Co-hosts: Jonathan Sharp & Ari Winokur

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Jonathan Welcome to the Remote Works Podcast. I’m Jonathan Sharp, and I’m here with my friend and co-host Ari Winokur, and we’re excited to kick off this inaugural episode. So, we’ll jump right into it. And Ari, why don’t you give them just a brief background of where you’re coming from?

Ari Well, sure. I’m off the East Coast of the U.S. here. Been there my whole life, and been working a lot for the past ten, fifteen years mostly in sysadmin. Done a little web development as well on the side, and looking to try to get into the remote world. Right now, I’m working more in the office world.

Jonathan Well, I kind of come from the other perspective. I’ve been working remote for about eight years now and moved during that time. My background is in computer science and web development, more specifically, but I’ve been an entrepreneur for a couple years and had an experience of running a remote team, in addition to being remote, and currently, I live in Northern Wisconsin, way far north, almost to the Michigan border, and live in kind of the rural area. So, that’s an aspect of working remote that I’ll bring in this perspective. So, kind of our first question is: Who is this podcast for?

Ari Well, we’re looking to cover a good range here. We’re looking at all the people doing all kinds of remote work. You know, you’ve got freelancers, contractors. You’ve got people working full-time at a company working not in an office, and you’ve got the types that are entrepreneurs, which might be a freelancer, might be something bigger. Not necessarily working in a traditional office setting I think is where we’re going here. But we’re looking for all the whole range of it. And working from different locations, too, I think is something that you have a bit more of an interesting experience on.

Jonathan So, kind of breaking these down a little bit, because we mentioned a lot of really good stuff here, in terms of the types of engagement for remote work. So, as we were kind of brainstorming before this episode, there were four of them that really kind of came into play. The first is kind of a freelancer; second is more contract-based work; and then you get into full-time work, which is kind of more of your traditional employment; and then finally, an entrepreneur, which is more of a product-based business or more of the self-employed, but not in the traditional sense. So, as far as a freelancer, I had that experience when I first started out for the first probably almost year. I was doing freelance work, which was a lot of project-based work, some hourly work here and there, but for a large variety of clients. And it was an exciting time, to say the least. I learned a heck of a lot. And then contract work is kind of the next progression with that, and you have fewer clients, but it’s more consistent work. And usually, in the remote workspace, with a contract, you have the flexibility of your schedule, and understanding what needs to get done. And then full-time, why don’t you take that one?

Ari Yeah. Well, you know, full-time work is an interesting thing, because there are different companies. As I’m someone who’s looking to try to break into this remote working world, I’ve looked at jobs that require a set schedule. “You need to be at your computer from this time to this time. We don’t care where you are, but you need to be in front of your computer working.” And there are also the full-time employees who simply say, you know, “Hey, come on, show up, get the work done. We don’t care when.” Usually, I find it’s more customer service, support-type work that requires that so-called nine to five type thing, or a midnight shift, or other types of hours, you know. They don’t really care, again, where you are, because you’re working at a computer. They just want you to be able to cover a certain timeslot. So, there’s definitely, within the full-time world, that’s one of the things about our remote work, because you’re working, say, from home, or wherever else you might be, you can just sit down, open up your computer, connect to the internet, and go to work, whenever that time suits you or suits the employer, depending on the arrangement.

Jonathan And so really, kind of the one common theme throughout what we’re talking about here is the fact that location is really secondary to the work being performed, and the fact that your team is also very possibly not co-located, that everything you’re doing is over an internet connection, in terms of communication, and the types of applications that you’re using to collaborate, which is really a major shift in the way that work has been done since the beginning of time, almost. We had communication in terms of letters and packages and telegrams and that type of thing, so work was done over distances, but this is more real-time collaboration over great distances.

Ari You know, the big thing is, it’s getting away from the idea of having a [INAUDIBLE 00:05:41], so to speak, from one time to one time. Full time might still be, “You need to be from this time to this time,” but your boss doesn’t actually need to see you walk into the office and sit down in that chair. They just need to know that you’re connected in and doing the work, whatever that work is.

Jonathan And that’s a very different management style, too, because in some environments that I worked before, really, your presence was more important than your output, what you were actually delivering.

Ari Sure.

Jonathan I would say my experience has been, since working remote, for me personally and my development, the emphasis has really shifted more towards output than presence, and especially with the fact that, over these last eight years or so, I’ve had a fairly flexible schedule, and I keep regular nine to five hours, but I do have some freedom in that. And so, if I need to take off for an appointment, I’ll go do that. But the understanding that I have with myself, really, and the contracts I work on, is that the results will be delivered. So, kind of, I’m going to jump ahead here to this last type of engagement, which is, I would say, more of a non-traditional one on top of that, and that’s being an entrepreneur. You know, I think when people think of entrepreneur in the internet, snake oil is sometimes mentioned.

Ari Sure.

Jonathan Because there are a lot of products out there. You know, the work from home, and all you’ve got to do is stuff envelopes, or that type of thing, which was a common job. But really, there’s a whole range of entrepreneurs today that are working remote, everything from YouTube stars that really broke into the space by having a great personality and a great product, to those that offer up services and are able to leverage that for scale and growth.

Ari Right. You definitely have that large variety in the entrepreneurial field, and it’s the great thing being an entrepreneur. If you want to then… You know, often you start out, it’s just you, maybe a partner. Your partner doesn’t have to be near you if you’re talking about from a remote perspective. Your partner could be anywhere else in the world. And then going out from there, you just need to build out your company. As long as you find somebody who’s good to work with, you can hire them. It doesn’t matter where they are, either, and you just can grow your company in so much more ways. So, it’s great from an entrepreneur’s perspective. It saves so much on having to worry about finding people in your area, or possibly even relocating your business to where you can find lots of people that can do the jobs you do.

Jonathan Yeah. And that was kind of my experience. For two and a half years, I had cofounded a consulting company with another developer, and what you were describing is really exactly what our experience was. He lived in another state different from mine, and it started out with the two of us, and over the year and a half, 18 months that followed, we grew from the two of us up to a team of about 23. We were in 15 different states and a couple different countries all working remote, and we really had no office, per se. Really, our expenses were payroll, and that was pretty much it. So, there were definitely challenges, being that distributed, but overall, it was really a phenomenal experience and an opportunity that wouldn’t have existed probably ten or fifteen years ago.

Ari Yeah, definitely that all the options out there make it so wonderful, the fact, again, that you can do that. And I think that kind of brings us to another interesting point, which is that we’ve been talking a bit about working from home, but not everybody that does this remote work works from their home. Some people, maybe you’ll spend a little bit of time just getting out the house, too. You might work in a coffee shop for a while, so there are co-working spaces where people can go, a lot of mostly freelancers, but also a lot of these remote workers will go to, where you just are working on your own at a desk, but you’re working surrounded by other people who are also doing their own thing. Some people go to a library. And then some people take advantage of this remote ability, especially if they have flexible hours, and they travel. So, they’ll spend a week in one city and then a week in another city, and I’m not just talking about in the U.S. sometimes. I’m talking people who travel the world doing this.

Jonathan Mm-hmm. That aspect of it is really fascinating to me. I’m at the stage and season of life where I have roots down. I have an eight-year-old daughter and another one on the way. And so, global traveling is more logistically challenging, but just being online and following people on Twitter and Instagram and such, it’s very possibly to see these worldwide travelers. And they will travel literally year-round and stay a couple weeks from place to place. And there are actually even communities that cater to helping facilitate this and helping people work out the logistics, and there’s communities where you can go and stay in a house with other digital nomads for a couple weeks on end, or even a couple months.

Ari Sure. There’s all kinds of programs for digital nomads out there. I know there are some people that are working through a program where they’re literally going around the world in a year from city to city. But, you know, even on the points of families, there are some people who are traveling with children, even around the U.S. or even around the world. Now, I know myself, having my six and a half-year-old, as well, and you having your eight-year-old, maybe it’s not for me or you, or maybe it’s not for our wives, I don’t know, but… [Laughs]

Jonathan Yeah.

Ari Either way, we’ve set down some kind of roots ourselves, but there’s people who will go ahead and do this. And hopefully, we’ll have an opportunity to chat with them in future episodes and find out just how they managed to pull this kind of thing off.

Jonathan So, one kind of keystone thing to this whole experience really is the need for connectivity, and really, the ability to connect to the internet to conduct your work and commerce and that type of thing. One of the opportunities that has emerged as rural broadband has increased and become more prevalent is the opportunity for really rural, remote working, which is kind of my story right now. When I first started out working remote, I was living in Omaha, Nebraska, and there was great connectivity there. We were in a suburb, basically, and it was a large enough city. But now we’re in rural, remote Wisconsin, where our town has about 1,500 people in it. Broadband’s a little bit more challenging, but it’s good enough that we were able to move back here to be closer to my wife’s family.

Ari Sure. Did you get a traffic light yet?

Jonathan We still do not have a traffic light. Just a stop sign.

Ari Ah. Now, that just puts, I think, in perspective for our listeners just what type of rural life you’re living now.

Jonathan Yep, yep, and I think just one more tidbit of information is we’re probably about 45 minutes from the closest Walmart, which we look at as a real blessing.

Ari Yeah. Well, you can’t get much more rural than living with no street light and yet being that kind of distance from a Walmart.

Jonathan Yep. Yep. [Laughs] It gets a lot more lonely the further out we go. And I guess one other point to mention is that internet connectivity did dictate where we located to up here. We are in town, per se, even though it’s a small town, to get the cable internet, and I have both cable and DSL connection, just for reliability and redundancy purposes.

Ari Sure.

Jonathan But yeah, it’s still a neat opportunity. Looking at kind of the main reasons for going remote, what is the purpose and the desire behind this to pursue remote work? And I think there’s a number of ones. For me, the one thing that I was looking at the most was to be closer to my family, and I went remote two weeks after my daughter was born, which, two weeks, was an absolutely crazy thing to do, and I may have been sleep-deprived when I made that decision, but it worked out. So, what are some other ones that you can think of?

Ari Well, yeah. I mean, family plays a big role for my choice, too. I’ve worked some jobs where I’ve been out of the house for over 12 hours a day between the commute and the office time, and that goes to the other thing, is commute. You know, where you’re located. I mean, if you wanted to live in such a rural area like you’re talking about and you want to get to work doing your development work in a…you know, this is real tech work in an office, and working for a business where you have to go to an office, I don’t know. I mean, 45 minutes to a Walmart, how long are we talking to any kind of company that actually does that kind of work? Another hour?

Jonathan Yeah. Oh, there are a few, but when you look at compensation and that type of thing, it’s still a real challenge. And that’s actually one thing that my wife and I talked about when we moved up here, is this was kind of going all in for remote work. I mean, you know, like most guys and most people in the profession, I do whatever it takes to provide for our family. But, at the same time, introducing a commute of at least an hour, and we do get snow up here from time to time, so that adds some complexity to it…

Ari Just since you mentioned the commute being affected by weather, just for our listener’s perspective, where exactly are you located?

Jonathan We are northwest of Green Bay by about two and a half hours. So, it’s the town of Three Lakes, because we have three lakes in our town.

Ari Now, yeah, that’s a rural life, when you start naming towns like that, too, isn’t it?

Jonathan Yeah. [Laughs]

Ari But yeah, I think people associate Green Bay with being a cold, snowy place.

Jonathan Yes.

Ari So, if you’re north of there, yeah, I think that sets the tone. You know, one of the things we’re talking about is you’re cutting that commute out, in addition to that, since, again, you’re working from home, or from wherever your computer and internet connection is, the opportunities increase. Because now, you can go and get a job working for a company, let’s say, even the whole company is distributed across that whole area, but you could work for a company on the West Coast where you’re living on the East Coast or in the Midwest. And that whole flexibility now where I can just say, you know… I mean, I’ve applied for some jobs recently, working for a company based out of San Francisco, a company based out of New York, and I’m based out of Maryland. So, the flexibility of opportunities is huge.

Jonathan It really is, and I think the other thing that I’ve come to find is that some of the more interesting jobs are remote, and it’s one of the more progressive things that companies are embracing. And likewise, they’re doing so to be able to connect with that talent, because that talent isn’t always local to where they’re at. And when you look at the cost of relocation for the organization paying for it or providing it, as well as the family that has to pick up and move, it’s a huge hurdle, and really, one that they’re able to better embrace with remote.

Ari Yeah, definitely, that whole flexibility. You know, when you talk about that, it goes back to the family thing, too. You know, you don’t have to uproot your family. Or, from another side, some people relocate to a certain area because either spouse or somebody’s in school, and you know, you finish big school, like… Well, even take especially something like, say, a medical school or something like this, then you have to go find a residency somewhere else in the country. This way, you can stick with that great job opportunity you found, and just when your spouse or significant other has to move across the country, you can just go ahead and pick up and move and just keep on working for that same company, and it’s better for the company and it’s better for you.

Jonathan So, I guess one question we could ask is, based on prior experience of going remote, do you think that this is something that you have to learn?

Ari You know, I found it’s come naturally to me, but something which we didn’t really touch on yet is remote is really expanding beyond the tech world. We keep talking about sitting in front of your computer and doing work, and yeah, the computer and the internet connection are huge. But really, you know, I’ve been looking at some interesting jobs that have popped up. I think one of the airlines—I can’t remember now; maybe you can look it up quickly here—has been outsourcing their customer service to remote people.

Jonathan I could be wrong on it, but I think it was Delta, almost.

Ari I thought it was JetBlue, but I wasn’t sure. [Laughs]

Jonathan Well, it’s one of those.

Ari Yeah, it’s probably one of those. Anyhow, there’s also the…I think it was Nordstrom was hiring, also, customer service workers to handle incoming calls to their call center. Instead of having an actual call center, they were going to hire people, fly them out, train them, and then send them home and let them work from home doing the work, instead of bringing everybody in and having everybody come into this huge call center, which I’ve worked in a call center, you know, these big cube farms where everybody’s talking around you… It’s bad enough sometimes for some people that have experience cube farms. When you’ve got everybody muttering on the phone around you because that’s their job, it can be distracting sometimes. So, if you can get a nice quiet space in your house and you can sit down and you can handle customer’s issues, if that’s the kind of job you want to do, that’s so much better, I think, for everybody.

Jonathan Yeah. I think you make a great point there, that it’s not just tech focused now. And I think even online, you’ve seen traditionally jobs and opportunities that have been on location, like personal trainers, for example, that have now had the ability to transition their business to the web. And so, now they’re remote, virtual trainers, which…you know, that really expands opportunity. I think if you take even more traditional services and look at how you could apply it in a remote setting, your opportunity increase is so great.

Ari I just quickly did a Google here, and there’s actually five different airlines that are doing some kind of telecommuting work for their customer service and such things, and JetBlue and Delta are both on the list, so there you go.

Jonathan Oh, there we go. We were both right.

Ari [Laughs] So… But you were talking about from that whole health perspective, the personal trainer. I knew somebody training for a marathon. They trained to run the New York City Marathon. Unfortunately, it was the year of Hurricane Sandy and that got cancelled.

Jonathan Ooh!

Ari But nonetheless, throughout the experience, they had a coach that they paid for to work, help them through in terms of their eating and their running and how they were doing, and all the kind of stuff you had to do to learn how to pace yourself and eat properly to be ready for that kind of big run. And you know what? That person wasn’t there with them watching them run, watching what they’re eating, talking to them. The person was in some other state. And so there’s that. And you have the personal trainers that come to your house and work out with you. I’ve even heard people doing the portable gym idea now, where a personal trainer has a gym inside the back of some kind of van or truck, drives it over, helps you through a workout, and then drives off to the next customer. You know, remote comes in all shapes and forms.

Jonathan [Laughs] It really does. And I actually kind of like that example. It means that you’re not going to buy a piece of exercise equipment that you won’t use. [Laughs]

Ari Right. You go and you hire the guy. The guy comes to you… The guy or the gal comes to you, does the workout with you, and leaves, and you don’t have to go ahead and buy anything — I mean, unless you want to continue doing the workout on your own. It’s good for somebody like me, who probably wouldn’t use it unless the personal trainer was there.

Jonathan Yeah, I think I would need that level of motivation, also. [Laughs]

Ari [Laughs]

Jonathan Well, I think as we’re getting closer to wrapping up this segment of our inaugural episode here, talking about kind of books knowledge and more, are there any books that you would recommend on this topic?

Ari So, yeah. So, when I first started getting interested in remote work, one of the first companies that piques my interest in the whole thing… Because I was working a lot and getting into the web development — specifically, working with WordPress. There was a great book, which unfortunately I don’t have in front of me, so I can’t remember the author’s full name. Well, first name is Scott. The book is A Year Without Pants. We’ll make sure when we get the show notes together that his name is in there. But A Year Without Pants was a very interesting perspective on going in and working. Scott was someone who had worked for big companies like Microsoft, and then he went contract/freelance kind of world, doing management consulting, really, and he had been working with the company Automattic behind Another book, which I’ve actually recently picked up and am very much excited to start reading, is a book called Remote. Can’t get more simple than that.

Jonathan No. It’s almost a keystone book, or one of the first ones that you should start out. And I believe it originally came out in 2013, so it’s a couple years old now.

Ari I thought it was older, but… Yeah. But the concept behind it itself is incredible because it’s written by two guys who I think started the company, what was it… 37signals was the original name of the company. They’ve changed the name since.

Jonathan Yeah, I believe it’s Basecamp now.

Ari I believe something else… Yes, I believe that’s what they did. They went with Basecamp because that was their main product, too. Don’t get scared off. These books are not management books, so if you’re not looking to be a manager, if you’re just looking to try to look at remote work and what it’s all about and how people go remote and what kind of experiences there are, these books are actually excellent books for all those levels, not just for the manager. What about you? Do you have any books, blogs?

Jonathan Yeah, those were kind of the two keystone ones that I’ve been following the most. So, in closing of this inaugural episode, we appreciate you listening.

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