company 23andMe and the younger sister of former YouTube CEO Susan Wojcicki. Donald Bowers/Getty Images for The Weinstein Company / ETIENNE LAURENT/AFP via Getty Images

Anne Wojcicki founded genetic testing company 23andMe in 2006.

Whitney Wolfe Herd

Whitney Wolfe Herd became the world’s youngest self-made female billionaire after taking Bumble public. Kate Warren for The Washington Post via Getty Images / Dipasupil/Getty Images

Whitney Wolfe Herd founded Bumble in 2014 and stepped down as CEO last year.

Evan Spiegel

Snap CEO Evan Spiegel was the world’s youngest billionaire in the year 2015, when he was 25 years old. J. Emilio Flores/Corbis via Getty Images / Matt McClain/The Washington Post via Getty Images

Evan Spiegel co-founded Snap, which owns services like Snapchat, in 2011.

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Tech Then and Now