Michael Cronin / The Remote Way

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Disclaimer: This transcript is provided as a courtesy for accompanying the associated episode it represents. The content of the transcript may provide errors or incorrect statements from the recorded episode. Portions of the episode such as opening or closing comments may be excluded for brevity.


Jonathan I’m super excited to have our guest on the show today. Our paths have crossed online a number of times, and he was recently featured in a Silicon Prairie News article about The Remote Way. I reached out to him and he agreed to be on. So, Michael, welcome.

Michael Thanks, Jonathan. Great to be here. Thanks for having me.

Jonathan So, Michael, why don’t you give us a brief overview of your career to date, and kind of where you’re at?

Michael Awesome. So, my career really started at a business pitching competition at Queens University, where I was going to school in Canada. There, I had met one of the judges, who offered me a job within five minutes of meeting me, and so I decided I would take it. So, he gave me his business card. So, I sent him an email to follow up about the job the next day and didn’t hear back. So, then I sent him another email and another email. Then I made a phone call to him and heard nothing, so I started messaging him on my LinkedIn. And then I started calling him, emailing him, and messaging him on LinkedIn every single day. Eventually, I added him on Facebook. He said, “You are tracking me down hard enough. You’re persistent enough. You get the job.”

Jonathan Oh, man! That is intense. That is awesome.

Michael So, I mean, if you really want the job, you’ve got to show it, but please don’t call me every single day for 40 days.

Jonathan I think that is the definition of hustle, for sure.

Michael So, then we got going and we launched a company called SnapSaves that summer. It was a mobile grocery coupon app. So, I started just doing sales research and basic stuff, and then just kept pushing it and staying till midnight or 2 a.m. every night and just working away and asking for more responsibility, and finally said, “All right, you know, you’ve gotten through the list of things I can think for you to do. What do you want to do?” And I was like, “Let me hop on the phones. I want to make sales calls. I think I can do it.” So, he said, “Sure. Call whoever you want,” thinking nothing would happen of it. And I would get lucky enough to get a good lead and close a deal pretty quickly, so it got the company going, and we really started moving. And it came to the end of that summer and I decided to drop out of school and pursue SnapSaves. We were running with that one for about 11 months, and then we were acquired by Groupon.

Jonathan That’s huge.

Michael Yeah. So, I was 20 years old when we were acquired.

Jonathan Yeah. 20 years old. That’s even before your 21st birthday. I’d call that a success. So, one of the notions that we look to dispel with this podcast is that it’s just the techies who are remote and working from home. So, how would you classify yourself?

Michael Yeah. I think I’m a digital marketing business development sort of generalist. So, everything from Facebook ads to high level business development, and that is something you’re totally able to do remotely. And the next step there was continuing with Groupon for a year and a half, during which time I would take time to work remotely, travel while I was working remotely, and then I went fully remote about a year ago.

Jonathan Okay. So, as far as where your career’s at and where you’re splitting your time right now, are you still working for Groupon in that capacity?

Michael I’m not.

Jonathan Fully on The Remote Way?

Michael Fully on The Remote Way, 100% all in. So, I left Groupon about a year ago, had a bunch of different consulting projects I was doing in the marketing field. In September, got going on Remote Way, shut all of those down, and 100% focused on Remote Way now.

Ari So, as you’re progressing through your career, was there a particular yearning or passion or direction you wanted to head that kind of came out, kind of emerged out of things as you developed and learned?

Michael Definitely. And I think that came out of having some success and realizing, you know, I achieved my goals, and I kind of got to the end of my goal list, and I was looking around at where I was, paying way too much rent for a small apartment in downtown Chicago, and going, “This isn’t it. This is not why I work so hard.” And so, I started trying all these things, and I was doing scuba lessons and sailing and so many different things, and that started to get me going, and that was what made me excited. So, I started to wrap that in with travel and constant learning. And then that’s when I realized that’s what I really want, that’s where I work for, and remote work allows me to do that.

Jonathan So, you’ve worked full-time and as a freelancer, and then also as an entrepreneur. What have you connected with the most? What’s really made you come alive?

Michael Entrepreneur, 100%.

Jonathan And I think having an awesome success of an exit probably contributes to that a bit.

Michael I think some people are born to be entrepreneurs, and I’m one of them. Even if I’m making a lot of money sitting at a desk, working for someone else drives me crazy.

Jonathan Yep. I totally get that. So, do you really see the definition of entrepreneur as being out there and not really stationary? It’s more of the creative side of it?

Michael Yes, but I think there’s a mix. So, it’s a mix of both sides, and you have to walk the middle way between being too creative and being too analytical, but you have to combine those things right down the middle. And if you go to either side, you’ll start to see it in your business right away.

Jonathan So, growing up, you mentioned that you’ve traveled a lot. Tell us how that kind of connects with the theme of your passion for traveling, and then also how that kind of ties into the Remote Way.

Michael Definitely. So, I’ve traveled a lot through South American and Europe, and my team members have traveled even more than I have, but it’s really my passion. And it was something where I traveled a lot within the U.S. as a kid. I’ve driven through 42 states with my family and saw so much. And it’s amazing. I love those road trips so much, and it was about, like, oh, there’s way more. You know, we covered 42 states of one country. There’s so much of the world to see.

Jonathan Yeah.

Michael And I sort of think about that with Remote Way and a time thing. If you’re working a job and you’re taking a week or two a year to travel, the amount of the world you can see is so small, and I think for so many remote workers, it is about time. It’s about the time to see your kids grow up. It’s about the time to work remotely and be able to travel. And, I mean, years go by and you get a week of travel in it, and that’s crazy to me. Or years go by and you get to go to so many kids events or get to see your kids so much. I think the power of remote work is it gives all that time back to you to be able to choose how you’re going to live.

Jonathan That totally connects with me, too. I spent a number of my summers as a family driving across the U.S., so I’ve got about six states on you, because I’ve been to all 48 of the continental states. Haven’t been to Hawaii or Alaska yet, so that’s on my bucket list. But yeah, fond memories of driving across many states.

Michael For sure. And I’m one of six kids, so we would pack all of us into a Chevy Suburban and fit exactly right in that Chevy Suburban.

Jonathan Oh, man.

Michael It was tight, but it was awesome.

Jonathan I only had one brother, so I didn’t suffer as much there. But it was a Honda Accord, so...

Michael [Laughs]

Ari Yeah. I think my parents had to get a station wagon just because of me and my sister, the amount of fighting. You needed that space.

Michael [Laughs] You still found a way to fight, probably, though. You know, it doesn’t really matter how much space you have.

Ari That’s true. But at least in theory, we had our own room to keep ourselves happy during long family trips. So, Michael, do you identify with the term “digital nomad”, or do you find that as a term that can explain to people what it is that you do? Or do you have another term that you use?

Michael Yeah. I mean, I’m going by digital nomad. It’s a shame that’s become such a buzzword, but these things tend to. Even “entrepreneur” is tough. All these words get hijacked very quickly. I’m not trying to sell any book on how to become a digital nomad to you. So, that definitely qualifies. And I think in remote work, there’s a spectrum, and it starts with people who take one day off a week to work remotely. And then the far end of the spectrum are the digital nomad and the stay-at-home remote parent, of people who are fully remote, fully out of the office. And I would definitely say on that spectrum, I am at the far end.

Jonathan That’s awesome. So, transitioning a little bit now to a slightly different topic, I wanted to talk more specifically about The Remote Way and that program and what you have going with it. So, as I understand it, you’re working out of Caffeine Dreams in Omaha, and you went there. And so, how did you go from working in a coffee shop to this desire to work globally and internationally?

Michael Well, first, shout out to Caffeine Dreams. That’s my favorite coffee shop. [Laughs] If you’ve been there, it’s great. So, that’s in Omaha, and I think I was awoken to it when I was looking around Omaha and seeing how many people were working remotely for large tech firms. And I just realized the scale of this. And maybe if I was in New York City, it would make more sense, but I’m going, “Oh my gosh. These people are all working remotely.” And it was actually on a cold winter night home when I was walking home, and it was about a three miles walk. And I’m just going, “I’m freezing. It’s completely freezing.” I’m out walking, like, “Why do people stay here? Why are people staying here? Why are all these people who could be working from anywhere in the world choosing to work from Omaha?” There’s so much more of the world to see.

Jonathan I’m laughing at that, because I strongly identify with that, having lived in Omaha for seven years. And that wind just cuts through you like nothing else.

Michael Oh, man. It was one of those nights. I was just shivering, just going, “Why did they stop? There’s so much room to the south, so much room to the west. Why did the settlers stay here?” And that made me just feel [INAUDIBLE 00:10:53].

Jonathan Yeah. That’s cool. And definitely a shout out to Omaha. Omaha has a really strong startup scene, as I mentioned Silicon Prairie News before, and we’ll throw a link to that in the show notes. But there’s a great ecosystem in the middle of the country, and you wouldn’t expect it there. So, it’s great.

Michael Yeah. Midwest proud. I love what they’re doing there. It’s a cool spot, too, I mean in terms of people you’ll meet and projects you’re working on. Sometimes, it’s more practical than what’s going on in the valley, but they’re very strong, in terms of good entrepreneurship.

Ari That sounds pretty cool. So, can you tell us a bit about the other cofounders of The Remote Way?

Michael Definitely. So, the other cofounders, the first two are the ones...so, the I guy had to call 40 times, his name’s Anatoliy. He’s been my mentor for four years now. And then Michele Romanow. So, Michele was part of the SnapSaves team. And then after that, she ended up being put on a TV show called Dragons Den in Canada. It’s basically the same as Shark Tank in the U.S., and she’s one of the sharks on the show, so one of the dragons on the show.

Ari Whoa.

Michael Yeah. So, awesome. It’s fun to go see her film, and she has become a serious woman in tech and is a huge inspiration to so many people in Canada, especially women. I think that’s amazing. And then we have Jackie, who was previously managing Uber in Alberta, and she’s joined, as well, on the operations side. So, it’s a strong team. We’ve worked together for four years. Anatoliy and Michele have worked together for ten years and this is our next big project.

Jonathan Wow. So, one thing that really caught my attention, looking at the Remote Way program, is that it’s really all-inclusive. For example, you actually have a nutritionist that you’re working with that’s consulting. Tell us kind of the experience that you’re going for with that.

Michael Yeah. So, I think this is about optimizing your life, and that’s very, very hard to do. And I don’t want to do it in an authoritarian way, where this is the way you have to live, but I think I’d want to provide all the tools to people that they need to exercise and get out there and learn new skills that they could become passionate about, to have a nutritionist, that they’re familiar with the right way to eat, especially when you’re traveling, because it can be very tough to eat right; to provide cultural events for learning. And it’s all about constant learning, so I want you to learn how to eat the right way, how to exercise the right way, how to use local languages, and then how to get around the world.

Jonathan So, it’s really inclusive of how to travel well.

Michael Exactly. And that’s something I’ve been doing with my friends, and we love the way we travel and we’re just trying to expand that and make that something the world can partake in, as well.

Ari That sounds really neat. So, tell us some more, beyond the nutritionist’s angle, what kind of courses The Remote Way offers, how they’re delivered. Are those things in person, remote, and so on?

Michael Totally. So, those things will all be in person. So, maybe I should step back and just give a little explanation on what Remote Way does. So, we provide travel, housing, co-working space, and activities and courses for a group of 36 remote workers going to eight destinations over eight months. So, it’s a community of remote workers coming together, and then we are guiding their experience using these courses. That’s all planned in the evenings or on weekends around work hours. So, it’s very much a work first program. If you want to join Remote Way, you have to have a job and you have to be able to work it remotely. It’s not an extended vacation. It’s not a big party. This is a combination of working and living the best life. So, we’re planning that around nutrition and then around the courses, and that’s all based on our favorite things to do in these cities, and based on continuous learning. So, we’re going to have sailing lessons. We’re going to have a scuba diving lesson. We’re going to have snorkeling lessons. We’re going to go in Medellin and go out to a coffee plantation and learn about coffee beans. We’re going to learn about making mate in Argentina. So, it’s really about growing with the environment and the places you are.

Jonathan That is awesome. So, The Remote Way, all the destinations that you’re going to, South America, Europe, Africa, Asia – how do you go about picking the destinations? What drives kind of the way that that part of the program fits together?

Michael So, our team is very well traveled and we came up with a shortlist from that, of destinations we think would be the best. And then the first thing that would knock destinations off the list is WiFi quality. It’s about work. You have to have WiFi speed. So, we really wanted to go to Cartagena, and the whole city’s WiFi just isn’t strong enough. So, it’s based on our favorite places, but then where is there the best co-working space, and where are going to be able to get work done most efficiently?

Jonathan So, with the WiFi speed, what’s your criteria for that?

Michael So, over 10 MB/s for the entire group is a base minimum that we would need for that to hold.

Jonathan Okay. So, each user would be able to have that level of service.

Michael Right. And we’ll go in and tell places, you know, “If you want us to come and you want our business, upgrade your WiFi, upgrade your power.” And we send people down to test it and to make sure it’s strong enough.

Jonathan Yeah. Because we’ve all heard of the coffee shop that has “the fastest WiFi” – and I’m doing air quotes right now. It’s far from it.

Michael Right. And then it’s different languages and communicating. And it’s going, no, no, no. We need to see the test results.

Ari So, Michael, it mentions on the Remote Way website—and you also mentioned this earlier in our conversation—that one of the ways your program differs from some other programs, and what’s something very focused and unique about yours, is that you’re work first. You’re focused on work and not so much...it’s not an opportunity to travel the world and party. But, you know, there’s emphasis on actually doing things as a group, and so on. So, what do you hope for the culture of the experience to be, and do you expect people to get out of this to start becoming part of that digital nomad life? Or just kind of, “Hey, try it out for these...” I think you said eight months, and then just go back to working in their local coffee shop?

Michael Definitely. So, I think there’s two focuses here; one, allowing existing digital nomads to participate in this, or existing remote workers; but we’re also trying to make this very accessible to people who have never worked remotely before, and to make it a great option that their employer will get on board with. So, we’re doing that by creating a real work-first program. The culture should be collaborative. It’s a great group of mainly 25- to 35-year-olds. Almost everyone in the group is single. 50/50 ration of male to female we’re keeping. We’re looking for people who are very driven in their careers and looking to advance their careers, and have a project that they’re really going on, but don’t view working remotely as a compromise. It’s not a step back in your career. It’s not something that’s going to hold you back. It’s something that will allow you to continue to drive forward, not only in your personal life, but on the career side.

And so, that’s sort of the culture of people who are very ambitious. And one of the things we talk about with people to understand if they’re a good fit is: What is your KPI? What are your key performance indicators? If someone has very strict KPIs with their employer and has a very good idea of what they’re supposed to be doing and what’s the threshold for success, that’s usually a good sign that they’re a good candidate for remote work and Remote Way, and have a career that they’re building. And when we hear people say, “Well, I’m not sure what I do every day,” probably not going to be a great fit.

Jonathan So, changing topics again a little bit and talking more about the logistics of you personally working remote, one of the things I’ve learned is that you kind of insist on using headphones, and it kind of came across in previous discussions that that is a key. To get to work, you’ve got to have your headphones on. Can you talk about that and that process?

Michael Yeah, definitely. I think one of the questions you asked is “What do you have to have around you?” And because that’s never constant for me, the thing that is always constant is my headphones. It allows me to zone in and get my focus with my music, and I always know what music I need. If I’m getting work done but I have spelling errors, I’m like, “Oh, time to put some classical music on. I’m moving too quickly.” If I’m not creative enough, I’ll throw some jazz on. And if I’m just getting busy work done, which everyone has to do at some point, I’m going to throw on a podcast. And, I mean, I’m a total podcast-aholic. It just can either make me focus or it can make me feel like I’m at home if I play the right... If I listen to Garrison Keillor, it feels like I’m back at my home with the family on a Saturday afternoon.

Ari Moving along with that, what does a daily schedule look like for you, especially with this nomad life?

Michael Definitely. So, when I’m traveling and sampling these places, I’m going in and checking their WiFi speed and everything. And that’s a different day. But besides that, I’m focused on acquiring new users through marketing, and then doing interviews with potential candidates. So, I like to get up early and usually try to get some exercise. When we’re in places, it’s a lot better, because it’s hiking, it’s snorkeling, it’s surfing, it’s much more exciting exercise. And then, I’ll work until about noon, take a lunch break, and then work again. And every single day, I have to be outside for the sunset. I’m super passionate about that. I think especially when you’re traveling, your entire rhythm, your Circadian rhythm is completely set by seeing the sunset. So, every day in my calendar, wherever I’m going to be, my sunset is blocked off, and I go for a walk or I go for a hike and I get outside.

And then, you know, I think there’s some debate about this with people, but for an early-stage startup, you’ve just got to keep working. So, I will go as late as two a.m. at nights to just push through and keep doing these interviews, and especially when I’m in strange time zones. I allow participants to work on their schedule, so it can be very late nights. But if I get my sunset and if I’m up early enough to see part of the sunrise, then my sleep schedule stays pretty normal.

Jonathan So, I’m going to play devil’s advocate here a little bit. So, do you have a desire to work from Alaska, where, in the summer particularly, where there really isn’t kind of a sunset?

Michael Oh, man. That’s a great question. I hadn’t thought about it that way. Yeah. I don’t know what I’d do. But there is also a period, I think, of, like, constant sunset over a couple of hours. I’d be thrown off.

Jonathan There is. That’s true, there is.

Ari That’s true. That way you can work until eleven o’clock, twelve o’clock at night and then go outside and catch the sunset.

Michael Exactly. There we go.

Jonathan I may add that as a destination for a future year.

Michael Definitely.

Jonathan So, you’re relatively newer to the remote work, with just over kind of a year and a half since transitioning into that. How do you compare your before and after? Do you feel like you’ve been set loose and you’re free and that you’re really where you’re supposed to be?

Michael Right. So, I think for me, I’m a very social person, and some of the beginning of remote work, I wasn’t doing the traveling and I was just sort of in an apartment. And I get it, that that works for some people, but that drove me crazy, and that did not feel right at all. I need social engagement, and that’s one of the reasons I would work from Caffeine Dreams in Omaha instead of from home. And so, that’s when I... When I started to add the travel and the community component, and when I was doing that with my friends, that’s when I felt like this is perfect. This is the most inspired I’ve been and it’s making me more efficient at my work and making me want to perform and keep going on this trail.

Ari You were talking a bit about internet speeds, about the importance of maintaining at least a certain level of WiFi speed in these locations. So, with all this variety of internet connectivity that you’ve gotten in all these places, have you had any particularly, like, super-fast internet speed that you’ve had experience with? Real fast, maybe, internet connections somewhere?

Michael Only within the U.S., in terms of extremely fast. I know from my... My other teammate is covering the East Asia side, and that’s the gold standard, in terms of around the world, of where you’re going to get the best internet speeds. They’re just years ahead, especially of South America and areas in Europe, in terms of getting WiFi speed and internet speed up.

Ari What kind of speeds are we talking about?

Michael Oh, man. My other team member’s the one who really knows those numbers very well.

Jonathan It’s basically faster than I have in rural Wisconsin. Let’s put it that way.

Michael Exactly. That’s for sure.

Jonathan So, you mentioned KPIs previously, and really, on a personal level, and kind of how you measure and drive yourself, what are some of your self-defined KPIs. and what’s the process you use for tracking those?

Michael Definitely. So, a lot of what I’m doing is marketing acquisition stuff, and it’s about testing... So, I think you can’t set a KPI until you’ve done something. So, you can’t set a KPI for you what your marketing goal should be until you’ve tested and learned and then realized what efficiency is, and then I think it’s always about, even on a next week schedule, trying to beat that efficiency, and beat that efficiency and iterate and improve. So, the KPI should always be getting gradually more difficult. I do a lot of stuff where I’m introducing companies to Remote Way, and so, a lot of that, as well, is gradual improvement of KPI. And that’s the way I think you get to realistic goals and realistic improvement.

I do this with the whole team, though, so even someone who has a newsletter, for their newsletter, they have a KPI of expected open rates. And then, on the next one, they have a new KPI for expected open rates. Everything is managed on a KPI, and that’s very clear, and I think my favorite thing about that... You know, our team is pretty flat. We’re pretty new. But I definitely overlook what’s happening on a day-to-day basis. Everyone’s aware of where they stand when they have KPIs. There’s not a lot of managing to do of anyone. It’s just “am I meeting my goals?” And I work with everyone so that they can set those goals themselves. So, “Here’s what I expect,” and, “Okay. Let’s see what could you improve that at.” And then they’re holding themselves to their own standards.

Jonathan That’s cool. And are there any tools that you use for tracking that over time, or does it really just kind of depend on what the KPI is?

Michael Definitely. So, Pipedrive is great for sales stuff. I use that all the time. I use Tableau to track a lot of other results, and then sometimes, we end up in the dirty old Google Sheets, as well. But another thing I use, I use Zapier. I just want to talk about them for a second because I love them so much. I use them to connect everything, and that makes a lot of things connect and organize that wouldn’t be otherwise and would require manual input.

Jonathan Yeah. And I love them, too. One of the people that I know that works for them who also lives in Omaha and was one of the people that worked with Silicon Prairie News early on, too...and so now he works for Zapier. And so, yeah, just a shout out. This is like the Midwest episode, I think. With a global theme, of course.

Ari Now I just feel left out. [Laughs]

Michael Ari, where are you based?

Ari I’m in Maryland.

Michael Okay. Definitely not the Midwest.

Jonathan Definitely not!

Ari No, no, no. Definitely not.

Jonathan So, Michael, you mentioned reaching out to companies is part of your role in The Remote Way. What are you looking for in terms of company engagement with The Remote Way?

Michael Definitely. So, we’re opening a lot of conversations, just to familiarize them with what we do, something that they can allow for their employees. But we’re also looking at some corporate programs, and I think that can be a big future for this business, as well.

Ari I think that just about wraps us up for today. So, Michael, thank you so much for joining us. We just wanted to give you a chance here. Where can people find you online? For that matter, where can people find The Remote Way, and I guess if people are interested in joining up and experiencing that travel?

Michael Definitely. So, you can find us at theremoteway.com, and submit an application there. We are still accepting applications for a May 1st start. And then you can find The Remote Way at facebook.com/theremoteway, on Twitter@theremoteway. And then you can find me on Twitter @michaelcroninrw, for the Remote Way, and Instagram @michaelcroninrw.

Ari [INAUDIBLE 00:28:45]

Jonathan Consistent branding, which is a key to success.

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