E04 - How to Design a Profitable Software Startup

Meet Steve Schoeffel, Co-Founder of Whimsical - a visual workspace made for teams.
March 31, 2020 | 01:41:09
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Meet Steve Schoeffel, Co-Founder of Whimsical - a visual workspace made for teams.

Steve's a Founder and Designer who is passionate about remote work, and building the future.

In this episode, you'll discover:

  • Why Whimsical chose to stay self-funded
  • The secrets behind their growth
  • How they decide what to build vs what not to
  • How Whimsical overcome the challenges of remote work
  • And, a whole lot more.

We've also got a surprise for you at the end of this episode.

So, settle in and listen out for that.

Enjoy!

Key Quotes from this episode

  • I think it kind of opens up all sorts of possibilities of like just dreaming about having the freedom to take these big bets and to be mission first, and to like I guess be led by something higher than producing profits. Like sure, we want to continue to grow and produce profits. But it's like, "Man, what can we do?" I think some of these conversations have been incredibly fun, just dreaming about where the company can go and what's possible.
  • You have to grow as your revenue grows. You can't hire 100 people in a year. You need to be more selective about what you work on, because of that.
  • 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 very focused and so that’s been huge and an amazing way to work, really, really fun.
  • It’s more, I think, a style of I’ll go do some work over here, you do some work over there. And then 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.
  • Again, it is simpler, right with the smaller number of folks. But I know that there are larger companies that are working this way as well. We have to keep kind of the same things live and maybe have to tweak some of the processes along the way.
  • But, honestly, I think it’s kind of just been let’s go with what feels right. Something that’s lightweight that kind of works with everything else that we’re doing and not overthinking it.
  • I think in some ways we’re still establishing who we want to be. And, you know, we each kind of come into the company with our own values and what we care about.
  • Maybe that sounds cliché, 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 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 kind of use our profits and put kind of our money where our mouth is, and actually then do some things with it.
  • 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 a just of a knack for interaction design.
  • Just people who have the skills but have the integrity, and the grit, and a collaborative spirit that you can riff off of. ... 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.

Questions I ask

01:17 - I want to kick you off at the very beginning and talk a little bit about how you discovered design. What drew you into design itself?

02:31 - Was that a life drawing class that you attended? Or was it something else?

03:15 - From that time what was the artistic kind of work that you really started to resonate with? Was there something in particular that you found most exciting?

04:49 - What was the painting of, out of curiosity?

06:09 - Given that you had a background in more a traditional art, film, that kind of stuff, how did you determine or figure out that you wanted to design software?

07:26 - What were some of those traditional skills that you think really carried across into software design?

09:30 - What were those pieces that you showed your former employers that they were most interested in? Do you remember?

09:48 - 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? You mentioned trying to get experience seemed to be a really hard thing to do, so how do you get the experience that you're meant to have, given that you've got no experience?

11:49 - You mentioned being knocked back. How did that impact what you did next? How did you overcome that? Was that some kind of mental thing that you had to overcome? What did you feel at the time and what you were thinking about?

14:22 - Back at that time when you were having those conversations, was there anyone in particular whose advice perhaps made the most impact on you? Was there a particular piece of advice or a person that maybe contributed something to you that gave you an access?

15:53 - Is there anything that you learned back at that agency, going through that critique process that you still apply today, even with your work at Whimsical?

16:11 - How does that feel, that people who mentored you now use the product that you make? What does that actually feel like?

17:21 - Let’s talk about starting Whimsical. What actually prompted the idea behind it?

19:14 - 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?

20:01 - You mentioned that your partner, Kaspars Dancis also worked on the idea for about six months. I'd really like to dig into how you took it from that early idea where it was just maybe two guys in a room to an actual fully-fledged software startup. Can you walk us through what that looked like?

22:15 - How did you and your business partner, Kaspars Dancis meet and decide that this was an idea that you wanted to do together?

24:56 - You mentioned you were going to apply to some accelerator programs. What gave you the confidence to commit to Whimsical as more than just a side project? Can you just walk us through what that was like at that time?

28:28 - You mentioned you had a lot of confidence in Kaspars, your partner. I'm wondering if maybe the confidence that 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. Would you say the team and working with him was a real foundation? What gave you that confidence?

30:44 - You mentioned vision a couple of times. I wanted to unpack a bit more, how you found balancing moving fast while creating a vision for the future. I can imagine it's pretty difficult to do the two simultaneously. What can you say about that?

32:27 - 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, what would you say would be the secret to Whimsical's growth to allow you guys to actually progress forward from there?

37:08 - How does that make you feel when you hear feedback coming from an engineer about the product?

37:57 - Outside of that growth engine that you mentioned is baked into Whimsical, were there any other ways in the beginning, where you were perhaps doing guerilla marketing? Or how did you distribute Whimsical to find a core base of users to then have that growth engine kick into gear?

39:16 - 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?

41:08 - Was it a strategic choice to start with Flowcharts and not with say, Mind Maps or Wireframes? Why did you zone in, in the in the beginning, on Flowcharts? What was it about it that you really thought it would be the best place to start?

43:26 - I wanted to drill down into your decision to stay bootstrapped versus seeking investment. Because you mentioned that you were applying at one of these accelerator programs. Why did you make that call to stay bootstrapped?

47:06 - You mentioned being profitable. Given that you were denied from the accelerator program, how does that feel to actually go out on your own and build a functional, profitable business?

48:25 - In practice at work, how has being bootstrapped impacted the way that you work at Whimsical? Are there are certain decisions that you make or tradeoffs you have to consider, given that you've got no outside injection of capital?

50:24 - How did you think about designing the business? Not just the product, but the business itself. It sounds like you haven't got those traditional considerations to make, if you had to do things for shareholders, for example. I'm wondering what does it actually look like for you to design that business? What are the things that you're thinking about? What's the context you carry on?

53:31 - For anyone that's not familiar with the term, how would you describe asynchronous meetings or “async” to them?

55:14 - What do you think the benefits of this style of work are for you and everyone on the team?

59:04 - Thinking about structures, putting the product aside for a second, how do you think about things like processes, meetings, sharing information, your communication flows? How do you create that for a remote company from the ground up?

61:19 - 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?

64:06 - Going back to the product, I'm curious how you decide or how you determine what to build versus what not to build. How do you make those decisions on a weekly or whatever cadence it looks like?

66:07 - 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. Can you tell me about that?

68:23 - Some companies say that they are 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?

72:08 - Given that you're a fully remote team then, what are some of the challenges that show up with remote work itself? What are some of the challenges and how do you overcome those challenges while we're working remotely?

74:33 - Are there any challenges around keeping everyone aligned in support of the vision while your work remotely?

75:15 - How does Whimsical, the company use Whimsical the app?

76:49 - How did you tackle adding team accounts? What were the challenges around permissions and things like that? Can you talk through a little bit about how you approach that and what that was like?

79:22 - You've mentioned the book Shape Up quite a few times. Could you talk a little bit about how you use the concepts in that book and apply that at Whimsical?

80:10 - Is that Mind Map you created for the book Shape Up public?

82:52 - Why are Contextual toolbars a fundamental element inside Whimsical?

86:07 - Why did you decide to limit the color palette?

87:37 - Why did you optimize left handed shortcuts in Whimsical Wireframes?

88:57 - As the founder, what are your favorite details behind whimsical that maybe an average person doesn't notice?

90:27 - If you would have designed Whimsical again from scratch, what might you change?

91:39 - What do you wish you'd known before you'd started out?

93:10 - 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?

95:06 - Given where you're at, what are the things, when it comes to design that you really care about?

96:36 - What is your vision for Whimsical?

97:31 - What advice would you give to another young designer founder like yourself?

98:47 - Where can people learn more about you and where can they learn more about Whimsical?

In this episode, you'll learn

1:27 - How Steve found himself in drawing classes at college

7:54 - How he approached being rejected for an internship

10:52 - Why Steve did projects for free to gain experience

12:22 - How he used his experience playing sport to overcome rejection

15:06 - The people who've made the most impact at the start of his career

17:33 - How Steve and Kaspars built Whimsical as a tool for themselves

22:24 - How the Co-Founders came together to build Whimsical

32:49 - The secret behind Whimsical's growth

36:41 - How Steve handles user feedback

38:15 - The Whimsical’s path to core users

43:56 - Why the Whimsical team chose to stay self-funded

55:22 - The benefits of remote work

61:36 - Whimsical’s values and how they operationalize them

66:36 - How Whimsical filter and apply feedback

68:41 - Why Steve identifies Whimsical as a maker-driven company

72:33 - How to overcome the challenges of remote work

77:17 - How Whimsical dealt with adding team accounts

89:58 - Why Steve likes Whimsical's upgrade confirmation screen

97:40 - Why skills and integrity matter to collaboration

Also mentioned in this episode

Co-founder Kaspars Dancis

Shape up process

G suite

Slack

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Connect with Steve

Linkedin

Whimsical blog

Twitter

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While there are no one-size-fits all methods that exist, there are several ways for you to boost your startup’s profitability.

In E04 Steve and I discuss what it means to build a profitable software startup and what steps Whimsical took to get where it is today.

A key point that Steve makes, coming from his own experience working on Whimsical, is to work within your means. A startup can choose between staying bootstrapped at the onset or seeking out investments or investors. In Whimsical's case, they decided to stay self-funded and grow revenue slowly over time.

Staying bootstrapped means being able to focus on what matters and honing what skills and assets the company already has before venturing into riskier territory. There is also cultivating that energy within the company, that they are driven more than just by generating profit—which can open up a lot of opportunities later on.

To that end, Steve says:


“I think it kind of opens up all sorts of possibilities of like just dreaming about having the freedom to take these big bets and to be mission first, and to like I guess be led by something higher than producing profits.”


However, Steve cautions, that while it is not impossible to start bootstrapped, it does come with its tradeoffs. These are limitations on what can be expanded within the company at a time. Being bootstrapped means being selective, making careful choices—as a company trying to run within its means, you will not immediately be able to grow your team as much as you may want. You’re also likely limited on the kind of marketing you can do.  

This requires a lot of patience. Juggling more tasks with your current resources because, ultimately, you can’t spread them across a larger team. However, Steve found that being able to focus on their customers and the product helped them a lot in the beginning:


“So if they sound like kind of disadvantages, 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 very focused and so that’s been huge and an amazing way to work, really, really fun.”

A pared-down team also fosters an environment more conducive to asynchronous meetings —meetings that don’t have to take place with everyone present or at the same time. Consequently, it inspires a different type of workplace. One that’s less hectic and less rushed for everyone.  


“And so it’s more I think a style of I’ll go do some work over here, you do some work over there. And then 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.”


That said, this does impact how work is conducted and how the team functions. One other thing that’s necessary though is the flexibility and adaptability to your colleagues’ situations (all of which are typically unique). There are different ways to leverage this in a remote set-up. A common one is to conduct check-ins via Slack or a communication platform of your choice. The process evolves along with the company and the kind of people added to it over time.

Key here, for Whimsical, Steve says is:


“But, honestly, I think it’s kind of just been let’s go with what feels right, something that’s lightweight 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.”


There are some hurdles to overcome when working in a team that is remote 95% of the time. Steve admits though, maintaining connectedness is challenging. Different time-zones means navigating respective overlap times when team members are online. Add to that, just generally not being in-person as often can contribute to a progressive disconnection. To compensate, Steve and his team try to meet up every six months to stay aligned.  

It’s all part of being able to operationalise a vision, Steve also mentions—it’s one of the ways they try to establish who they want to be as a company. Part and parcel of building a brand or a company is making sure that your vision aligns with the business’ practices.


“Maybe that sounds cliché, 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 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 kind of use our profits and put kind of our money where our mouth is, and actually then do some things with it.”


Steve also talks about the product and what goes into its development and the decision-making around it. There is no “secret sauce” to it, he says, it’s mostly instinct and understanding what kind of product the company wants to create vis a vis their customer base’s needs.

There’s the core part to your product. That’s the part you want to make sure that you’re still consistently spotlighting, investing in, and continuing to improve. But then there are also areas where valuable input from your clients or customers can help elevate it. Making sure you marry up those two and find a middle ground is really important ongoing.

In terms of approaches to improvements though, you can say that one or the other is being ‘support driven’ or being ‘design driven’—there are also firms which are ‘engineer driven’; but Steve makes the important distinction that Whimsical is ‘maker driven’.

This means that it’s a combination of being design driven and engineering. How do they achieve this? Have a solid engineering background, but a good design sensibility as well. This ties well into how hiring is important, in a sense that you need to try and bring in people who align with the company’s vision and its values.

More than that though, if you’re trying to kickstart a project and looking for people to head it with you, its also crucial to find a cofounder or cofounders who share the same ideals as you do. At the heart of it, it’s about building a team that works and that can trust each other to make decisions.


“Just people who have the skills but have the integrity, and the grit, and a collaborative spirit that you can riff off of. ... 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.”


Steve emphasises that learning along the way is a part of the process. Building any company from the ground up requires it. Not everything has to be figured out at the beginning. Not everything has to be perfect when you first start.

Really, as cliché and potentially glib as it sounds, you just have to get started.

Hear the full episode

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Mike Rowe: 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, and how you can use their insights to bring your ideas to life.


Today you’ll meet Steve Schoeffel, the cofounder of Whimsical, a workspace where you can visualize your ideas as soon as you have them. Steve’s a designer and a lifelong learner who’s 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 for you 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 and share Steve’s story. So without further delay, I hope you enjoy the behind the scenes process of designing a software startup with Steve of Whimsical.


Hey, Steve, welcome to the show.


Steve Schoeffel: Hey, thanks so much.


Mike Rowe: 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?


Steve Schoeffel: Yeah, I actually came into design rather late, and it was almost accidental. It 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 hadn’t really done much at all around design. And I had a teammate just kind of out of the blue mention he was doing a drawing class to a few of us, and he was like you know, “It might sound silly to some of you guys, but anybody want to join me?” And I think I’d taken like a mandatory class a number of years back, and had generally good memories from that, and so I was like, “Yeah, like I’m down.”


And 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 fields.


Mike Rowe: Got it. Was that like a life drawing class that you attended or was it something else?


Steve Schoeffel: It was really basic. I think it was like an intro just basic, basic drawing. And but it got me hooked, man. I from that point on I just started taking more and more kind of… whatever they were offering. It was like metal welding, and we did 3D modeling, and just like painting. And there was some Photoshop and Illustrator classes sprinkled in, so there was some digital work, but yeah, it was super broad, really fun—photography, film, kind of everything.


Mike Rowe: And from that time, what was the kind of the work, the artistic kind of work that you really started to resonate with? Was there something in particular that you found most exciting?


Steve Schoeffel: 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. I had this semester-long painting that I did like as this like side study. And I had it set up at my apartment with my two roommates at the time, and it started you know, kind of rough, but you just kind of roughen in the background and everything. And I think they literally thought I was out of my mind, but as like the weeks went by, and there’s like more detail filled in and whatnot, they really started to get like into it. And then they would like kind of check in on me and like start watching.


I don’t know, I think I just realized what it was, is that those type of classes and that type of work just spoke to me on a 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. You know, there wasn’t one specific thing that I was after, or trying to achieve, but just kind of experimenting.


Mike Rowe: Got it. And what was the painting of, out of curiosity?


Steve Schoeffel: 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, and it turned out like pretty decent, and I forgot about it for a couple years, and then after I’d gotten 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. It was like, wow, okay. Like 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.


Mike Rowe: Yeah. Wow. I’ve recently caught up with my parents who are now retired who’ve just caravanned down from Bribie Island in Australia all the way to Melbourne. And they brought in the back of their caravan this like A1 sized color pencil sketch that I did back… must’ve been a decade ago. And it was like whoa, like I really explored some obscure artistic stuff back in the day. It’s really quite interesting.


Steve Schoeffel: That’s amazing. 


Mike Rowe: But it’s nice to see that like 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 the lines, like I’m curious given that you had a background in more like a traditional art, film, that kind of stuff, how did you like determine or figure out that you wanted to design software?


Steve Schoeffel: 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, so and I think that was a big moment for me because up until that point I was just kind of going along taking these different classes. And 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 and it brings in some of the photography or some of these visual elements.” And so I think that was part of what turned me onto design and sharpened the focus a little bit and I just kind of took it from there.


Mike Rowe: Yeah. And what were some of those traditional skills that you think really carried across in to software design?


Steve Schoeffel: 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 like 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. And 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, “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 of like how are you supposed to get work if you don’t have a job? And I think a lot of people find themselves in that spot in some point or another.


But 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 they were just, 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.” And 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 to just kind of get my foot in the door.


Mike Rowe: Yeah, and what were those pieces that they were most interested in, do you remember? 


Steve Schoeffel: Well, I honestly think some of the painting stuff. I had kind of done just a couple pieces there and I remember that being one of the things that was of interest.


Mike Rowe: Drop that picture of the barn in there for them? 


Steve Schoeffel: Yeah. Right. 


Mike Rowe: That’s great. And 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 is like 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?


Steve Schoeffel: Yeah.


Mike Rowe: It seems like a bit of a catch-22 for a lot of people.


Steve Schoeffel: 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. 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 I was like, “Okay, well, you know, I gotta figure this out.” 


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. And so I just 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 it wasn’t needing to like provide for myself like fully. But, yeah, I think that was definitely one of the notable early challenges with getting started was being denied for an internship, having to figure it out, and I reapplied to the same internship cause 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.


Mike Rowe: 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 there some kind of like mental thing that you had to overcome? Cause it sounds like you were pretty dogged. Like you juts came back and you kept trying to like tackle that again and again, and I’m curious like how you felt at the time and what you were thinking about.


Steve Schoeffel: Yeah. I think that I mean, I remember the emotion, 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 and this felt perfect or it seemed to line up,” and then it’s like no. Okay, like, I need to…


Mike Rowe: Denied.


Steve Schoeffel: Yes. And like closed 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 it was like, Well, what do you do when you get knocked down and when you lose a game. You know, you don’t pack it in, you just kind of get back out there and practice your skills and you, you know, kind of jump back in the ring. So I think that was, yeah, that was essentially it for me. It was kind of realizing, hey, this was a low moment, but you gotta keep kind of pushing.


Mike Rowe: Mm, yeah, it sounds like you mentioned that you played lacrosse, right?


Steve Schoeffel: Yeah, lacrosse.


Mike Rowe: At Duke was it, yeah. So like 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 often.


Steve Schoeffel: Yeah. Yeah. No, it’s a fairly regular thing in the game. It’s a pretty physical game, and yeah, and that’s kind of like part of my lacrosse story too is that I came from an area that wasn’t like a hot bed. It wasn’t, you know, there weren’t 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 our guy. Or you know, you’re undersized to play, we’re looking for, you know, bigger players,” and whatever it was. And 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 kind of that was all I needed to kind of get in and start doing work.


Mike Rowe: And 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.


Steve Schoeffel: Mm. 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, I did not have a ton of skills. I had maybe some reliability and a kind of an 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 Viget, 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 tried to dig in deep, and read some books, read some blogs, and kind of deepen my understanding. But I thought that 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.


Mike Rowe: Mm, 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?


Steve Schoeffel: 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.


Mike Rowe: 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?


Steve Schoeffel: 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 so it’s humbling in a way, right? Those guys have—and girls—they just have 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 is like you’ve put something out there, and it’s juts a couple people making it, but then so many people get to experience it. And so many people have these different experiences, and in 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.


Mike Rowe: 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?


Steve Schoeffel: Yeah, so with Whimsical, Whimsical’s 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. 


And some of those were digital, but like there was a time where we’re using this physical white board with a bunch of sticky notes that like kept falling off and 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 so I think that 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 Kaspars kind of peeled off and started working on Whimsical for about six months by himself solo. And so a lot of the initial directional insights 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.


Mike Rowe: 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?


Steve Schoeffel: 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, but you can do with them online. And I’d 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 more visual type of work, and doing the types of things you would do on a whiteboard instead of just text docs and spreadsheets like you do in G Suite.


Mike Rowe: Yeah, great. It’s actually it’s funny, we’ve had this conversation a couple of times, but everyone that I know that uses Whimsical can’t help but 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 it, you mentioned that Kaspars also worked on the idea for about six months. And I’d really like to dig into how you took it form that early idea where it was just like maybe two guys in a room to an actually fully fledged software startup. Can you walk us through what that looked like?


Steve Schoeffel: Sure. Yeah. Well, first off, I have to give a ton of credit to Kaspars. 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 MBP was pretty well under way by the time I got started. And I think what it was at that point was let’s build the core flow chart experience. That was our first product.


And so just focused on some of the main activities that would need to be there for the flow chart creation process. And, you know, there was still a decent amount of stuff that needed to happen. When I came on, we reskinned the whole app, we kind of 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. But it was just kind of mad dash, and there was no actual deadline, but we launched about a month and a half after I joined him, so it was pretty quick.


Mike Rowe: Wow. Out of curiosity, how did the two of you meet and decide that this was an idea that you wanted to do together?


Steve Schoeffel: Right. So Kaspars actually was one of the people who interviewed me for the company that were worked together at.


Mike Rowe: Oh, no way.


Steve Schoeffel: Yeah, so we not knowing each other at all, we had a great conversation in that interview. I still remember it just kind of talking about products and what we thought went into good products. And I think through the course of working together for a couple years, we weren’t working closely together, but just observing each other and kind of crossing paths every now and then. I think I developed a kind of admiration for his skills, and also how he carried himself, and just his integrity.


And so then I think kind of moving that forward when he decided to kind of step aside from FullContact, where we were, and start working on Whimsical. We kind of kept in touch a little bit, and had a few lunches over the course of a couple months, and then there came a point where… 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. Like 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, “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 lunch conversation we went back, talked to our wives, and did some you know, some soul searching for the next couple weeks. But that was kind of the genesis, and from there kind of some other big pieces fell in place, and we were off and running.


Mike Rowe: Wow, that’s really cool. You mentioned you were gonna 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? Like it sounds like you were in this stage of life where you both have wives, you’ve got families, you know 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?


Steve Schoeffel: Sure. First of all, I think I never really considered as a side project. It was, from the start, it was always an all-in, you know, type of thing. And Kaspars had already gone all-in on it, and had been going 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 the and right product to make a go of it.


Because I think the common wisdom, right, is that if you’re gonna build a company of kind of significance, then it’s gonna 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 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 Kaspars. I felt like he would be a great partner, and I thought that we had a good… just we were able to collaborate well together, and I thought that was gonna be 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 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 then also it felt like this was starting a company and being part of an early stage startup was something I was being called to do. That like 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 full… the jump that I was 100% sure that it was the right call. And was so relieved and just loving it, and had kind of sustained that just kind of in one of those amazing opportunities that has kind of been the most fun the most fulfilling work experiences that I’ve ever had.


Mike Rowe: Out of curiosity, you mentioned you had a lot of confidence in Kaspars, your partner, and I’m wondering if maybe the confidence that 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 were 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?


Steve Schoeffel: Yeah, I think that is a pretty good way of putting it. Because that’s funny to admit it right now, but I didn’t see the complete vision for Whimsical as a product early on. I was a little concerned actually. I was like, “Okay, flow charts,” like 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 it seems like, okay, you know you can build a good sized business here. And but there was some concern there, like you know, am I interested enough in this particular thing and is it a big enough market? But 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 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 gonna 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 gonna put our heads down and try to make something cool that we’re really proud of.


Mike Rowe: And kind of figure it out together.


Steve Schoeffel: Yeah. Exactly.


Mike Rowe: 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. Cause I can imagine it’s pretty difficult to do the simultaneously.


Steve Schoeffel: 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 Kaspars’s basement at the time, and you know, we just kind of go walk around the neighborhood and just talk about ideas or where things could go. And kind of… just… imagine what, you know, 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, “Well yeah, that’s generally where we’re going, and let’s start going there.” For instance, when we first launched flow charts, we had wireframes, sticky notes, and mind maps kind of teased up at 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.


Mike Rowe: So given the beginning where you started, you had this vision, you knew you were going to start with flow charts 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 to allow you guys to actually progress forward from there?


Steve Schoeffel: Yeah. I think there’s probably not a real secret. But 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 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.


And that’s totally been our experience is… get that first thing right and some other things will fall in line. 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 the cycle. And so that’s probably been one of the single biggest, you know, contributors to growth.


Mike Rowe: Mm, 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 flow charts. And I remember one day very early on, one of our product managers I think found the tool, and started wire framing or flow charting 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 then suddenly like it carved out the need to like spend an hour on a flow chart to about ten 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.”


Steve Schoeffel: That’s awesome.


Mike Rowe: And I just I remember thinking that at the very start, you’d just done something so right in that you’ve 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, and 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 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 to in like six months later and suddenly no one’s using Lucidchart, we’ve got a Whimsical account, and like yeah, your growth engine worked.


Steve Schoeffel: 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 kind of what we had in mind and these are the things that we did in order to make it that way. 


And so it’s really awesome to hear people kind of use the product and experience some of those things and have them 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.” That was pretty fun.


Mike Rowe: How is it for you? Like how does that make you feel when you hear feedback like that coming from an engineer about the product?


Steve Schoeffel: Oh, it’s really cool. I honestly think that getting good feedback where people are just loving the tool and are excited about it is one of the coolest feelings just hands down of the whole deal. Watching people, yeah, get in touch with us and say some of those things feels amazing. Watching people upgrade and actually like pay for the tool is sort of surreal too still just like kind of blows my mind, but it’s a really cool thing.


Mike Rowe: Mm-hmm. And outside of that growth engine that you mentioned that’s baked into Whimsical, were there any other ways in the beginning where you were perhaps doing guerilla 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?


Steve Schoeffel: Right. One of the really helpful things is that we did a couple 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 jumpstarting 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 Side Bar, 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, you know, troll Twitter and talk to anyone who will, you know, is looking for what we have, and but those were some of the big things.


Mike Rowe: Mm. And what were some of the early challenges in that stage where you were perhaps trying to grow? Like what was it like to really build Whimsical in those early days?


Steve Schoeffel: I think a couple of challenges come to mind. One was just that SAS in general, like a subscription tool is a really slow ramp. You know, each person is only paying you, you know, $10 a pop. And while that’s great, it’s gonna take like 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, you know, people were finding the app and signing up and some of them upgrading that, you know, you had plenty of energy to just keep going and pushing.


But 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, so the collaboration features were not there, just a lot of the stuff around the periphery was just we had that kind of basic flow charting experience, and luckily that carried it enough. 


And with each new launch that we 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 to 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 and the more value that we’re giving the users I think that’s become an easier conversion, which is really cool to see.


Mike Rowe: Mm, and what is it a strategic choice to start with flow charts and not with, say, mind maps or wireframes? Like why did you zone in the beginning on flow charts? Like what was it about it that you really thought would be the best place to start?


Steve Schoeffel: Yeah, you know, you’d have to ask Kaspars. 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 teased up top 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, it was like one year old at the time, and I was up a lot during the night in the middle of the night just holding him and hanging out. And it was this 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 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 wire framing 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, you know, come to real life.


Mike Rowe: Mm. 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. Cause you mentioned that, you know, you were applying at one of these accelerator programs. Why did you make that call to stay bootstrapped? And for context for the audience, bootstrapping meaning staying self-funded, and kind of growing slowly over time with revenue based on profits from the business.


Steve Schoeffel: Mm-hmm. Yeah, and when the topic first came up, it wasn’t 100% clear what path we should take. And we did apply to like Y Combinator and Techstars, 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. And I think that was probably the best thing that could have happened to us, and then it became this decision of, “Well, like, what are the real reasons to raise money? Like what are we gonna be missing out on if we don’t and what are we gonna 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 gonna be around for decades like let’s just keep this going. And so I think there is a lot of influence in the venture capitalist space of this kind of all or nothing, go big or go home, you know maybe you get acquired or something else like this happens but then your product’s kind of going away.


And we didn’t want that, we wanted to give ourselves the best chance possible that we would 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’s hard to say, and we had just maybe not even launched the product when we were having some of these conversations, but and just realizing that some businesses don’t have that opportunity, and like but it felt achievable for us. And I think in hindsight, it’s been one of the top, you know, 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 this 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. And especially now that we’re profitable, I think it kind of opens up all sorts of possibilities of like just dreaming about having the freedom to take these big bets and to be mission first, and to like I guess be led by something higher than producing profits.


Like sure, you know, we want to kind of continue to grow and produce profits, but it’s like, “Man, what could we do?” And so I think some of these conversations have been incredibly fun and just dreaming about where the company can go and what’s possible because we are self-funded and independent.


Mike Rowe: Mm. You mentioned being profitable and I’m curious how that feels given that you were denied from the accelerator programs to actually go out on your own and build like a functional profitable business.


Steve Schoeffel: Yeah. Yeah, you know, it was kind of one of those things where with the SAS model of just kind of chipping away, you know, and you kind of each bunt you get a little 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 break even 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 that’s there, and it should stay that way, and let’s go figure out like the next cool stuff that we can do.


Mike Rowe: Mm. 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 tradeoffs you have to consider given that you’ve got no outside injection of capital?


Steve Schoeffel: Yeah, I think tradeoffs 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 and 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 disadvantages, 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 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. So amazing in that regard.


And 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, like let’s take a look back and evaluate like what do we want to do? Like where we do we want to spend our time?” We don’t need to, you know, hit certain numbers for the business necessarily. Like let’s really think hard about what we want to do next and have fun with it.


Mike Rowe: Mm-hmm. 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 I find to be quite remarkable like you talk about, you know, building a business that’s at least going to last ten years, you’re talking about long term thinking, you’re talking about putting users first. 


And from my understanding, a lot of startups in this space when they have 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 like to design that business? What are the things that you’re thinking about and what’s the context you carry on?


Steve Schoeffel: 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? Like let’s see if we can get as close as we can to that. 


And so some of those things have informed like 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 hug fans of just a remote, calm, asynchronous minimum amount of meetings. Just and in partially by the fact that we’re just six people right now, but there’s just not like a lot of extra, you know, BS. There’s not the 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 and if we continue to grow in terms of headcount. But 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. And you know, we have a big time zone difference between a number of our teammates are in Latvia, and then a couple of us are in like Colorado and 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 like a few one-on-ones.


Mike Rowe: And for anyone that’s not familiar with the term, how would you describe asynch meetings or asynch to them?


Steve Schoeffel: 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, we strive to try to do a lot of our work just based on, 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 do some work over there. And then 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.


Mike Rowe: Mm, that sounds like you’re baking calm into work whereas I can imagine a lot of  workplaces bake chaos into work.


Steve Schoeffel: Yeah. Yeah. And again, like it is simpler, right with the smaller number of folks. But I know that there’s larger companies that are working this way as well, and so we have to keep kind o those same things alive, and you know, maybe have to tweak some of the processes along the way. But it’s been a really liberating way of working, I love it, and it’s just yeah, like I said, just very calm and you kind of take it at your own pace and a lot of time for deep work and focus.


Mike Rowe: 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?


Steve Schoeffel: Well, I mean everybody’s situation’s 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 cause, 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. And 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. And, yeah, just kind of being very involved with my kids, and my wife. And so that in and of itself has just been this like huge, tremendous blessing that I’ve been really, really thankful for.


And 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 for, you know, a week here, a week there, or maybe a little bit longer stretches. Which is really fun and just almost feels like it’s like rigging the system, like this shouldn’t be fair, like this is, you know, not real that you could just sort of pick and go somewhere. And but that’s been it, and you know, I think I enjoy kind of like the home office thing, and still getting out for some like coffees or lunches with friends or whatever it is. But yeah, there’s just so much possibility when you have that much flexibility.


Mike Rowe: Mm, 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 in 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.


Steve Schoeffel: 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 a 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, you know, so-called founders, the first people in. And so I think that is another like really cool part of kind of coming up with some of the larger structures of the business and how that can work.


Mike Rowe: Mm, 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. Like how do you, I guess create that for a remote company from the ground up?


Steve Schoeffel: Even in our short kind of couple years of existence, the company’s changed a lot. Like when it was just two of us in a basement, and then when we added Mikey, the third guy, then we were kind of in remote mode. And Kaspars kind of moved up to Boulder from Denver, and so then we were in remote mode. And we’ve kind of needed to rethink some of the processes there and some of the communication patterns. 


But, honestly, I think it’s kind of just been let’s go with what feels right, something that’s lightweight 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, 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.


And, you know, we were just talking this past week or two about what like 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, “Shape Up”, 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 seems to be lacking or what’s going well and doing more of that.


Mike Rowe: 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.


Steve Schoeffel: Yes, definitely.


Mike Rowe: 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?


Steve Schoeffel: Sure. Yeah. And I think in some ways we’re still establishing who we want to be. And, you know, we each kind of come into the company with our own values and what we care about. But I think, you know, 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.


And, yeah, like I was saying like with just six of us, we could still have conversations around like one dinner table. So when we get together, you know, every six months or so for like a summit, 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 do plant a bunch of trees and offset our carbon footprint.


Mike Rowe: That’s really cool.


Steve Schoeffel: And yeah, it was just kind of one of those things that one of the guys on the team came up with the idea, and just championed it, and felt passionate about it, and everybody was on board. And 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 make the world a better place.


Maybe that sounds cliché, 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 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 kind of use our profits and put kind of our money where our mouth is, and actually then 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.


Mike Rowe: Yeah. Fantastic. And speaking of 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?


Steve Schoeffel: Yeah. We’ve been building for ourselves, right, primarily. Especially in this first, you know, year and a half to two years kind of said like, “Let’s build the mind mapping tool that we want to use. And 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 hearing their ideas and their feature requests. And I think just kind of 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 makes sense at what time.


I think that’s roughly how it’s been going and Kaspars and I, I think, will just kind of keep throwing ideas back and forth on what could be cool. And, honestly, Kaspars has a really good mind for… and I picked out 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… you know, timing for the different things we work on.


Mike Rowe: Mm. And you mentioned like you were 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 like ideas for where the product should go or what features you should release.


Steve Schoeffel: Right. Honestly, I think that it’s not a sophisticated system. It’s more just 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.” And, 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 just kind of filter some of these inputs into a couple like tangible—we could go and build this, we could do that, we could do that—and keeping it fairly informal.


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


Mike Rowe: Mm, and thinking about that a little bit more. Like some companies say that they’re design driven, some say that they’re support driven, some say that they are, you know, engineer driven. Like how would you describe what drives Whimsical at its core?


Steve Schoeffel: Yeah. I’ve thought about this some too, and I think that what Kaspars 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 a just of 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, I was telling Kaspars 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 having that is the goal. Like let’s set the sights 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 hokey, but maybe it’s like a craftsman led company. Like we just like craftsmanship as like a super important ideal. 


Mike Rowe: Mm. 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 of what you’re saying is there’s this bigger push to be better at Whimsical. 


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 Kaspars and what you take on for Whimsical to constantly push for more and push for better.


Steve Schoeffel: Yeah, thanks. I think that is at the core of what we both like enjoy and value. And I know that it’s really fun for me to have someone like Kaspars 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.”


Mike Rowe: Given that you’re a fully remote team then, what are some of the challenges that show up with remote work itself? Cause, you know, you can’t just with Kaspars being in Boulder, you being in Denver, you can’t just you know, open the door and you know, Kaspars’ right there in the next room. What are some of the challenges and how do you kind of overcome those challenges while working remotely?


Steve Schoeffel: Mm-hmm. 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 is just feels fundamentally different. I mean you’re just kind of sharing a meal with someone and you’re, you know, some of those kind of small talk things. 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 of that like real-time chatting and you know, Zoom call or whatever it is.


So those feel like the big ones to me. And you know, we kind of do those every six months do a summit where we’re in person. That’s roughly the cadence that we were doing at this point at least. And you know one of the other common ones, it hasn’t been a huge factor for me just cause, but loneliness I think is something that’s come up. And yeah, I’ve got like kids screaming in the background at least now with my home office setup. And you know, just like a lot going on it feels like, but no, I think that can be for sure. 


And like I think there is a general communication challenge with remote work, and 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 kind of improving that for ourselves.


Mike Rowe: And are there any challenges around keeping everyone aligned in support of the vision while you work remotely?


Steve Schoeffel: Yeah, you know, I think that that, like many of the other things, has been an 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 his maybe not like an opportunity that a lot of people have, but it’s really helpful for us.


Mike Rowe: Just on that, like how does Whimsical use Whimsical, out of curiosity?


Steve Schoeffel: Right? Yeah, like I remember seeing like a Figma designer saying like, “People ask me if it’s weird designing Figma in Figma.” And that they had like two windows 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 Hill Charts from Basecamp if you’ve seen those. But basically you’re just kind of tracking 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 mind maps, and I mean you know, just kind of using the basic tools. We just had an integration go live with Notion in the last week or two, and we use 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 cause I think between Figma and Notion and Whimsical, that’s kind of like where we spend the vast majority of our time. But so, yeah, it’s nice and it’s been cool kind of bouncing between those and seeing them come together in a little way.


Mike Rowe: 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?


Steve Schoeffel: Right. Sure. Well, first, I would say that it’s like sneaky complicated, or maybe it’s obviously complicated, I’m not sure. But 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 or kind of primitives for sharing. That’s some tricky stuff. We were just talking about that today, honestly, just like it’s like a continual refinement process. And, you know, getting the basics in. 


I think Kaspars had been kind of mulling on that for a while, and 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, like a couple months. Like, you know, it’s pretty involved.” I mean he’s like, “I don’t know fully, but I think it’s pretty involved.” And we’re like, “Oh man, okay. Yeah. Well I don’t know when we’ll get to that.” And then he’ll be like, “Well, I figured some things out, and it 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, feature there and gradually getting to the place where you’re solving most of the needs. I think like there’s still like it’s still simplistic in some regards with the team collaboration. So there’s probably like some improvements that will need to come there in the coming months. But, yeah, just kind of responding to any like pressing needs and then trying to refine it as we go.


Mike Rowe: Mm, for sure. You’ve mentioned the book “Shape Up” quite a few times, and for those who 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 like could you talk a little bit about how you use the concepts in that book and apply that at Whimsical?


Steve Schoeffel: Right. We’ve kind of we all read it, and one of… Giannis actually, one of our back end engineers did a huge mind map of it, which was cool inside Whimsical.


Mike Rowe: One way to use Whimsical, right?


Steve Schoeffel: There you go. Yeah. It was pretty big.


Mike Rowe: Is that public, out of curiosity, I would love to see that.


Steve Schoeffel: Um… It could be. I can definitely send you the link because I don’t know that we actually like tweeted it out, but we were kind of like, “Should we? Like this is kind of cool.” So I’ll send it to you.


But I think we’ve read “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 the ones doing the shaping are usually like the product people, the product designer, you know, the product strategy person.


They have like separate shaping people and implementing people, whereas it’s just like 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, and 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 gonna design it, so you know, I’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. 


And, yeah, after we kind of… you kind of have some rabbit holes, and no-gos, but then we’ll have a period of time we’re collecting some of those big ideas in our board, and then we’ll start to piece those together in terms of what do we think we can get done in the cycle, and what would be like a stretch. So that’s maybe slightly different as well, but yeah, we’ll basically kind of say, “Okay, like you know, you can take this feature, you can take this, and if we can get to it, we’ll do this and that.” 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.


Mike Rowe: Perfect. I wanted to shift gears again now. So I have reached out to a whole bunch of designers in my network and like asked 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?


Steve Schoeffel: Mm. Right. Contextual toolbars are fun. And I’ve honestly really come to love them and there are some constraints with contextual toolbars just cause you only have a limited amount of space that you can really go before it starts to get out of control. But 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.


So it just 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, and just strip away some of that. And also just I think it reduces just kind of some of the cognitive overhead of being like, “Okay, I need to like crop this image. Where is that crop icon,” and, 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 image.” So I just love how tailored it is and how it’s expanded. 


When we just did flow charts, like there was a number of core objects. But then when we did wireframes there’s, you know, a couple dozen more. They each had their own, you know, slightly different contextual toolbar. And it’s a cool like surprisingly scalable structure that has, yeah, I think it’s been really fun to work on that.


Mike Rowe: Mm, it’s almost something that’s like flexible but easily replicatable, and then 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 flow charts, to wireframes, to sticky notes, like it’s all kind of consistent throughout the experience. That’s great.


Steve Schoeffel: Yeah. It’s surprisingly flexible like that, then it can cover like a pretty wide range of things. And for me, too, like just doing the design it’s actually pretty fun working on the icons. And just kind of, 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.


Mike Rowe: Fantastic. It’s almost like I imagine your drawing class like kind of coming back in a way like getting down into those kind of details.


Steve Schoeffel: Yeah. Yeah, it’s fun.


Mike Rowe: So another question was why did you decide to limit the color palette?


Steve Schoeffel: Yeah. The colors had 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 or kind of success color. So that for us is like sort of like a blue, green, red—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 freeing and actually make people quicker when they’re not having to deliberate between, you know, ten shades of green. They can just pick the one green option and be on their way.


Mike Rowe: Yeah, reduces their decision making fatigue about like the right color of that shade of green.


Steve Schoeffel: Yeah. Totally.


Mike Rowe: Why did you optimize left-handed shortcuts in Whimsical wireframes?


Steve Schoeffel: Right, so we did that primarily for speed. And it was kind of a fun realization while we were building it is like, okay, you have your right hand on the mouse, most people being right-handed. And 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 it was like, “I think this could be a way to make it faster and easier to use.” And so we, you know, mapped them to the left hand a lot.


And I think another thing that enabled us was 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 flow chart mode or wireframe mode. And one of the things that let us do was have more tailored keyboard shortcuts, which was important for that.


Mike Rowe: Fantastic. And as the founder, what are your favorite details behind Whimsical that maybe an average person doesn’t notice?


Steve Schoeffel: That’s a fun question. A couple 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’d entered for the button, and we prepopulate 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 just like, oh, kind of works. But then when you’re like, “Wait, what just happened?” It feels sort of like magic. So that’s a really fun one for me.


Mike Rowe: That’s a cute design. That’s really cute.


Steve Schoeffel: 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.


Mike Rowe: You’re like celebrating that upgrade moment.


Steve Schoeffel: Yeah. Yeah. Right.


Mike Rowe: That’s really cool. If you were to design Whimsical again from scratch, what might you change?


Steve Schoeffel: Honestly, the first thing that comes to mind for me is something we ironically have not completely fixed, but it’s 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 like sort of confusing how that works, and we’ve had like so many people reach out about it, and it’s been something that we’ve meant to improve and make more intuitive. But you can kind of find some of those rough edges and people just like pound you on it. It’s like people are like…


Mike Rowe: Just unrelenting.


Steve Schoeffel: Yes, unrelenting, day after day after day.


Mike Rowe: They don’t notice the button but they just all they care about is that.


Steve Schoeffel: Yeah, yeah, totally. So that I think we would have thought a little bit harder about getting it right the first time. But I think, thankfully, a lot of the major decisions we made probably stick with and been pretty happy with.


Mike Rowe: And a final question from the other designers in my network. What do you wish you’d had known before you’d started out?


Steve Schoeffel: Mm. Well, I definitely listen to a fair number of podcast and read a decent number of books about starting up, and you know, mentioned the Paul Graham essays, which are extremely helpful. And so I don’t think there’s a huge number of like 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, and 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. It’s been so awesome and so I’m just glad that it was like made the jump and just kind of go and do it, and so that’s, yeah, I think you just go and you make it happen.


Mike Rowe: And figure it out along the way.


Steve Schoeffel: Absolutely.


Mike Rowe: 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, like how do you really keep that as the thing that drives the business forward? 


Steve Schoeffel: I think that, you know, 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 who’s an 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 amazing, it was incredible that the timing actually worked out, and everything went through.


But so I do think hiring is a big part of kind of continuing the vision, and bringing the right people that like share the same interests and values and want to do some of the same cool things. And, honestly, something as simple as just having a weekly lunch with Kaspars 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? So that those moments are cool.


Kaspars is moving to Latvia soon, so those will be a little bit harder and a little, you know, farther in between. But yeah, I think I point to those lunches as being a big part of keeping the vision alive.


Mike Rowe: 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?


Steve Schoeffel: 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, like go and do things, and design them, and build them, and collaborate on them.” So kind of empowering other people to use the tools that we’re building is like a really cool part of design right now for me.


Mike Rowe: And we haven’t really covered it up until this moment, but what is your vision for Whimsical?


Steve Schoeffel: Well, I probably alluded to it, because I think when I think about my vision for Whimsical 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, but create that tool that people love and a company that is here for years and years, and like a sort of a generational company. And everything within that like craftsmanship mindset, if we can do those things, like or even just aspire toward them then I’ll be like really proud and happy.


Mike Rowe: Mm. Great. And just kind of wrapping up, what advice would you give to another young designer founder like yourself?


Steve Schoeffel: I think the biggest thing I would say is to find a really solid cofounder or cofounders. Just 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 so I think finding that right person is the first big step and really kind of the important one that carries you through. 


Mike Rowe: Mm. So like really creating a team.


Steve Schoeffel: Yes. Absolutely. Yeah.


Mike Rowe: And finally, where can people learn more about you and where can they learn more about Whimsical?


Steve Schoeffel: Yeah, I think Twitter and our blog are great ways to stay up with Whimsical.


Mike Rowe: I can definitely verify the blog’s got some great stories about like 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 like building product, building companies.


Steve Schoeffel: 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.


Mike Rowe: Good. 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.


Steve Schoeffel: Yeah. Thank you, Mike. Loved it.


Mike Rowe: 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, “Shape Up’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 “Shape Up” 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/shapeup. That link again is whimsical.com/shapeup. The mind map is a really great entry point into the concepts of shaping, embedding, 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 liked 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. Until next time, this is Mike signing off.



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