Jamon Holmgren / COO of Infinite Red

Transcript

Jonathan Today, our feature guest is Jamon Holmgren, who is the COO and one of three founders of web and mobile app development shop, Infinite Red, headquartered in Portland, Oregon. Infinite Red works with clients in over eight countries internationally and has a team of 22 and runs a fully-distributed organization. During this episode, we’ll talk with Jamon about his experience personally working remote, as well as his experience running a distributed organization. Jamon, welcome to the show.

Jamon Thanks, Jonathan. Really appreciate you having me on.

Jonathan Excellent. So, you want to give us a little blurb about yourself?

Jamon Yeah, sure. So, I’m the Chief Operating Officer, one of the three founders of Infinite Red, and I live near Portland, Oregon, in, actually, Vancouver, Washington, and I’m married, I have four kids, and I love on about three acres. So, I’m not in the city. I’m kind of out, slightly rurally, but it’s maybe, like, 20 minutes from Portland.

Jonathan And I think that the acreage requires a riding lawn mower. Is that true?

Jamon [Laughs] That’s true. When we built here... We moved in in May, and when I built, I had to buy a riding lawn mower. Luckily, I also have an 11-year-old boy who functions as a remote control. I can just put him on it and point out the direction to go and he does it.

Jonathan That is... I would not have hated that growing up. I mowed lawns and had a lawn-mowing business, but it was the push mower kind and it was not as much fun.

Jamon Me too. [Laughs]

Jonathan So, I started remote work back in 2008, and one of the things that I learned is you have to have a why. What’s your core reason for the desire to work remote? Can you tell us a little bit about what your why is?

Jamon Yeah. I would say, if you kind of boil it down to the core reason, it would really be about my family. Obviously, I have kids and my wife, and it’s nice to just be at home. Like, if I go to get a snack or a drink or lunch or something, I’m typically walking through my kids’...unless they’re at school or something, but they’re there, and my wife’s there, and it’s just nice. I really enjoy that part of working remotely.

Ari So, Jamon, let’s talk about travel. Do you have to travel often, or does travel play into the whole remote thing for you? Do you kind of stick at home?

Jamon You know, we were a little bit unsure about whether we would have to do a lot of traveling when we first started the business. But honestly, we haven’t had to do too much. I do a quarterly in-person meeting with my two cofounders, so we’ll fly to, typically, Las Vegas, where our CEO lives. So, we’ll work together for a couple of days just to kind of stay in touch. So, once a quarter, I’ll fly over there. We do fly everybody into one location for an all-team sessions for a work week. So, there is some travel there. But as far as clients, projects, things like that, we really don’t travel hardly at all. We try to do as much as we can through video calls, instead.

Jonathan So, can you give us an overview of how you started your company, which, I believe, was back in 2005, and kind of the history of it, to where it is today?

Jamon Yeah, sure. So, my dad worked in construction and I started working in construction, as well. So, I was working for a home builder here in the Pacific Northwest, and I was in charge of the website, because I was, you know, one of the more technical people. This was 2002 up to 2005. And he was just really unresponsive, really not very good at customer service. He was a fine programmer, but he just was terrible at this sort of thing. And so I thought, you know what? I love programming. I’ve been doing it since I was 12 and I think I can do the business part of it better. And I know he’s making good money, so I’m just going to give this a shot. And so, in 2005, I quite the home builder business and I started just doing websites, initially. And then over time, I started hiring new... I think I hired my first employee in 2008 or so, and just kind of gradually started adding to my team. I was working at home at the time when I first started, and then in 2009 got an office, and was in the office until, really, this year, when I started working remotely again. So, then in 2015, I merged with another company called Infinite Red. My company before had been named ClearSlide. And so, ClearSlide and Infinite Red, we merged the two companies into one, and that’s where my two cofounders came from. They were partners in Infinite Red originally. Because we were doing so much work together, it was like, “Hey, you know, we do a lot of work together, a lot of projects together. Why don’t we just try it out, see if we can make this one thing?” And that’s worked out really well.

Ari All right. So, overall, you hear a lot of discussion about remote DNA, meaning that the organization is built from the ground up with that idea of being remote as part of the whole culture of the company. Was this the case with your original company, with Infinite Red? Or did you kind of start out... You said you got an office. Did you start out with people in the office and then eventually kind of work out into a remote culture?

Jamon Yeah. So, when I got the office, everybody worked at the office, and I just kind of built my team there. Up to about 12 people were in the office at the peak. And then we started doing more remote work, because I was always pretty open to the idea. But it wasn’t really built into our DNA until we started talking with Infinite Red, which was originally a remote company. I mean, they started that way. And so, when I started kind of absorbing their ideas, Ken and Todd, my two cofounders, then we started kind of...people started drifting away from the office, and that was okay. And I was one of the last stragglers because I was building my home, so I didn’t really have a place to work outside of the office. But once we actually did the final merge in October of 2015, then it was definitely 100% all ahead on the remote work. That was going to be... I mean, one cofounder over in Las Vegas, one in the Bay Area, and one in Portland meant that we had no choice. We had to be a remote distributed company.

Ari So, do you have an actual office that some people report to, or are you still actually truly, completely remote?

Jamon We do have an office. Two people work there. It’s a mobile developer and a web developer, and so they don’t work on the same projects, typically. And for all real intents and purposes, it’s really just a co-working space for them. We keep it so that we have somewhere to send mail, and once in a while, the people in the Portland area might meet up there, but I maybe get there a couple times a month at most.

Jonathan So, with the employees that you have at Infinite Red, how many of them had worked remote prior to Infinite Red? And when you bring new people on, do they have previous experience working remote, or are they transitioning out of more of a traditional setting?

Jamon Very few had remote experience coming into Infinite Red, and that still seems to be something that is kind of an anomaly in our industry, even though it shouldn’t be. Most people came from working in an office. They’ve had to adjust. They’ve had to kind of find ways to be productive. As we all know, working remotely isn’t the same. You don’t have the same culture. You don’t have the same motivations that you would have walking into an office and sitting down at your desk next to the same people that you’ve worked with for a while. But, surprisingly, it’s worked out really well.

Jonathan So, do you have an onboarding process of, “Hey, now that you’re working remote, this is how we do it”?

Jamon We’re still developing that to some extent, because we brought our two teams together, and then our goal was, okay, now that we’re 22 people, we need to really figure out what this means. And I think over the last year, we’ve gained some really valuable insight. We’ve been working on it the whole time. We do introduce them to our tools. We tell them here are some best practices for using Slack, for using all of the other remote tools that we use. But the way that we really try to do it is to make it where the obvious answer is the right answer. So, we’re not trying to force people into a certain way of working. There are some things that we have as standards, but we really try to make it so that people don’t really think about it; it’s just natural. So, for example, let’s say that someone has something they need to talk with a new person about. They’ll just say, “Hey. Here’s a link. Let’s jump into this Zoom video call,” and they kind of absorb it from there. So, it’s a little bit organic at this point. We don’t really have a formal way to train people into being remote, but that’s a little bit...it’s kind of on purpose, in some ways.

Jonathan So, what are the top five tools that you’re using remote to run your company and operate it?

Jamon I would have to say Slack is number one, with Zoom as a very close second. We’ve tried every video conferencing tool there is, and zoom seems to be the one with the best quality, with the most people in it. So, Slack, Zoom. Of course, we use GitHub. We are using InVision for our designers. That’s really great. And let’s see here... We also use, of course, Dropbox and some other random tools, as well. But those are the primary ones, I would say, that we’re on every day. Really, Slack and Zoom are really big. We do use Screenhero, as well, for remote pairing, but that’s less common.

Ari With Slack, have you looked into using their newest feature with the video chat? Have you found that is an alternative, sticking within Slack, or no?

Jamon Yeah, we have. We’ve done some tests with it. It’s got a little ways to go. It blows up your CPU and the quality isn’t that great. So, I think that it’ll be awesome once it’s stable, but we’re not finding that to be the case quite yet.

Ari Yeah, CPU usage seems to be a big problem with a lot of people with Slack, but it’s such a great product, I think people fight through it.

Jamon I think Zoom also kind of blows up your CPU. What it’s doing, though, is it’s trading processing power for a tighter bandwidth. So, it’s really... You get great quality. The bandwidth is very... You don’t use a lot of bandwidth. One of our team members is almost always... Two of our team members are almost always on LTE hotspots.

Ari Oh, boy.

Jamon Yeah. They don’t blow through their data, even with using Zoom for video calls. So, that’s been a very big plus for us.

Jonathan Oh, man. That’s impressive. I had one situation where I had to jump on a Google Hangout over my Verizon LTE, and that sucked up a gig of data like no other.

Jamon Uh-huh. That’s right. No, they measure it and they’ve found it to be very reasonable.

Ari All right. So, speaking of tools, given the type of work that you do, a lot of development, do you find that—or do you have it set up, rather—that your employees are working more kind of autonomously? They’re working each on individual tasks as they see things that need to be done and so on? Or do you have a more collaborative approach where people are working more in teams, continually working on the same projects and the same tasks towards the end goal.

Jamon It’s a little bit of a hybrid. I’m more team-oriented than individual. We typically have two developers and maybe one or two designers on a particular project, plus a project manager. And we like to work very collaboratively with the client, as well, so we bring the client into our Slack. We have them use Zoom, things like that. And so, people are collaborating quite a bit throughout the day. In fact, I’ve found, I think, that I interact probably more with team members now that we’re remote than I did even in the office, because it’s just really easy. You know, you don’t have to get up from your desk.

Jonathan So, in managing your team, how do you handle performance feedback? In some traditional corporate settings, there’s 360 reviews and that type of thing, but how do you manage your team in that regard? And then kind of a follow-on is one of the terms I heard used recently is when someone starts “submarining”, or they basically drop off the grid. How do you handle those situations?

Jamon Yeah, totally. Those are things we think about quite a bit. So, there’s three founders, and each of the three founders has a third of the team, plus or minus. And we organize those into what we call guilds. So, a guild is essentially... I have one guild with, I think, five people in it, five or six. We get together fairly often on video calls just to kind of hang out, even though we’re across different disciplines — designers, mobile developers, web developers. And I also handle their one-on-ones. So, I’ll do one-on-one video calls. You’ll notice a lot of consistency here. We do a lot of video calls. That’s really important for a remote company, in my opinion.

Jonathan It seems to be a reoccurring theme.

Jamon Yes, it is. I feel like some days, I’m on Zoom four hours out of the day. But yeah, I mean, that’s the team aspect of it. As far as the submarining, that’s an interesting term. I haven’t actually heard that before, but it’s really...that is something we think about, people that kind of drop off a little bit. And I would say that our CEO Todd Werth is one of the best at kind of just making sure everybody’s engaged and working. Not every day, but almost every day, he’ll send a message to each team member just saying, “Hey, good morning,” you know, “how’s it going?” Just little chit-chat. Nothing big. He doesn’t rely on anything to say other than just, you know, “Hey, how are you doing?” and “What’s up?” And I think that that’s not really a remote only thing. It can be really important in offices, as well. But I guess it’s a little easier to hide when you’re remote.

Jonathan So, how spread out is your team, then? I mean, if you have enough overlap that you can say good morning and good day, what’s the spread of time zones?

Jamon Yeah. Time zone’s really the biggest challenge with remote work. So, we tend to congregate more on the Pacific Time Zone. We do have some stragglers in Central and Eastern Time Zones. Our team, about half of us are in the Portland area. Those are mostly people who came from the ClearSlide end of things. And then we have some in the Bay Area, some in Louisiana, some in Nevada, one in Ontario, one in Florida. So, we’re kind of spread out that way. And the stragglers just try to have enough overlap. They typically are getting up a little earlier than us and getting done with their work day a little earlier than us, but it works pretty well. We try not to have someone, you know... If we had someone maybe in, like, Eastern Europe or something, that would be really tough.

Jonathan Yeah, or even Perth, Australia. I was working on one project once, and I think it was a 12- or 14-hour...I think it was an almost 14-hour spread, and man, I had some weird hours for those calls that we made.

Jamon We have some Australian clients and that can be very tough, as well as East Asia.

Ari All right. So, now we talked a bit about time zones and all this, Jamon, what does a typical work day for Jamon look like, given you’re working from your home and remote and all that?

Jamon Yeah. So, my job has changed quite a bit since I was a software engineer. I used to code most of the day. But I’m more just kind of on call. I’m constantly participating in a little meeting here, a little meeting there, just making sure that my team is...you know, everything is rolling. They’re really great, so I typically don’t have a lot to do on the operational side. I just kind of help set up systems and make sure that things are rolling, and I do the scheduling, as well. So, we might have a meeting in the morning like we did this morning where we discuss our schedule out for the next month or two, and I kind of do that. I might be in a few calls. I answer email. I’m in Slack all the time. Probably half my time is jumping around in Slack, and just kind of that sort of thing. Once in a while, I’ll still have my own little project I’m working on, as well. And I do a lot of sales, so Todd and I do sales calls as a pair. We do a video call and we’ll both be on the call, and then we follow up after that with estimates and proposals, things like that. So, that’s essentially what my days look like, and I don’t get to do a lot of coding anymore, so when I do, it’s usually kind of late at night, “Hey, I’m playing with some Elm or something.”

Jonathan Ooh. So, in your sales cycle and working with your clients, you’re obviously a remote company. How many of them have you actually met face-to-face?

Jamon Very few, actually. Yeah. It’s kind of interesting. And this is one of the pre-qualifications that we do, is if a client’s not willing to engage us just based on a video call—video call basis, I should say—then maybe they’re not a great fit for us. We do have a few where we meet with them more often, in the office if they’re in Portland, or maybe down in the Bay Area. My cofounder Ken might meet with them. But those are the exceptions rather than the rule.

Jonathan And what tool are you using for your video call with your clients?

Jamon It’s always Zoom. Yeah, we just love Zoom for both internal and external communication. And so, we have them download it and we kind of teach them to use it even during the sales part of it, and it works well that way.

Jonathan Excellent. So, switching topics just slightly. So, you personally, what are some distractions that you face and how do you deal with them?

Jamon Yeah. So, obviously kids. I have young kids and they don’t always respect the door that I have on my office. My wife can sometimes poke her head in and say, “Hey, you know, I’m running to the store. Can you watch our youngest while I’m away?” And that’s usually okay, but that can be a distraction, as well.

Jonathan So, what’s the age range that they are?

Jamon My oldest is 11 and he’s my only boy, and then I have three girls ages eight, five, and three. So, those are the primary distractions. Obviously there’s, “Oh, hey, the sink’s plugged. Can you come fix it?”, that sort of thing that normally would wait until I get home.

Jonathan It seems to me that the WiFi going down... I know about it from my wife and my daughter before I’ve realized it’s down, often. And it’s, like, instantaneous. “The WiFi is down! You better fix it!” [Laughs]

Jamon [Laughs] Exactly.

Jonathan In fighting isolation and being disconnected, what do you do for yourself to avoid that? I mean, you have your family locally, but you’re still part of a much larger team, and it’s easy to get disconnected. How do you build that camaraderie?

Jamon Obviously, we do a lot of video calls. Remember, I was talking about the guilds earlier. We’ll do, like, a video call with all of the guild members and we’ll just sit there and kind of shoot the breeze. It’s really informal. Just to kind of get some bonding time. We do the one week a year where we all work together. And we also do, every two weeks, we’ll do an all-team meeting on Zoom where we have 22 people on the same video call and we give out announcements and we talk about things and we joke and all that sort of thing. So, that’s important for bonding with our teammates. But as far as outside, I have noticed that when I’m not out and about, when I just walk up the stairs to my office, that I don’t get out of my house many days. So, I’ve noticed you do have to make more of an effort to go to things. I actually really enjoy going to meetups in Portland because of that. It’s not too far away, and usually I can get one of my team members to jump in with me, and we head down to the Elixir meetup or the [INAUDIBLE 00:23:54] meetup.

Jonathan That resonates well with me: forcing yourself to get out of the house.

Jamon Exactly! [Laughs]

Jonathan Because, I mean, in Northern Wisconsin here, even, most of my trips out of the house involve taking my daughter to school, and that’s just a half mile away. There’s no stop lights or stop...there’s two stop signs. But beyond that, it’s easy to just stay.

Jamon Yes, I know. And I think it’s important to get out of the house, even if you maybe don’t feel like you need it. It’s still important just to plan it. You know, just put it on your schedule, “Hey, I’m going to go do this thing,” or, “I’m going to go do that thing,” because otherwise you end up just being kind of a hermit. The crazy thing is I don’t feel like I’m lacking for social interaction at all. I’m talking to people all day long.

Jonathan Yeah.

Jamon But it’s more about just kind of getting out and about.

Jonathan There’s an Oatmeal cartoon that gets a little bit crude, but it starts off with the progression of when you work from home, and it comes from...it ultimately ends up with an utter slob of a blob just being stuck at home. And it’s funny because there’s some truth to the risk of that happening.

Jamon Right, exactly.

Ari Pants optional.

Jonathan Yes, this is true.

Ari Yes, except on video chats if you want to get up for a cup of coffee or something.

Jonathan Oh, man. Yes.

Jamon You just kind of slide off the screen before you stand up.

Ari Yes.

Jonathan You flip that video off and say, “Oh, sorry, I’m trying to conserve bandwidth.”

Jamon Exactly. We actually do that, though, like if we’re getting up to go grab a cup of coffee or something, we’ll just flip the video off, and that’s fine. You know, like it actually works great.

Jonathan Yeah. So, you’ve made that culturally acceptable, to just be able to, like, take a moment and...

Jamon Right. Yeah, no, we totally...yeah, we totally do that.

Jonathan That’s awesome. Well, I have something to admit, and that is I have actually always worked with pants. For my psyche to be like, “I’m going to engage in work,” I have to have pants on.

Jamon Oh, that’s interesting. Yeah, I rarely wear pants. I’m usually wearing shorts, you know, just because it’s easy.

Jonathan Yeah.

Ari Sure. So, with the availability to work at so many different times a day — in fact, I mean, being able to get out of the house... We didn’t really discuss if you do work strictly in your home office or elsewhere, but when or where do you find yourself most productive, in terms of time or day, or perhaps a location, if you sometimes work elsewhere besides home?

Jamon Right. I don’t work outside of the home very often. Once in a while, I will work from a coffee shop or something like that. My days are rarely... Because of my position at the company, my days are rarely judged solely on head-down productivity. Usually, when I’m doing something head-down productive, that means that I haven’t delegated very well. So, my job is very much to be more on call and thinking a little bit...it sounds a little cliché, but I have to think a little more big picture, like looking at the systems and our sales and things like that. So, I haven’t found that any particular time of day is more productive, at least now, because of my current position. I just kind of take things as they come. I will say that I do sometimes really value late nights after my kids have gone to bed, and I’ll jump on and I’ll get some things done, just because there are few distractions from either end, home or from work.

Ari All right. So, it sounds like you find different times of day, a little bit here and a little bit there, which are good spots to get different jobs done.

Jamon Totally. Yeah, absolutely.

Ari Do you have any strategies or systems to help keep your productivity up during those work times? Any tools, maybe?

Jamon You know, I’ve tried different things, RescueTime and different types of clocks and things like that. I do find that keeping a fairly clean inbox is important for me. I actually recently wrote an article on our blog, which is shift.infinite.red. I wrote an article about inbox zero and how I keep my inbox clean and free from subscription, clutter, and things like that. So, that’s really important. One of the nice things about being remote is it’s extremely easy to disengage and just focus. So, really, what you need to do is you say, “Hey all, I’m dropping offline for an hour. If you really need me, just send a text,” and then you shut off Slack, you shut off Zoom, you shut off all the distractions, and you get something done. So, remote can be extremely great for focus time, kind of Zen mode, when you need to. The biggest thing, though, is, like, people can’t look in your office and see that your head’s down working on something. You do need to let people know in Slack, “Hey, I’m going to be gone for x amount of time.”

Jonathan Yeah. So, you just kind of give a present status and this is what to expect.

Jamon We have a roll call channel and we just post in there, “Hey, everybody. I’m here.” And then, “Oh, I am going away for a little bit,” that sort of thing, and it’s really helpful.

Jonathan So, this next question, this is one of the things that has affected me, and I’ve shared with a number of people online before that. I have some pretty significant hearing loss, and working remote has really helped me in a lot of ways, in that I can use headphones to manage the volume on calls, and I’m actually able to hear a lot better than I am in person, which surprises me when I go into an office and keep asking people to repeat things. But for you, is there a condition or a disability or some type of situation like that that remote working really assists or helps you to overcome or improve?

Jamon Yeah, you bet. So, Jonathan, you had let me know that you’d be asking this question, so I asked my wife if I could share a little bit...something a little more personal, and she said totally that I could. My wife has clinical depression, and one of the great things about being able to work from home is that I’m around, and it really helps her ability to manage that condition. She’s able to... Even if maybe I’m not helping her out or engaging in whatever she’s doing, she knows that I’m around, and that’s a really awesome thing for managing... You know, when I’d work from an office, she’d often say, “Hey, when are you going to be home? I really like having you around.” And obviously, sometimes I couldn’t tear myself away. I had things to do, and that was tough. But now that I’m working from home, that really has... You definitely notice the difference. She really enjoys it and it helps overall her condition, what she’s dealing with.

Jonathan Yeah. There was a period in my life where I struggled with depression, too, and for one portion of it, I was working from home, too. And I think it was a similar situation for me, just reversed in that my wife was there. But being able to provide support for each other was a huge benefit.

Jamon Yeah. Totally. It makes such a difference. Even when I don’t really feel like I’m doing anything, I’m just kind of here working, you know. But for her, she knows I’m there, and that makes a difference.

Ari So, looking more at the long term, you’re running a country, or part of running a company, but do you see long-term that you would continue to focus on just working remote work if, say, you were to move on from Infinite Red or not? But whether you would stick with that, or whether you would want to go back at any point to actually working onsite or commuting or whatever it would be to actually regularly to an office again?

Jamon Yeah. So, I would say that my exit plan from Infinite Red is going to be feet first. I don’t intend to go anywhere. But obviously you never know, and I would say that I would only take a commute job, as I call them now, I would only take one of those types of jobs if there really were other options, and I know that there are other options out there right now for me. So, I’m 99% sure that I will be working remotely for the rest of my career, for sure. It’s too big of benefits. There are downsides, and you have to work around those, but the benefits are way too big for me.

Jonathan So, thanks so much for this interview and just opening up with us and this conversation. So, if people want to find you online and connect with you, where should they go?

Jamon You can find me on Twitter, @JamonHolmgren, and you can also look me up on Facebook. I don’t mind. I’m not super private about my Facebook stuff, so you can friend me on there. I’m totally cool with that. GitHub, JamonHolmgren, and then also, of course, my company website, infinite.red. So, feel free to just connect up with me. I love connecting with new people. It’s been a huge benefit to me, being able to connect up with other people around the world.

Ari Excellent. Thank you so much.

Jamon Yeah. Thanks a lot for having me on. Appreciate it. It was a lot of fun.