E04 - How to design a profitable software startup

Hi, my name is Mike and this is The Goods. On this show, we go inside the minds of designers of all kinds. You'll discover their methods, mindset, you can use their to bring your ideas to life. Steve Shuffle Co-founder of Whimsical, a workspace where you can visualize your ideas as soon as you have them. Steve's a designer and a lifelong learner passionate about craftsmanship, remote work.

and building a future you want to live in. In our conversation, we explore how Whimsical became profitable, the secret behind their growth, how Steve and the team benefit from remote work, and if you make it all the way to the end, Steve has an Easter egg.

to play with so settle in and listen out for that this is one of the most in-depth interviews of the goods yet and it's a real privilege for me to have this conversation share Steve's story so without further I hope you enjoy the behind-the-scenes, of designing a software startup a whimsical Hey Steve, welcome to the show. Hey, thanks so much. I want to kick off at the very beginning and talk a little bit about how you discovered design, like what drew you into design itself.

Yeah, I actually came into design rather late. and it was almost accidental. I was back in college, and I was a couple years in. And I was playing lacrosse and pretty focused on that. And I was doing an English major.

And I hadn't really done much at all around design. And I had a teammate just kind of out of the blue mentioned he was doing a drawing class to a few of us. And he was like, you know might sound silly to some of you guys but anybody want to join me and i think i've taken like a mandatory class a number of years back and and had generally good memories from that and so i was like yeah like i'm down and um what i quickly realized was that

Everything in the art department was way more interesting and fun to me than everything else that I had been taking previously. And it kind of opened up this whole new direction for me. And I really just. basically started this exploration process into more visual feels. Got it. Was that like a life drawing class that you attended, or was it something else?

it was it was really basic I think it was like an intro just basic basic drawing and but it got me hooked and I from that point on I just started taking more and more kind of whatever they were offering it was like metal welding and um we did 3d modeling and paint like just painting and um there was some photoshop and illustrator classes sprinkled in so there's some some digital work but uh

yeah super broad really fun photography film kind of everything and from that time what was the kind of work the artistic kind of work that you really started to resonate with was it um was there something in particular that you found most exciting I think I really enjoyed the style of work, which was just very kind of chill, project-based. You could just kind of jam on something for quite a while. semester-long painting that I did as this side study.

and I had it set up in my apartment with my two roommates at the time. And it started kind of rough, like you're just kind of roughing in the background and everything. And I think they literally thought I was out of my mind. but um as like the weeks went by and there's like some more detail filled in and and whatnot they really started to get like into it and then they like would like kind of check in on me and like start watching I don't know. I think I just realized what it was.

Those types of classes and that type of work just spoke to me on kind of a deeper level. It resonated in a way that a lot of the other stuff wasn't. And so... I think I saw it more as just this exploration time. There wasn't one specific thing that I was after or trying to achieve, but just kind of... experimenting. Got it. And what was the painting of, out of curiosity? Yeah, it was of a barn. So outside of Duke, where I went to college, there...

I don't even know. I think I was doing some film experiment and I snapped a picture of this cool barn that was like on the side of the road. Somehow decided to paint that. It's a... it turned out like pretty decent and I forgot about it for a couple years and then after I got married and we were like living in a house it resurfaced and I looked back at it and I was like wow like I didn't even I mean I remember doing it but it was even better like

I was like, wow, okay, it's been a while, but it turned out okay. So it hung on our wall for a couple years. So it was kind of fun.

Yeah, wow. I've recently caught up with my parents who are now retired who have just caravaned down from Bribie Island in Australia all the way to Melbourne and they bought in the back of their caravan this like A1 size colour pencil sketch that I did that must have been a decade ago and it was like whoa I really explored some obscure artistic stuff back in the day it's really quite interesting it's amazing

But it's nice to see that evolution of where you kind of started and then where you're exploring now, because I think something I heard in what you were saying was that you were experimenting, you were exploring different things, and I think that's part of the process. And along those lines, I'm curious, given that you had a background in more like a traditional art, film, that kind of stuff, how did you determine or figure out that you wanted to design software? Right, so...

I did somewhere late in the mix, I took an intro to web class. It wasn't until my fourth year of college. And I think that was a big moment for me because up until that point I was kind of going along taking these different classes and at that during that class. it just felt like everything was kind of coming together and it was like oh okay I can use some of these skills here it brings in some of the photography or some of these visual elements and

So I think that was part of what turned me on to design and sharpened the focus a little bit. And it just kind of took it from there. Yeah. And what were some of those traditional skills that you think really carried across into software design? Well, I mean, I think one of the interesting things was that just moving forward a little bit. Once I realized that I wanted to do web design, digital design,

It was like, great, okay, I have a little bit of time in school left. Let's figure out how I can actually get a job doing this. So I found an internship at a company that was in the same city as the college I was going to. It seemed like it was going to be a perfect fit and I was so stoked about it. They did awesome work and they seemed like really great people.

And I got all my stuff together and applied. And basically what happened was they were like, um, look, like you don't really have any you know, web experience and that might be a good thing to have if you're going to get this internship. And so I kind of found myself in this chicken and egg type of situation. Like, how are you supposed to get work if you don't have the job? And I think a lot of people find themselves in that spot at some point or another.

If we fast forward a little bit, During that application process, one of the important things which helped me land it eventually was some of the things in my portfolio, the art pieces. And the people who did the interview, they were actually just interested in some of these broader skills. They were like, wow, I'm really curious how you can bring that to the web and do that in a digital context.

So it was kind of fascinating to see that stuff come back up down the road when maybe I hadn't even spent that much time doing the digital work. But it was part of. showing at least a little bit of aptitude and a little bit of promise just to kind of get my foot in the door. Yeah, and what were those pieces that they were most interested in? Do you remember?

Well, I honestly think some of the painting stuff. I had kind of done just a couple of pieces there, and I remember that being one of the things that was of interest. Drop that picture of the barn in there for them. That's great. In that early stage of your career when you were just exploring that internship,

What were some of the challenges that you had to overcome? Like you mentioned, trying to get experience seemed to be a really, really hard thing to do. And I think that's a challenge that a lot of younger designers face. You're expected to have experience, but you don't have experience. So how do you get the experience that you're meant to have given that you've got no experience? It seems like a bit of a catch-22 for a lot of people. No, I think it's a tough spot to be in.

And I honestly, that was one of these moments where I felt.

just a little bit tested um because what happened was i had applied to the internship and they were like hey like you need some work and i was like oh shoot and so they basically denied me for the first time and um i was like okay well well you know i gotta figure this out um and what that led to was me just kind of There was a nonprofit that I was connected to at the time and figured out I could help them put a site together and do a CMS.

started learning what needed to happen to do that and took on some free projects around college and luckily you know i was still in school at the time and so i wasn't needing to like provide for myself like fully um but um Yeah, I think that was, Definitely one of the notable early challenges with getting started was being denied for that internship, having to figure it out, and I reapplied to the same internship because I...

After a year, I was still feeling like that was what I wanted to be doing. And it was at that point that I got in and then was offered a full-time role after the internship finished up. Yeah, and that... You mentioned, like, being knocked back. How did that impact what you did next? Like how did you kind of overcome that? Was that, was there some kind of like mental thing that you had to overcome?

Because it sounds like you were pretty dogged. You just came back and you kept trying to tackle that again and again. And I'm curious how you felt at the time and what you were thinking about. Yeah, I think that... i mean i remember the emotion that the feeling of it and you know it's kind of like a little bit of a punch in the gut you're like I thought this felt perfect or it seemed to line up. And, and then it's like, no, okay. Like close door. Okay.

You know, I think a lot of the context that I had was sports. i played a lot of sports growing up and played in college and um I was like, well, what do you do when you get knocked down? When you lose a game, you know, you don't pack it in. You just kind of get back out there and practice your skill and your skills. you know, kind of jump back in the ring. So I think... that was

Yeah, that was essentially it for me. I was kind of realizing, hey, this is a low moment, but we got to keep kind of pushing. Yeah, it sounds like you mentioned that you played lacrosse, right? Yeah, lacrosse. At Duke, was it? Yeah. So maybe like the... I imagine you get knocked down a lot. We don't really play lacrosse in Australia, but I imagine you get hit pretty hard, pretty...

pretty often yeah yeah no it's it's a fairly regular thing um in the game it's pretty physical game and and um and yeah that's kind of like part of my lacrosse story too is that I came from an area that wasn't like a hotbed it wasn't you know There were people left and right going to top schools. And so, you know, I had a lot of coaches tell me at the time, like, hey, look, like.

best of luck but you're not you're not our guy or you're you know you're undersized to play like we're looking for you know bigger um players and whatever it was and I in a similar way to getting into design I had one school kind of say hey look like We'd love for you to come play for us. And that was all I needed to get in and start doing work.

Back at that time when you were having those conversations, was there anyone in particular that whose advice perhaps made the most impact on you, it sounds like. you've got this very strong ability to overcome failure and keep going. And I'm wondering if there was a particular piece of advice or a person that maybe contributed something to you that gave you an access. I will say that from that general time, and it was once I was already in the internship,

I was basically in full-time learning mode and I did not have a ton of background, did not have a ton of skills. I had maybe some raw ability and kind of a eagerness to learn. And I think, a number of people who made a huge impact on me were just some of the senior designers at the agency that I got the job at and they just kind of took me under their wing and I went from like just not knowing really a thing and we did consistent kind of critiques and

just kind of worked through it and try to dig in deep and read some books, read some blogs and, um, kind of deepen my understanding. But I thought that, um, That was a critical time for me and just like a really helpful time just of learning and those guys kind of brought me along.

Is there anything that you learned back at that agency going through that critique process that you still kind of apply today even with your work at Whimsical? Yeah, it's interesting. I still keep in touch with them a lot and they're a customer of ours, which is really... Cool to see that come full circle. How is that, by the way, just people that perhaps mentored you now use the product that you make? How does that actually feel like? Yeah, it's wild, right?

you know I just have a ton of respect for those folks they're very very talented at what they do and uh so it's humbling in a way right that those guys have and girls they just a ton of talent themselves and I was always kind of the younger guy, the person who was kind of up and coming. And not to say that I've arrived or anything like that, but it is really cool to put something out there. And I think this has been the experience with Whimsical. It's like you've put something out there and.

It's just a couple people making it, but then so many people get to experience it. And so people have these different experiences and similar in some ways because they're all united by the product. and their experience with it. So yeah, it's really fascinating, but it's very cool to see. That's great. And maybe this is a great segue, and I'm hoping you can take me back to starting Whimsical. What actually prompted the idea behind it? Yeah, so with Whimsical...

It was kind of been a classic story of build it for yourself. My co-founder and I were at a tech company in Denver together and basically noticed that. The whole team was using a bunch of fragmented tools. And on top of that, a number of them just weren't particularly fun to use.

some of those were digital but like there was a time where we're using this physical whiteboard with a bunch of sticky notes that like kept falling off and um it was simple and there was a nice thing about that but you know it was pretty janky too like we had people like that were remote and we'd have to hold up a computer so that they could see the sticky board and um so i think that Um...

going through some of those experiences and at previous jobs as well. It just felt like there was like this opportunity to build a tool that we ourselves needed. And I think that was a huge part about the idea behind it. But I will say that my co-founder, Casper, Kind of peeled off and started working on Whimsical for about six months by himself, solo. And so a lot of the initial directional insight.

about the product and what it needed to be started with him. And then when I joined him six months in, then we kind of started working on it together and forming more of the vision moving on from that point. Yeah, and just to create the context for those who aren't familiar with Whimsical, how would you describe it to a complete stranger who's got absolutely no context?

Right. Yeah. So Whimsical is a suite of visual communication tools. And so our products allow remote teams to do a lot of the same things that you would do in person on a whiteboard. you can do them online and I like to say that it's kind of similar to a more visual version of G Suite. And so you can have multiple people in the same document at the same time. And you're just working on a little bit more visual type of work.

doing the types of things you would do on whiteboard instead of just text docs and spreadsheets like you do in G Suite. Yeah, great. It's actually funny. We've had this conversation a couple of times, but everyone that I know that uses Whimsical can't help it. tell me how much they love Whimsical and how excited they were that I was talking to you about the company that you created. So it's definitely for the designers that I know, it's made a big difference to them having access to it.

I'm kind of curious, you mentioned that Casper also worked on the idea for about six months. And I'd really like to dig into how you took it from that early idea where it was just like maybe two guys in a room to an actual fully fledged software startup. Can you walk us through what that looked like? Sure. Yeah. Um...

Well, first off, I have to give a ton of credit to Kaspers. He is this very rare mix of talents and experience and he's been building software for a long time and has this great breadth of skills so the fact that he was able to kind of work on this and just You know basically build the entire full stack app and get The MVP was pretty well underway by the time I got started and I think what it was at that point was

Let's build the core flowchart experience. That was our first product. And so just focused on some of the main activities that would need to be there for the flowchart creation process. You know, there's still... a decent amount of stuff that needed to happen. When I came on, we reskinned the whole app. We needed some things on the marketing side, so we needed to kind of... work on the logo and some of the visual assets for the brand and marketing site and so on.

It was this kind of mad dash and there's no actual deadline, but we launched about a month and a half after I joined him. So it was pretty quick. Out of curiosity, how did the two of you meet and decide that this was an idea that you wanted to do together? Right, so Casper's actually, he was one of the people who interviewed me for the company that we worked with.

together at um and uh yeah so we not knowing each other at all we had a great conversation in that interview i still remember it um just kind of talking about products and what we thought went into good products and And I think.

through the course of working together for a couple years we're working closely together but just observing each other and and kind of crossing paths every now and then i think we just um i developed a kind of admiration for his um skills and also how he carried himself and his integrity.

And then I think like kind of moving that forward when he decided to kind of step aside from um full contact where we were and start working on on whimsical we kind of kept in touch a little bit and um and had a few lunches over the course of a couple months and then there came a point where Gracias.

let's see I'm trying to remember exactly how it happened but basically I had been feeling that I wanted to do an early stage startup for quite a while and i kind of put it out there to him i said hey look like i don't know if it would ever make sense for us to work together I have a lot of respect for you, and I don't know what the timing would be like. Maybe it would be a year from now, maybe sooner. But I'm just putting it out there. I would really enjoy doing something like that.

And at the time he was like, you know, I've actually been considering applying to some of these accelerator programs. And one thing led to the other. And we were like.

like okay wow we've progressed pretty quickly here like are we talking about going in and doing this like kind of partnering up and so we kind of from that that lunch conversation um we went back talked to our wives and um did some you know soul searching for the next couple weeks but um that was kind of the genesis and from there um kind of some other big pieces fell in place and we were off and running. Oh, that's really cool. You mentioned you were going to apply at some accelerator programs.

I'd like to dig into a little bit about after you guys had decided to work together, what perhaps gave you the confidence to commit to Whimsical as more than just a side project? It sounds like... You're in this stage of life where you both have wives, you've got families. I can imagine there's this whole conversation about the risks and the future. And can you just kind of walk us through what that was like at that time? Sure.

First of all, I think I never really considered it as a side project. It was from the start. It was always an all-in type of thing. And Casper's had already gone all-in on it and had been gone for a few months. And so... It was still a process for me, kind of.

going through the different factors in the pros and cons and was this the right opportunity and the right person to do it with and the right product to make a go of it because I think the common wisdom right is that if you're going to build a company of kind of significance then it's going to be kind of this seven to ten year type of thing minimum and so that's what i had in my mind i was like okay like am i ready to sign on for that um seven to ten or longer and

I think a big part for me was, one, like I've mentioned before, I really had a lot of confidence in Casper. I felt like he would be a great partner, and I thought that we had. A good... um... just we were able to collaborate well together and i thought that was gonna gonna be um good in that sense also you know in terms of risk i actually felt like there was a lot of upside, unlimited upside and a fairly limited downside. And so I'd actually, when I really thought about it,

Didn't feel like it was a super risky thing. I felt like, man. honestly i'd probably be bummed if i didn't take a shot here and um and also it felt like this was starting a company and being a part of an early stage startup was something I was being called to do. That was actually something on a deeper level that I was meant to do at some point. And I wasn't sure.

100% at the time that this was that company that I was supposed to help start. But it became... very apparent maybe a week two weeks after i made the fault like the the jump that i was like i was a hundred percent a hundred percent sure that it was the right call and um was so relieved and just loving it and, and have kind of sustained that. It's just kind of been one of those. Amazing. opportunities that has been the most fun, the most fulfilling work experiences that I've ever had.

out of curiosity you mentioned um you had a lot of confidence in casper your partner and i'm wondering if Maybe the confidence you had to commit to Whimsical or the confidence you had in the product came from him as a person and him as a partner. So it's not necessarily about the product you're working on. It was more about...

who you could work with or who you could be together as a team and then how you might tackle work. Would you say like the team and working with him was a real foundation of what gave you that confidence?

Yeah, I think that is a pretty good way of putting it because that's funny to admit it right now, but I... I didn't see the complete vision for... whimsical as a as a product early on i was a little concerned actually i was like okay flowcharts like um i knew like lucidchart existed and i'm like okay you know they've raised some money it seems like they have some like a number of big clients and traction there so um it seems like okay you know

You can build a good-sized business here. But there was some concern there, like, you know, am I interested enough in this particular thing? And is it a big enough market? I do think, and I don't know that I knew for sure at that point, but especially now having worked together for the last couple of years, There is a sense where it doesn't quite matter. Like, I'm just excited that we get to build software together and it feels like, wow.

What's in front of us is just a bunch of opportunity and really... cool, fun stuff that we can do and not so much like, oh, are we going to be able to do it or is it going to be good or bad or whatever it is? But it really just feels kind of this invigorating sense of what could be and that. We're going to put our heads down and try to make something cool that we're really proud of. And kind of figure it out together. Yeah, exactly. Cool. Back in the beginning.

I wanted to jump back. You mentioned vision a couple of times and, Where I wanted to unpack a bit more was how you found balancing moving fast while creating a vision for the future because I can imagine it's pretty difficult to do the two simultaneously. I think some of the vision came from some of those early conversations where it was just the two of us. And we were working out of Casper's basement at the time.

You know, we would just kind of go walk around the neighborhood and just talk about ideas or where things could go and kind of just imagine what we could be doing or how the product could evolve. So I think some of the vision came from that, some of those early conversations of just dreaming. And interestingly, it came together pretty quickly, at least just the high-level idea.

And that was very freeing in a way because we could just put our heads down and be like, oh yeah, that's generally where we're going and let's start going there.

For instance, when we first launched Fudge Arts, we had wireframes sticky notes and mind maps kind of teased up in the top as like coming soon and so we kind of put that out there to everybody that that's where we were headed and that was from the very beginning and it's kind of cool that it actually worked out that way that we went on to build those things so

Given the beginning where you started, you've had this vision, you knew you were going to start with flowcharts and maybe move forward to the other product lines. How would you or what would you say would be the secret to Whimsical's growth? uh to allow allow you guys to actually progress forward from there yeah i think there's probably not like a real secret um

I'm a big fan of Paul Graham and have read a bunch of his essays. And so one of these is just one of the things he loves to say and is make something people love, you know, and, kind of boil it down to something very simple that you can really grasp. Make something people love, that they find useful, that they're actually willing to pay you money for. And a lot of things just come out of that.

totally have been our experience as get that first thing right and some other things will fall in line um the other thing that's been tremendously helpful for us is having a growth engine built in, in the sense that... Our tool is a communication tool and it just inherently spreads itself. So you're adding people to your workspace or you're creating work and then sharing it with someone, whether that's a teammate or a client or whatever it is. And so that has been huge and really helpful.

in the sense that it just grows itself and kind of day after day, new people kind of coming in the doors and experiencing it and then kind of perpetuating this cycle. probably been one of the single biggest contributors to growth. It's interesting where I work. I remember the early days when we were using Lucidchart and how painful it was to actually use it and how long it took to put together these flowcharts.

And I remember one day very early on, one of our product managers I think found the tool and started wireframing or flowcharting stuff together quite quickly. and then sent out the link and I was like, wow, what is this tool? This looks fantastic. And then I like went on this whole rabbit hole and then I started using it and suddenly it like, it carved down being the need to like spend an hour on a flow chart to about 10 minutes. And I was like,

this is the way, like, this is the future. We need to have this tool and I need to help spread it throughout the rest of the company. That's awesome. And I just, I remember thinking that at the very start, You'd just done something so right in that. you thought about the needs of people like me and like the product manager that introduced it where we're pretty time poor. And this thing that we're working on is not like the final output. This is like one step to get there.

You really made it easy with Whimsical for us to get past that step or get past that hurdle to allow us to do or get to the... the coded part of the page or whatever the next step was but you didn't have that step be such an effortful thing you've really made that quite effortless for us so I really think that focusing on that experience really enabled us to then share it on because we knew that everyone else would benefit from this tool as well.

and then flash forward six months later and suddenly no one's using Lucidchart. We've got a whimsical account and like, yeah, your growth engine worked. Yeah, that's amazing. That's so cool to hear. I love that. And honestly, kind of going back to some of the core product, just principles or philosophies, we were just boiling it down to let's make this thing fast.

fun to use, beautiful output, and collaborative. You know, just kind of some of these core words that we kept coming back to. And when we were right about the products, those were the words that always kind of came to mind. Like, this is... what we had in mind and these are the things that we did in order to make it that way and um so it's really awesome to

Here, people can use the product and experience some of those things and have it save them time. Or, you know, you have certain users like engineers typically will say like, I'm creating this thing that looks way better than it should and I'm so psyched and like, thank you. It was pretty fun.

How is it for you? How does that make you feel when you hear feedback like that coming from an engineer about the product? Oh, it's really cool. I honestly think that Getting good feedback where people just are loving the tool and are excited about it is one of the coolest feelings. Hands down of the whole deal. Watching.

People yeah get in touch with us and and say some of those things it feels amazing watching people upgrade and and actually like pay for the tool is sort of surreal too um still just like It kind of blows my mind, but it's a really cool thing. And outside of that, um,

growth engine that you mentioned is baked into Whimsical? Were there any other ways in the beginning where you were perhaps doing guerrilla marketing or how did you distribute Whimsical to find like a core base of users to then have that growth engine kind of kick into gear? Right. One of the really helpful things is that we did a couple of different launches, one for each of the products, each of the four products that came out. And we did each of those on product hunt.

which was a great source of users and just kind of jump-starting things for us. With each of those, we would do a blog post and a launch video, and we'd kind of have things ready. And we'd also try to get into some newsletters and some forums like Designer News or Sidebar, some of these. some of these places where a lot of the designers specifically and you know some product people hang out.

So some of those channels were really helpful for us, especially when literally no one had heard of us. And yeah, at that point it was just like do things that don't scale. troll Twitter and talk to anyone who is looking for what we think we have. But those are some of the big things. And what were some of the early challenges in that stage where you were perhaps trying to grow? What was it like to really build Whimsical in those early days? I think

A couple of challenges come to mind. One was just that SaaS in general, like a subscription tool, is a really slow ramp. Each person is only paying you 10 bucks a pop.

And while that's great, it's going to take quite a few people to do that in order to have a substantial amount of revenue. So it's a slow ramp at the beginning. And at that point, we were just so excited that... people who are finding the app and signing up and some of them upgrading that you're just you know had plenty of energy to just keep going and pushing and but um

I think another thing related to that is that early on the core experience is there, but man there's not a whole lot else. It really did not have a whole lot there. And, you know, the collaboration features were not there. Just a lot of the stuff around the periphery. It was just we had that kind of basic flow charting experience and luckily that carried it enough. And with each new launch.

came out with we kept the prices exactly the same and so it was really cool to see the compounding effect of some of these new products coming in and helping us just with that kind of cost of value equation that each person is encountering where they're like, okay, is it worth it? And, you know, the more tools that we include with that, the more value that we're giving the users, I think that's becoming easier. which is really cool to see.

And was it a strategic choice to start with flowcharts and not with, say, mind maps or wireframes? Why did you zone in the beginning on flowcharts? What was it about it that you really thought would be the best place to start? Yeah, you know... You'll have to ask Casper's. I don't know, actually. I can't remember why he wanted to start there. I think it's the one that we used probably the most.

at the job before. And so he kind of made that call and started down that path. And we weren't sure what we would do next. We actually thought maybe we would do sticky notes second. We ended up doing wireframes, partially because a lot of people were asking for it. You know, we had those tees up top and inside the app. And so people saw it and they'd reach out like, when is this coming? When's that coming? Which is always fun.

the other thing was that we have these contextual toolbars so the little toolbars that pop up right above the object that you have selected and it was a really helpful just kind of

interaction pattern that started us down this road of figuring out how to do that for the other use cases. And I remember we had our first kid or it was like one year old at the time and i was up a lot during the night and in the middle of the night just holding him and um hanging out and it was just a pretty awesome memory actually memories of these times where i would just be in this dark room with white noise like walking around in circles but just kind of

thinking about the product and it was it was during that time actually that I was like you know what I honestly think with these contextual toolbars we can build one of the coolest wireframing apps that's ever been built. And I just had a lot of excitement and enthusiasm myself. And when we had some of the users asking for it as well, it kind of felt like that was the next place to go. And that was just like kind of came together that way and was really fun to build and really awesome to.

have it as a concept just in our minds and then watch it come to real life. I'll come back to contextual toolbars a little bit later, but I wanted to drill down into... Your decision to stay bootstrapped versus seeking investment because you mentioned that...

You're applying at one of these accelerator programs. Why did you make that call to stay bootstrap? And for context for the audience, bootstrap meaning staying self-funded and kind of... growing slowly over time with revenue based on profits from the business. Yeah, and when the topic first came up, it wasn't 100% clear what path we should take. And we did apply to Y Combinator and Techstar as a couple of these accelerators.

And it was a huge blessing that we didn't get it because it forced us to just launch and figure it out. I think that was probably the best thing that could have happened to us. And then it became this decision of, oh, what are the real reasons to raise money? What are we going to be missing out on if we don't? And what are we going to be missing out on if we do? And I think some of the...

Huge things for us is that just a month or two in, when we were working together, it was like this is the most fun that I've ever had. I don't want this to end. I don't want to mess it up. We want to build a long-term company that's going to be around for decades. Let's just keep this going. I think there's A lot. influence in the venture capital space of this kind of all or nothing, go big or go home. Maybe you get acquired or something else like this happens, but then your product

kind of going away. And we didn't want that. We wanted to give ourselves the best chance possible that we'd be here for the long term. And honestly, I think a big part of that was realizing that we thought we could do it. like without the outside money. You know, we didn't know for sure. It was hard to say. And we had just maybe not even launched the product when we were having some of these conversations.

And just realizing that some businesses don't have that opportunity, but it felt achievable for us. And I think in hindsight, it's been one of the top one or two decisions that we've made so far. And we haven't said that. There's no way that we wouldn't raise money in the future at some point. I don't think necessarily we're saying that. for the entire life of the company, but it has been so crucial for these early years.

Especially now that we're profitable, I think it kind of opens up all sorts of possibilities of just dreaming about having the freedom to take these big bets and to be mission first.

to like, I guess be led by something higher than producing profits like sure you know we want we want to kind of continue to grow and produce profits but it's like man what can we do and so i think some of these conversations have been incredibly um fun and just dreaming about where the company can go and what's possible because we are self-funded and independent.

You mentioned being profitable and I'm curious how that feels given that you were denied from the accelerator program to actually go out on your own and build like a functional profitable business.

yeah yeah you know it was kind of one of those things where with the SaaS model, it's just kind of chipping away, you know, and you get kind of each month, you get a little bit closer and then you know at some point we needed to have some teammates join us so it was just the two of us for a while and then we brought on a third guy and a fourth guy and that pushes back your you know profitability you know breakeven point

But yeah, it was a big kind of celebratory achievement when we hit it. And I think, I don't remember exactly when it was, maybe between a year and a year and a half. And I think that Yeah, things were kind of like building toward that. And then you kind of like pass it and then you keep going. And then it's like, great. Well, that's awesome. that's there and it should stay that way. And let's go figure out like the next.

cool stuff that we can do. And in practice at work, how has being bootstrapped impacted the way that you work at Whimsical? Are there certain decisions that you make or trade-offs you have to consider given that you've got no outside injection of capital? Yeah, I think trade-offs is a really good way of putting it. And I think there are some limiting factors, right? So you have to grow as your revenue grows. and you can't hire 100 people in a year.

You need to be more selective about what we work on because of that. and you're not using a lot of paid marketing typically. So you need to figure out other ways to do that and you need to have patience. But honestly, I think a lot of those things have been healthy. So if they sound like kind of... But I think they have been advantages in a lot of ways that we just have had. so much time to focus on our customers and the product and really nothing much else it's just um very focused

And so that's been huge and an amazing way to work. Really, really fun. I mean, when we're doing product work and building stuff, that's when I'm having the most fun. And it's kind of been nonstop for the last two years. I'm so amazing in that regard. So I think that that's kind of where it's freeing is that we're not spending time pitching and fundraising. And we furthermore, I think now that we're profitable, we can kind of say.

Okay, let's take a step back and evaluate what do we want to do? Where do we want to spend our time? We don't need to hit certain numbers for the business necessarily. Let's really... think hard about what we want to do next and have fun with it. Something I want to dig into now that you're kind of talking about this kind of stuff is

How did you think about designing the business, not just the product, but the business itself? Because you've mentioned a few things that I find to be quite remarkable, like you talk about. building a business that's at least going to last 10 years. You're talking about long-term thinking. You're talking about using or putting users first.

From my understanding, a lot of startups in the space, when they've got a big injection of capital, like they've got an incentive to... provide a return to their shareholders and they make sacrifices on vision for profitability but it sounds like you haven't got those traditional considerations to make and i'm wondering like What does it actually look like for you to design that business? What are the things that you're thinking about? And what's the context you carry on?

Yeah, that's a good question. I think that one of the helpful ways of thinking about it for us has been what type of company would we like to work for? what is that ideal type of working environment and culture and What are the characteristics of a dream company? Let's see if we can get as close as we can to that. And so some of those things have informed the larger decisions like bootstrapping, being remote first is another massive one. And I think that just affects.

the type of work or the style of work that we're doing. We're huge fans of just a remote, calm, asynchronous, minimum amount of meetings. And partially by the fact that we're just six people right now, but there's just not a lot of extra BS. just the things that kind of drag you down that can happen at some other bigger companies. And I'm sure we'll have to, you know.

fight those fights later when and if we continue to grow in terms of headcount but um i just have loved the simplicity of it of just being a small team that we can all collaborate and communicate easily and use our own tool. We have a big time zone difference between a number of our teammates who are in Latvia. And then a couple of us are in like Colorado, California in the U.S. And so really kind of leaning on an asynchronous work style. And, you know, we'll have kind of like a...

weekly meeting just to kind of kick off each week. But aside from that, just pretty light on meetings besides a few one-on-ones. And for anyone that's not familiar with the term, how would you describe async meetings or async to them? Yeah, so basically not necessarily needing to happen at the same time. so if you think of synchronous as like everything's kind of like real-time chat like slack um we strive to try to do a lot of our work just based on um you know

I'll do some work and then tag someone in a comment and kind of say, hey, when you get a chance, check this out. And so it's more. i think a style of i'll go do some work over here you got you do some work over there and then um you can kind of control when you're checking your messages and when you're kind of processing some of the things you've been asked to check in on. So asynchronous in that sense.

It sounds like you're baking calm into work, whereas I can imagine a lot of workplaces bake chaos into work. yeah yeah and again like it is simpler right with with a smaller number of folks but um i Know that There's larger companies that are working this way as well. And so we hope to keep kind of the same things alive.

you know maybe have to tweak some of the processes along the way but yeah it's been a really liberating way of working i love it um and uh it's just um yeah like i said just very calm and um you kind of take it at your own pace and uh a lot of time for deep work and focus. And what would you say, like I'm hearing a lot of stuff, but what do you think the benefits of this style of work are for you and everyone on the team?

Well, I mean, everybody's situation is a little bit different, but I was actually thinking the other day of a blog post, just like writing a love letter to remote work, just because, man, for the last two years, We have a three-year-old son and a one-year-old daughter, so it's kind of coincided with us having kids. That has been so helpful that those two have lined up because I think one of the biggest benefits of remote work that I've experienced is just like the ability to be around family.

And for me, that's just kind of like being around in the mornings for breakfast and hanging out and kind of checking back in at lunchtime or having like... a time to do a walk in the afternoon or right after work, cutting out the commute time.

yeah just kind of being very involved with with my my kids and my wife and um so that in and of itself has just been um this like huge tremendous blessing that i've been really really thankful for um and um i mean i think you can like kind of add a ton of other benefits, general benefits of just

kind of being able to work wherever you want you can travel it doesn't really matter where you're working from just kind of need your computer and an internet connection and so we've done some of that we've traveled um for you know week here week there maybe a little bit longer stretches um which is um really fun and just almost feels like it's uh like rigging the system like this shouldn't be fair like this is you know not real that you can just sort of pick up and go somewhere

and uh but that that's been it and you know i i think i enjoy kind of like the home office thing and um um still getting out for some like coffees or um lunches with with friends um or whatever it is but um yeah there's just so much possibility when you have that much flexibility. It reminds me of something you said earlier in that you were setting out to design the company that you wanted to work for.

And I think a lot of those things that you spoke about are things that anyone would really want, right? Like the ability to have flexibility and where you're working, cutting out commute times, like a lot of the pain points of... modern work you've essentially just removed from the process which is really cool.

Yes, absolutely. And I mean, connected to that, too, is when you start a company, you kind of determine like you have equity and upside in the business and so not only does it you kind of have the freedom and the flexibility around like working from home or working wherever you want to work but also the sense of in a company that we'd want to work for, there would be meaningful equity, not just for the founders, but for...

everybody that joins. And so that's another thing that kind of one of those things of designing the company that you'd want to work for. We've felt like. There needs to be a smaller gap between the early team and the so-called founders, the first people in. So I think that is another really cool part of kind of coming up with some of that. larger structures of the business and how that can work.

And thinking about structures, putting the product aside for a second, how do you think about things like processes, meetings, sharing information, your communication flows? I guess create that for a remote company from the ground up. Even in our short couple years of existence, the company has changed a lot. Like when it was just two of us in a basement and then... When we add it, Mikey, the third guy.

Then we were kind of in remote mode and Casper's kind of moved up to Balder from Denver. And so then we were in remote mode and we kind of needed to rethink some of the processes there. and some of the communication patterns. honestly i think it's kind of just been let's go with what feels right um something that's lightweight that's um

that kind of works with everything else that we're doing and not overthinking it, just kind of trying to keep it simple. You know, nothing too heavy. And, you know, we've kind of like... There was a time where we didn't even have a weekly sync-up meeting, and then we added one of those. We were just talking this past week or two about what check-ins with

you know, progress updates, some notion of that, because we hadn't been doing regular check-ins there. We'd been using some hill charts from Basecamp's ShapeUp. and doing kind of some different types of things there. But honestly, I think the story has just been figuring it out as we're evolving and growing and what is... what seems to be lacking or what's going well and doing more of that.

I think it comes back to something that you were saying around almost like designing the things that don't scale. Like, you know, you're not solving the problems that you don't have. You're solving the problems that you do have when they show up at that moment in time. Yes, definitely. Yeah, I'm curious about your values as a company and how you think about operationalizing or demonstrating those values in behaviors that you practice on a regular basis. Can you talk through how that might look?

Sure, yeah. And I think In some ways, we're still establishing who we want to be. And we each kind of come into the company with our own values and what we care about. I think in how we... operationalize them, how we kind of bring them into our behaviors in the day to day. You know, we talk about them, we write about them a little bit. both internally and getting into a few blog posts. We'd love to do more of that.

Yeah, like I was saying, like with just six of us, we can still have conversations around like one dinner table. So when we get together, you know, every six months or so for like a summit. We, yeah, we'll just kind of like have meals together and talk about some of these things. And those are some of the best conversations, I think, where it's like, That's actually where, for 2019, we decided to plant a bunch of trees and offset our carbon.

footprint that's really cool and um yeah it was just kind of one of those things that one of the guys on the team um well came up with the idea and just championed it and felt passionate about it and everybody was on board and um so I think it's fun being at the size where just like an idea can kind of become a reality quite quickly.

And, you know, like I mentioned a little earlier, I think we're in the early stages of just dreaming where we could take this and how we could bake in our values even more. and kind of create the type of company that exists to um make the world a better place maybe that sounds cliche but but in a real sense like let's build an amazing product that's here to stay that people love using and let's of course like create

um, an amazing place for people to work at whimsical. And then let's see what else we can do on top of that. Like let's, let's, um, kind of use our profits and put kind of our money where our mouth is. And, and, um, and actually. and do some things with it. So it's exciting and feels like we're early on in it, but I'm really psyched about that stuff. yeah fantastic and speaking of uh the things that you can do i'm curious how you decide going back to the product

how you determine what to build versus what not to build. Like how do you make those decisions on a weekly or whatever cadence it looks like? Yeah. We've been building for ourselves primarily, especially in this first year and a half to two years. kind of said like let's build the mind mapping tool that that we want to use and um let's build the you know the wire framing tool and something that we would

really enjoy ourselves. So at a very high level, there's some of that. And then I think, you know, for the first year and a half i was doing like a vast majority of the kind of customer support and just chatting with people and um hearing their ideas and their feature requests and i think just kind of um Hearing those and kind of processing that. and just letting those kind of marinate a little bit and figuring out

what we wanted to incorporate and what made sense at what time. I think that's roughly how it's been going. And Casper's and I, I think, I'll just kind of... ¡Kip-bam!

throwing ideas back and forth and, um, um, what, what could be cool. And, and honestly, Casper has a really good mind for, um, I think that some of his, engineering, just kind of knowing technically how things fit together and what would make sense to do first and just setting a good foundation there and a good... timing for the different things we work on. Hmm.

You mentioned you're on the phones in the very early stages doing a lot of customer support. I'm very interested in... how you include feedback from your users and compare that. to input from your engineers, but then also weigh that against your own ideas for where the product should go or what features you should release.

Honestly, I think that it's I'm not a sophisticated system it's more just um a lot of just kind of instinct Also just kind of looking at things at a high level and saying like, okay, group these things together and that could be really cool and that could make a lot of sense.

you know lately we've been working in these six-week cycles as part of that shape up methodology and that's created some cool things in the sense that you kind of make a couple bets or you have these pitches that you'll kind of make these bets on and we've roughly more or less been following that system and It helps you to filter some of these inputs. into a couple tangible, we could go and build this, we could do that, we could do that, and keeping it fairly informal.

And honestly, just figuring out. And one of the things we tried to stick to, honestly, is what... What are our needs right now? And I mean, you can't follow that 100% because we aren't going to be exactly like every one of our customers. i think it helps us get close on some of the fundamental things some of the core stuff like directionally and so we've we've followed that and we're kind of continuing to do that and have some fun things in the works um that related to it.

Thinking about that a little bit more, some companies say that they're design-driven, some say that they're support-driven, some say that they are engineer-driven. How would you describe what drives Whimsical at its core? Yeah, I've thought about this some too. And I think that what Casper's and I feel is core to whimsical. is that it is, maybe you call it maker-driven. It's a combination of design and engineering. So the fact that He is an engineer, but also brings

a great design sensibility and kind of just a knack for interaction design. And then I'm kind of on the visual. side of things and bringing the design as well. And pretty early on, I think when we were kind of having some of those conversations, the types where we were just walking around the neighborhood.

Um, I was telling Casper's that one of these things that I get really excited about and it's kind of animating and energizing for me is just this thinking about building the best product that's ever existed or the best something you know the best company that's ever existed i'm just like fascinated by that and not to say that like we'd actually be able to achieve it maybe we would but But having that as the goal, like let's, let's.

set the sites extremely high, and let's go see what we can build. And he was like, actually, I think that's one of the things that we share and that it was one of these really interesting insights that we've come back to a number of times. in terms of using that as a criteria for hiring and kind of just calling it like this like craftsman mindset. So whether that makes us like, I would kind of maybe say,

I don't know if it's hockey, but maybe it's like a craftsman led company. Like we just got craftsmanship. as like a super important ideal. I think also on top of that as well like what you spoke about reminds me of like having a vision for the future something that you may not necessarily achieve but it kind of calls you forward and it calls you to look to continually improve and be better and not kind of become stayed and stuck.

and that's what I'm hearing a lot and what you're saying is there's this bigger push to be better at Whimsical and I can definitely see it in the product and I've been a user for over a year now at least and like every time like I see these emails from you it's like hey Mike you know here's what we're releasing like this month and I'm like oh god you're solving the problems that I've got I love this so much so yeah it's a real like I think testament to the

Maybe the philosophy of both you and Casper's and what you take on for Whimsical to constantly push for more and push for better. Yeah, thanks. I think that is at the core of what we both enjoy and value. it's really fun for me to have someone like Casper's who's just constantly building amazing things. And I'm just like, I'm like, so psyched and, you know, pumped up. I'm like, yes, like, this is amazing and so much fun. And let's keep doing this. Given that you're a fully remote team then,

What are some of the challenges that show up with remote work itself? Because you can't just, with Casper being in Boulder, you being in Denver, you can't just... you know open the door and you know casper's right there in the next room how do you what are some of the challenges and how do you kind of overcome those challenges while we're working remotely Yeah, I think that one of the biggest challenges that I've seen personally is maintaining connectedness.

That seems to be one of the difficult things that...

where an in-person experience just feels fundamentally different. When you're just kind of sharing a meal with someone, then you're... you know, some of those kind of small talk things and and you know you can kind of recreate that a little bit online but especially with the time zone differences which I think is another hard one for us in particular is you know you're not going to get a ton of like a vat like real-time chatting and, you know, Zoom call or whatever it is.

um so those feel like the big ones to me and you know we do we kind of do those six months every six months do a summit where we're in person um that's roughly the cadence that we're doing at this point at least and um um you know one of the other common ones it's it hasn't been a huge factor for me just because um but loneliness i think is something that's come up and um you know i've got like

kids screaming in the background at least now with my home office set up and um you know just like a lot going on it feels like but um but no i think that can be for sure and um So I think there is a general communication challenge with remote work. a big part of why we're building Whimsical. And also one of the really rewarding things about shipping new features and building new stuff is that with each of it, hopefully that we're improving. the communication options and And...

kind of improving that for ourselves. And are there any challenges around keeping everyone aligned in support of the vision while you work remotely? Yeah, you know, I think that that, like many of the other things, has been evolving. evolving thing for us like how do we all stay in sync and how do we do that best? And, you know, using Whimsical for a lot of the work that we're doing, like using our own tool, just kind of keeps us connected to things, which is maybe not like an opportunity that.

A lot of people have, but it's really helpful for us. Just on that, how does Whimsical use Whimsical? Out of curiosity. Yeah, like I remember seeing like a Figma designer saying like people ask me if it's weird designing Figma and Figma. And they had like two windows like stacked inside of each other. And they're like, it's not weird at all. Thankfully, we're not doing that, which would be really trippy.

So, you know, we're using sticky notes for all of our project management. So we've adopted kind of like a simple version of Hillchart. from Basecamp if you've seen those, but basically you're just kind of dragging a particular task up and over this hill and you can kind of see the progress that way. We're doing wireframes and brainstorming in MindMap. And just kind of using the basic tools, we...

Just had an integration go live with Notion in the last week or two, and we used Notion a bunch for just kind of text-based. work in collaboration so it's cool to see that kind of come together a little bit closer and because I think between Figma and Notion and Whimsical that's kind of like where we spend the vast majority of our time. But so it's, yeah, it's. Nice and it's been cool kind of bouncing between those and seeing them come together in a little way.

Fantastic. I do have one question from the product manager that introduced me to Whimsical and I thought I would feel terrible if I didn't get it in for her. She's very curious about how you tackled adding team accounts, the challenges around permissions and things like that. Can you talk through a little bit about how you approached that and what that was like? Right, sure. Well, first I'll say that it's like sneaky.

complicated or maybe maybe it's obviously complicated i'm not sure but um all the different permissions and the sharing settings and Just even what you call things, like what the names are for... The different types of groupings are kind of primitives for sharing. That's some tricky stuff. We were just talking about that today, honestly. It's like a continual refinement process. And, you know, getting the basics in, I think Casper's had been kind of mulling on that for a while.

It was, this has happened quite a bit, but it was kind of one of those things where he was like, yeah, you know, I don't know, it's probably going to take quite a while, a couple months.

you know, it's, it's pretty involved. I mean, he's like, I don't, I don't know fully, but I think it's pretty involved. And I'm like, Oh man. Okay. Yeah. I don't know when we'll get to that. And then, and then he'll be like, well, figured some things out and wasn't as bad as I thought and I think it should be ready by the end of the week and that's just like classic but

I think the real answer to it is that we're still figuring it out, and it's kind of like a piece-by-piece thing, which has kind of been the story of Whimsical a lot, is the iterative. I mean, I guess classic software design, but yeah, just iterative, adding kind of a feature here, a feature there. gradually getting to the place where you're solving most of the needs. I think it's still simplistic in some regards with the team collaboration. So there's probably some... Um,

improvements that will need to come there in the coming months. But yeah, we're just kind of responding to any like pressing needs and then trying to refine it as we go.

For sure. You've mentioned... the book shape up quite a few times and for those that don't know it's like from my understanding i've not personally read the book i've kind of read the overview that it's about how you shape products and features and things like that to deliver incrementally over time perhaps I was just curious, could you talk a little bit about how you use the concepts in that book and apply that at Whimsical? right we've kind of we all read it and um

Yannis, actually, one of our backend engineers did a huge mind map of it, which is cool, inside Whimsical. One way to use Whimsical, right? There you go. Yeah, it was pretty big. Is that public out of curiosity? I would love to see that. It could be. I can definitely send you the link because um i don't know that we actually like tweeted it out but we were kind of like should we like that's kind of cool um so i'll send it to you but um

I think we read the shape up and we're like, wow, there's some really helpful concepts in here. But when it came to actually implementing it for ourselves, you know, we kind of.

took our liberties and we're like, okay, we don't have to like 100% implement this. And some of it was just like, you know, Basecamp is a 60 person company or something like that and there's six of us and so we the ones doing the shaping which is are usually like the product people the product designer or you know the product strategy person um Um...

They have separate shaping people and implementing people, whereas it's just one and the same for us. We're shaping it and then building it. So we can be a little bit more lightweight with our process. But roughly... You're kind of calling out some of the problem that's being solved and your appetite for...

building it and the solution that you're kind of roughly sketching out. And I think that's one of the kind of core concepts is not being too prescriptive. But then again, like for us, it's like well, I'm the one that's going to design it. So, you know, we'll just kind of do whatever communicates effectively the concept that we're going after. And then we can kind of take it from there. Yeah, after we kind of, you kind of have some rabbit holes and no-goes.

Then we'll have a period of time where collecting some of those. big ideas in a board and then we'll start to piece those together in terms of what do we think we can get done in this cycle and what would be like a stretch. So that's maybe slightly different as well.

yeah we'll basically kind of say okay like you know this um you know you can take this this feature you can take this and um if we can get to it we'll we'll do this and that and um so it's still pretty you know, simple, pretty basic, but there's been a number of concepts that have just felt right from the get-go. And I know they've kind of been refining this over a number of years. And so we've benefited a lot from that. Perfect.

I wanted to shift gears again now. So I have reached out to a whole bunch of designers in my network and like ask them questions like, what would you love Steve from Whimsical to kind of talk about in this episode of the podcast? And I've got a few things that feel free to like run through rapid fire if we're time short. But if you don't mind, I'll jump into them. So one question that came up was, Why are contextual toolbars a fundamental element inside Whimsical?

Right. Contextual toolbars are fun. And I've honestly really come to love them. And there are some constraints with contextual toolbars just because... You only have a limited amount of space that you can really go before it starts to get out of control. I think one of the coolest things about them is they clean up the interface a ton because you only have to expose the relevant controls to the object that you have selected.

it really opens things up and you're not staring at like a wall of panels on all four sides of the product and instead you know we can and just strip away some of that and um and also just uh i think it reduces just kind of some of the cognitive overhead of um being like okay i need to do i need to like crop this image um where's that crop icon and you know you know kind of

digging through a menu as opposed to like okay well it's one of five icons that are sitting above this this image so um i just love how how tailored it is and um how it's expanded when we just did flow charts like there was um a number of

core objects but then when we did wireframes there's you know a couple dozen more that each had their own you know slightly different contextual toolbar and it's a it's a cool like surprisingly scalable structure that has Yeah, I think it's been really fun to work on that.

It's almost something that's like... flexible but easily replicatable and understandable as well because there's this element of consistency across the different product lines like you have that familiar behavior that you can expect as a user navigating between flowcharts to wireframes to sticky notes like it's all kind of consistent throughout the experience yeah that's great yeah it's it's surprisingly flexible like that um that it can cover like a pretty wide range of things and um

for me too like um just doing the design it's actually pretty fun um working on the icons i'm just gonna you know just when you're like zooming out on some of the stuff we've been talking about, but then you zoom all the way in and just kind of crafting some pixels and doing some icons. So I have fun with that too.

Fantastic. It's almost like I imagine your drawing class kind of coming back in a way, like getting down into those kind of details. Yeah, that's fine. So another question was, why did you decide to limit the color palette? Yeah, um... The colors have evolved a little bit in Whimsical, but initially we limited the colors in wireframes quite a bit.

in order for them to be semantic. It was one of those things that we felt about the wireframe tool is that all the color usage needed to convey meaning. so we kind of had for the most part one primary color and then we had like a destructive or like kind of error color and then we had an additive kind of success color so that for us was like sort of like a blue green red um blue red green

And then also just for like consistency to try to like maintain a beautiful aesthetic. And also like... kind of constraining the product and kind of helping people just work within those constraints i think can be um freeing and actually make people quicker um when they're not having to like deliberate between you know 10 shades of green um they can just pick the one green option and be on their way

Yeah, it reduces their decision-making fatigue about the right color of that shade of green. Yeah, totally. Why did you optimize left-handed shortcuts in whimsical wireframes? So we did that primarily for speed. it was kind of fun with a fun realization while we were building it it's like okay you have your right hand on the mouse most most people being right-handed um and uh the other the left hand's on the keyboard and so you can access

a bunch of the frequently used wireframing elements from the shortcut keys and so that was yeah one of those moments where I was like I think this could be a way to make it faster and easier to use and so we you know map them to the left hand a lot and i think another thing that enabled this was um we instead of creating one master toolbar inside of one board that could do everything.

we kind of separated out the use cases. So it was like you're either in flowchart mode or wireframe mode. And one of the things that let us do was have more tailored keyboard shortcuts, which was... Important for that. Fantastic. And as the founder, what are your favorite details behind Whimsical that maybe an average person doesn't notice? That's a fun question.

A couple of people have noticed this and I always love it when they do. One detail that I really personally enjoy is when you create a button in wireframes. and you go to add an icon for the button, we automatically search for whatever text you had entered for the button, and we pre-populate the icons.

So a lot of times it's just like staring you in the face. And so... you know if you're not like really paying attention it's just like oh it kind of works but then when you're like wait what just happened um it feels sort of like magic

so that's a really fun one for me that's a cute detail that's really cute yeah The other thing I think I'd say is, and we did this way back in the beginning and haven't done anything to it since, but the upgrade confirmation screen or like right after you press the like pay button We do this cool like geometric explosion of shapes and it says like woohoo and you know it's just like this fun thing that we put together. I did the animation in After Effects and then we used the Lottie plugin.

to bring it to life. But that's also a fun moment in the app. You're like celebrating that upgrade moment. Yeah, yeah, right. That's really cool. If you were to design Whimsical again from scratch, what might you change? Honestly, the first thing that comes to mind for me is something we... uh ironically have not completely fixed but um It's a...

The way that we do, this is kind of in the minutia of the app, but the way that we do the free plan where you put boards in the trash and, you know, you have like a quota of four free boards. It's just sort of confusing how it works, and we've had so many people reach out about it, and it's something that we've meant to... to improve and make more intuitive, but you kind of find some of those rough edges.

and and people just like pound you on it it's like just unrelenting yes unrelenting day after day after day and they don't notice the button but they just all they care about is that yeah yeah totally so that i think we were thought a little bit harder about getting it right the first time but um i think thankfully um a lot of the major decisions we made we probably stick with and um been pretty happy with

And final question from the other designers in my network. What do you wish you'd had known before you'd started out? Well... I definitely listen to a fair number of podcasts. and read a decent number of books about starting up and, you know, mentioned the Paul Graham essays, which were extremely helpful. So I don't think there's a huge number of massive surprises, but one of the things that has been apparent as we've been going about building Whimsical is that

You just really learn as you go. And you don't have to have everything figured out or everything perfect. You just get going. And I know that... There's a wide range of experiences that entrepreneurs have, but for me it's been such a rewarding and rich experience and I wouldn't trade it for anything. awesome and so I'm just glad that it was like made the the jump and just kind of go and do it and so that's I think you just go and you make it happen. And figure it out along the way. Absolutely.

And looking to the future, how do you keep your vision alive now that you're working with a team and thinking about the future as you may or may not scale? How do you really keep that? as the thing that drives the business forward. I think that going back to that craftsmanship model of doing work, We thought about that for sure with hiring. For instance, the most recent person that joined us is this amazing guy, amazing engineer. I literally thought about everybody I had worked with.

like in the past and i applied that i was like who who would be the most ideal person to join us. And it was incredible that the timing actually worked out and everything went through. So I do think hiring is a big part of... continuing the vision and bringing the right people that share the same interests and values and want to do some of the same cool things. Honestly, something as simple as just having a weekly lunch with, with Casper's where we can just kind of process things and chat about.

you know new ideas and how's that going and what could that what could we do there and um so that those those moments are cool and um He's actually, Kaspers is moving to Latvia soon, so those will be a little bit harder and a little farther in between. Yeah, I think I point to those lunches as being a big part of keeping the vision alive. Fantastic. So in terms of your journey, you started off.

doing drawing classes and you moved through to painting. You had an internship. You've tried to get into an accelerator program. You've built this company. It's become profitable. Now, given where you're at, what are the things when it comes to design that you really care about? some of the things that we've tried to build into Whimsical come to mind. So what do I care about with regards to design? Something that...

is simple and beautiful, something that communicates clearly or that allows other people to communicate clearly. I think that has been a really rewarding part of Whimsical is that you're kind of giving the tools to people. And saying here, go and do things and design them and build them and collaborate on them. kind of empowering other people to use the tools that we're building.

like a really cool part of design right now for me and we haven't really covered it up until this moment but um what is your vision for whimsical Well, I probably alluded to it because I think... When I think about my vision for Wimsicle, it's just create the best product and the best company that's ever existed. I kind of come back to that. And again, like not in a prideful way, not like... so much for us.

create that tool that people love and a company that is here for years and years and a sort of generational company and everything within that craftsmanship mindset. And if we can do those things or even just aspire toward them, then I'll be really proud and happy. Great. And just kind of wrapping up, what advice would you give to another young designer founder like yourself?

I think the biggest thing I would say is to find a really solid co-founder or co-founders people who have the skills but have the integrity and the grit and a collaborative spirit that you can riff off of. I think that has been so vital to... us kind of this thing like working out and there's so many steps along the way where you have to trust each other you have to both be just kind of getting things done on your side of it and pushing forward.

and working together and and so i think finding that right person is the first big step and really kind of the important one that carries you through. So we're like really creating a team. Yes, absolutely. Yeah. And finally, where can people learn more about you and where can they learn more about Whimsical? Yeah, I think Twitter and our blog are great ways to stay up with Whimsical.

I can definitely verify that the blog's got some great stories about how you've overcome some challenges and some of the details that you've kind of explored through the company. It's some of the research that I've personally done for this podcast. I think it's a great... piece of content for anyone that's curious about building product, building companies. Yeah, thanks so much. I'm hoping that we can put some more writing out there and kind of document the journey as we go.

Fantastic. Well, Steve, thank you so much for taking the time to speak with me, share your insights about growing Whimsical Design at Whimsical. It's been a fascinating conversation for me. I hope people listening got some value out of it. Yeah, I just wanted to say thank you so much, man. It's been such a pleasure. Yeah, thank you, Mike. Loved it. hey there it's mike again thank you for listening this far

Now, at the very start of this episode, I promised you a surprise. And you might have heard Steve from Whimsical mention this concept of shape-up a few times throughout the conversation. Well, ShapeUp's a process that a growing number of product teams around the world are using to think deeper about the right problems and to start making more meaningful projects.

The Whimsical team have been using ShapeUp for a while in their workflow and have actually broken it down into a mind map that you can access for free at whimsical.com forward slash ShapeUp. That link again is whimsical.com forward slash shape up. The mind map is a really great entry point into the concepts of shaping, bedding and building and it all links out directly to the chapters of shape up on basecamp.com.

The mind map will also give you a really great overview into the power of Whimsical, which I can't recommend enough. Please check that out. well this has been huge but everything good must come to an end if you like this episode and want to hear more you can get the goods on apple spotify or your favorite podcast network or listening app thank you for listening This is Mike signing off.