Becoming a Digital Nomad Entrepreneur, with Jesse Chambers

Gabriela Molina

Jesse Chambers is an entrepreneur in the digital media space. He has accomplished executive with leadership experience at successful startups and respected global media brands. In 2019, he founded wrkfrce, a digital media company dedicated to remote work.

Jesse Chambers

Read the transcript

Luis:

Welcome, ladies and gentlemen, to another episode of the DistantJob Podcast. I am Luis, your host in this podcast that’s all about building and leading awesome remote teams. My guest today is Jesse Chambers, the Founder and CEO at wrkfrce. Jesse, welcome to the show.

Jesse Chambers:

Really glad to be here, Luis. It’s an honor. Thanks for having me.

Luis:

It’s an absolute pleasure having you. I’d like to begin by asking my usual startup question, which is how did you come to remote work and how did remote work influence your career trajectory?

Jesse Chambers:

Lately, it’s influenced it quite a bit as the founder of wrkfrce, but I’ll get to that. The origin story, Luis, doesn’t make me look terribly smart or bright. I actually very organically found myself as a remote worker. For the majority of my life and career for about two decades, I was living and working in San Francisco. In about 2017, 2018, my company was going through a series of mergers. I wasn’t sure if I was going to have a job on the other side of those mergers or if I was going to want the job that I had on the other side of those mergers. And so, I sort of engaged in an exercise. I said, “I’ve had a great run here. It might be time to move on to something else. What are the things that I really value and would really want in any job that I had regardless of the company?”

Jesse Chambers:

As I began that exercise, I actually realized that I was a remote worker. I was based in San Francisco, but my company had multiple offices in San Francisco. I had desks in two different buildings. My bosses were based in either New York or Denver, and my company was based in New York so I was spending one week per month in New York and then traveling to, nationally and internationally to conferences and offsite meetings and all that kind of thing. And so, when I was in San Francisco, if I needed to be in the office, I was in the office and if I didn’t need to be in the office, nobody was saying, “Hey, where’s Jesse.” And so, it was sort of this slap my forehead, aha moment where I said, “Man, I’m a remote worker and whatever it is that I want to do next, I don’t want to have to go back to a rigid 9:00 to 5:00 schedule.”

Jesse Chambers:

And so, armed with that sort of lens, I started to look around and say, “What other companies are out there that are working this way or what resources are there for people who want to work in this way?” and was very frustrated at the time to find very little out there for that. And so, I was frustrated for about 30 seconds and then I said, “Wait a minute, Jesse. You know a thing or two about building media brands, if this is something that you wish existed, maybe other people would too.” And so, that realization became the seed that has grown into wrkfrce, believe it or not.

Luis:

Nice, interesting. First of all, I don’t think you look unsmart at all. If you consider that, I came to remote work by working in the video game media space, so definitely, you’re coming up ahead for me. It does seem that you had a very nomadic, very busy lifestyle. How has that evolved over the time? Are you still traveling all around or how is the situation now?

Jesse Chambers:

Sure. Very much so and even more so actually. As I began the journey of founding wrkfrce, leaving my company, it actually ended up being the second scenario where I had a job in the other side of the merger, but it wasn’t the right job for me. And so, I was able to leave the company and begin the process of founding wrkfrce. Through that, two things. The first thing was that I quickly realized that being a bootstrap startup founder and paying for housing in the San Francisco Bay Area are not compatible propositions. And so, from a financial standpoint, I said, “I might have to rethink this.” Then, also, using the opportunity of founding a company that’s dedicated to remote work, to really walk the walk.

Jesse Chambers:

And so, in early 2019, my wife and I left our apartment in San Francisco, sold most of our belongings, and bought a 27-foot Airstream trailer. And so, for the last three plus years, we’ve been living the majority of our time traveling the U.S. in an RV before it was hit, before the pandemic made that cool. And so, in that time, we’ve visited 39 states. We’ve towed the trailer 35,000 miles plus, and we’ve spent the rest of the time living in different places too. We’re not 12 months in the RV. I’m right now in upstate New York, at my family’s lake house.

Jesse Chambers:

We’ve also spent time in Airbnbs in places like Mexico City and Playa del Carmen. You and I were talking before we started recording about Portugal and Porto and Lisbon, and places like Palm Springs. And so, we’ve really taken advantage of the opportunity that remote work and work from anywhere can afford us. For me, that’s been really beneficial because I can really walk a mile in the shoes of the wrkfrce audience and understand the challenges not only that remote workers have, but the challenges that managers who are trying to lead remote teams and builders who are trying to build companies remotely can really have, and that can give me a lot of empathy and also give me a lot of firsthand experience in terms of the content that we want to create and the kinds of solutions that we want to offer to our audience.

Luis:

That’s actually a very interesting point. Well, there are many things that I want to touch on that. Let’s actually start by the logistics. You are doing the great American road trip on your RV while trying to bootstrap a company. How do you sort your internet situation? Let’s start by that. How do you actually manage to keep abreast with communications and the news and et cetera while doing that? Because let me tell you, when I go to Germany, which is supposed to be a first world country, and I check in advance that the hotel has good internet, then I get there, and actually, even the 4G doesn’t work. That’s a challenge that we have in Germany. I’m wondering what happens when you’re in the U.S. in the middle of the desert.

Jesse Chambers:

Well, it’s not just in the middle of the desert, it’s a challenge in upstate New York. For example, the place that I’m at right now, my family’s lake house that we’ve owned for several decades, we didn’t, until September of last year, we only had DSL. The local was 1.5 megs per second. And so, we had to get very creative. Now, we have fiber 200 megs per second and I feel like I’m the king, but in general, that thing, that connectivity question is one that is central to the question of the ability to work remotely in the U.S., internationally, whether you’re in an RV or whether you’re in a community, in a city, or a small town. In the U.S. access to high speed broadband internet is something that somewhere on the order of 15 to 20 million people don’t have.

Jesse Chambers:

Actually, with our latest infrastructure bill, they’ve done about a $50-billion investment to solve that, but in the U.S., which people, I mean, you mentioned Germany, in the U.S., there’s 20 million people who don’t have access to data speeds above 20 megabits per second, which is, in my view, totally unacceptable and something that if we want to, as a country and as a culture globally, to really embrace the ability for people to work remotely and to start businesses and to be contributing to the new economy, we need to fix that. For me, very practically, to get to your actual question and get off my soapbox about rural internet is that we use cell signal, so everywhere we would go, we would have an AT&T or Verizon data plan and cell signal either from our phones or wired into the RV itself and try to pull down data signal.

Jesse Chambers:

And so, there are several apps that we could use where we would try to arrive in a place and understand what kind of signal access we would have, patching together different data plans, building in redundancy between having an AT&T plan and a Verizon plan and a T-Mobile plan, but essentially, that whole time for the last three years, it wasn’t always easy, but succeeded in founding and building a company and staying in touch in all those ways just using cell signal that was sometimes a challenge.

Jesse Chambers:

Sometimes, we would get to a place that was beautiful that we couldn’t wait to be. We would look at our phones and say, this isn’t going to work. We don’t have enough signal. We would have to move. Sometimes, we would be in places, for example, once we were in San Diego, a big city and we were less than a mile from the freeway, and we weren’t able to get enough data speeds to allow us to work. That’s something that is a real challenge. I think that there’s solutions like Starlink, which promise to close that gap a little bit and be an interesting alternative for people who are either living rural or people who are on the move in boats or RVs, but that’s still coming to market and still a bit of a question mark for some people, but it’s a real challenge, whether or not you’re in an RV or you could be in a big city and still have that challenge.

Luis:

I mean, I’m definitely a big Starlink hopeful. I think the concept is amazing. The concept could change the world, but as someone that’s been tracking it very closely, I do think that it’s still not ready for prime time. I mean, they recently announced Portugal coverage. I’ve seen people test it and the signal quality is still a bit hit and miss, but you know what, who knows what it will be like in two or three years. Hopefully, it will mean that there will be full international coverage anywhere. On the other end, it is for countries like Portugal, for countries where the cost of living is a little bit lower, but salaries are also a bit lower, Starlink is still something that’s not accessible to the common person, certainly to the common professional. Currently, it’s about three times the price of a good wired connection. It still needs some work.

Jesse Chambers:

Absolutely. We’ve found, interestingly, as we’ve traveled more internationally, there’s better, cheaper access to broadband internet in large international cities, whether that’s Lisbon or Porto or Mexico City, or some of the Mexican resort communities. Gigabit internet speeds in Mexico City are like $20 to $30 U.S. per month, which is unheard of in the U.S.

Luis:

Yeah, that’s the case in Portugal. Portugal actually has quite good wired internet, but then the signal internet is not great. Either you’re in a place that has it and you have really good quality or you don’t.

Jesse Chambers:

I very much view internet access, broadband internet access as something akin to phone coverage or emergency services or even power at this point. I think that anywhere you can get power to your home, you should be able to get broadband internet in any country in the world at this point. I think that we need to do that for each other, for our citizens and for the good of the global economy going forward.

Luis:

Absolutely. I do think that it’s an essential good. I’m actually an internet maximalist. I believe that good quality internet should just be considered such a baseline thing that sure, whatever, you can pay to have access to more features or more speed or et cetera, but I think that a certain baseline speed should just be made freely available to all right. That’s my position.

Jesse Chambers:

You and I are in violent agreement.

Luis:

Anyway, let’s talk a bit about the building of wrkfrce. I want to start by asking about the expertise of the people that contribute to the site and how you pick them, because I mean, I know from my experience, this podcast was born, for me getting your remote position, a fuller remote position and wanting to learn more from it, but it was some of the experts were quite expensive, were hard to get in touch with. I figured out, okay, I’ll make a podcast, I’ll scam people into being in my podcast. Then, I’ll learn from them. That was the whole plan. 160 episodes in, I have to say it worked beautifully for me, but the point is it’s hard to find people that know how to do remote work great, that are available to produce content because usually, they’re doing their remote work with their remote teams. How do you did it? How do you find the experts that produce the content for wrkfrce?

Jesse Chambers:

Sure. There’s sort of two camps. We have actual experts in the first camp, many folks who have been on this podcast. We have Darcy Boles, we have Iwo Szapar, we have Goncalo Hall, we’ve got Chase Warrington, a lot of folks who are known in this space. Darren Murph is another who, we allow wrkfrce to be a platform for them to share their expertise. And so, they might be third party folks who have other day jobs.

Jesse Chambers:

In those cases, we look to them and we say, “Hey, you’re an expert in this space specifically and we’d love for you to share your expertise with our audience.” The advantage that we give those folks, because they have day jobs to do and other responsibilities is that we tell them it doesn’t have to be gold-plated. The article or the piece of content doesn’t have to be perfectly polished when you hand it to us. We have a team of developmental editors and copy editors who can take a very rough, rough draft and turn it in partnership with that expert into a very polished, final product that they can be proud to share, not just on wrkfrce, but to their social channels and to other places.

Jesse Chambers:

And so, that’s a real benefit for them because this is a resource that they have within wrkfrce. It also gives them another platform beyond their company blog or beyond their LinkedIn profile to spread their message and to build their profile to the community. That’s sort of the one bucket. The experts and candidly, Luis, it’s a lot easier to get experts to sign up and want to create content on wrkfrce once we were live.

Jesse Chambers:

Before we launched, there was a lot more convincing and explaining that I had to do to get people to be a part of what we were doing. But now, we’re actually in a really enviable position of people approaching us with concepts and experts coming to us and saying, “Hey, I want to be a part of this, really like what you’re doing,” or existing experts who might have a new concept or a new piece and they say, “Hey, we think wrkfrce would be a great home for this article that we want to get out there.” That’s been a really pleasant surprise and something that we’re really happy to see is more people coming to us and wanting to use wrkfrce as a platform.

Jesse Chambers:

The second component, which actually by volume is the larger percentage of our content is created by freelance writers. Myself and our content team, we’ve had, at different times, a managing editor, developmental editors, we’ve had a chief creative officer and me come up with content, come up with concepts. Really, it’s a question of what are things that we don’t see out there.

Jesse Chambers:

Something that I think is a general phenomena is that especially post pandemic, all the publishers from the New York Times to the Washington Post to the BBC are creating content about remote work, but my observation is that they are talking about remote work and about people who work remotely. They’re not talking to remote workers and to people who are trying to manage or trying to change their career. And so, that’s really the lens that we use and we see where the gaps are. We see what are the pieces of content that we wish as remote workers that we would see and we commission those articles to be written.

Jesse Chambers:

We have a pool of freelance writers from all over the world and we have them take those concepts that we come up with and build them into stories. Obviously, the concepts can change a lot from the seed of the concept to the final product. That’s where professional freelance writers and editors come in. Tapping into that pool of freelance writers and looking and really being experts in the space and surveying what exists and how that works within our brand and then bringing those content concepts to fruition and publishing them to our audience.

Luis:

Nice. What’s usually your criteria when you’re deciding if that person is going to be a good fit, if that person is going to do a good job of giving new, actionable, interesting knowledge to your audience?

Jesse Chambers:

I mean, for the freelancers, there’s no criteria. The proof is in the pudding. We give them an assignment and if it comes back and it’s good, we’ll work with it and publish it. If they missed the mark, maybe we can’t publish it, but we certainly won’t give them an assignment again. For the experts themselves, I try to think of it as reporters who have beats. Different folks will have different areas of expertise specifically. Darren Murph, who’s the Head of Remote at GitLab is somebody who has been sort of flying the banner for the head of remote role and really advocating for remote work in general in this space. And so, he’s somebody who can have a broad purview, but also can give really actionable insights to how a major company with 1,300 plus employees across the globe is making remote work and going public.

Jesse Chambers:

Then, you have somebody like Darcy Boles, who is very focused on remote work culture, and that’s been her role and her expertise. And so, a more narrow focus in that way. Then we have someone like Sarah Archer who is a confirmed digital nomad. She’s been a digital nomad for four plus years. And so, she’s able to speak with a lot of authority around topics very specific to digital nomadism. Similar to the question you just asked me, how do you get internet access when you live in 15 countries in a year and answering those questions very specifically. We try to look at it as beats for very specific areas of expertise and somebody who can speak with authority in those spaces.

Luis:

Got it. Got it. That sounds very legit, very interesting. How do you tie everything together? You are obviously the CEO and founder, what does your typical day look like? How do you start your workday? What does your virtual office look like? What’s on your schedule? How do you juggle all of this to make sure that, and I’m asking because I’ve done this in the past many times, I’ve done it in the gaming space, and I’m always looking forward to learning new tricks.

Jesse Chambers:

I’m smiling. The podcast audience can’t see me, but I’m smiling because this is a question I ask other people in our space all the time, because I want to get better. I want to learn from them and learn what they’re doing and how they’re making it work. I’m going to give you-

Luis:

Well, I can share some tips as well, helping each other out.

Jesse Chambers:

I hope you will. When I’m done, you can go. I’m going to give you my full answer. My full answer might seem kind of off because it’s not just about work, but I start my day, if I’m honest, the first thing I do after I wake up is I scroll through my inbox and my notifications on my phone to make sure nothing’s exploding, make sure that there’s nothing that I need to deal with right now. Assuming-

Luis:

It’s a terrible habit, but I do it too.

Jesse Chambers:

I mean, it is what it is. I’m the founder. I’m ultimately responsible. More days than not, nothing is exploding. That’s the good news and your definition of an explosion can change over time. The first thing I do is just scroll through that and say, “Okay, nothing’s blowing up. I’m going to be okay.” Then, I do three things.

Luis:

The website is up. It’s a good day.

Jesse Chambers:

As long as there’s nothing bad from AWS, we’re usually pretty good. The first thing is I make a gratitude list. I write down five things that I’m grateful for from the previous day, usually very small things. I had a good night of sleep. I had a nice dinner. I had a nice conversation with my mother yesterday, whatever that is, but I make a gratitude list of five things I’m grateful for.

Jesse Chambers:

The next thing is that I meditate for 10 to 15 minutes right after the gratitude list. Then, I get a workout in. Lately, because I travel so much and I’m in the Airstream and I’m traveling other places, I used to ride my bicycle, but now I’m a jump rope geek. I jump rope for 15 to 20 minutes. Then, I come back and I try and eat a healthy breakfast. I try to do those four things every day, because if I start my day with those four things, I can give myself some slack and I can say I’ve done that. That really is an hour.

Luis:

It’s fire watch, then it’s gratitude, exercise, good breakfast. That’s it.

Jesse Chambers:

Gratitude, meditation, exercise, healthy breakfast. The fire watch, I’m admitting to that. That’s not part of my morning routine. That’s just something that I’m disclosing to you, but the morning routine is those four things. It’s gratitude, meditation, exercise, healthy breakfast. From there, then I-

Luis:

You’re a much healthier person than me, by the way. I just wake up and work.

Jesse Chambers:

Well, I mean, for me, I jokingly say that the exercise is for me more about mental health than physical health. I just feel better. It’s sort of a coffee replacement for me and I can feel better about myself. I’m not running any marathons anytime soon, the least, you know what I mean? I don’t want to give your audience the false impression that I’m some sort of paragon of health, but it makes me feel good. You know what I mean? It makes me feel good physically and good mentally if I do those things.

Jesse Chambers:

Once that morning routine stuff is out of the way, call that maybe 90 minutes, and then, after a shower, that’s maybe an hour to 90 minutes in my morning and then I’ll get in. In the morning, I triage my inbox. It goes from what’s on fire to what needs a response right now. Many things don’t need a response. I’m a big fan of the Gmail add-on called boomerang, which allows you to snooze an email or to send an email to somebody and say, “Bring this back to my inbox if they’ve not replied in a specific period of time.” If they haven’t replied in one day or four hours or four days or a week, I’m a zero inbox nerd, so that I can try and get my inbox as manageable as possible.

Jesse Chambers:

My Calendly is set up and I prefer to have meetings in general. I can do this outside of this, but people can book time with me to meet anywhere between 11:00 AM and 3:00 PM, because I find that that’s the time that I have the most energy for face-to-face conversations, and that I’m best at that. And so, I will try to do my focus work, my top priority stuff in the morning before that time, have those meetings and face-to-face conversations in the middle part of the day. Then, late in the day, I will try to come back again to what is my top priority for that day and how do I make headway on that.

Jesse Chambers:

I might not finish that task or if it’s a big project, especially, but I try to dedicate at least an hour every day to my top priorities. I heard a quote recently from James Clear, who’s an author I really like that says, “In the long run, prioritization beats efficiency.” And so, I try to think about that and try to rigorously prioritize things because I know I’m not the most efficient person and just focus on what is my top priority for the day.

Luis:

What do those meetings usually look like? I’m thinking from synchronizing the team perspective, is there is opening to meetings and the team just picks to talk with you about what they feel they need to talk with you? Is there some kind of all hands-on meeting at some point in the week? How do you set the pace for the team, I guess?

Jesse Chambers:

The wrkfrce team is, I’m happy to say, largely asynchronous. One of the choices that I made early on knowing that I was going to be leading a totally remote, fully distributed team was to, and this is heresy in some circles, we don’t have Slack. I didn’t want Slack because Slack to me demands a more immediate response. And so, we use primarily Asana as our workflow tool and communication tool around projects, because an Asana message or task to me demands a response in a 24-hour period, whereas a Slack message demands a response now or within an hour. It’s the flashing button.

Jesse Chambers:

We are communicating and working on projects, whether that’s editorial or business or product primarily in Asana and doing so asynchronously. I have weekly one-on-ones with most of my team that we do either on the phone or on Zoom. We generally, lately, will do Zoom if there needs to be screen sharing, but more often than not, we’re not doing video just because I think that video causes Zoom fatigue. That’s how the team is going and then we will have sort of departmental or regularly check-ins at the group level on a biweekly or monthly basis, but the majority of my meetings during that time are with external folks, whether that’s advisors, or company partners, or investors, all that type of thing, like podcasters, people who fall into those buckets who are booking time with me in that window.

Luis:

I’m curious to ask your thought process about picking Asana, because for what you described, for me, the sweet spot is Basecamp. I actually use Slack, but it’s kind of a compromise. I wouldn’t use Slack just as you, but some of my colleagues prefer it. They’re the majority. I try not to be the guy who imposes stuff on other people, so I’m like, “Okay.” But I personally much more enjoy the kind of chat in Basecamp much more, but Asana is a bit of an odd pick for me. If you could expand on that, why that decision?

Jesse Chambers:

Also, too, I don’t want to demonize Slack. Slack is a great tool and I am sure that as wrkfrce grows, we will have Slack. I don’t want to take a religious stance against that. I do think it’s-

Luis:

You should check out Twist. You probably have talked with people, it’s from the same team that does the… What’s the test, to-do?

Jesse Chambers:

Doist. Love it.

Luis:

Doist, yes. You should check out Twist. I actually think that’s a great Slack alternative. They don’t sponsor the show, folks. I’m just saying this just as far as the conversation.

Jesse Chambers:

Maybe they will, maybe they will. I think that Slack has its place. What’s interesting to me is, and all of these tools, we fit into the culture of companies in different ways. That’ll change depending on what the company is, what they’re doing, how they’re working. I’m very interested to see how other companies are doing that and trying to incorporate that into what we’re doing. For example, Darren Murph has written on wrkfrce about GitLab, does the majority of their work, they’re eating their own dog food, all that stuff in GitLab, of course, but they have Slack, but their rule as a company is that Slack is not for business. Slack is the global water cooler. And so, Slack is the place where they have affinity groups and different groups who are doing different things and they’re sharing information and pictures about their days or their weekends or their families. It works for them in that way.

Jesse Chambers:

For me, Asana is solid because of its ability to do projects and workflow management. For me, it’s something that I can put all of the information that I need to organize, whether that’s a project or a company OKR or literally my shopping list into one app that is on desktop and mobile and can be shared with all members of the team and have conversations with them and move things along the pipeline. Especially around editorial, we have quite a lot of different concepts and articles that are in progress or phases and different people who are assigned different things across the same task or project. And so, being able to bring all people under one umbrella in that single tool and @ mention somebody and move it along the pipeline or move it from one project to another is really great and it works well for us because of…

Jesse Chambers:

For me, it has to be something, and this seems simple, but it has to be something that works seamlessly across devices. I need to be able to respond quickly and efficiently on mobile and also need to be able to dive in and do some really heavy project and task organization and prioritization in a big whiteboard-like space in Asana. It works well for me. I’m not saying it’s the end all be all, but it’s something, and to me, it has more features than Trello, which is something that I used in the past. By no means have I got it figured out and by no means are we married to a single product for that.

Luis:

It’s always a work in progress. There is no such thing as the definite tool. I personally, I have the things that are high priority for me, for example, responsiveness. I was also a big Trello fan. I still like the way Trello organizes things, but it was just a bit sluggish sometimes on desktop or on mobile. I also kind of dropped it because of that. But I do think that that’s a high priority for me, responsiveness, but I do think that it’s good to figure out what’s the minimum viable tool for you to conduct your business and then stuck with it until it’s obvious that you’ve completely outgrown it and that you have no choice other than to change.

Luis:

I also don’t like some companies are stuck in an optimizational loop where they’re always trying to find the perfect tool, they’re always switching tools. I think that’s a fool’s errand. I think that you’ll never find the perfect tool. If you’re constantly looking for optimization, you’re just going to be crushed by the learning curve.

Jesse Chambers:

Well, and then, something that I have experience with too is being in larger organizations, you have problem of tool bloat, too many tools, all the tools. And so, within your organization, if you have licenses for Twist and Slack and Asana and Trello and Salesforce, and you know what I mean? Then, nothing is going to get done right because you don’t have a single point of truth. And so, one thing as a remote-first company who is attempting to speak to other remote-first companies and people who are trying to work remotely in the businesses that employ them, we very much take a tinkerer’s mindset to how we work and trying to really explore new tools and explore new processes and learn from other companies and see what they’re doing to try to improve how we work so that we can talk more effectively and with more authenticity to our audience about that. And so, as you say, it’s a constant evolution, it’s a constant process for us to learn and improve so that we can speak more authentically to our audience.

Luis:

Exactly. If you take those tools as the virtual office and you think about the analogy with the real office, sure, a big company might have a large campus with several buildings, but you don’t expect a single employee to do part of their work in five different buildings. You want them to stick as much as possible to an office and to their team. You don’t want people switching around all the time. Definitely, you don’t want that in the digital world as well. All right.

Luis:

I want to move on to some rapid fire questions. The questions are rapid fire, but the answers don’t need to be. You can answer at your own leisure. The first such question I want to ask is if you had $150 to give someone something to everyone in your team and you need to buy in bulk, it can be anything, an experience, an app, something, a tool, a physical tool, but you need to buy in bulk and you can’t give them cash or a cash equivalent, what would you get them with the aim of improving their work experience?

Jesse Chambers:

Wow, this is a good one. I’ll probably want to give you a different answer in 30 seconds or 5 minutes, but I think that-

Luis:

Feel free to come back to it.

Jesse Chambers:

… investing and you and I were talking about this before we started recording, investing in a quality webcam and quality microphone. By quality, I mean, better than the one that’s in your laptop, can really improve… because so much business today is conducted on Zoom, giving your employees the ability to have a quality experience in that environment I think is really crucial. I think that teaching people the simple tools of presenting themselves in that environment, making sure that your camera is at eye level, being able to test your audio so that your meeting partners can hear you is just incredibly crucial. It’s the same way that you wouldn’t show up to a sales meeting in a face-to-face environment wearing your sweatpants and a sweatshirt. You want to show up to any kind of meeting, especially with partners and clients presenting yourself well in that environment.

Jesse Chambers:

I think that you don’t need to spend, you certainly can, you can spend $200 on a great webcam. You can spend $300 on a great microphone, but you don’t need to spend that. For $150 as you said, you can do a lot with a solid microphone and a solid webcam to really present yourself in the kind of way that you want to be presenting in a business setting.

Luis:

For sure. Do you have any specific brands you recommend you’d want to put out there?

Jesse Chambers:

My webcam is more than $150. I have a Logitech StreamCam that I think is really solid, but you can find on Amazon a really solid webcam that’s better than the one that’s in my MacBook Air for $20 or $50. The mic that you’re using is one that I really like, the Yeti Blue microphone is really, really solid. That’s not what I use because it’s actually too good for me. It picks up too much ambient sound and when I’m living in the Airstream or living in an apartment in Mexico City, or a place in the woods right now, it actually picks up more of the ambient noise than I want, so I have a simple $30 Amazon microphone that works okay, but your audience will be a judge of how I sound today.

Jesse Chambers:

I think that there are certain brands that are good, but I think that in general, it’s a question of just spending a few dollars upgrading, because what is in most of our laptops, especially the MacBook Airs and any sort of laptop webcam, especially, is really, really lacking, especially in low light situations. You’re just not going to present yourself the way you would hope to present yourself or the best possible way that you could in a business setting.

Luis:

For sure. There’s definitely no better way to ruin a remote job interview even, or even a remote meeting if you look like someone out of a video game, FMV from the ’90s. That’s definitely not a great look. Now-

Jesse Chambers:

Well, it’s not going to help. It’s just not going to help. It’s not going to sink the ship, but why-

Luis:

It’s hard enough to connect. It’s hard enough to connect over a video. I mean, I’m not saying you need to get a full virtual reality helmet, it would be cool once that technology is a bit less heavy and a bit more accessible. That’s probably going to be very cool. I have to tell you that I’ve tried Facebook workspaces. Even though it’s still very junky, clearly, it’s not ready for prime time, it was immediately more engaging being with the colleague there than being on a Zoom call, I can tell you that, but the point is you’re losing something by being in 2D. Recognizing that you’re losing something, you need to make what you do have as best quality as possible.

Jesse Chambers:

Couldn’t agree more and I think that the only thing that I would add to this, and now we’re in a tangent, but you said doesn’t have to be a rapid fire answer.

Luis:

Of course.

Jesse Chambers:

I think that all of these tools will have their place. The more immersive Facebook workspaces solution, that will have its place. Zoom, although imperfect, I think will continue to have its place, but I think that we make a mistake when we think about trying to work eight hours in these environments. These are strong spices. You don’t want to use too much of the spice and ruin the dish.

Jesse Chambers:

I think another thing that’s important having said that it’s crucial to present yourself well and have the tools to have an excellent video experience, it’s also important to meet the people you’re meeting with where they are. For example, when I share Calendly or whatever tool to book time with me, I give people the ability to choose. Do you want to meet on zoom? Do you want to meet on Google Meet? Do you want me to give you a phone call instead of doing a face-to-face Zoom-like experience, because some people, after two plus years of a pandemic, some people are just sick of Zoom.

Jesse Chambers:

I can’t tell you how… I used to be surprised by this, I’m not anymore. I would say in my Calendly alone just based on one man’s experience, when I give people the choice to book a video call or a phone call, easily 60 to 70% of people are choosing phone over video these days, just because I think people are so Zoomed out. And so, I think it’s important to meet people where they are in the format that they want to speak with you in.

Luis:

That’s very interesting. I think about that all the time with the podcast. Let’s switch back and forth. My reasoning is actually, I try to think about it from the audience point of view. What’s going to get a better podcast for the audience? On one hand, if we just do the call with audio, we are getting the exact same output as the audience, because this is an audio only podcast. If we’re only doing audio, it’s not like the audience is missing on anything right.

Luis:

Now, we’re doing video. I can see my face. I can see yours, you can see mine. That modulates the conversation in ways that the audience is not privy to. Definitely, they’re not getting the full experience that we’re getting as the audience. On the other hand, I usually try to stick with video because I just think that it lets me be more engaged. If I’m more engaged, then the conversation will be better for the audience even though they’re not getting all the inputs that I am. It’s an open question for me. I find it hard to decide.

Jesse Chambers:

Well, I think you’re absolutely right. I think why that’s right is because you have situational awareness and you have an end result in mind. As you were just speaking, I was nodding to something that you said, you get that nonverbal cue, we’re able, I hope, to have a final product for the audience audio only that is enhanced by the fact that you and I can see each other right now, but each of those situations, and it’s going to vary by how many people are in the meeting or in the podcast. And so, I think it’s fine to admit, and we should, we must admit that we’re all still learning how to make this work. The only way that we’re going to continue to learn is to tinker and to learn from others and ask people how their experience has been, and again, giving people the option to choose the experience that works best for them.

Jesse Chambers:

And so, I love it. I am always pleased when I give somebody the opportunity to book time with me and they choose a phone call because I think many hours of Zoom a day is depleting to me. And so, I’m happy to certainly meet with people in whatever format they want to meet, but it always takes a little bit of pressure off when they want to do audio only.

Luis:

For sure. Understood. What about for yourself, and this can be for any amount of cash, what is the purchase that you’ve made that has most improved your work experience?

Jesse Chambers:

Wow. Purchase that I’ve made that’s most improved my work experience. It’s a series of purchases, but investing in the ability to have, and this can be a monetary investment, but also an investment of time and energy. The thing that you and I were talking about earlier, just connectivity, just the ability for me as a founder, as a leader to remain connected in all the ways that I have to think about and do that from phone, data, 5G, LTE to this new fiber internet service that we have here in the woods to making sure that when we’re traveling and booking Airbnbs internationally, that I’m asking the host to send me a screenshot of their speed test of their data speeds. I think about that all the time, because as-

Luis:

That’s a great tip, by the way.

Jesse Chambers:

As a founder and as a leader, I hate to say it, but connectivity is just table stakes. I have to be connected. I have to be able to do the things I need to do to run my business and run my life. And so, I wish it were just something I could throw money at, but instead, it’s something that I have to be mindful of and take the time to plan for so that I know that I can be present and can be connected and do the work that I need to do when I’m ready to do it.

Luis:

Got it. Got it. All right. Let’s talk for about books for a moment. What are the books that you’ve given out the most?

Jesse Chambers:

What are the books that I’ve given out the most? This is not probably the answer that you’re looking for, but it’s a funny… It’s what comes to mind. It’s a children’s book. It’s a children’s book and I’m struggling to remember the name of it right now, but, oh, shoot. When I was a little boy-

Luis:

I give out The Little Prince all the time.

Jesse Chambers:

If I can’t remember it now, I’ll send it to you later and we can put it in the show notes, Luis, but it’s a funny thing. When I was a little boy, my grandmother had this book about these mice, it was a children’s book with amazing detailed images about these mice who lived in a tree. These two baby mice found a secret passage and a secret door and they found a part of the tree that was unlocked. When my grandmother passed away, I was 16 years old and I thought about taking that book from her house and keeping that as a memento, but I was 16 years old and I said, “I don’t need a children’s book.” And so, I didn’t do it. Didn’t have that book for 20 years and I always thought about it.

Jesse Chambers:

I always would ask children, kindergarten teachers and librarians, “Have you heard of this book?” I would sort of describe it to them because I didn’t remember the title and nobody had heard about it. It went on for so many years that I started to think that this was a figment of my imagination. Maybe it wasn’t a book. Maybe it was a story that my grandmother told me and I remembered it was a book. Finally, in my late 30s, I found this book and I found a copy of it in the UK and I bought like 20 copies of it on eBay.

Jesse Chambers:

Now, whenever friends or a family of friends have a kid, I will give them a copy of this book and sign a little engraving to it telling them the silly story about how I didn’t think that this existed, but I think it’s something, I tell this story because I think it’s something about sort of believing in yourself and being able to chase over 20 years this silly little idea that I wasn’t sure if it was a faded childhood memory or something that I had imagined. And so, it’s really special to me in that way. All evidence to the contrary, I can’t remember the title of it, but it’s a very special book to me.

Luis:

That’s a great story, actually. Thank you for sharing. It’s really nice, really nice. My final question, it has a little bit more of a setup so please bear with me, but let’s say that we’re in a COVID-free place where we can easily meet for dinner in large numbers and have a good time. You’re hosting a dinner, attending are going to be the decision makers from top tech companies from all around the world and the conversation, the round table in the dinner is going to be about remote work and the future of work. The twist is that the dinner happens at the Chinese restaurant, so you, as the host, get to pick the message that goes inside the Chinese fortune cookie. What is the message going to be?

Jesse Chambers:

The message is sort of a quote of inspiration and something that really resonates with me and something that’s actually sort of the motto of wrkfrce, and that is designing your career around your life, not vice versa. That actually sounds kind of fortune cookie-ish.

Luis:

Design your career around your life, not vice versa. That sounds like really good advice. Tell me a bit more.

Jesse Chambers:

That’s sort of the founding principle and the motto of wrkfrce, because I think certainly, pre pandemic, there were too many examples of people that I saw who were designing their lives around their careers. The example that I give all the time is, and everybody knows somebody like this, the family who has to relocate from one city to another, from Louisville, Kentucky to Chicago, Illinois, and pull their kids out of school, sell their house they may like, have to buy a new house, all because one of the parents has a new VP who’s based in Chicago and that VP wants all of his direct reports to be in his office. No other reason than that. That VP may work for that company for two or three years and then may move on to some other company.

Jesse Chambers:

And so, all of these people and families, I think this is especially true pre pandemic, have had to uproot their lives and change the ways that they would want to live to cater to their work and cater to their careers. I think that one of the silver linings of the pandemic has been people waking up to the realization that they don’t need to do, that they have the freedom to design their careers around their lives, not vice versa, and they have the freedom to push back on their employers when they say, “Hey, we need you to move to Charlotte or London or fill in the blank.” And say, “I don’t want to do that. I don’t want to come into the office five days a week. How about coming into the office two days a week? Or how about I commit to flying to London for one week per month every year instead of having to uproot my family and move there.”

Jesse Chambers:

And so, I think that one of the things that we’ve seen, we call it the great resignation or the great reorganization, but just this awareness coming out of the pandemic that we don’t need to be so militant about giving up elements of our lives that are important to us to cater to our careers. And so, I think that’s something that’s resonating with more and more people and I’m really happy to see that.

Luis:

I think that makes absolute sense. Some people push back saying that, “Well, if you really believe in idea, if you really believe in a company mission, you should be willing to sacrifice something for it.” But you know what, my answer to that would be that you are. You are giving them the best years of your life. You’re giving them your creativity, your energy, et cetera. You’re getting paid for that, fair enough, but the reality is that most people who really commit to something go above and beyond what they’re supposed to be, being paid for. You don’t need to do the show of filthy to move towns or to quit this or to quit that just for the sake of the mission. You should be able to contribute even more than you’re expected to to a company without necessarily needing to reorganize your whole life around it.

Jesse Chambers:

Absolutely. Absolutely. I think, couldn’t agree more. I love the saying that time is our most valuable asset. And so, if we’re giving our time to an enterprise and we’re demonstrating our value and we’re achieving the goals that we need, and this is not to say that every company should be fully remote all the time or that there is no place for the office. I certainly think that there’s a lot of value to sharing space and to working in an office in certain times. I just think that for the vast majority of workers, certainly the vast majority of knowledge workers, it is no longer a requirement to be in the office from 9:00 AM to 5:00 PM, five days a week. That to me is just silly. I think it’s demonstrably false. I think that the global business community has proven that over the last two plus years, that that is a false choice and not one that we need to cater to and design our lives around any longer.

Luis:

Absolutely. Absolutely agree with all of that. All right. Well, it’s been an absolute pleasure having you here, Jesse, would you like to tell our listeners where can they continue the conversation with you? Obviously, we’ll include the links to wrkfrce in the show notes, but if you’d like to add anything, please do.

Jesse Chambers:

Sure. Well, just want to start by saying thanks again for the opportunity, Luis. It’s been great to meet you and to speak with you. I hope that your audience has gotten something out of our conversation. I certainly have. If anybody would like to get in touch with me, there’s a bunch of ways to do that. wrkfrce is the brand that we’re talking about as the company that I founded. Crucially, we don’t spell wrkfrce with any Os. It’s wrkfrce without the Os. We say we don’t use Os because offices are optional, wink, wink. It’s spelled W-R-K-F-R-C-E. You can find us at wrkfrce.com, wrkfrce on Twitter, wrkfrce on LinkedIn, any of those places.

Jesse Chambers:

Folks can also get in touch with me. We’re a growing brand and I would love to hear any feedback that people have on the work that we’re doing in those spaces. You can get in touch with me on LinkedIn, follow me that way, or people can email me directly. My email is J-E-S-S-E, [email protected] I would love to hear from your audience and would love to hear from you again, Luis.

Luis:

It was an absolute pleasure. Thank you so much for being here. We’ll have all of that in the show notes and I think that’s a wrap. Thank you so much for being here, Jesse. It was a pleasure.

Jesse Chambers:

My pleasure, Luis. Thanks a lot.

Luis:

It’s my pleasure to have you all listening. Thank you so much. This was the DistantJob Podcast, your podcast about building and leading awesome remote teams see you next week.

Luis:

And so, we close another episode of the DistantJob Podcast. If you enjoyed the episode, please, you can help us out by sharing it on social media. That would be great. It’s how we reach more listeners and the more listeners we have, the more awesome guests I can get in touch and convince to participate in these conversations that are a joy to have for me. I hope they’re a joy for you to listen to as well.

Luis:

You can also help a lot leaving reviews on iTunes or your podcast syndication service of choice. Reviews are surprisingly helpful in helping the podcast get to more listeners. Now, another thing that you might want to do is go to distantjob.com/blog/podcast. Click on your favorite episode, any episode really, and subscribe. By subscribing, you will get a notification whenever a new episode is up and whenever we get the transcripts of the episode up, so you can actually produce the conversations in text form.

Luis:

Of course, if you need to find a great employee for your team, a great remote employee, you should take the whole world into consideration and not just look to hire locally, not just look to hire in your country. Look around the whole world because that’s the talent pool that contains the best talent. To help you with that, again, distantjob.com is the perfect place to start. You will tell us who you need and we will make sure that you get the best possible candidate 40% faster than the industry standard. With that, I bid you adios. See you next week on the next episode of DistantJob Podcast.

Deciding to quit your 9 to 5 job isn’t easy. But for many, it’s worth it. During this podcast episode, Jesse Chambers shared his story of how he quit his job and became a digital nomad entrepreneur traveling in an RV through the US.

He also highlights why we need to change our mindset to live a happier and more fulfilling life. Instead of prioritizing work above everything else, we need to design our careers around our life.

Highlights:

  • How wrkfrce was built
  • Insights about being a digital nomad traveling and working in the US with an RV
  • Tips to find reliable Airbnbs and places to stay as a digital nomad
  • How he built an expert remote work team that shares stories in the wrkfrce blog
  • Why prioritizing is key when being a remote worker
  • Benefits of having a 100% async team

Book Recommendations:

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Are you our next superstar remote developer?

You live, breathe and eat code, and have fun figuring out how to solve problems. And you love living in South America or Eastern Europe. But you don’t feel as fulfilled as your friends in North America.

I NEED A JOB