What Founders Can Do To Improve Their Design Game
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Raphael Shad is a unique figure in the startup world. He's both a designer and the successful founder of Cron, a next-gen calendar for professionals, which was acquired by Notion and has gone on to become Notion Calendar, which is used by millions of people all around the world.

Design is not just how it looks, but design is famously how it works. You see another dimension to the world when you start kind of understanding design. So today we'll be chatting with Rafael to learn more about his design process and find out how founders can level up their design game.

So one of the things that I care a lot about is encouraging more designers to become founders and encouraging more founders to care about design in the earliest days of starting their company. So who better to have on than Rafael? Thank you for joining us. Awesome. Excited to be here. You've made the jump from designer to founder.

Why do you think that there aren't more designers out there making that same leap? Well, first of all, I kind of think, you know, there should just be more talented people building companies in general, not just designers. But designers actually have something really valuable to bring to the table when it comes to starting companies. To build a product that people

you know, really want. I think you need kind of like three things to build a successful product in the company. You need to have something that, you know, desirable that people want. You need it to be viable. So kind of like you can build a business out of it and you need it to be feasible. You need to be uniquely positioned to actually build it, you and your team, right? And if you think about these three things, desirability, feasibility and viability, kind of three overlapping circles, and you can map them to more traditional disciplines, it's actually design

and business and technology. And design is really kind of like, you know, back to the YC ethos, make something people want. Design is essentially figuring that out. It's that mentality that I think a lot of designers think about. What do you think is holding designers back from starting more companies if they're so well suited because it's how they spend a lot of their days and hone their craft?

Yeah, it maybe kind of goes back almost historically, kind of the context. Maybe back in the day, design was much closer to an artistic pursuit, right? Where art is more about asking questions, whereas design these days is more actually about problem solving and answering questions, delivering solutions, basically.

And so that probably happened sometimes during the industrialization, is my guess, where design could have moved closer to be part of sort of like the problem solving, you know, engineering kind of apparatus. But back then in the industrialization, designers didn't necessarily control the means of production. Right. And so that is really changing now where designers can essentially through software, through code, can actually be really close to building the object. Right.

Versus kind of like, you know, back in the day, maybe it's furniture or other objects. And so I think that's what makes this moment in time so interesting for designers to build companies and build products. Yeah. And tell us a little bit about your journey going from designer to founder of your company to ultimately selling it to Notion. So I actually have a technical background where I have a CS degree from back in the day.

that really allowed me to build things. I never studied CS because I wanted to go extra deep on that aspect, but really I wanted it to be a tool for me to build my own designs. And so very much like maker at heart, always had dreamed up things, designed things, and then wanted to be able to build in the medium.

I spent my graduate studies at the MIT Media Lab where I built a lot of physical things. So again, kind of designing things and then building it in the medium that the ultimate object is in. That's really important to me. And of course, these days where so much is software and so many of the products that I've built throughout my career are basically software, being capable to prototype, feel, but also sometimes even build the real thing is sort of what got me

to this technical education. That's such a great point actually because that's kind of my journey too. I started learning design and learning how to code because I wanted to create the thing that I envisioned in my head

and to have the ability to execute and build it yourself is like... So powerful. Yeah, exactly. It's like the ultimate form of that. And so do you think designers should learn to code? You should be comfortable in the medium that you're building in. And if software is what you're building, made out of code, but also pixels, being relatively close to how the actual thing gets built gives you such a huge advantage.

Especially now, kind of like in the AI age where, you know, the thing that we design is less kind of like the nouns, kind of the buttons and the text fields and the sidebars, but really think more about kind of like the verbs. You know, autocomplete, autosuggest, summarize, send an agent to do something.

those are things that are kind of hard expressed just by drawing a rectangle within the rectangle within the rectangle but you really need to start to think about time as an aspect in your designs etc and static prototypes oftentimes kind of break down don't quite give you the feedback that you get with real data and so i think whatever gives you so like ability to play with the real thing

I think is what gives designers the edge. Yeah, that's actually a great point. I've never thought about it like that. It'd be like if you were a sculptor and you just created the plans for the sculpture and then handed it off to somebody else to do the thing, that would sound crazy, right? Yeah. So why would we think that kind of software design and software engineering are these entirely separate disciplines, right? Yes. What about for maybe technical people

engineers that don't have a good eye for design, you know, don't know how to create something that is user friendly and think through all those considerations. What would you recommend to them? You know, top three things, what to do for people to become more design minded. First of all, I would say just kind of do. Learning by doing, right?

When you look at designs, you oftentimes can tell this is a good design or this is not as good of a design. This design works, this design doesn't work as much, but you don't really know why. When you start doing, you will probably produce bad designs

at the beginning, but at least you kind of understand the material and you start to understand why a design works and doesn't work. What are the constraints that a designer that created a design that maybe doesn't work as well, what are the constraints that that designer had, right? You really start to kind of almost see the world through sort of like a, you know,

reading the world kind of through like Matrix. You see another dimension to the world when you start kind of understanding design. The second thing that I would say is to surround yourself with beauty. Surround yourself with like really nicely designed objects. It can be physical, but also can be the ergonomics of software, right? If you don't tolerate and let in sort of like

just that noise of like bad designed objects or not designed objects and all that cheap stuff. By the way, like, well, good design can also be cheap. Like that's an aspect of kind of like good design production. But surround yourself with well-designed objects to sort of like absorb and sort of like develop a taste.

And the third thing I would say is read some design books. There's so much deep knowledge in some of these classics. I would say top three would be Grid Systems, which is what taught me all about text and layout. Actually, a fun fact about Grid Systems is that the Kron Orange

FF4700, kind of that fiery orange, was inspired by the cover of that iconic orange book. Yeah, very cool. A second great book is The Elements of Typographic Design. It kind of taught me everything about type. Not just kind of choosing a font, but how to use type as a graphic and as an interface element.

And once you sort of like, you know, you kind of know about kerning and ligatures and microtypography, line spacing, et cetera, you see the world in a completely different way. It's kind of like a little bit of blessing and the curse, but extremely powerful. A third great book is Design of Everyday Things. It's a classic. It's the book with the cover that has a teapot

where the spout comes on at the wrong end, kind of showing you about usability. Main takeaway from that one actually is to convey the importance of conveying the mental model of the apparatus or software you build to the user through UI, through design.

But this is a tried and true classic in the design. And I have a whole thread on Twitter about some of the top design books that goes into more graphic design and traction design, etc. that I'm sure we can link down in the description below. And you said an interesting word there, taste. How do people do that? Is that something that can be learned? And if so, how should somebody go about getting better design taste?

You can't maybe learn taste, but you can certainly kind of like acquire it. And again, kind of to the earlier point, by surrounding yourself and not tolerating kind of bad design is not about kind of being snobby. It's more about

separating, like even thinking about the design dimension and separating something from being well-designed and not well-designed, something that works and something that doesn't. And so going through life with this lens and every interaction, every doorknob that you touch, kind of thinking of it, is this a pleasant experience? Is this a reliable design? Is this a lasting design? Is it a design that gets better with age?

And I don't just mean kind of like physical patina, but also in software, something that gets better over time by the interface getting adaptive, for example, making it more obvious how I use it, muscle memory, keyboard shortcuts, kind of peeling the onion off interfaces. I think that is where, if you study that, that is where you can become a great designer or if you're an engineer, kind of a design-minded engineer.

20, 25 years ago when you were kind of coming up, how did you develop that taste? Like, did you kind of have it early on or was it something that you just acquired over many years of surrounding yourself with great design? I think it was probably more the latter.

especially early on for me, it was not software. It was kind of more physical objects. But the importance of surrounding yourself with good things, that was certainly more a family thing. You know, don't buy like a lot of things. Buy a few things that really like last and have high quality. And then evaluating kind of the object, like, hmm, you know, like, why is this so pleasant to hold? Why is this, you know, work so well? How can you repair things?

things. So repairability is also kind of like a hallmark of good design. That's where I developed kind of the sensibility and interest in, Hey, like I want to shape, shape this myself. And once I realized like everything is designed, whether it's proactively designed or not, like everything is designed, even like an accidental design, right? Every pen, every table, everything is designed.

And even things that we don't think of like a designer so far, like everything has like someone that made it. Now you can kind of consciously made it better. And especially once you understand the simple fact that everything around us is designed, there's like, well, there's not, I think this is a famous Steve Jobs quote. Like there's people around me are not that much smarter than me, you know? So you mean like I can actually influence all of this? And that's when I was like, aha, like naturally I need to become a designer.

Yeah, that's actually a really interesting point, which is everything is designed. The question is whether it was intentional or not and whether thought went into it or not. Totally. And so, you know, if you're a founder, maybe that doesn't have experience with, you know, focusing or really caring about design because you just like to crank out the code and, you know.

build the thing, what would you tell them as ways to try to acquire more of that and things that they should focus on for why they should care about this and why it matters to have really great design and be thoughtful and intentional about it? There was a recent tweet by Gary, president here at Y Combinator, and he says kind of like good design, especially in early stage startups is a lost art.

And I was like, interesting. Why is that? Especially now that it feels like with AI, basically everything is getting reimagined. Design first, right? And so I was like, now is the moment where design can have a huge outside impact.

outsized impact, I feel. I think companies that recognize the value of design, especially right now, when everything is shifting, have a huge edge. Yeah. It seems like the focus has become so much on speed, rightly so, shipping product, building it. We don't have time to be thoughtful about the design. So whatever comes out is what comes out.

And those that do put in the time to be thoughtful and focus on the things that really matter, it's felt, I think, by the end users and appreciated in a different way. Totally. And I think kind of design, you know, is not just kind of how it looks, but design is famously, you know, how it works. I would even take this a step further. I would say design is just how it looks, how it works, but design is how it's built.

You can feel it end to end. What's their design involved when it was built and what technology was used? Were there loading states, latencies, all of that is in my mind kind of design. So the material that is used to create an object, a piece of software, a framework, whatever, to me that is part of the design. Yeah, absolutely. What are some tactical things that founders can do to level up their design game?

Thinking about hiring for design early on is a really important one. So first, kind of like designers, design founders, that's one aspect. But then also for more technical people or even designer founders to really kind of like amplify their design, hiring designers

talented designers relatively early on. I think that's a huge leverage. Tapping into networks such as Y Combinator or the Designer Fund here in San Francisco that have built out these networks, bringing designers more into tech companies early on. I think this is one way for founders to really level up the design of their companies. Cool. I'd love to hear more about your design process.

Yeah, so typically kind of for me starts sketching. I mean, you know, you oftentimes kind of first talk to users, right? You may have some intuition, but you really want to in the end solve user problems. So that's where it really starts, right? Intuition or kind of like user problems. But then when you kind of want to quickly visualize something, like very quickly move from insight to capture that insight, I still found it most efficiently to just quickly jot it down on a piece of paper.

And so that's what I still kind of like use my sketchbooks for. I'm still just sketching a ton of interface ideas and kind of whatever is easiest for you to quickly capture the idea. I think that's most important for me at sketching. And then moving pretty quickly from capturing that sort of like visual insight and give it some form to

starting to play with it as high fidelity as possible. For some people, this may kind of be maybe taking a photo of the sketch and putting it in Figma and starting to wireframing it out or directly kind of more pixel perfect designs. What I sometimes really like to do is also just kind of take the sketch, have it on the table, and then jump into a code editor and already kind of try to start to assemble the UI, just start to feel it. Because I kind of know what good looks like.

I don't necessarily need to draw it out, but I want to feel whether it also feels good and the way we're building it, whether that kind of works back to the sort of like design is just how it looks, but how it works and also how it's built. Yeah.

Talk more about that, because I've heard other designers talk about that, like trying to get a sense for how it feels. And when you're trying to get a sense for the feel of something that you have designed, what are the steps that you're actually going through there to tell if it feels right? You kind of start to develop an intuition, especially kind of just interaction design, like what works, what doesn't, what's consistent with platform norms. And this goes down to like, when should a field blur or focus, or when should I drop down a

appear when you focus the field, like how does it interact with text, with the keyboard? So respecting kind of like, you know, user expectations and standards that they, you know, are used to from years of computing, not reinventing the wheel, but then also pushing the boundaries, right? That's kind of where I think this dance, this elegant dance as a designer, as a builder kind of comes in to really start to build something that's

just feels right, feels fun, feels novel, but still kind of familiar. And so that's when you really need to build within the actual medium. Yeah, that dance is always tricky, right? Like designing a thing that people are familiar with while also wanting to kind of push the boundaries and innovate and

on something new and better. But that requires education and changing expectations around how software should work. And obviously, AI is blowing that up in so many ways. What is that dance? Is that just your own kind of technology?

of taste and determining where to draw the line on consistency with existing norms versus trying new things? How do you think about that? Initially, it's maybe kind of like a taste. Do I like something or kind of rather, does it work for me? I always kind of say like is not a design word. It either works or doesn't work. And so that initial assessment might kind of lie with the designer.

But then pretty quickly, because you built the thing or at least a prototype of it, you can actually distribute it over the web or over, you know, just kind of show someone on a laptop your prototype and let them interact with it. And ultimately, I think users are the ultimate judge whether a design works or doesn't work. You know, one of the reasons why I think sketching on paper is so powerful is because the medium of paper affords you to do anything.

Um, you don't have any constraints at that point yet. Once you start to get into like design tool or code, you start to kind of get like dragged down by, so like the constraints of the medium paper is this super flexible. It's like, it gives you just enough sort of like boundary, right? It kind of, the page focuses you within this sort of like, you know, within the page, you kind of get an idea out of your mind. It's not this infinite thing. So the constraint there is really good, but then within the page is completely unconstrained.

Like, I can draw anything. Yeah. You're not limited to lines and rectangles and text. 100%. Exactly. And so I think a paper is super approachable for non-designers. Everyone can doodle, right? So it's super approachable. It's very flexible. And you can really imagine anything on the page. And then you can take it, snap a picture or whatever, send it to an engineer,

or a designer to increase the fidelity of it. Or upload it to AI now. Exactly. And so for a while, it maybe seemed that sketching is-- clearly, we should just start digital first. But what if now the value of a sketch actually becomes very important again when you can skip that entire step? You jot down an idea. You quickly sketch it out. You take a picture of it. You upload it into a design tool that then

turns into the real deal, you can skip everything in between. And so it really then comes down to what user problem are you solving and is it an innovative approach to solving it. Awesome. Well, Raphael, thank you for joining us. It was super interesting to hear about your journey and your process here starting with sketching. I think it's really interesting to see how your mind works when you're starting on a project all the way through the completed thing, which is you can feel the quality in the products that you have designed.

it's no wonder that there are millions of people that are using them today. Yeah, and my main message kind of for the audience would just be, you know, to encourage more designers to become founders. It's been an amazing journey for me, partially also through Y Combinator. And then for existing founders to kind of like develop ideas

sort of like a design mind, because it's going to be one of the most important skill sets to rebuild like the huge next generation companies. Yeah. More examples of designers that can build the product to actually execute. So much power comes with that. And so I think you're a great example of that. So thank you for joining us today. Thank you so much.