0:00

Raphael Shad is a unique figure

0:02

in the startup world. He's both

0:04

a designer and the successful founder

0:06

of Kran, a next-gen calendar for

0:08

professionals, which was acquired by Notion

0:10

and has gone on to become

0:12

Notion Calendar, which is used by

0:14

millions of people all around the

0:16

world. Design is not just how

0:18

it looks, but design is famously

0:20

how it works. You see another

0:22

dimension to the world when you

0:24

start kind of understanding design. So

0:26

today, we'll be chatting with Raphael

0:28

to learn more about his... design

0:30

process and find out how

0:32

founders can level up their

0:34

design game. So one of the

0:37

things that I care a lot

0:39

about is encouraging more

0:41

designers to become founders

0:43

and encouraging more founders

0:45

to care about design

0:48

in the earliest days

0:50

of starting their company.

0:52

So who better to

0:54

have on than Raphael?

0:56

Thank you for joining

0:58

us. the jump from

1:00

designer to founder. Why

1:02

do you think that there aren't more

1:04

designers out there making that same leap?

1:06

Well, first of all, I kind of

1:09

think, you know, there should just be

1:11

more talented people building companies in general,

1:13

not just designers. But designers actually have

1:15

something really valuable to bring to the

1:17

table when it comes to starting companies.

1:20

To build a product that people, you

1:22

know, really, really want. I think you

1:24

need kind of like three things to

1:26

build a successful product in the company.

1:28

You need to have something that, you

1:31

know, desirable, you can build a business

1:33

out of it and you need it

1:35

to be feasible. You need to be

1:37

uniquely positioned to actually build it, you

1:40

and your team, right? And if you

1:42

think about these three things, desirability, feasibility,

1:44

and viability can ask three overlapping circles,

1:46

and you can map them to more

1:49

traditional disciplines. It's actually design and

1:51

business and technology. And design is really

1:53

kind of like, you know, back to

1:55

the YCE thoughts, make something people want.

1:58

Design is essentially figuring that out. It's

2:00

that mentality that I think a lot

2:02

of designers think about. What do you

2:04

think is holding designers back from starting

2:07

more companies if they're so well suited

2:09

because it's how they spend a lot

2:11

of their days and hone their craft?

2:13

Yeah, it maybe kind of goes back

2:16

almost historically, kind of the context. Maybe

2:18

back in the day, design was much

2:20

closer kind of to an artistic pursuit,

2:22

right, where art is more about kind

2:25

of like asking questions, whereas design these

2:27

days is more actually about kind of

2:29

problem solving and answering questions, they're learning

2:31

solutions basically. And so that probably happened

2:34

sometimes during the industrialization is my guess,

2:36

where design could have moved closer to

2:38

be part of sort of like the

2:40

problem solving. you know, engineering kind of

2:43

apparatus. But back then in the industrialization,

2:45

designers didn't necessarily control the means of

2:47

production, right? And so that is really

2:49

changing now, where designers can essentially, through

2:52

software, through code, can actually be really

2:54

close to building the object, right? Versus

2:56

kind of like, you know, back in

2:58

the day, maybe it's furniture or like,

3:01

like, like, other objects. And so I

3:03

think that's what makes this moment in

3:05

time so interesting for designers to build

3:07

companies and build products. Yeah. And tell

3:10

us a little bit about. your journey

3:12

going from designer to founder of your

3:14

company to ultimately selling it to notion?

3:16

So I actually have a technical background

3:19

where I have haven't loved a kind

3:21

of like CS degree from back in

3:23

the day that really allowed me to

3:26

to to build things. I never kind

3:28

of studied CS because I wanted to

3:30

go extra deep on on that aspect

3:32

but really I wanted it to be

3:35

a tool for me to build my

3:37

own designs and so very much like

3:39

maker at heart. always had kind of

3:41

like, you know, dreamed up things, designed

3:44

things, and then wanted to be able

3:46

to build in the medium. So I

3:48

spent my graduate studies at the MIT

3:50

Media Lab where I built a lot

3:53

of physical things. So again, kind of

3:55

designing things and then building it in

3:57

the medium that the ultimate sort of

3:59

like object is in. That's really important.

4:02

And of course, you know, these days

4:04

where so much is software and so

4:06

many of the products that have built

4:08

throughout my career are basically software being,

4:11

you know, capable to prototype, feel, but

4:13

also sometimes even like built, the real

4:15

thing, is sort of like what got

4:17

me to this technical, you know, education.

4:20

That's such a great point, actually, because

4:22

that's kind of my journey, too, is,

4:24

you know, I started learning design and

4:26

learning how to code because I wanted

4:29

to create the faith. that I envisioned

4:31

in my head and to have the

4:33

ability to execute and build it yourself

4:35

is like powerful. Yeah, exactly. It's like

4:38

the ultimate, you know, form of that.

4:40

And so do you think designers should

4:42

learn to code? you should be comfortable

4:44

in the medium that you're building in.

4:47

And if software is what you're building,

4:49

made out of code, but also, you

4:51

know, pixels, being relatively close to like

4:54

how the actual thing gets built gives

4:56

you such a huge advantage. Especially now,

4:58

kind of like in the AI age

5:00

where, you know, the thing that we

5:03

design is less kind of like the

5:05

nouns, kind of the buttons and the

5:07

text fields and the sidebars, but really

5:09

think more about kind of like the

5:12

verbs. auto complete, auto suggests, summarize, send

5:14

an agent to do something. Those are

5:16

things that are kind of hard expressed

5:18

just by drawing a rectangle within the

5:21

rectangle within the rectangle, within the rectangle,

5:23

but you really need to start to

5:25

think about time as an aspect in

5:27

your designs, etc. And static prototypes oftentimes

5:30

kind of break down, don't quite give

5:32

you the feedback that you get with

5:34

real data. And so I think whatever

5:36

gives you, so like ability to play

5:39

with the real thing. I think is

5:41

what gives designers the edge. Yeah, that's

5:43

actually a great point. I've never thought

5:45

about it like that. It'd be like

5:48

if you were a sculptor and you've

5:50

just created the plans for the sculpture

5:52

and then handed it off to somebody

5:54

else to do the thing, that would

5:57

sound crazy, right? Yeah. So why would

5:59

we think that kind of software design

6:01

and software engineering are these entirely separate

6:03

disciplines, right? Yes. What about for maybe

6:06

technical people? engineers that don't have a

6:08

good eye for design, you know, don't

6:10

know how to create something that is

6:13

user-friendly and think through all those considerations,

6:15

what would you recommend to them? you

6:17

know top three things what to do

6:19

for people to become more design-minded first

6:22

of all I would say just kind

6:24

of do learning by doing right when

6:26

you start to when you look at

6:28

designs you oftentimes kind of can tell

6:31

this is a good design or this

6:33

is not as good of a design

6:35

this design works this design doesn't work

6:37

as much but you don't really know

6:40

why when you start doing you will

6:42

probably produce bad designs at the beginning

6:44

but at least you kind of understand

6:46

the material and you start to understand

6:49

why a design works and doesn't work.

6:51

What are the constraints that a designer

6:53

that created a design that maybe doesn't

6:55

work as well? What are the constraints

6:58

that that designer had? Right? You really

7:00

start to kind of almost see the

7:02

world through sort of like a, you

7:04

know. reading the world kind of through

7:07

like matrix. You see another dimension to

7:09

the world when you start kind of

7:11

understanding design. The second thing that I

7:13

would say is to surround yourself with

7:16

beauty. Surround yourself of like really nicely

7:18

designed objects. It can be physical, but

7:20

also can be the ergonomics of software,

7:22

right? If you don't tolerate and let

7:25

in, so like just that noise of

7:27

like bad designed objects or not designed

7:29

objects and all that cheap stuff. By

7:32

the way, like... Well, good design can

7:34

also be cheap. Like that's an aspect

7:36

of kind of like good design production.

7:38

But surround yourself with well-designed objects to

7:41

sort of like absorb and sort of

7:43

like develop a taste. And the third

7:45

thing I would say is read some

7:47

design books. There's so much deep knowledge

7:50

in some of these classics. I would

7:52

say top three would be grid systems,

7:54

which is what taught me all about

7:56

text and layout. Actually a fun fact

7:59

about. grid systems is that the cron

8:01

orange F-F-4-7-0, but then a fiery orange,

8:03

was inspired by the cover of that

8:05

iconic orange book. A second grade book

8:08

is the elements of typographic design. It

8:10

kind of taught me everything about type.

8:12

Not just kind of choosing a font,

8:14

but how to use type as a

8:17

graphic and as an interface element. And

8:19

once you sort of like, you know,

8:21

you kind of know about curling and

8:23

ligatures and microtypeography, line spacing, etc. You

8:26

see the world in a completely different

8:28

different way. a little bit of a

8:30

blessing and a curse, but extremely powerful.

8:32

A third grade book is the design

8:35

of everyday things. It's a classic, it's

8:37

the book with the cover that has

8:39

a teapot where the spout comes on

8:41

at the wrong end, kind of showing

8:44

you about usability. The main takeaway from

8:46

that one, actually, is to convey the

8:48

importance of conveying the mental model of

8:51

the apparatus or software that you built

8:53

to the user through UI, through design.

8:55

But this is a tried and true

8:57

classic. design and I have a whole

9:00

thread on Twitter about some of the

9:02

top design books that goes into more

9:04

you know graphic design and traction design

9:06

etc that we I'm sure can link

9:09

down in the description below and you

9:11

said an interesting word of their taste.

9:13

How do people do that? Is that

9:15

something that can be learned? And if

9:18

so, like how should somebody go about

9:20

getting better design taste? You can't maybe

9:22

learn taste, but you can certainly kind

9:24

of like acquire it. And again, kind

9:27

of to the earlier point, by surrounding

9:29

yourself and not tolerating kind of bad

9:31

design, is not about kind of being

9:33

snobby. It's more about separating, like even

9:36

thinking about the design dimension, and separating

9:38

something from being... well-designed and not well-designed

9:40

something that works and something that doesn't

9:42

and so going through life with this

9:45

lens and every interaction every doorknob that

9:47

you you know touch kind of thinking

9:49

of it is this a pleasant experience

9:51

is this a reliable design is this

9:54

a lasting design is it a design

9:56

that gets better with age and I

9:58

don't just mean like you know physical

10:00

patina but also in software something that

10:03

gets better over time by you you

10:05

know the the interface getting adaptive for

10:07

example making it more obvious how I

10:09

use it muscle memory keyboard shortcuts kind

10:12

of peeling the onion of sort of

10:14

like you know interfaces I think that

10:16

that is where if you study that

10:19

is where you can become a great

10:21

designer or if you're an engineer kind

10:23

of a design-minded engineer 20, 25 years ago

10:25

when you were kind of coming up, how

10:27

did you develop that taste? Did you kind

10:30

of have it early on or was it

10:32

something that you just acquired over many years

10:34

of surrounding yourself with great design? I think

10:36

it was probably more the latter. Especially early

10:38

on for me it was not software, it

10:40

was kind of more physical objects. But the

10:43

importance of surrounding yourself of good things, that

10:45

was certainly more a family thing. You know,

10:47

don't buy like a lot of things, buy

10:49

a few things that really like last and

10:51

have high quality, and have high quality. And

10:54

then evaluating kind of the object, like, hmm,

10:56

you know, like, why is it so pleasant

10:58

to hold? Why is this, you know, work

11:00

so well? How can you repair things? So

11:02

repairability is also kind of like a hallmark

11:05

of good design. That's where I developed kind

11:07

of desensibility and interest in, hey, like,

11:09

I want to shape this myself. And

11:11

once I realized, like, everything is designed,

11:13

whether it's... proactively designed or not like

11:15

everything is designed even like an accidental

11:17

design right every pen every table everything

11:19

is designed and even things that we

11:21

don't think of like a designer so

11:24

far like everything has like someone that

11:26

made it now you can kind of

11:28

consciously made it better and especially once

11:30

you understand the simple fact that everything

11:32

around us is designed there's like well

11:34

there's not I think this is a

11:36

famous Steve Jobs quote like there's people

11:38

around me are not that much smarter than

11:40

me you know so you mean like I

11:43

can actually influence all of this and that's

11:45

when I was like aha like naturally I

11:47

need to become a designer. Yeah that's actually

11:49

a really interesting point which is everything is

11:52

designed the question is whether it was intentional

11:54

or not totally whether thought went into it

11:56

or not totally and so you know if

11:58

you're a founder maybe that doesn't have experience

12:00

with focusing or really caring about design

12:03

because you just like to crank out

12:05

the code and build the thing. What

12:07

would you tell them as ways to

12:09

try to acquire more of that and

12:11

things that they should focus on for

12:14

why they should care about this and

12:16

why it matters to have really great

12:18

design and be thoughtful and intentional about

12:20

it? There was a reason. tweet by

12:22

Gary, president here at Y-combinator, and he

12:25

says, kind of like, good design, especially

12:27

in the early stage startups, is a

12:29

lost art. And I was like, interesting,

12:31

why is that? Especially now that it

12:33

feels like with AI, basically everything is

12:36

getting reimagined. design first, right? And so

12:38

I was like, now is the moment

12:40

where design can have the, have like

12:42

a huge outside, outsized impact, I feel.

12:44

I think companies that recognize the value

12:47

of design, especially right now, when everything

12:49

is shifting, have a huge edge. Yeah,

12:51

it seems like the focus has become

12:53

so much on speed, rightly so, shipping

12:55

product, building it. We don't have time

12:58

to be thoughtful about the design, so

13:00

whatever, you know, comes out is what

13:02

comes out. and those that do put

13:04

in the time to be thoughtful and

13:06

focus on the things that really matter,

13:09

it's felt, I think, by the end

13:11

users and appreciated in a different way.

13:13

Totally, and I think kind of design,

13:15

you know, is not just kind of

13:17

how it looks, but design is famously,

13:20

you know, how it works. I would

13:22

even take this step further, I would

13:24

say, design is now how it looks,

13:26

how it works, but design is how

13:28

it's built. You can feel it end

13:31

to end. What's their design involved when

13:33

it was built and what technology was

13:35

used? Were there loading sites, latencies, all

13:37

of that, is in my mind kind

13:39

of design. So the material that is

13:42

used to create an object, a piece

13:44

of software, the framework, whatever. To me,

13:46

that is part of the design. Yeah,

13:48

absolutely. What are some tactical things that

13:50

founders can do to level up their

13:53

design game? hiring for design early on

13:55

is a really important one. So first,

13:57

kind of like designers, design founders, you

13:59

know, that's one aspect. But then also

14:01

to, for more technical people or even

14:04

designer founders, to really kind of like

14:06

amplify their design, hiring talented designers relatively

14:08

early on. I think that's a huge

14:10

leverage. Tapping into, you know, networks such

14:13

as, you know, Y Combinator or the

14:15

designer fund here in Zamartis. that have

14:17

built out these networks, bringing designers more

14:19

into tech companies early on. I think

14:21

this is one way to for founders

14:24

to really level up the design of

14:26

their companies. Cool, I'd love to hear

14:28

more about your design process. Yeah, so

14:30

typically kind of for me starts sketching.

14:32

I mean, you know, you oftentimes kind

14:35

of first talk to users, right? You

14:37

may have some intuition, but you really

14:39

want to in the end solve user

14:41

problems. So that's where it really starts,

14:43

right? Intuition or kind of like user

14:46

problems. But then when you kind of

14:48

want to quickly visualize something, like very

14:50

quickly move from insight to capture that

14:52

insight, I still found it. most efficiently

14:54

to just quickly shot it down on

14:57

a piece of paper. And so that's

14:59

what I still kind of like use

15:01

my sketchbooks for. Still is just sketching

15:03

a ton of interface ideas and kind

15:05

of whatever is easiest for you to

15:08

quickly capture the idea. I think that's

15:10

most important for me at sketching. And

15:12

then moving pretty quickly from capturing that

15:14

sort of like visual insight and giving

15:16

it some form to starting to play

15:19

with it as high fidelity as possible.

15:21

For some people this may kind of

15:23

be, you know, maybe taking a photo

15:25

of the sketch and putting it in

15:27

the figma and starting to kind of

15:30

like, you know, wire framing it out

15:32

or directly kind of more pixel perfect

15:34

designs. What I sometimes really like to

15:36

do is also just kind of take

15:38

the sketch, have it on the table,

15:41

and then jump into like a code

15:43

editor and already kind of try to

15:45

start to assemble sort of like the

15:47

UI to start to feel it. But

15:49

I want to feel, whether it also

15:52

feels good, and the way we're both...

15:54

it, whether that kind of works back

15:56

to the sort of like design interests,

15:58

how it looks, but how it works,

16:00

and also, you know, how it's built.

16:03

Yeah. Talk more about that, because I've

16:05

heard other designers talk about that, like

16:07

trying to get a sense for how

16:09

it feels. And when you're trying to

16:11

get a sense for the feel of

16:14

something that you have designed, what are

16:16

the steps that you're actually going through

16:18

there to tell if it feels right?

16:20

You kind of start to develop an

16:22

intuition, especially kind of just interaction design,

16:25

like what works, what does, and what's

16:27

consistent with platform norms. And this goes

16:29

down to like, when should a, when

16:31

should a, when you focus the field,

16:33

like how does it interact with text,

16:36

with the keyboard, so respecting kind of

16:38

like, you know, user expectations and standards

16:40

that they, you know, are used to

16:42

from years of computing, not reinventing the

16:44

wheel, but then also pushing the boundaries,

16:47

right? That's kind of where I think

16:49

this dance, this elegant dance, as a

16:51

designer, as a builder, kind of comes

16:53

in to really start to. build something

16:55

that just feels right, feels fun, feels

16:58

novel, but still kind of familiar. And

17:00

so that's when you really need to

17:02

build within the actual medium. Yeah, that

17:04

dance is always tricky, right? Like designing

17:06

a thing that people are familiar with

17:09

while also wanting to kind of push

17:11

the boundaries and innovate on something new

17:13

and better. But that requires education and

17:15

changing expectations around how software should work.

17:17

And obviously AI is blowing that up

17:20

in so many ways. What is that

17:22

dance? Like, is that just your own

17:24

kind of? taste and determining you know

17:26

where to draw the line on consistency

17:28

with existing norms versus trying new things?

17:31

Or how do you think about that?

17:33

Initially it's maybe kind of like a

17:35

taste where I like something or kind

17:37

of rather does it work for me?

17:39

I was going to say like like

17:42

is not a design word. It either

17:44

works or doesn't work. And so that

17:46

initial assessment might kind of lie with

17:48

the designer. But then pretty quickly because

17:50

you built the thing or at least

17:53

a prototype of it. on a laptop,

17:55

your prototype, and let them interact with

17:57

it. And ultimately, I think users are

17:59

the ultimate judge whether a design works

18:01

or doesn't work. You know, one of

18:04

the reasons why I think sketching on

18:06

paper is so powerful is because the

18:08

medium of paper affords you to do

18:10

anything. You don't have any constraints at

18:12

that point yet. Once you start to

18:15

get into like design tool or code,

18:17

you start to kind of get like

18:19

dragged down by, so like the constraints

18:21

of the medium. Paper is this super

18:23

flexible. you just enough sort of like

18:26

boundary right it kind of the page

18:28

focuses you within this sort of like

18:30

you know within the page you kind

18:32

of get an idea out of your

18:34

mind it's not this infinite thing so

18:37

the constraint there is really good but

18:39

then within the page it's completely unconstrained

18:41

like I can draw anything. You're not

18:43

limited to lines and rectangles and... 100%

18:45

exactly. And so I think, you know,

18:48

a paper is super approachable for non-designers.

18:50

Everyone can like doodle, right? It's a

18:52

super approachable, it's very flexible, it's very

18:54

flexible, and you can really imagine anything

18:56

on the page. And then you can

18:59

take it, snap the picture or whatever,

19:01

send it to an engineer, or a

19:03

designer, can like increase the fidelity of

19:05

it. sketching is like clearly we should

19:07

just start this digital first right but

19:10

what if now you know kind of

19:12

like the value of a sketch actually

19:14

becomes very important again when you can

19:16

skip that entire step you kind of

19:18

jot down an idea you quickly sketch

19:21

it out you take a picture of

19:23

it you upload it into the design

19:25

tool that then turns into the real

19:27

deal you can skip everything in between

19:29

right yeah and so it really then

19:32

comes down to what use a problem

19:34

are you solving and is it sort

19:36

like an innovative approach to solving it.

19:38

Raphael, thank you for joining us. It

19:40

was super interesting to hear about your

19:43

journey and your process here starting with

19:45

sketching. I think it's really interesting to

19:47

see how your mind works when you're

19:49

starting on a project all the way

19:51

through the completed thing, which is you

19:54

can feel the quality in the products

19:56

that you have designed and it's no

19:58

one. that there are millions of people

20:00

that are using them today. Yeah, and

20:03

my main message kind of for the

20:05

audience, which is be, you know, to

20:07

encourage more designers to become founders. It's

20:09

been an amazing journey for me, partially

20:11

also through Y-combinator, and then for existing

20:14

founders to kind of like develop sort

20:16

of like this design mind, because it's

20:18

going to be one of the most

20:20

important skill sets to build like the

20:22

huge next generation companies. Yeah, more examples

20:25

of designers that can build the product

20:27

to actually execute so much power comes

20:29

with that, and so I think you're a

20:31

great. example of that. So thank you for

20:33

joining us today. Thank you so much.