My guest today is Dan Mall who is the founder of SuperFriendly In this episode, we discuss the following: - Dan Mall Bio - Why do freelance design compared to work in house as a designer at FAANG? - Dealing with red tape, politics while working as a designer - Starting the design agency SuperFriendly - Turning SuperFriendly into a design collective - How to run a network based business - Who's a good fit for running a network based business - Raise venture capital or not - Benefits of trying different things - Winding down the SuperFriendly Collective despite generating millions of dollars in revenue - Choosing to focus on impact over scale - Coaching design teams on design systems - Feeling fulfilled with creative work - Do you have to sacrifice money when choosing impact over scale - Advice for designers who are worried about choosing between scale and impact with side projects - How to contact Dan Mall For show notes, guest bio, and more, please visit: www.designmba.show
Dan has been a creative director, designer, and developer since 1998. He has taught design systems and collaboration at public conferences, private client engagements, as higher education instruction, and on many podcasts and videos. Dan’s superpower is getting people excited, even when there’s challenging work ahead. Dan met his wife Emily when they were both in 5th grade. Together, they raise daughters Siddalee and Charlotte, yorkshire terrier Max, and mini sheepadoodle Matilda just outside Philadelphia, PA.
IS YOUR TEAM LOOKING FOR DESIGN SYTEMS COACHING?
Hire SuperFriendly and experience digital transformation through design systems coaching and practice - https://superfriendly.com/
CONNECT WITH DAN MALL
CONNECT WITH ME
Namaste and welcome. I am Jayneil Dalal and you are listening to the design MBA which is a real-life MBA program for designers. You will learn how to launch a side hustle and level up your design careers from the interviews rock star designers.
Jayneil Dalal: Dan's Superpower is getting people excited even when there's challenging work ahead.
Dan, super excited to have you on the show.
Dan Mall: Jayneil, thank you for having me. I’m excited to be here.
Jayneil: You know, I got to tell you that hairstyle you have, that's a similar hairstyle I had a while back but now this is kind of the shortened hairstyle but I used to love my curly hair.
Dan: Yeah, it's just it's a lot of work. So, every day I’m like “I think I’m going to cut it” but I’ve been going for three years now. So, we'll see.
Jayneil: Oh my god! You haven't? Oh my god! I wonder if your friends have a pool going on like “What is the month he's finally going to cut it?”
Dan: Yeah, I don't know. We'll see. Yeah, it's going to happen inevitably, probably in a summer sometime. Probably I’m going to be like “It's just too hot. I want to shave it all off or just go short again.”
Jayneil: Wow! Now, you started from a very early part of your career freelancing for clients and just started right off the bat designing. I guess, one question I’m curious about is why did you prefer to freelance rather than just joining a big company or let's say becoming a designer at Facebook or Google or something that?
Dan: I mean, I did my interviews at those places, you know.
Jayneil: Oh wow!
Dan: And I’d worked at a bunch of agencies. And at the time, I was always freelancing as well. So, I had full-time jobs working for agencies. I liked the variety that agencies had and I just liked being challenged. So, I interviewed at a bunch of places, probably mid-2000s, maybe early 2000s and one thing that just wasn't appealing to me was it seemed everybody worked a lot and it seemed like all those startups were making great places so that you never had to leave work. And I’m stereotyping a bit. And that wasn't appealing to me at the time where I was in my life. I think I was newly married at the time, I didn't have kids and I’m like “I want to hang out with my wife. I want to just see my wife and my friends” and it seemed like a lot of people that were there were working a lot and they were making money and now they're super rich and I am not. You know, comparatively, they're all VCs and angel investors and stuff but that was the thing that was important to me at the time was just growing and also having a balanced life if I could.
Jayneil: And something I wanted to touch on that, you mentioned, was as a freelancer or someone just working on short-term projects or on your own accord, you kind of have this freedom where there's less bureaucracy. As long as you get the work done, you're good with the client. So, when you work in a big company, whether you like it or not, to some degree you have to deal with bureaucracy, politics, a lot of this just red tape. So, did that even bother you like “Hey, I just don't want to deal with all that stuff.”
Dan: I think I’ve learned that there's always bureaucracy, there's always politics. And I prefer to think about its structure. There are certain environments that have more structure than others. And sometimes that structure is really useful and other times that structure is not useful. As a freelancer and then as someone who managed freelancers later, one thing that I realized is that some freelancers do want structure and that's what makes a freelance life hard is a lack of structure. You don't know when you're get going to get paid. You don't know where your next meal is going to come from. And so, a lot of freelancers do look for that structure which is why they do things permalancing which is like I’m freelancing but for the same place for a long time, which structurally is not very different than having a full-time job. Tax-wise, it is. IRS wise, it is. So, I to think about that structure. At certain jobs, there are things that have been too structured for me where I don't thrive and in other jobs, there's not enough structure where I don't thrive. So, I think a lot of it for me has been figuring out what kind of structure do I need, what's too much and what's too little.
Jayneil: And then from that point where you are freelancing with so many different clients, what led you to start SuperFriendly? Why not just continue solo just freelancing here and there or, like you said, permalancing with a specific client?
Dan: I had a kid. So, at the time when I started SuperFriendly, my oldest daughter Sidda who's 10 now, she was four months old. My wife and I lived in New York. I worked for an agency at the time and I loved to work in there. I just worked long hours and I just didn't want to be working those hours and I also thought it would be unreasonable to say to my boss ‘Hey, could I just work less and you pay me the same amount?” like “I just will show up 40% of the time that everybody else is.” It's hard to do that. If I were in this position, I would have said “No way. You're bananas.” So, the only way that I felt I could get out of that was to say “Well, look, I’m going to accept that I’ll just make less money and I’ll just work less but I have more time with my wife and with my kid.” And so, that was really what I started SuperFriendly for was to be able to have a little bit more control and, back to the structure point, I could create my own structure. I think there's not a lot of places where you could be a part-time designer that's different than freelancing and that's kind of what I wanted to start was like “What if I was like working part-time as a designer and I got to be home and I got to be with my family and I’m okay to take a pay cut for that.” And what I was lucky to find out was “Hey, I actually don't have to take a pay cut for that. I could actually make a good living but not have to work 60 hours a week, 80 hours a week, I could do it on like 25 hours a week, 35 hours a week and design the kind of life that I wanted and the career that I wanted.” So, it really opened the door and I hadn't considered that before starting my own agency, starting SuperFriendly.
Jayneil: So, you start SuperFriendly thinking that you're going to just be a part-time designer, not take a pay cut. From there, how did the model suddenly involve where SuperFriendly is just bigger than Dan Mall and suddenly now you're … you built this collective of other designers that can come and collaborate together on a project?
Dan: I mean, it's … starting SuperFriendly day one wasn't really day one, right? It was like … at that point, I had worked at a bunch of agencies, I think, for 12 years before that, right? So, I’m not starting in the same way that somebody who graduates school and then starts their own company. I had a lot of experience working for other people and I had all these experiences that I was like “I’m going to take a little bit of that and a little bit of this one, a little bit of that and I’m going to leave this part out and leave that part out.” So, SuperFriendly really was a combination of things that came together under a new name on day one but really it was some ideas that have been gestating in my head for a while. One of those ideas that I had learned when I worked at one of the previous agencies was, I learned that sometimes having the right people in the room that's how you win. It doesn't matter like … I remember going to a pitch with a client and I remember our strategist introducing himself as a former elementary school teacher. And we were pitching Crayola at the time. And I remember our strategist, he was a former elementary school teacher and when he introduced himself that way, he said “Hey, my name is Vic. I’m going to be the strategist on this account if we work together and I used to be an elementary school teacher before I was a strategist.” And the client said “You're an elementary school teacher?” – “Yeah.” – “Well, then you win like you all win the pitch. And that was it, the pitch was over, it was done. And I was … and it dawned on me that “That's how you could win? You could win just by having the right people in the room?” And it just was a new lesson for me. And it made me think and maybe have this hypothesis that “What if I could get the right people in the room? I mean, I don't have enough money to employ all of them full-time but you know what? I know them through my network. I know a lot of the right people through my network over the years. What if I could incentivize them to work on a thing for three months? What if they're freelancing? What if I could convince them that it's worthwhile to do nights and weekends while they're working their full-time job?” And it started to open these experiments that I wanted to do. So, that idea had been … I’ve been working on that idea for a long time and SuperFriendly was one of the first ways that I started to test that idea in the wild with clients.
Jayneil: So, it's almost like a Hollywood style model where every movie has a different cast. You don't see the same movie having the same cast over and over again. So, it's like for every project you get or you've won the bid for, you're trying to find within your network who would be the best fit but I’m trying to figure out what are the challenges with that. Let's say you get a project in that you've won the bid and now you're trying to reach out within your network, who would be the perfect cast for this and there's all this back and forth, figuring out the rate what everybody wants, their availability. Doesn't that take a lot of time? And then the people that gave you the project are like “Dude, when are you going to get started?”
Dan: Yeah. I mean, that would be a problem but I was lucky to learn not to do it that way because the way to run a network-based business is to always be working on the network. So, if you're working on the network, when you get the project, that's the wrong time, you're too late, you're already too late, you're doing it under duress and you're going to make really bad decisions under duress generally. So, what my job generally became at SuperFriendly was just always recruiting. So, I’m always interviewing people. I was always interviewing people long before we had a project to understand what is the project that if that project comes in the door that you would automatically say yes to, what would the price have to be, what would the client have to be, what kind of work would it have to be, what kind of team would it have to be, what are your incentives to do that so that when a project came in the door, I already knew who the people were going to be. And then the other part of that is just the quantity, the size of the network. It's if we only had one PHP developer and that PHP developer was booked, well, now I’m screwed like now I’m actually not actually running a network-based business. I’m just running a model of freelancers which is different. So, a lot of it was the supply has to be way larger than the demand. So, if we have two or three clients that all need PHP developers, we have to have a stable of 10 PHP developers that are able to work on that product. So, a lot of it was routing and recruiting long before projects came about. And it sort of flips the model on its head of project comes in, you supply contractors for that. That's like staff augmentation. That's a different model. That's not Hollywood model. It's what movie do we want to make and then who is the client who will subsidize that movie. It's a different way of thinking about work and that's how we started to do it is starting to subsidize to go like “If we pick five people and put them in a room, what's a great project for them to work on?” and then we go and find that project. So, it allowed us to do a lot more outbound. It allowed us to do a lot more proactive work to say like “If we can identify some work that this team should do, let's go out and pitch it. Let's go tell people that we should do that project with them as opposed to wait for it to come in the door and just get everything and inbound.”
Jayneil: Oh my god! And when I assume that when you get the team in the room like “These are cool people that should work together,” so then you are taking all that legwork of reaching out and doing all the outbound work and getting the project, right?
Dan: Totally. I think, that's the work that the agency should adopt. Otherwise, the freelancers can just do all the work. So, would they pay us? Why would we take a cut on that if we're not doing our share of the work? So, one of the ways that we would think about even paying people was “What proportion of the work is this person doing?” So, for example, if we were to do a $100,000 project, if somebody's going to do 10% of the work, well, they should make $10,000, they should make 10% of the bounty. And so, it made us think about “Well, what portion is SuperFriendly contributing to this work? Well, we’ll do the outbound. We'll do the production, we'll do the billing, we'll do the invoicing, we'll do the team culture but what percentage of the project net is that worth?” So, it made us think that SuperFriendly itself has to bring value to the table as much as each individual SuperFriend does. Otherwise, we're just the middleman and we're just taking money out of their pockets for nothing. For that, we should just take a finder's fee.
Jayneil: And it kind of blew my mind away when you said the words that you essentially are operating a network-based business where you're continuously growing your network, talking to people ahead of time. What did that look like? Were you going through events and conferences, random emailing people, Twitter DMs? How are you growing your network and screening people if they're a good fit or not?
Dan: All of those things. And this is why this is not a business that everyone should run. There are people who are suited to doing this business and there are people who would be awful at running a business like that. And it's not because of the model. It's because, I think, that it worked for me for a time because I doing that stuff anyway. It's my superpower. It's like one of my superpowers is I’ve always been doing that since I started in design. I would go to conferences and I would talk to people about what they're doing and what they're interested in 10 years before SuperFriendly existed. So, I’ve always kept up with people and been interested in what they're doing. I’m inspired by people who do good work. I regularly still to this day just send people random messages on Twitter or through their websites like “Hey, I came across your work today. It's awesome. I hope we get to work together someday. That would be cool” because I appreciate people's craft and what they do. I like seeing people do things well regardless of whether that's design or engineering or basketball. That's why I love sports. You get to see people doing something awesome at the top of their ability. It's incredible. So, that's interesting to me. I’m curious about that. So, I’ve always been doing that. And then with SuperFriendly or shortly before, I started to formalize that and eventually a couple years into SuperFriendly, we built our own tool called Cerebro to track what people are doing, where are they, what do they need in their season of work, do they need cash, do they need inspiration, do they need mentorship, do they need to be a mentor all of those things. It really is a community management job. And that's ultimately why I was like “This is too much. I can't do all of this stuff and I need help.” It really is about cultivating the network. That's where the business model is. That's where the core of the business is. You can't run a network-based business without investing in the network. So, toward the tail end of doing that, we were doing weekly opportunities calls where we would run through our pipeline with anybody who wanted to join and people could raise their hand for projects. We were teaching. We were doing snack and learns every month where people would present on a topic. Again, this goes back to the structure. Freelancers don't often have that structure. So, they look to other places to have that structure. So, we started to think about “What kind of structure can we provide to a network of freelancers without them being full-time?” And it even started going down the path of like “One day, I would have loved to provide health insurance and business insurance for our freelancers.” That seems to be a perk of being a SuperFriend. We never got to that place but I think that's kind of the trail that we were headed down.
Jayneil: And did you ever think that “Oh my god! This could be something phenomenal just to raise money and scale it.” Did you ever think about those things like hiring full-time people to just take care of all that?
Dan: Yeah, all the time. I mean, I have conflicting thoughts daily about raising money and about VC and about all that stuff. I don't know that I had a conclusion about that. One of the things that was important to me though is that, I think, when I take somebody's money, I want to be a good steward of that. And that goes from when clients pay me money, I want to be a good steward of that. We have routinely returned money to clients when we don't think we're doing a good job even if they don't ask for it. And so, the same thing with VC. I feel we live in a world where billion-dollar valuations are common now and I’m just like, I mean, “If I’m going to take a $100,000 from a VC, I got to do a good job with that.” My job is to return that for them. And maybe I’m thinking about it too myopically, I don't know. I haven't ever taken investment or anything that. So, I don't know. And then the other thing which is a little bit ironic is even though I work on design system work and SuperFriendly does design, which is basically all scale work, I actually don't think I’m very good at scaling things. So, that's not my super power. I think that I would need somebody else to do that but I would want to work with someone else who could scale something that was my vision. And I haven't found a good partner in that way for that particular thing. I found good partners in other ways but because I never had a good fit there, it was like “You know, this isn't the right time for that.”
Jayneil: I think this awareness is mind-blowing. How did you get that awareness that “You know what? I’m really good at running the community, nurturing and all these things but trying to scale it to the next level, that's … maybe I’m not the best fit for that.” So, how did you come to that realization without having your ego or anything involved in that?
Dan: I mean, my ego is involved and it gets bruised a lot but I’m a serial trier of things. I like trying lots of things and I think that one of my superpowers by default is that somehow I don't really. succumb to sunk cost fallacy. I’m not tempted by like “Well, I mean, I’ve been doing this for five years. So, I got to keep doing it now.” Sometimes I’m like “I’ve been doing this for five years and it is time for that thing to end. That's okay.” So, I think that I believe that things should end and I believe that other things should start and it's okay. and that's also one of the things that I like about doing digital work is some of it really is disposable and that's the value of it like you could try a thing and you could throw it away if it doesn't work. It gets more serious when it's at the expense of other people. So, I try to be cognizant of that but I’ve tried lots of different things. SuperFriendly is one business that I’ve run that I think has a moderate amount of success. I have other businesses that are not. They have flopped, some completely, some in a way that has burned me big time, so in a way that hasn't. So, I try a lot of stuff. And I think that one of the things I’ve learned by trying a lot of stuff is you could always come back from it. You try a thing, it flops, do another thing. You try a thing, it works. Great. Do another thing anyway. And so, I’ve kind of built up a little bit of a tolerance to that just from trying things and messing up a bunch. And I think the more things you try, even if you mess up a bunch, you still have that many more opportunities to succeed a bunch too but if you only do one thing, well, you either are going to succeed or fail at that and it's one for one or zero for one but if you try 10 things, I just think that the odds increase, the odds are in your favor more and more that way.
Jayneil: It's mind-blowing to me that you openly say that there are some businesses that burned you. And given the fact, I’m assuming, some of the time you're doing these businesses, you probably had kids too. So, that risk tolerance is really commendable just because after a while, people just become risk-averse and the fact that you're still taking all these bets. And one of the bets, I just remember, you told me is you had the Cerebro, kind of a community OS you created, operating system, where keeping track of what everyone's doing and it's mind-blowing because the venture capital firm Seven Seven Six by Alexis O'Hannon has a similar operating system where they give access to all the people that are in the network to figure out who's the best person for the intro. And informally, I have something similar in my Google Keeps where I ask all the people on the show that “Hey, what are your goals? How can I …” It's all in my head primarily but document a little bit there and I was like “Oh my god! The scale at which he’s doing it.”
Dan: Yeah. I mean, the way that I say it is fancier than it is, right? We built an internal tool for this. You know what? It's an airtable. That's what it is. It’s not … we could have blown it out more but we didn’t. We didn't have a need for it at the time. So, it's fine for it to stay as an airtable. And it's manually updated. There's no automation on it. There's no any of that stuff. Eventually, one day we could have gotten to the scale of … We Work built an internal tool to manage all that stuff and it is a very robust tool that has machine learning built into it. We could have gotten to that place but we didn't and we didn't need that. And if we would have built that, that would have been the wrong investment. And then the other thing that kind of comes to mind about it is like yes, I had kids and trying all this business and I want my kids to do that too. I want them to see it's okay if you mess up, it's fine. You're going to. You can't avoid doing that. So, I feel I have to model it for my kids because otherwise, where are they going to learn that. If they don't see it in their own house, then they're going to learn it somewhere else outside without the context and the safety of their parents and people who love them. I want them to see that too. So, I have to go through it myself partially to model it for them.
Jayneil: That is … you are such an amazing parent.
Dan: My kids might disagree.
Jayneil: Maybe years from now when they hear this interview, they'll be like “Oh my god! That's such a super awesome person.”
Dan: I mean they're probably in the background like “Ugh! This guy.”
Jayneil: So, at the peak of SuperFriendly, when I was going through a blog post, I think, the revenue it was making, obviously a significant part of the revenue was also distributed to all the freelancers who are helping out with the projects, but it wasn't millions of dollars. So, by all external accounts, people could be like “Oh my god! Dan is killing it with SuperFriendly.” Why did you decide to wind down the project?
Dan: Well, it's relative right. I am fortunate to run a business that makes millions of dollars. I’ve never done that before. That's amazing. That's cool. I grew up as a kid in north Philly. Millions of dollars was out of our reach until it wasn't. And so, definitely, fortunate to be able to do that but it's relative because other businesses make billions of dollars. So, in that relative scale, it was small potatoes what I’m doing. And then there are also other businesses the other way around where there are some agencies that been around for a long time that are making tens of thousands of dollars and struggling and I’m a big dog in that. So, it's a relative measure. I try not to get too hung up about that because … one of the things that my accountant says to me that I love is, he goes “Dan, revenue is vanity. Profit is sanity.” I like that. It's great. It's centering because it's like one of the things that was assigned to me, we were making more and more revenue but we were less and less profitable. And that is a story a lot of times with funded products where lots and lots of revenue, gigantic valuation like a dumpster fire when it comes to profitability. And it baffles me that the narrative around that is like “Oh no, we're not trying to be a profitable company” and I’m like “What? That doesn't make any sense to me. Why doesn't anybody want to be a profitable company?” I mean, I get it kind of but it just seems a weird post-rationalization world. Anyway, I don't want to soapbox on that but, to me, that was a phase of SuperFriendly. In the same way that people have seasons in their lives where they do new things, I think, companies can have that too. I think that's okay. And I think that was a season for SuperFriendly and part of it was, for better or worse, that I’m done with that version of SuperFriendly. I tried some things that I wanted to try. I learned some things that I wanted to learn. I failed at things that I thought I would succeed at. So, it was a good experiment to me. And so, I’m ready for a new thing. So, I call this SuperFriendly phase three, that was phase two and there was a phase one before that that ended. And sometimes, that is more transparent to people and sometimes that is not but, to me, I’m like “I’ve done that for seven years. Phase two was a seven-year phase and I learned a ton from doing that. All right, time for phase three” because I think that, for me, having a company … all of these things, working on digital products, having a company, they're all ways to learn more things about life and people and companies and business and commerce and all that stuff. And I think I maxed out on what I could learn from that version. So, it felt time to wind that down. And I think that that would have been the case like if we ran out of money, we would have been forced to shut it down. So, I’m glad that we didn't run out of money but I think that just because the thing doesn't run out of money doesn't mean that that's not the right time for it to end.
Jayneil: Could it also be that as one of the sole person in a way nurturing that community, growing the network and doing all these things just became too much for one person to just handle all the time for a long duration?
Dan: Absolutely, absolutely. I want to be clear about the fact that I had help. I had a lot of people helping me. So, I’m the sole owner of SuperFriendly but that doesn't mean I didn't have support both in the business and outside of the business. So, it certainly wasn't a one-person operation. We had a core team of really talented people that were working hard at doing their parts of it. So, absolutely, but, yeah, I was burnt out, for sure. Throw on top of that a global pandemic. I don't even know what portion of that was due to COVID or not but you throw that on top and it was like “I don't want to do anything right now.” So, I can't tell which part of that was being burnt out from the business, being burnt out from what was happening in the world but that was the conglomeration of things that happened that led to that decision, for sure.
Jayneil: And thank god you did not take any outside money because if you had taken outside money, you can't just use the burnout as an excuse. You still got to plow.
Dan: Totally. Yeah, I don't want that pressure. I felt like there was enough pressure already. On other things, I’m fine with that pressure. For SuperFriendly, it didn't seem like the right thing to do. It still doesn't seem the right thing to do for it
Jayneil: And I love in the blog post how you mentioned that … if I may just craft a narrative … is in that second phase of SuperFriendly where millions of dollars in revenue are coming in and it's more of in the scale phase where, obviously, more projects, more bigger brand names. And then you said that in phase three, you're doubling down on the impact rather than just the scale. So, can you talk me through that? What does it mean for you to say that “Hey, I’m going to focus more on impact rather than scale?”
Dan: I had a conversation with a friend, and this is when I’m sort of going through existential crisis about “What do I do in my business?” I call up some friends and say like “Hey, could you give me some advice about this?” So, I called a friend who works at a big, giant world-recognized startup running a big team there, used to run his own small, I think, three or four-person company, and he told me “You know, I miss those days. I’m working at the scale of the world right now and scale isn't all that's cracked up to be.” And he's like “When I was running the last company,” he was like “people would come up to me often at conferences or at events and thank me for “Hey, thank you for making this product because it helped me do this thing in my life,” you know. And he's like “Running this … being at this gigantic company right now,” he's like “I haven't had that in like the five years that I’ve been here.” And I’m “Yeah, I can empathize with that.” For a long time with SuperFriendly, there were things where clients, SuperFriends would say to me or to other people on our team like “That was life-changing for me. It was so …” and I’m hesitant to even say this out loud on a podcast because it feels arrogant but we were doing things that changed people's lives. We were putting them on projects or in situations or scenarios that really stretched them, helped them grow, helped them learn something that is impactful. And what I found was in the last couple of years, that seemed to be happening less. I can't prove that. I don't have like a spreadsheet that says like “This is the quantity before and this is the quantity …”, I don't … so, it's just a feeling but that started to happen less and less and I’m like “So, what are we doing all this for?” because that's what I did it for initially. Well, I mean, initially, I did it to be able to spend time with my family, which I was able to do and am able to do. And then on top of that, once I figured I could do that, “Well, what more could this company do?” Well, it could help people. And it sounds trite and cliché but really that is what it is. And that stopped happening. And so, I wanted to double down on that to go like “How could we do that again?” and I’m happy with the work that we're doing right now because daily that is happening. And it's not always a good thing. It's hard. It's not always an easy thing but daily I get comments from our clients and from our SuperFriends or from our team about just saying like “This is really like stretching me” or “This is really like changing me.” And I think that that is what work should do. For some people work is just a paycheck, which I think is fine, and for some people work is an opportunity to do something else too. And I’m like “We work in front of computers on screens. We do things that are frivolous. We're not doctors …” I have a lot of respect for people who are doing what I think are actual work. I move boxes around on a screen. I write code. So, I have a relative sense of the importance of that work and it's not as important as what other people do. So, if we get the privilege of having a frivolous job like that, shouldn't it be fun, shouldn't it be growing, shouldn't it be … isn't it a privilege to have this job? So, why is it not a privilege then to people? Why are they not treating it like a privilege? Why are we not … as managers and bosses and owners, why aren't we giving that privilege to the people that we employ?” That seems amiss to me. So, as a person who can impact that, I’m like “Well, let me try. Let me try to do that and that” because that wasn't happening a lot as much. I was like “I want to try and figure out another way to get that to happen.”
Jayneil: So, it's almost like in the scale phase of SuperFriendly, you were kind of managing other freelancers, kind of like getting more people to join the collective which could almost mean that sometimes you're kind of away from the pixels like more managing and more outbound stuff but now in phase three, it seems to me you are in more hands-on in the pixel work.
Dan: Absolutely, sort of. So, let me qualify it. In phase two, I was even more removed than what you're saying, which is I wasn't managing our network of freelancers. I wasn't doing sales or outbound or anything that. I was really trying to be a CEO. So, I had somebody who was doing all of our business development. I had somebody who was our … we called her our casting director, the person who would cast people for the movies that we were doing, the projects that we were doing. So, I had an operations person, an accountant, a financial … like all of those things. So, I wasn't doing any of those. I was really trying to see if I could be a CEO, somebody who could influence culture, who could set vision, who could tell people where we're going. And that was hard for me. I’m like “I don't know if I’m good at that.” I might not be. There's a version where I might be but, I don't know, it's still unclear to me. I’m still close enough to that that I’m like “I can't reflect on it appropriately yet. That's too close still.” In phase three, I’m not necessarily designing things. I’m not designing things for clients. I am very hands-on on teaching though. So, all of our new practice in phase three of SuperFriendly is we coach teams on design systems. One of the things that I had learned and realized was every time we make something for a client … because that's the history of SuperFriendly. We would make websites or make apps or make whatever design systems … every time we would do that, at some point, inevitably, the team would throw it away. And I think it's because for a design system specifically, it's got to be rooted in the company, it's got to have deep roots for it to take and for people to use it well. And I think that my hypothesis now is that comes from people there having made it, not having some agency make it and drop it off and train you and “Good luck to you. You know, we're out of here.” So, what we do now is we just coach. And that means we're coaching the team on how to make a thing that we know how to make but we're trying to transfer that knowledge to them. So, we coach on design. We coach on technology. We coach on design ops. We coach on production. We coach on all of those things and really getting the team to understand how to do that intrinsically so that the roots grow deep and that it's harder to pull that out later on and kind of developing those practices with them. So, I’m very hands-on in that. Every day I am coaching, every day I’m teaching, every day I’m workshopping with our clients.
Jayneil: The way that you're speaking about the phase three where you're choosing impact over scale, I can already sense that on your face that excitement, that tingling, that “Oh my god!” like I can already see it right now and here it in your voice.
Dan: I’m fulfilled, for sure. Yeah, I’m fulfilled at work now in a way that I haven't been in the last two years.
Jayneil: Wow! The biggest challenge that I see and I face this myself when I talk to other design entrepreneurs, a lot of us are creatives that really want to just do the work sometimes certain aspects of it and really not all creatives are meant to become the CEO and founder that just scale big businesses. It's just not a good fit for creatives sometimes or many times. And I’m going to tackle elephant in the room that a lot of times that decision is made whether it's because that's what the media is portraying like that's what's supposed to be happening but one of the root causes is definitely money. I mean, at the end of the day, a lot of us are making money for our family, ourselves, whatever the reason might be. And the way it's glorified is that if you go the scale route, you end up making more money. You might sacrifice your personal satisfaction when you choose impact. So, I was going to ask you how do you deal with that conundrum? Is it always that if you choose impact over scale you let go of money or is it like you can have both, have the cake and eat the cake?
Dan: I believe that you can have both. I will say I don't know that I have proof of that though. So, one thing that was really easy in phase two of SuperFriendly is we made a ton of money. We did. In phase three, we make less money. So, I’m more worried about money now with the company than I have been in a long time. I believe that that will even out. I believe that that's because it's a new thing, we're trying it out, we're figuring out the model, we're figuring out what we can charge, what our capacity, all of that stuff. So, I feel that's early. We’re probably six months, seven months into that, maybe a little bit more than that but that's still early for me versus phase two of SuperFriendly with seven years in the making. So, lots of time to figure some stuff out. I believe that it's there and especially because I think that designers are well suited to become executives if they want to. And I think that they have the skill set, perhaps not the personality, perhaps not the superpowers but I think designers specifically are like we're trained to look at a thing and go “I wonder how this could be better.” That's just a default. I talk to so many designers. I had this conversation today with a designer like I can't go to a restaurant without critiquing the menu. I can't go without naming what typeface that is. So many designs are like you can't turn it off. And when you apply that to other things outside of graphic design, that scales well. Designers can look at a city and go like “I think that I can figure out a way that this could be planned better.” Designers could look at government and could look at big systems and say like “I think I have a version, you know, that … this could be better for everybody.” I think that's our job. So, that is the job of a CEO as well. It's the job of a of an executive is to look at something and go “I see how this culture could be better. I’m going to implement those changes. I see the path to it. I have the vision for it.” So, I think that designers are trained in that skill but some people just don't have the temperament for it. And even if they do, some people just don't want the responsibility, which, I think, is fine. You don't have to do it. Again, this is a privileged job. You're not forced to do whatever you want to do. I agree that it sucks, that capitalism is a necessary evil in this, that is the world that we live in and lots of people have different opinions about it, I have my own opinions but I think that there is a version where you can have your cake and eat it too. I also believe another thing that is true at the same time is in the in the words of the immortal Notorious B.I.G. “Mo money mo problems.” So, I believe that that is true also. So, figuring out how all of that works together, I think, is the trick. I haven't figured it out but I think … I believe that there is a way that that's reconciled but I don't have the words to say it yet.
Jayneil: I remember a saying that my mom used to tell me growing up in India. She said that “It's better to cry in a BMW than it is to cry on the street.”
Dan: I love it.
Jayneil: So, there's that mentality where you are driven to make money because you have seen what lack of it can do to you and others around you. So, there's definitely that. I guess, what would your advice be to a creative who's got something going on whether it's a side project, their own practice, freelance, whatever they're doing and they've gotten some traction or success and they're at this crossroads where they're like “I like what I’m doing but there are two paths for me. One is of just absolute scale. The other one is of just focusing on impact.” What would you tell them at this point? What should they do or how should they approach that?
Dan: I mean, I have an unpopular response to that which I’ve talked to some people about this and they don't like the answer but it's you just decide, just decide what you want. At some point, there are some decisions, in my mind, that there's not a right answer and a wrong answer to. And I think that, again, this is a thing that designers are more trained on than others is, sometimes you just make a choice to make a choice. Is impact better than scale? I don't know. Is scale better than impact? I don't know. And it's not even … well, it depends on what you're talking about. Sure, that's an answer too but at some point, you just pick. Could SuperFriendly scale? I believe so but I don't want to for lots of reasons. I’m lazy, it scares me, I don't have the capacity for it right now mentally, another thing is easier, there's another opportunity. Who cares about the reason? At some point, you just pick. And I think designers were trained at that because we have 16 million colors available to us and we have to pick four for a palette, right? We're trained at narrowing down 16 million choices to four. We're good at it. We practice it. And so, I think we're all suited for that but we're not practicing how that scales, right? Designers can pick colors but then you ask them to pick a career path and they're like “I don't know if I want to be a manager or if I want to continue to be an IC” because it's a hard decision. So, we practice applying that same skill that we have in another area. So, I think, my advice for a designer, which is the unpopular thing is like “Well, what do you want?” and maybe just sounding it out, to give a more productive answer, “What do you want to learn?” because, I think, that helps you to go like “Give it a timeframe.” One thing that I learned from my wife, she's so good at this, is she picks things that she wants to learn and she gives them a timeframe. “I want to learn to be better at soccer. I’m going to give this 12 weeks. I’m going to learn to body build and I’m going to give this 16 weeks.” It's so good because at that point, you know when you need to quit, you have an out already. And so, because you already have a built-in out, you can just persist. If you can have the willpower and you can make the choice in advance and go like “I mean, it's only four more weeks. I know where the out is going to be,” that sometimes helps. So, what do you want to learn? Do you want to learn how to scale a thing or do you want to learn how to have more impact? And you can switch like “All right, I’m going to try this for four weeks and then I’m going to switch” and then you might learn “Four weeks isn't enough.” I think that's part of the emergent nature of learning at work.
Jayneil: It's funny you mentioned the built-in out. My built-in out for the podcast is 101 episodes. I’ve already crossed the halfway mark, near to like 60 now. So, yeah, almost halfway through but … I have ADHD. So, I’ve always … with Myers-Briggs, something like an ENTP type A. So, I knew that for my personality, there's just been a whole track record of long abandoned projects. So, this time I was like “You know what? You're going to do this but until 101 episodes, you have to keep going through it but after that, if you choose to walk away, no guilt feeling, nothing. You choose to, you have the right to.”
Dan: It's such a great strategy. I remember reading the book The Dip by Seth Godin and in that book, he talks about ultramarathoners and how they're running 50 miles or 100 miles or whatever. And what a lot of them do is they pick the conditions before the race starts that they'll quit – “If my right knee acts up I’m going to quit, but any other condition other than that, I’m going to keep going” – because when you're at mile 20 and you're like “Oh man, I’m breathing hard,” it’s so easy to go like “Yeah, I should probably tap out at this point” and you would be reasonable to do so but that's why they decide ahead of time, they decide before they're in the situation “All right, if it's my right knee, that's the thing that's going to … because I know that that's going to have some serious impact” or whatever. “That that's just what I want to do. I don't want to push that part. Anything other than that, if my ribs start hurting or my lungs start … I’m going to keep going.” And I think that there's a lot of good practice to going … deciding the conditions to quit before you start a thing so that when you're in the gruel of it, you're like “I can persist. Four more weeks, 50 more episodes, I’m over the hump” and you could see the finish line. And then if you decide to do more episodes from there, great, that's a different choice. If you don't, you can walk away. No guilty feelings.
Jayneil: And I know I’m using the podcast as an example for this because a lot of what you're saying makes so much sense to me because these are decisions I had to go through. A lot of people, when they play a certain game, they don't realize that you can choose what adventure you want to play in the game, you can choose what you want to do. So, it's like yeah, I mean, I’m playing the podcast game and everyone's like “You got to grow a massive following and play the Twitter game” and I’m like “I’m not about that. I mean, I do like talking, connecting with you but the other part I don't like.” And I was like “Oh my god! It's okay. Nobody's there to punish me if I don't want to do that.” And that was a big takeaway for me like you can customize what you want just based on choice and not what is the best practice so to speak.
Dan: That's big. I mean, because we all … we are almost always our own biggest punishers of that stuff, right? We always think it's going to be external but it's often not. It's often us just feeling guilty about a thing because we thought that we should do it. And if we can get away from that should, I think there's a lot of freedom in that.
Jayneil: How can people contact you? How can creatives reach out to you?
Dan: DM me usually on Twitter. That's where I’m the most available. My inbox is flooded and I have messages from weeks ago that I need to respond to. So, if you email me, that won't be a good thing but I’m @DanMall on Twitter. Send me a DM. That's usually a good way to get a quick reply from me.
Jayneil: Awesome. Thank you so much, Dan, for coming on the show and sharing your wisdom.
Dan: Oh, my pleasure. Thank you for having me. Thanks for letting me riff it with you for a while.
If you made it this far, you are what I call a design MBA superfan. And I’ve got a gift for you, my superfan. Head over to designMBA.show where you will find my email address. Email me one thing you learned from this podcast episode and I will get on a 30-minute call with you and help you in your career goals.
See you in the next episode.