Not so long ago—at least that’s what it seems like—I would chat with him when he came to our IDEO office with his most intractable design problems. I remember seeing him in his rollerblades whizzing around the aisles of the nearby Whole Foods. I remember feeling like something momentous had just happened when he soft-launched the original iMac at a private event at Stanford. More recently, I remember how it felt like the world had stopped on its axis, that October afternoon in 2011, when I got the news that Steve Jobs was dead.

It’s been more than five years since his passing and yet: pull out your smartphone, book an Airbnb for the weekend, Slack your coworker a message, or ogle the Tesla self-driving by—and Jobs’ perfectly beveled shadow looms large. We live in the design-esteemed world that Steve Jobs ushered in. No individual has influenced the role of design in tech more, or is more responsible for raising consumer expectations for thoughtfully made products, than the late Apple cofounder.

Some of my interviewees for this project lead huge tech companies; some are rising designer founders. In both cases, time and again, Steve Jobs came up as reference point, illustration, or exemplar. He remains the most idolized modern founder and product-design obsessive.


1. Think Big

Last summer Apple sold its one billionth iPhone. One billion. Since Jobs introduced the first version a decade ago, the iPhone has gone on to become the most successful commercial product in human history. It catalyzed people’s insistence that their interactions with technology be frictionless and delightful. And the seed crystal of this grand fractal was the bottomless ambition of one young man working from his garage in Cupertino. Jobs wanted to put a dent in the universe and nothing less. He wanted to have a wildly unrealistic, era-defining impact on the world in which he lived. And he succeeded—not through sheer design sensibilities alone but by starting and running influential companies. As my friend and mentor David Kelley has said: “If the goal is to change the world, the business part changes the world faster.”

I’d like to think that’s why David eventually forgave me for leaving IDEO. Pure design wasn’t giving me the license or leverage to work on the problems I wanted to try to solve, at the scale that I wanted to solve them. So I became an entrepreneur. Today that tension has to be even greater for designers. When my 12-year old son can code and create, the most important question for product designers is no longer, “How can I build this?” Instead, as I wrote in the prior chapter, designers need to ask themselves and their cofounders the deeper question of, “Is it worth building it in the first place?” Or, said another way, “Is it going to matter? Is it going to address a real problem or opportunity in the world?”

It hadn’t dawned on Joe Gebbia, who had dreams of becoming a painter, that the objects in the world were acts of design until he discovered industrial design at RISD. “I became very intrigued and said to myself, ‘I would much rather apply creativity to solving problems and improving people’s lives than improving the state of the art world.’” Similarly, talking about the millions of people who use Pinterest every day, Evan Sharp said, “[I]t’s hard to argue against scale if you’re talking about positive social impact….I’ve lost a little bit of patience with products that aren’t designed to have a really large reach.”

That’s not to suggest you snort a line of coke laced with delusions of grandeur and then start nude-practicing your TED Talk in the mirror. The first step is always to find the right opportunity to work on—one that you care deeply about even if it doesn’t seem like it’s going to change everything forever and transfigure you into a living god. Be open and prepared to scale your modest solution into a larger vision.

If the goal is to change the world, the business part changes the world faster.

David Kelley

Take the example of Nate Weiner, who in 2007 got tired of emailing himself article links to read later. So, in a night, he taught himself to make a Firefox extension and banged out a little plug-in that allowed him to Read It Later, as he would come to call the product. It turned out that a lot of people had the same problem and, much to Nate’s surprise, those initial 160 lines of code became one of the most popular apps in the Apple Store, and eventually became the company Pocket.


More likely than starting off with a megalomaniacal roadmap for global conquest, this is the typical journey of a designer founder. You identify a problem and attempt to solve it as simply as possible. But once you do, you quickly realize that there’s a web of problems that your solution addresses; so, you start solving for those, too. And it continues to expand out from there:

I need to be able to save this content for later. Huh, what if millions of people did that? What would that unlock? What if it’s not just for written content but for voice and video? And then based on all the data you get, now we know what all the best content is. How can we use that to power recommendations?

When Nate retraces Pocket’s widening circle over nine years—from homemade plug-in to 10 million monthly unique users and two billion items saved—I hear someone who models the Jobsian trait for embracing expansiveness that I want to see in all designer founders.

Joe, likewise, recounted the story for me of he and his cofounders deciding to take venture funding, rather than maintain Airbnb as a lifestyle business. They did so because they realized that, given how big the travel market was, they had a once-in-a-lifetime opportunity to build something that might outlive them:

The brands we admire—Nike, Apple, Disney—have gone beyond their originators. They created these brands that in some cases define a generation. Nike in the 90s was the defining brand. Apple in the 2000s was a defining brand. We did all the math and reasoning that we could and realized that we had the chance to build one of those brands.

They decided to “swing for the fences,” not knowing whether or not it would work out.

If you have the stuff of which Jobs’ ambition was made—if you want to make a big and meaningful difference—then the surest way to create large-scale impact today is through the deft use of technology and the wise deployment of capital. Think of technology as the sword and business as the shield. The designer founder is one who can choreograph both to maximal effect. And the question of what you’re going to build—the battle to be joined—has never been more important. Creativity alone isn’t enough. Designers need to be prepared to think massive.


2. Get Smart On Business

When Jobs wasn’t yet ready to take the corporate reins of Apple, he lured John Sculley away from PepsiCo to be CEO and president. Sculley’s business experience and marketing skills freed Jobs to focus on being product czar. Until things soured and Jobs left Apple, both he and Sculley conceded that it was an amazing partnership.

If you’re a designer who’s a new entrepreneur, you’ll need to find a partner with a solid sense for business. But you’ll also need to grasp enough of it yourself in the event things go south in the relationship (See: Jobs-Sculley, 1986) and to protect yourself from being taken advantage of by unscrupulous investors. If you’re fundraising, for example, and are offered a swanky valuation—do you know what the terms for that price will cost you in the future? Do you really grok the difference between fixed and variable costs? Do you understand the fundamental financial metrics of your business?

If you’re going to live in the land of business, you need to speak the language of business. Obvious as this seems, I believe it needs stating because I know that many designers feel like business is slimy and/or alienating and/or just not fun. (After securing Pocket’s first round of venture funding, Nate Weiner found himself asking, “What’s a run rate?”) Pre-founder designers only want to be creative and make cool shit. I get that. I left the Stanford engineering Master’s program in 1995 brimming with optimism and a sense that “the best idea wins.” While I’m just as optimistic now as I was then, I can assure you, the best idea definitely does not always win.

Oracle never had the best database. They still don’t. Cisco never had the best switches and routers. They still don’t. What these companies do have is incredible marketing, distribution and sales execution. Now, I’m actually very proud of the family of VoIP phones that I helped develop for Cisco and believe it may go down in history as the last great desk phone. But truth be told, Cisco’s enterprise sales force probably could have sold as many systems had we designed the last not-so-great desk phone, instead. What I learned was a) you need both design and distribution, and b) I had a lot to learn if I wanted to start my own company.

Once upon a time, when I was applying to business school (← first line of the worst fairytale ever), I responded to the essay question “Why do you wish to earn an MBA?” by drawing the following Venn diagram:

Steve’s Venn diagram for business school, 2001.

What I was trying to convey was that, through IDEO I had lots of user-centered design experience. I had engineering training from Stanford, so I felt comfortable answering the question of “Can it be done?” But I knew that this third circle—business needs—was missing. When I left IDEO, I didn’t understand basic things like how gross margins are really calculated. I had no concept of costs that were below the line. Customer acquisition cost? What? To someone who builds stuff, you think, my costs are the parts that go into this physical object that makes a sound when I drop it on the floor. All the other costs that go into building a business were not obvious to me.

I suspected back then, and am more convinced than ever now, that entrepreneurial designers need to be thinking about all three circles in the Venn; and if they want to play a critical role in shaping the future, they have to live at the intersection. When designers ask me the best way to start earning a seat at the founders table, I tell them to get smart on sales, distribution, marketing, growth. “If you want to be leading a huge product that has lots of scale, you need to learn business,” advises Evan Sharp, who admits that he was a business innocent in Pinterest’s early days: “I got lucky. It could have been really shitty for me, and I could have built something big that I didn’t get to be part of.”

The Realm of Venture.

You don’t need to get an MBA like I did (it took me a long time to pay off my student loans!), but you can’t hide your head in renderings. Nor should you see business as just a necessary evil. IDEO’s Diego Rodriguez, for example, considers it a creative input: “I think money has historically been the missing ingredient in a lot of design conversations … [But it’s really] a liberating constraint. When you ask a customer to pay for something, it’s so different from asking, ‘What do you think?’” Not factoring in business needs, in his opinion, is like “designing bridges without gravity.”

Don’t bolt on business the way that businesses bolted on design for so many decades. And take heart in the fact that it’s far easier for designers to get up to speed on business than it is for business people to get up to speed on design. Business is a set of concepts and practical skills, a set of tools that people of every background can and have learned. And if there’s one thing designers are good at, it’s learning how to use tools. “My approach has been to embrace it,” Jesse Genet, the designer cofounder and CEO of Lumi, says,

I don’t have an MBA or a finance degree, I don’t know what someone is talking about when they say EBITDA. It feels overwhelming, but like a lot of skills, the fundamentals are not that hard…. My advice is skip the imposter syndrome, get in there and learn to enjoy it. It’s the lifeblood of your company.


3. Be an Advocate For Design

Jobs was angrily uncompromising about every atom of a product’s design. IDEO’s Jim Yurchenco—who helped to build the first Apple mouse—told me about a shouting match that he once got into with Jobs because Jobs insisted that the internal components of a product, which no consumer would ever see, needed to have a certain anodized finish. The insides! So, there’s no doubt that Jobs was a designer’s designer down to his marrow.

He derisively referred to the sales and marketing executives who dictated product decisions at incumbents like IBM and Xerox as “toner heads,” after the black powder that goes into copying machines, because their ideas about product design amounted to clueless facsimiles of what had come before.

Even though, for the health of your startup, and for your own self-interest, you need to get smart on business, never forget that the most important thing you’re bringing to the enterprise is design. Design will be the key differentiator for the great companies of the future and it’s your job to ensure that your startup will be one of those companies by being the voice for design.

I understand the exigencies of trying to keep a young company on its feet. Sometimes short-term-thinking decisions are made for the sake of revenue. But if you let other elements in the company consistently override design, then before long it won’t be part of your company’s core strategy. Case in point, one designer cofounder with whom we spoke admitted that he struggled to keep the “insidious” influence of sales culture from pushing out design as a priority at his startup. “The system is still favoring revenue … and it’s hard to account for all the little things that come up later that you don’t even think about.”

Jobs painted a depressing picture of what happens when design gets driven out of decision-making and the “toner heads” run the show.

The companies forget what it means to make great product. The product sensibilities and the product genius … gets rotted out by people running these companies who have no conception of a good product versus a bad product. They have no conception of the craftsmanship that’s required to take a good idea and turn it into a good product. And they really have no feeling in their hearts, usually, about wanting to really help the customers.


It’s the duty of the designer in the founding cohort to stop 1984 from happening to your company. “Never send a suit to do a pirate’s job,” Jobs said. Teach your organization to esteem design. Model the principles of design as a methodology for figuring out what problems to solve and how. Show your colleagues the worth that comes from putting the end user first. And strive for greatness in design even if that means making a design choice that won’t scale in the near term. A great designer cofounder will demonstrate how design can define and sometimes even save your company.

Take the story of Airbnb cofounders Joe Gebbia and Brian Chesky. In 2009, they had a problem. Rentals weren’t taking off, and the business was close to going bust. In Joe’s words, “For the first year of the business, we sat behind our computer screens trying to code our way through problems. We believed this was the dogma of how you’re supposed to solve problems in Silicon Valley.” But then, they got a kick in the ass from Paul Graham at Y Combinator, and realized that they had permission to do something that didn’t scale, but would come to make all the difference. They rented a camera, flew to New York, and worked with property owners to take high-quality photos of the properties. During the process, they also gained priceless on-the-ground insights into their users’ experiences:

We had been struggling for so long when we finally sat down with the early adopters. Talk to us—what are your issues? Oh my God, the thing we thought took two clicks, took 12! We were way wrong. It felt like this moment of enlightenment, seeing the world through their eyes. We gathered all those sources, stimuli, observations, and came back to SF, and we got smart because of it.

Joe and Brian took what they learned and made a few simple design enhancements—adding attractive images, editing the UI—and it led to an almost-immediate doubling of their weekly revenues.

Now, many thought Airbnb’s basic business model wasn’t workable. Think about it. You’re offering your home … to strangers … on the internet. Or, on the other side of the screen, you’re looking for a way to sleep … in someone else’s home … the home of a stranger you met on the internet. It sounds crazy but the design process made it work, by revealing to Joe and Brian that what they were really trying to build, at the heart of the matter, wasn’t an online rental market—it was trust, actually. Trust between the property owners and renters, and trust in the Airbnb platform. High-quality photos, smartly calibrated descriptions, and a user interface that was truly easy-to-use were some of the conclusions reached by applying design to solve the problem of building trust. “There were no sharp edges on our site,” said Joe, “The design had to communicate … that this is a trustworthy thing.”

Design pushed through people’s psychological “Stranger!” barrier, and the company’s rentals skyrocketed as a result. The philosophy at Airbnb now, is that before something goes out the door, it has to be a “minimum awesome product.” Joe explains: “For our business in particular, which is building a relationship of trust with somebody, you would never, ever use a minimum viable approach—just like minimum viability would never be the goal when it came to building a relationship with somebody in your personal life.”


4. Break Out Of The Craft Box

What Steve Jobs admired about the designer Paul Rand is telling. Jobs recruited Rand to design a brand identity for the company he started after being ousted from Apple. Rand created a 100-page brand document, which included a new company name, NeXT, and the exact angle (28°) to be used for the logo. Jobs admired him because he balanced the creative and the practical: “He really approached it as a problem that had to be solved, not an artistic challenge for its own sake.”

The stories that get told about Jobs are always of how exacting he was, down to the type of wood tables he wanted for the Apple Stores. But the underreported feature of his success was how adept he was at switching focal points and letting go of his fixation on simply the product. Jobs knew how to zoom out from his microscopic attention to detail and consider the big-picture needs of Apple, then zoom back in again. He was unyielding in his vision that the design of the iPod be simple and elegant, but equally cognizant of the fact that its success depended as much on making favorable deals with the music industry.

My favorite example of his dexterity at shifting from unsparing designer to expansive CEO was when he returned to Apple and the company had 12 different marketing departments, each with huge budgets, each running multiple campaigns. Jobs consolidated all the disparate departments down to one, which gave him the resources he needed for a single campaign: Think Different.

As a new entrepreneur, your big picture isn’t going to be quite so big or complicated. But relative to being a designer, you will need to significantly zoom your attentions out enough to escape the mental confines of being solely a craftsperson. You have to wisely pick and choose when you can obsess over a picayune detail and when a solution that might not be perfect is still good enough to ship—all the while always keeping the broader mission of your startup in perspective. Diego Rodriguez describes a designer founder as someone who loves “being in the flow, the center of the organization, solving the gnarliest problems.” To do that, you need to find the proper ratio of tweaking pixels to executing strategy—because your company is your craft now.

“To be a designer founder,” said Joe Gebbia,

… you’re going to have to let go of the perfection, craftsmanship, or whatever you want to call it, because a designer and a manager or exec are two different mindsets. Designers can be highly focused on details and minutiae and the depth of meaning in something that makes great design. A manager is completely different. They are about action and implementation and progress, not necessarily iteration. Eighty percent is done. Seventy percent is done. Let’s go.

This is easier said than done for many designers, including Joe, who struggled with the perfection affliction. As did Evan Sharp at Pinterest: “I always have a lot of tension between wanting to design and wanting to lead and manage.” In fact, an inability to break out of the craft box, to grow into a leader as well as a designer, is the chief failure mode for designer entrepreneurs. Diego Rodriguez has observed more than one such specimen in dread: “It’s, like, Oh my God, you’re never going to ship, because it’s never going to be perfect….And I can just see it: in 18 months you’re going to run out of money.”

You have to wisely pick and choose when you can obsess over a picayune detail and when a solution that might not be perfect is still good enough to ship—all the while always keeping the broader mission of your startup in perspective.

If you want the world to have nice things, you need to figure out how and where they can buy them. Which means that designers can’t isolate themselves in a design corner. They’ve got to help lead the business. “Design is the fun part,” said John Proksch-Whaley, Director of Design at Nascent Objects, “and I’m not going to be happy unless I’m making things. But what drives me to figure out all those other things is that if I don’t, I won’t get to see this become real. It will be a sketch, but I don’t get to touch and feel it at the end of the day.”

Or, as Evan said, “I’d rather build something imperfect that a lot of people use than something really perfect that no one uses.” In other words, just because you sometimes have to fight for unscalable feats of design, doesn’t mean that scale needn’t ever be a consideration. Just because you need to be a leader for design doesn’t excuse you from being a leader for anything else.


Turn the idea of “Fail fast to succeed faster” inward: towards the imperative for you to grow into a full-stack designer founder. You have to become a builder of design teams and a design-led company—not just a maker of cool products and beautiful objects. Designers, in other words, need to rapidly level up and become design-tech leaders, which demands a new arsenal of skills: how to facilitate among different types of stakeholders, how to assess viability and feasibility, recruiting and hiring, communicating research findings, boosting your organizational influence, and setting up a process that integrates design with engineering. In order to gain equal footing in a young startup, designers have to take on an equal share of the responsibility and risk. Of course, that should come with an equal share of the reward.

5. Design A System For Repeatable Genius

Jobs is remembered as a singular genius. And there’s no doubt that he was an inspired and unique mind. But a key component to his genius was his ability to find talented people, rally them around his cause, and then create the conditions that allowed them to thrive again and again. Without these people and process, he wouldn’t have been able to scale his dreams. And healthy as his sense of self was, Jobs wasn’t deluded about this fact. He once said, “Great things in business are never done by one person, they’re done by a team of people.” Steve Jobs’ true brilliance was in designing a system for repeatable genius.

The irony is that if you’re someone who wants to be the next Steve Jobs—someone who wants to build delight-giving, world-changing products and companies—the final, and perhaps most difficult, Jobsian peak you must summit is your own ego. Designers are very comfortable with making a thing, from conception to completion, all by our lonesome. We prefer it, trusting that no one will be able to bring our vision to life as well as we can, or will do it just as we want it done. But no successful designer founder is an island. Realize that if you want to build something greater than yourself, you need to first get over yourself and learn to scale your design through hiring, storytelling, and building culture and processes.

Designers who aspire to be designer founders need to understand that you don’t have to know or do everything yourself. Your strength comes from having a skillset that crosses disciplines. As a founder this means you just need to understand enough to recruit and hire great people to build out the many elements that make up your startup’s product. “I hired people who were better than me at design,” said Evan Sharp.

Indeed, the most effective (and happiest) design leaders we talked to were the ones who’d found designers and engineers superior at craft than themselves. “I know just enough to know that I am a bad engineer, a bad designer, a bad artist. But I’m fluent in those languages,” said Marc Fenigstein, cofounder and CEO of Alta Motors. Movewith’s designer founder Tricia Choi sees her role as a facilitator, who stands “at the crossroads of the artists and the dancers and the feelers and the philosophers, and the incredibly savvy business minds, product minds, engineering minds” and pulls them all together. Serial designer founder Gentry Underwood thinks of it as building a design “hive mind,” which enables you “just in conversation [to] iterate with incredible rapidity.” These founders understand that to put a dent in the universe requires many hands helping to lift and swing the hammer.

Another aspect to being Steve Jobs was his gift for storytelling—his uncanny skill at reading the audience, finding the right way to frame a story, and galvanizing others around a shared vision. He would even rewrite his communication team’s press releases the night before publication, to get the wording just right. Great storytelling can be your most powerful tool for disseminating and scaling your vision. “More than any place I’ve ever worked,” reported growth-team design lead Keenan Cummings, “[Airbnb] has a set of values. I can recite them off the top my head, and they influence the decisions we make.”

These founders understand that to
put a dent in the universe requires many hands helping to lift and swing the hammer.

Now, I’m not expecting young entrepreneurs to do the “reality-distortion field” thing that Jobs was known for—and please, no black turtlenecks. I just mean that if you want to launch something ambitious on the scale of Jobs, you need to be amazing—not adequate—at persuading investors, consumers, and prospective hires to care about whatever it is you’re trying to build. “You could have the most brilliant idea, the most talented team, and plenty of money,” said Lumi’s Jesse Genet, “but it doesn’t matter if you can’t steer that ship and get everyone on the same page. It’s irrelevant.” Abstract’s cofounder and CEO Josh Brewer put it even more flatly: “If you can’t communicate, you’re doomed.”

Lastly, designers respect Jobs because he was so obsessive-compulsive when it came to the smallest detail of a product—a true designer’s designer, as I said. But here’s the dirty little secret that I’ve waited until the filthy end to whisper: Steve Jobs wasn’t a designer. Or an engineer. Or a coder. Without Steve Wozniak’s engineering prowess early on, Tony Fadell’s genius for remaking the drab into the extraordinary, Jony Ive’s keen design acumen, or Tim Cook’s gift for building out unrivaled operations—Jobs would not have been able to produce the first Apple computer, or the iPod, or the iPhone. He would not have been able to raise a CNC robot army to mill unibody MacBook Airs from solid aluminum.



Steve Jobs wasn’t a designer, or an engineer, or a coder. He was the conductor of them all.

The story I shared in the last chapter about Jobs obsessing over the insides of a product wasn’t about one especially maniacal aesthete pouring over design for design’s sake. It was about a leader forging a set of values and an environment in which people are challenged to care deeply about the smallest aspects of the mission. It’s about building a culture that refuses to accept mediocrity. Jobs’ parting lesson for designer founders and all entrepreneurs is to be a great designer of organizations, one who understands the importance of building a culture and a process for excellence.



A Creative Expedition

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