Founder Fridays: The Side Project that Became a Startup People Needed with Steve Ruiz of tldraw

For founders, like, especially early on where you are looking for product-market fit or you are looking for your, you know, what should this thing be? I mean, I didn't, I didn't like end up, I'd like, I didn't start with TealDraw. I didn't start with like a really good idea. I kind of arrived there via lots and lots of other things, some of which were like, didn't go anywhere, you know? So it was just like a lot of noise on the line before I found kind of came into something that connected with a lot of people.

Welcome to Founder Fridays, where we sit down with builders who've been in the trenches to talk shop, product, design, and the real lessons no one puts on a slide deck. I'm Ralia and I head our startups program in Europe. Today we're diving into a tool tool that is quietly redefining what it means to be building on the web. Tildraw isn't just another whiteboard, it's actually an infrastructure for creativity. And in just a few years, Tildraw has managed to attract hundreds of thousands of users and raised $14 million to keep pushing the boundaries of what it means to be building on the web. Behind it all, Steve Ruiz, artist turned developer turned founder, Thank you for being with us today.

Thank you. Thanks for having me.

Yeah, I'm excited to, to be deep diving into Tildraw. So let's start there. For listeners who are not developers like me, could you please make it a bit more real for us? What is Tildraw and what can developers do with it?

Okay, so there are certain products like maybe like your food delivery app, right? Where have you ever used like a DoorDash or something like that or a Deliveroo? I don't know if they have it in France.

I'm more of a Deliveroo person.

Deliveroo person? Yeah. At some point they show a little guy on a bike who's kind of like coming, going to your house or your flat or your office, right? Yeah. And that's like on a map, right? Well, maps are really hard. And so Deliveroo didn't build the map themselves. Maps are like an incredibly big, complex problem, but you can buy essentially a map. You know, there's tools like Mapbox or Google Maps where you're a developer, you're a product team, you want to have this feature, but there's a part of it that is like really tough. And even if you get it right, no one's going to really notice because that's just the way the maps should work. My bet with, with TealDraw was that as Miro and other apps were getting really a lot more popular, Mural, eventually FigJam as well, that this was also going to be kind of like a commodity feature inside of productivity apps or other types of things where people would want to build products on top of like an infinite canvas, something that kind of feels like a whiteboard or feels like a design tool kind of canvas. And I'd built a couple of them myself, and I worked in design tools, and I'd seen how they were built and other things. And so I began working on one that would be, yeah, essentially a commodity version of the canvas made for the web. And turns out I, well, so far so good. I think I was right that there were a lot of people who had a lot of ideas about building those types of products, but it was hard to move those ideas forward because they would be like, oh God, who are we going to have to hire? A bunch of ex-Adobe people. We're going to have to spin up a team. And then how long did it take Figma to make their whiteboard or their canvas? Oh my God, it took years. Like, so if we want this thing to be good, it's going to be a huge investment.

What is— what would you say? I mean, The problem you're solving for developers, and it must really have changed their life, is building more easily, right? Faster. What do they tell you themselves? Like, how have you changed your life?

I think the number one thing that I hear when I talk to our kind of developer community or the people choosing TealDraw is that they would not have built this without TealDraw. So it's not even a— I mean, if I, you know, had an idea for a, you know, like a creative writing app and stuff. But in order to build that app, I had to make a text editor like myself. Like, I just wouldn't build that. I'd build something else. It just doesn't make sense. And so a lot of these features or integrations just didn't exist before, or the type of product that they were building just wasn't realistic before this, that they would have had to find some sort of technology to build on top of in order to kind of make it make sense for a seed stage company or make it make sense for something that they can ship without having to spin up a whole new team.

You didn't start your career in this space per se. You were, I think, can I say an artist in the early days?

I was an artist in the same way that many artists are artists, which is to say that I studied art and I did my master's and I, from you know, went quite deep into this. I was also doing a lot of writing about art, so reviews for magazines and essays for artists and other pieces of writing. And then I had my studio practice as well. And then on the side, I would be doing these open source projects around not necessarily design, but like visual problems, like pressure-sensitive digital ink was my thing. Yeah.

I heard you talk about this, like how you were trying to make an arrow look perfect.

Yeah, it started with arrows. But it got into ink eventually. You know how like on like an iPad or something where you're writing or drawing and if you push hard it'll kind of get a thicker line and if you push thin—

And it's so hard to write on an iPad, I know. If you can solve for that.

But I got totally into it and, you know, I tend to build things in public or on Twitter. And so there was a good 6 months where if you were following me on Twitter, you were just seeing a bunch of calligraphic kind of like Haze or something as I was dialing in this.

And that's how you started Tildraw, right? In 2021, in the open. Yeah, as a side project. How come you were— how come you wanted to do that in the open? Like all of these projects?

There's a lot of build in public advice out there and For me, number one, like as an artist, you're constantly sharing work in progress and you're inviting people over to your studio and you're, you know, you're soliciting feedback and sharing your work, not just when it's done, but like kind of along the way. And that's a really great practice and like kind of just a thing that I love to do and I'd love to see from other artists. And so I brought that with me when I kind of came into design and came into tech, this idea of just constantly be kind of sharing the work, connecting with other people who are doing similar things, but also connecting with people who maybe like could be customers or could be users or could be like eventually employers as well. There's a whole lot of reasons why you would do things in public. Like it's a bit like blogging. It's just like the best way to search in a way for people who are who like to find your community of people who are interested in the same thing.

Okay.

So like a blog post is like a really high effort Google search in a way, or a really high effort, you know, LinkedIn search.

So I want to understand you were there as a side project building Tildraw in the open. Open, sorry. And then how, how did it like start growing? And tell me more about the inflection point where you were like, Okay, this is not a side project anymore. It's a real business.

So when I was working on Perfect Freehand and Perfect, um, Arrows, this, you know, arrows and ink algorithms, these kind of precursor projects, eventually when I started working on TealDraw, TealDraw was kind of a collection of a lot of these different projects into a single project. Uh, and it was, it was meant to be Yeah, just an essentially open source SDK for building whiteboards and— yeah, sorry, software developer kit, right? So tool— toolkit for people building whiteboards and whiteboard-like things. And that let me investigate kind of these really gnarly design tool UX patterns like resizing and things like that. And that project, unlike the And once I started this open source whiteboard SDK or canvas SDK, suddenly the interest changed and the, like, it was a huge level shift. Like, my people started emailing me being like, hey, I've wanted to build one of these, but I haven't. Can we have early access to this code? And I'm like, no, I'll open source it later, but for now I'm just kind of working on it. And then that didn't stop. And in fact, the types of companies that were talking to me were a lot larger, you know. So I said, all right, if anyone's a sponsor of me on GitHub, like, you can access TealDraw.com. It doesn't matter how much, but you, you know, log in with GitHub and I'll check. And, you know, so I had a ton of like just $1 sponsors of people who wanted to see it or who were following along the story and a couple hundred of them by the peak. And also it started getting emails from large companies that were like, hey, we're working on a project like this. We're trying to upgrade our conferencing software's, you know, whiteboard, and it seems like you're building the thing that we would want to build on top of. Can we hire you, number one? And I said no. And then like, can we like get early access? And I said, yeah, like $75,000 and I'll give you early access. And they're like, yeah, of course, sure, right on. And so now I started picking up like corporate sponsors as well. And by the— and eventually I was— I had to go back to my current job and say, hey, I need to end my contract. I think I need to go full time on this. Because it's really a lot.

Were you scared when you did that?

No.

Or it was enough? You thought enough proof that you had like real traction? I think it was.

I mean, you're a founder, you dream about inbound traction like that. This was clearly something. I mean, I'd had enough, like, exciting traction moments with previous projects, but this was just an order of magnitude more, like, pull. And I was like, all right, either way, let's end this contract. Let's work on TealDraw for at least a couple months until I figure out whether I want to do TealDraw or sell it to someone or go work for one of these companies. And I did eventually sign a contract to come work for one of them. But I told them, hey, give me 6 months to get this, get this open source thing out of my system, the SteelDraw thing. And it continued to grow. I kept adding sponsors and corporate sponsors. Probably by the time that I decided, okay, I'm going to raise some money, I'd had like more than $200,000 of just sponsorship. So just stay unemployed, please. Money. And I launched it, got rid of that sponsor wall, just, you know, now it's public. Here's all the code, source code, MIT licensed everything. Oh. And just kind of put it out in the world. And my expectation was either this is going to have a— be very successful. Well, I didn't even expect it to be super successful, but it should be a medium-sized, cool open source project that eventually I'd find other maintainers for and just hand off and go do something else. But the response was really, really good and was really good from individuals who loved using the tealdraw.com, the kind of the demo of the whiteboard. And it was really strong from companies and startups who wanted to build these types of like infinite canvas apps. And that's when I decided, okay, I'll go raise some money. And I'd also had a lot of interest from, from investors. So I did my seed round in like 3 weeks or something. So it was very compressed. I had a lot of early validation of that this is something that people wanted. Um, and then I, I didn't make any money for about a year and a half after that.

So if I were to summarize it, you started, um, gathering a bit of money through sponsorships, and then after you've raised, that's when you had a paid model that came in. How does it look like, this paid model? Is it like, is it a free, premium thing?

We're on like the third iteration of this model. Business model fit is hard. So the way that it works is if you want to use TealDraw in development, so like hosted on your own computer, kind of like the way that the environment in which you would be coding and developing a piece of software, you can do that. You don't need to get a license. You don't need to talk to anyone. You don't need to pay me anything, right? You can just grab that. If you want to put it into production, if you want to use TealDraw in that separate setting, well, then you do need a license. It's not priced based on how many users or it's not priced based on how many, how big the team is.

It's just a license per year, right?

Annual license for that.

Okay, great.

So I think over time the kind of the terms and the quantifiable parts of what we sell are going to kind of stabilize and shake out. But yeah, unfortunately there's no business model that I can copy.

Yeah.

Feel free to copy TealDraw as it's working.

Do you have advice to give founders who are looking to grow their company through community? I know it can be interesting for certain types product. So how do you know if community is the right level for you as a company? And then what are— how do you do that? Like, how does it work?

I think with community, sometimes you have products where you have a lot of like horizontal conversation between community members. Then you have other products where it's more vertical, right? Where you have a team that's working and they're kind of like sharing updates. I think TealDraw is more vertical, honestly, like, which really just means we have a lot to do to actually create that horizontal community. It's just that we've, we've been sharing like really strange and interesting things for, for years, uh, including a lot of the AI stuff, which is how it got, got, um, a lot of attention there. Uh, and these experimental features that we've built on top of the canvas. Or the canvas itself. We're increasingly sharing like our customer projects, which are very interesting and unusual. So, I think we have more followers than community members. So, I can't speak as much to building big horizontal communities because I don't think we've really figured that out for us. But for the more vertical, like how do you just get people to know about your project and follow it, I think Sharing things that are— there's like a moment where I'm working on something and I turn to the person next to me and I say, hey, check this out. Something like that. That is a moment that you could share with your community or something. Even if it's not ready, even if it's a bug, especially if it's a bug, honestly, or if it's like unresolved behavior or something.

How does AI today— is opening new frontiers for Tildraw?

Yeah.

And also try to give a concrete example of how AI is elevating your product.

The Tildraw.com experience right now doesn't have any AI in it. We might do some things, but that's still sort of being figured out. The developer kit also doesn't really have any AI in it either, but you could build on top of it and build AI features on top of it. We've been building stuff on top of TealDraw since, since pretty early days, like GPT-2 type of days, but it wasn't very good until the vision models came out. But the, for us, it was actually a designer at Figma, Sawyer Hood, who's great, who like the day that that came out was like, oh cool, you could take, you could draw a website, then in TealDraw, and then send that to GPT-4 with vision and say, hey, make the actual website based on my drawing. And it would send it to— send the screenshot of what you made to an AI and say, hey, AI, you are a senior developer. You're 4,000 years old. You work with designers who send you lo-fi stuff and you send back the working prototypes. I think you love your designers and want them to be happy was one of the key parts of that prompt, which a lot of other companies have copied. If you ever search on GitHub, for you love your designers, I want them to be happy.

What would you think this prompt does?

The prompt just turns— it creates HTML, CSS.

Make them happy.

I don't know.

Like if you don't have it, are they going to turn like a very ugly image of your—

It was like, I don't know.

Make them happy.

It had a little bit of personality, made it try a little harder. I'm not sure. It might have just been— there's a lot of like incantations and magic around prompting. So it's probably one of those. But anyway, It would give us HTML, CSS, like a single page website. We would put that in an iframe. So in like a little website within the website on the canvas.

Okay.

And so there it is right there back on the canvas. And we can do that in TealDraw because the canvas is like a website and you can put websites inside of other websites.

Crazy.

Yeah. And this is kind of like Notion embeds. It's the same idea, right?

Yeah.

But in this case, it's on a canvas. And the cool next thing, the kind of the next turn of the complexity was when we realized that we could draw on top of the website and then send that as the next one. So we would like essentially be marking it up like you would with like a printout or something. And this went super viral. If you were on Twitter in November 2023, I'm sure you saw Make.Reel because it was getting like 10 million views, that type of things. Yeah. And it was, it was the first time. I mean, this was pre-Vibe coding apps and pre all that stuff. So it was like for a lot of people that we talked to, that was their first experience of this. That was their first experience of going from something as a non-technical person of saying, I have something in my head that would be software. Let me make the software.

I see. So I want to move to the last two sections of our, of our chat. The first one is you're building a tool for builders to build other tools. And now I want to know what are your favorite tools, the tools you use inside the company, inside Tildraw. So the first question is, can you tell us about the one tool that 10x'd your team's output?

We started building our own internal dashboard, internal tool, kind of like a mini Palantir for ourselves. And then I was like, what? Let me just take all that data for a particular deal and just kind of hand it to Gemini, you know, all the emails and meeting notes and all this stuff. And I'm like, just summarize this for me. But that was incredible. And suddenly, like, my sales team was using it too, you know, to learn about, yeah, what would be good next steps with this customer? What, you know, what's the angle that we go to or what's the pricing that we could expect? And then I kind of grew it from there saying like, you know what, why don't I do the same thing for our development? Where we look at all of our pull requests and issues and stuff like that and kind of visualize them and get all the information into the system as well, but also allow me or other people to, to get summaries of this information. And then we moved on to project management as well. So we actually kind of put, put Linear, which, which I love, but we kind of put it on hold and said, okay, everyone's going to use Notion for all of the task tracking and project tracking, so that it's in a single place. And we're going to use the same sort of pattern of like kind of pulling it into this dashboard, summarizing it, and now we're building kind of agents that can kind of search across all of that information and answer your questions at a very high level of saying, hey, You know, what did, what did Steve work on this last week? But it is, yeah. So it's a little bit of like we use it for like knowledge management, kind of like a team wiki as well as for, for like a task tracker type of thing.

If a founder is starting for the first time building their own, their first company ever, what do you think they should be focusing on or what's like your most important single piece of advice you want to give them?

I tend to actually give myself a lot of freedom to not necessarily focus. There are the things that really matter of like, you know, are we shipping on time? Are we making deals? Are we, you know, what's the size of those deals, etc.? Are the deals that we want? And those are like that's what really matters, right? That's the surface, that's the top. But how we get there can be really, really quite— look quite random in the moment and feel quite random in the moment. But I think that that's, you know, to limit yourself to the moves and the actions and the tasks where you could justify them against some future outcome is quite a huge limitation. That only gives you a couple of moves that you can make at any time. For founders, like, especially early on where you are looking for product market fit or you are looking for your, you know, what should this thing be? I mean, I didn't, I didn't like end up— I'd like— I didn't start with TealDraw. I didn't start with like a really good idea. I kind of arrived there via lots and lots of other things. Some of which were like, didn't go anywhere, you know, so it was this like a lot of noise on the line before I found, or kind of came into something that connected with a lot of people. But yeah, I guess my advice would be to just try things and give up on them very quickly. And yeah, kind of like worm your way towards what matters.

Yeah, well, thank you so much, Steve. I really enjoyed this conversation.

Thanks for having me.