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7 design lessons from Silicon Valley’s most important failure

From Tony Fadell to Megan Smith, six influential members of the 1990s startup General Magic share their advice for designers, technologists, and entrepreneurs.

7 design lessons from Silicon Valley’s most important failure
In 1992, Megan Smith with the “walkabout” prototype, which later became the cell phone in a scene from General Magic–A Film by Sarah Kerruish and Matt Maude. [Photo: courtesy Spellbound Productions]

The head of AI at Apple. The founder of Nest. The head of Google’s speech recognition. The CTO of Twitter. The CTO and cofounder of LinkedIn. The VP of technology at Apple. They all have one thing in common: In the early 1990s, they worked at a small Silicon Valley startup you’ve never heard of.

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In 1990, a company called General Magic spun off of Apple with members of the original Macintosh team as cofounders. Their goal was to create a mobile computing device that would connect everyone in the world. It was a radical idea: What if everyone had a personal communicator, a computer that went with them everywhere and that they used to run their lives? Over the next few years, a group of talented engineers and designers worked to create a handheld device and a network to connect them, building touch screens, apps, and even emojis for their platform in the process. But this was before the internet. People didn’t understand what they would use such a device for–and no one bought it. The company eventually went bankrupt.

Of course, the vision behind General Magic did come to be–more than a decade later, in the form of the iPhone, and then the open-source Android operating system. The company also birthed the careers of countless tech industry heavyweights. In fact, two of the chief architects of each mobile operating system, which make up 99% of all phones on the planet today, sat 15 feet away from each other when they were both lowly engineers at General Magic.

The story of General Magic’s rise and fall–and its legacy–is now the subject of an eponymous feature-length documentary. After premiering at New York City’s Tribeca Film Festival in February, today the documentary has its Silicon Valley premiere, where more than 100 former General Magicians, as they’re called, will be in attendance.

Fast Company spoke to six of the company’s most famous graduates, from Tony Fadell, who co-invented the iPhone, to Megan Smith, who was the first female CTO of the United States under Obama, about what they learned from surviving tech’s most influential failed startup. This is their advice to designers, technologists, and entrepreneurs aspiring to change technology today.

In 1992, Marc Porat holds up the design of what is now the iPhone in a scene from General Magic–A Film by Sarah Kerruish and Matt Maude. [Photo: courtesy of Spellbound Productions]

Don’t be afraid to invent a new paradigm

“General Magic was all about thinking from first principles about solving problems based on user needs, just fundamentally. And you needed to invent a whole bunch of technology to do that.

“This was before the web. It was a fictional idea, that you could have a device that was portable and connected to other devices. It was radical.

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“It was the best-funded, the most attractive, craziest project in Silicon Valley back then. The thing that defined it was just no limits. With hindsight, it was this crazy prototype that wanted to do everything, both the network service and the device itself. Each piece was incredibly ambitious: email, messaging, chat, touch screens, all at the same time. They were inventing things from whole cloth. They were powering through walls. The limit was physics.

“Solve the real user problem even if that means inventing something that does not exist yet. This is how we got the mouse, the touch screen, and email addresses. All of these things were trying to make technology more accessible to people.” —John Giannandrea, head of AI at Apple, engineer at General Magic

But make sure you tackle it in bite-sized pieces

“We were doing too much. We kept adding, becoming more and more ambitious. I would say that’s the lesson. The temptation always to make something more inclusive, to make it more powerful, to make it better, to do more–that temptation is overwhelming, especially for the founding team because they have such grand visions. The fact that you have a grand vision is wonderful. But try to digest it in bite-sized pieces. You can envision it, but you have to do the implementation in increments. You can’t do too much. That’s where the magic comes in for creating something successful–that mix of key elements and functionalities that is going to be so compelling and create that feeling of delight in the customer without putting it all in, all at the same time.

“If you have a bunch of self-motivated and smart people and you put them together they’ll produce something incredible. But you can’t minimize the importance of management. It’s a dirty word. It’s prosaic. It’s not vision. It’s not dream. It’s not technological excellence. But unfortunately, it makes all the difference.” —Joanna Hoffman, part of the original Macintosh team, head of marketing at General Magic

Joanna Hoffman. [Photo: courtesy Spellbound Productions]

Never forget that the most important person in the room is the user

“Put the user first. There’s all kinds of opportunity to put other things before the user, like profitability, or some strategic goal you have. In the long term, you have to put the user first. They’re the ones who you’re doing what you’re doing it for. That’s my North Star. Even better, try to work on a project that you yourself want more than anything else in the world. If you are the ideal user, it’s natural to see what the user wants. It’s easy to work on things you’d never consider using, but it’s more advantageous if you’re working on something that is substantially for you.” —Andy Hertzfeld, software “wizard,” lead software architect on the Macintosh, cofounder at General Magic

“Really understand your audience. We were designing it for us, the tech geeks. It had a nice user interface–we wanted it, but we didn’t realize that society didn’t need it yet.” Tony Fadell, inventor of the iPod, co-inventor of the iPhone, founder and former CEO of Nest, principal at Future Shape, hardware and software engineer at General Magic

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Embrace criticism–it makes your ideas sharper

“There’s a value to being pushed on by smart people. Whenever you’re up against a really sharp, harsh critic who’s dissing your work and making you feel like a little worm, there’s something useful there because you’re getting free consulting from a smart person who’s forcing you to get to the essence of what you’re really thinking, saying, feeling. Without that pressure, your ideas aren’t as sharp.

“The thing about visionaries is that they see things other people don’t see clearly and they hear things that other people don’t. There’s a fine line between being a visionary and seeing something people don’t see and being considered nuts. There’s a lot of pushback, which could create self-doubt. In my case it created stronger affirmation.

“Don’t be disheartened by rejections. Reframe them and they’re free consulting that helps you get to the essence.” —Marc Porat, CEO and cofounder at General Magic

Learn from those with mastery

“There’s extraordinary people with great accomplishments that you can learn from. Make sure you think about apprentice, journey, mastery–that sort of path. There are master entrepreneurs that have built extraordinary things . . . If you get to work with them, you get practice in their ways.

“The [General Magic] group had a lot of experience making many kinds of products. All of us who were younger in our careers got that apprentice opportunity. You should be on the lookout for people like that. You can look for not only what you want to work on, but amazing colleagues to learn from.” Megan Smith, first female CTO of the United States, former VP at Google, founder and CEO of Shift7, mechanical engineer at General Magic

Be a pessimistic optimist–and never give up hope

“Right now we’re pushing hard on self-driving cars, on AI, on synthetic genomics. All of these things will happen. But they’ll take longer. There’ll be more questions. We’re going to go through the trough of disillusionment. But you need people pushing, blindly or informed, to keep progress going. To me it’s just evolution at work. We’re evolving more rapidly than ever.

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“I’m a pessimistic optimist or a cautious optimist. You always have to have hope.” —Tony Fadell

Own tech’s failures and fight to fix them

“Just the thought that work I did getting computers into the hands of everyone is now used to undermine freedom and democracy is deeply embarrassing and troubling. In general in the industry, people are giving second thoughts to all that. Hopefully they’re doing it in a clear, transparent, and honest way. Facebook leaves something to be desired in some ways, the way they trickle truth, admitting the minimum they can at the time.” —Andy Hertzfeld

“Silicon Valley has gone a long way away from remembering to include everyone at the design table. This extraordinary challenge that exists in humanity, that accelerates some talent and decelerates others–that’s one of our greatest challenges, to bring everyone to the design table, and figure out: How do we reduce the negative use of technology?

“What I loved about the mentors we had at General Magic: They had extraordinary values. Even then we made mistakes. I personally loved having the opportunity to work with this extraordinary team that had created the Mac, which empowered so many people to be more connected. But we also see the challenges of the technology, to protect our core values around equality, around democracy.

“I was working on physical models. [Andy Herzfeld] said, make sure you make the camera. He held [the device] up as if he was clicking and said, ‘People are going to take pictures and send them all over the world.” Instagram! This is 1992. And yet today when I take a photograph, if there’s a person of color I have to adjust the light balance, because this camera is racist on my phone. [The tech is] awesome, but it’s unfair that one group gets the default and one group has to be adjusted. That’s wrong. As soon as we find that we have to mitigate.” —Megan Smith

“If you want to make any kind of change, you have to take risks. But you can’t move fast and break things, and you can’t have analysis paralysis. As a designer, or engineer, or business person, we have to move fast. When you know you see something wrong, it should be a red flag. Take the risks and move. You will make mistakes. Your job is to fix them as quickly as possible, and design them out, ideally.

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“Sometimes you can’t understand the risks. Now we see it. Don’t blame others–take it on. Make some change.” Tony Fadell

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About the author

Katharine Schwab is an associate editor based in New York who covers technology, design, and culture.

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