Dressed in a white, long-sleeve, hooded T-shirt, stone chinos and Clarks Wallabee shoes, Ive said he wanted to draw creative types to the edge of downtown. He has been turning one of his buildings into a home base for his agency’s work on automotive, fashion and travel products. Another is the headquarters of a new artificial intelligence device company that he is developing with OpenAI.

“I don’t know whether it was reckless,” he said of his building acquisitions. “It certainly wasn’t arrogant. It was well intended. But I really felt we could have a contribution.”

Tech executives spending their fortunes on real estate or more imaginative adventures is a staple of Silicon Valley culture. Some buy islands, others build yachts longer than a football field or fund quixotic flying car projects. Ive’s fixation on a single city block, by comparison, seems modest.

But for Ive, Jackson Square also represents personal reinvention. Few people walk away from their profession’s premier job. Even fewer start over again. A self-professed control freak, Ive decided that he had fretted enough over the snugness of each iPhone box, the layout of every Apple Watch component and the curve of every iPad corner. He wanted something new.

At LoveFrom, he has tried to trust his instincts. Buying one building led to buying another. A discussion about a new yarn led to his first fashion apparel. Work with one client, Brian Chesky, the CEO of Airbnb, led to meeting Sam Altman, the CEO of OpenAI.

It is unclear what the real estate spending spree will amount to, and for all of Ive’s success, there have been points when his design instincts and expensive tastes went too far. He has been criticised for putting form over function. Some MacBooks were so thin that the keyboards malfunctioned. Some of Apple’s biggest fans mocked the custom gold watch that the company sold for $US17,000.

‘You somehow have to make friends with uncertainty.’

Apple’s former top designer Jony Ive

But over two days with him earlier in the summer, it became apparent that he has become more relaxed, even as the range of projects he tackles explodes.

“What I’m learning is to trust, more than ever, my intuition,” Ive said. “That’s the thing that I’m most excited about.”

When Ive first considered leaving Apple, he turned to his friend Marc Newson for advice. The Australian-born industrial designer, who joined Apple in 2014 to work on the Apple Watch, had spent his career at an independent design firm with work that ranged from luxury yachts and surfboards to Louis Vuitton luggage and vibrators. Newson suggested that they start a creative collective to work on projects.

Recalling those early conversations, Newson said the goal was to leave behind the grind and rigor of Apple. “The freedom was the idea,” Newson said.

Over five years, Ive and Newson hired architects, graphic designers, writers and a cinematic special effects developer who work across three areas: work for the love of it, which they do without pay; work for clients, which includes Airbnb and Ferrari; and work for themselves, which includes the building renovation.

He and Newson hope the renovation, which is scheduled for completion in late 2025, draws others to the area. Several firms have already followed, including Emerson Collective, which was founded by Laurene Powell Jobs, and Thrive Capital, the venture capital firm with ties to OpenAI.

“There’s a counterintuitive opportunity to prove people wrong” about San Francisco, Newson said.

Though Ive is optimistic about their work and enthusiastic that it could make his investments in Jackson Square worthwhile, he is uneasy about the future. It is only natural for him to be afraid that he spent too much money on property or worry that his startup could fail.

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But seated on a plush cream couch near LoveFrom’s model of Jackson Square, he said that his philosophy was not to let success be determined by a number. Judging a real estate purchase or a new device by its return on investment would miss the point. Life’s most important decisions require leaps into the unknown.

“You somehow have to make friends with uncertainty,” he said. It was a very un-Apple-like view of the world.