Intro
Susan Kare, the iconographer who designed the original Macintosh's icons and system fonts, walks through how she got hired with no computer experience, how the Happy Mac, the bomb and the command key symbol were arrived at, and what four decades of logo, icon and avatar work for Microsoft, General Magic, Facebook, Pinterest and others taught her. She closes with the collection of advice she keeps from the people she has worked with, Paul Rand and Steve Jobs among them.
Guest: Susan Kare, iconographer and designer, the Macintosh artist on the original Mac team, with a PhD in art history
Published: 28 August 2026 on Y Combinator
Episode page | 52 min
Key Takeaways
An art history PhD and a stack of library books got her the Macintosh job
She had been welding a life-sized razorback hog for an Arkansas museum, and says nobody asked her a question about font design
The graph-paper notebook she took to the interview is now in MoMA's permanent collection
Simplicity in an icon is what makes it universal, not what makes it cheap
"the less detail you have, the more universal something is"
A face with detail looks like somebody else; a plain one lets everyone project themselves onto it
The bomb icon was drawn on the promise that no user would ever see it
A customer called Apple to ask whether her computer was going to explode
Don't draw a product; draw a metaphor
The three-and-a-half-inch floppy for save and the sprocket-fed paper for print both dated badly
The command key symbol came out of a library book, and turned out to be a Swedish castle
Steve Jobs killed the Apple key because he would not have "a bunch of apples" on a menu
Constraints are a starting position, not a loss
16 by 16, black and white, no undo and no shapes in the icon editor
Cute outsells expensive when people are spending their own dollar
Diamond earrings and a Rolex lost to teddy bears, hearts and penguins in Facebook's gift shop
Paul Rand refused a five-way logo contest and charged NeXT $100,000 for one logo instead
Jobs had offered five firms $15K each; Rand's version is what happened
A logo should do something to the name of the product rather than attach a random symbol to it
Steve Jobs's worst advice was to skip the Apple stock, and his second worst was to stop making things
She took the creative director job and went back to the pixels anyway
From Welding a Razorback Hog to the Macintosh Interview
Kare frames the Macintosh group as a startup that happened to sit inside Apple, and says the experiences resonate with what the room is building now
Paul Rand set the frame for the whole talk. The designer behind the UPS and IBM logos told her to "always focus on making things meaningful and memorable," which she reads as: have a good idea and the form will follow
"I was a total art major, didn't know anything about computers" — she had no technical background when she joined the Mac team as its artist
"Before I went to Apple, I was welding a life-sized razorback hog for a museum in Arkansas." She thought she was living the dream in her garage, but it was lonely, and it "made me hungry for working with a team"
Andy Hertzfeld, a high school friend and a system software programmer at Apple, knew she had worked on the yearbook and liked art. He showed her a display with no case and asked her to interview on "some small symbols and some typefaces"
Her typography experience was Letraset rub-down type for exhibit labels at the Franklin Institute Science Museum in Philadelphia: "I could do it really straight and get the kerning right"
"I had a PhD in art history, so those were my credentials."
She borrowed typography and font sample books from the Palo Alto library and carried them into the interview under her arm "so I would seem as if I knew what I was talking about"
Hertzfeld asked for bitmap-style examples drawn on graph paper without specifying what to draw. Some of those random sketches "slightly influenced what we ended up using in the software"
She got the job and says nobody asked her anything about font design. The notebook of early icons she took in is now in MoMA's permanent collection: "So definitely hang on to your stuff."
A Computer Anyone Could Use, and the Constraints That Came With It
On her first day she was shown a screen and told it was her job to improve it: fonts, plus round rects on a drawing of a five-and-a-quarter-inch floppy drive that could already be clicked and dragged with a cursor, which she found magical
"We definitely changed Do It to Okay, because Do It was a little off-color and people read it as Dolt."
The brief was put to her plainly, that "we were trying to make a computer that anyone could use" — understandable enough that "you wouldn't necessarily need a manual," and friendly, because the software group was evangelical about computers
Constraints are a starting position rather than a loss: "it's good to understand what the constraints are and then be excited about that as opposed to being upset that you don't have a thousand colors"
The working canvas was 16 by 16 pixels, black and white. Early ideas included the lasso, picked as a way to surround an irregular region
An aside she enjoys: the Paris street artist Space Invader "has borrowed liberally from early Macintosh stuff" in his mosaics
Chicago, the Paoli Local, and a Font She Called Ransom
Chicago was the first font she designed, nine pixels tall at cap height. The screen "seemed as if it was all jaggedy," and she tidied it with horizontals, verticals and 45-degree angles. She still winces at the lowercase x
Proportionally spaced fonts were the advance she says she did not appreciate at the time, having seen displays where "the M was really squished and the I was really wide"
"What we didn't realize was that when we designed the calculator, we were designing the first iPod, which also used Chicago"
The Mac shipped with a monospace font plus New York and Geneva, her "Times Roman kind of thing and a Helvetica kind of thing"
"Then I made a font that I called Ransom because it was what kidnappers used to do by cutting letters out of the newspaper so they wouldn't have to reveal their handwriting and get caught."
The city names came from stops on the Paoli local, the line running from the suburbs near their high school into Philadelphia
Jobs overruled the naming on one of his end-of-day walks through the software group: "Well, city names aren't bad, but at least call them world-class cities." Paoli, Wynnewood and Rosemont became New York and Geneva
The Icon Editor, and Portraits Done From Life
Bill Atkinson wrote MacPaint, her favorite program, and she collaborated on its icons and patterns
Atkinson also developed an early scanner, which is how the geisha image got in — from a woodcut Steve Jobs owned
The control panel was animated so the settings would explain themselves. They avoided text "so that it could be international without having to make a different version," using sound and speed instead
Hertzfeld wrote an icon editor so she no longer had to design on graph paper. It had no tools, no shapes and no levels of undo — you toggled bits and saw the icon greatly enlarged next to its 72 DPI size
"You could iterate without an eraser." She calls it a marvel: it generated the hex code for an icon, which she could type in and see on screen
People sat for portraits in 32 by 32 and she still makes them: "There wasn't really a way to get a photo in there at the time or even a drawing, so I just had to do it from life"
She says it is amazing that in a thousand dots, with enough iteration, you can get some semblance of resemblance. Pharrell Williams, Ashton Kutcher and the design leader John Maeda are among the subjects; the first two did not sit
Why the Happy Mac Has Almost No Face
One of her first assignments was an image for the wait while the machine booted, at 32 by 32 because it was only a 128K Macintosh
The computer sat there grinding, and "we wanted something that showed that everything was okay." She is fairly sure the smile came from a button she got when she was about 14
The theory came from Scott McCloud's book about comics, which she says "has so many good insights about user interface too" and came out 10 years after the Mac
A face with a lot of detail "looks like somebody else," while a simple one lets everyone project themselves onto it — "the less detail you have, the more universal something is"
A simple drawing of a pencil can stand for writing better than "a chrome pen with a reflection," because the fancy pen is a particular pen not everybody writes with
"So my bias in icons is a salient detail or two, but don't lard it with a lot of extra stuff." She compares it to a school crossing sign: the two kids could have plaid lunchboxes and shoelaces, but it would cost the instant recognition
The Bomb Icon Nobody Was Ever Supposed to See
She was asked for an unhappy Macintosh in case something went wrong, which she was told was extremely unlikely, and drew one that "looks a little hungover"
She says she could be irreverent because she was told nobody was going to see it. At least, that is what she was told
Total system failure got a bomb, "like a Bugs Bunny type of bomb" — "But unfortunately, people did see this"
A customer's call reached the software group's glass room, the fishbowl. The receptionist said the caller needed to speak to someone about her Macintosh "because the caller was worried that she was looking at a bomb and was her computer going to explode"
"So I felt a little guilt."
Verbs, Nouns, and the Icons That Aged Badly
With only about half a dozen applications, the system was "kind of a verb and a noun": an application icon that looked active, paired with a document that resembled it. MacPaint came first
They had no mindset that there would ever be thousands of applications
The alert icon is a crop of a person rather than a person with a square head, deliberately giving away no gender, age or hairdo
The watch cursor replaced the hourglass because she had only ever seen a sand timer as an egg timer: "Hey, we're in the '80s. Let's update these things."
The print icon is the one she calls a trap. The ImageWriter really did use paper with sprocket holes up the sides, but "It would've had a much longer lifespan if I had just stopped and made it simpler"
The rule she draws from it is not to depict a particular product design. The three-and-a-half-inch floppy for save "obviously didn't age well" — "Better to use a metaphor. Just enough detail."
How the Command Key Got Its Symbol
The dropdown menus used the Apple, and there was going to be an Apple key for keyboard shortcuts, until Jobs came in one evening and said, "You cannot do this." She says he called it an apple farm: "Our logo is precious and we have to respect it. So we just can't have a bunch of apples."
Told the key was now a command or feature key, she found commanding "kind of mean" and the Ten Commandments a pun, so she went back to the library
She found a symbol in a book that was labeled a feature: "it kind of looks like a four-leaf clover that's sort of lucky. It kind of looks like a cloverleaf highway, which might be a way to get somewhere fast" — with the bonus that it was really easy to draw in 16 by 16
She still felt bad that it was abstract, because abstract marks can be harder to remember than something with a metaphor reinforcing the concept
Getting off the plane in Gothenburg, she found the same symbol on Swedish signs marking sightseeing and monuments
Someone from Sweden then told her the sign comes from Borgholm Castle, a ruin dating to 1200 AD that looks from above like a castle with four turrets: "I thought it was fun to find out even after the fact it did look like something after all"
Art History Says None of This Was New
"When you study art history, there's not much new under the sun. People have been making little symbols for a long time."
Hieroglyphics "had their day," and she shows a cartoon arguing they are back
She points at bitmap fonts made long before the Mac — one with about a seven-pixel capital height, another with a character height of about 10 pixels, made "200-plus years before we sat down to make our proportionally spaced fonts"
Carvings combining symbols, text and illustration resemble what the Mac group was doing on a screen
She traces her own pull toward grids to the craft kits children were given to make their parents an ashtray
"I like to think that there were emojis in the 1984 Macintosh, that you could combine pictures with text before there was texting." She hid hieroglyphic-type symbols in it, and says it obviously had a hieroglyphic antecedent
The point of the graphics was never the grid: "It's the metaphor and the idea and the meaning behind everything."
Swatch, and the Case for Showing the Options That Failed
She runs through alarm icon options done for Swatch: a clock, then a noisier clock, then a more literal one, then louder and simpler
A travel alarm clock version she threw out as "way too self-referential. Why would you want a clock on a clock?"
"The point just being, this is so not an exact science."
She likes to show what a client asked for, or what a programmer used as a placeholder, because she has "gotten so many good ideas that way" and can refine them from there
Windows 3.0 in 16 Colors, and the Solitaire Problem
After Apple she did a job for Microsoft on Windows 3.0 and color — only 16 colors, "and some of them weren't very good colors," but red for alerts and color as a second signal made things easier to tell apart at a glance
She dithered the palette because she "wanted to make something that didn't look like a garish chessboard," unlike a lot of the illustration around it
She also did Solitaire, which a lot of people played in the nineties, and had to take it off her own computer so she did not play too much. Slate, she says, thought at the time that Solitaire had made a dent
General Magic's Hallways, and Facebook's Dollar Gift Shop
At General Magic she did the logo and a more literal desktop metaphor: hallways with doors, and file cabinet drawers you could tap to open and fill. She says "the very worst thing we had was jars of text, because why?"
The idea was that you would remember where things were by going and finding them in a logical way. She laughs and winces that the Rolodexes and the phones are gone, and that the product "didn't quite anticipate email" — you could send postcards
At Facebook she worked on a shop where you could not upload images but could buy them for a real dollar and send them to people. She calls it a wonderful project: figuring out what you could draw "that someone would want enough either to have or to share with someone that it was worth spending a dollar on"
It ran for not quite four years with a new gift every day launching at midnight on the East Coast, and by a quarter past they could tell from the first 15 minutes of sales whether it would be a bestseller
She expected expensive-looking things to feel worth a dollar — diamond earrings, a Rolex — and was wrong: "what I learned was that cute trumped everything." Teddy bears and anything heart-shaped sold; the Kiss Mark was the all-time bestseller
"If my life depended on selling a drawing for a dollar, I now know I would draw a penguin" — the multiple limited editions of penguins all sold out
There were collaborations with Britney Spears and other entertainers. Facebook ended the program because it did not want to compete with third parties, "but it was good while it lasted"
Pinterest, Puzzles, Avatars and a Weekend Logo
Her Pinterest icons got a little motion from an animator she credits as terrific, kept subtle "so that it wouldn't get really irritating over time"
Before one company had its real logo, she drew it a trash panda, because the business dealt with trash in a similar way
The National, Amtrak's quarterly magazine, invites artists to interpret its route map; she did pixelated icons for the places you could reach by train
She loves doing logos: Magic Puzzle, whose jigsaws perform a magic trick once finished — "not levitating" — plus studies for the Pikmin Bloom logo and for the game Peridot
"Avatars are so freeing because they can stand for anything." Like the gifts, the point is an array wide enough that someone finds one that speaks to them
She did badges for a fairly new Ledger crypto wallet, which has an attachment opening in the front for personalization, and wanted something a little retro-looking
A logo for a VC firm built on the idea of getting out of the office and working in the mountains came from her friend Dave Morin on a Friday, wanting an image, t-shirts and hats by Monday
Paul Rand's $100,000 Answer to a Logo Contest
Kare keeps a running collection of advice from people she has met, and invites the audience to send her more good advice for it
Rand, who she says started working for magazines around age 15, was brusque about typography: with all the new fonts, you do not need that many — "You just have to know how to use them well"
At NeXT, where Jobs went after he had to leave Apple, she wanted to hire Rand for the logo. Jobs had not really heard of him and wanted a contest — "we could hire five people or firms and pay them each $15K," then keep working with the best
Rand's counter-offer: "You will pay me $100,000. I will do one logo, and you will like it." She says that is actually what happened: they liked it, and they paid him
She notes in passing that she would never think a contest "is the best way to get good creative," and calls working with Rand a great learning experience for everybody
Rand reused colors the way he reused fonts, and she still works from his books: "if PMS 354 Green is good enough for Paul Rand, it's good enough for me"
His logo rule was to do something to the name of the product, the way he put NeXT in the cube. He showed an old AT&T mark as what not to do — money can attach a random symbol that does not mean much to your name, but "most people don't have unlimited money"
Morningstar has a rising sun and IBM is "pinstriped and businesslike." Rand showed the UPS mark to his six-year-old daughter and asked what it was; she said, "It's a present, daddy," which he took as justification that it was understandable, though it was really a shield and a package
She is sorry UPS modernized it, imagining people around a table saying they are not just about packages anymore, and keeps hoping they bring it back
The Rest of the Advice, and the People It Came From
The futurist Paul Saffo supplied a line she takes metaphorically: "I always think I can do this in an hour when really nothing takes an hour." However well you think you know what you want to do, allow extra time
Her father directed the Monell Chemical Senses Center in Philadelphia, which studied taste and smell. She introduced him to Rand, who made the Monell logo, and the two got along well
Her dad's advice she calls realistic rather than cheerful. He had to raise a lot of money for the center, so he knew what he was talking about, and she tries to remember it because "I get depressed when I hear no"
Daniel Nordh, an architect born in Sweden, now living in Portugal, who worked in London for the mayor, described endless discussions around tables. His fix was "Make it visual," which she reads as show don't tell
Jean Pigozzi, whom she met through Steve Jobs, was an Apple fan who "maybe invented the selfie" and collects African art; his father was Italian and started the Simca Car Company "so that he could spend his life doing whatever he wanted"
Alan Kay, "who's in his 80s now," appears in a photograph with Hertzfeld, Bill Atkinson, Bud Tribble and Jobs. Bud Tribble quoting Kay gave her a tenet on interface: nest things rather than putting everything at the same level, so things can just appear and ease of use seems possible
Kay also told her directly that "Proportionally spaced fonts can actually look pretty good," which she took great joy in hearing
Steve Jobs, the Pirate Flag, and the Worst Advice She Ever Got
Jobs is in the advice collection too, photographed sitting in her cubicle at Apple, where in the '80s he told her to "Appreciate what you have right now."
At the first offsite he put up three goals, and the second one produced the flag: the programmer Steve Capps sewed a black flag, and Kare painted a skull and crossbones on it with a striped apple as the eye patch
They came in in the middle of the night and climbed on the roof "because obviously security was a lot more lax back then," flew it, and meant it as a rejoinder — they were the pirates
Demoing the Mac to lots of people left her with a caution she still applies: some people can work out how to use a thing and some cannot, and calling it easy is what makes the ones who struggle feel dumb
The worst advice she says she ever got from Jobs was about the stock: "If Apple stock was ever going to be worth anything, don't you think I'd be holding onto mine?" She decided not to buy hers, on the reasoning that he would know
He also tried to move her off the tools: "Susan, you can twiddle bits and never make more than $20,000. Or it's better to be a creative director." She took the creative director job at NeXT and got to work with Rand out of it — "But ultimately I was a bit twiddler at heart and I went back to it"
Jobs also took visiting executives to see a particular movie, which she liked for a reason of her own: it had a welder in it
Sleeping Bags, Fifteen People, and Never Showing Steve One Idea
Jay Chiat, who started the ad agency Apple used, Chiat\Day, is another source. "It was not work-life balance at the time. Everybody I worked with in the software group had a sleeping bag in their cube."
On company size, she says a couple of companies she worked for decided that at 15 people you could still do consensus hiring with everybody in a room and on the same page. Past that there is an upside and a downside
Hertzfeld's advice on managing Jobs: "Don't show him one thing because he'll say he doesn't like it." Being sent away to do better has its uses, but with a few options in front of him he can be involved, call something terrible and still pick something
Several pieces of the collection sit on slides she points at rather than reads out, including her mother's advice, a friend's father's, and a line from Pinterest co-founder Evan Sharp, whom she names alongside Ben Silbermann
Dennis Hwang, who started at Google as a Stanford undergrad and who she calls a terrific computer scientist and artist, passed on Google's prevailing wisdom, which she says she would preach herself: "don't mess around with the logo and put it in a different color and put it on a crazy background until people know it so well that you can play with it" — and then made the doodles, which did pretty well
One well-known figure's advice she reads against the grain: not as a reason to be discouraged and quit trying, but as a sign it may be time to go on to the next idea
She closes by thanking Y Combinator, saying the day ran smoothly, everyone was gracious, and she felt envious of the people taking part
Kare's bottom line is that none of it was ever really about a grid of pixels: an icon works when it carries one clear idea simply enough that a stranger can project themselves onto it, and finding that idea is a matter of drawing the options rather than knowing the answer.
Products, Companies & Tools Mentioned
Apple and the original Macintosh (The 128K machine she designed icons and system fonts for, built by a group told it was making a computer anyone could use)
Chicago, New York, Geneva and Ransom (The system fonts she drew; Chicago was nine pixels at cap height and later ran on the first iPod, and the city names were Jobs's edit to her Philadelphia suburbs)
MacPaint and the icon editor (Bill Atkinson's paint program was her favorite; Hertzfeld's editor let her toggle bits and generate an icon's hex code, with no shapes and no undo)
ImageWriter (The printer whose sprocket-fed paper she drew into the print icon, which is why she calls that icon a trap)
NeXT (Where Jobs went after Apple, where she was creative director, and where Paul Rand did the logo)
Microsoft Windows 3.0 (Her first color work, 16 colors dithered so they would not look like a garish chessboard)
Solitaire (She designed it and then removed it from her own computer to stop playing)
General Magic (Logo plus a literal desktop of hallways, doors and file cabinet drawers, and jars of text she calls the worst thing in it)
Facebook Gifts (A dollar-a-drawing gift shop that ran for not quite four years; cute beat expensive, and Facebook closed it rather than compete with third parties)
Pinterest (Animated icons kept subtle enough not to irritate; founders Evan Sharp and Ben Silbermann appear in her advice collection)
Swatch (The alarm clock icon options she uses to show how unscientific the process is)
Ledger (Badges for a new crypto wallet with a front attachment opening, briefed as retro-looking)
Magic Puzzle, Pikmin Bloom and Peridot (Logo work and logo studies; the puzzles perform a magic trick when finished)
The National, Amtrak's magazine (Commissions artists to interpret the route map; she did pixelated icons of train destinations)
UPS, IBM, Morningstar and AT&T (Rand logos she uses to teach: the UPS present, IBM's pinstripes, Morningstar's rising sun, and AT&T as the random symbol to avoid)
Monell Chemical Senses Center (Her father's institute in Philadelphia, studying taste and smell; Rand made its logo after she introduced them)
Google (Dennis Hwang's doodles, against the house rule not to play with a logo until people know it cold)
MoMA (Holds the graph-paper notebook of icons she took to her Apple interview)
Chiat\Day (The agency Apple used; its founder Jay Chiat is in her advice collection)
Books & Resources Mentioned
Scott McCloud's book about comics (The source of her icon theory — less detail makes an image more universal. She says it "has so many good insights about user interface too" and came out 10 years after the Mac)
Paul Rand's books (She still looks in them for the colors he recommended for NeXT, PMS 354 Green among them)
Get the latest market chatter and takes as they happen:
X | Threads | Instagram | YouTube | TikTok | Facebook