Mackey Saturday has been a designer as long as he can remember. And he’s been a perfectionist from before he can even remember.

His parents tell stories of a young Mackey sitting at their little kitchen table drawing a single fish for hours on end—colouring in every single scale, one by one, before freaking out, destroying the drawing, and throwing it in the trash.

When this started happening more and more frequently, his answer to his parents was always, “It doesn’t look like what’s in my head.”

Now, for most designers, and artists alike, this is a common story: The mental vision is so strong, but the skills aren’t quite there, causing us to push ourselves further and further. To practice longer and harder. To make what’s imaginary, real.

The fish story serves as the perfect metaphor for one of the biggest (at least exposure-wise) design jobs of Mackey’s life: When he contacted a growing startup called Instagram about their design needs.

By now, I’m sure most of your reading this either use Instagram on a regular basis, or at least know what it is. But back in 2011, significantly fewer people were using the app.

But they were growing. And like all good entrepreneurs, Mike Krieger and Kevin Systrom, the co-founders of Instagram, planned on keeping that growth going. At this point in time, the two had been the driving forces behind Instagram. They didn’t even have a designer on the team, and Kevin had hacked together the original logo using an open-sourced typeface called Billabong. At the time, the product was what mattered. For their logo, they just needed something good enough.

But good enough isn’t enough when you’re going after a billion dollar buyout.

Enter Mackey Saturday.

We’re still in 2011 here and Mackey is home in Denver and comes across a listing for someone to help with design at Instagram. He knows the company and he’s heading to San Francisco anyways, so he fires off an email:

Mackey “I just wrote an email to Kevin and said, ‘Hey, would you want to meet up and get coffee or something?’ It wasn’t necessarily directed at the design position or anything. I just thought was he was doing was really cool and I wanted to get to know him.”

Sure enough, Kevin agrees. They set the date and location (a coffee shop in San Francisco), and Mackey rolls up as he would to most meetings: baseball hat, t-shirt, and his skateboard.

Mackey “I get there and I was like, should I have been more formal? I wasn’t looking at this as an interview…”

Neither was Kevin.

Over coffee, Kevin shares more about Instagram—their vision and where they’re going. At the end of the meeting, they’ve roughly established that should the need arise to do a redesign, Mackey might be the right fit. But that’s about it. They both go their separate ways and back to their separate lives.

Fast forward a year and Mackey drops his acquaintance Kevin a quick email:

Mackey “I think it must have been close to a year. I checked up one day—just sent an email like you would to anybody: ‘Hey, how’re you doing? You surviving?’ And he was like, ‘We need to do this thing’.”

And in typical startup fashion they just got to work. There was no pitch. No proposal. Mackey was just hired.

With Instagram gaining millions of users a month at this point, they started out by defining the goals of the redesign:

Mackey “Ok let’s make something we can own. All of the basic identity standards. Let’s make something that can last. Let’s make something that is us and will be recognized forever. We wanted to give it that spot against those long-standing logo types like Coca-Cola.”

And of course they had to address some of the issues that the previous logo was causing:

Mackey “It looked like it said Jinstigram. I think there was even an article when we revealed the logo that said ‘Instagram becomes Instagram instead of Jinstigram’. It was obvious they had just taken these letters and pushed them all together because the way that the font worked, it wasn’t designed specifically for those letters to interact and so we wanted to have this free-flowing script.

We wanted it to look intentional. Because, yeah in the original one you had an “I” all by itself, an “n” that wasn’t connected, an “s” that wasn’t connected. And then you had “tag” in the middle that was all connected. And then “ram”. So it was like I N S TAG RAM. And the descender on the “g” was super low. So at one point they had used like a distressed filter to just erase the bottom of the g because it had no home. It had no place to go. Otherwise Instagram itself would have to become so small. It was always this battle of how do we have this descender not just hanging out all by its poor self and ruining this UI.”

“One of the hardest things to do was the ‘S’ and that’s the only letter that is a completely different style than it was originally. So making that decision was a big decision and a great challenge because linking the “S” to the “T” is hard to figure out. No one really thinks about that, but it was very hard.”

So Mackey’s hard at work trying to create a logo that pays homage to the original but is timeless and will work with all of the different use cases. Week after week he’s checking in with Kevin on Monday mornings, showing the progress that’s been made. Then he gets an e-mail from Kevin that says:

Mackey “Hey, can we skip next week because we’re going to launch Android? The next Sunday, I get this email that says Urgent. And I thought that the lawyers just needed to double-check some things, and so I go into my studio and see the news…”

Facebook had acquired Instagram for $1bn.

And they were still using their hacked-together logo.

For a company now in the billion-dollar club and navigating an acquisition by one of the largest technology companies in the world, a logo redesign usually hits the back burner. And so, they hit pause, and Mackey had to wait. One month. Two months. Three months… It wasn’t until the end of the year that things slowed down enough for them to pick back up:

“We sat back down together and we just sort of hammered out the remaining details and we were able to put them up on the wall and everyone looked at them.

“Kevin was always an active part of this process, which was very important because he was the decision-maker and he was always there. He was always also never asserting himself. He wasn’t trying to do something that he couldn’t do. He was just always in the meetings, ready to give the feedback that needed to be given, but also would overly emphasize the trust that he had in me and this team because this is what we do well.

“So yes, he had an opinion and he knew things that I didn’t know, especially about their future and where this would need to be used, but he by no means ever tried to design this thing or ever thought it was some extension of his life or whatever.”

“We had solved it to the point where it felt right to him and we could still go in and do our tiny tweaks.”

There was just one last step. Mr. Zuckerberg himself had to sign off on it.

“I was never really worried. I believed that he had that same mentality of ‘I really trust the people that do this well that they will do this well and that we’re only hiring the appropriate people for these tasks’.

“And so, when we were able to put it in front of him and he had the same reaction that most of the public had in that he could barely tell that we changed it (even though we changed everything). Because it kept that equity that was there. It kept that emotional piece and then a couple months later they dropped it at the end of a video and stuck it in the app. And there it was.”

And so, a couple years in the making, suddenly the Instagram re-design was out.

From a chance encounter, Mackey became the man behind one of the world’s most-viewed logos, solidifying the Instagram brand for years to come.

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