The Facebook executive invites us to his house in Joshua Tree to see his collection of vintage watches .

Aside from founder Mr Mark Zuckerberg, Mr Matt Jacobson is now Facebook’s longest-serving employee. He was hire number eight, back in 2005. Then 44, Mr Jacobson had recently left a top marketing job at surf brand Quiksilver and was looking for the next big wave to ride. He took a chance on Mr Zuckerberg’s fledgling startup, which couldn’t afford to pay him. He agreed to work for equity instead. From Quiksilver to solid gold.

Hear all that and you might make a couple of assumptions. First, he’s done more than all right for himself financially. Second, he probably wears a hoodie and ironic slogan T-shirt every day. You would be half right. Mr Jacobson is considered the best dressed exec in tech, always immaculately turned out in a suit and tie worn with one of his prized collection of vintage watches. His “grown man style” (he has a blog of the same name) sticks out on campus. “I get much better service [in restaurants] when I’m wearing a tie than when I’m not,” he says.

As a public face of the company, it is part of Mr Jacobson’s job to connect the sometimes disparate worlds of Silicon Valley and Hollywood and build partnerships. He lives in the Southern Californian surf town of Manhattan Beach, where he grew up.

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Now 57, Mr Jacobson still surfs most days when at home. A few years ago, he and some like-minded friends acquired Birdwell, a famous US surf brand whose indestructible board shorts he has worn all his life. He and his interior designer wife, Ms Kristopher Dukes, live in a stunning house that couldn’t be closer to the beach, designed by revered SoCal architect Mr Ray Kappe. Ms Dukes worked with Mr Kappe to sensitively remodel the decor when they bought the place in 2010.

The couple are design obsessives and several years ago they bought a prototype prefab in Desert Hot Springs, designed by Los Angeles architects Marmol Radziner. It was while staying there four years ago during Modernism Week, an annual festival that celebrates the iconic architecture of nearby Palm Springs and its surroundings, that Ms Dukes heard the nearby Kellogg house had come on the market for the first time. Mr Kappe, who has become a friend, was staying with them and he was curious to look around it. Mr Jacobson was more circumspect.

“I said, ‘Listen, we don’t need another house in the desert. I’m not going to do that. You guys, if you want to go see it, I’ll drive you out there, we’ll go look.’ And Ray, who is not a very effusive person – he’s a very thoughtful, quiet man, he just turned 90 – came running down the hill and said, ‘You have to come see the house. You have to buy this house.’ Which was so out of character for him. So then I came and saw it and said, ‘Wow, this is mind-blowing.’ The level of detail and how this house is put together and how it’s built is just... Every time I’m here, I find different magical parts of it.”

The house was designed and built by the eccentric architect Mr Kendrick Bangs Kellogg for Ms Bev Doolittle and her husband, Mr Jay Doolittle. She is a commercially if not critically successful artist; he is her agent. Design began in 1988 and the main structure was finished in 1993. Mr Kellogg then brought in Mr John Vugrin, an interior designer and master craftsman to custom carve, and weld, every detail of the house on site. It took for ever. The Doolittles didn’t move in until 2002, but Mr Vugarin continued to tinker away with his Gaudí-esque flourishes until the Dootlittles downsized in 2014. The house surely cost far more to build than the $3m asking price.

“It’s bananas!” says Mr Jacobson, conducting a house tour as if it’s a museum, which, in a way, it is. “I mean, if you have unlimited time and money, you can say to an architect, ‘Just do whatever you want.’ That’s what these people did.”

Technically wall-less, the house comprises 26 cantilevered concrete columns, each fanning out at the top and overlapping to form the roof line. Between the columns, invisible at certain angles, light streams in. At night the stars are visible from the sitting room and from the master bedroom. The National Park’s boulders have been incorporated into the five-level structure. From inside, it feels like you are on the bridge of a spaceship looking out at a lunar landscape.

Mr Jacobson describes himself as a “custodian” of the house. He and his wife intend to preserve it as a work of art and make no drastic alterations.

This sums up the way Mr Jacobson approaches all the things he collects, whether houses, vintage German cars, mid-century modern furniture, Leica cameras or his prized watches (more of which anon). “I’ve put together nice collections of stuff,” he says casually. “I feel like I’m just kind of hanging onto them for this moment in time. They aren’t the ultimate collections, but they’re things that are kind of unrestored. Original cars, watches that have a story. I generally don’t buy things that have been restored or refinished. I like natural patina.”

The word “curated” is an over-used one these days, but Mr Jacobson operates a strict one-in, one-out policy when it comes to his collectibles. “My mom and dad were always collectors, but I think I learned and appreciated curation pretty early,” he says. “I didn’t want to be a massive acquirer or hoarder. I try to find really good examples of things, not have a lot of them. It’s kind of like the Japanese denim attitude. Have one great pair and you don’t need nine mediocre pairs. Anything I find has got to be better than something I already have for me to get it. You don’t want to have that drawer of stuff that you don’t use, cars that you don’t drive, or watches you don’t wear.”

Mr Jacobson owns 14 watches, however. “Two are in the departure lounge,” waiting to be sold. He keeps his collection to just 12, “which sounds like a lot if you’re not into watches, but believe me, this is nothing compared to most collectors”. He stores them in two utilitarian Pelican cases, specially modified to hold six apiece.

The collection is never complete. It can always be improved upon and he is always looking. “You cannot out-Google me,” he says. He finds watches all over the place – at vintage shows, on eBay and increasingly on Instagram. “I’ve been very lucky to have worked on luxury on Instagram. And it’s so great to see the watch brands embrace the platform, brands like Rolex, doing amazing stuff on Instagram, and I think the general interest in watches, there’s so much knowledge, and there’s so much stuff happening with watches on Instagram. And you’ll talk to dealers, they’re selling most of their watches on Instagram.

“My real preference always is to get watches that haven’t gone through dealers’ hands,” he says. “Even though I do like and respect dealers, it’s always more interesting to me to find the original owner or the owner’s family. I’ve been doing this for a long time and I try to buy things that are beautiful, and that appeal to me first, rather than because there’s an extreme level of rarity around it. It needs to have a story. It’s like fine art. You don’t buy art to speculate, because you’ll get crushed doing that. You have to buy what you love.”

With that in mind, here are a few of Mr Jacobson’s favourite timepieces.

Rolex Day-Date Ref 1802

“This is a really pretty watch with a smooth bezel oyster band with an enamel Stella dial in coral. Those enamel dials were made by Rolex specifically for the Middle East market and they were not embraced. Many were removed from watches and discarded. But they were just magical colours, you know, blue and yellow and green. I love the Rolex Day-Date, which is about as complicated as any Rolex watch gets. They’re not really big on complications. With a smooth bezel, rather than a fluted bezel and an oyster band, that’s a riveted oyster band, it’s just a beautiful combination. It’s late 1970s. It’s hard to get the exact date unless you have papers, but you can look at the serial numbers and you can get kind of close. I had a white-gold version of this watch with the coral dial, and then I found this one, and I sold the white-gold one because I like this version better. That coral dial is so pretty with the yellow gold.”

Rolex Submariner Ref 1680

“This is a Submariner that had spent all of its life in South America. The original owner was a sailor. This watch started out with a blue dial and blue bezel, but because of the intense sunlight, the dial has turned brown. They call these tropical dials, when the colour on the dial coating changes due to the sun’s effect. You can see between eight and nine a little touch of the blue. I really love tropical-dial watches because companies like Rolex that build to the highest standard, the fact that something kind of got through the process and 50 years later, this dial has turned from blue to brown, I think is pretty great. This watch is on a bund strap, which has become really popular lately because this is how Paul Newman wore his famous Rolex Daytona [which was auctioned last year]. A friend of mine, named Nick Gabarro, has a strap company and he is probably the best maker of shell cordovan straps. This leather is from Horween in Chicago. I’ve worn this bund strap into a great patina that I think looks just cool with that watch.”

Rolex Sea-Dweller

“This is another really amazing example of a tropical-dial watch. It started with a black dial and a black bezel insert. They call it a ghost bezel when it turns really grey like that. The luminescent pearl at 12 o’clock actually matches the patina of the markers. This is a very, very early example of a Rolex Sea-Dweller. Late 1960s. On the back, you can see it’s marked ‘patent pending’, which means this watch was made before Rolex was issued the patent on the helium escape valve, which you can see at nine o’clock on the side of the case. I think they made a little over 100 pieces that were patent-pending pieces. I had owned another Sea-Dweller, but I found this watch and sold the other one I had. It’s on an Hermès strap. A lot of collectors are like, ‘Oh, you should have it on a Rolex strap.’ But I just think it looks really cool on that Hermès. The colours are really perfect.”

Audemars Piguet Royal Oak Series A

“This is one of my absolute favourite watches, designed by a great watch designer, Gerald Genta. He is also known for the [Patek Philippe] Nautilus, which has become incredibly popular. But this is a Series A of the Royal Oak, the original series of watches. I love the way AP puts the serial number right on the back so you know what you’re getting. So it’s Series A, the first series of the watch. And the serial number is 1200. A friend of mine just got one that was an earlier serial number that was early 1973, so I figured it was probably the same, 1973, 1974. It’s also a tropical dial. It was a black waffle dial that’s turned a really pretty kind of a golden brown. It’s an amazing watch. I mean, the design! Think how crazy that watch was in the early 1970s. It’s a beautiful example, unpolished. I love the way the band is integrated into the case. It’s super comfortable to wear. I’m starting to see more interest in that watch now from collectors. There were a couple at auction. I think this is going to be a really, really big watch, the way the Nautilus 3700 became a really big collectible watch. Maybe more beautiful than the Nautilus.”

Rolex GMT Ref 1675

“I got this band just a couple of months ago. Every year, there’s the Los Angeles Pen Show, which is an international event that just happens to be in Manhattan Beach. This year, a dealer friend of mine, who I’d actually grown up with, had a watch on his stand that was on this band from the 1970s. I didn’t like the watch that was on it, but I said, ‘I have to have that band.’ These pieces are 18-carat gold and the band fit me perfectly. And I thought I have the perfect watch for it: this 18-carat Rolex GMT. It’s a classic Rolex 1675 from the early 1980s. Rolex switched from plastic crystal to sapphire crystal in 1983. So the pre-1983 plastics are, I think, more beautiful in a lot of ways. Anyway, the style of the band and the colouring reminded me of this house.”

Patek Phillippe 2526

“This is a very rare watch. But it’s very simple and just beautiful. It came from one owner, who wore it every day till he died. This is a Patek 2526 in white gold. They’re so much more common in yellow gold and pink gold. Very, very rare in white gold. It’s the first automatic Patek ever made, which makes it mid-1950s. Modern for its time, it used the company’s first automatic movement (12-600 AT) and featured a sublime double-baked enamel dial, with a slightly beige, warm tint. The white-gold example is one of supposedly only 30 made. I love the 2526 for its clean lines, modern look and underground value. It’s often mistaken for stainless steel. Most people don’t give it a second look, just as I like it.”

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