What next? A brief history of tech stars and their second acts

F. Scott Fitzgerald didn’t know everything
The tech industry in 2015 is shaped by one executive’s spectacular second act: Steve Jobs, exiled from the company he helped build, returned triumphantly in 1996 to take back control and transform it into a world-changing electronics company. It’s a story that everyone knows, but it’s one that’s almost unique in the tech industry. More common is a different kind of second act: one in which a leader or visionary leaves (voluntarily or not) the role that made them famous and tries something else, something new. Sometimes these new gigs are calmer and more low-key than their first act; sometimes they might seem to be in a very different field; and sometimes they take a tech leader to new heights.

Elon Musk
In 2001, Elon Musk was deposed as CEO of PayPal, a company he helped found and focus on online payments. The coup was motivated, depending on who you ask, over either his autocratic management style or his attempt to move PayPal’s infrastructurefrom Unix to Windows. Most people would’ve been satisfied with having created a service that redefined how people pay for things, and also with a $165 million payout. Instead, Musk went for a double second act, pouring his fortune into Tesla, which aims to transform how cars are powered, and SpaceX, which seeks to make manned spaceflight profitable. It’s pretty difficult to imagine two less grandiose goals to tackle.

Ev Williams
Pyra Labs, co-founded by Ev Williams in 1999, was supposed to make (boring) project management software. But they built a publishing tool for internal use that they called Blogger, which quickly became an outward-facing service, which quickly brought blogging mainstream and got Pyra Labs acquired by Google in 2003.

Flash-forward a few years: Williams leaves Google and helps found Obvious Corp., a sort of incubator with several projects in progress; one of them, launched in 2006, was originally called twttr, and was conceived of as an SMS-based publishing network. Nearly a decade later, Twitter has come to define Web publishing for the ’10s as much as blogging did for the ’00s. Will Williams’s next startup focus on even shorter posts?

Jack Dorsey
While Williams was an important part of Twitter’s origin story, it was Jack Dorsey who laid the foundations for its technology, after having ruminated on similar ideas for much of the first half of the ’00s. Dorsey was Twitter’s CEO in its early years. However, the microblogging service was barely out if its infancy when he launched another endeavor: Square, a service that made it easy to accept credit card payments on smartphones. The company had reached beta status by 2010. Twitter is a media darling and may get more press, but more people probably encounter Square, which aggressively moved to replace standard cash registers with iPads, in real life. In a Jobsian move, Dorsey has also returned to Twitter as CEO, though that seems temporary.

Andy Rubin
Maybe Rubin didn’t have so much a second act as a second try. He was one of the co-founders of Danger, Inc., a company whose Danger Hiptop phone-PDA combo — a smartphone, essentially — was way, way ahead of its time when it arrived on the market in 2002. Rubin left the company, which ended up stagnating before being absorbed by Microsoft, but he wasn’t done with mobile. He quietly started another company, Android, which focused on mobile software, and which was, just as quietly, bought by Google in 2005. Android was the world-changer that proved that sometimes the second time’s the charm.

Carly Fiorina
In tech circles, Carly Fiorina is best remembered for her late ’90s/early ’00s stint as CEO of Hewlett-Packard, which was extremely controversial within the industry; she fought the company’s founding families, dismantled the egalitarian “HP Way,” and, most famously, engineered a much-derided merger with Compaq. Fiorina was fired in 2005, but has chosen a second act even more grandiose than conquering space: politics. Undaunted by a failed 2010 Senate run that featured one of the weirdest campaign ads in living memory, Fiorina is currently running for the 2016 Republican presidential nomination, and in her first big debate managed to humble Donald Trump.

Henry Blodget
Perhaps nobody on this list had their first act end as dramatically as Henry Blodget: as a stock analyst for Merrill Lynch during the dot-com boom he promoted stocks in public that he privately admitted weren’t worth much; he eventually paid a $2 million civil fine and was banned from the securities industry. For his second act, he turned to journalism: he helped found Silicon Alley Insider in 2007, which quickly become part of the Business Insider empire, where Blodget is the editor in chief and CEO. Much of the hostility within the industry towards him has dissipated, and many view him as a sort of kooky uncle, especially when he produces oddball it-happened-to-me articles like this one.

Kevin Rose
Kevin Rose is perhaps emblematic of the sort of second acts many tech execs who hit it big young have: the anticlimactic kind. Rose founded Digg, which for a few years in the ’00s was one of the most important websites on the Internet, with hundreds of millions of views and the power to make or break stories that it linked to. A baby-faced Rose appeared on the cover of BusinessWeek in 2006, though he later claimed the hat and headphones weren’t his. After a disastrous 2010 redesign evaporated Digg’s goodwill, Rose started an app-making shop that got bought by Google and ended up briefly working on Google+, a project that, as we all know, did not end in glory.

James Gosling
Some second acts are lower-key by choice. James Gosling created Java for Sun Microsystems in 1995; when Sun was merged into Oracle in 2010, Gosling left in short order, which was seen as emblematic of the culture clash between the two companies. After a brief five-month stint working for Google, Gosling went in a completely different direction: he took a job with Liquid Robotics, helping build low-power automatic seafaring robots. I imagine this job has to be significantly less stressful than his previous high-profile gigs.

Steve Jobs (again)
Steve Jobs’s return to Apple is so important to the industry that it’s easy to forget that he did have another, truly different second act. In 1986, after he had been ousted from Apple, Jobs spent $5 million to fund the spinoff of LucasFilm’s Graphics Group, which was quickly renamed Pixar. After years of failed attempts to market to special effects artists the custom hardware and software the group had developed, and only a little traction from doing commercial animation, Jobs was almost prepared to sell the company in 1995, when Toy Story was released to near-universal acclaim and massive box office success. The rest was history. Even Jobs’s secondary second act was pretty good.

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