design MBA

Managing Side Projects - Brian Lovin (Staff Product Designer @ Github)

Episode Summary

My guest today is Brian Lovin who is a staff product designer at Github. In this episode, we discuss the following: - What was Brian Lovin like as a child - What gets Brian Lovin excited about blogging - Brian Lovin's framework to figuring out what and how often to blog - What drives Brian Lovin - Brian Lovin's relationship with money - Importance of ownership in a business if you want to get rich - Brian Lovin's journey of starting Design Details podcast and podcast network Spec.fm - Brian Lovin's framework for deciding when to shut down a side project - How Brian Lovin got the idea to start Spectrum - Raising $400,000 seed round - Pitching to the right set of investors - Getting acquired by GitHub - Productivity cycles - Taking time off to recharge - Brian Lovin's advice for designers For show notes, guest bio, and more, please visit: www.designmba.show Level Up Your Design Career (Free Email Course): https://levelup.designmba.show/

Episode Notes

Brian Lovin is a designer, podcaster, writer, and software tinkerer. He is currently building native mobile apps at GitHub. Before GitHub, he co-founded Spectrum, a platform for large-scale communities to have better public conversations. Spectrum was acquired by GitHub in November, 2018. Before Spectrum he designed payments experiences at Facebook, working across Facebook, Messenger, WhatsApp, and Instagram. He also co-host the Design Details Podcast, a weekly conversation about design process and culture. 

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Episode Transcription

Namaste and welcome. This is Jayneil Dalal and you are listening to the design MBA. This podcast is a real-life MBA program for designers where we interview design hustlers and learn the skills, mindset necessary for a designer to launch a business venture. You can learn more. Find past episodes and stay updated at designMBA.show.

 

Why are you listening to this podcast? Think about it. Deep down you want to grow in your design career. And I’ve been in your shoes. I’ve pushed pixels for years without really knowing how the hell do I grow in my design career. So, I’ve created a free email course for you to help you level up your design career. The strategies I share in the seven-day email course are actionable and used by over 700 plus designers with success. So, head over to Levelup.designMBA.show or you can find the link to this email course in the show notes. Level up your design career today.

 

Jayneil Dalal:  Today, I got a phenomenal guest with me, Brian Lovin, who is a product designer podcaster and writer currently living in San Francisco. He is right now designing native mobile apps at GitHub. Before GitHub, he co-founded Spectrum, a platform for large-scale communities to have better public conversations. Spectrum was acquired by GitHub in November 2018. Before Spectrum, he designed payments experiences at Facebook, working across Facebook Messenger, WhatsApp, and Instagram. He originally cut his teeth as the first product designer at Buffer. He also is a co-host of the Design Details Podcast, a weekly conversation about design process and culture. Design Details is part of spec.fm, a podcast network for designers and developers which he co-founded in 2015. You can find him on Twitter where he talks about design and development or on GitHub where he's building out in the open or in Figma where he's exploring how plugins can automate the tedious part of interface design.

 

Without further ado, Brian, welcome to the show, man. Super happy to have you on.

 

Brian Lovin:  Hey, thanks so much for having me. This is cool. 

 

Jayneil:  Oh my God, dude! I cannot tell you when I was trying to start my podcast, you were like, and you still are, what do you call them, north star for me what I should do with a podcast, where I should do and I’m “I got to have this guy on. It's simple.

 

Brian:  Wow, that's a compliment. Well, thank you. I hope the podcast old enough all these years later. It's been a lot of episodes.

 

Jayneil:  So, what was your earliest foray in the field of design as a child? Did you think about you were going to be a designer?

 

Brian:  No, no. I guess I just started becoming interested in the internet more broadly. So, if you hear enough interviews with people my age, you basically get these themes and for me it was like Myspace themes, Neopets, and GeoCities, that vibe of internet culture where you could actually tinker, you could view source, you could start to play with the fabric of what a website actually was. And so, that's where I got interested in things like HTML and CSS. And so, from there, that leads you down the rabbit hole and you get into WordPress and then you start building WordPress themes and all this kind of stuff. And so, that's where I started building websites and that was, I suppose, in high school I started building websites.

 

Jayneil:  Oh my God! 

 

Brian:  I ended up just starting a lot of blogs. I don't know why but I blogged a lot from high school all the way through college, just constantly writing. I didn't really get interested in design, design until college. I was running a blog at the time called The Collection which was a music blog helping people sort of discover and download music from independent artists. And I realized at some point, I ran that for five years, maybe around year three or four, I realized I didn't care as much about the music as I did about the experience of discovering and downloading and playing, organizing that kind of part of the website. So, I spent a lot more time thinking about how the website should look, what cool features we could build that would help people download easier or queue up a list of songs to listen to that kind of thing. And I guess that would be where it first clicked “Oh, this is designing something and I can see some outcome from it.” I guess, to be technically specific, the first time I ever got paid to design something would have been in high school and I made like forum banners for people for 20 bucks or something.

 

Jayneil:  No way! I see that that habit of blogging, you still continue now on your personal website at BrianLovin.com. What got you excited in this art of sharing your experiences, just writing blogs?

 

Brian:  Oh, I don't know. I guess I have to repeat a couple clichés here and they're clichés, I think, because they're true. One, I think the process of writing actually forces you to really contend with the way you think about the world. So, I to have a topic in mind and say “All right, I want to say something about this. I want to have a point of view about it.” And as you start writing that, I start to argue with myself, I weigh the both sides of it and you have to sort of fight your way through to the end of the blog, post refining your thinking along the way. So, I try to do that and I like that. And then another framing that I find really helpful and has proven correct is Sahil Lavingia, the founder of Gumroad, he had this metaphor or simile. He said “Writing is like building a cache for your brain and your thoughts.” So, that means instead of having to have a one-on-one conversation with every person who has a specific question, instead I can actually just write about it, put it on the internet and that knowledge sits at this layer in between my brain and the person who's interested in a particular question. And so, I find that that framing is kind of cool because it means you can have the thought once and lots of people can respond to that or read about it. And so, yeah, I guess that's what it is for me. I like forcing myself to grapple with finding an answer to a question and then taking that internal conversation and publishing it and seeing what other people think as well.

 

Jayneil:  So, it's not like … because there are a lot of people who want to grow their blogs on Medium or just become a prolific writer on Medium for monetization or what that might be. Do you blog when ideas come to you like “Oh, this is something I’ve been thinking about for a long time. People haven't said much about it.” So, do you chase stories that come to you or do you just set a schedule like “I don't care. I’m just going to churn out a blog every Friday.”

 

Brian:  I got to say I’m off and on. So, my current blog, I revived that earlier this year. So, all the posts are fairly new. Then I ended up not writing it all for five months in the middle of this year with the pandemic. I was at home with my family and just kind of divorced myself from side projects and writing completely. I only just recently started it back up again but I think to answer your question, I just keep a running background list of things that sort of happen, problems that I encounter at work, problems I encounter with side projects. I keep a list of those things as they come to mind. And then I prefer having a schedule. So, for me, right now, I’m going to say Sundays I want to sit down and like work through one of those things on the list. I guess I would say, it kind of reminds me of podcasting. The only reason podcasts are so compelling is because they are habitual. You expect them at a certain cadence. Whether it's weekly or monthly, people get into a habit of expecting something new and a continuation of that story. And so, I think the same goes for writing, at least for me. I appreciate people who can stick to a schedule and just say “Look, this is the day that I’m going to do the thing.” So, for me, I record Design Details every Sunday night with Marshall. We have our scheduled down like clockwork. We do the same thing every single week. And once you have that sort of mechanical process, you're basically forced to just do it. You just do it. You don't think twice about it. There's no grappling internally “Oh, well, I’d rather do something else. I wish I could go play video games.” Instead, it's just like “No, this is the thing I do at this time of the week.” So, as far as writing goes, I’m not there. I took, again, like five months off this year but historically, with some of the past blogs I wrote, that was the ideas. There's a certain time and I just got to stick to it and once it becomes a habit, you just stop thinking about the decision to do it.

 

Jayneil:  What drives you, man? Because you started out in high school learning how to design websites, started your own startup with The Collective. And you talk about “I’m going to sit down on a Sunday and write a blog.” I mean, majority of the people might on Saturday be partying out and wake up late on Sunday. So, there's got to be something that drives you. So, what is that thing that drives you?

 

Brian:  I don't know. I’m sitting here thinking about this for a while. I don't think it's a specific thing. I guess, I’m very curious about stuff. I like to solve problems. And when you solve a problem, you inevitably just go down this rabbit hole of things that you have to learn about. So, if you want to build a website, you have to learn about how to have a domain and that leads you to having to learn about DNS and that leads you to having to learn about thing after thing after thing. And it's just this compounding effect of you're always learning something new. And that process is addicting. I find that process of learning something new, getting to be shitty at it then not so shitty at it and then you ship things and then other people use it, that feedback loop is incredible. It is such a rush. I love it. I would say there's like an aspect of … in the past, certainly money played a huge role in it when we were working on The Collection in some of my earlier blogs, really thinking about monetization and how do we make money from the time that we're putting into that. These days, I’d say side projects are less about money and more just about scratching an itch like there's a thing that that is annoying in my life and I feel I could figure out a way to build a solution for it even if I’m the only one that uses it. I don't know, maybe that's not a super satisfying question but I think it really is just fun like this is what I would prefer to be doing. I also enjoy partying and being out with friends and doing those kinds of things but I also just have as much fun building stuff or designing things or nerding out. It's just fun.

 

Jayneil:  Wow! And I’m just thinking about it, you said, at this point … money was a huge motivator early on and now it's not. I’m wondering what changed there. Was it because you started investing in an early age? I know you wrote an article about investing for designers. So, what is it because you invested in an early age and you saw that “Okay, I think now I have enough of a safety net.” What led you to that peace of mind that “Okay. Now, I can relax. It doesn't have to be money all the time.”

 

Brian:  Yeah, I mean, I should clarify. Money is still a motivator. I guess there's three prongs to it. One, I want enough money to have a lifestyle that lets me be comfortable like can I afford groceries without having to really pay attention to the person as they're ringing up all my items like can I just buy groceries, can I afford to go to the movies and not blink twice although, of course, that's not happening this year but that level of do I make enough money to just have a lifestyle that feels comfortable. And I would say it helps that I’m not particularly spendy into things like clothes or shoes or anything that. So, I end up saving money naturally that way. So, that's the first is like do I make enough money to just have a life where I feel comfortable. The second part is am I making money in a way that is fair. I would say actually this is the one thing that I think is the most clear reason to not talk about money with your peers, which is that once you discover somebody else who's doing the same amount of work as you is making more money for that work, all of a sudden your quality of life becomes relatively worse. That sucks. So, there is an “ignorance is bliss” sort of element to it but I do like the idea of fairness. Even if I’m comfortable, I want to be sure that for the effort and skills and contributions I’m bringing to the table that I’m being compensated fairly. And then the third element is am I making financial decisions that will pay off for me in the long term. And so, that's investing, that's thinking about equity in my jobs or building side projects that have some sort of equity built into them, so things like spec.fm. And that, I guess, is probably where I’m more interested now like how do I actually build meaningful equity and things that are going to be around for a long time so that I can have a lot of fun day to day, I feel good, I have the lifestyle I want, I feel like I’m being treated fairly but it's all adding up to something so that in the future I can perhaps work for myself and not need to have the bi-weekly paycheck.

 

Jayneil:  And have that big payday.

 

Brian:  Yeah, I don't know. I guess, I’ve never had that but if you sold the company for a billion dollars, I imagine that would be quite the rush.

 

Jayneil:  So, can you elaborate the example when you said have that equity with spec.fm. So, can you just explain what you meant by that and explain that through the example of spec.fm.

 

Brian:  So, spec.fm is a podcast network. There's like 10 shows. I don't know the latest numbers but we've certainly paid out hundreds of thousands of dollars to hosts who run shows on the network. So, we have sponsors. We actively help the shows on the network get sponsors. And I’m a one-third owner of the business and we have terms where owners of the business take a certain percentage of revenue. And so, that is money that, I guess, accrues or grows as the business grows. As hosts are successful, so are we. And if the business ever shuts down or we have residual profits or money in the bank, I have ownership over a piece of that. And so, I think that's important. I believe that that really is the best way to actually make meaningful money is to have ownership in a thing. I think it's really hard to actually get rich just making weekly salary.

 

Jayneil:  I absolutely agree with you. I think, and these are just clichés again, requoting like Nassim Taleb saying that “The two most powerful addictions are heroin and the steady paycheck.” 

 

Brian:  Oh yeah, that bi-weekly paycheck. It's true. 

 

Jayneil:  So, what got you to start the Design Details Podcast? Because you started way early, I think in, if I’m not mistaken, 2015. 

 

Brian:  To that, we have to thank Bryn Jackson. So, at the time, in 2014 I started writing a series of blog posts called Design Details. They're still up. They're on my website. I’ve called them App Dissections now. I would record screen recordings of apps and I would just try and dissect the little details, little animations or cool elements of the design that I found to be playful or interesting or fun or engaging. I mean it was perfect timing when I launched it. The first videos I recorded were from Twitter and they used to have some really cool details in their iOS app. And like a week after I published that, Facebook dropped Facebook Paper. And if you remember Facebook Paper, that is the Design Details goldmine. Every single thing in that app is considered and interesting and playful and it moves and it shimmers and it bounces. There's just so much to explore there. And so, I wrote a post and recorded 20 something videos from the Paper app, just added some notes about what I thought was interesting or what I liked. Anyways, those posts did really well. People also liked reading those and watching the videos. And so, I kept making those posts. I just kept writing these Design Details blog posts for maybe a year. And then Bryn Jackson, who is a friend, we'd met a couple times in the past but he also lived in San Francisco, he reached out and he was like “Yeah, I’ve been looking at the posts. They're cool. I use them for reference and inspiration. What if instead of just speculating about why these details exist or why the thing was designed in a certain way, rather than speculating what if we just asked the people?” And so, Bryn had a background in audio production and he brought the skills to the table to make a podcast, so mic, equipment how we were going to record, how we were going to produce and edit all this kind of stuff. And he said “We should talk to the people that are making really awesome products.”

 

Jayneil:  And you brought that amazing voice.

 

Brian:  Yeah, that was my one contribution. Seriously.

 

Jayneil:  I think you naturally have that affable voice which makes you laugh. It's very welcoming.

 

Brian:  Well, that's awesome to hear. People have said that. Everyone hates their own voice. I still hate it. I’m just used to it at this point because I’ve heard if for hundreds of hours. I do the show notes every week. My co-host Marshall, he edits and produces and then I do the show notes. So, I’ve listened back to myself for hundreds of hours and still hate it but that's great to hear that someone likes it.

 

Jayneil:  So, when you started out Design Details, was it part of the strategy that “Oh, we’re going to reach out to all the makers and shakers in the design industry and we're going to get to network with them”?

 

Brian:  Kind of. I would say it really did come from a place of curiosity. We wanted to know why things were designed the way they were. Bryn is a little further ahead but we were both relatively early in our careers and like “How do we just ask people? How do we get better faster by just figuring out what people are doing and why they do it?” So, what we did is we just put together a list. I think we ended up with like 100 something people in a spreadsheet of people who are doing interesting work in the industry like people we've been following on Twitter, people who are working on interesting products and we just sent a bunch of cold emails and we managed to get a few people. Well, a lot of people replied yes and a couple of the people who replied yes happened to be influential designers in the industry. So, I think our second or third episode, Wilson Miner came on the show and it was kind of cool because when we reached out to him, he's “Oh, I’ve seen the blog posts. Of course, let's talk about it.” And so, that kind of clicked together really nicely but I would say one of our strategies when we first started was I had heard, I don't know where, could never find it again, but I had heard that most podcasts never make it past the eighth episode. And it's kind of working out or going on a diet. It's most people, you do it the first few times, you feel really good about it but then the motivation wanes and you just … So, we're like “All right, we got to at least beat the average. We have to beat eight episodes.” So, strategy was we were going to record eight episodes before we release the first one. So, no matter what, we've beaten the average. We almost hit that. We recorded five ahead of time before we released the first one. And that bought us some breathing room. So, we recorded five, we released the first one and we knew that we had over a month before we had to do anything else. We could sort of take in feedback, figure out if we liked the vibe, plan the next iterations, plan the next guests, that kind of thing. And so, I would say that really helped us just get that momentum we had this, not a backlog but a front log of content that we could release.

 

Jayneil:  And from that point on to you building out spec.fm, how did that idea come about?

 

Brian:  That one happened pretty naturally. So, we launched Design Details at the same time, I think almost the same week as another podcast called Developer T by Jonathan Cottrell and we were chasing each other up and down the charts on Apple if you look at the top tech podcast or design podcast, I forget the category. It was always us just flipping back and forth. I don't actually remember the specifics but we reached out at some point, one of us reached out, we were like “Hey, we should team up. We could cross promote. You're doing developer stuff. We're doing designer stuff. There's some collaboration opportunities there.” And so, we ended up deciding to form a podcast network. We called it Spec. And then the idea was we wanted to just build a place that had resources for designers and developers and the motto was “How do we help people level up.” We love this idea of getting to the next plateau of your career, of your skills and are there ways to shortcut that by creating great resources, tutorials or, in our case, podcasts and interviews. And so, it's kind of grown slowly but organically over time. There's been some shows on that have since retired and are kind of in the archived state but there's a handful of active shows that are producing content weekly and has ended up becoming a nice little community of designers and developers who follow along, which is cool.

 

Jayneil:  So, you and the team are reaching out to podcasters that you like and saying that “Hey, if you become a part of this network, we can provide you all the resources and stuff and let's collaborate together,” something like that?

 

Brian:  Yeah, we did that early on. The deal was we'll help sell sponsorships and like for sponsors, we can give basically bundled deals like rather than the marketing person who we're talking to having to do a deal per show we can just say “Here's one deal. You're going to get on five shows, you'll get this many downloads.” So, I made it easier from that point of view so we could help people make money, which is always great and then the second part of course is we can cross-promote. So, we actually built out spec.fm. We started pointing people there. We would mention other shows. As new shows joined the network, we could announce that on our own respective podcasts and sort of help launch that new one, so to speak. So, that was the deal. We reached out to a few, some of them were just friends who were experts. We were like “You should do a podcast. Here's a microphone. Record weekly. Go.” And then over time, we had others sort of join us because they enjoyed making content but they didn't like the part of producing, editing, distributing, and doing sales. And so, they said “If somebody else can do that and all we have to do is talk for an hour every week, that's more sustainable for us. So, let's see if we can join the network.”

 

Jayneil:  So, if somebody runs a design podcast and wants to be part of your Spec network, what do they got to do to get your attention?

 

Brian:  When's this coming out?

 

Jayneil:  It's a good question, sometime early next year, maybe Jan or Feb. I haven't decided a date yet.

 

Brian:  Okay. Well, at the time, this is released spec.fm will be shut down. We're shutting it down at the end of the year. You're going to have to go start your own podcast network. That's the solution.

 

Jayneil:  And if it's okay with you, if we can dig into that, why shut down this, I don't want to say goldmine, but this network that's giving other people a chance but also, it's generating money and you're a business owner? So, what set of events led you to do that?

 

Brian:  So, there's three of us and we've been all participating for five years with varying degrees of intensity, I would say. The person on our team who has been doing absolutely the most is Sarah. She has been doing weekly newsletters. She still produces. She does sales. And between the three of us, over five years, at some point, you just have to make a call like what's the opportunity cost of spending my time doing this every week. I said we've paid out hundreds of thousands of dollars to host but that doesn't mean that all the three of us are sitting here making hundreds of thousands of dollars. No, we aren’t making barely any of that. We're making a tiny portion of that. And so, from a financial perspective, it's great but it's not this is making us rich. It's not it could ever be a full-time thing unless you really, really put work into it. And ultimately, I’m not interested in running a podcast network. It's kind of the same thing as what happened with the blog I ran in college, The Collection. I love the content but I’m just more interested in doing other things with my time. I prefer building products and designing. I like having a job where I’m building things that hopefully are helping the world. Side projects come and go and this is a side project that I am lucky to have worked on for five years and been a part of. And at the end of five years, we collectively kind of just said “You know what? This was a good run. Let's end on a high note and spend our time doing something else.”

 

Jayneil:  And was it hard emotionally saying goodbye to the baby?

 

Brian:  You're asking me before we've done it. So, I will preemptively say, yes, it's going to be weird. The thing that I’m most interested in doing is preserving the website. I would love for the URLs to live as long as possible. So, we will keep spec.fm up. We will try to ensure that every URL works so that people can find old content, old Google results, get people to the right place. We just won't be actively doing sales and production and adding new shows or anything like that but hopefully, the site will stay up. So, as people are listening, if you go to spec.fm and it's still up, that means somehow, I’ve figured out how to do it but the business behind it is not operating. 

 

Jayneil:  I see. So, while you were doing the Design Details Podcast, doing the spec.fm and stuff, where did you get the idea or how did the idea to build Spectrum come about?

 

Brian:  So, this one was really organic too. So, Bryn and I were doing the Design Details Podcast, Jonathan was doing Dev T. And as the network grew, we wanted a place for designers and developers to hang out. So, we built a Slack team which is what everybody does. We had a Slack team and started inviting people to that. We made a forum to make it really easy to join the team. At the time it was kind of tricky to join a Slack team but we made it really easy and a lot of people joined and we're hanging out and sharing things and talking and it was really cool. I think at the end, maybe the Slack team had 7000 or 8000 people in it but we heard this rumor, which turned out to be false, but we heard a rumor that Slack teams would not allow you to go over the 10,000-member mark. We were on the free plan obviously, can't afford to pay for all those people. And so, we were put in this position and we were like “Okay. Well, if Slack won't work for us in the long term, what are the alternatives?” And so, we looked at things like Facebook groups, we looked at Discourse which is more traditional forum software, we looked at Discord, there's a product called Gitter which is like a developer-oriented sort of real-time chat platform and we just weren't satisfied with any of the alternatives. We wanted something that was real time like a place that people could hang out but also had a preference towards the longevity of content like every thread has a URL, which doesn't exist on Slack or at least not easily, it's just not accessible to the open web. And so, that's why we started Spectrum. We said “We want a community, a place for our podcast network community for designers and developers to hang out, to share ideas, to talk but we want it to feel like a place where people also want to just have the tab open in their browser and check in throughout the day and hang out. So, there's got to be a real-time nature to it, a presence nature to it, some element of fun and community.” And so, that's why we started Spectrum. And then we ended up joining with our third co-founder Max Stoiber. He created several very popular open source libraries, probably the most popular which is Styled Components, and he had very similar problems in his world, in the developer side which was he has this large open source community and no place for them to go. He wants a place where people can hang out and get to know each other but also where content is persisted, people can Google for it and answer their own problems and questions. And so, that's why we teamed up with Max. Well, we needed his engineering expertise, of course. And we brought the design side. So, it felt a good fit all around. And so, the three of us made a pact. We were all going to quit our jobs on the same day. It was very exciting. Went in, told my manager, had the conversation, thumbs up, “All right, I’m heading out” and then just ran outside called Bryn and I’m like “I did it. Did you do it?” – “Yes, I did it.” – “All right.” It was very exciting.

 

Jayneil:  So, did you think about it like “I’m going to save up the money and then hit a certain number and then quit” or was it just like “It's now or never. Let's just quit it.” 

 

Brian:  I saved and I think we all had saved. We had a buffer and we ended up bootstrapping for the first six months.

 

Jayneil:  Wow! And did you think about “Let's just raise the VC money from the get-go as soon as we start” or what was your thought on that like just raising venture capital?

 

Brian:  The reality is that taking venture capital puts you on a certain path and we wanted to buy ourselves some time before making the choice of whether we really wanted to be on that path, which is basically you need a big exit at some point in the future versus having maybe more of what people would call lifestyle business. We just weren't ready to make that decision and we'd saved up, we had a little bit of runway. So, we said “It's a little premature to sell ownership in the thing that we're building. We're not really even sure what it's going to become.” So, we spent the first six months just building. We launched a beta in like six weeks, got people using it, started getting feedback, people were excited about what we were working on and, as it grew, I would say, it was like two lines crossing where one line is how much money we have in the bank and another line is “Oh, we think this thing could be big.” And when those collided, we were like “All right, we should raise a little bit of money, give ourselves some more time to explore and go deeper on some of the problems here.”

 

Jayneil:  So, how was that process raising the VC money for you?

 

Brian:  So, Bryn really led point on raising money and he did a great job. We did a seed round. So, this was a very small round from people who we'd met in the industry, warm intros from those friends. So, it's a very small group of people. I think we raised a little over 400,000 dollars. I only participated in one check and I was with somebody who I’d worked with on the internet for a while … I don't know, I don't like fundraising personally, I did not like the process but the nature of who we raised from and the small amount that we raised, it made it not so much of an issue. Later on, when we were raising another round, I was maybe a tiny bit more involved. And I’m either not good at it or I just don't like it for some reason. So, maybe it's something I need to get better at but I found it really hard to really answer the question “How is this a billion-dollar company?” when in my heart, I wasn't actually sure that's what I wanted. And so, I felt I was making up just shit. I mean, people were asking “How is this going to be a Facebook?” And I don't know that I wanted to run something like that. So, I’m like “I’m not sure.” And so, I didn't like the binary nature of it where it's either you're a failure or you're a billion-dollar company. And I think, in retrospect, I didn't look hard enough for the types of investors who are okay in the middle ground. There is a class of investor who look for something that isn't a billion-dollar company and that is modestly successful in the seven or eight or nine-figure range, just not the 10-figure range. Anyways, I, in retrospect, should have just done more research, found the right kinds of people to pitch to. I think we pitched to the wrong kinds of people. 

 

Jayneil:  So, looking back, would you have gone the route of just growing with revenue-based growth and just not even pursue the VC route at all, if you could go back in time, or it is what it is?

 

Brian:  If we could have, we would have. I think the problem with building a community product is the time to revenue for an individual customer is quite long. So, if you imagine, really any way you slice it, for somebody that's creating a new community, it's going to take them some period of time for the community to either become large enough or complex enough where they need certain tooling to manage. It just takes a long time to get there and that means there's a long time between their sort of acquisition, joining the product and the time to revenue. And so, we just didn't have enough time to really see that through but, I guess, that would be awesome. I think that would have been fun to have it really be a revenue driven thing. 

 

Jayneil:  So, after that point, you raised venture capital money. What set of events led you to consider that “Okay, I think we might be okay with an acquisition” or specifically, how did the GitHub acquisition happen?

 

Brian:  It just so happened that most of the communities that used Spectrum were in the developer and designer space and I think that's just because of the nature of the three of us. We're all designers and developers. That was our audience. That was our network. It's who we could talk to. So, we had a pretty vibrant set of communities from the developer space. And so, GitHub reached out and they were also investing in “How do we build great community tools for developers?” And so, when GitHub reached out, we all kind of did this independent audit, we each put together our own spreadsheet of “All right, if we could work at any company, here's a list of 10 companies that we all admire. Rank them by product, people, remote friendly,” I don't know, there's a few other variables. We all rated them independently, combined them into a single spreadsheet. And all three of us, the number one across the board by a long way was GitHub. 

 

Jayneil:  No way!

 

Brian:  So, we like GitHub. It is a product we all use, we love. We've gotten to know the people there. It's an amazing team, such a cool culture, such a cool brand. So, I started talking to them. And the opportunity to build community products for all developers, at least open source developer communities, is pretty exciting. So, we pursued it and got very lucky that things worked out and we all got to join GitHub. 

 

Jayneil:  If somebody were to join GitHub as a product designer versus coming through an acquisition, I’m assuming with acquisition it's a better deal because you get more stock.

 

Brian:  I don't know. I think it depends on deal, the kind of product, the kind of person. I imagine every deal is a little bit different. I can't share specifics, unfortunately. I would say everyone has a different deal depending on the leverage you have as a product coming in, the kind of person and background you have and the value that you can bring to the organization.

 

Jayneil:  And when you had the conversation with the VCs, they were totally okay with it. I mean, the people you raised money from, I guess.

 

Brian:  So, we raised money from seed investors and I think seed investors or angels are a class of people who recognize the odds of that money actually flowing through to some huge payout is very slim. Most startups fail or have some sort of acquisition or acquihire event. I think for the people we were working with who do lots and lots of deals, they've invested money in lots and lots of companies, it was kind of a normal thing to hear about.

 

Jayneil:  Wow, man! Full circle. I see this amazing entrepreneur driving you and I wonder how do you manage two parts. One is you're working full-time at a company now. So, obviously, you can't just go ahead and do whatever side project you want. That could be conflict of interest. And the second part is the time management. So, how do you manage both of these things?

 

Brian:  Well, the conflict of interest part, I think it depends on the company. So, GitHub is very side project friendly, probably more than most companies. So, I’ve never worried once about things like spec.fm or the Design Details Podcast or any of my personal projects, never worried about it. I guess if I was building like a direct git competitor like, I don't know, code collaboration product, yeah, that's a conflict of interest but I’m so far away from that that I haven't had to worry about it. The time management side, like I said, this is fun. This is what I to do on evenings and weekends. I would say that I go through like six-month cycles of high productivity and low productivity. And I’ve just learned this over the years. I wish it wasn't that way. I wish I was more consistently productive but I’ve just found that I have six months, where I get a lot of shit done and then I need six months to chill out and rest and recover. And so, I get a lot of stuff done in six months and I take a lot of time away from other things. I would say social media is the biggest one. I would say my productivity and time spent on Twitter are directly and inversely correlated. Twitter is hugely distracting and the less time I spend on it, the more time I’m bored enough to work on other things but, yeah, I’ve just learned to roll with the waves. If I’m having fun, if I’m in the zone for whatever that six-month kind of high, I just try and get stuff done because it's fun and that means taking away from other things that you might be doing in your free time. I should also add I don't have kids. And so, if I have kids, I imagine that changes the equation, that just reduces the hours. So, there are certainly factors that that just help have a few more hours in the day to work on things after my main job.

 

Jayneil:  And in the six months that you're not productive, you've come to peace with it that “Hey, this is my time where it's okay to be not 100%, that I can take the time off, chill, do whatever else I want.”

 

Brian:  I don't know, maybe come to peace … I find that period really frustrating and that one is directly correlated with how much I play video games. I find that I’m drawn to video games when I’m bored or exhausted from everything else. And there's probably an element of escapism or there's something about control of progress and dopamine hits of leveling up or getting better or whatever it is in the game. There's something about that that scratches an itch that I’m apparently not getting elsewhere. I wish it wasn't that way. I’m still grappling with this. It's not really come to peace with but just more recognize that this is a part of my personality and something that seems to happen over and over again. I would love to reduce it, to have that time period be shorter or find ways to remain productive throughout, I don't know. I’ve stopped beating myself up over it, if that is maybe close enough to coming to peace with it. I don't beat myself up if I take a couple months and don't work on side projects, which was why I didn't write anything for five months this summer. I was like “You know what? Fuck it. I’m off. I’m going to hang out with my family. It's a pandemic. Nobody gives a shit. Everyone's got their own stuff to worry about. It's okay. The world will continue spinning.”

 

Jayneil:  Oh my God, man. That is such an amazing place to be at. I’ve struggled with it. I still struggle with it at times. And I think a lot of people just listening would all be envious in a way everybody wants to get to that point where it's okay if nothing's happening or no progress has been made. I view it as a sine wave. 

 

Brian:  Yes, that's exactly it. 

 

Jayneil:  So, I see like when it's going high, everything is great, you know other things are going to come but then the way I’ve said it in my head is like the bottom trove comes to the sine wave when things are just not coming out. I found that as also being a very deep and reflective phase for me. And the only reason why I’m able to say this to you is I’ve been journaling for the past … I started in 2013. So, now it’s almost seven years or so. Now, it's become a weekly habit. So, I’m able to go back in time and see my post and then every year I do a yearly audit So, that's where I was “Okay, I think there's just some kind of pattern a sine wave. There's some ups and then downs” but then the learning for me was always the most in that downtime when nothing was happening or tough times or whatever you want to call it.

 

Brian:  That's interesting. Have you found patterns or things you can do to get through the trough like things that get you excited about the work again?

 

Jayneil:  Yes. So, for me, the way I was able to figure some things out that were working for me specifically was like in all the journal entries I do, I use the Journey App, I’m able to hashtag like #sad, #anxiety, put my emoji mood in there. So, whenever I don't feel doing anything, I’ve noticed, for me as an extrovert, that I always was able to recharge myself if I just started booking back-to-back meetings with people “Hey, you're in town, man. Let's grab coffee. What's going on with your life” and just shooting the shirt. So, that really helped me, number one. And number two, I also found that in some way giving back in that time like going out of my way, so it could be going to an event and mentoring someone or helping someone in whatever capacity you can, I found that to be helpful. And then third, correlation is I always like traveling. So, every time I went away from that and went to Mexico or some South American country, I would come back a little bit more recharged.

 

Brian:  That's awesome. Yeah, that makes sense. I love the way you've described it as a sine wave. I have this blog post that I’ve been working on in my head for three years, which is just about that wave idea. And what I’m trying to grapple with is if you should strive to sort of flatten the wave, so not as high of peaks but also not as low of valleys. And we can get into some interesting sort of philosophical conversations about the merits of this like the super-high highs are super high, they're awesome, they're super exciting but the trade-off is you're going to have super-low lows. And if you strive to compress that to something that looks a little more like a smoother wave or even a flat line, then the exciting things are not as exciting and yeah, maybe you don't get quite as down about things, maybe your life feels a little more boring, I don't know. That's the trade-off. And I think, personally, I would still strive to flatten those waves. I think that would work better with my personality. And it's cool to hear you're an extrovert. I’m an introvert. So, when you said “I need to talk to people to recharge,” it gave me goosebumps. I have to be away from everybody to recharge. I cannot talk to you over a long period of time. So, I think there's something interesting there like figuring out if you're the type of person who actually wants flat waves or if it's okay to just enjoy the highs, let them be as high as possible, live it, enjoy it, love it and then brace a little bit for the inevitable down.

 

Jayneil:  Now, the one thing I’ll add, and this is getting super philosophical, is the wave is going to go high or low. How high it goes and how low it goes is also based on our perception. So, recently, I got into a very high conflict situation and that forced me to read into philosophy. So, I was reading books like The 50th Law by Robert Greene and 50 Cent and then I read some other philosophical ancient texts. And kind of the message I got from the whole thing was that wave is going to be the way it is going to be. You can't change that but what you can change is how you react to it from the internal perspective. So, to that regard, what I’ve been doing, and this is just something I started a week ago, is kind of sitting still every day in the morning after I do my workout for 30 minutes and doing nothing. I call it my form of meditation where I just do nothing. 

 

Brian:  That’s awesome. It sounds terrifying.

 

Jayneil:  I used to chant before but then the way the brain was that I would chant and then I would utter some Indian chants and stuff that I learned when I was a kid but then my brain is thinking about that thing and then I’m trying so hard “don’t, don't come into my mind. Don't come into mine” and I was chanting even faster and louder and I was exhausted. So, I just was like “You know what? 30 minutes, let the brain do whatever the hell it wants to do. If it wants to fight, it wants to fight.” I think Naval was talking a little bit about this and I tried it out finally. So, that's been a little comforting. 

 

Brian:  One thing that I realized a couple years ago is I was going through literally weeks at a time where there was hardly a minute that I wasn't consuming some kind of information. If I took a walk, I was walking my dog, had a podcast in. If I was at my desk, I was working on a browser on a screen. If I was online, I was on Twitter like 24x7 just shit coming into my head and no time to process any of it. And one change that sometimes I do this, probably should do it more, just go for a walk without even music. I call music part of that sensory overload. You're listening to something, you're processing. Just go do nothing but, for me, I couldn't sit still, I don't think. Maybe I should try it but for me, it's at least walking around, walking my dog. That feels good and energizing but not listening to something, not reading anything, not focusing on anything, … at one point, I just realized I’ve gone weeks where I haven't done this once. I’ve always had something in my ears or pointing in my eyes and that was scary. That's not good. We shouldn't have that. So, less consumption. I’m a huge fan of that.

 

Jayneil:  I couldn't agree more, man. You're such a young guy, man. And then know when you started out, you had this crazy trajectory. So, what would you advise other people that want to have a meaningful career like you and follow that trajectory? What advice would you give to designers, anybody listening who want to kind of follow in your footsteps?

 

Brian:  I would say don't try to follow in my footsteps. I mean, this is just one of those things. Look, I found things that work for me because that's the way my brain works. Certain things scratch itches in really satisfying ways for me. So, I suppose the abstraction of that is like find something that is fun and scratches your itch and you get excited to wake up every morning and work on whether it's design or you realize it's not design and it's something else. I know people that have transitioned into research, they've transitioned into product management, they've just said “Screw it, I’m going to go be an engineer.” Any of these things, whatever it is, you should be having fun doing this. This is really exciting work that we get to do and it should be fun. If you don't like design, don't try to force it. I think everything that I’ve done or worked on has just been this compounding like there's a logical progression to each of the things like started making websites and created blogs, then started creating podcasts that led to the network that led to the community that led to Spectrum that led to GitHub. All of these things are just dots along a trail. And trying to recreate that line of dots just won't work. It's not possible. So, figure out what your dots are and I think part of that is just trusting the process, part of it is just having fun and being curious. And regardless of where those lines are going, at least you're enjoying it along the way. I could probably just leave it there but I’ll add one thing which is I’ve really become interested and they have all turned me onto this which is this Principal Agent problem. And it's basically how do you think a founder, how do you act every day as though you are the principal or the owner of the thing that you are working on. And that was the cool thing about starting Spectrum is you're forced to do that, you are the owner. No problem will just magically get solved by someone else. You have to solve it or it will not get done. And taking that mentality, mindset, energy, and willingness to solve any kind of problem even if it's outside of your wheelhouse at your day job, I think that's a superpower because nobody does it. Nobody does that, you stand out, people want to work with you, they recognize that you are taking the time to solve problems that you don't have to be solving and they're more likely to go out of their way to help you. So, we can have links in the show notes. I think Naval's articulation of the Principal Agent Problem is way better but that mindset of I’m showing up to work not to get paid. I’m not showing up because designing is fun. That's a nice side effect but I’m showing up to make this thing successful. I’m here to solve real problems and thinking like the owner of a business or wherever it is you're working. I think and I’ve experienced it changes the way that people want to work with you and the kinds of doors that will open up for you. So, I don't know if that's universally applicable but it's something that's worked for me and had some results so far.

 

Jayneil:  I love it. And how can people contact you and say thank you.

 

Brian:  Well, my DMs are open on Twitter. Hit me up on Twitter. Happy to chat with people. That's probably the main way. My email is on my website, if you're on email instead.

 

Jayneil:  Awesome. Thank you so much, Brian, for taking the time, man …

 

Brian:  Thank you.

 

Jayneil:  … to chat with me. 

 

Brian:  This was fun. These are great questions. Yeah, I really appreciate it.

 

Jayneil:  Absolutely.

 

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