Brian Lovin: Host of Design Details

Brian Lovin is the host of the Design Details podcast and is a product designer at Buffer. He also runs The Kollection, a music curation blog.

Hey everybody. I’m Sam Solomon, and this is Signal Tower. Today I’m joined by Brian Lovin, who is the host of Design Details, a podcast about  about design, development, products, interfaces, games, and more. He is also a product designer at Buffer.

Welcome to the show. Brian, if you would kind of tell us a little bit about yourself, who are you?

Yeah, you gave a good intro. So I’m currently doing design work at Buffer. I’m out here in San Francisco with my dog, enjoying life. I like experimenting with my routine and food and all that kind of stuff. I love starting music projects for some reason.

Yeah, with my dog, I enjoy experimenting with, with life and my schedule and routine and food and all that kind of stuff. And yeah, I love music. So let’s keep starting using projects for some reason.

When we were chatting before the show you said that you were experimenting with how little sleep you can get. I feel like most people are trying to figure out the opposite. What exactly was this experiment about?

So I was listening to another podcast with Matt Mullenweg, who founded WordPress.When he was young—in his twenties—he tried a polyphasic sleep. I had never heard of this concept, polyphasic sleep, before. So I started looking into it—basically there are people that have figured out how to get by on two or three hours of sleep.

And I started thinking about it more and more. As a maker, I’m always looking for ways to get back more time. You could—in theory—operate with the same level of productivity and mental focus, but have more hours in the day.. So sort of just jumped in.

I got to a point where for about two and a half weeks I was going on four—maybe four and a half hours of sleep per night. Now that’s not as extreme as the people that really work at this, but a couple of week only sleeping four hours a night is pretty extreme for most people.

That sounds pretty extreme to me. So what happened? Were you just as productive on four hours of sleep as you were before?

Yeah, some things are certainly better than others.

The whole thing with polyphasic sleep is you have a guess, transition period, adaption period and then you can move forward. For some people that may be a couple weeks, others may take months and then some people may never be able to get there. As someone that was close, but didn’t quite get down to two or three hours—I got an insane amount of stuff done some days. They were so energizing and encouraging and you can just go and go.

And there were other days where I’d wake up at 2 am, and not get anything done. I was awake, but might have just as well ben asleep. In those moments, you have to get through it. The whole idea is to keep going and push through those moments in the adoption period. You need your body to reprogram itself to accommodate a lack of sleep. The first few days like that were tough. By day 10 things got a lot better.

It was an experiment though. There are quite a lot of factors that work against polyphasic sleep that make it extremely hard for most people. You can’t miss your window by more than a couple of minutes. The way I was approaching it was sleeping three hours then supplementing three 20 minute names every day. You absolutely cannot miss one of those naps. It can be punishing if you’re not rigid—there’s no room for flexibility.

So that impacts social life and work. Someone would invite me to dinner or go see a movie and I’d have to plan around the handful of 20 minute naps I’d have to take to prevent myself from unravelling.

You can’t drink caffeine at all because it stays in your system for five or six hours. And that directly impacts your ability to get into your REM cycle. You can’t drink alcohol for the exact same reason. Any upper or downer alters your ability to get sleep. It alters any sort of progress you’re making.

In summary, you can’t have a social life.

I can definitely see how that type of lifestyle isn’t sustainable for most people long term. You know it’s cool that you’re trying stuff like this though.

Buffer is a pretty open company. Joel writes a lot and is fairly transparent with experimentation. I’m curious what he thought about this polyphasic sleep experiment?

Oh, Joel was super supportive. I think it worked out quite well given our teams are all distributed. I’m working with engineers on the other side of the world sometimes. It’s nice to be able to work on their schedule and communicate during their working hours.

I don’t think there was much downside for the company. It just didn’t wasn’t something I thought I could keep doing in the long run.

Maybe this is a good segue into talking a bit about Buffer. With everyone working remotely, what has your experience been like thus far? How do you decide what you’re going to work on and how do you work with engineers?

It’s soft of a long answer. In one way it has been a learning experience the last several months. We recently made a pretty major change to the company structure. There are no managers and no bosses. When you pair that with a distributed team you—you get some interesting results.

We have self-organizing task forces. These task forces focus on a specific problem, question or feature. There can be any makeup of skillsets on a task force. There’s not an engineering team building one thing, everyone splits themselves up.

You end up with, probably, a dozen task forces at any given time. The number of people can ebb and flow. Some may be doing customer support, others may research, while others are designing and developing.  All of these different areas are kind of nebulous—free-flowing groups of people that are working on different things.

One way to think about it—you’ve been interviewing at Buffer and you start selling yourself to work on a certain thing. Great news, you’re hired! Now that you’re in the company, you’ll need to sell your skills again to work on a specific project.

So as a designer I have to sell the other task force members that I can help them move the ball forward. I have to show them I can do customer interviews, interaction design, this is how I think through things and this is how I can help. The result is that you get natural formations of people that need each other’s skills rather than being forced into a place where you work on something because that’s what your job title says.

When you say a task force, I’m imagining a fairly small group working on a well defined problem. Is that what this is? There’s not like 20 people on a task force, right?

No. Nothing like that. It’s probably between three and five is like a good number. I’d say five would be on the high side.

That’s fair, but it probably changes over time?

So let’s say we’re building a feature. The task force may to bring in people for research. Maybe customer support so we have a frame of reference around a problem.

So now that we’ve got a better sense of the problem, we may need to bring in an engineer. And at that point it may make sense for the customer support person to move to another project.

You say it’s kind of self-selecting but is that from like a list of items that need to be shipped or bugs that need to be fixed? Or is there someone within this group that just says, Hey, I want to do this. And I need, you know, a designer and a front end developer to help me out with it.

Yeah. It’s a mix of all those things. We’ve got a list of bugs. There is a list of ideas for interesting features, but it isn’t like a roadmap—nothing that we have to build on in the future. Sometimes people just have crazy ideas.

Here’s an example—Well, maybe something else I should explain is this thing first. We have something called transparent email. This means there are 30-something employees sending hundreds of emails and they go to everyone. So basically everyone is copied on every email. Everything is visible to everyone.

That seems like madness. How do you separate signal from noise? 

We do have filtering systems that try and manage it. But yeah, it gets crazier and crazier with every new person that joins the team. It’s like exponential growth in the number of emails.

So going back to crazy ideas. Joel, another engineer and a researcher get together and say—this email thing is an issue. We’ve got to figure something out. So now the three of them are working on an internal tool to help separate out customer support emails—so there is more stuff about the product.

But it’s one of those ideas where someone said—you know what this might be interesting for us to build. It forces you to ask a lot of questions. Are there rules? Do we prevent people from replying with one-liners or gifs? I mean without rules a system like this really would be mayhem.

And maybe rules is not the right word—guidelines. A lot of this is stuff we’re still trying to refine. Like it’s not productive for someone trying to expense something to send that email to the whole team. Also, there’s very little change that person is going to hear back from anyone.

Right. When everyone is supposed to respond, nobody ends up responding—crowd theory—or something like that.

Exactly. Nobody wins.

I mean you can see how this begins. I have a side project I’m working on with three other friends. Basically everyone is copied on every email. But four people is a lot different than eight, which is a lot different than 30 people. Now we’re trying to figure out what does this system look like with 50 people or 100 people?  If we can get ahead of that, it would be ideal.

Buffer has some pretty radical ideas in comparison to traditional businesses. How’d you end up there?

So I would have been a junior in college at the time. It would have been around February. I was doing freelance design stuff. Working on random projects. I was a paying Buffer customer.

So back up—Buffer originally had three co-founders. One of the co-founders left in January 2013. And by February they needed help on the design side. Around that time I tweeted @Buffer jot to say—Hey, love the product and service! Something like that. It wasn’t the type of comment that solicited a reply. I was just letting them know I was a satisfied customer.

It just so happened that Joel saw the tweet, looked at my bio and saw that I was a designer. He sent me a message. We had a Skype call and I started working for Buffer on a contract basis starting that February.

So what are you working on at Buffer now?

Well, I mean, when there’s so much going on. Personally, I’m working on the onboarding right now. What does the product look like to new users? How do they get from our landing page to the dashboard? We want our users to recognize the value of Buffer as soon as possible.

What else? There’s this old jobs index that I build back in 2013 or something. We finally refreshed that. Now it better reflects the company. I’m generally working in more of an advisory role for that project.

One big thing is working on a better way to schedule a lot of content at once.  You can schedule one post to all your social media accounts through the extension right now. But what if you could schedule an entire marketing campaign from the same modal?

We’re always trying to figure out how we can help our customers be successful on social media? How do you reach the most fans? How do you get the most engagement and help them grow their following? For example, it can be useful to know when your followers are online. We can answer some of those questions with the data we have. How can we surface that to our customers?

Seems like there are a lot of interesting things happening at Buffer. What do you enjoy most?

Man, the team is awesome.  The team and culture that have been built over the last several years in incredible. We’re tight knit.

With everyone remote we don’t get to see each other that often, but every six months or so we meet up. It’s like a group of friends coming together after not seeing each other for a long time. It’s not like those awkward corporate company retreats where we go and people are doing trust falls and stuff.

Even when we’re working, it’s not rushed. It’s like—Hey, how’s it going? Let’s catch up. And there’s so many opportunities to build things with cool people through the whole task force thing. Honestly, that’s one of the best parts.

It’s very liberating.

And what about your side projects? I feel like you’re always working on something. What about The Kollection?

Yeah. The Kollection is a music blog I started between high school and college. It’s about five years old. And I built it as a way to share music with my friends. There’s a lot of great music coming from small artists these days. I wanted to make that music more accessible online.

The first month we had around a thousand visits. Then by the fourth month around a hundred thousand visits and now we’re reaching over a million people. So the project kind of blew up. It’s allowed me to meet some interesting people and build a small team.

I will say in the last two years it feels like the project has slowed down quite a bit now that I’m working full-time with Buffer and have some other side projects right now. The Kollection is still my baby, but I’m trying to figure out what the next steps are.

That reminds me a bit of my interview with Adam Wexler. He had a startup called GoRankem, where they were leveraging people’s opinions on music to surface songs. He’ll tell you that the music space is pretty tough. You must know that though.

I’m curious what attracts you do it?

I mean music is such a universal thing. Who wouldn’t want to build a product that can speak to everything—to everyone one.

So yeah, music is extremely attractive to me. You’re right, Adam is right, it has to be one of the hardest spaces to build something. Very few people will get any scale and fewer will find ways to make money with it.

I know that. It’s fine. I’ve always looked at it as a hobby or side project. I know how much work it would take to turn into a business and I know the odds of it surviving as a business are not great.

But I’m happy with what I’m doing. It is very much a creative outlet for me. It’s a place to experiment with design and programming and stuff like that.

That’s fair. Before the show we were talking about this list of goals you have. One of the things you mentioned was making an iPhone app. But you’re a web designer and developer, right? Do you know Swift or Objective-C?

Yeah, new year. New project. New things to learn.

You know I felt like I was on a different level in 2014. It felt like I learned so much and got better at so many different things. It’s more about pushing my own knowledge to the next level. It should be pretty easy for most product designers to transition to designing mobile apps. You need to be aware of some patterns, but it shouldn’t be that difficult.

On the other hand programming is something I can absolutely get better at. I can do some of it, but I’ve found that implementing some of my ideas in JavaScript or PHP have been the biggest roadblock I’ve had to implementing some of my ideas.

So how can I hold myself to some level of accountability? How can I incentivize myself to learn to become a better programmer. Setting goals like this gives me a push.

Sam, you’re a designer—you know. How can you expect to be a product designer working on the web if you don’t understand the underlying technology? You won’t be able to see what’s possible. Even if you don’t know how to program, you need to have some basic knowledge around that to be a competent designer.

I don’t know anything about iOS or mobile development right now, so I’m hoping I can learn a bit more that can help me inform my decision making.

That makes sense to me. I’m probably in the same boat—I’m extremely comfortable doing web design and some basic development. I’ve done some mobile design work, but really don’t have a solid grasp on mobile development.

What about your other goals? You said reading books?

Yeah, the one that’s had the biggest impact on me recently is called Reinventing Organizations

That’s that’s definitely fair. Well one of the other goals was, was you were going to read a book. And I’m curious. So what have you read? And I guess, what have you learned from those? Okay. So the big one was called Reinventing Organizations, which I highly recommend. It’s obviously about rethinking organizations. It has been transformational to us as a company. My guess is that everyone at Buffer has read it. Not a heavy book. Short read. But the ideas are around building a new organizational culture and the ideas are insanely fascinating.

It feels like we’re on the cutting edge. I think it might be the future. How do you get rid of bosses? How do you build a company where people aren’t cogs but have agency and are trusted to build things and are empowered and responsible by default? How do you do that?

I think they’re cutting edge and I think there’s a future. Where all reading these things and like, it has some of these ideas. How do you, how do you get rid of bosses? How do we build a company where people aren’t seen as cogs in a machine where they are, are trusted to, to build things they’re considered responsible by default.

It opens a ton of other questions—like, if you don’t have bosses how to you hire people? How do you fire people? How do you determine who gets paid? So it’s important to think deeply about. That book was an inspiration to me—the no boss concept. I don’t have answers, but it is fascinating.

Wait, wait, wait. So how do people get hired at Buffer? You put it to a vote? Can someone veto a hire?

Well when we switched to no bosses—look you can’t get rid of an important process and not have something else take it’s place.

So the way we looked at it was that if we can get rid of bosses and managers and remove a strict hierarchy—what happens in that vacuum? Leaders kind of naturally emerge. So if you’ve been at the company longer, you might have more context and experience. Perhaps, that means you can fill some role as a leader. So you get a more natural forming hierarchy. It’s not written in paper. You don’t get promoted from junior to senior to SVP.

If you’re good and you work with others well and can help and inspire them, you will emerge as a natural leader. That plays into different things like salary. If there are no bosses, how do you determine who gets paid?

We’re trying to figure out this too. I mean there are a lot of different factors that go into someone’s salary requirements. A single man living in San Francisco is very different than someone with three kids living in Michigan. What do each of them need to live a fulfilling life?

We’re running out of time and there’s one thing I really want to talk with you about. This year you started a podcast, which I think is pretty cool. I’m curious what pushed you to start a podcast? What prompted that decision?

That’s funny. I was sort of reflecting on that this morning.

So I started this blog series called Design Details last year. It was just a handful of blog posts that dug deep into the UI and UX of some of my favorite apps. I looked at Twitter and Secret before the redesign. Pinterest and Flickr had some great ones. I was just doing a bunch of breakdowns. And in November, a buddy here in San Francisco reached out. We chatted and met up for dinner—kind of a brainstorming session. How do we take this format that all written and visual and translate it to an audience?

We realized that maybe we could try something different. Sort of separate the visual part and have a conversation with the person that made the app. It seemed really disruptive at the time. But we were going to have a show about the people doing the design work.

With that sort of ethos, we decided, yeah, we’re just going to have a casual conversations with designers and developers. We’re two month into it. Episode 10 comes out tomorrow. Well, depending on when you release this—so early March. But yeah, I think the concept is cool.

Well, I think the Design Details series is fantastic. I’m curious how do you decide on guests. How does someone end up on the show?

Well for the blog posts, I probably have 150 apps on my phone. I really just download everything and study it. What are the main interactions, how does it feel. What’s unique about it?

If it catches my eye, I’ll really explore it. For example I did a review on Tumblr. I poked around and I see it surfaced a lot in Google searches. It would be cool to chat with someone from Tumblr hand have them on the podcasts, but it doesn’t necessarily line up one-to-one. Like we just chatted with someone from Dropbox. We haven’t done a design blog posts so there’s a but of a disconnect.

We’re also trying to get a little outside the Silicon Valley bubble a bit. We chatted up Cap Watkins in New York. In general I’d like more people with different backgrounds on—people freelancing, or working in agencies, startups, bug tech. How can we bring all these people’s ideas together?

I could be mistaken, but do you guys have sponsors? You have a few, don’t you? How have you gone about getting them and how do you decide who to reach out to? Are you cold emailing people you know?

Yeah, I think we’ve been very lucky so far.

We were bouncing the idea around a recent dribbble meetup here in the city. Turns out I live in the same building as some of the designers there. It comes up naturally—hey we’re doing a podcast. And we’re trying to reach designers—they are also trying to reach designers.

So it’s kind of spontaneous. From then on we started recording weekly. And we kind of just get a lot of people emailing us. Most of the sponsorship inquiries have been inbound so far. Maybe we’ll do some outreach in the future. I’m not sure yet.

So you’ve been doing Design Details for a few months. What lessons have you learned putting the show together?

Oh man, I love these questions. I think there’s a blog post about this somewhere. But there are a few things for me.

One of the big ones is just how to talk. I’m certainly not very good at it right now. I used to say like a lot. I’m trying to be consciously aware when I’m talking with someone. You know it takes practice and reflection. We’ve reflected quite a bit in the last two months. I think we’ve become better at talking and carrying-on. I’m learning how to guide some of the conversation, which I’ve never had to do before. In terms of podcasting itself, everything is new. I know nothing about mic setup or recording and such.

It has been awesome reaching new people. I think there’s a lesson in just being bold with your outreach. I message a lot of people on Twitter and just drop them a line—Hey, love the work you’re doing. It makes their day and maybe you get a new fan.

I think a lot of it is knowing what you want to do and reach out with an open mind. Maybe this person knows something I don’t or have a connection I want to meet. It gets easier and easier. Now with almost a dozen episodes under our belt, it only gets easier—but you keep doing it.

I get it. You’re grinding away and helping people and being friendly—that’s how you get an audience. I love it.

Brian, we’re close to time here.Do you have any last thoughts or advice for our subscribers? Maybe something on becoming a better designer?

You know it can be hard to give advice like this, because I’m religiously processing stuff. I’m always taking things from here and there. Maybe the context isn’t always the same, but there’s always overlap.

You know, I think the key for me is to always be learning something new. I know that sounds cliche, but it’s actually quite challenging in practice, right? It’s easy to sort of get stuck in to one frame of reference. I’m a designer, so I design all the time. So learning CSS has been challenging, but immensely helpful

Learn Sketch. Learn Photoshop. Learn how to blog. Why not learn how to podcast? Read more, write more. There’s so much stuff you can be doing, you just have to start. As a designer you have a great starting point. Keep expanding and keep pushing yourself. See what different ideas that you can bring to the table.

Yeah, for me, that’s been, been immensely helpful. And for people that, that have the credence to design and work from a computer and program, I think it’s an incredible opportunity to be able to do that and to be able to work with information from the desk and it configured and use your mind. So I would advise people, I would recommend people to take advantage of that.

Great ending. Thanks for joining us! Brian, where can people find you?

Well, brianlovin.com is still up. You can follow me on my podcasting journey. Make sure to check out Design Details.

Thanks so much for having me! This was a blast.