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Meet the biggest tech billionaire you’ve never heard of

Linkedin founder Reid Hoffman is Silicon Valley’s most modest – and low-key – billionaire. But his predictions of work trends have been eerily accurate. In a rare interview, he tells Simon Usborne why he believes artificial intelligence might be more frie

SIMON USBORNE

Six years have passed since Reid Hoffman oversaw the sale of Linkedin to Microsoft, confirming his status as a billionaire, and now he can do anything he wants every day for the rest of his life. He could have the private jet, the superyacht, the luxury doomsday bunker... But he wants none of it.

Hoffman, 55, is talking to me via Zoom from his home office, which is in Seattle and could barely be more modest. A daybed, strewn with clothes, faces a small wallmounted TV. There’s an underdesk exercise bike and a folding screen propped against a wall, which he sometimes uses as a backdrop for TV appearances. In front of it all sits a man with a net worth estimated at just under $2 billion.

It was in similarly modest digs in Silicon Valley that Hoffman came up with the idea for Linkedin, the professional social network that is, depending on your profession and cynicism levels, an annoyingly earnest repository for backslapping and self-promotion, or a vital tool for finding jobs and influencing people. Twenty years later, Linkedin, which went live in 2003, has more than 875 million members. And yet, unlike Mark Zuckerberg who became an instant celebrity after founding Facebook, Hoffman, a fellow titan of Silicon Valley who made his mark at a similar time, is no household name.

‘I don’t think I ever went through the celebrification that tends to happen with these things,’ he says. ‘And I prefer that. I don’t want to be world-known, I want to be known by the people who are trying to accomplish the kinds of things where I might be a useful part of their network.’

It’s hard not to compare Hoffman with another tech giant, now making a name for himself in social media. On the day we speak, Elon Musk is sacking hundreds of people at Twitter, days after taking its reins. Musk, the founder of Tesla and Spacex – and wouldbe coloniser of Mars – is apparently everything Hoffman appears not to be: impetuous, arrogant, vainer than Narcissus.

Yet the men cut their teeth in the same place as alumni of the ‘Paypal Mafia’, a group of highflyers who worked at the online payments company. Hoffman was executive vice president when ebay bought Paypal for $1.5 billion in 2002. Other members include Peter Thiel, the libertarian entrepreneur and political activist, as well as all three founders of Youtube. Is Hoffman surprised by his old pal’s decisions? ‘Elon is one of those, “I have a vision, I put it all on the line, and I go for it” guys.’ He hasn’t spoken to Musk since the Twitter takeover. ‘He’s very bold, very vision-driven, and we’re better off in society to have people like that. And now he’s approaching Twitter the same way… and I would approach it differently.’

His words are loaded with understatement, but it’s a very Hoffman response. If Musk’s style is impulsive disruption, Hoffman’s could be described as collegiate dynamism. His success is built on a quiet mastery of corporate influence and diplomacy. That Linkedin appears to embody his ethos is no mistake; these are the skills that have helped create perhaps the world’s greatest networker. These themes are central to Hoffman’s new book. The Startup of You, co-written with Ben Casnocha, a 34-year-old tech entrepreneur and venture capitalist, is a comprehensive update of a book first published a decade ago. It’s a guide to a workplace that has transformed in the past 10 years, interwoven with Hoffman’s story and some epic name-dropping.

‘In the original edition, the word “Uber” didn’t appear,’ says Casnocha, who is also on our Zoom call. ‘The gig economy wasn’t a concept that was even contemplated.’ In the update, Hoffman describes how a decade of technological advances and pandemic disruption have turned the career ladder into a jungle ‘with trees we are all scrambling to climb without falling’.

To survive, the duo argue that we should all see ourselves as startups. As hierarchies flatten and more careers become ‘portfolios’, professional loyalty is to each other, via networks, rather than to traditional bosses. ‘We are now living in a free-agent world,’ they add. We should all operate with a mindset of ‘permanent beta’, in constant test mode, waiting for opportunity to grow and cash in. Some might struggle with parts of a book that at times feel like a 300-page Linkedin post: a bit earnest, a bit heavy on mantra (‘serendipity is best played as a team sport’). But it contains a compelling sense of learning at the

I have a whole bunch of things I’d suggest to Elon about what I’d do differently with Twitter

feet of a master – the unanointed King of Connection.

Hoffman’s networking chops are legendary in Silicon Valley, where he has bankrolled dozens of startups, most notably Airbnb, in his day job at Greylock Partners, the venture capital firm he joined in 2009. He sits on multiple boards and his diary is packed with exclusive tech conferences and fancy dinners at which he is renowned for starting meals by asking everyone to list the topics they hope to discuss.

Hoffman has hotlines to world leaders and business giants. The guestlist for his podcast, Masters of Scale, which he started in 2017, reveals his pulling power; he has chatted with the founders of Facebook, Netflix, Starbucks and Spotify, as well as Barack Obama and – last April – Prince Harry, in his role as ‘chief impact officer’ of Betterup, a Californian business coaching company.

He is also a philanthropist, an advocate of women in business, and a prolific political donor to predominantly Democrat candidates – an outlook not always associated with the libertarian capitalism that washes through parts of Silicon Valley. He detests Donald Trump, once describing him as ‘a Chernobyl… within the US system’. We speak hours after Trump drops heavy hints about a comeback candidacy, and a week before the US midterm elections.

‘I have deep concerns,’ he tells me. ‘We had in this country the greatest assault on democracy in my lifetime – the claim that the 2020 election was stolen and the January 6 insurrection – and yet a bunch of deeply propagated lies continues. It sorrows me and puts a substantial risk on the table.’

Hoffman inherited a liberal bent from his father. Bill Hoffman, a lawyer whose early clients included members of the Black Panthers, was studying at Stanford when his son was born in 1967.

A year earlier at the university, the US government had begun developing the earliest version of what became the internet.

Bill and Deanna Hoffman, also a lawyer, separated early. An only child, Hoffman found a social network – and an escape – in fantasy board games including Dungeons & Dragons. He got his first job writing game reviews and testing scenario packs. He persuaded his father to send him to a progressive boarding school in Vermont, where he had vague notions of changing the world.

Hoffman studied symbolic systems (or the relationship between computing and human intelligence) at Stanford, and philosophy at Oxford. At Stanford he met his wife Michelle Yee, a former clinical speech pathologist (they have no children), and Peter Thiel, who would go on to found Paypal. ‘His friends said you should meet this pinko commie,’ Hoffman once said of Thiel, who has funded Trumpbacking Republicans. ‘My friends said you should meet this person to the right of Attila the Hun.’ The duo became friends, and spent hours debating politics, at one point clashing over Margaret Thatcher’s ‘no such thing as a society’ line. ‘Reid was always interested in creating communities,’ Thiel told The New York Times.

Abandoning a possible life in academia, Hoffman took jobs at Apple and Fujitsu in the mid1990s. Both companies were experimenting with social networks. He launched his own, Socialnet, in 1997. Arguably ahead of its time, it soon fizzled out.

A year later, Hoffman joined Thiel at the company that became Paypal after it merged with an online bank founded by Elon Musk.

As chief operating officer at Paypal from 2000, his job was to manage fraught relations with credit card companies and regulators. It drew on all his charm, calm and networking skills. Hoffman, who Thiel described as Paypal’s ‘firefighter in chief’, worked 100-hour weeks and helped seal the ebay deal in 2002, which made both men multimillionaires. Thiel bought a Ferrari; Hoffman

In the next five years there’ll be an AI tool for every job that produces informational output

invested in a solar-panel company and bought a green Acura, a marginally posher version of a Honda.

Silicon Valley was about to boil over as a crucible of social networking. Seeing a gap in the market for a site for professionals, Hoffman launched Linkedin in 2003, the same year Myspace emerged. A few months later, he introduced Mark Zuckerberg to Thiel, who became the first outside investor in Facebook, which launched in 2004 (Hoffman had all his chips on Linkedin).

Away from the attention the pure social networks and their enigmatic bosses were getting, Linkedin quietly flourished. Hoffman became a billionaire, only adding to his wealth when Microsoft bought Linkedin for $26.2 billion in 2016 (Hoffman joined the board of directors at Micrsoft a year later and remains active at Linkedin). The site was ‘the turtle that won the race,’ he tells me.

Linkedin came to distil Hoffman’s vision of a changing workplace, where personal branding and the power of the network become ever more vital. He sees no end to remote working as part of a hybrid model that he embraces. ‘But at the same time we’re creatures of the polis, or city,’ he says, quoting Aristotle. ‘There’s an energy and a creativity you only get when you’re in the same room.’ He’s also watched a cultural shift that the pandemic hastened – a sometimes generational

rebalancing of power as workforces reject presenteeism and brutal bosses. He sees this as an opportunity rather than a threat. ‘If you’re in that older generation, you should be thinking about what you can learn,’ he says. ‘Ask yourself if you should have a more compassionate side to how you’re running things.’

He dismisses any notion that we’ve raised a generation of workshy snowflakes, but says that the purported power shift has limits. ‘The way that you accomplish big things is you work hard, you’re focused, you’re disciplined, and you have delayed gratification,’ he says.

He has become heavily involved in the AI industry. He’s on the board of Openai, a research lab and tech company that Musk co-founded in 2015 (Thiel and Microsoft are also backers). Openai’s most visible application is DALL-E, which turns sentences into images. When I type ‘a painting in the style of Renoir of a journalist talking to a billionaire in a polo shirt and glasses’, it spits out a remarkably convincing work of art, generated in seconds, pixel by pixel.

One of Openai’s other projects, a language model called GPT-3, is being used to write screenplays, marketing emails and to develop video games. Earlier this year, Hoffman co-founded Inflection AI, a startup that will also look at language processing. ‘Over the next five years I think there will essentially be an AI tool for every job that produces some kind of informational output,’ he tells me. ‘It could be a painting, a journalist’s article, a doctor’s prescription, a legal sheet, a song.’

In 2017, Putin said ominously of AI that ‘whoever becomes the leader in this sphere will become the ruler of the world’. Musk himself has in the past raised the alarm over ‘scary outcomes’ like in ‘The Terminator’, despite now developing an AI robot called Optimus. Hoffman has never seen AI as an existential threat, nor even a longterm threat to jobs; he assures me it will only ‘amplify’ human capability. ‘I do think we’re on an amazing next step to changing what we can do,’ he says.

Tech evangelism feels potent coming from a man who has built a career and a fortune by being ahead of the game while seeming to be sane. I suggest that one reason he operates without the notoriety or profile of a Musk or Zuckerberg is that he isn’t crazy. ‘But crazy is, like… it’s madness when it’s wrong and it’s genius when it’s right,’ he says. In an age of political polarisation, he says the advantage of staying friends with geniuses with antithetical politics is the potential to influence them. Not that it always works. ‘So, while I have a whole bunch of things I’d suggest to Elon about what I would do with Twitter differently, he hasn’t called me and my calling him won’t change his mind.’

Hoffman is a notorious workaholic and once had four phones (he tells me he now only has three). A few years ago, Thiel said his friend was so effective and persuasive in business because he was the ‘opposite of a sociopath’, but that this also led to self-neglect. He says it’s something he’s working on. He meditates and has a personal trainer. ‘I’m actually on day six of an eight-day fast,’ he says. ‘I just have 200-ish calories in bone broth a day. It’s a bit of a challenge.’

He spends rare downtime with his wife, going out for dinner, or hosting – and winning – rounds of the Settlers of Catan board game with members of the Silicon Valley elite. Recently, he switched his battered Acura for a Tesla, but beyond that, what’s the most billionaire-ish thing he’s done? He says he’s more focused on ‘trying to give every individual on the planet an ability to take control and invest in their own career… I don’t go out and buy boats because I don’t think they’re useful.’ Not even a small one? ‘Well, OK, a small one,’ he says. Above all, he sees himself as ‘more of a humanist than a technologist’. He embraces the potential of technology to improve societies, an outlook that has perhaps rarely felt so optimistic.

Our hour is up. Hoffman is due to dial into a board meeting at Aurora, an autonomous vehicle startup he began backing in 2018. ‘I’ll raise this desk, get on the bike and I’ll be cycling during the meeting. It’s one of the hacks we learned during the pandemic. Just sitting here all the time was superbad for our health.’

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