The Way To Design 3

This book is dedicated to designers who dare to be
entrepreneurs, and entrepreneurs who want to harness
the power of design.

Prologue
Chapter 
Chapter 
Chapter 
Chapter 
Chapter 
Afterword
The Way To Design 5
Since this is a book about breaking out of narrow constraints,
there’s no tighter place to begin than the , square-foot
Dutch Colonial on Laconia Road that me and my nine brothers
and sisters were all jammed into. My parents turned the
attic and basement into usable living spaces, but even with
these renovations, we had to figure out how to shower every
morning with only two full bathrooms. And there was a pair
of kids to each bedroom.
t was in pairs that we grew up. & Roebuck because it had been sent to the wrong
Two girls. Two boys. Two girls. store, even real cars that we probably shouldn’t
Then two more girls. And lastly, have been driving at ages 13 and 11.
two more boys: me and my younger brother Mike. During the 1979 oil crisis, Mike and I set
Mike and I got the smallest bedroom, since we up a toy gas station on our front sidewalk and
were the youngest dyad of the crop. And that lined up every little car and scale model that
room wasn’t much bigger than a peapod. we owned. There must have been close to 100
But Mike and I were so close that we didn’t cars, including the last one in line, which had a
need a lot of space between us. We’d often lose to-scale handwritten sign on its rear bumper that
ourselves for hours playing with cars: Matchbox read, “Last car in line. No gas.” The Worcester
cars, Hot Wheels, Fisher Price and Tonka trucks, Telegram came by and got a photo of the Vassallo
cars we built from LEGOs, a go-kart that Dad fleet. The caption described Mike and I as,
bought at a deep discount at the Auburn Sears “Playing for Real.”
The Way To Design 6

A lot of people have similar stories—albeit
with fewer siblings usually in the mix. What sets
people who grow up to be designers apart from
most others is that they wanted to keep playing.
I’ve heard it time and again from prominent
designers, like Evan Sharp and Ben Blumenfeld,
that when they were kids, they didn’t know that
being a designer was an actual thing. They simply
liked using their imagination to make stuff (very
often with LEGOs). When they look back at their
childhoods what they see in the distance are….
Those drawings I made for my grandmother….
That summer I spent teaching myself to bind
books….The Mac II that I wrote my first program
on….That Big Foot monster truck model I didn’t
think I could build, but did.
This elemental compulsion is what and who

I mean when I say "designer". Not necessarily
someone who’s been classically trained in the Steve (front) and Mike in the Worcester Telegram.
fine arts, or industrial, graphic, or user-interface

design. I wasn’t. But more liberally, anyone—even unveiling a completed work to the world—even if
if they might not call themselves a designer—who the population of that world numbered just one
has designed, built, and shipped things. These are person—and saying, "I made this (for you)."
people who have lived among the tools; who have As they grew up, their childhood inclination for
experienced the deep satisfaction of refining the making things only deepened. And then, at some
smallest details of something to an exacting finish; point, like magic, the world started giving them
who know the pride and suppressed glee of finally money, health benefits, and a 401(k) to be this way.
The Way To Design 7

At least it felt like magic to me, when I Across industries, companies are trying to
rode that go-kart all the way from Worcester, infuse their organizations with design sensibilities.
Massachusetts into a job as a product designer And if you’re a talented designer in Silicon Valley,
at IDEO. There, I got to build everything from the work finds you.
furniture and sunglasses to bun toasters and There’s a subset of designers, however,
anesthesia-delivery devices. who’ve started to wonder if there isn’t something
After a long stint at IDEO, I went on to do more they can do than pure craft. If there isn’t
other things, including start companies, and a bigger impact they could be making on the
somehow along the way I wound up as an world. These young women and men look to the
investor. But I still build products on the side and designer cofounders of companies like Pinterest
sell them on Amazon. My idea of a fun weekend and Airbnb and they wonder if—and how—they
is finding bespoke manhole covers to give as might be like them. But they feel boxed in by
gifts, or helping my six-year-old daughter build a ignorance or trepidation. Or they’re lost at sea
2700-piece, 1:8 scale LEGO model of the Porsche as to where to begin.
911 GT3 RS. I could talk about the kinematics of I remember the feeling well. I loved and still
the machine I built in grad school for folding and love designing products, but after a half decade at
launching paper airplanes until there’s no one left IDEO, doing only that felt as constricting as that
in the room to listen. I’m a designer who happens tiny room with the bunkbed and one small desk
to be a venture capitalist. that I shared with Mike. I knew that I wanted to
do more. I was lucky and eventually figured out a
path, even though at the time there wasn’t much
guidance out there for designers who wanted to
Fortunately for anyone belonging to this become entrepreneurs.
unbearable tribe of nitpicky craftspersons, Unfortunately, when I survey the landscape
this is an amazing moment to be a designer. now, there’s still not much help for young
In recent years, design has come into its own designers. There are reports filled with statistics
as a competitive lever for businesses, as a set of about design—LinkedIn stats about designers in
practices for solving important problems, even as tech, numbers on designer-led startups, M&A
a method for optimizing your life. Design thinking activity of design firms, and fragmentary analysis
is being taught to kids in some primary schools. of the design ecosystem. Industry observations.
The Way To Design 8

This elemental compulsion is what and who I mean
when I say designer. Not necessarily someone who’s
been classically trained in the fine arts, or industrial,
graphic, or user-interface design. I wasn’t. But more
liberally, anyone—even if they might not call
themselves a designer—who has designed, built,
and shipped things. These are people who have lived
among the tools; who have experienced the deep
satisfaction of refining the smallest details of
something to an exacting finish; who know the pride
and suppressed glee of finally unveiling a completed
work to the world—even if the population of that
world numbered just one person—and saying...
The Way To Design 9

10
P R OL OGU E - P L A Y I NG FO R R E A L
For anyone belonging to this unbearable
tribe of nitpicky craftspersons, this is an amazing
moment to be a designer.
But there isn’t much substantive insight about analyze what we collected. We held mini-design
what’s required of designers to become successful sprints and prototyped numerous versions of what
founders, gleaned from the frontline stories of you’re reading in myriad forms. All in an attempt
those who’ve lived to tell the tale. I wanted to to plot the trail signs and marker-buoys of design’s
do something about this void, and I decided to terra incognita—how to go from designer to
approach the problem as a design challenge. designer founder. What follows is what we learned.
As a product designer-turned-entrepreneur-
turned-investor, I think that design is non-
negotiable for building the great companies of
the future. I want to help designers who want to This work is intended for entrepreneurial
become entrepreneurs and entrepreneurs who designers, for designers who want to know more
want to create design-empowered organizations. about what it takes to start a company, and for
So, like any good design thinker, I started off non-designer entrepreneurs and executives who
by forming a research team, to explore the real-life want to understand how to make design a core
stories of design entrepreneurs. Over the past nine value of their business.
months, we interviewed scores of designers, design After reading this, some designers may decide
scholars, and most importantly, designer founders that becoming a founder is not for them, and
(including the cofounders of Pinterest and Airbnb). there’s no shame in that. But for designers who
We set up a war room at Foundation Capital to are thinking about undertaking the entrepreneur’s
The Way To Design 11

Steve’s daughter - the next generation of Vassallo car nuts?
journey, I want you to know what will be required curiosity, and an incurable itch to improve
of you. I also want you to know that there things—and use it to elevate the way people live.
has never been a better time in history to be a You can use your mutant powers to transform—
designer with grand dreams. You might not know for the better—how we travel, eat, take pictures,
it, but you have it in you to do impossible things. share, collect, connect, cure diseases, vote, love,
You can take your designer’s brew of creativity, create. You can play—for real

You might not know it, but you
have it in you to do impossible
things. You can take your
designer’s brew of creativity,
curiosity, and an incurable itch
to improve things—and use it
to elevate the way people live.
You can use your mutant

powers to transform—
for the better—how we travel,
eat, take pictures, share,
collect, connect, cure diseases,
vote, love, create. You can
play—for real.

"Are you ready for this book??” That’s the provocation
on the back cover of The Universal Traveler, one of my
favorite books. Written by Don Koberg and Jim Bagnall,
two design professors at Cal Poly, and first published in
, The Universal Traveler is part self-help manual,
part treatise on creativity, part design workbook. There
are charming sections on things like, staying open to
“off-the-wall” ideas in Brainstorming (capitalized) sessions.
was introduced to it as an engineering About a decade later, after my run as a product

grad student at Stanford in the 90s. designer at IDEO—at a time when product
At the time, design was one of designers were thought of as the J.V. engineers—
the lesser disciplines in Silicon Valley. Steve I went back to Stanford for my MBA. I went to
Jobs hadn’t yet returned to Apple to begin his business school because I wanted to start my own
historic tear of design-centric product launches. company, but working as a designer hadn’t given
IDEO had only been founded a few years me the tools to do so.
prior. And David Kelley hadn’t yet codified Jump ahead a dozen more years—a few startups,
and made famous the methodology known as a a couple of IPOs, more than one career, and three
design thinking. Design was the “skin” that an kids later—and, from where I sit, there’s never been
agency was hired to slap on the real work of the a better time for anyone to start a company.
engineers, to make a product more palatable for I’ve never witnessed more innovation or faster
the fish-headed masses. acceleration of technologies and new business

From the cover of Koberg & Bagnall’s design treatise.
VCs like me are used to asking, Who

is your technical or business cofounder?
But some of us have also started to ask,
Who is your design cofounder?

It’s a journey.
A creative expedition.
To reinvent yourself from

a designer to a designer founder.
To build your startup into

a design-centric organization.
To create processes
for creating great things.
To remake the world

for the better.
And I’ve this book

to help you find your way.

models. Nor has there ever been more ready design-sensitive individuals, this is the most
access to risk capital, or better access to business powerful way to make a difference.
and engineering leadership. But in too many of It’s a journey. A creative expedition. To
the young companies I meet, there remains a reinvent yourself from a designer to a designer
crucial seat at the startup table that still needs to founder. To build your startup into a design-
be filled. centric organization. To create processes for
VCs like me are used to asking, Who is your creating great things. To remake the world for
technical or business cofounder? But some of us have the better. And I’ve written this book to help
also started to ask, Who is your design cofounder? you find your way.
Technical cofounders and business cofounders
will always have their place, but I believe designers
are now poised to demand equal footing. Because
to build truly enduring companies, having a great Since I believe each entrepreneur’s journey is
programmer or engineer or marketer is no longer unique, consider The Way to Design more compass
enough. You also need a great design lead. than map: guiding first principles to point you
Unfortunately, designers, by and large, in the right direction. I think of this work as an
aren’t any more prepared to launch their intellectual descendent of The Universal Traveler.
own companies than I was when I first But whereas that book promised to act as “a
started my MBA. I’m not saying an MBA is general guide to behaving creatively in a fast-
necessary, but entrepreneurial designers do changing world,” The Way to Design is intended to
need business fluency, in addition to design serve as applied wayfinding for a particular type of
fluency. Leadership and collaboration skills, creative actor—the designer founder—who wants
in addition to creativity and individual talent. to shape that world, one which is utterly changed
And a willingness to be not just the protector and radically more complex than the one in which
of aesthetics—but the integrator of aesthetics, Kolberg and Bagnall were writing.
technology, and values. Having walked this path Now, it’s important that you understand the
myself, I can tell you that there are no handrails context in which you’ll be operating. So, let’s
and it won’t be easy. Quite frankly, the course orient ourselves for the trek by tracing how design
will be arduous and most won’t have the nerve came to be so important. And then, if you’re
or perseverance for it. But for designers and interested, I’ll direct you to the trailhead

Until very recently, success in Silicon Valley required
focusing almost single-mindedly on an organization’s
technical prowess. It meant having an unimpeachable
technical founder, 10X engineers, and a relentless
devotion to computing dominance. What truly mattered
about consumers’ interaction with technology was
that it be fast. Expending valuable time on anything
else—particularly design—was evidence of distraction
from the real work of the company.
ears ago, when Larry Page was asked Intel, Microsoft, and Amazon, they’re stories of
what Google’s design aesthetic was, business executives and engineers. Design was
he replied, “Pine,” referring to an old an afterthought.
command line email program that was known But things have changed dramatically in
primarily for its speed. And when we look at just a few short years. Industry giants, like
the origin stories of established tech giants like Samsung, GE, and IBM, have spent hundreds

of millions to build in-house design studios and industry has come to understand a new
hire thousands of designers. Google has invested truth about modern business: more and more,
heavily to reinvent itself as a design-centric design comes first, and is now as indispensable
business. Highly lucrative new companies— as technology.
including Airbnb, Tumblr, Snapchat, Pinterest,
Instagram, and Pocket—have sprung from the
minds and hands of trained designers.
While other billion-dollar companies, like Slack, Three things are responsible for this remarkable
have been built by offering better designed shift. First, whether you're working on hardware
experiences with familiar technology. More or hosted software, the underlying technology
designers, like myself, have become investors. to prototype, produce, and launch products has
At Foundation Capital, my venture capital firm, only become better, cheaper, and faster over
we’ve backed Designer Fund, the first and only the last 25 years. Free and easy-to-use CAD
investment fund focused solely on designer- software, 3D printing, and crowdfunding have
founded startups. That’s because most of the made it easier and faster than ever to design,
The most fundamental software infrastructure

has become commoditized to the point where
most of the innovation is now created at the
interface with end users. In the consumer internet
world in particular, the marginal cost of software
is zero—and design is now the differentiator.

sell, and ship. Where, once, engineers used to The second reason that design has moved center
rely on raw programming languages to create stage is that consumer expectations have evolved.
software, today, they build from open-source Businesses, even in the very recent past, weren’t
libraries and pre-existing technology platforms. doomed to certain failure because of a weak emphasis
Meanwhile, at the bottom of the OSI stack, on design. The bottoms of drawers across the free
network speeds have gone from one gig to 10 world are littered with poorly designed products that
gigs to 100 gigs. But we’re approaching the sold well because of brilliant sales and marketing.
limits of optical lithography—the sheer physical (If you don’t remember or were too young for it,
constraints of how much we can fit onto a go check out the “Microsoft re-designs iPod
chip—and thus an end to the noble metronomic packaging” parody video from a decade ago.) But the
march of Moore’s Law. (One prominent public has come to expect more. Thanks to the work
engineer calls this “computer architecture’s of visionaries like Bill Moggridge, David Kelley, and
midlife crisis.”) Steve Jobs, people want user-devoted, frictionless
Even assuming we eke out another decade experiences in their interactions with technology.
and then make the leap to quantum computing, Jobs’ influence is especially pronounced.
it remains the case that the most fundamental Perhaps no single product has reshaped what people
software infrastructure has become commoditized expect of designed technology more than the iPhone.
to the point where most of the innovation is now Ever since its release a decade ago, consumer
created at the interface with end users. demand for useful, beautiful product experiences
have grown more insistent. You can follow the trail
of Palm’s death crawl all the way back to its CMO
saying, "Design is a commodity.” Even developer
In the consumer internet world in particular, the expectations for better design have heightened.
marginal cost of software is zero, and design is At Particle.io, a user-friendly platform for building
now the differentiator. “The expectation for a new IoT applications, Jon Logan and Richard Whitney
company is so much higher now,” Airbnb’s Joe told us that developers tolerate bad experiences
Gebbia said to me, “because what they did in six “only when there’s no other option." And they’ve
months [10 years ago] someone could do now in a found that customers often come back to their
week.” And therefore, “People have to come with better-designed product after having awful
more value.” experiences with competitors

Whether you're working on
hardware or hosted software,
the underlying technology to
prototype, produce, and launch
products has only become better,
cheaper, and faster over the last
25 years.
Free and easy-to-use CAD

software, 3D printing, and
crowdfunding have made it
easier and faster than ever
to design, sell, and ship.

The final reason that design has become essential is that
its scope and meaning have changed. When most laypeople
hear the term “design,” what comes to mind are things like a
Dieter Rams stereo receiver, a Noguchi coffee table, one of
the homes featured in Dwell, a Giugiaro concept car, maybe
a well-turned brand logo. I’m a craftsman at heart and I
honor this form of design. But “design” has come to mean
much more than craft.
ohn Arnold, perhaps the originator profound level, and what I’m talking about
of the design movement at Stanford, when I talk about design in this book. It’s not
taught a course called “How to Ask aesthetics. It’s knowing what questions to ask
a Question.” His belief was that “Each of man's and how to ask them, be it about a small product
advances was started by a question….Knowing or a planetary system.
what questions to ask and how to ask them is I met designer founder Nate Weiner at a design
sometimes more important than the eventual event at Stanford and later invested in his startup.
answers.” That’s what design is at the most When I interviewed him for this project,

Design is The What. What should you
be building? What’s the right opportunity
to go after? What’s the right problem to
solve? Asking the right question is half
the answer. Design is not about the drapes
or the drop shadows. Design is a messy,
holistic, human-centric process for solving
problems—not just stylistic problems,
but problems of all manner and level
of importance.
Nate told me that, at his company Pocket, In a world in which you can build anything,
the automatic retort to any questions regarding the onus for entrepreneurs has shifted from figuring
feasibility is, “Anything is a possible.” Because, out if you can build something, to understanding
“Can we do this is? is the wrong question to ask. whether it’s worth building it in the first place.
It’s, Why should we do this? How should we do And that’s why design is now more than the
this?...It doesn’t matter what ideas you have, window dressing. Design is The What. What should
it’s all about, Does this solve the problem?” you be building? What’s the right opportunity to go

after? What’s the right problem to solve? Asking the former CEO Herb Kelleher, who “completely
right question is half the answer. rethought the paradigm of how you get on an
Design is not about the drapes or the drop airplane.” Kelleher solved an efficiency problem
shadows. Design is a messy, holistic, human- and, in doing so, turned Southwest into one of
centric process for solving problems—not just the safest and only consistently profitable airline
stylistic problems, but problems of all manner in the country.
and level of importance. Another of Diego’s favorite examples is the
Uber app. For his money, the best design aspect
of the app, isn’t how attractive it is, but the way
that it deals away with the awkwardness of the
At Particle.io, they helped one customer to payment transaction. These kinds of solutions
develop a smart water meter that retrains aren’t necessarily pretty, but they’re innovative
people’s shower-water usage thresholds and effective.
through data-informed alerts. “This is a very This notion of design lines up with the
unglamorous product with huge potential most recent scholarship on creativity, which
applications,” said Jon Logan, “When you Scott Klemmer, cofounder and director of the
expand this to the scale of hundreds of Design Lab at UC San Diego, summed up as,
thousands, you’re talking about massive “You need to know the things that you need to
amounts of water savings. Apply this idea to know to solve the problem. And you need to not
agriculture and irrigation instead of home believe things that will get in the way of solving
use, and you can be smarter about how you’re the problem.” Viewed from this perspective,
watering fields for farms in Central Valley.” design is about searching out a product’s or an
Ask Diego Rodriguez, Global Managing organization’s purpose—the problem it solves—
Director at IDEO, which airline he thinks and then painstakingly making sure every facet
is the best design-led and in his opinion it’s of the solution supports this purpose. Design
not Virgin America, despite the care that that is a way of thinking. “I believe in a designer
airline puts into things like lighting and pilot’s mindset,” said Moxxly cofounder Gabrielle
jackets. “Cool, but that’s all veneer,” he says. Guthrie, “this approach that you take, regardless
Instead, Diego thinks the real design genius in of if you’re building products, teams, systems,
the industry is Southwest Airlines’ co-founder and or cultures”

Where do we go from here? It’s my conviction that the st
century will be the designer’s century, because I believe
that design is the greatest lever for building the greatest
companies to come. The most interesting innovation is
happening at the top of the stack—at the interface with
end users—where technology development intersects with
design and where a swipe right or a hold might decide the
next breakout business.
o take one example, if you haven’t re-engage with your friends, which Facebook hopes
logged on to Facebook in more than 30 will lead you to come back more often. This very
days, you’ll get an email that will link simple solution—a design solution—of letting you in
you through to your account without you needing to for 24 hours without a password addresses the very
remember your password. You’ll have 24 hours to basic human trait of forgetfulness.

Now that is an example of how an established
giant has put design to work to give its products Design has
an extra edge. And it’s just as applicable in the
early stages of product development and in the become the primary
early life of a startup. Adam Ting, head of design
at Blend, a next-gen mortgage startup, reports differentiator for most
that “Design has closed deals for us … design is
the main reason we’re different. There’s other companies, and it is
things we do … but the one readily apparent thing
is that the user experience is much better.” unlikely that a company
Design has become the primary differentiator
for most companies, and it is unlikely that founded today will
a company founded today will flourish without
a robust and thoroughgoing design strategy. flourish without a robust
and thoroughgoing
As a venture investor, I’ve seen startups fail for a design strategy.
lack of design, and companies that would’ve have
been an order of magnitude better if they’d had
design processes in place from the very beginning. to 6 percent.” Yes, there are notable exceptions.
Unfortunately, despite how indispensable But there should be more. And there will be—
design is today, a stark gap persists: Not many if designers start seeing themselves more often
people running top companies come from design as entrepreneurs. As the builders not just of
backgrounds. According to the most recent data products, but of companies. Leaders not just of
I could find, only 15 percent of the members of design but of people. Designers must embrace the
FounderDating claim design as their primary entrepreneurial spirit.
skillset. And, as its former CEO said, once When I left Stanford and began my career
you correct “for people who are more design- in product development I was set up with a
appreciators than designers, it’s probably closer $15,000 workstation and a $20,000 CAD

Solve a problem that is personal to you, a
problem that you live in. Be married to the problem.
Be so close to it that you understand it from the
inside out.
package sold by expensive sales reps and Today, 20 years later, you can design a
accompanied by a one-week training course in product with the freeware version of SketchUp,
Boston. My prototypes cost $50,000 and were make your first rapid prototype on your own
made in machine shops on equipment that ran desktop MakerBot, raise $100,000 in crowd-
upwards of half a million dollars. When we funding on Kickstarter, purchase $5,000 soft
were ready to release for mass manufacture, tools from PCH, set up virtual distribution with
we sent drawings and, in some cases, 3D files Shipwire or Amazon or both, and market and sell
to toolmakers who spent 12 weeks hogging directly to your customers off your own website
out hardened steel tools that cost no less than and in your own voice.
$100,000 per part.
Slowly, my product would wind its way
through the labyrinth of distribution, ultimately
landing in retail stores which required their own The tools really are in your hands now.
care and feeding: point of purchase displays, But the cardinal question that every aspiring
end caps, promotional materials, and, in some designer founder needs to answer before
cases, training. And for all of this hard work, you embarking on their entrepreneurial odyssey
might earn 40 points of gross margin, less than has changed. It is no longer: Can you build the
the end retailer that served as a shelf and not product? The starting point is now: Why are you
much more. building it at all?

The tools really are
in your hands now.
But the cardinal question that

every aspiring designer founder
needs to answer before embarking
on their entrepreneurial odyssey
has changed.
It is no longer: Can you build the

product? The starting point is now:

When we asked Joe Gebbia what he would The only thing that does
say to entrepreneurial designers if he were is knowing that you're solving
delivering the commencement address at RISD, something important.
he said, “Solve a problem that is personal to you,
a problem that you live in. Be married to the For Melissa Miranda, who led the interview
problem. Be so close to it that you understand portion of this project, that something important
it from the inside out.” is climate change and what designers can do to
Gabrielle Guthrie founded Moxxly, which alleviate the problem. “What matters most is
is building a better breast pump, precisely finding the leverage points where I can create
because she saw that so many products for the greatest impact. The structure is secondary:
women were awful due to the fact that they it might mean a side project today, a startup
were designed by people—i.e., men—who tomorrow, or a non-profit down the road.”
weren’t close enough to the problems. “One Evan Sharp was lucky enough to find his
thing that really resonated,” said Gabrielle, The What. “Honestly, Pinterest is just my
“was a blog post that said, if men had to use favorite thing, my favorite product. I just love
breast pumps, they would be quieter than a thinking about it and working on it.” And, like
Prius and look like an iPhone by now.” Evan, the true reward for any designer founder
Echoing Joe, Nate Weiner’s advice for an who finds the right problem to solve—is that
aspiring designer founder is, you get to try to solve it:
Solve a problem that you really care To own the design….That was what I
about....Because there are going to wanted to do every day….It’s fun
be days [when] you, literally, are not to be judged by the actual value of
going to want to go anymore. And the your work rather than someone’s
only thing that will get you through perceived value of your work.
that is caring about that problem. It’s fun to have no layers between….
Because if all you're here for is, I just It’s amazing when what you should
hope that we can make a big exit— be doing is exactly what you think
and that's it, that's not going to is the most valuable thing to do with
get you out of bed on those hard days. your time

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 , when I got the news
that Steve Jobs was dead.
t’s been more than five years since responsible for raising consumer expectations
his passing and yet: pull out your for thoughtfully made products, than the late
smartphone, book an Airbnb for Apple cofounder.
the weekend, Slack your coworker a message, Some of my interviewees for this project lead
or ogle the Tesla self-driving by—and Jobs’ huge tech companies; some are rising designer
perfectly beveled shadow looms large. We live founders. In both cases, time and again, Steve
in the design-esteemed world that Steve Jobs Jobs came up as reference point, illustration, or
ushered in. No individual has influenced the exemplar. He remains the most idolized modern
role of design in tech more, or is more founder and product-design obsessive

THINK BIG
DESIGN A
SYSTEM FOR GET SMART
R E P E ATA B L E G E N I U S ON BUSINESS
BREAK OUT OF B E A N A DVO C AT E

THE CRAFT BOX FOR DESIGN

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.

s my friend and mentor David Kelley said, “[I]t’s hard to argue against scale if you’re
has said: "If the goal is to change the talking about positive social impact….I’ve lost
world, the business part changes the a little bit of patience with products that aren’t
world faster." I’d like to think that’s why David designed to have a really large reach.”
eventually forgave me for leaving IDEO. Pure That’s not to suggest you snort a line of
design wasn’t giving me the license or leverage coke laced with delusions of grandeur and then
to work on the problems I wanted to try to solve, start nude-practicing your TED Talk in the
at the scale that I wanted to solve them. So I mirror. The first step is always to find the right
became an entrepreneur. Today that tension has opportunity to work on—one that you care deeply
to be even greater for designers. When my 12-year about even if it doesn’t seem like it’s going to
old son can code and create, the most important change everything forever and transfigure you into
question for product designers is no longer, “How a living god. Be open and prepared to scale your
can I build this?” Instead, as I wrote in the prior modest solution into a larger vision.
chapter, designers need to ask themselves and their Take the example of Nate Weiner, who in 2007
cofounders the deeper question of, “Is it worth got tired of emailing himself article links to read
building it in the first place?” Or, said another way, later. So, in a night, he taught himself to make a
“Is it going to matter? Is it going to address a real Firefox extension and banged out a little plug-in
problem or opportunity in the world?” that allowed him to Read It Later, as he would
come to call the product. It turned out that a lot
It hadn’t dawned on Joe Gebbia, who had dreams If the goal is to

of becoming a painter, that the objects in the
world were acts of design until he discovered change the world, the
industrial design at RISD. “I became very
intrigued and said to myself, ‘I would much rather business part changes
apply creativity to solving problems and improving
people’s lives than improving the state of the art the world faster.
world.’” Similarly, talking about the millions of
people who use Pinterest every day, Evan Sharp

of people had the same problem and, much to funding, rather than maintain Airbnb as a lifestyle
Nate’s surprise, those initial 160 lines of code became business. They did so because they realized that,
one of the most popular apps in the Apple Store, given how big the travel market was, they had a
and eventually became the company Pocket. once-in-a-lifetime opportunity to build something
More likely than starting off with a that might outlive them:
megalomaniacal roadmap for global conquest,
this is the typical journey of a designer founder. The brands we admire—Nike, Apple,
You identify a problem and attempt to solve it as Disney—have gone beyond their
simply as possible. But once you do, you quickly originators. They created these brands
realize that there’s a web of problems that your that in some cases define a generation.
solution addresses; so, you start solving for those, Nike in the 90s was the defining brand.
too. And it continues to expand out from there: Apple in the 2000s was a defining brand.
We did all the math and reasoning that
I need to be able to save this content for we could and realized that we had the
later. Huh, what if millions of people chance to build one of those brands.
did that? What would that unlock?
What if it’s not just for written content They decided to “swing for the fences,” not
but for voice and video? And then based knowing whether or not it would work out.
on all the data you get, now we know If you have the stuff of which Jobs’ ambition
what all the best content is. How can we was made—if you want to make a big and
use that to power recommendations? meaningful difference—then the surest way to
create large-scale impact today is through the
When Nate retraces Pocket’s widening circle, deft use of technology and the wise deployment
over nine years—from homemade plug-in to 10 of capital. Think of technology as the sword and
million monthly unique users and two billion business as the shield. The designer founder
items saved—I hear someone who models the is one who can choreograph both to maximal
Jobsian trait for embracing expansiveness that effect. And the question of what you're going to
I want to see in all designer founders. build—the battle to be joined—has never been
Joe, likewise, recounted the story for me of more important. Creativity alone isn’t enough.
he and his cofounders deciding to take venture Designers need to be prepared to think massive

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.

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.
f you’re a designer who’s a new Do you understand the fundamental financial

entrepreneur, you’ll need to find metrics of your business?
a partner with a solid sense for If you’re going to live in the land of business,
business. But you’ll also need to grasp enough you need to speak the language of business.
of it yourself in the event things go south in the Obvious as this seems, I believe it needs stating
relationship (See: Jobs-Sculley, 1986) and to because I know that many designers feel like
protect yourself from being taken advantage of by business is slimy and/or alienating and/or just not
unscrupulous investors. If you’re fundraising, for fun. (After securing Pocket’s first round of venture
example, and are offered a swanky valuation— funding, Nate Weiner found himself asking,
do you know what the terms for that price will “What’s a run rate?”) Pre-founder designers only
cost you in the future? Do you really grok the want to be creative and make cool shit. I get that.
difference between fixed and variable costs? I left the Stanford engineering Master’s program

in 1995 brimming with optimism and a sense that the last great desk phone. But truth be told, Cisco’s
"the best idea wins." While I'm just as optimistic enterprise sales force probably could have sold as
now as I was then, I can assure you, the best idea many systems had we designed the last not-so-great
definitely does not always win. desk phone, instead. What I learned was a) you
Oracle never had the best database. They still need both design and distribution, and b) I had a
don't. Cisco never had the best switches and lot to learn if I wanted to start my own company.
routers. They still don’t. What these companies Once upon a time, when I was applying to
do have is incredible marketing, distribution and business school (the first line of the worst fairytale
sales execution. Now, I’m actually very proud of ever), I responded to the essay question “Why do
the family of VoIP phones that I helped develop you wish to earn an MBA?” by drawing the Venn
for Cisco and believe it may go down in history as diagram below.
Steve’s Venn diagram for business school, 2001.

A crop of The Realm of Venture. See the full map at thewaytodesign.com
If you’re going to live in the land of business,

you need to speak the language of business.

What I was trying to convey was that but you can’t hide your head in renderings.
through IDEO I had lots of user-centered design Nor should you see business as just a necessary
experience. I had engineering training from evil. IDEO’s Diego Rodriguez, for example,
Stanford, so I felt comfortable answering the considers it a creative input: “I think money has
question of “Can it be done?” But I knew that historically been the missing ingredient in a lot of
this third circle—business needs—was missing. design conversations … [But it’s really] a liberating
When I left IDEO, I didn’t understand basic constraint. When you ask a customer to pay for
things like how gross margins are really calculated. something, it’s so different from asking, ‘What do
I had no concept of costs that were below the line. you think?’” Not factoring in business needs, in his
Customer acquisition cost? What? To someone opinion, is like “designing bridges without gravity.”
who builds stuff, you think, my costs are the parts Don’t bolt on business the way that businesses
that go into this physical object that makes a sound bolted on design for so many decades. And take
when I drop it on the floor. All the other costs that heart in the fact that it’s far easier for designers to
go into building a business were not obvious to me. get up to speed on business than it is for business
I suspected back then, and am more convinced people to get up to speed on design. Business is a
than ever now, that entrepreneurial designers need set of concepts and practical skills, a set of tools
to be thinking about all three circles in the Venn; that people of every background can and have
and if they want to play a critical role in shaping the learned. And if there’s one thing designers are good
future, they have to live at the intersection. at, it’s learning how to use tools. “My approach
When designers ask me the best way to start earning has been to embrace it,” Jesse Genet, the designer
a seat at the founders table, I tell them to get smart cofounder and CEO of Lumi, says,
on sales, distribution, marketing, growth. “If you
want to be leading a huge product that has lots of I don’t have an MBA or a finance
scale, you need to learn business,” advises Evan degree, I don’t know what someone is
Sharp, who admits that he was a business innocent talking about when they say EBITDA.
in Pinterest’s early days: “I got lucky. It could have It feels overwhelming, but like a lot of
been really shitty for me, and I could have built skills, the fundamentals are not that
something big that I didn’t get to be part of.” hard…. My advice is skip the imposter
You don’t need to get an MBA like I did (it syndrome, get in there and learn to enjoy
took me a long time to pay off my student loans!), it. It’s the lifeblood of your company

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.
e derisively referred to the sales copying machines, because their ideas about
and marketing executives who product design amounted to clueless facsimiles
dictated product decisions at of what had come before.
incumbents like IBM and Xerox as “toner Even though, for the health of your startup,
heads,” after the black powder that goes into and for your own self-interest, you need to get

It’s the duty of the designer in the
founding cohort to stop 1984 from
happening to your company.
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.

smart on business, never forget that the most They have no conception of the
important thing you’re bringing to the enterprise craftsmanship that’s required to take
is design. Design will be the key differentiator for a good idea and turn it into a good
the great companies of the future and it’s your job product. And they really have no
to ensure that your startup will be one of those feeling in their hearts, usually, about
companies by being the voice for design. wanting to really help the customers.
I understand the exigencies of trying to keep
a young company on its feet. Sometimes short- It’s the duty of the designer in the founding
term-thinking decisions are made for the sake cohort to stop 1984 from happening to your
of revenue. But if you let other elements in the company. "Never send a suit to do a pirate’s
company consistently override design, then job," Jobs said. Teach your organization to
before long it won’t be part of your company’s esteem design. Model the principles of design as
core strategy. Case in point, one designer a methodology for figuring out what problems
cofounder with whom we spoke admitted that to solve and how. Show your colleagues the
he struggled to keep the “insidious” influence worth that comes from putting the end user first.
of sales culture from pushing out design as And strive for greatness in design even if that
a priority at his startup. “The system is still means making a design choice that won’t scale
favoring revenue … and it’s hard to account in the near term. A great designer cofounder
for all the little things that come up later that will demonstrate how design can define and
you don’t even think about.” sometimes even save your company.
Jobs painted a depressing picture of what
happens when design gets driven out of decision-
making and the “toner heads” run the show.
Take the story of Airbnb cofounders Joe Gebbia
The companies forget what it means and Brian Chesky. In 2009, they had a problem.
to make great product. The product Rentals weren’t taking off, and the business was
sensibilities and the product genius … close to going bust. In Joe’s words, “For the first
gets rotted out by people running these year of the business, we sat behind our computer
companies who have no conception of screens trying to code our way through problems.
a good product versus a bad product. We believed this was the dogma of how you're

supposed to solve problems in Silicon Valley.” offering your home … to strangers … on the
But then, they got a kick in the ass from Paul internet. Or, on the other side of the screen,
Graham at Y Combinator, and realized that they you’re looking for a way to sleep … in someone
had permission to do something that didn’t scale, else’s home … the home of a stranger you met
but would come to make all the difference. They on the internet. It sounds crazy but the design
rented a camera, flew to New York, and worked process made it work, by revealing to Joe and
with property owners to take high-quality photos Brian that what they were really trying to build,
of the properties. During the process, they also at the heart of the matter, wasn’t an online rental
gained priceless on-the-ground insights into their market—it was trust, actually. Trust between
users’ experiences: the property owners and renters, and trust in
the Airbnb platform. High-quality photos,
We had been struggling for so long smartly calibrated descriptions, and a user
when we finally sat down with the interface that was truly easy-to-use were some
early adopters. Talk to us—what are of the conclusions reached by applying design
your issues? Oh my God, the thing to solve the problem of building trust. “There
we thought took two clicks, took 12! were no sharp edges on our site,” said Joe,
We were way wrong. It felt like this “The design had to communicate … that this
moment of enlightenment, seeing the is a trustworthy thing.”
world through their eyes. We gathered Design pushed through people’s
all those sources, stimuli, observations, psychological “Stranger!” barrier, and the
and came back to SF, and we got company’s rentals skyrocketed as a result.
smart because of it. The philosophy at Airbnb now, is that before
something goes out the door, it has to be a
Joe and Brian took what they learned and “minimum awesome product.” Joe explains:
made a few simple design enhancements— “For our business in particular, which is building
adding attractive images, editing the UI—and a relationship of trust with somebody, you would
it led to an almost-immediate doubling of their never, ever use a minimum viable approach—just
weekly revenues. like minimum viability would never be the goal
Now, many thought Airbnb’s basic business when it came to building a relationship with
model wasn’t workable. Think about it. You’re somebody in your personal life”

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 -page brand document, which included a new
company name, NeXT, and the exact angle (°) 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."
he stories that get told about Jobs are switching focal points and letting go of his fixation
always of how exacting he was, down on simply the product. Jobs knew how to zoom
to the type of wood tables he wanted out from his microscopic attention to detail and
for the Apple Stores. But the underreported consider the big-picture needs of Apple—then
feature of his success was how adept he was at zoom back in again. He was unyielding in his

vision that the design of the iPod be simple and solution that might not be perfect is still good
elegant, but equally cognizant of the fact that its enough to ship—all the while always keeping the
success depended as much on making favorable broader mission of your startup in perspective.
deals with the music industry. Diego Rodriguez describes a designer founder as
My favorite example of his dexterity at shifting someone who loves “being in the flow, the center
from unsparing designer to expansive CEO was of the organization, solving the gnarliest problems.”
when he returned to Apple and the company had To do that, you need to find the proper ratio of
12 different marketing departments, each with tweaking pixels to executing strategy—because
huge budgets, each running multiple campaigns. your company is your craft now.
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 “To be a designer founder,” said Joe Gebbia,
going to be quite so big or complicated. But relative
to being a designer, you will need to significantly … you’re going to have to let go of the
zoom your attentions out enough to escape the perfection, craftsmanship, or whatever
mental confines of being solely a craftsperson. you want to call it, because a designer
You have to wisely pick and choose when you and a manager or exec are two different
can obsess over a picayune detail and when a mindsets.
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.

Turn the idea of...
...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 can be highly focused on figure out all those other things is that if I don’t,
details and minutiae and the depth I won’t get to see this become real. It will be a
of meaning in something that makes sketch, but I don’t get to touch and feel it at the
great design. A manager is completely end of the day.”
different. They are about action and Or, as Evan said, “I’d rather build something
implementation and progress, not imperfect that a lot of people use than something
necessarily iteration. Eighty percent is really perfect that no one uses.” In other words,
done. Seventy percent is done. Let’s go. just because you sometimes have to fight for
unscalable feats of design, doesn’t mean that scale
This is easier said than done for many designers, needn’t ever be a consideration. Just because you
including Joe, who struggled with the perfection need to be a leader for design doesn’t excuse you
affliction. As did Evan Sharp at Pinterest: “I always from being a leader for anything else.
have a lot of tension between wanting to design and Turn the idea of “Fail fast to succeed faster”
wanting to lead and manage.” In fact, an inability inward: towards the imperative for you to grow
to break out of the craft box, to grow into a leader into a full-stack designer founder. You have to
as well as a designer, is the chief failure mode become a builder of design teams and a design-
for designer entrepreneurs. Diego Rodriguez has led company—not just a maker of cool products
observed more than one such specimen in dread: and beautiful objects. Designers, in other words,
“It’s, like, Oh my God, you’re never going to ship, need to rapidly level up and become design-
because it’s never going to be perfect….And I can tech leaders, which demands a new arsenal of
just see it: in 18 months you’re going to run out skills: how to facilitate among different types
of money.” of stakeholders, how to assess viability and
If you want the world to have nice things, you feasibility, recruiting and hiring, communicating
need to figure out how and where they can buy research findings, boosting your organizational
them. Which means that designers can’t isolate influence, and setting up a process that integrates
themselves in a design corner. They’ve got to design with engineering. In order to gain equal
help lead the business. “Design is the fun part,” footing in a young startup, designers have to take
said John Proksch-Whaley, Director of Design at on an equal share of the responsibility and risk.
Nascent Objects, “and I’m not going to be happy Of course, that should come with an equal share
unless I’m making things. But what drives me to of the reward

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 this 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.

he irony is that if you’re someone who
wants to be the next Steve Jobs— These founders
someone who wants to build delight-
giving, world-changing products and companies— understand that to
the final, and perhaps most difficult, Jobsian peak
you must summit is your own ego. Designers put a dent in the
are very comfortable with making a thing, from
conception to completion, all by our lonesome. universe requires many
We prefer it, trusting that no one will be able to
bring our vision to life as well as we can, or will hands helping to lift and
do it just as we want it done. But no successful
designer founder is an island. Realize that if you swing the hammer.
want to build something greater than yourself,
you need to first get over yourself and learn to
scale your design through hiring, storytelling, artist. But I’m fluent in those languages,” said
and building culture and processes. Marc Fenigstein, cofounder and CEO of Alta
Designers who aspire to be designer founders Motors. Movewith’s designer founder Tricia
need to understand that you don’t have to know Choi sees her role as a facilitator, who stands
or do everything yourself. Your strength comes “at the crossroads of the artists and the dancers
from having a skillset that crosses disciplines. and the feelers and the philosophers, and the
As a founder this means you just need to incredibly savvy business minds, product minds,
understand enough to recruit and hire great engineering minds” and pulls them all together.
people to build out the many elements that make Serial designer founder Gentry Underwood thinks
up your startup’s product. “I hired people who of it as building a design “hive mind,” which
were better than me at design,” said Evan Sharp. enables you “just in conversation [to] iterate with
Indeed, the most effective (and happiest) incredible rapidity.” These founders understand
design leaders we talked to were the ones who’d that to put a dent in the universe requires many
found designers and engineers superior at craft hands helping to lift and swing the hammer.
than themselves. “I know just enough to know Another aspect to being Steve Jobs was
that I am a bad engineer, a bad designer, a bad his gift for storytelling—his uncanny skill at

reading the audience, finding the right way to Lastly, designers respect Jobs because he was
frame a story, and galvanizing others around so obsessive-compulsive when it came to the
a shared vision. He would even rewrite his smallest detail of a product—a true designer’s
communication team’s press releases the night designer, as I said. But here’s the dirty little secret
before publication, to get the wording just right. that I’ve waited until the filthy end to whisper:
Great storytelling can be your most powerful tool Steve Jobs wasn’t a designer. Or an engineer.
for disseminating and scaling your vision. Or a coder. Without Steve Wozniak’s engineering
“More than any place I’ve ever worked,” prowess early on, Tony Fadell’s genius for
reported growth-team design lead Keenan remaking the drab into the extraordinary, Jony
Cummings, “[Airbnb] has a set of values. Ive’s keen design acumen, or Tim Cook’s gift for
I can recite them off the top my head, and they building out unrivaled operations—Jobs would
influence the decisions we make.” 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.
Now, I’m not expecting young entrepreneurs to Steve Jobs wasn’t a designer, or an engineer,
do the "reality-distortion field" thing that Jobs or a coder. He was the conductor of them all.
was known for—and please, no black turtlenecks. The story I shared in the last chapter about
I just mean that if you want to launch something Jobs obsessing over the insides of a product
ambitious on the scale of Jobs, you need to be wasn’t about one especially maniacal aesthete
amazing—not adequate—at persuading investors, pouring over design for design’s sake. It was
consumers, and prospective hires to care about about a leader forging a set of values and an
whatever it is you’re trying to build. “You could environment in which people are challenged
have the most brilliant idea, the most talented to care deeply about the smallest aspects of the
team, and plenty of money,” said Lumi’s Jesse mission. It’s about building a culture that refuses
Genet, “but it doesn’t matter if you can’t steer to accept mediocrity. Jobs’ parting lesson for
that ship and get everyone on the same page. designer founders and all entrepreneurs is to
It’s irrelevant.” Abstract’s cofounder and CEO be a great designer of organizations, one who
Josh Brewer put it even more flatly: “If you can’t understands the importance of building a culture
communicate, you’re doomed.” and a process for excellence

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.

C ha pte r

Granted, you’re an aspiring designer founder; or you’re a
non-designer entrepreneur who nevertheless understands
that design is critical to the cause of starting a great
company. Now, you want to know how you actually put
design into practice for the new endeavor you want to
launch. How, in fact, do you create an organization
that has this mindset and method at its beating heart?
How do you “design” your startup?
During the scores of hours I spent talking to entrepreneurs
at design-led companies, a number of themes kept recurring:
three beacons, let’s say, that you should steer towards, to
found a design-centric business.

The first thing to be mindful of is to build design into a
startup's very foundations, rather than bolt it on later as
a mere facade. If a startup is serious about competing on
design, then those practices and that mindset have to exist
at a company’s inception and throughout its lifecycle.
The evidence is overwhelming that when it’s not, especially
for young companies, competing demands will inevitably
crowd out design.
’m not saying that a startup needs create value—it has to be an integral part of
design in equal measures at every your company’s journey.
turn. If your user-credentials By far the most important thing you can
database has been hacked, it’s Engineering, I do to empower design within your organization is
need more power (i.e., two-factor authentication)! to have a designer in your founding team.
But for design to be more than a spiffy website In fact, when I asked Evan Sharp how essential
and clever logo—for design to be a meaningful having a designer cofounder is he said, “You
approach to how you solve problems and thereby can’t do it any other way….If the goal is to have

a human-centered product, you need people who led the initial investment in it after getting to
value human-resonant products in your company.” know Ben and Enrique, and seeing that they
Some of these “state of design” appraisals shared my conviction that designer founders
that I’ve read quote industry stats, like number are the future. Designer Fund is the first seed
of design firms acquired or design patents filed fund with this tenet as its core investment thesis.
in the past year, as evidence of tech companies It’s backed companies devoted to brilliant user
finally seeing the light. But I think that’s a experiences, including Stripe, Omada, Framer,
wrongheaded measure. Loading on a bunch and AltSchool. It also provides professional
of young designers—giving your company a development to designers, and helps connect
schmear of design—without integrating design them with other designers and entrepreneurs.
into your decision-making, without making Designer Fund is the realization of dreams that
it integral to your business’ strategy? To me, I (and many others) have had since my IDEO
that reeks of the inadequate design-as-façade years, as well as an indication of the shape
approach of old. of things to come.
Two fellow designers in the Valley who
do get it, though, are Ben Blumenfeld and
Enrique Allen, the founders of Designer Fund.
Designer Fund is a seed fund that invests in Another person who understands how indelible
and supports startups founded by designers. I the very first people you bring into a business
You can’t do it any other way…. If the

goal is to have a human-centered product,
you need people who value human-resonant
products in your company.

In his book, Let My People Go Surfing,
Chouinard talks about Patagonia’s
policy of recruiting very talented,
highly motivated people and then
leaving them to manage their own
schedules because...

are to shaping its culture is one of my heroes in people love. He has, in other words, designed an
business, Yvon Chouinard, founder of Patagonia, organization that almost autonomously designs
the highly successful outdoor-apparel maker. great products.
Chouinard—who’s a designer in my book, even When management consultants come
if he doesn’t think of himself as one—built a to Chouinard and ask him how to replicate
company with an amazing work culture based Patagonia’s culture of independence and
on independence, achievement, and social productivity for incumbent companies, he tells
responsibility. Back in the 1970s, Patagonia them, “Forget it. You’ll fail. Because you have to
was already giving benefits to its employees, start with the very first person you hire.”
like generous maternity leave, flexible scheduling, That echoes something Joe Gebbia told me:
and in-house childcare, which many companies “Culture doesn’t make the people, it’s the people
to this day still don’t offer. Now, three months in your building that make the culture. Which
of vacation for all employees isn’t going to means spend as much time up front to get it right,
scale for most companies, but what Chouinard to get the right people in, because it’s a lot easier to
did was to attract talent uniquely suited to mold concrete when it’s wet than to chip away at it
his mission. when it’s dry.”
In his book, Let My People Go Surfing, In my own career, I’ve seen the power
Chouinard talks about Patagonia’s policy of of design to define products and transform
recruiting very talented, highly motivated people businesses—but only when it’s part of the
and then leaving them be to manage their own company’s DNA. An empowered, foundational
schedules. His unimpeachable reasoning on the design culture will change the organization; a
latter is that, “A serious surfer doesn't plan to bolted-on design presence will fail. Either, during
go surfing next Tuesday at two o'clock. You go the misty mountain origins of your startup,
surfing when there are waves and the tide and dwarves banged an obsidian keystone—with your
wind are right.” Chouinard, himself, now takes designer founder’s name chiseled in it—into the
June to November off each year to go fly-fishing cold firmament of how you do business. Or else,
in Wyoming. He does so confident that he’s put your company has an inflatable bouncy castle—
people in place who are more capable than he at with “Design” written in black Sharpie on it—
tending to Patagonia’s day-to-day needs and a that it busts out for happy hours and holiday
structure in place that keeps making clothes that parties, w00t

"There is no try,” teaches Master Yoda. Who, if memory
serves, was my instructor for ME (Electro-Mechanical
Systems Design), a course at Stanford in which you were
asked to build the most absurdly unbuildable products.
The project briefs made me literally stare, scratch my
head, and think, I don’t know how you make that happen.
Example: my first assignment was to design a rideable
paper bicycle.
ll the stuff you’re asked to do early on begin to gain purchase on the problem, until it
when you choose to become a product eventually bends under the force of your creative
designer seem almost impossible. effort. And before you know it, you’re cruising
But the more you do it, the less impossible the around on a paper bicycle.
impossible seems. Over time, you get more This is the sort of mentality that a
comfortable doing what seemingly can’t be designer—someone who has learned to design
done, because you learn from experience that if by designing—will bring to the founding table.
you work and prototype and then re-work, you Adrian James, cofounder of Omada, says that

when he looks at the world, “I see all these little mock-ups and models. It’s extremely powerful,
things that are broken. But I don’t experience especially in your earliest days as a company,
it as negative. Rather, I experience them to have someone who can convert your abstract
as exciting little challenges all around me.” ideas into something with existential heft.
(Incidentally, one of my favorite definitions of an A tangible prototype—even one that’s made out
entrepreneur is "someone who does more than of foamcore or cardboard—will open up a visual
anyone thought possible with less than anyone line of communication for your team; it will
thought possible.") create a shared reality for your startup to rally
What this means in practice is that a designer around and iterate on. Shireen Yates,
cofounder will be a compulsive design doer. CEO and founder of Nima, and Xander Pollock,
She will rush to prototype, storyboard, create a designer entrepreneur whose company was
What are the essential elements

of the designer’s mind? I’d say, at the
most fundamental: curiosity and a need
to fix things. These perhaps inborn
characteristics, through training practice,
beget a sensitivity to finding the right
problem to work on and a will for doing
what seemingly can’t be done.

acquired by Google, both volunteered that sprint cadence.” She adds: “The CEO, if they’re
having something actual and vivid to show not a designer founder, usually doesn’t have the
investors—even if it looks janky as hell—will time to facilitate that conversation within the
also help you fundraise. A fact that I, as an leadership team.”
investor, can attest to.
If you’re an engineering or business cofounder,
it might be uncomfortable to add a weirdo
designer to your early team, but the earlier a What are the essential elements of the designer’s
designer is added as a strategic peer, the more mind? I’d say, at the most fundamental: curiosity
likely it is that your startup will develop a design and a need to fix things. These perhaps inborn
culture. Joe Gebbia describes this as, “The space characteristics, through training practice, beget
around the creation of the product, the supporting a sensitivity to finding the right problem to work
mechanism, the guidebook to how we want people on—which I’ve discussed in prior chapters—
to go about the creation of the product. The and a will for doing what seemingly can’t be
unspoken social contract you have with the people done. Finally, the outgrowth of this disposition
in your company to build the thing you’re trying is a creative process that embraces the wildly
to bring to market.” interdisciplinary and the messy.
I can’t overstate the lasting advantage such a It’s not about making your startup more
culture will give your company. In a sense, you artistic. Design is a modality for practical,
want a designer cofounder in order to project human-attuned problem solving. What a design
her weirdness onto the organization. Her design culture does is liberates the creativity of the
sensibilities, design intelligence, even design entire organization—not just designers but
neuroses. Meld your startup with the mind business, engineering, the entire stack—to readily
of a designer. Entrepreneur and IDEO alum generate ideas and continuously test them for
Tiffany Card uploads her design consciousness validation. Problem-solve and iterate: it’s what
to her companies by sharing “how design-led a startup must do to thrive; it’s what a designer
organizations do decision-making, all the way does by temperament and training. And if this
through to really sitting down and, Here are the mindset is mapped on to your company, then
meetings you should have on a weekly basis … [and whatever other features you build, impossible
demonstrating] how design can be built into a will not be an option

I think that having a designer cofounder is crucial to the
implicit culture of a startup—to installing an inherent
dedication to both choosing the right opportunity and
delivering an exceptional solution. But the next imperative
to “designing” a startup/forming a design-centric
organization is to establish an explicit culture, one that
respects the journey over the destination.
DEO used to display their most that design is a finite and definite thing—a
celebrated products in glass trophy bullseye you hit and then call it a day.
cases. They had every reason to be The truth is very much the contrary. Design
proud of their designs. Their portfolio includes isn’t something that can be bottled under glass
much-lauded products like Apple’s first mouse, or kept genied inside of physical artifacts. The
Eli Lilly insulin injection pens, the Palm V, product is a point, not the point. Or, as I like to
Swiffer cleaning products, a portable heart say: Product-market fit is a liquid not a solid.
defibrillator, and countless other things you’ve Meaning, achieving product-market fit is a great
probably used. But the danger in fetishizing “the thing, but it’s a transitory achievement—a false
product” is that this creates the false impression summit of sorts. The competitive landscape

changes. Your customers will want more. New and CEO of Modsy, is one such designer: “I go
technology enables new features/functions/form home obsessed about how customers are going to
factors. The goal is not to achieve product-market experience Modsy, and love it, and talk about it to
fit, but rather to achieve a drumbeat of regular everyone they’ve ever met. Not: How do I get $10
and repeated product-market fits. out of my customers? That would be nice, but I’m
What really matters for a modern company is so much more concerned about the experience.”
building design processes—lightweight methods Similarly, when I interviewed Greg Duffy,
and processes for problem-solving, creativity, and cofounder of Dropcam, he told me that they
iteration. At Delighted, process removes a layer of could’ve gone after the home security market by
worry, says its CEO and designer founder Caleb trying to frighten their customers about the big,
Elston, because “Every time we start a project, bad world lurking outside their windows. But they
we don’t have to reinvent how to do it.” It might wanted to be more than a security camera for their
not make sense if you’re only, say, four people, customers. Their vision for the company was to
but sometime before Employee #40, all startups create a private home video camera and cloud video
should follow suit and design not just a great archive for people to capture all the moments of
product, but a process for continuously designing their lives, which would otherwise be lost. They built
great products—a system for repeatable genius. a product and service that their customers loved and
What this system will look like will vary from were willing to pay a monthly subscription for. They
company to company, but any one worth its salt will consciously chose joy over fear—chose to build trust
value two things above all: the user and the process. and a long-term relationship, rather than cash in on
myopic transactions.
Similarly, when Josh Brewer led the design
team at Twitter, they committed to championing
In the last chapter, I called for aspiring the user experience—
designer founders to never lose sight of the
business side of their companies. But today, the And that made me, and a number of the
savvy strategy for any business is to not be overly designers on the team, unpopular in a lot
focused on short-term transactions, and instead, of cases and in a lot of meetings. Because
to do what comes naturally to designers: put we were the ones saying, “I get it. We
the end-user first. Shanna Tellerman, founder want to do this, and I see the revenue

Product-market fit is a liquid not a solid.
Meaning, achieving product-market fit is a great
thing, but it’s a transitory achievement—a false
summit of sorts.
implications, and I know why we would Cisco exec, who’d had decades of experience in
do that. However! Can we stop and think the industry. With a devilish-seeming smile, he
about what happens if we destroy the handed us a tear sheet of features and functions,
trust our users have in the system?” jam-packed with detailed telephonic terminology
and requirements that reflected zero compassion
I witnessed the very opposite of this attitude for the audience that mattered most—the user.
at the beginning of my last project at IDEO. I We hacked through this dense jungle of clueless
led the team that designed Cisco’s first line of priorities to arrive at something easy to use, even
VoIP desk phones. This was their first phone. if it was your first time making a call.
Their first product that wouldn’t live on a rack The 7900 series became the bestselling and
in a data center or a closet, but would instead be last great desk phone in history because my team
far more personal. I mean, this is a product that and I went out of our way to understand the
literally touches your face throughout the day. existing beliefs that new users were bringing to
And when Cisco came to us in 1998, they didn’t the table. We met them where they lived, rather
have any idea how to develop a consumer product than expecting them to come visit our narrow
or really anything with a user interface. What they assumptions. Doing this during the design
did know about phones they had learned from a process requires an uncanny ability to forget
former Nortel marketing executive, who they’d everything you know about the problem and the
hired a few weeks before retaining us, in order to solution you’re developing.
drive the functional spec from their side. I’ve worked with some of the most talented
I’ll never forget our first meeting with this new designers out there. What distinguishes them is

that every time they look at something it’s as if end product, no matter how trim and polished.
they’re seeing it for the first time—not through the No, a company where design is truly a core
eyes of someone who has been grappling with the value is one that will value creating a process for
challenge for days or weeks, but through the eyes creating great products and experiences, time
of a bright and shiny new user. It’s having this and again.
perspective that will distinguish companies that It’s rare that massive new product categories
get design from those that don’t. are launched at established companies. But
after Jobs returned to Apple as CEO in 1997,
he did it five times. It was because he had
constructed a process—a set of plans, patterns,
The greatest creation in nature isn’t any one and protocols—for repeatable genius. Because,
species—but the process of evolution by natural once again, design is more than aesthetics—it’s
selection, which has produced, in Darwin’s a methodology for solving problems, which
words, “endless forms most beautiful and most is different from the analytical approaches
wonderful.” The greatest invention in history that business or technical entrepreneurs are
isn’t any one device—but the scientific method, usually taught. Designer founders see design
a process that has given us all the marvels of as a process, a series of conversations and
the modern world. Likewise, what will mark a collaborations between various relevant parties.
company as being design-led won’t be any single One designer founder who certainly does is Evan
What really matters for a modern company is

building design processes—lightweight methods
and processes for problem-solving, creativity,
and iteration.

Sharp. He believes that, “The disease in our “Seven Universal Stages of
world is seeing the product as the goal, not the Creative Problem-Solving”
continuous journey.”
Some astute readers may have noticed that
I’ve thus far avoided referring to this method as
“design thinking.” There are reasons. For one,
I believe that design thinking, as codified and
popularized by IDEO, could use a little editing.
More on this in the next chapter. The more
significant reason that I’ve shied away from the
term is that the concept goes back decades, and
there are as many definitions of design thinking
as there are Post-It notes at a 3M factory.
What I came to realize, through speaking with

so many design minds, is that, though the
specific terminology varies, design thinkers IDEO’s more famous five-step
of various stripes are speaking a common set design-thinking process
of fundamental truths about what design is.
For example, The Universal Traveler’s “Seven
Universal Stages of Creative Problem-Solving”
doesn’t sound all that dissimilar to IDEO’s more
famous five-step design-thinking process.
Nor is my conception of the design
methodology for startups so different from these
central verities. I think a startup’s design process
needs to begin by really trying to understand the
users’ experience and what the problem or

On an episode of the design
podcast 99% Invisible, host
Roman Mars said,
I think that’s exactly right.

In this ever more uncertain,
constantly shifting century of
the designer, companies and
especially startups can never
stop learning and adapting.

opportunity truly is, not just the task at hand or about a problem that’s more interesting than the
the assignment given. It needs to generate ideas final solution.”
collaboratively. Turn those ideas into prototype As I wrote earlier in this chapter, a company
solutions. Test your solutions in the real world, that’s empowered by this type of design will
and then refine them. be transformed. MBAs and engineers are
As a side note, I think there should be taught to identify the opportunity set, find
prototyping with purpose. That is, I think it’s certainty in numbers, and optimize accordingly.
important to be explicit about what specific But in an organization in which design processes
question you’re trying to answer with your are pervasive, they’ll come to understand
prototype. If your question relates to user that not all problems should be treated as
activation metrics, build a handful of lightweight engineering problems. Some need to be
landing pages to test a range of options. If your broken apart, reframed, and put back together
question can be answered with a simple beam in a new synthesis.
calculation, do the math instead of building a If everyone in your startup is at least a little
prototype. Remember: prototypes aren’t the bit of a design thinker, the creative confidence
point—feedback is. of your business will increase and you’ll be
Apart from that, my stations of design, as I able to arrive at more innovative solutions. “If
said, are not so different from the process that a company is ultimately in the service of trying
other design thinkers have described. They’re to solve problems,” said Nate Weiner, “I think
just slightly different routes to the same place. designer founders are able to … apply that
But the approach is incredibly effective at freeing process and that experience in any [technical,
creativity—and it scales. The same principles can design, or business] conversation.
be used to design chairs, shopping carts, electric Of course, big ideas aside, there will be
cars, emergency-room procedures, customer mundane particulars of your process to be
experiences, organizational structures, even worked out. At Apple, for example, big projects
other processes. “I think I went to Stanford for are broken down into smaller tasks, which are
product design,” Kris Woyzbun, cofounder of assigned to teams, and those tasks are further
Tablo Inc., told us, “because I still had that idea broken down into subtasks assigned to a “directly
of a world where I design things….But then the responsible individual.” (Stay hungry, stay
d.school opened my eyes to this way of thinking foolish—but learn to project manage!)

The product teams at Airbnb are organized We have a playbook for everything.
around the customer journey. According to A sales playbook, success playbook.
product manager Sarvesh Regmi, teams can It’s a Google doc that we and our
touch any part of the product experience and customers co-create. Like a shared
conflicts are resolved—in design thinking bible. [Playbook is] a nicer way of
fashion—by working out the assumptions saying process. Rather than saying I’m
behind competing approaches, framing them going to follow this process, it’s saying,
as hypotheses, discerning the unknowns, and Look, we have a playbook and
testing via experiments. everyone at the company contributes
their learnings to the playbook.
The point is, every company is different

At Abstract, a collaboration platform for and you will have to find your own process for
designers, Josh Brewer’s process for his repeatable genius – one rooted in the principles
designers is all about communication. Small, of design thinking. But a process you must
lightweight signals to one another that are easy seek, because design no longer dead ends with a
to digest and incorporate into decision-making. product or transaction.
Another benefit is that, as these communications On an episode of the design podcast
are shared with all, everyone feels connected 99% Invisible, host Roman Mars said, "For
and involved anything complex, perfect design is a moving
At Particle.io, a platform for IoT developers, target." I think that’s exactly right. In this ever
they try to empower their employees so that more uncertain, constantly shifting century
“everyone can do design work and design-y of the designer, companies and especially
things.” Nobody works exclusively on hardware startups can never stop learning and adapting.
engineering, for example; rather, team members Everyone in a business needs to learn to think
shift around to address various product needs, more like a designer, because the Japanese
which ensures there’s no lost productivity when principle of kaizen—or continuous innovation
hardware hits a lull in their cycle. and improvement—applies to most every
Tiffany Chu reported to us that at Remix, organization now. And a modern enterprise
the urban-planning startup she cofounded, should, at its core, always be designing

You have one or two designers. They're both You have a design team of 2-5 people. An You have a Head of Design. Design managers You have a VP of Design, there are leaders for
generalists who are able to go deep in their experienced designer is stepping up to lead. and leads are building their respective teams. different design divisions, with layers of
CO M PA N Y S TAG E areas of expertise. Your team brings in Your team is mostly composed of generalists In addition to specialists, you support management within each, you have built out
contractors to fill in the gaps. with unique backgrounds, and you start hiring junior designers seeking mentorship creative teams around areas most critical to
specialists to support the company's goals. and growth opportunities. your business.
You have no agreed upon design process. Your team has started documenting their You have style guides for different areas of Your team's process is clearly defined and all
There is no standardized workflow. Check-ins, design decisions. You have a working style design maintained by product/ engineering/ designers use it as a guiding framework for
critiques, and reviews are ad hoc, if they even guide and a clear way to share files with fellow marketing. You have a process in place to their work. You have defined principles and
PROCESS happen at all. designers and handoff assets to engineers. onboard new designers to your team, values, clear owners of the visual language,
& D O C U M E N TAT I O N equipping them them with the tools they need interaction standards, and more. The team
to work effectively. shares work regularly and actively seeks
feedback on their process.
Your design team's methods of communication In addition to face-to-face conversations, your Your design team has agreed upon rules for Your team has done facilitation training
By Heather Phillips, Design are fluid, most conversations happen in person, design team now has different modes of communicating effectively. Designers are clear and difficult conversation training. Designers
Manager at Designer Fund. CO M M U N I C AT I O N
and in collaborative working sessions with your communication—Slack for quick feedback, in their feedback and understand how to give follow well-defined rules around critique—
cross-functional team. Wake for in-depth feedback, etc. You're still it so people are receptive. In the broader designers are clear about asking for the type
& CO L L A B O R AT I O N learning to how to communicate most company, people are open, regularly seeking of feedback they want. You effectively
This version of the framework effectively within your growing team. feedback and input from design. communicate with external partners about
was presented at Source, a design how to best work with design.
leadership summit hosted by
You don't have a formal critique process. Your design team has time set aside each week Your team hosts critiques at key points of the Design managers are responsible for scheduling
Designer Fund and Foundation Designers help facilitate feedback from for critiques in which they share progress and design process, and invites key stakeholders to and facilitating critiques for their respective
Capital, on February 10, 2017. other members of your team in addition to elicit feedback from other designers. participate. These critiques have a schedule for teams. The design team proactively assesses all
seeking outside perspectives from designers Impromptu conversations are happening in who is presenting and clear rules for work produced by the company, even work
CRITIQUE in the community. between weekly critiques to keep momentum. engagement. You use this opportunity to outside of design, and has a process in place for
& FEEDBACK educate non-designers on how to give improving it. Works in progress are visible to the
productive feedback. In addition, you introduce broader company by way of pin-ups, internal
more scalable methods of collecting feedback tools, and design team announcements.
over Slack, Wake, etc.
You have opportunities to learn from your Your design team has budget for professional You bring in industry experts to develop your In addition to professional development
colleagues, but there's no other design development to put towards internal team. Designers participate in opportunities opportunities made available to your entire
DEVELOPMENT expertise at the company so you have to workshops, coaching and attending external like Bridge and are encouraged to set up plans design team, your Head of Design has
& COACHING find it elsewhere. conferences and classes. for skill development with their managers. a dedicated leadership coach, and the
company offers similar services to
up-and-coming design leaders.
You have yet to hire an in-house recruiter. You have an in-house recruiter to help You have an in-house recruiter focused Design roles, levels and compensation are
Designers on the team are responsible for with sourcing and scheduling, but the on building your design team. You have clearly defined. You have a dedicated design
preparing job descriptions, defining the design team drives the interview process created a clear hiring plan and corresponding recruiter and a refined process for assessing
RECRUITING interview process, and sourcing from their own and defines assessment criteria. Designers job descriptions. Information is readily candidates. Interviewers have undergone
& LEVELING design networks. at your company are active in the broader available about your design team's culture training—questions and design challenges have
community and use their connections as a and process to share with candidates and been vetted to avoid bias. Your design team
source of referrals. attract inbound applicants. has a website to showcase the team and ethos.
Your entire company still fits in one room. Your design team sits together, ensuring plenty Designers have a 'home base' for heads-down Design is influencing the space for the entire
As a designer, you're seated next to the of opportunities to collaborate with one work. There is a design team common area for company. This impacts decisions around the
SPACE engineer who's building what you're designing. another, as well as cross-functional teammates. dedicated design sprints. Designers have floorplan, furnishing, the proximity of different
& S E AT I N G You're likely in a co-working or temporary You have areas to pin up work in progress, and access to a resource library and tools for departments and how they interact within the
office space, you haven't invested in your hold collaborative work sessions. You have a printing, prototyping, and other forms of space. Design permeates the entire culture.
environment in a meaningful way. design library with resources and inspiration. creative expression.

Now, I think that design thinking is one of the most important
“dangerous ideas” of the st century. Its impact on product
design, on how organizations go about solving problems, and
on how we live our everyday lives has been profound.
But it’s been  years—a generation—since David Kelley had
his epiphany to stop calling IDEO’s approach “design,” and
start branding it as “design thinking.” And a lot’s changed.
ach day now we generate 2.5 In the intervening period, design thinking
quintillion bytes of data—from internet has enjoyed endless press coverage. Universities,
posts, mobile phone activity, IoT businesses, non-profits, and science labs run
sensors, purchase transactions, and more. So much design sprints based on its principles. The
data that over 90% of it in existence was created in concept is even taught at some elementary
just the last two years. Two years of Twitter tweets schools. It’s perhaps inevitable that when an
produce more words than are contained in all the idea gets this popular, it becomes a victim of its
books ever printed, combined. This year, 85% own success. And I think, to some degree, this
of the 1.2 trillion photos taken will be captured has happened with design thinking. People who
on smartphones. The first camera phone was are barely trained in the process become
manufactured in 2000. At about the same time that so-called design-thinking instructors.
David’s “design thinking” lightbulb was going off, Practitioners struggle to define the term clearly.
in 2002 a full human genome sequence cost $100 And, worst of all, some of the core tenets of
million. These days it can be done for $1,000. And design thinking have, in my observations, been
by 2020 it’ll cost less than a movie ticket. watered down or misapplied.

Map of fiber-optic connections.
What’s more, as the world has grown more in other words, that design thinking needs
complex, I believe that the version of design tuning up and updating (Design Thinking 2.0,
thinking that we’ve been working with for the anyone?). Therefore, in the spirit of suggestions
past generation needs to evolve, in order to for further thought/study/debate, let me offer two
account for these dramatic changes. I think, directions for a critical refresh

I’ve had my fill of empathy. Or to be more specific, all the
talk of empathy in recent years. Don’t get me wrong. I’m all
for a human-centric approach to design, one that puts the
user first and attempts to understand how the world looks
to them, as I’ve argued throughout this book. But in design
circles and many other fields, empathy has become little
more than a buzzword which, at its most vacuous, seems to
mean nothing more than a soft bleating sound made when a
small animal is in pain. At its most cynical, it’s a Silicon Valley
euphemism for market research.
s one colleague pungently put it, community of design thinkers should self-impose
“Empathy is a rathole.” I’m not sure I an 18-month moratorium on using the word.
would go quite so far, but for the sake There are other reasons to be cautious of
of semantic integrity, alone, I think that we as a being overly led by empathy. For one, empathy

as an emotion has its limits. As the recent broadcasting. Empathy in design has gone from
presidential election underscored, there’s only an outward-facing action to an inward-turned
so far the average tech worker in Silicon Valley affect. I think it might be too late to protect the
can go in understanding the thinking of Trump design-thinking denotation of the word from the
voters in the Rust Belt and South, and vice versa. layman’s definition. Regardless, I would urge
When we’re talking about building things to be us as a discipline to practice rigorous evidence-
used by hundreds of millions of people, there’s based compassion, rather than trying to feel
no way a highly paid 20-something white male people’s pain.
designer at Uber or Instagram or Google can In my own experience working with designers,
reasonably hope to empathize with end-users in it’s struck me that decisions were often made
parts of the country or world with which he’s had at the end of sentences that began with phrases
no meaningful contact. To truly understand this like "I believe" or “I feel.” But today, we don’t
audience, he would have to go live among them: have to rely solely on gut emotions like empathy,
interview them; gather intel on their behaviors, and we can go even further than ethnography.
lifestyle, and concerns; probe how they make use We can let the data tell us what will work and
of the products he makes. what won’t. We can use tools like Optimizely to
“Empathy” was David Kelley’s shorthand test multiple designs in real-time; to compare
for this type of ethnographic research. And, to alternative concepts in minutes and hours rather
be fair, that’s what some design thinkers still than weeks or months; to let data weave its way
have in mind. But over time, through overuse, into the design process. At Airbnb, for example,
when most designers talk about empathy, they’re using structured data to help ensure that
they don’t seem to me to be referring to fact- the quality of the homes is improving, to create a
gathering at all, but something more like feeling- better experience.
Build something, put it out in the world, collect

data, collect feedback, make adjustments.

Most designers and many engineers have heard new ideas. And, most importantly, Joe didn’t give
of the concept of "T-shaped" people—individuals up because he is insane had a vision. In the final
with depth in a given domain complemented by a analysis, no amount of empathy is a substitute for
familiarity and, at a minimum, a healthy respect having a vision.
for the adjacent disciplines required to build and In fact, too much empathy can kill your
launch a successful product. But if you want to company. If you think design is going out, ex ante,
build enduring companies and really earn your asking users what they want and then trying to give
seat at the table, I think you need to be π-shaped. it to them, you will fail. As Jobs said, "It's really
That is, you need to have depth in both the hard to design products by focus groups. A lot
creative and the analytical. You need to be left- of times, people don't know what they want until
and right-brained, empathetic and data-driven you show it to them." Or, as I sometimes like to
This isn’t to say you should always defer to the put it, invention is the mother of necessity. Build
data. Algorithms can’t fully account for the human something, put it out in the world, collect data,
element. Joe Gebbia said that if he had listened collect feedback, make adjustments. Build; don’t
to the analytics in 2008, when Airbnb had zero ask. Listen to your users in real-time, but don’t be
growth, no investors, and a lot of credit card debt, a slave to narrow consumer cravings.
he would’ve shut the service down and cut his Now, not every idea hits its target, and of
losses. For months, the data were telling him this course, there are plenty of products that don't
idea was never going to take off, and he should go deserve to exist. But I can tell you for sure that the
work on something else. But he refused to listen most successful startups are those that created the
to the data. In a way, he was refusing to listen to markets that they ultimately owned. And at one
the users, as well, because they were telling him time in their life, many—if not most— onlookers
that they weren’t very interested in what he was thought it was a crazy or stupid idea. These
currently offering. Instead, he soldiered on and did founders—like Jobs, like Joe—navigated their way
still more things that couldn’t be defended by the through the fog by figuring out when to listen to the
numbers—like fly to New York to try to plumb the market and when to listen to their inner compass.
causes underlying their lack of growth, in order to So, have a vision of the future that you want
save the company. Because the data can tell you to bring people into the light of. Then provide
what’s happening, but they can’t tell you why it’s the one thing that we as designers are best
happening—especially when it comes to radical capable of providing: creative leadership

In fact, too much empathy can kill
your company. If you think design is
going out, ex ante, asking users what
they want and then trying to give it
to them, you will fail. As Jobs said,

The world is now a profoundly interconnected place.
Here are some additional factoids to illustrate how we
touch, and are inextricably in touch with, each other at every
moment. We are halfway to connecting everyone on the
planet, with . billion internet users worldwide. In the U.S.,
% of - to -year-olds use the internet. Smartphones have
become ubiquitous: roughly half the world’s adult population
owns one and it’s projected that by  the figure will climb
to %. WhatsApp was founded less than a decade ago, but
now traffics in  billion more messages a day than the SMS
global text-messaging system. And never mind six degrees
of separation—just off the top of my head, I’m one degree
removed from both Barack Obama and a Bhutanese Sherpa.

e live in a massively, intricately as a set of relationships and consequences
interconnected global system. that are at least as important as the individual
Your startup will be enmeshed in components themselves. It emphasizes the
this system. And it’s increasingly impossible to emergent properties of the whole that neither
be designers (or human beings) without taking arise directly, nor are predictable, from the
into account how we affect and are, in turn, properties of the parts.
affected by all the moving pieces of this organic Systems thinking can be used to explain and
machine. “The more complex an organism is,” understand everything from inventory changes
says artist and teacher Adam Wolpert, “the in a supply chain, to populations of bacteria
more capable it becomes. And the more capable and their hosts, to the instability in Syria, to the
it is, the more it can address challenges and seemingly irrational behavior of certain elected
seize opportunities. The downside of that is, the officials. The vocabulary of formal systems
more complex it becomes, the more vulnerable thinking is one of causal loops, unintended
it becomes.” The challenge for designers, consequences, emergence, and system dynamics.
increasingly, is learning how to balance the And practicing systems theorists employ tools
production of ever more complex capability such as systemigrams, archetypes, stock and
against the threat of a resultant breakdown. flow diagrams, interpretive structural modeling,
That’s why I think design thinking, which and systemic root cause analysis—all of which is
emphasizes solving problems holistically, waaay beyond the scope of this book.
needs to look at a bigger whole by incorporating For the purposes of this treatment, I’ll simply
another body of thought: systems thinking. introduce the Iceberg Model and briefly discuss
Systems thinking isn’t new—though most two key concepts in systems thinking, emergence
designers I’ve spoken with are unfamiliar with and leverage points.
it. It’s a mode of analysis that’s been around for
decades. But I think it has newfound relevance
for today’s everything-is-networked, Big Data
world. Systems thinking is a mindset—a way of The Iceberg Model is a helpful way to explain the
seeing and talking about reality that recognizes concerns that drive systems thinking. Events are
the interrelatedness of things. System thinking at the top of the iceberg. They’re incidents that
sees collections of interdependent components we encounter from day to day—the hurly-burly

R E A C T. . .
WAT E R L I N E
OBSERVE...
C R E AT E . . .
VISION / MISSION

Systems-savvy designers will know
the real answer is to unearth what
patterns or assumptions are generating
those suboptimal behaviors. Not just
what happened and when, but how
and why these things happened.
of life. Patterns are the accumulated habits or driving the events we’re captive to. It’s there,
behavioral “memories” that result from repeated, at the tip of the iceberg, that we expend most
unconsidered reaction to events. Systemic of our energies and attention, and like the
structures are how the components of the system Titanic, it’s there that we run aground because
are organized. These structures generate the we don’t see the truth of the problem—the
patterns and events that confront us. Mental variables and influences lying below the surface.
models are the assumptions we have about how We take actions without understanding the
the world works; they give birth to systemic impact of those actions on the system, making
structures. Values are the vision we have for our the situation worse.
future—what we aspire to. They’re the basis for As an apocryphal illustration, let’s say, there’s
our mental models. a cup of coffee made at Philz that isn’t perfect
Mostly we live at the level of events, because (WUT!). That would be an event. A pattern
it’s easier to notice events than it is to discern would be noticing that there’s a higher frequency
hidden patterns and systemic structures. Even of imperfect coffees that are produced during
though it’s underlying systems that are actually shift changes from the morning to afternoon

Systems thinking is a mindset—
a way of seeing and talking
about reality that recognizes
the interrelatedness of things.
System thinking sees collections of

interdependent components as a set
of relationships and consequences
that are at least as important as the
individual components themselves.
It emphasizes the emergent

properties of the whole that neither
arise directly, nor are predictable,
from the properties of the parts.

to evening barista staff. Perhaps the systemic psychologist Philip Zimbardo puts it, rather than
structure generating this pattern of defective bad apples. Not just what happened and when,
coffees is that the shift changes are scheduled so but how and why these things happened.
as there’s no overlap between the incoming and Adam Wolpert, my systems-thinking
outgoing teams of baristas. Obi-Wan, shared a real-life example with me
The mental model that the baristas hold leads of putting this mindset into practice. He was
them to believe that they’re only responsible asked to help ameliorate fraught conditions
for the Canopies of Heaven and Philharmonics at a cohousing development in Sebastopol.
that they make, not the team after them. And The development, which was made up of 35
say, the value that drives that belief is one of people living in 22 units, was riven with conflict
competition—of wanting to make better cups and coming apart. When Adam arrived on the
of Philz than the other shifts, and therefore not scene, he conducted a systems mapping exercise
being concerned about the pour-over apparatus to determine what the boundaries and priorities
being properly cleaned, or the beans correctly of this landscape looked like. What soon became
ground and apportioned, at the end of a shift. apparent to him was that…
End nightmare scenario. Back to your
regularly scheduled Mint Mojitos. This thing is not a thing. It’s actually
a couple of things. There’s one
boundaried system of people who want
to live in a community, and be really
It’s usually the case that moral character or connected and engaged … and really
human error are blamed for what are really make a family. And then there’s
system failures. The people who made the another group of people who want to
mistakes—the “bad apples”—need to be live in the neighborhood, and they
reprimanded, retrained, or fired. But systems want to be good neighbors and live in a
thinkers understand that these are symptoms and cool place … but they’re not interested
not causes. Systems-savvy designers will know in being an intentional community….
the real answer is to unearth what patterns or
assumptions are generating those suboptimal The people who … just wanted to live
behaviors—the bad containers, as Stanford in the neighborhood, they were being

vilified by the intentional-community arise that exist only in the system as a totality,
people….They were being thought of and not in its disparate components, making it
as slackers, of not showing up … But impossible to understand the system without
if you really looked at it from their looking at the whole.
point of view, you saw this whole other You can’t understand how we get to an
framework. Which was really what the anthill by looking at a single antenna or thorax.
whole needed to come into a healthy A Tesla driving down 280 is an emergent
balance and move forward. property of the innumerable parts that go into
making the car—as well as the national grid of
Two key concepts to understanding systems recharging stations that had to be built and the
thinking. The first is emergence. What makes a web of regulatory oversight that needed to be
system a system rather than just a collection of navigated. In the inextricably connected world
parts is that the components are interconnected we now live in, it’s no longer possible or wise to
and interdependent. Their interconnectedness solve for the part without due consideration of
creates feedback loops, which change the the sum of the parts.
behavior of the system—in fact, they define the It was an awareness of this reality that led
behavior of the system. Emergent properties Alta Motors, an electric motorcycle startup,
Rather than attempt to design a wholly new,

perfect solution, oftentimes it’s better to find areas
where an incremental change will lead to significant
renovation in the system. The smallest nudge for
the biggest effect.

The challenge is to rise above the distraction of
the details and widen your field of vision. Try to see
the whole world at once and make sense of it.
It’s a heady challenge, yes. But you either design
the system or you get designed by the system.
to delay going to market. “We took a systems- Rather than attempt to design a wholly new,
design approach,” said CTO Derek Dorresteyn, perfect solution, oftentimes it’s better to find
“We optimized all of these things to work in areas where an incremental change will lead to
concert together to get to the goal, which was the significant renovation in the system. The smallest
user experience. If we went to market too early, nudge for the biggest effect.
we would get locked into certain technological “Everything is networked now,” in the
approaches….So we could only make a change world according to Evan Sharp. “All of culture,
in the future by changing three things at once all of communications, it all is going through
instead of just one.” networks.” Therefore, at the scale of seven
billion people, “any small little improvement
you make has massive aggregate value.”
This will cut against the grain of most designers’
So how are designers supposed to address this instincts, because the end-result will likely be far
onslaught of socioeconomic, techno-political from an ideal proposed design, but designing for
complexity? I think the trick is to analyze systems the real world means dealing with the practical
with an eye towards finding leverage points— constraints of that reality and trying to make
the second key concept in systems thinking. refinements in the face of compromise.

Now, I don’t want to oversell systems or for the company. You have to be
thinking. It’s not always possible in real-world looking at many different angles and
cases to reasonably model very complex systems be very agile.
in ways that lead to good design strategies and
outcomes. Systems thinking will also be novel The challenge is to rise above the distraction
and perhaps somewhat jarring to many designers, of the details and widen your field of vision.
because as designers we’re usually laser-focused Try to see the whole world at once and make
on a single, discrete design problem. But when sense of it. It’s a heady challenge, yes. But you
appropriate, applying a systems mindset to either design the system or you get designed by
design thinking will give designer founders a the system. Moreover, while this nonlinear way
powerful tool for circumnavigating the problems of thinking might seem alien at first, rest assured
of the age. Focus on relationships over parts; that it won’t be long before it feels like second
recognize that systems exhibit self-organization nature—because it is. No one put this more
and emergent behaviors; analyze the dynamic beautifully than the late sustainability pioneer
nature of systems in order to understand and and systems scholar Donella Meadows:
influence the complex social, technological, and
economic ecosystem in which your startup exists. Only a part of us, a part that has
Some designer founders, like Moxxly’s emerged recently, designs buildings as
Gabrielle Guthrie, understand this even without boxes with uncompromising straight
training in systems thinking: lines and flat surfaces. Another part of
us recognizes instinctively that nature
The outcome could be a physical designs in fractals, with intriguing detail
product, a system, or culture…. on every scale from the microscopic to
To be a designer founder, you have to the macroscopic. That part of us makes
care about the broader situation. Gothic cathedrals and Persian carpets,
It’s a Russian doll, or a “Powers of symphonies and novels, Mardi Gras
Ten” thing. You’re working on a costumes and artificial intelligence
particular thing, and you think about programs, all with embellishments
how it fits into the mindset of the larger almost as complex as the ones we find
team, how it works with your users, in the world around us

Grace eludes us. The world is an imperfect place.
Imperfect, ignorant, and troubled. Our planet hit its hottest
temperature on record in , smashing the record set the
year before, which broke the one set in . More than
 million people remain unemployed globally following
the economic crisis of . Your country elects a vulgar,
illiberal demagogue to the presidency. The internet is an
ocean of molten partisanship and rank disinformation.
Your baby brother is felled by a rare mitochondrial disorder
and dies two weeks after his nd birthday.
or me, Mike embodied one of the core and the value of persistence in the face of adversity.
themes of this book: the power of scale. In a conversation I had with him right at the end, he
At 4’11”, 100 lbs., my brother always said: “Let’s go. Let’s get out of here.” His premature
demonstrated strength that far exceeded his size, death put so many things into perspective. It was
and compassion that far exceeded what is common. a reminder of what really matters in life, including
He went on grand adventures—cruising the Alaskan taking on challenges of import and scale.
waterways, heli-hiking the Bugaboo Mountains, As the world grows more complex and
seeing the Great Pyramids of Egypt. He understood uncertain, I believe that designers have both a
the role of kindness as a massive force multiplier, moral obligation and a unique ability to take on

the great challenges of our time. To address real- our elevation rather than our degradation, where
world problems, rather than bury their heads in the all our fellow citizens are respected and would-be
pixelated sand. I’m not talking about building apps tyrants resisted, where the undefended and helpless
that make it easier for bros to have a good time on everywhere are given succor, and where the Earth
Saturday night. I mean helping to solve problems that holds us is safeguarded.
of consequence. I reject half measures. The Universal Traveler
Most of the calamities that we face are systemic describes creativity as “constructive extraordinary
ones, which have been caused by an insufficient behavior.” And that is what I ask of you—emphasis
understanding of, or an utter disregard for, what is on “extraordinary.” Find creative opportunities to
human. For how people engage with and impact effect large-scale positive change. Today, you have
each other and our world, and are impacted in the tools and no excuses. Put your design powers to
kind. Most of these woes could be alleviated, even epic use. Take dragon-scary risks, build giant-size
cured, by building solutions that are truly human- ventures. I don’t want you to touch up society’s
centered. And no one is better equipped to do that great afflictions with a magic wand. I want you to
than designers. slay them with a sword.
Putting aside the fancy definitions, design to me If you’re holding back, then the only thing
is ultimately something fundamental and optimistic. you’re fighting is yourself. If you’re waiting for
It’s the predilection to investigate and understand. someone to give the word, then consider the
It’s the compulsion to give form to ideas and to word given. And if you fear you’ll get lost in the
make sense of disorder. It’s the ability to amend the woods, you’re mistaken. There is a diverse and
imperfect. I’ve felt its pull, like a primal force, from affably weird community of designers and designer
the moment I stacked my first LEGO brick as a founders willing to help guide you, including me.
child. And when I see young designers at work now, You won't walk alone.
I can hear it calling to them, as well. These years ahead will be trying ones, but, to
But with this particular power, comes a borrow from Clarissa Pinkola Estés: “My friends, do
particular responsibility. Yes, the world is flawed not lose heart. We were made for these times.” Take
and benighted, callous and unjust. My challenge the spark that’s within you and the skills that you’ve
to you is: Design better. honed, and use them to light up the whole damned
Build a world where ordinary people feel like planet. Build a finer, kinder, wiser, more equitable,
they have a chance, where technology leads to more beautiful, more joyful world. Design better

Mike (left) and Steve take on the world.
Build a world where ordinary people feel like

they have a chance, where technology leads to
our elevation rather than our degradation, where
all our fellow citizens are respected and would-be
tyrants resisted, where the undefended and helpless
everywhere are given succor, and where the Earth
that holds us is safeguarded.

These years ahead will be
trying ones, but, to borrow from
Clarissa Pinkola Estés
Take the spark that’s within you and the

skills that you’ve honed, and use them to
light up the whole damned planet.

ly in the Spring of 2016 did The Way to eyes to the power of design and for devoting your life
Design, which I’ve had on a slow boil for to inspiring young minds.
several years, become real. It was then This project would have been impossible without
that we pulled together a team at Foundation Capital the unsel sh input of scores of designer founders,
to treat the initial question as a design challenge. I owe design scholars, and designers. Starting with model
them my first and biggest thanks. Thank you, Melissa designer founders Joe Gebbia and Evan Sharp. Design
Miranda, for being an incredible partner on this legends and dear friends Diego Rodriguez and Bernie
project and leading the designer-founders research. Roth. As well as the invaluable contributions of Adam
Thank you to Sang Ngo for the gift of your synthesis Ting, Adam Wolpert, Adrian James, Alexis Finch,
and prose, and for making me sound 100x better than Barry Katz, Bob Baxley, Caleb Elston, Daniel Scriv-
I ever could on my own. Thank you, Meg Sloan, for ner, Dave Baggeroer, David Sherwin, Deepak Thomas,
your insight and for pushing us all to think bigger. Derek Dorresteyn, Gabe Trion, Gabrielle Guthrie,
Thank you to Catherine Harrell for raising the excel- Gentry Underwood, Greg Duffy, Ian Taylor, Jesse
lence quotient on everything you touched. Thank you, Genet, John Proksch-Whaley, Jon Fox, Jon Logan,
Melissa Costello and Robyn Basso, for making sure Josh Brewer, Junji Hase, Katy Mamen, Keenan Cum-
The Way to Design machine ran smoothly. mings, Kris Woyzbun,
Thank you, Ben Blumenfeld and Enrique Allen, Kyle Doerksen, Loren Baxter, Marc Fenigstein, Mark
for sharing, so generously, your own experiences in Kawano, Nate Weiner, Ravi Akella, Richard Whitney,
support of designer founders. Thank you, Christopher Santhi Analytis, Sarvesh Regmi, Scott Klemmer,
DeLorenzo, for the joyous and brilliant illustrations. Shanna Tellerman, Shireen Yates, Ti any Card, Ti any
Thank you to my brother Mike for your grace and Chu, Tricia Choi, Wei Lien Dang, and Xander Pollock.
grit, and for being my first fellow traveler in life. To Thank you for sharing your stories and your wisdom,
Steve Jobs for transforming the role of design forever especially when so many of you were in the midst of
and for the better. To David Kelley, for opening my your own crazy- busy entrepreneurial journeys
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This book is dedicated to designers who dare to be

entrepreneurs, and entrepreneurs who want to harness

the power of design.

there’s no tighter place to begin than the , square-foot

Dutch Colonial on Laconia Road that me and my nine brothers

and sisters were all jammed into. My parents turned the

these renovations, we had to figure out how to shower every

of kids to each bedroom.

The Way To Design 6

This elemental compulsion is what and who

fine arts, or industrial, graphic, or user-interface

The Way To Design 7

The Way To Design 8

The Way To Design 9

The Way To Design 11

The Way To Design 12

You can use your mutant

The Way To Design 13

on the back cover of The Universal Traveler, one of my

favorite books. Written by Don Koberg and Jim Bagnall,

two design professors at Cal Poly, and first published in

, The Universal Traveler is part self-help manual,

part treatise on creativity, part design workbook. There

are charming sections on things like, staying open to

“off-the-wall” ideas in Brainstorming (capitalized) sessions.

was introduced to it as an engineering About a decade later, after my run as a product

The Way To Design 15

VCs like me are used to asking, Who

The Way To Design 16

To reinvent yourself from

To build your startup into

To remake the world

And I’ve this book

The Way To Design 17

The Way To Design 18

focusing almost single-mindedly on an organization’s

technical prowess. It meant having an unimpeachable

technical founder, 10X engineers, and a relentless

devotion to computing dominance. What truly mattered

about consumers’ interaction with technology was

that it be fast. Expending valuable time on anything

else—particularly design—was evidence of distraction

from the real work of the company.

The Way To Design 19

The most fundamental software infrastructure

The Way To Design 20

The Way To Design 21

Free and easy-to-use CAD

The Way To Design 22

its scope and meaning have changed. When most laypeople

Dieter Rams stereo receiver, a Noguchi coffee table, one of

the homes featured in Dwell, a Giugiaro concept car, maybe

a well-turned brand logo. I’m a craftsman at heart and I

honor this form of design. But “design” has come to mean

much more than craft.

The Way To Design 24

The Way To Design 25

The Way To Design 26

century will be the designer’s century, because I believe