Become a 10x startup designer 💡

Over the last 100 or so episodes, I've interviewed some of the first designers at companies like Linear, Facebook, Perplexity, Ramp, DoorDash, and a bunch of others. So this episode pulls out some of the key ideas to help you become a 10x startup designer. So let's begin by hearing from Helen Tran.

I'm going to start working on, like, understand the competitors in the market. I'm going to start understanding the entire product suite relevant to this vertical. And I'd start to, like, actually map this out with the founder, trying to help them understand their own industry and being like, is this where you actually want to go? Does this make sense to you? Does this make you feel confident? Do we need to do more research? Are you excited about this area of the market? Like, those are the types of questions that you can help answer with them.

When you're a founding designer, you're not just thinking about product, you're thinking about company positioning. So as you're evaluating a market, you're looking for opportunities where you can turn your blank slate into a competitive advantage. And that's something that Ian Wharton shared as well.

Designers, I think, come with this degree of ignorance, which is, you know what, I don't know that particular field, but I come with all the tools to find it out. So what you hope for is you know enough about the market that you're entering to add value and approach it with a particular perspective. But you're not so entrenched in that market that you're unable to see innovation. You're unable to see ways of doing things differently, and that's that sweet spot.

Diego took this idea to a whole other level and didn't even look at competitors while he was first designing Ramp.

Because I didn't know how it need it to work. I basically just decided to think about what would I want it to look like and what would I want it to feel like. And didn't do any competitive research to start. I just said, let me just clean slate. Really trying to simplify and make things one click as much as possible. And I think not knowing how things should be was a real advantage at the beginning.

Regardless of the type of founders that you're working with or the industry that you're entering, the number one skill that you can bring to the table as a designer is generating a lot of ideas.

If you're lucky enough to be employee one to five in a startup, you should be the ideas guy with the founder. Every founder I know would adore that type of person.

When you're Generating a lot of ideas, though you also have to be quick to throw them away when you're working at a startup.

What entrepreneurs ought to look for are designers who don't fall in love with their work because they're producing so much of it. They can't pick a favorite child because they have so many. There has to be a willingness in that pre product market fit era to just be throwing away ideas, to stand something up, spend a lot of time working on it, and then walk away from it because it's just a dead end. And that's a muscle you just need to exercise now. It's like making sandcastles. It's going to get washed away pretty fast. Even the really great ones, that's fine. That's just the nature of the work.

It reminds me of a conversation that I had when I was first starting out at Maven. One of the co founders, Shreyan, said the hardest part about the role will be knowing which good ideas to not do. And this is an idea that Diego also shared when talking about his time at Ramp.

Creating focus and choosing the right things to work on is the most important job that you can do at a startup.

Founding designers have to be able to see the bigger picture because things change so quickly in the early days that you might not even be working on the right thing.

So much of arriving at an insight is having that mental flexibility to recognize, oh, I came into this, you know, selling Happy Meals, but when I started listening really closely, people just really wanted the toy. And turns out toys are a much bigger business than burgers. And I had to kind of like be able to like walk away from the kitchen and become a toy maker, even though that's not what I set out to do. I think that there's a certain degree of mental openness to not just like focusing on the solution that you're bringing to the forefront, but to the broader problem space that's sort of sitting right on the periphery.

As a founding designer, you can't wait for people to tell you what to do or point you in the right direction.

You should be coming up with prototypes on their behalf. You should be going to talk to customers and bringing it up to them. That's how you win influence and that's how you actually work with an early stage company and make them feel like you're there with them as opposed to kind of like downstream and waiting for instruction. No founder wants that.

This proactiveness applies outside of the product too. I mean, one of the reasons I love the founding designer role so much is that there are truly countless opportunities to make an impact. Here's Diego Zaks and Henry Motissette talking about their experience.

At the beginning I was doing all of the branding, all of the marketing, all of the advertising, just everything and the product as well.

The sort of beautiful chapter that you get to have of being a founding designer is the kind of whatever it.

Takes mentality that whatever it takes mentality is why you grow so quickly in a startup environment. Take Marco Cornaccia for example. He's the one who designed the diagram website that totally broke Twitter. But he wouldn't even have learned that skill if he wasn't forced to.

I think it's a super valuable experience to be able to be that founding designer just because you have no choice but to kind of experiment and try all those different things. My first startup job and we wanted to have this video hero and I didn't know how to make videos and I discovered this whole other path of like, oh, maybe I could just build the application inside of Webflow and like have that be the actual thing that you interact with. I would have never probably even thought of doing that if I wasn't forced, which is like a ton of startup work is just like we need this thing and like somebody needs to figure it out like who's down to go and like go down that path.

It's a big reason why early stage companies look to hire self starters. Here's David Wong to share more.

One of the traits I actually look for a lot when I run teams at an early stage startup is if I've seen they've started their own business before or if they started a side project. I'm really keen to learn more about what they experienced through that time.

Real quick message and then we can jump back into it. So I've been using this new product to do research called Genway. It uses AI powered interviewers to help you gather qualitative data at basically an infinite scale. So I've actually been interviewing listeners of this show all over the world. I tell the AI what I'm hoping hoping to learn and then it has a dynamic conversation with each person. Genway then organizes all of the key insights for me automatically. So I learned more in a two week study than I had in a year and a half prior. Needless to say, I am totally hooked. And if you want to take your research to the next level, head to dive club Genway to get two months free. That's G E N W A Y. I've been anticipating Today for quite some time because Ray Cat Notes are finally here. Their old Floating Notes product was my go to for quick captures, but they've truly taken it to the next level. There's markdown for formatting, keyboard shortcuts, multiple notes. You can even create a quick link to a specific note and assign a hotkey to it so that way you can quickly open it up from anywhere in a single keystroke. It's just another way that Raycast helps me stay in flow while I work. So if you're not using it already, seriously, I can recommend this product enough Head to Dive Club Raycast to get started. That's R A Y C A S T okay, now onto the episode and the best way to get a job as a founding designer is to demonstrate expertise in that specific industry. It's a trend that's been pretty clear across all of my interviews. Like listen to Nate Parrot describe what he was doing before he got hired as the founding designer at the browser company. Ever since college I saw people make fancy email apps and fancy notes apps and I was always like why is nobody making a fancy browser? Like this is a tool that I use way more than any of those other tools. Like why is nobody making the mailbox of web browsers? And so in my spare time I was actually like prototyping a web browser on my own. Adrian Griveau shared a similar story before joining as the founding designer of linear.

So I got really in love with GitHub, but also as a designer I had a lot of functionalities that I didn't like that were mostly for engineers. So with some friends we built a Mac app called Git Scope and so I really started to get very interested into like product management issues, ticketing.

At the time I was already prototyping cohort based course platforms in my spare time before I applied to Maven, so it wasn't that hard to communicate how passionate I was about the space. But another angle you can use to sell yourself is being a great candidate for a founding designer role is leaning into your generalist skill set, thinking about.

What makes a good founding designer or what gave me the advantage to be able to execute. It's really being a jack of all trades of having actually done graphic design and books and advertising and branding. Like a pretty like winding career so that when, hey, this week we actually need to do ads. I've done that before. I can write copy, I can do Photoshop.

Many of my favorite episodes are when we get to hear from some of the earliest designers at these really high profile startups. So if you want to learn more about this startup Designer Journey, Head to Dive Club episodes and you'll be able to hear some of the earliest design stories behind startups like Linear Perplexity Ramp. And who knows, maybe it will inspire you to start your own founding designer journey. Hey, it's Rid. Don't forget if you want to go even deeper. Each week I send an email out to over 10,000 designers with bonus resources and key takeaways from these conversations. So Head to Dive Club email to sign up. Okay, I'll see you next week.