The quality of an organisation is reflected by the quality of its questions and a number of the most storied venture investors, such as Michael Moritz from Sequoia Capital, started out as journalists. Sarah Milstein also began her journey towards corporate venturing by first climbing her way up through the journalist ranks at O’Reilly Media.
Starting in 1998 as a freelance journalist, Milstein became an editor for the Missing Manual series – a collection of books offering guidance on a number of software platforms similar to the For Dummies series – in 2003. The success of the series would propel her to became senior editor in 2004 before becoming a managing editor for O’Reilly in 2005. Later, she would become chief publishing evangelist at the firm between 2006 and 2007 and founded O’Reilly’s Tools of Change conference.
While adding an MBA from University of California Berkeley to her Rutgers bachelor’s degree between 2007 and 2010, Milstein also provided consulting with a number of startups, including Twitter, Metaweb, and Boing Boing, advising on content strategy, community management and product development.
Before coming back to O’Reilly through its corporate venturing arm O’Reilly AlphaTech in 2015, Milstein tried her own hand at entrepreneurship, founding and running Lean Startup Productions, a media company aimed at teaching business leaders about startups.
Since returning to the O’Reilly fold, Milstein has set up its indie.vc programme, which aims to invest in startups looking to grow revenues over valuations. She also assists in identifying investment opportunities, runs the unit’s entrepreneurship and mentoring programme for portfolio firms and provides advice to its startups.