13 Former Employees Leaving Microsoft To Build Billion-Dollar Companies

Rich Barton – Founder of Expedia, Zillow, and Glassdoor

Years at Microsoft: About 8.5

Companies founded: Expedia, Zillow, and Glassdoor

Valuations: $12 billion, $13 billion, and $1.2 billion, respectively

Rich Barton pitched the idea for online travel company Expedia directly to Bill Gates in the 1990s. It operated as a division of Microsoft until 1999 when it spun off as a public company.

Barton next cofounded online real estate company Zillow, which launched in 2006, and then online employment data company Glassdoor, which launched in 2008. Glassdoor ended up selling to a Japanese HR company in 2018 for $1.2 billion, and Barton returned to Zillow as CEO in 2019, after a nine-year hiatus.

He is now on the board of Netflix and other companies.

Gabe Newell: Valve

Gabe Newell – Co-founder of Valve

Years at Microsoft: 13

Company: Valve

Valuation: $10 billion as of March 2019

Gabe Newell dropped out of Harvard University in the early 1980s to join Microsoft (Steve Ballmer, who would later serve as CEO, actually recruited him). Newell left in 1996 to start game developer Valve, which had early success with the Half-Life franchise and now with gaming platform Steam.

Darrell Cavens: Zulily

Darrell Cavens, CEO of Zulily

Years at Microsoft: About 1.5

Company: Zulily

Valuation: Acquired in 2015 for $2.4 billion

Darrell Cavens is Co-founder and former CEO of e-commerce company Zulily. Cavens left a position as a Director at Microsoft in 2009, launched Zulily in 2010, took it public in 2013, and sold it to the owner of QVC for $2.4 billion in 2015.

He is now on the board of directors of several companies including food delivery company Deliveroo and marketplace app OfferUp, founded by fellow Microsoft alum Nick Huzar.

Dan Lewis: Convoy

Dan Lewis – Co-founder and CEO of Convoy 

Years at Microsoft: 3

Company: Convoy

Valuation: $2.75 billion as of November 2019, according to PitchBook

Dan Lewis cofounded trucking startup Convoy after stints at Microsoft, Google, and Amazon. The company raised $400 million last fall.

Lewis is generally known as an ex-Amazonian because Convoy is backed by Amazon CEO Jeff Bezos and was cofounded with another former Amazon employee, but he actually spent a bit more time at Microsoft.

Manny Medina: Outreach

Manny Medina – CEO of Outreach

Years at Microsoft: 6

Company: Outreach

Valuation: $1.1 billion as of April 2019, according to PitchBook

Manny Medina, who formerly worked as a director of business development at Microsoft, cofounded sales software company Outreach in 2014 and serves as CEO.

Nick Huzar: OfferUp

Nick Huzar – CEO and Co-founder of OfferUp

Year at Microsoft: 1

Company: OfferUp

Valuation: $1.39 billion as of August 2018, according to PitchBook

Nick Huzar is CEO and Co-founder of second-hand goods selling startup OfferUp, which is taking on companies like Craigslist and eBay.

Years at Microsoft: About 12.5

Company: Auth0

Valuation: $1.16 billion as of May 2019, according to PitchBook

Eugenio Pace spent more than a dozen years at Microsoft before leaving to start cybersecurity startup Auth0. He is CEO of the company, which doubled its valuation in 2019 to more than $1 billion after just one year.

Brent Frei – CEO of Smartsheet

Years at Microsoft: 2.5

Company: Smartsheet

Valuation: $6.1 billion market cap as of Thursday

Brent Frei is a Co-founder of Seattle-area collaboration software company Smartsheet, which went public in 2018 and is now worth about $6 billion.

Frei is now a Smartsheet board member and the CEO of an agricultural tech startup called TerraClear. He worked for Microsoft in the 1990s and later worked as an Executive Vice President of Intellectual Ventures, an “invention and investment business” founded by fellow Microsoft alum Nathan Myhrvold.

Tony Hsieh – CEO of Zappos

Years at Microsoft: Stayed on at Microsoft after it acquired LinkExchange in 1998, but left soon after to start Zappos as a Co-founder in 1999.

Company: Zappos

Valuation: Acquired by Amazon in 2009 for $1.2 billion

Before he sold e-commerce shoe company Zappos to Amazon for $1.2 billion in 2009, Tony Hsieh sold his first startup, LinkExchange to Microsoft in 1998 for $265 million.

Samir Bodas: Icertis

Years at Microsoft: 8

Company: Icertis

Valuation: $1.15 billion as of July 2019, according to PitchBook

Icertis CEO and Co-founder Samir Bodas started the cloud-based contract management software company in 2011. He previously worked at Microsoft in the 1990s, most recently as a director.

Robert Hohman – Co-founder and CEO of Glassdoor

Years at Microsoft: 3

Company: Glassdoor

Valuation: Acquired in 2018 for $1.2 billion

Robert Hohman co-founded Glassdoor with Barton in 2007. He served as the company’s CEO until January and is now chairman.