The second wedding of Jeff Bezos — so the prevailing narrative goes — pushes the button on what has been a long time planning. The rumoured $10 million (£7.3 million) being spent by the Amazon founder on blinging up Venice — booking up five luxury hotels and every water taxi in the city — isn’t just a way to upgrade the $2.5 million (£1.85 million) engagement ring of his fiancée Lauren Sánchez. On June 24, Venice will serve as the launch site to send Bezos 2.0 into our cultural orbit, the upgrade for already one of the most powerful humans in the world for which he has been in training for years: shaving his head, buffing his body, stiffening his tailoring, hardening his soul.

Now 61, Bezos found himself at the classic crossroads of every successful retirement-age businessman with a failing marriage. Would he choose the grandfatherly philanthropist route of Bill Gates, 69, or the path preferred by one of his own mentors, Warren Buffett, now 94? Would he look instead at the present occupiers of the top spots on the Forbes rich list — the younger bucks Elon Musk and Mark Zuckerberg — and decide that now he has been relegated to No 3, he would prefer ageing down to powering up? Or is there a more mysterious Bezos at work — the one who said at last year’s DealBook Summit in New York, “I gave up on being well understood a long time ago”, but who may only now be beginning to understand himself?

On Sunday night the new film Mountainhead aired on Sky Atlantic. It is a satire based on the world’s three richest men, high on their own tech-bro founder power. Money and myth-making matter; morals barely feature at all. While the show’s creator, the Succession writer Jesse Armstrong, gathers the trio at a fourth friend’s poker night, it is actually better imagined as a stag do or “bachelor party”. We can wonder if Bezos watched as he planned his own — whether he has held one or not remains unclear. By contrast, Sánchez’s gathering in Paris last month seemed a display of her own power — drawing the world’s most Instagrammable women, from Kim Kardashian to Katy Perry, into a series of photoshoots in which Sánchez stood out as the star in white, while those further down the rich list were dressed in background black.

If Bezos does watch Mountainhead he will see a version of himself reflected through the darkest mirror. Venis, the richest human on earth, seems somewhat inspired by Elon Musk, while the second richest is Venis’s tech rival called, confusingly, Jeff. The third richest is an older man called Randall, referred to by the others as “dark money Gandalf”.

Like Randall, Bezos shares with Musk an early childhood obsession with space as a solution to Earth-bound catastrophe. Bezos’s valedictorian speech at his high school in Florida began with the Trekkie mantra “Space, the final frontier” before elaborating on his plans to move polluting human industry off Earth and preserve the planet as an exclusive nature reserve. Bezos has recently said he now directs much of his efforts into Blue Origin, his rocket business, returning to the same dream he held “since I was a teenager”.

In Mountainhead, Randall talks about Earth at one point “as a solid starter planet, but we’ve outgrown it”. He believes tech can solve any problem, even those it creates. By contrast the Mountainhead bros sneer at efforts to vaccinate African children against malaria: a pointed comparison to the central philanthropic mission of Bill Gates.

But now we can stop with the fictional parody. In the real world, Musk, Zuckerberg and Bezos say something astonishing about American invention, vision and drive — collectively they have changed the world we live in. It’s double-edged: while Zuckerberg and Musk have provided the means for us to atomise ourselves online, Bezos was the visionary who transformed us into “one-click” culture, expectant of instant gratification served to us within hours at home with no need to venture into the real world of human interaction. Along with the Alexa devices, Amazon’s early AI technology, Bezos has ensured we are simultaneously fulfilled and unfulfilled. In a profile in Wired magazine in 1999, Bezos goes shopping for chinos with the reporter and indicates the bustling shops. “You see, none of this is going away,” Bezos predicts, wrongly. “The Net can’t replace this experience.”

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There is a caricaturable side to Bezos that his biographer Brad Stone captures in The Everything Store. He describes Bezos’s “Jeffisms” — the oft-repeated parables he uses to explain himself or Amazon — or his “nutters”, as staff informally called them: melodramatic temper tantrums set off by underperforming employees that once ended with “Why are you wasting my life?” Yet when Bezos granted Stone access to staff — he did not himself give an interview, and very rarely does — he issued a caution against “narrative fallacy”, or the human tendency to oversimplify because we love stories.

So yes, the Venice wedding to Sánchez is a far cry from his first wedding in 1993 to MacKenzie Scott, a colleague whom he met at a hedge fund in New York a year earlier. He approached the task of meeting girls analytically. He was “goofy”, he acknowledged to Wired in 1999. “I’m not the kind of person where women say, ‘Oh, look how great he is’, a half-hour after meeting me.” Instead he took up ballroom dancing to increase his contact with girls. In the end Scott told Vogue that she fell in love with his laugh, a remarkable hoot that Stone describes as “like a cross between a mating elephant seal and a power tool”.

The pair married in a hotel in West Palm Beach and celebrated with a late-night party at the pool. Throughout most of their marriage, in which they had three sons and one adopted daughter from China, they remained in damp Seattle. Bezos cultivated an image of aggression in the job — a project was once named “Gazelle” after he casually mentioned they should treat small ailing book publishers like a predator with a sickly gazelle. He also cultivated an image of aggressive frugality. After he became a billionaire in 1998, he continued driving his Honda, saying it was “a perfectly good car”. Two years later he upgraded to a Volvo.

Some put the pivot point in Bezos’s life in 2019, when his affair with Sánchez, the wife of a mutual friend, was revealed. It’s easy to contrast Scott, the writer who studied under Toni Morrison, with Sánchez, the helicopter pilot: depth versus elevation. Sánchez perhaps didn’t fall in love with Bezos’s laugh. But, interestingly, Bezos said in 1999 he found Scott when he was looking for a woman who was “resourceful”; he wanted someone powerful enough to save him in a crisis. “The number one criterion was that I wanted a woman who could get me out of a Third World prison,” he told Wired.

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Sánchez has dragged Bezos into a widely satirised 2023 joint Vogue photoshoot, and her low-cut bodice drew Zuckerberg’s eyes (among others) when Sánchez and Bezos attended Donald Trump’s inauguration in January. Bezos, who in 2017 was said to earn $230,000 every 60 seconds, spends more time in Hollywood and seems now to freely splash the cash. The $500 million yacht Bezos bought in 2023 is too big to moor near Venice. Yet to Bezos’s credit Sánchez, in many ways, does not fit the predictable model of a corporate titan’s too-young, too-appeasing second bride. One of her bachelor party guests was Natasha Poonawalla, philanthropist and wife of Adar Poonawalla, India’s billionaire “Vaccine Prince”. At 55, Sánchez could pilot a prison rescue mission better than most.

Instead the pivot point for Bezos’s new life was going into space on the first Blue Origin human rocket flight in 2021. In April, Sánchez was one of the somewhat meaning-light all-female crew of the same company. But for Bezos, that first trip in 2021 came with an unexpected epiphany. He said he had expected to be blown away by experiencing the fragility of Earth as seen from space. Yet he said in practice the most powerful moment was leaving his family behind. His parents, sister, children and close friends said goodbye to him as if for the last time. Bezos told the DealBook summit last year “it was very interesting to have that feeling from my family”. It was almost as if he saw the fragility of human relationships, rather than the planet, and something in Bezos’s hard shell cracked.

Bezos said on the DealBook stage that when he was a child growing up, both his parents, Jackie and his adoptive father Mike Bezos, were relentlessly positive. It was the secret to their success: Jackie was pregnant with Bezos when she was 16 but finished high school, and later graduated college by attending night school. Mike Bezos was a Cuban refugee who arrived in the United States alone aged 16 and speaking no English — he went on to become an Exxon engineer. They were intensely supportive of Bezos, he told DealBook, and in his family “all the positive emotions were allowed”. The only negative emotion allowed was anger.

This is maybe why, when Jackie and Mike delivered Bezos, aged ten, the bombshell that his real biological father was a Danish-American unicyclist called Ted, Bezos said he reacted unemotionally. Ted, also a teenager when Jackie got pregnant, had been an unreliable father and Jackie asked him to cut off contact when she married. Around the time Ted disappeared, Bezos, aged three, dismantled his cot with a screwdriver — some kind of metaphor for self-reliance. Bezos told Wired in 1999 that hearing about his biological father was no big deal. His parents also told him at a similar time that he needed glasses. “Now that made me cry,” he said.

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Yet last year Bezos told DealBook that he now realised “sadness, fear, anxiety — these things were looked down on” in his family. The resulting mix of drive, positivity and anger were perfect for a founder but not so good for “intimacy”. He revealed that he had “started working on that”, deepening his ties with his family by allowing himself to feel sad or scared. He had “found it very meaningful”.

Throughout his career Bezos has referred to the idea of the “missionary” versus “mercenary”. In a memo to Amazon executives in 2013 he wondered if Amazon could ever be loved not feared. Explorers are cool, conquerors are not cool,” Bezos wrote, “missionaries are cool, mercenaries are not cool.” He claimed his devotion to customer service and long-term goals marks him as a missionary rather than a quick-buck mercenary. But it’s complicated: so many mercenaries fool themselves they are missionaries. Bezos has not yet successfully communicated a convincing idealism, yet his psyche is possibly on the move.

Bezos has reversed his antipathy to President Trump: the pair had numerous public spats during his first presidency. However, in Trump’s latest campaign Bezos, who owns The Washington Post, spiked the paper’s endorsement of Kamala Harris, the first time the paper did not endorse a candidate since the 1980s. After the election Bezos and Sánchez dined with Trump and Musk at his Florida resort, and Amazon donated $1 million to Trump’s inaugural fund. There is no indication the Trumps will attend the wedding.

I saw Bezos in person once, far from the insulated bunker of bros depicted in Mountainhead. While he prepares to fly to Europe and the beating sun of Venice, our paths crossed in the beating sun of Turkey in 2019. I was at an event to mark the first anniversary of the murder of the Washington Post journalist Jamal Khashoggi at the Saudi consulate in Istanbul.

Bezos sat next to Khashoggi’s young fiancée and spoke in tribute to her. “You need to know that you are in our hearts. We are here and you are not alone,” he said. Cynics accused Bezos of making this trip as a way of winning back good PR after his affair with Sánchez went public. I saw a man in that moment just trying to do the right thing.