Y Combinator Startup Podcast - What Founders Can Do To Improve Their Design Game

Episode Date: March 28, 2025

In this special episode of Design Review, Aaron sits down with Raphael Schaad, the Head of Calendar at Notion to discuss his leap from designer to founder, why illustration is an important first step when building a new product, and what ultimately makes designers uniquely qualified to start a company today.

Rafael Shad is a unique figure in the startup world. He's both a designer and the successful founder of Kran, 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 Raphael 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 Raphael. 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 sense? 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, 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 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 has 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 kind of to an artistic pursuit, right? Where art is more about kind of like asking questions, whereas design these days is more actually about kind of problem solving and answering questions. They're learning 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, 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 his furniture or like other objects. And so I think that's what makes. 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, you know, have in love a kind of like CS degree from back in the day that really allowed me to build things. I never kind of studied CS because I wanted to, you know, 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 sort of like maker at heart, always had kind of like, you know, dreamed up things, designed things, and then wanted to be able to build in the medium. So 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 sort of like object is

in. That's really important to me. And of course, you know, these days where so much is software and so many of the products that I've built throughout my career are basically software, being, you know, capable to prototype, feel, but also sometimes even like built the real thing is sort of like what got me to this technical, you know, education. That's such a great point, actually, because that's kind of my journey too, is, you know, 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, you know, 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 are you building, made out of code, but also, you know, pixels, being relatively close to, like, 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, auto-suggest, 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 will 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 start to, when you look at designs, you oftentimes kind of 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 can 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 designer had, right? You really start to kind of almost see the world through sort of like, you know, reading the 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 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 Cron Orange, FF470 and then a 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 current, and ligatures and microtipography, line spacing, etc. 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 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 we, I'm sure, 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, like, how should somebody go about getting better design taste?

You can't maybe learn taste. 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, you know, touch kind of thinking of it, is this a pleasant experience? Is this a reliable design? Is this a lasting design? Is this a

lasting design? Is it a design that gets better with age? And I don't just mean kind of like, you know, physical patina, but also in software, something that gets better over time by you know the interface getting adaptive, for example, making it more obvious how I use it. Muscle memory, keyboard shortcuts, kind of peeling the onion of sort of like, you know, interfaces. I think that's that 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. Like 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 of good things, that was sort of like more a family thing. You know, don't buy like a lot of things. by 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? 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 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.

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 this simple fact that everything around us is designed, then it'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 design. The question is whether it was intentional or not.

Totally. 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. unintentional about it.

There was a recent tweet by Gary, president here at Y Combinator, and he says, kind of like, good design, especially in the early stage startups, is a lost art. And I was like, interesting. Why is that? Yeah, why I think that's? 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 the, have like a huge

outside's 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, you know, 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 it in a different way. Totally. And I think kind of design is not just kind of how it looks,

but design is famously 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. Kind of like how, you know, was their design involved when it was built and what technology was used,

where they're 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, the framework, whatever, like 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, you know, that's one aspect. But then also for more technical people, or even,

Even designer founders to really kind of like amplify their design, hiring 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 and 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 are 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

chot it down on a piece of paper. And so that's what I still kind of like use my sketchbooks for. still is just sketching a ton of interface ideas and kind of whatever is easiest for you to to quickly capture the idea and that's most important for me at sketching and uh and then moving pretty quickly from capturing that sort of like visual insight and give it some form to starting to play with it um as high fidelity as possible for some people this may kind of be you know uh maybe taking a photo of the sketch and putting it in the figma and starting to kind of like you know 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 like a code editor and already kind of try to start to assemble sort of like the UI, just start to feel it. Because I kind of like 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, you know, that kind of works. Back to the sort of like design is just how it looks, but how it works and also, you know, 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, you know, blur or focus or when should a drop-down 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 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 on something new and better.

But that requires education and, you know, changing expectations around how software should work. And obviously, AI is blowing that up in so many ways. What is that dance? Like, is that just your own kind of taste and determining, you know, where to draw the line on consistency with existing norms versus trying new things? Or 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 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 like 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. 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.

So 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, it's completely unconstrained. Like, I can draw anything, right? You're not limited to lines and rectangles and text. 100%, exactly. And so I think, you know, 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 the picture or whatever, send it into an engineer or a designer to can, like, increase the fidelity of it. And so... Or upload it to AI now. Exactly. And so, you know, for a while it maybe kind of seemed that sketching is like, clearly we should

just start this digital first, right? But what if now, you know, kind of like the value of a sketch actually becomes very important again when you can skip that entire step, you kind of shot down an idea, you quickly sketch it out, you take a picture of it, you upload it into design tool that then turns into the real deal, you can skip everything in between, right? And so it really then comes down to what do user problem are you solved? and is it sort of like 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. And 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, which is be, you know, to encourage more designers to become founders. It's been an amazing journey for me, partly also through Y Combinator.

And then for existing founders to kind of like develop sort of like this design mind because it's going to be one of the most important skill sets to build 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.

Thank you.