- Many entrepreneurs have passed through Microsoft in the company's 45-year history, including a handful who have managed to startup businesses that are worth $1 billion or more.
- We rounded up 13 former employees that built unicorn companies, including Daniel Dines of UIPath and Rich Barton, who cofounded the trifecta Expedia, Zillow, and Glassdoor.
- Are you a current or former Microsoft employee? Contact this reporter via encrypted messaging app Signal (+1-425-344-8242) or email (astewart@businessinsider.com).
- Visit Business Insider's homepage for more stories.
Many entrepreneurs have passed through Microsoft in the company's 45-year history. A Seattle-based economist Microsoft once hired to study its economic impact estimated that the company had helped create 10,000 millionaires by the year 2000.
A few even founded billion- or multibillion-dollar companies. Business Insider compiled a list of 13 ex-Microsoft entrepreneurs who built massive companies like Chinese electronics giant Xiaomi, video game developer Valve, and hot startups like UIPath, Convoy, and Auth0.
The list is not comprehensive. It's also not very diverse.
While there are notable examples of women who have left Microsoft to start successful startups, their businesses are not yet valued over $1 billion. For example, Kieran Snyder spent more than nine years at Microsoft before starting $127 million augmented writing startup Textio, while Daniela Braga spent about seven years at Microsoft before founding $50 million machine learning startup DefinedCrowd.
Microsoft, like most technology companies, has always struggled to reflect the diversity of society, meaning that there have been far fewer people of color and women of all backgrounds in the pool of potential ex-Microsoft founders to begin with. Plus, women and people of color are also disadvantaged when it comes to raising venture capital (and thus, scoring unicorn valuations).
Know someone we missed who should be on this list? Contact this reporter via email at astewart@businessinsider.com, message her on Twitter @ashannstew, or send her a secure message through Signal at 425-344-8242.
Bin Lin: Xiaomi

Years at Microsoft: 11+
Company founded: Xiaomi
Valuation: Around $44 billion.
Bin Lin is one of the cofounders of Chinese electronics giant Xiaomi. He's now the company's president.
Rich Barton: Expedia, Zillow, and Glassdoor

Years at Microsoft: About eight and a half
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's now on the board of Netflix and other companies.
Gabe Newell: 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

Years at Microsoft: About one and a half
Company: Zulily
Valuation: Acquired in 2015 for $2.4 billion
Darrell Cavens is cofounder 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's 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

Years at Microsoft: Three
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

Years at Microsoft: Six
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

Years at Microsoft: One
Company: OfferUp
Valuation: $1.39 billion as of August 2018, according to PitchBook
Nick Huzar is CEO and cofounder of second-hand goods selling startup OfferUp, which is taking on companies like Craigslist and eBay.
Eugenio Pace: Auth0

Years at Microsoft: About 12 and a half
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's CEO of the company, which doubled its valuation in 2019 to more than $1 billion after just one year.
Brent Frei: Smartsheet

Years at Microsoft: Two and a half
Company: Smartsheet
Valuation: $6.1 billion market cap as of Thursday
Brent Frei is a cofounder 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: Zappos

Years at Microsoft: Stayed on at Microsoft after it acquired LinkExchange in 1998, but left soon after to start Zappos as a cofounder 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 the Microsoft in 1998 for $265 million.
Samir Bodas: Icertis

Years at Microsoft: Eight
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: Glassdoor

Years at Microsoft: Three
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.
Daniel Dines: UIPath

Years at Microsoft: About four and a half
Company: UIPath
Valuation: $7.1 billion as of April 2019
Daniel Dines was a software development engineer at Microsoft before leaving to start robotic automation company UIPath in 2005.