00:00 *Matt: * Welcome to Podcast Awesome where we chat about icons, design, tech, business, and nerdery with members of the Font Awesome team. Font Awesome, go make something awesome. Font Awesome, go make something awesome. I'm your host, Matt Johnson. Today I'm chatting with Font Awesome founder Dave Gandy as we discuss the things that you can learn when you fail at business and life. It's not a downer episode, I promise. Dave talks a little bit about flunking out of MIT twice as well as the lessons they learned during the Font Awesome 5 Kickstarter. 

I seem to remember when we were talking about the Kickstarter, there were some things that you mentioned you thought were failures but ended up being a positive but you didn't know it at the time. 

01:08 Dave: The story about the Kickstarter I think is particularly interesting. There was one, we tried like three things that year that all failed and then we thought they were failures anyway. And then it's interesting. Yeah, the story of how that all came about and how that actually greatly impacted the Kickstarter was a good one. There's a weird thing about self-fulfilling prophecies, like things that we believe to be true, how they can actually come about. The world is not this shiny magical place in the way you believe what as a kid where anything you can imagine it can happen. But it is really strange as an adult to see the truth that some of the things that you believe can become true for having believed them.

A startup is nothing more than believing a lie long enough that it becomes the truth, that your company has something that people want and that you can make enough money off of it to survive. That in a way when it starts, that's a lie. It doesn't exist yet. You hope it does. Same is true in a weird way for failure, that if we believe that we have failed, sometimes that's completely accurate. There's a specific thing we were setting out to do. It didn't work. 

And so now the crossroads is, what do I do with that thing that appears to be failure on the surface? And in some ways it absolutely is. In many ways it absolutely is. But what do I do with it now? And there are some failures that we look at and we realize, you know what? It's actually important that I don't do this anymore. This was a bad choice, didn't turn out well. And so we're going to stop doing that. So you actually choose not to continue. That kind of quitting is quite valuable. There are things where you realize, you know what? This is beyond my ability. 

And if you understand the truth of it and you understand your relationship to reality accurately, that might be a really good choice. But the real shocking thing I think is how often we are wrong about that. We make an assessment that we failed and it's because we're not good enough or it's because, I don't know, she just didn't love us or you know, we can come up with any number of reasons why a situation didn't work the way that we really hope. But it's amazing as human beings how often we're wrong about it.

03:17 *Matt: * And that's a real part of the challenge. It's a timing thing, right? It's like it wasn't the right time. It wasn't the right set of skills at this moment, but maybe became something different later on.

03:30 Dave: Absolutely. This happened in tech all the time where there's a great idea for a product and the execution is pretty darn good. It's just that things weren't ready yet. And it might be that the technology wasn't quite there yet, right? Like for, you know, a Palm Pilot. There's a lot of really cool stuff that it was able to do, but it wasn't quite there yet. Battery life was okay, but the feature set wasn't great. It could only do a few things and it didn't do any of them extremely well. It was a great idea. Everything about the business made sense, but technology, the technology world wasn't quite ready for it. And then you see, you know, the point when the iPhone comes out where you've got some phenomenally creative engine individuals figuring out the right set of features to push forward to combine all together and to make that one new thing where the timing was better. But it's interesting how anytime something succeeds, no one says the timing was wrong, that it's only after a failure. Does anyone ever talk about timing? And I think we're often wrong about timing too. Sometimes it was just a bad implementation. Sometimes it was just a bad execution by the people doing it. And that's okay. And that's the kind of failure. If there's a thing that's actually beyond your abilities, that is okay to move on from, right? That's okay to say no to, and to say, you know what, this is not a good choice for me and where to spend my time. But if it turns out that you only failed with lowercase F, right? Not capital F, right? This is beyond you. I can't do this. And it's really important that I move along, but lowercase F that this iteration just didn't work. This thing that we tried just didn't work. 

Well, then there's a different relationship that you can have to what seems like failure. If something doesn't work out and you try again, no one thinks about that and focuses on that as being failure. You just think of that as somebody who is resilient. So you think of somebody who just keeps at it and keeps trying. And I talk a lot about beating your head against a brick wall until finally the brick wall actually falls down. Because that's a real thing too. That's a very real thing too, where you know this is a good choice. You know it's the right thing to be working on, but you just haven't figured it out yet. It takes an emotional fortitude to be able to keep going. So we have to, as individuals, we have to know where our value and purpose as human beings lies. And it's not in the thing that we're doing. It's not in our work that we're doing. 

So if it is, then it gets really complicated. Then it becomes very hard to divorce your feelings about yourself and your feelings about what seems like failure from the failure itself. And so then you get very wrapped up in just trying to protect yourself emotionally from a truth that you may not want to believe. Because it turns out reality is sometimes not very friendly.

06:05 *Matt: * Well I think we're in such an interesting time too. I mean around the time that we grew up there was sort of a positive thinking kind of mantra. And there's actually really interesting studies about that. And how that kind of shook out over the decades. I think it was a good course correction in some ways, but I think it can kind of go on hyperdrive too. 

And I'm thinking of a particular example in the present is that we've been hearing for decades now that you can be whoever you want to be and do whatever you want to do. And if you follow that all the way down, that is not great advice. My daughter has a friend who is convinced she's going to be a big star. And it's the sweetest girl in the world. So sweet. You know it kind of reminds you of those America's Got Talent tryouts where it's like, sadly this person does not have the talent. But they get a lot out of what they're doing which is awesome. It's so great. I don't know where do you, I guess there's like a discernment piece there too where folks who maybe don't have talent to do certain things need to wake up to reality and actually put their focus where their talents actually are.

07:25 Dave: That's a wisdom piece, you know? And that's the right word. The word we're talking about here is reality. Because it's only our assessment of success and failure in order to be accurate means that we have to understand reality correctly. And that's a real challenge, especially when our own self-worth is wrapped up into it. And so sometimes we don't have enough emotional fortitude to be okay with what reality is. And I think that's kind of one of my goals as a human being is to try to figure out what reality is no matter what it is and be okay with whatever that answer is. I know who I am as a person. 

I know exactly where my limitations are. And it's because of failure that I know where my limitations are. I can tell you exactly how many hours straight I can do. I can do 56 hours straight. I did that in college one time. A group project was bottlenecked on me and I needed to do the CAD. So I worked for 56 hours straight. People came in and did it after me. But it was lucid the whole time. I was working the entire time and it all made sense and people were able to actually use it and make it the next day. 

But there's another thing that happens when you get challenged to the extremities of what you can handle. And that's a really, really interesting thing that MIT does. MIT is going to find your points of failure as a person. It's going to find your limitations emotionally, spiritually, certainly mentally, in some ways physically. That's a painful process. Finding out where your limits are can be a very, very painful process. But boy, if you know where they are and you also understand how limits can grow and change with your own capabilities, how you grow, that's a really powerful thing. It's like going to work out. If I'm going to try and lift 500 pounds over my head, that's going to end pretty poorly. One way or another, that's going to end pretty poorly. What if I know exactly what I can handle right now, but I also know how to develop that skill over time and increase that safely over time by continuing. 

And the way you do that, right, is the process of practicing, continuing to lift, trying to increase. And that process is inherently painful. And the same thing is true for us. In anything that we're going to get better at than we are right now, that process has some pain inherently built in. And the kind of pain we're looking for is the pain that doesn't break. It's the kind of pain that has hurts just a little bit, but it's sort of like after a really, really hard workout, right, you're really sore. The same thing happens with your mind. When you find your mind getting stretched in new directions and learning something, there's a weird kind of pain that comes with that. But it's not a breaking kind of pain. It's a kind of pain that the more that you do it, the more that you actually stretch and grow as a person. And so finding where those limits are become enormously important because if we're only ever succeeding in life, that means that we're never trying anything hard enough that truly challenges us. It's actually only in failure that we find out where some of those real limitations are. It's only where failure is really nothing more than reality attempting to introduce itself to us.

10:17 *Matt: * And the question is, can we figure out the right things to learn? And so there's examples too of Font Awesome around, I'm thinking around the time of the Kickstarter that you guys were thinking of it, that these themes of failure were sort of on your mind that you were trying to build something that wasn't maybe quite the right timing. You thought there was a total wash, but then you learned after the Kickstarter or maybe during the Kickstarter that there were some really good things that came out of it. Can you talk a little bit about that? 

10:54 Dave: Yeah, so this was a time in the company. In 2015, we had done Y Combinator. In November of that year, we closed a round of funding. So it was a seed round. And that was enough to help us to go out and hire two folks. So we hired Rob and Brian. They came on board the beginning of the next year. And that gave us a runway of about a year and a half. 

And so what we did was we started running what I would call like a major experiment every quarter. We had so many visitors at Font Awesome that really all we needed to do was have one thing work and convert for us into paid that we could sustain a business of some kind. And so every quarter we were trying something different. The original product we made was called Fort Awesome. Terrible branding choice. It's too similar to Font Awesome and that's creates its own set of problems. 

But Fort Awesome was it was we wanted to help you not just with your icons, but all of your front end assets because it turns out to serve those well. It's its own rabbit hole and underground city that you can go down and live in. So we were going to live down there so that other people didn't have to so they could get back to the important work. And so you came to us, you uploaded your typefaces, you could upload your own custom icons. And we also handled images and automatic optimization and putting all the stuff on the cloud and making it easy to be able to get to. 

So we were running a experiment every quarter somewhere around there. So one quarter we made, we finished off and really made Fort Awesome. It's still out there and it's actually a good product. And we have very little churn off of it. Many, many, many people still use it years later and we still support it with security updates. We don't do a ton of feature development at all on it anymore, but it's still going and chugging along. But what we… 

Matt: And that helped to inform kits somewhat too, isn't that right? 

Dave: That's exactly right. We still think we were right about everything in Fort Awesome. We just built it in the wrong order. And that's what we were going to discover later that year. So we did that one quarter and finished all that off. And that actually was good work. And we still dog food that we still use Fort Awesome. Fontawesome.com still uses Fort Awesome kits because it's still the easiest way that we know of to deal with images and typefaces and a whole bunch of other stuff. So we ran an experiment with that. Didn't get the kind of signup numbers that we were hoping. 

Then we ran another experiment where we started something called Font Awesome CDN. This was for version four. We knew that ease of use is the killer feature. Our icons are good. The easier they are to use, the better. And we knew that CDNs were nice. Just being able to put a CDN link is on there is nice. But you also got to go in and manually update it when there's a new version. You've got there's just so many kind of nuances around which files are going to be serving, what's going on with all these little bits. So we created our own our own service called Font Awesome CDN, where you could go in and you could customize which version it was using so that you could come in without pushing code, you could come in and update to the latest version. You could also pick whether or not it was using CSS. 

We also had a new feature starting in version 4.6 called auto accessibility. So we could actually help keep all of your icons accessible. By default, do the right thing for your users without having to know that much about accessibility. All you had to do was throw a title equals on the icon and we would take care of the rest on the accessibility side. Title equals if there's a semantic meaning, otherwise it's just decorative and we'll treat it the right way. We still use that same technology in Font Awesome and it's still great because you can handle accessibility so easily with very little effort. 

What we were trying to do is we were trying to get people to come in to Font Awesome CDN and then convert over to Fort Awesome. So we worked for a whole quarter to make that process really, really smooth. We would even go and we had a way to know what icons your site was using. So you could come and put those into a custom kit in Fort Awesome so that you were only serving the ones that your site needed and we could walk you through that whole thing. 

After a quarter's work for four people, three months for four people, we had one person sign up that way. One. 

Matt: Oh, geez. 

Dave: Right? So first quarter, what we were trying to do with Fort Awesome looked like a failure. Next quarter, that one looked like it was a failure. And then the third quarter, I can't remember even exactly what the experiment was, but it also didn't work. 

So then we just kind of started backing up and we're like, okay, what's the simplest change from what people love at Font Awesome that they keep asking us for? And it's just more icons. That's it. And that's where the Font Awesome 5 Kickstarter came out of. 

We broke two records that still stand to this day for amount raised and total number of backers, which we want to break those at some point. But the reason that that worked, the key piece behind why that worked was because we had collected email addresses for the Font Awesome CDN. So we had this sizable email list we could send to, to let people know about the Kickstarter and whatever, all the news and stuff that's happening with the Kickstarter and keep people informed. And that list was absolutely vital because one of the truths, there's a lot of things that change in the world and over technology, but I tell you what, for as old of the technology as email is, email-

15:54 *Matt: * It's not going away yet. It works. It works.

15:57 Dave: It does. But we've taken a look at somebody's inbox and a whole lot of other things are in the way, but it still really, really works. Every single time that we would send an update about the project, the least amount we ever could directly attribute to that email was about $10,000. And we were getting ones as high as 40 or 50 grand from sending a single email to that list. 

And that list that came about what we thought was a failure. But because we had chosen what we knew intuitively was a wise choice. We knew that emails are important. If you're building users, it's really important to be able to contact them. It's vitally important to be able to do that. And we knew that was a key. And it turned out that piece of wisdom that we did just a good foundational choice, but it looked like it was a failure. And it turns out we were wrong. And this is the interesting thing so often that happens in life is that there are things that we think were failures. And overall, in broad strokes, they were. But if we do the process the right way for these things, nothing has to truly actually be a failure. That's what's actually fascinating about what we typically think of as failure is failure doesn't actually exist in a couple of situations. 

I'm going to go back to my time at MIT for this one. I'd already flunked at MIT once. I'd gotten back in twice, which I don't know how often that happens. And I was at my final semester. It was basically do or die. I had two classes left and I had thermal fluids engineering two that I was the only class I had ever flunked twice before. And this is a class thermal fluids engineering at MIT. 

Matt: Sounds like a flunkable class. 

Dave: So mechanical engineering is one of the degree programs at MIT that has the most number of requirements to graduate, which no one told me. I didn't know that going in, but also it was exactly what I wanted to do. And I'm glad that I did it. And so they had so many requirements. They realized that, you know what, three thermal fluids classes is too many. We just don't have time in the curriculum here. These are important to learn, but we don't have time. So why don't we take two MIT classes and condense it down or take three MIT classes and condense them down to two. 

When I took it, it was always different because thermal fluids engineering two, what it can be is so broad. Whoever happened to be teaching at the time just picked a whole different set of things they wanted to learn and teach. And so it was a terribly, terribly difficult class. And it was my final semester. 

And it was the first time where I was old enough, kind of having grown up a bit where I was like, you know what I'm going to do? I'm going to go to bed at midnight every night. I'm going to wake up at 8 a.m. I'm going to be responsible. I also knew that the way I learned was by being in class. I skipped an awful lot of classes earlier because I was young and stupid and didn't pay attention to how I knew that I learned. And I said, OK, basically go to sleep every night at midnight. Wake up at 8. Make it to every single class. But then I'm going to get to know people there because these are humans. The TAs, the professors, they're just people. I'm going to get to know them as humans. I'm going to build like real actual human relationships with them. And I'm going to do this my way. I'm going to do this what I think is the right way to treat people, to work hard and be focused. 

My deal was if I do this right at the end of it, if I still can't finish and graduate from MIT, that's OK. I can walk away because nothing is ever failure. If you've done it what you think is the right way. If you've done it the right way that you think for things that are character related or things that are things that really deal with your whole self, like having to finish somewhere like MIT, I knew that I could walk away. If I could not still graduate working the way that I felt was right and healthy, then that would be OK. I could walk away from it safely. 

I mean, I already had professional work experience. It wasn't even necessary. By the time I graduated, it wasn't even actually necessary that I do so. But it was an important thing to leave hanging out there. I didn't want to live the rest of my life hanging out, having a major thing like that left unfinished. But if it turns out when I went back and did my very best, did my best, did it the way that I thought was right, then that was going to be OK no matter how it turned out.

19:44 *Matt: * Yeah. And that's really wise because if you're beating your head against the wall against your own self, you're trying to play somebody else's game, climb somebody else's ladder, that's a bad way to live. You know, if you can say, these are my convictions. This is what I think the right thing is. I'm going to do it the way that I think is right. And if I can succeed, you know, then I can continue to move on in a certain direction. But I mean, gosh, to spend so much energy trying to play somebody else's game, it's not good psychologically, emotionally, or probably even ethically.

20:23 Dave: Yeah. I mean, that's the hard thing about most workplaces for most people. Most jobs don't acknowledge, like one of the things that we say all the time here is don't ever climb somebody else's ladder. Right? Yeah. And you have to often identify for yourself what success is for you and your life. 

And ideally what you're looking for in a company is somebody who's going along the same direction long enough that you can go with them. Right? Where those two things align where you want to grow and what they need done, what you want to do and what they need done happens to align. But most companies don't really treat it that way. Most people, most companies don't ever recognize that this will almost certainly not be the last place you ever work and treat you that way. Knowledge this and help you build your skills for wherever you're going to be next. Because climbing somebody else's ladder is always failure. It's always a form of failure. 

But climbing your own ladder and recognizing what is good and true and right that you believe how things can and should be in the world and you do that and it doesn't work out, it doesn't have to be failure. It doesn't have to be that at all because the only failure is, and this sounds terribly stupid and a trait, but the only failure is when you don't follow your conscience, when you don't follow your convictions of what you think is right. And some things there's not a right or a wrong, right? Like how am I going to make a grilled cheese? I don't know, right? There's lots of ways they're all kind of fine and they're probably people that have the right way and that's actually super cool. If you have that, I want to talk to you because that sounds super interesting. But it's not a character thing, right? It's just kind of an execution thing and you can get better at it. But there's so many things in life where the execution is dependent on the character. The execution is dependent on the way that we choose to do it and the why that we do this so greatly impacts the outcomes.

22:06 *Matt: * That understanding is key to understanding what success and failure really are. To summarize, there's a lot more kind of going down the hole and the details of all these different experiences. If there's somebody out there that's like grinding it out, maybe like a young entrepreneur or maybe somebody who's like in that mode of being in their head against the wall and they're not sure how they should be assessing things in terms of failure or when to move on or whatever. Based on what you've learned, what would be your bit of advice or encouragement to somebody in that space?

22:47 Dave: First and foremost, find somebody to do it next to. And if you have that person with you already, the entire process gets so much simpler. It gets so much easier. Because even if a single startup doesn't work, you're going to want to do it with the same people. If you took the time and you found good people to do it next to, they're going to want to be with you. They're going to want to come with you and do the next one. And that's the beauty of treating jobs first and foremost, thinking of the relationships with the people first. You do that part and that's a part of knowing who you are, figuring out who others are and relationships that are based on experience-based trust. That's exactly what… If you do that, then even if this one thing doesn't work out that the current project is, you can make the decision of whether or not, A, it might be that this is not work that works for your strengths. This isn't something that you really, really want to do. That's possible. 

And so the key thing, the key reason to do this alongside someone else you know and trust is so that they can help reflect reality back to you as well. Right? So that you can do this for each other. Because it's important first and foremost, you don't make up a world to live in where you're say startup is successful and then just believe that's true. You've got to go and find out if it is. Right? This is the reason why you go and you talk to users and you try to make something people want is you want to be introduced to reality as harshly and as often as possible and develop a way that you can be comfortable with whatever that reality is. Another person next to you is the best way to do it.

The other one too is sometimes we learn and we grow and we get better as we go. There are times where it's important to keep at it because we're so close to something big here. And then there are times where the right choice is to purposely quit. Be like, this is the time. This is the time to move on. When do you think is the signpost for that? And I think there are so many of them, so many different directions and it's not just one believe in yourself, right? That's not, I mean, maybe what does reality say? Is it something that you're actually good at? You tell me to believe in myself and go be a professional musician. That's not me. That's just not me. I know where my limitations are. I read if there's, you know, if there's something, I know where my limitations are and that's not something that I am experienced at, talented at, right? There's a whole list of reasons why I can want that all I want, but it's not going to change. Reality is not going to change. And I could certainly put a whole ton of time into this to try and, I don't know, put a ton of time in and try to go learn a musical instrument. But ultimately, is that what I really want to do? Is that my best use of time? And maybe it is. But if I've got other constraints, like maybe I've got a family I need to support, maybe I'm not independently wealthy and can't just go and do whatever I want. And those constraints, interestingly enough, are key too. Those are the constraints around all of it that help. Embrace those constraints, see those constraints. But there are the times where it's smart to quit and there are the times where it's important to push on. If you're doing the right people around you, wise people to ask for advice, man, that cannot be beaten.

25:46 *Matt: * Yeah, it seems like underneath all this stuff, a really key component is, really is just humility. Because if somebody approaches all these things with an attitude of humility, humility and trust is kind of what comes to mind. Is that if there's someone else you share trust with, you trust what they think, you trust their opinion, their instincts, they have a different set of skills than you and you have humility to hear what they have to say, you're at a pretty good place. Because then you can adjust, make changes, they can help you see your blind spots and then you're not going to be crushed if you see something that's quote unquote a failure. You can pivot and use it.

26:31 Dave: Yeah, those are the two things that come to mind for me. And where does humility come from? How do you actually, humility, that's a whole other discussion. And that for many people is one of the most important things to grow up is to figure out where these important character traits come from and how are you going to find them.

26:47 *Matt: * And that's not just a brain dump or a life hack. That's a character thing.

26:53 Dave: Yeah, those are some of the most important things to figure out in life. Underneath all of the other things, what are the ultimate drivers for you in life? There's nothing more important to figure out than that. There's nothing more important to figure out than that. It's hard enough to figure out the outside world around us. What's the mechanism for this photosynthesis, this thing that's happening, trying to figure that it is hard. That's really, really hard to figure out the outside world around us or other people. That's hard too. 

The most challenging thing to figure out in the world though is us. Because our own ego is so wrapped up into it. And that's why it is such a challenge to be able to see. And that's why humility is such a key component of that. Is that we can't be okay with who we might be. What if right now I am being an absolute jerk? What if it's me that needs to change? I need to go find help. I need to do something different. Sometimes that's the answer. And are we going to do it? Are we going to do the work that needs to be done? Or are we going to just believe, no, that's the other person? Because I tell you what, I'm a smart individual. I can always come up with a reason why something is somebody else's fault. And humility is a key component. That's one of the things that we look for most in people we hire is humility.

28:11 *Matt: * The ability to be able to say both, I was wrong and I don't know. Okay, Dave. So to summarize a little bit, we've talked about a lot of different things. We've talked about your experiences at MIT and things that you learned building around the time of the Kickstarter. How would you summarize the main takeaways of this conversation?

28:37 Dave: Try hard things and find the right person to do them alongside. And when it seems like the story's done, probably isn't yet. There's still more to the story to be told. There's still more to figure out. There's still more to grow in. And the only real failure is giving up, giving in, not making… There are two kinds of successful failures. There's choosing to stop because you think it's the wise choice. And there's choosing to go on because you think it's the wise choice. Somebody else alongside you, the right person next to you can help you figure out which one of those it is. The only really awful one is that you get so wrung out that you just stop and stop going

29:21 *Matt: * on and don't make the conscious choice yourself. And wrapped up in all that too is try and find somebody that you can trust and walk through this stuff with humility, which would be its own conversation all on its own. Yep, that's exactly right. See, I told you this episode wouldn't be so much of a bummer. So the big takeaway here is, I don't know, maybe if you're not failing, you're not trying stuff that's hard and you're not going to have an opportunity to learn. You don't want to do that. So thanks as always for listening in. And this podcast was produced and edited by yours truly, Matt Johnson. I want to thank Dave for coming on the show. And the theme music of the Fawn Awesome podcast was composed by Ronnie Martin and audio mastering was done by Chris Enns at Lemon Productions. Oh, and one more thing before I forget. If you like the podcast, please pass it on to your friends and subscribe wherever you get your podcasts. Please give us a rating and review. We'd really appreciate it.