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How to Be a Remote Executive: Liam Martin of Time Doctor

2022-04-2262 min readWritten by Arc Team
time doctor liam martin remote exec
Written by Arc Team
Summary:

Liam Martin, CMO of Time Doctor and organizer of Running Remote, shared how to grow from “entrepreneur” to “executive.”

The first time you do something, you should not process document it. The second time that you do the same thing, you should think about how you’re going to process document it. And then the third time you should do it.

This week on the show, we have Liam Martin, co-founder and Chief Marketing Officer of Time Doctor and Staff.com. He is also the co-organizer of the Running Remote conference, the biggest conference on distributed teams and remote work.

Liam shares his insights on growing into an “executive” role by “letting the entrepreneur inside you die,” how to help other people work with you, and the literal million-dollar mistakes that Liam and his co-founder Rob made when running their company.

We also talk about why he started the Running Remote conference, the unspoken truths about running a large scale event, and what’s in store for next year’s conference in Austin, Texas.

If you want to learn from the best of remote leaders, you can buy early bird tickets for next year’s Running Remote Conference here!

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The podcast is also available on your favourite players: iTunes, Google Podcast, Castro, Overcast, Spotify, Stitcher, Player.fm, and Tune In.

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Topics also covered on the podcast episode:

  • 04:10 — How Liam realized that overworking and hustle culture is dangerous
  • 09:00 — The main difference between “entrepreneur” and “executive”
  • 14:15 — The top two things that Liam needed to re-teach himself to be a better remote executive
  • 24:14 — The million-dollar mistakes that Liam and his co-founder made
  • 30:17 — Why it is crucial to extract the “sacred knowledge” of your key team members and document it
  • 37:14 — How Liam created a document to help his direct reports work with him more effectively
  • 41:39 — The most surprising feedback Liam received from his direct reports
  • 44:45 — Why Liam and the team started Running Remote
  • 48:37 — The unspoken difficulties about running a conference

Mentioned resources:

Full transcript:

Jovian: Hello, world. Welcome to another episode of “Outside the Valley,” the podcast where we interview remote startup leaders, remote work advocates, and CEOs of distributed teams who thrive outside of Silicon Valley. They share insight on what works and what doesn’t so you can learn to do it right. This show is brought to you by Arc, the remote hiring platform that helps you hire remote software engineers and teams easily. I’m your host Jovian Gautama.

Now, this week on the show, we have Liam Martin, co-founder and CMO of Time Doctor and staff.com. Liam is also the co-organizer of Running Remote Conference, the biggest conference on distributed teams and remote work. Now, in this episode, Liam shares his insights and experience on growing into an executive role by, here’s what he said about it, “By letting the entrepreneur inside you die.”

We also talked about having a special document to help your direct reports work with you better and the literal million-dollar mistake that Liam and his co-founder, Rob, made when running their company. We also talked about why he started Running Remote Conference, the unspoken truth about running a large scale offline event, and what’s in store for next year’s conference in Austin, Texas.

So I went to the 2019 Running Remote Conference. It’s an absolutely great event to learn from and network with the thought leaders of remote companies and other remote workers. Early bird tickets for next year’s Running Remote Conference is still available. You can find the link on the show notes. Now, without further ado, here is Liam Martin. Here we go. Hey, Liam. Welcome to the show.

Liam: Thanks for having me.

Jovian: Yeah, Liam. It’s really great having you here. I was in the Running Remote Conference with my CEO and Head of Marketing this year. It was a great conference, and I’d love to talk more about that later on. But just to kick things off, can you share a bit more about you and your background?

Liam: Sure. So, human being located on planet Earth, more specifically, I’m located in the Canadian part of planet Earth. Even more specifically, in the French Canadian part of Canada. I am 37 years old. I run two tech companies, or I co-founded to tech companies, timedoctor.com and staff.com with triple tools to be able to facilitate remote work and make remote employees more productive. And then we also, as you had mentioned, are organizing a conference called Running Remote, which is the largest conference on building and scaling remote teams. We did the last two in Bali, which were very nice. This next year we’re going to be going to Austin, Texas, which I’m quite excited about.

Jovian: You mentioned that you are running two companies, you’re also co-organizing this Running Remote Conference. So when I was doing research about you, you wrote something or you mentioned there was a time in your life where you were like super stressed out in running a company working 12 to 15 hours a day. And can you share a bit more about this period? I personally want to know because this is usually…a lot of people find liberation in remote work, you know, when they’re busy with their company and time, they just find this…the possibility to work remotely is super liberating. So I think that’s kind of the same that happens to you. I’d love to learn more about what happened back then.

Liam: Do you know of the Japanese phenomenon/word called “karoshi”?

Jovian: Oh, yeah. It’s overwork.

Liam: Yeah. Basically, it’s death caused by overwork. And so, I was on a classical kind of karoshi trajectory. I was working 12 to 15 hours a day. As you had mentioned, things were not going great. I remember it came to a climax for me where I had ended up chipping one of my back teeth, my molars, and I went into the dentist’s office. And so, you know, when you go to the dentist, you sit down on the big chair, and they bring the big light up to your mouth and you can’t really see anything.

And I remember my dentist gasped, and it’s never a good idea when a healthcare professional gasps when they’re looking at you. And he literally said, “Liam, which tooth are talking about because you’ve literally chipped all of your teeth?” He thought that I had pancreatic cancer. Because supposedly pancreatic cancer is one of the only things that will produce this type of result. But it was not pancreatic cancer. It was just from me stressing so much and grinding my teeth at night. So I was literally grinding my teeth apart.

And so my dentist and therapist both told me I need to figure out something else to do or I am going to be in serious trouble. I will not be able to survive. I was 27 or 28 at the time, I believe. So pretty significant for a 28-year-old to be losing all of his teeth. And yeah, so

I realized that I needed to really kind of change my lifestyle and focus on, what are the core components of productive work as opposed to being busy?

So there’s a big difference between being busy and being productive. And that was the big differentiator for me, which was…and probably a lot of people that are listening to this podcast right now, they think to themselves, “Well, man, if I could only put in an extra two hours of work, I would do X, Y, Z. I would be able to do this thing or that thing.” But in the vast majority of cases, and I have the data to be able to back it up, those extra two hours probably will not produce more results.

And, in some cases, it may actually reduce your overall output, which is somewhat counterintuitive, but is very true when you look at the data. So kind of boiling it down to that, I mean, for me, it was a…

You can create any type of business to completely destroy your life. Just because you have a couple zeros in your bank account doesn’t necessarily mean that you are going to be a healthy and happy long-term person.

And that’s really what I think I want to be able to communicate to everyone is you don’t need to work hard, you need to work smart. And there is actually a lot of, like, we see in just kind of like today’s culture, kind of like the hustle culture, right, like, “Put in your 12 hour days, put in your 15 hour days.” I mean, they’re wrong. I can very clearly show them that that is not the way to be able to build a business. It boils down, unfortunately, to intelligence and opportunity. Those are really the two things that an entrepreneur needs.

Jovian: And that is a, I don’t want to say a sad story, but it is, like a moment of awakening. So after that, what did you do? Like when did you realize that finally, it comes to, “Hey, I actually can work productively and smartly and taking care of myself and build a business with a remote team?” So when did all of these click?

Liam: The first thing that I really needed to learn, and this was basically my transition from an entrepreneur to an executive. So I think about entrepreneurship is really zero-to-one. If anyone has read Peter Thiel’s “Zero to One,” it’s a fantastic book on understanding the theoretical framework for building a startup, any type of startup actually, tech or otherwise. And then being an executive is taking that one and turning it into 100. And those are actually two completely different skillsets.

So in the zero-to-one perspective, you have to be the person that understands all of these different pieces and puts it into your head. So you have to understand the marketing, the sales, the software development. You have to understand customer success, all of these different variables and then be able to come to a product that someone actually wants to buy. You need to convince that first customer to buy something, then you need to convince them to stay.

These are all things that you need to do in that zero-to-one process. In the executive stage of your life, you need to actually give up all of those things. So you need to start delegating those responsibilities to different basically leaders inside of your organization, and you have to trust that they know what they’re doing and that you can monitor that without really…

I mean, we can get into a little bit deeper of kind of like the different measures that at least we deploy in trying to understand whether or not someone is doing a good job and what course corrections we can give them earlier on so that they’re not moving in a negative direction. But fundamentally, you’re just saying you’re flying the plane and, you know, and I’m stepping back. And that’s quite scary, particularly for entrepreneurial personality types, which are generally quite egotistical. There’s the predisposition towards sociopathy in entrepreneurship.

It’s like, the data’s very clear. They are control freaks that like to talk about themselves constantly. So that’s you if you’re listening to this, and you’re thinking to yourself, “Okay, well, yeah. I am egotistical, and I like to talk about myself all the time.” Kind of almost like, and I don’t want to kind of hack on this for the American audience, but Trump is the absolute pinnacle of what that would be. So when you think of Trump, that’s the avatar of like, that’s the ideal entrepreneurial mindset, okay? And you need to have a component of that. I’m not like Trump, but maybe I have about 5% of that type of personality type inside of me, which is what has made me successful as an entrepreneur.

I just was watching CNN before I jumped on with you, you know, and Trump was like, “Yeah, everything’s great, no quid pro quo. None of this is happening and you’re all idiots if you believe it.” Right. And he just believes it. He’s just like, “Listen, it’s awesome. Everything’s going to be great, and there’s no issue here. This is going to happen, no worries. There’s no problem whatsoever. We’re going to succeed.”

Being an executive is a different thing. It’s almost the polar opposite. It’s like:

“Well, what is the problem? How can we solve the problem? Let’s reduce everyone’s expectations inside of the organization internally, and then let’s really try to figure out, how can we build a scalable organization long term?”

So that’s the big lesson. Difference between entrepreneurship and being an executive, two different things. My transfer took a very long time.

Jovian: Yeah. I really liked that you mentioned about this thing particularly because, first of all, I think this is super relevant for startups and companies everywhere, either you are remote companies or not. And second of all, it’s especially relevant to remote companies because it’s literally related to delegating and giving cross, right. And your example, I actually find Donald Trump as an apt comparison, not in a political sense, but in the fact that this is someone that do everything alone, like have less trust in anyone…

Liam: He’s a hustler.

Jovian: Yeah. And this is the same thing that I talked about with Mark Faggiano, the CEO of TaxJar in the very first episode of this podcast. So, TaxJar is like a hundred plus company right now. And he specifically mentioned about that growing pains when you have to realize that you need to trust people more and delegate people more and everything is slower. It’s not as fast as you want because you cannot do it yourself, right. So this transition, I really like how you frame it from entrepreneurial to executive. But for you, specifically, what were the most painful period of that transition? Is there any deliberate thing that you taught yourself?

Liam: So number one, one of the things that you’ll be able to kind of look at, there’s a phenomenon called the “Dunbar’s Number”. So Dunbar is an evolutionary anthropologist who saw the maximum amount of people that you can know personally. And he said it’s, at minimum, 100, and at maximum 150. So, the Dunbar number is basically 150. So if you are around the 100 person mark, and you’re moving towards a 150, you are basically surpassing the Dunbar number. And, therefore, you are forced to be an executive.

Don’t suggest that you will be able to know everyone, you know, by their first name as an example and know all of their history. So you need to kind of let go of that. I know when we were around 30 or 40 people, I knew everybody in the company. I knew them by first name. I was able to chat with them, you know, maybe once a month, realistically, through a Zoom call as an example. Now I can’t do that, and I have people that I personally manage and then those people manage other people.

Now, in terms of just becoming an executive, I would say the first…I would say probably it actually boils down to two big pieces.

Number one, you cannot do the hiring personally. So, you need to actually build a really solid HR and recruitment team inside of your organization.

So we have people…our director of HR understands the soul of the company and understands who is the right culture fit for us and who isn’t. So we hire almost entirely based off culture.

So before we see a resume, we actually do a culture fit interview before we even know whether they’re qualified. And someone could be the absolute perfectly qualified candidate, but we’ve found, long term, that hiring the perfectly qualified candidate that doesn’t fit inside of our company culture will end up in failure anyways. So, we just don’t even tempt ourselves with that. We just say, “We don’t even want to look at your resume. We just want to look at what your culture fit is.”

And then the second thing is building operational processes inside of your organization. So that’s a particularly relevant component for remote teams. Because, you know, if I was in your office right now, and I was a new recruit, and I was trying to figure out how to do something, I could just turn to you and say, “Hey, how do I do this?” But we’re remote, right? You’re in Taiwan, I’m in Canada, and we are way…you know, we’re worlds away.

How do we actually communicate that type of knowledge? Well, process documentation. So basically that means recording everything that is written down. I’m sorry, recording everything that you do in the company, writing it down, digitizing it, and then making it shareable across wherever you want to go.

So Google docs is a really good place to start. We use Trainual, who was actually at Running Remote last year.

They’re a fantastic product to really kind of take all of those repositories and put them in one place. Another suggestion that I would make to people is if you go to about.gitlab.com/handbook, GitLab is a remote-first company. They have 1,000 remote employees, and they have a 3,200-page handbook on how they run their business. So everything that you could possibly know about GitLab is there, and it’s entirely open-source. And, you can actually fork that Git repository.

You can build your own, and then you can just edit it for your own purposes. So, it’s a really great place to start. Doing processes is like doing your taxes, no one really wants to do it, so this gives you 90% of that framework and just edit it a little bit. So Dimitri, if you go to the YouTube channel, you know, he encourages people to actually steal his handbook because he thinks that that’s really gonna help remote companies, you know, get to the next level.

Jovian: So, for the listeners, you probably cannot see it because it’s an audio-only podcast. But Liam, I’m just nodding like a bobblehead about for everything you say. Because the thing you said about hiring process, basically, you know, things that come up over and over again in my interviews with other remote startup leaders because that basically the boils down to those two. Like, you have to spend the energy, the time, and the effort to create great processes and hire a worker.

Liam: Well, and let me get a little bit more specific on that. Because I think if you’re thinking about entrepreneurship, this is actually one of the biggest problems that an entrepreneur mindset will not understand and an executive will. When you’re an entrepreneur, you are doing everything on your own. So you’re doing all of these things. You are touching all of these things. You are like the archetypal micromanager, right? Even if you have people in your company, you’re basically still kind of like really directly overseeing what they’re doing.

An executive, however, the person that you’re hiring is entirely responsible for that domain. So if you hire a customer success manager, and you’re going to be able to build that as customer success department, and you have five or six customer success reps underneath them, you cannot understand the details of that department to anywhere near as well as the customer success manager. And, you must be able to give up that responsibility in order to succeed. However, entrepreneurs very rarely want to give up that responsibility.

So you can either be what I kind of call like a starter or like a zero-to-one guy that can take a company from, let’s say, like 0 to like $1 million, $2 million ARR within a year, you’re talking about the SaaS world, or you can be someone that is executive that goes from that $2 million to $10 million to $20 million level. Now, the actual $2 million to $10 million to $20 million level is way more complicated than the first stage, so it’s actually a lot easier to build $1 million business today than it is to build a $20 million business today.

But if you want to be both, you’ve got to basically let the entrepreneur die, unfortunately, which is very, very difficult for people. Giving up complete control and just saying, “Hey, you drive.” I’m bringing up customer success because I just hired a customer success manager, and I’m getting all of these different reports from different departments saying, “Hey, she’s doing this, and she’s doing that, and she’s doing that.” And I’m just saying, “Well, she’s in charge of customer success so talk to her about it. It’s not my responsibility.” Right?

And then you basically need to be able to create very clear measures for success or failure for that particular individual. So you’re basically, at this point, no longer…you are no longer doing any of the work inside of the organization. Your job is to measure the success of the direct reports that report to you

[…] which is really like… Yeah, it took me years to really figure this out, and I don’t really know even if I’ve completely figured it out at this point.

Like with Running Remote as an example, you know, we’re relatively small team. Igor is in charge of running that entire conference from beginning to end. I think there’s about four or five people on that team, but I still jump into the perspective of micromanaging, right? Being able to say, “Hey, well, you know what? I think that we should be using Tito, which is a ticketing app that we’re deploying this year instead of building our own ticketing system.

Because building our ticketing system is way too complicated, and I don’t want to put the dev hours into building it, and it will fall apart anyways.” And then Igor directly disagrees. We have a discussion about it, and I feel right, but maybe I’m not right because I don’t know the situation on the ground. That’s a perfect example of a failure of an executive because I’m pulling myself back into entrepreneur mode.

Jovian: I absolutely agree with everything you said, and thank you so much for being candid with the real-life example that you shared. I also want to add like the executive role, when it comes to remote [inaudible 00:23:16] even like the importance it has is amplified because you literally cannot talk to your executive like face to face. The difficulty of being an executive is just a bit more with remote teams. So, again, this is fantastic. I can talk about this for days. By the way how big is your team now? How many people are in your team now?

Liam: We’ve got about 100 people in the team, so we’re just entering that Dunbar number that I had mentioned earlier, and it’s definitely scary. So I used to really try to know everyone on a personal level, and now I know that that’s not what I should be doing because it’s just physically impossible for my brain to understand those many people at one time.

Jovian: Right. So, your team is going to like 100 is really a big number, right? And what were the mistakes you’ve made as a leader of a distributed team? It can be like process-related or human interaction related that you made, and how did it change your leadership style?

Liam: So I think one of the biggest problems that we had was me and Rob, my co-founder for Time Doctor, we are both nontechnical founders. And that was…we made a lot of mistakes inside of the software that we should have solved much earlier on. So about a year ago approximately, we had…the software was down for two days. And for a time-tracking product, that’s a really big problem.

And we lost about a million in ARR, annual recurring revenue, from that downtime. And, you know, we tried to apologize to customers as much as humanly possible, but, you know, if the product isn’t working properly, customers should be able to leave.

That’s the beauty of SaaS is if at any point you’re not happy, you can go. And it creates a really good relationship between the customer and the product because if the product isn’t, you know, doing what it should be doing, the customer can leave.

And then, in exchange, the company ends up getting really reliable revenue from all of the customers. So, yeah, we lost a lot of money on that. And we’ve completely rebuilt our tech stack from the ground up, which took us out of the game for 6 to 12 months. We have not shipped anything new for 12 months, right? We basically just kind of completely rebuild the software from the ground up. And now we’re at a point where we can just start building new features, but technological debt.

If I had to kind of boil it down to one singular thing that we should have done that we did not do is we should have paid our tech debt, and we did not. And so that’s a big one.

Secondarily, I would say getting really good coaches and mentors in earlier on. So, me and my co-founder are very different in our personality types. I like to talk to people to get answers, and Rob likes to read. So he likes to get his information from like blogs, and podcasts, and these types of things whereas I like to talk to real people. And two different approaches, don’t know which one is correct, but I know that I like doing the human thing and he doesn’t.

So that’s another example of something that I would have probably changed very early on is I would have built a much more hybridized model of the way that we pull in information and we process information. Because me and Rob are coming from very different places, which is actually good, but we needed to make it a lot more equal. And it would usually end up being kind of an issue of conflict because he would read a blog post about customer success and he would say, “Here’s how you do it.” And then I would go in and talk to five customer success managers, and I would get a completely different perspective.

So that’s an example of how we would be making very critical decisions based off of that, and that would end up resulting in conflict. But yeah, tech debt, it’s real. You don’t think that you have to pay it off. And it’s kind of almost like playing Russian Roulette. Because you can just say…I remember about three months before our horrible collapse I sat around the room in one of our team retreats, and I said, “So it looks like we’re not stable. We’re getting too many customers in, and we’re having stability issues, where are we at?”

And I was guaranteed that we were going to be stable for the next year. And three months later, we went down for two days. You know, it was one of those things like we fire up 1% of the servers, and they just get overloaded instantly. Like it was basically like our own internal denial of service attack because everyone was trying to log in all the time.

Jovian: Yeah. This is super critical when it comes to remote work, especially when it comes to technical debt and communication debt. So, you know, before I started the whole podcast, I asked our Director of Engineering, you know, just casual chat. I asked him, like, “What do you want to know about 100% distributed engineering team?” Because we are actually like a hybrid team, like half co-located and half remote.

One of his curiosity is that, how do 100% distributed team manage communication debt? So when you don’t have a good process established, there’ll be some kind of a time lag or a communication lag, which sometimes when you do 100% distributed team, it always happens, but you need to minimize that by having a great process.

Actually, I talked to the VP of Engineering of Help Scout, Megan Chinburg, a while ago, and she said that there’s always be time lag, but you have to have remote-first mindset, and you have to minimize those errors and try to not, you know, putting fires out all the time. It has to be a call. So I was thinking like in the situation where you don’t have a great communication process within your engineering team and this technical debt issue happens, that it’s really, really, really scary honestly. Because probably when the system is down and then you don’t really know what’s next, that is super scary, actually.

Liam: Yap. Well, so I think that brings up the argument of asynchronous versus synchronous communication and basically the two philosophies that are now in remote work. And it was one of the last debates that we had at last year’s Running Remote with the CEO of Help Scout and the CEO of Doist, Amir, the Todoist task-management app. So Amir also runs a competitive product called Twist to Slack.

And pretty much everybody probably knows what Slack is, but Twist is like Slack, but it is designed from an asynchronous mindset as opposed to a synchronous mindset. And even when we’ve looked at the failure of this two-day collapse that we had inside of Time Doctor, one of the very interesting situations that was happening is our server admin guy was getting on a plane for a nine-hour flight to Tokyo. So the system went down, and then within an hour, he was on a plane. And, he was in Tokyo, so he had no access to the internet during that time.

And when he had landed, he actually had said, “Everyone, don’t touch this because you’ve broken it more than you fixed it.”

So it really reinforced what I like to call sacred knowledge inside of the organization, which you should try to get out of your organization as quickly as humanly possible. So if there’s only a singular person that can do a singular task, that is a failure point that can destroy your business. So you need to constantly audit your organization and say to yourself, “Where is their sacred knowledge?”

So I’ll give you another example. Rob, my co-founder, who is the CEO of the company, has a Google doc, and the Google doc is sent to me and our product manager. And the password is given to his wife and to one other person that we don’t even know. And if he were in a car accident or something like that, or, you know, if he’s dead, or if he’s brain dead, then like, you know, what are all the passwords, access points, all that kind of stuff that we would need to be able to get access to?

And that kind of came up based off of our auditing of where is that sacred knowledge located, and how can we unlock it? And there’s some sacred knowledge, like, as an example, that Rob has in his head that he doesn’t want other people to know in the organization. But he needs to make sure that he’s written it down somewhere so that if he is gone, there might be…you know, we can grab that information. So, yeah, sacred knowledge, super important inside of remote organizations.

In terms of just communication sync, I would say asynchronous makes happier employees. Synchronous makes faster-moving companies.

So, you need to be able to measure your priorities based off of that perspective. I have a hierarchy of communication, which is basically in-person beats video, video beats audio, audio beats instant messaging, instant messaging beats email.

So if I’ve sent 10 instant messages back and forth through Slack as an example about a particular issue and we haven’t solved the problem, I try to push it to a phone call as quickly as humanly possible, preferably a video phone call so that we can really work out the nonverbal communication that might be occurring on a video call versus audio call.

We’re doing this on a video call right now. I can see you, you can see me. You know, if there’s questions that you ask me that maybe I don’t feel comfortable with, you might not be able to see that through audio, but you would be able to see it through video and maybe you would redirect that conversation somewhere else.

So once you have all of that synced up and you know how your communication works, then you want to take all of that communication that’s currently happening, and you want to try to pull it into process documentation as much as possible. So once something really should turn into a process, I have the…basically, my perspective is the rule of three.

The first time you do something, you should not process document it. The second time that you do the same thing, you should think about how you’re going to process document it. And then the third time you should do it.

The reason why is on the hundredth time, you forget all the small details connected to that particular process. And then on the first time, of course, you’re not actually going to be able to know what you’re doing. So the third time is usually a pretty good time to kind of process document that type of thing, put it in Trainual, put it in a Google Doc, put it in GitLab, and then just it’s there. And if someone wants to query it at some point, they can.

Jovian: This is a great approach when it comes to documenting. I really love the three steps. So, I also talked to the founder of, you remember Remo? They’re also the…

Liam: Ho Yin.

Jovian: Yeah, Ho Yin. I talked to Ho Yin our podcast. So he has a really smart approach. Okay, for our listeners, if this is the first time you’re listening to this podcast, okay, listen to this because it’s really smart. Okay. So he’s actually still on the verge of transitioning from entrepreneur to executive. Like, he wants to. I think he will be really good at it because he really likes reading processes and stuff. But there’s one hack that he does to kill two birds with one stone. So basically, when he does something, for example, creating a zap using Zapier, the tool Zapier, right, he will record it, and he will talk over it.

Like, “Basically this is what I do next, blah blah blah.” And then he’ll pass it to his team member, and that person will do the task and document it. So basically it saves time of the CEO, or CMO, and whatnot, and he’s using it…he’s teaching it, and it’s pretty easy, right, when you talk like you mentioned. For us like to hash things out, it’s easier through a video call. But he does that, and he pass it to someone, “Hey, please create the written documentation for this.” So that sacred knowledge there is out forever. I think this is super smart. I told this story a couple of times in our episodes. So if you’re listening to this and to figure out, just try it. It’s really good.

Liam: We use a tool called Jing for that, which is really great. It’s a little tiny kind of like orange circle at the top right-hand corner of my screen. And at any point I click that, and it creates a five-minute video that turns into a Bitly link.

Jovian: Oh, that’s interesting.

Liam: It instantly uploads, right? So the moment that you’ve completed the video, it just uploads. And then you’ve got that as a Bitly link, and then you can put that inside of a process doc. There’s a bunch of apps out there just like Jing.

Jovian: Yeah. So, right. So I think this is a good segue, like the whole written documentation thing, this is a good segue for this one thing I want to ask you about so-called Liam’s operating manual. Yeah, so I heard you mentioned this on your other interview on “The Pesto Podcast,” so I’d love to dive a bit into this, right? So I’ve heard about this concept a couple of times, but I’d love to hear from you, like how does this work on your side?

Liam: Yeah. So, the document is called “Blueprint to Liam and His Weird Little Quirks,” and it is a one-page document. And it has eight tenants of who I am as a person. So, as an example, like I am an ENTP, which is inspired innovator motivated to find new solutions to intellectually challenging problems. ENTPs enjoy playing with ideas and especially like to banter with others.

Jovian: This is the Myers-Briggs test, yeah?

Liam: This is the Myers-Briggs test. So I said, “Google ENTP personality types to learn more about me.” The second tenant is decide.

Decisions over options is always my preferred way of working. If you have to bring me options, tell me which one you’re leaning towards. If you aren’t leaning towards an option, then you haven’t thought about it long enough.

So these are just very direct ways of me communicating who I am as a person and not necessarily communicating the positive aspects of me as a person.

And that’s really important to be able to mention for a direct report. So this document goes to anyone that is directly reporting to me, and I give them that document. And it came from me talking to three of my closest friends and saying, “Could you tell me what you would say to someone that’s just about to work for me on how to make sure that they can get the most out of me as a manager. And be very honest?”

And you need your friends who will actually tell you that you’re full of shit if you are full of shit. Like, you need to be no, as an example. I don’t really like people giving me qualitative answers to problems. So, if you say, you know, “We should build this feature.” “Why?” “Well, because I think it’s a good idea.” Wrong answer for me. That’s a really bad way to communicate with me. What you should be saying is, “There are these 17 customers that represent 1,428 seats that represent this much revenue that want this feature. Here’s the documentation for it inside of intercom as an example. This is what we should be doing next.” That’s the way that I usually like to be worked with.

I have a thesis statement at the very end of this document, which is, “I value decision-making above all else. I’d rather you make the wrong decision than none at all.” And that’s actually a really difficult thing for a lot of employees to be able to get their heads around, so it’s just the way that I like to work. And so it’s just my particular kind of working style. I have a…my general mindset is, don’t ask me what to do, tell me what you did. If you’re asking me what to do, you’re out.

Jovian: Yeah, I think it’s good. This document gives clarity. Do you update this document from time to time or does your direct report sometimes update it? Does it make sense? Probably they said, “Hey, I think I want to add this.”

Liam: Yeah, we’ve thought about it. The first time that I did this exercise, it took me a couple of days. And I literally just had a couple friends of mine out for drinks and was just like writing stuff. And a lot of this stuff in this exercise, it’s going to be very difficult for you, particularly if you’re an entrepreneurial type, egotistical, somewhat predisposed to sociopathic behavior, these types of things, to take that feedback because you have to put your ego aside, right? Like, you have to be like, “Well, you know what? You’re a bit of an asshole because of X, Y, Z,” right? And it’s like, “Hmm, okay. Do you guys agree with that?” “Yup.” I put it in the document because that is upon.

Jovian: Right. What were the most surprising thing that is written there that you never thought about before?

Liam: I think it was…boy, what was the most surprising one?

Jovian: That make you think, “Oh, I didn’t know I was like this.”

Liam: You know, I’m a starter and I’m not a finisher. So what I mean by that is I’ll give you Running Remote as a perfect example. So Igor is a finisher, I’m a starter, which is actually a really good team to have. So when we first started Running Remote as an idea, I said, “Okay, well, let’s just see what happens. Let’s throw this website up and see whether or not anyone wants to buy tickets.”

And Igor, and he’s definitely evolved past this point, but he said, “Well, you know, what do you mean? We’ve got to pay…we’ve got to get like $20,000 together to be able to build the website and put together the ticketing system, and blah, blah, blah, and all that kind of stuff.” And then within about three hours, I bought the domain. Our AWS server was too slow because I needed access. I just got to a GoDaddy server, and I put together…I bought a $20 WordPress theme, which is actually the same general design that we use today. It’s the same framework.

And then I put up a…what’s the ticketing system that everyone uses right now? Some kind of general ticketing system that I could get off the shelf instantaneously. And I put it all together. I put up some speakers that I knew that already said yes, and then put it up, and I said, “Okay, website’s done. Let’s run some traffic to it.” That’s an example of a starter. But in terms of getting the small details oriented, in terms of like figuring out, “Well, let’s negotiate with the AV company.

Do we need this extra monitor? Do we need this extra camera? You know, how do we do the post-production? All those types of things. That is very difficult for me to do. It doesn’t excite me, and it drags on whereas someone like Igor really likes that type of work. So that was the difference, the difference between being a starter and a finisher. I thought maybe I was a finisher, I wasn’t a finisher. I was definitely a starter.

Jovian: Yeah. I can see how that feedback can be surprising or probably even hurtful, especially when you’re entrepreneur type. Like, if people say to you, probably not the exact word, you’re a starter, but you’re not a finisher. Especially if you’re an entrepreneur that has been doing a lot of stuff solo in your whole career, it’s probably like, “What the fuck?”

Liam: Everyone’s gotta finish. Yeah, like every time gotta be a finisher when you’re an entrepreneur, and it’s like, “Yes, I did finish things.” I hated finishing things. It was like grinding my teeth, you know, all the time. It was really difficult for me, so don’t do that. You know, just focus on being the starter. That’s going to be a lot better for you.

Jovian: Awesome. So, Liam, I want to segue more. We’ve been talking about the whole Running Remote thing, so let’s just go down to the conference. Can you tell me a bit more, why did you start Running Remote in the first place? What was the goal?

Liam: So I had gone to a couple conferences that were supposedly about remote work, but they weren’t necessarily about remote work. They were about a phenomenon that probably if you’re in the remote workspace, you know about, which is called digital nomadism. And those are people that basically work from their laptops, and they constantly travel. So, yeah, it’s kind of like the “four-hour work week” mindset. By the way, that doesn’t exist at all. Show me one person that’s, like, working four hours a week and is making over $1 million a year, and I’ll show you a liar.

Jovian: Oh, yeah. I’m going to tag this to Tim Ferriss, by the way. I’m going to tag Tim Ferriss on this.

Liam: Sure. Yeah, go for it. There is no…that does not exist. I can guarantee you…

Jovian: Yeah. I think he also said that it doesn’t exist. I remember I was listening to his podcasts, he said like, “No, that’s not the point. The point is you have to work yourself until you get the point.” Anyway, I was like…

Liam: I mean, Tim Ferriss works 60 hours a week. He’s a workaholic. So, I mean, he’s not taking his own medicine frankly. So, went to all these conferences, and they really weren’t about what I wanted to learn about, which was, “Well, how do we go from 100 to 150 people? How do we build a customer support team? How do we build a development team that works? How do we get inspired by remote companies that are really at the forefront and scaling to, you know, extreme levels?

We had Mercy Murray from Shopify, Director of Support of Shopify that went from 0 to 2,000 [inaudible 00:46:30] You know, those are the thing that I really wanted to learn about. So I realized at that point that that’s what I wanted to do, and that conference didn’t exist anywhere else. So I spoke to a couple friends of mine. Amir actually was probably one of the people that really started the conference out and made it real because he said he would come and he would get a couple of his friends to come, which was great.

Jovian: Amir is the CEO of Doist?

Liam: Doist, yes. So he still today is our customer avatar. So if we are unsure about a particular speaker, we will ask Amir, “Would you like to see this person speak at Running Remote? “And if he says no, they’re out because we just follow that singular individual. In essence, what we’re trying to target is someone that’s maybe two to three years back from where Amir is right now. Amir is about a hundred people. So when Amir was at like 30 remote staff, that’s really the perfect founder.

Like, that’s the person that we want at the conference, someone who’s building a remote-first team or someone who’s interested in building a remote-first team and may have an on-premise team, an office team, at this point. That’s the archetypal customer. You’ll never have a talk about travel hacking, or how to build an Amazon FBA business, or anything like that. We’re really just focused on basically, “How do we build and scale remote teams?”

Jovian: Got it. And so, I was always amazed by how you guys manage to pull the whole event while you guys are 100% distributed team. So I believe it’s not an easy task to just do all of that with, you know, invite speakers, and arrange accommodations, and whatnot. As an organizer or co-organizer, what is the most difficult thing or the top two or three difficult things that you need to do to organize this offline event from all your [inaudible 00:48:40] Yeah.

Liam: Yeah. So I can kind of go into that in a little bit of a deeper way. I think I don’t have that much experience. We’ve only done two, and we’re doing our third one, so take that with a grain of salt. But there’s a lot of things that I didn’t know about running conferences that I now do know that are not written down anywhere because no one really wants to tell you that these are the real rules of the game. So there’s a black hole between 300 and 1,000 attendees, as an example. So up to 300 attendees, you can have a very profitable conference based just off of ticket sales, and you’re not really going to get those many sponsors.

Jovian: Interesting.

Liam: A thousand plus people, you will get really good sponsors, and you don’t really need to bother about generating significant amounts of revenue from your ticket sales. But in between 300 to 1,000 people, there’s a black hole because sponsors won’t give you the big bucks. They won’t pay 100 grand for a sponsorship, but then it’s also a little too big for people. A lot of the attendees will say, “Uh-uh, this is getting too big,” or, you know, “This is getting too big of an event,” that kind of a thing. It’s lacking the intimacy. So, you need to either above or below that hole as quickly as humanly possible. And so that’s where we’re currently at, which is actually really problematic.

Another thing that, you know, not many people tell you about is most revenue is coming from sponsors. It’s not coming from ticket sales. So the sponsors are the ones that are really the…each Running Remote ticket ended up costing us $980. So it costs us to sell you a ticket, cost us $980, and the ticket prices float, you know, early birds are like $500 up until about $1,000. So, actually, we only break even on the thousand dollar price point, and we lose money everywhere else.

But can we charge $1,500 to $2,000 for a ticket? Maybe not. You know, that that’s a little bit more of a significant ask for people. So that’s an interesting phenomenon where I didn’t know that this is the way it works. And, in reality, it is really making sure that you have some fantastic sponsors that are able to work with you and then getting fantastic customers for those sponsors to the conference.

That’s basically the game of running conferences. Outside of that, just a whole bunch of logistics. You know, we had, particularly in Bali, I remember the first year of Running Remote, we had had all these cars that were stationed around the conference area and around the speaker’s area, and I needed to get 20 speakers to the conference. And it was 8:30, and I believe we started at 9:30, and there were no cars. There were no drivers around.

They basically had forgotten about us as the speakers, which are really important people to get to the conference. So I ended up finding a bus, and I asked this guy that had the bus, I said, you know, “Can you take us 15 minutes this way to the event?” And he’s like, “Oh, no, no, no, no, no. We can’t…” Very Indonesian polite way of saying, “I’m sorry, I can’t.”

Jovian: Yes, definitely. Yeah.

Liam: There’s a very unique way of apologizing in Indonesia, which I can’t really recreate, but it’s got a certain flavor to it. And then I said, “Okay, how about $100 U.S.? And he’s like, “Get on.” And, literally, he stole the bus from his boss because he’s going to pick up 100 bucks, right, which is a big money in Indonesia. And so, we were able to… I basically stole a bus to be able to get the speakers to the event, and then, you know, he’s zipped back. And, supposedly, he got yelled at by his boss.

So those are examples of things that just like logistical nightmares. The very first session at Running Remote, we had the screen that was fuzzing out, and there was like this fuzzing out of the screen. And we found out we had done an entire year, or sorry, an entire day of work the day before, none of that problem presented itself. And then we realized that we were using the internal hotel’s power system for audio, but we were using our power systems for video. And there was an electromagnetic conflict between those two power sources, which was damaging the equipment and creating this kind of like a static in between those two sources.

And we had just flipped those power systems because we said to ourselves, “Oh, well, if we’re going to use, we should use the hotel’s power systems because they’re offering to give it to us for free.” These are examples of things that just like, they’re nightmares from a logistics perspective, but they’re going to happen. And I’ve just realized at this point that hiring really good professionals that have done, you know, 40 conferences before as an example, is the way to do it. Once you can afford it, do that. You know, we didn’t do that. Everything was run on our own.

And we also, another variable, which is interesting in Bali and Indonesia is me, I was working in the back, right? I did not have a work visa for Indonesia, so we were always terrified that someone from, you know, immigration was going to come in and shut us down, or, you know, ask everyone, “Are you all Indonesian citizens?” Or, “Do you have a work visa?” Those are the things that, you know, just sort of, you think about when you’re running a conference in a developing country.

Jovian: Yeah. I want to let you know, like as an Indonesian, we are pretty lax when it comes to that, apparently. Yeah. Especially the $100 hundred bus thing, that is very hilarious because, yap, that’s it. That’s the Indonesia I know. Yeah, I really can tell, like, we’re on a video call right now. I can tell from the expression that you’re literally, you’re basically, [inaudible 00:55:13] “I shit you not that these things happen,” but I just wanted to let you, like, almost like say, “Am I renting?”

But I just wanted to let you know that, as I mentioned before, I attended the Running Remote Conference in Bali this year. I think it is an amazing conference. Okay. The Running Remote conference this year is actually where I started pitching my podcasts to some of the people there. So I talked to Nick Francis actually, like, “Hey, do you want to be on my podcast?” And then when I followed with him, he basically recommended their VP of Engineering to talk. So that’s one.

So I made connections. Andrew Warner was there. Andrew Warner gave me an advice on how to start a podcast. Talked to Andreas Klinger, which had a killer keynote on the conference. And it’s on YouTube right now. Actually, I put it on the show notes for people to see again. I just wanted to…you guys did an amazing job, and I believe that you’ll do the same next year. So, I want to close it with the last question. I know you’re running out of time now. So you’ve been running this conference two years in a row now, right, and next year will be the third year. What are the most valuable things that you’ve learned from the speakers or just from interacting with the attendees?

Liam: I’ll tell you the thing that surprised me the most. So I’ve been able to interact with the absolute top of remote founders on planet Earth, right? Like Running Remote is the definitive place. If you’re a remote founder, you’re going to probably be there more than any other place on planet Earth. So it’s this really great opportunity where all of these thought leaders can come together and can, not only share best practices, but also talk about the future of remote work as well, which is very, very exciting. It’s a phenomenon that’s just exploding right now on planet Earth. And here’s the thing that blew me away.

When I actually sat down and asked them about their playbook, so, “How do you run a remote business? How do you run a remote business? How do you run a remote business?” They all gave me really different answers.

So one person would say, “Oh, video calling. It’s the only way that we should interact.” And then someone else would say, “No, video calling is really stupid. You shouldn’t be doing video calling. It’s a really inefficient use of your time.” Someone else would say, “You know what? It’s gotta be asynchronous communication. That is the only way that you can build a remote company.”

And then someone else is like, “No, you’ve only got to use synchronous communication. The more synchronous communication you have, the better.” So it was interesting to see such huge differences between all of these equally successful individuals.

And I came to an interesting conclusion, which is: because remote work is such a huge productivity boost in such an increase to people’s businesses, I actually think almost everyone is doing it wrong. And, it doesn’t matter if everyone’s doing it wrong because the overall productivity gains from being remote means it’s a net win.

So it’s going to be very exciting over the next three to five years, I believe, because hopefully, Running Remote and a bunch of other partners as well, we’ll be able to start to build that playbook and build best practices into an organization. So are video calls the way to do it? Who knows? Have we done some really good quantitative studies on this to be able to figure that out? Not yet. Team retreats, company retreats, do they increase productivity? We do them. Why do we do them?

Because Amir and Joel and a bunch of other people have done it, and we just think, “Oh, well, if they’ve done it, we should do it.” That’s the only reason why we’ve done it, and we like it. So it’s just like maybe that doesn’t produce a positive ROI at all. Maybe we’re just burning that cash. Who knows? You need to be able to start to do the work to be able to actually see what those results are.

So that’s what I’m really excited… What blew me away was no one knows what they’re doing. And what is also exciting me is that no one knows what they’re doing. Because as we know what to do, it’s going to be even better.

Jovian: Yeah. That is interesting. It’s also aligned with… So, I talked to Hiten Shah a while ago and his message basically, just, figure out what works for you and do it. So I want to share my learning. This one thing that surprised me that I actually never thought about before I attended Running Remote is the fact that remote work opens up possibilities for people around the world, no matter which country you are, especially people from a more unfortunate background, you know, with disabilities. So, in the beginning of the Running Remote Conference, you were the opening keynote speaker, and then you shared a video of this young gentleman, I think Faheem.

Liam: Faheem.

Jovian: Faheem. I think it’s Faheem, and he’s based in Bangladesh. And he has a disability and that video shares about how he is able to find remote jobs by doing designs online through a freelancing platform. And that actually struck me, [inaudible 01:01:15] “Oh, yeah, we’re talking about remote process as a company and, you know, how remote actually bring productivity.” But these are the thing that we actually never put a deep thought, like how remote work actually makes it, this sounds so cheesy, almost [inaudible 01:01:37] But, in a way, it does make a better world.

A couple of days ago, I read this article shared by Jennifer Aldrich, which is a community manager in InVision, about how when it comes to people with disabilities, remote work is not just a perk, it’s everything. It allows them to do their creative [inaudible 01:02:02] it allows them to feel empowered, and so on. So these are the one thing that I took away from the Running Remote that I will actually never forget. So, again, thank you for that.

Liam: That’s perfect.

I think that to me, remote work gives employers and employees the opportunity to find the best of each other.

And that’s something that is such a unique opportunity that has never existed before. So whether you’re in Bangladesh, Cairo, Toronto, or San Francisco, you’re going to be able to get access to the same work opportunities. And that’s never happened before.

That is the very unique opportunity that… We’ve been talking about “outsourcing and globalization,” but only in the last few years has that actually been a real reality where someone like Faheem, who has muscular dystrophy, that went from literally begging in the streets of Dhaka to being a very successful designer on Fiverr, which is the platform (and Upwork) that he works off of.

There are millions of Faheems all over the world, and they’re able to get access to these work opportunities and they just would not have been able to do it previously. So I had mentioned, at the end of my initial address, which was, the people in that room are really the drop in the ocean. But we’re creating ripple effects that we’ll be able to hopefully positively impact people like Faheem.

Jovian: Yeah, that’s amazing. This is also something that we tried to promote in our company in Arc because our mission is basically, we want to connect talented software developers no matter who you are with opportunities around the world. Because I remember Andreas Klinger also said that in his speech, like, “International talents deserve international compensation.”

So that’s [inaudible 01:04:04] So we really believe that, so that’s why we’re trying to do it in Arc. And hopefully, we can always get better at it day by day. All right. So, Liam, we’re near the end of the conversation. So where can people learn about you, about Running Remote online, and can you share a bit about the next Running Remote event?

Liam: Sure. So next Running Remote event is going to be in Austin, Texas. So it’s going to be just like Bali, except there’s going to be barbecue, which will be very nice. And, it’s going to be just like the other two Running Remotes, only bigger and better. So we are going to have Wade, who is the founder of Zapier. He’s going to be coming. We’ve got Lori McCleese, who is head of HR Automattic, which is the company that runs WordPress. They have about 1,500 remote employees. John Eckmann from 10up, massive agency, entirely remote.

Sara Sutton, who’s the founder of FlexJobs, a bunch of other fantastic speakers that are going to be coming as well. You can just go to the website to check it out. And, you know, that’s going to be that side of it. If you want to get in contact with me, one of the best places I believe that you could go is YouTube. So if you go to youtube.com/runningremote, there is going to be every…like, all of our talks are up for free. So if you can’t afford to come, you can come to youtube.com/runningremote, check it out. And if you put in a comment, it will actually be me. I’ll get back to you within about three to four hours.

Jovian: Amazing. And also, I just wanted to…you are probably the first human in the world that compares Austin to Bali. This is the most absurd comparison.

Liam: Yeah. We have got a little bit of pushback on Austin. We also realized connected to creating a bigger movement for a remote work, which is, if you’re not targeting the U.S. market, they’re currently the leaders right now. So we may be back to Bali in the future, but we’re going to do one in the United States to be able to activate the people in the U.S. And, yeah, I mean, Austin’s good. We got some pushback. And, to be honest with you, we’re getting to keep a little piece of Bali in Austin, so you’ll just have to come to the conference to be able to find out what that is.

Jovian: Right. That’s amazing. Oh, by the way, I think this place is excellent. It’s just the comparison that I find really bizarre. Anyway, so Liam, thank you so much for your time. I really enjoyed this conversation. And, it’s really nice to be able to tell you that part of the reason we like to podcast is because we are able to connect with great people in Running Remote Conference, and I wish you all the best for next year’s conference. Hopefully, I can be there. Let’s see.

Liam: Yeah, for sure. You should definitely come. Thanks for having me. And it’s really cool. I think that remote work is just one of those things that it’s incredibly exciting. And it’s not just kind of work perk, it’s a movement. It’s really starting to happen. So I’m very happy that you guys are in it as well and helping to spread the word.

Jovian: Yeah. Awesome. Again, Liam, thank you so much.

Liam: Thanks for having me.

Jovian: And that’s it for another episode of “Outside the Valley” brought to you by Arc. We created this podcast with the hope that in each episode, you can learn something new from other remote startup people. So if you have any feedback or suggestions, please don’t hesitate to reach out to me at jovian@arc.dev. It’s J-O-V-I-A-N@A-R-C.D-E-V. Or you can find us on Twitter @arcdotdev. See you next week with another episode of “Outside the Valley,” and ciao.

Blooper:

Jovian: Right. So if you want to swear, feel free.

Liam: F**k yes.

Jovian: And no one has ever sweared before, which is actually weird because I never say…

Liam: Oh, maybe I’ll be the first.

Jovian: …I never say that you cannot swear here. The words like sh*t, but it’s just like, eh.

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