The Many Stories Of Instagram’s Billionaire Founder

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The Many Stories Of Instagram’s Billionaire Founder

Words by Mr Dan Rookwood | Photography by Mr Brad Torchia | Styling by Ms Gaelle Paul

18 October 2017

Mr Kevin Systrom, Silicon Valley’s snappiest CEO, is cleaning up the internet with automated kindness.

It happens to be a landmark day at Instagram when MR PORTER visits the company’s global HQ to interview its co-founder Mr Kevin Systrom. Preparations – including the construction of a selfie booth made of balloons – are underway at its Silicon Valley offices for an all-staff party to celebrate its seventh birthday and 800 millionth monthly user.

The company’s co-founders, Messrs Kevin Systrom and Mike Krieger, who still work together, are in a reflective mood. Each has posted images on their personal Instagram feeds from those early days and nights in October 2010 when they were working in shifts around the clock to keep their fledging app up and running. The images are grainy. “It was a terrible filter, it’s a terrible photo,” says Mr Systrom of his picture of Mr Krieger in a hoodie sitting in a small office in front of several screens. “I blame it on the phone, it was the phone’s fault.” He has since deleted the post from his carefully curated @kevin feed, though @mikeyk has left his up.

Instagram’s success was instantaneous and the speed of its growth a white-knuckle ride. Apple had just launched the iPhone 4, the first smartphone with a camera that could compete with a point and shoot. Instagram’s launch was perfectly timed: 25,000 people downloaded the free app in its first 24 hours. Alarms went off on the co-founders’ iPhones every time the servers were overloaded. To this day, Mr Systrom has a Pavlovian response to that alarm – one of instant anxiety. Within four months, they hit a million registered users. Within 18 months, they sold the company – which had only 13 employees at the time and hadn’t made a single cent in revenue – to Facebook for a headline-making $1bn in cash and stock. Mr Systrom, then 26, personally pocketed a reported $400m and retained his position as CEO. People thought Facebook’s founder Mr Mark Zuckerberg had lost his mind – it is understood he doubled a rival offer on the table from Twitter. Turns out, he got a bargain: in December 2014, Citigroup valued Instagram at $35bn. Last year, Forbes estimated it had shot up to $50bn.

Instagram had a false start as a failed location-based networking app called Burbn before Mr Systrom pivoted (to use the Silicon Valley term) into creating a photo-sharing app with filters. The idea came to him while on holiday in Mexico with his wife (then his girlfriend) Nicole, who said she wished she could use something like Photoshop to enhance her mediocre photographs. It was a light bulb moment. Mr Systrom took himself off to a hammock with his laptop and by the end of the day had designed the X-Pro II filter. The very first Instagram post was a shot of Nicole’s foot, a stray dog and a beachside taco stand.

We need to talk about Kevin. Mr Systrom grew up in a small town 25 miles west of Boston, the son of Douglas, who worked in human resources for a corporate company, and Diane, a forward-thinking tech executive who worked in startups such as the vehicle-sharing app Zipcar long before startups were a thing. He has a younger sister, Kate, who works in San Francisco for Pinterest. A talented programmer and amateur photographer, when Mr Systrom was in his final year at Stanford (a conveyor belt for Silicon Valley entrepreneurs), he met Mr Zuckerberg who was on campus promoting “The Facebook”, which was then in its infancy as a networking site for Ivy League schools. Mr Systrom politely declined the offer of a job, with stock options that would later have been worth millions (according to Forbes), having been advised that Facebook was “just a fad”.

The next time he saw Mr Zuckerberg was when he served him coffee as a barista. Mr Systrom graduated in 2006 with a BSc in management science and engineering and worked for Google for a couple of years as well as at a company called Odeo, where he shared desk space with a young engineer called Mr Jack Dorsey, who went on to co-found Twitter. They became friends but that didn’t help Mr Dorsey when he tabled his reported $525m bid for Instagram in 2012. Mr Dorsey hasn’t posted to his @jack feed since.

At 6ft 5in, Mr Systrom, now 33, is instantly recognisable when he strides into Instagram’s lobby on a Menlo Park technology estate in the heart of Silicon Valley, 30 miles south of San Francisco. He’s now a billionaire himself, but he doesn’t seem to play the alpha male like some of his fellow tech titan heavyweights. He doesn’t even have a corner office: he sits at the same kind of desk as everyone else alongside his team in a smart open-plan office. There are a couple of potted plants next to his Mac desktop, which is propped up by a few books, one of which is Another Man: Men’s Style Stories.

He likes fashion. A founding member of MR PORTER’s Style Council, Mr Systrom has a reputation as the best-dressed CEO in Silicon Valley. “I’m glad I have you all fooled!” he winks. Admittedly this is not a hard competition to win: the sartorial bar is famously set pretty low in the tech community. However, Mr Systrom is not as buttoned up as he used to be and arrives at the office today dressed casually in a short-sleeved blue gingham button-down and navy trousers (both Gucci) with white Common Projects sneakers. “You’re 33 once, and you only really get the chance to dress like a 33-year-old once, so you might as well embrace that while you can,” he explains. “Also, I think in Silicon Valley, there’s a bit of an anti-traditionalist ethos, which is like, no one wants people to walk into the office with a suit and tie. That’s the anti-Silicon Valley thing.”

He spends a long time looking through the rail of clothes for his MR PORTER shoot, trying things on, and inspecting the Officine Panerai watches that are set out in one of the conference rooms. Mr Systrom wears a Rolex day to day, though he says the rest of his collection is modest: Mondaine, Uniform Wares, Shinola.

He used to follow quite a few fashion bloggers and influencers – but no longer. “I find the whole influencer world to be a bit unattainable when you’re sitting in an office trying to get work done, and you’re like, ‘Oh, well they’re in Greece now, and then they’re in Capri.’ I tend to follow lifestyle accounts, architecture accounts, interior design accounts that I think inspire a little bit more creativity and a little bit less jealousy.”

Although he hardly stopped when Instagram was a startup, he now makes sure he gets plenty of sleep. He likes to cite life lessons from fellow tech entrepreneurs and recounts some advice from Mr Jeff Bezos, founder and CEO of Amazon, who reasons that executives should prioritise sleep. It comes down to a choice between making more decisions because you’re awake for longer or making better decisions because you’re well-rested. Sometimes he gets nine hours sleep. That looks set to change soon, though. Mr Systrom and Nicole, a fellow Stanford graduate and CEO (founder of clean-energy investment firm Sutro) are expecting their first child, a daughter, in January.

Until then, Mr Systrom’s main priority is looking after his first baby, Instagram, and its latest feature, Stories – a full-screen stream of personalised stills and videos designed to be used in a more instant and unfiltered fashion to the main feed. This starts from the moment he wakes each day. “My morning ritual is the alarm goes off, I blurrily look at the phone, and I tap that first story and I just sit for 10 minutes while they all go by. I’ll often wake up to the loud blaring of videos, and I’ll look over and [Nicole’s] watching Stories. She’ll punch me in the arm and be like, ‘Why did you do this [launch Stories]? I just spend all my time on it.”

According to Instagram’s own statistics, users under the age of 25 spend an average of 32 minutes a day on Instagram; those 25 and older are losing 24 minutes to the endless scroller-vortex. It’s all meme, meme, meme. “I’m dragging up the averages,” says Mr Systrom. “I’m pretty obsessed, I’m on it pretty nonstop.”

How does he respond to the charge that he has deliberately made Instagram addictive in order to appeal to advertisers? “I think to apply a single label of good or bad for something like social media or phones misses all the nuance. Everything has its limits. If you exercise too much, it’s very unhealthy. If you eat too much, it’s very unhealthy. Everything in moderation.”

Mr Systrom himself is the picture of health. He has become “weirdly serious” about cycling. From 7.30am until 8.30am each morning, he rides a road bike, which is hooked up to a stationary resistance computer game in his house. It’s called Zwift and he races people online in a 3D world with the computer controlling the resistance. “It’s the dorkiest thing you’ve ever seen,” he says. He claims to burn 1,500 calories each morning. No wonder he’s so svelte. His jawline is noticeably chiseled these days.

He’s even more obsessive about coffee than he is about cycling. He opened a branch of his favourite Bay Area coffee shop, Blue Bottle Coffee, on the ground floor of Instagram’s HQ. “At Instagram, we embrace people being the best in the world at their thing.”

Some guys are into cars; Mr Systrom is into espresso machines. A trained barista, he makes a serious post-workout coffee at home. There’s no popping a Nespresso pod and pressing a button. “I have my own beans that I get from [Blue Bottle], and it’s very important that they’re roasted on a certain date, because you’re supposed to use them four days after, that’s their peak point. I can always get new beans, and I have a special machine for it and a scale that reads out the extraction by the second, so you get a graph of the espresso extraction.”

Mr Systrom, it should be noted, is a triple-shot investor in Blue Bottle (stumping up in 2012, 2014 and 2015), which just last month sold a 68 per cent stake to Nestlé for $500m. Who knows how much Systrom made out of that but we can safely presume it was seriously good extraction. Wake up and smell the coffers.

While Mr Systrom is having his photograph taken, I grab a cappuccino and wander around the blond wood and brushed steel offices until I am told off for snapping Stories in a restricted area. The place feels like a movie set. Young people (I don’t see anyone over the age of 35), a surprising number of whom are wearing Instagram logo T-shirts, clutch MacBook Pros to their chests as they scurry in and out of glass-fronted meeting rooms called things like “Simplicity Matters” and “Delightful Lounge”. There are on-message motivational posters dotted about to get everyone aligned in a collective thumbs-up “like”, saying such things as “Experiences speak louder than words” and “Relationships make the world go round – Yass!”

Instagram’s company culture is something Mr Systrom was careful to maintain when joining forces with Facebook. “Silicon Valley is typically a hacker culture, this ethos of sitting in a garage in hoodies and just getting it done,” he says. “Actually, if you look around Facebook [HQ] sometimes, you’ll see old posters that say, ‘Done is better than perfect’. When we joined Facebook, it was funny, because we have a similar culture, but that one poster stood out as potentially different, because at Instagram we tended to be more ‘Perfect is better than done’. We moved a lot more slowly. Maybe by being at Facebook, we’ve helped them be a bit more crafted, and they’ve helped us move faster. But the details matter and whatever you put out in the world should be a reflection of how much you value it.”

Mr Systrom meets Mr Zuckerberg each week, but is pretty much left to run Instagram as an independent entity under the auspices of its parent company. So long as they hit their numbers. “We’re doing just fine,” he says. Instagram recently announced it now has two million monthly advertisers.

As CEO, Mr Systrom focuses on what he calls “the big rocks” – the high impact, high-cost decisions that are extremely important for the future of the company. For example, last year saw a controversial “Systrom reboot” to change the timeline from appearing in chronological order in favour of one dictated by an algorithm, so that the powers that be can better control what they feed you – a diet rich with added ads.

For all the mega-influencers on Instagram (Ms Selena Gomez tops the list at 128 million followers), the one who arguably wields the most power is Mr Systrom himself, the leader of a global community of 800 million – 2.5 times the population of the US. And he gets to write its constitution.

To his credit, Mr Systrom is trying hard to use his superpowers for good and says he feels a personal responsibility to make the world a safer place online. If Ms Kim Kardashian tried to break the internet, Mr Systrom is trying to fix it. With relentless kindness.

In the early days, he and Mr Krieger would personally delete unpleasant comments and ban abusive users. Now he has automated the system, teaching machines to detect and delete them. “We have this whole movement we call internally ‘Technology for Kindness,” he explains. “What we realised is being so big, we actually have a unique place in the world to increase kindness.”

In his attempt to create this idealised “newtopia”, he has been described by Wired magazine as a “benevolent dictator”. He’s not curbing free speech, he says. “We’re getting rid of the worst bottom one per cent. Think about it as cleaning up trash on the side of the highway. We’re just trying to keep people generally kind in the world. If we can just tip things one per cent, and if that compounds over 30 years, then the results are massive.”

Mr Systrom also believes Instagram can save lives. “If you’re searching certain hashtags or someone flags, one of your followers sees you post in despair, they can actually flag your post and say ‘Hey, I think this person needs help’. And we can connect that person with resources.” Has Instagram prevented any suicides that he knows of? “You know, for confidentiality reasons, I’m sure they don’t share that, but I’ve got to imagine it has.”

A cynic might suggest that while these changes are laudable, they are largely commercially driven. Companies are more likely to advertise in places where people respond positively and celebrities only want to engage with fans. But Mr Systrom insists his motives are pure. He’s trying to take responsibility, set an example and build a legacy all at the same time.

Will he open-source the machine learning technology, give up the patents just as Tesla founder Mr Elon Musk did with his electric car, in order to further the mission? “There’s a lot of talk about copying in Silicon Valley,” he says. “This is the one thing I hope every single other company copies, because the world would be better off for it.”