Director of Sales & Marketing, Pagely Inc
HOW DID YOU DECIDE TO JOIN REMOTE YEAR?
Unlike most people I hadn’t seen the Facebook ad of the guy diving dramatically onto the bed with his suitcase ;-) I first learned about Remote Year via my buddy Chris Peloquin (who you recently profiled here). We’re friends of ten years and were living a block away from each other in Phoenix, AZ. He came by my place one night last March to ask me questions about how I do my work for Pagely remotely. He had just been accepted to Remote Year and was debating whether he could do it and hit me up seeking affirmation that he could/should do this. The more I heard him describe the program the more I realized I wanted to do it myself. I applied that night and was accepted a few weeks later. Chris and I both joined the Darien cohort and have been traveling together with the rest of our group for the last 10 months.
WHAT WAS YOUR LOGIC IN JOINING REMOTE YEAR?
So the logic for me went like this:
1) I’m single with no dependents and have a job that allows me to work from anywhere, therefore 2) I’m an idiot if I don’t take advantage of this opportunity to travel the world and work from all these interesting cities vs. staying and continuing to work out of an apartment in the city where I was born.
HOW DID YOU CONVINCE YOUR EMPLOYER TO LET YOU DO IT?
I really didn’t have to. Pagely more than condoned it- they encouraged it. I have a unique work situation in that the company is privately-held and owned & run by a husband-wife team who I’ve known since 2006. But there is actually a funny story in how the initial ask went down.
I had applied to Remote Year before asking my CEO whether he was cool with me working abroad because I figured no sense in bringing this up if I don’t get accepted. I went through a mental/emotional wringer during the application process. The trajectory looked something like this: “Hmm 50k applicants and I’m applying 2mos before the cohort leaves… yea probably won’t get in. Waited 7 days… no response... yea I guess I didn’t make it. Skype interview the next week… sooo that went well, what if I actually do get this?? Will I do it? Wait a week… guess I didn’t get in so it’s a moot point… next day: Got in... Crap. Now I have to actually do this. ;-)” It was a total roller coaster of uncertainty, probably the biggest crossroads moment of my life but in the end by far the best decision I’ve made the past year.
I broached the subject via Slack to my CEO late that night saying “so hey I got into this program where I’d be working remotely... don’t think there’d be any issues that would preclude me from doing my job effectively but just wanted to check and confirm you’re okay with this and have no issues with it.” I got a two word reply from my CEO that night at 2am “Not really.” I didn’t sleep that night at all because I had zero idea how to interpret his response. "Not really” as in “not really cool with it?" “Not really” as in “not really any issues with it?” Ugh… I had been so sure he would be supportive of this plan but his response was indecipherable and unexpected. I spent a sleepless night from the utter ambiguity of that two-word phrase and everything that depended on it. The next morning I got on Slack and said, “okaaay, soooo what did you mean by ‘not really?’” He said, “Sean, I don’t care which continent you deliver results from. Just keep kicking ass.” This is our culture at Pagely and this is why I love my job so much. I wish more employers would place this level of faith in their employees.
HOW DO YOU THINK WORK WILL EVOLVE OVER TIME?
I’m actually speaking on this very topic at PressNomics next week. I think we’ll see a lot more remote work, whether it’s telecommuting domestically or abroad via programs like Remote Year. I think we’ll see a shift away from massive bureaucratic corporations towards leaner teams of freelancers and small firms collaborating. I think folks will develop more deep specialization in hyper-niche fields. Maintaining a personal brand will become even more important than now as it’s that critical mental real estate you own in others’ minds. Resumes will (thankfully) become irrelevant replaced by publicly-accessible, trackable contributions like your github account, your blog, your social media profiles and side project portfolio. I would expect at some point employers who fail to embrace remote work will lose all their A-players to the ones who do. Platforms like Slack, Trello, Google Drive, Zoom, Calendly & Uberconference will obviate the need for a physical office entirely. We operate this way now at Pagely as a completely virtual team and we’re a high-functioning one at that.
KNOWING WHAT YOU KNOW NOW, IS THERE ANYTHING YOU LEARNED THAT WAS SURPRISING OR UNINTUITIVE IN HINDSIGHT?
Great question. I way underestimated the value of the social component of this experience. It’s like you don’t realize what’s missing from your life until it’s ultimately there. Even with deep roots in Phoenix I led a fairly lone wolf social existence there. Remote Year for me feels like a modern-day tribe in that we roam from city to city always having each other’s backs. You bond really deeply with the people you traveling with. Previously I had imagined RY as being more of a travel agency to solve the logistical issues that make this type of work/travel infeasible but I hadn’t assigned any importance to the tribal social camaraderie that develops amongst participants. In hindsight that has proven to be the most valuable aspect of the whole experience. I talked a bit about this “tribe” concept in my Junction talk in London - we really do operate like one and it now feels more normal than not at this point. It will be weird when our tribe disbands.
The other thing I’ve learned is that whatever preconceptions you have about a city before getting there will almost always be dead wrong. I’ve been consistently way off in how I envisioned places ahead of time vs. how they actually are. For instance I imagined Belgrade being like this scene from Eurotrip and Berlin being an impeccably spotless mecca of a city... I couldn’t have been more wrong about each.
HOW HAS YOUR JOB PERFORMANCE BEEN WHILE ON REMOTE YEAR?
Solid. Going into this experience my goal was just to keep up- to maintain my sales performance while getting to see the world. I ended up actually improving my sales performance substantially though while on the road. Being in sales, my monthly numbers are the unequivocal, objective metric to gauge performance. I tallied my average monthly sales numbers for the 6mos pre-Remote Yearand the 6mos post-Remote Year and I’ve done a 44% improvement on my numbers while on Remote Year. Inc Magazine interviewed me on this topic if you want to read more.
WOW THAT'S GREAT. TO WHAT DO YOU ATTRIBUTE THAT PERFORMANCE INCREASE?
I think it’s a confluence of three things. In the first leg of the trip I think some of it was the timezone offset working to our advantage. There’s a company I admire a lot called Basecamp who has a distributed workforce and has written extensively about the benefits of having limited overlapping time slots when team members are online together. These time constraints actually breed efficiency. While we were traveling in Europe the time offset meant I had limited windows of interaction with my team which meant I had to be extremely efficient in communications but also it meant I had the mornings free to either explore the city and get reinvigorated or make progress on strategic initiatives. Either way it was a win. I was finally able to make headway on improving our sales process itself and other strategic initiatives that wouldn’t have gotten done otherwise because I’d normally be buried in my inbox by 9am and too exhausted by day’s end to work on them at night.
I’d say another factor at work here is that there’s incalculable value to being inspired everyday and the self-confidence and revitalization that comes once you’ve proved you can do your work from anywhere.
I was under-stimulated previously in my home environment in AZ. It was easy and predictable. Conversely, every day abroad presents a novel challenge or unique situation that adds spice to life and creates stimulation. It’s intangible and hard to quantify but very real. I make more memories in one month here abroad than I do in a full year at home, and certainly have made more friends during this time. Aside from the increase in monthly sales, I’ve also built some valuable systems for my company in the form of a Sales AI followup automation framework that I honestly don’t think I would have pulled off in my previous situation domestically. It sounds cheesy but you can’t underestimate the boon to your creativity from being put in all these unique situations and being constantly surrounded by other interesting people.
Lastly, there are definitely variables outside of Remote Year that have contributed to those improved numbers. For example, our average deal sizes have been steadily improving, I’m getting better at sales, our process is more systematized now, we hired a SDR to take over lead qualification and free me up to focus more on closing. I think it was the confluence of these three waves coming together to create the perfect storm of awesomeness this past year.
WHERE DO YOU SEE YOURSELF IN 30 YEARS FROM NOW?
Celebrating the 30th year anniversary of you asking me this question 😉 Sorry. Mitch Hedberg reference... (RIP Mitch).
No, I have no idea. I hope to some day build a venture capital firm unlike other VC firm by placing the entrepreneur at the center and supplying not just capital but sales & marketing expertise, contacts and other key pieces to help bring great ideas to market. Shows like Shark Tank frankly piss me off in how they depict the entrepreneur in a devalued role and by portraying deals skewed heavily in favor of the investors as being the norm. I see an opportunity for being able to tip those scales back in favor of the entrepreneur by doing what I do now for Pagely in terms of systematizing and automating sales only on a revshare/equity basis for other startups and solo-founders. I’d like to prove out this concept under a brand called “Startup Hostel” and eventually evolve that into a “venture catalyst” firm once I have the formula perfected. I’d also like to make Charity Makeover a bigger thing. I love facilitating Startup Weekends and could also see myself doing that on a volunteer basis.
ANY TRAVEL HACKS OR GEAR RECOMMENDATIONS FOR PROSPECTIVE REMOTES?
Yea I have a ton. I always film a video the day before we leave each city and in it include observations, travel hacks, gear recs and tips from the month. If I had to pick only a handful I’d say:
Install Venmo before you leave the US. Get a Google Voice number and hang it off that. Remotes who have lost their phones abroad have had trouble getting Venmo back and it’s such an essential app for settling up on food and bar tabs with friends.
Buy Tiles and throw one in each of your bags. I have one on my keys and wallet as well. They work great in airports because there are a lot of travelers with the app and it’s so nice to be able to track down your luggage if it goes missing. I lost a bag on my first day of RY and now I don’t worry about that anymore.
Redundancy in all things but primarily connectivity and power if your job has high availability demands. I have two phones, one with T-Mobile and one with a local SIM for the city we’re in. I have an Anker iPhone case that gives me 2 extra charges during the day and a Mophie power brick as well that can power anything with a USB cord.
Apps like AirBnb, HotelTonight, SkyScanner, SkipLagged, Rome2Rio, TripAdvisor, Hopper, BlaBlaCar, CityMapper, FlyOnward & Splitwise are your friends.
Get a New Outlander day pack (like $20 on Amazon). Probably half of our group uses this specific pack. Always loop the strap through your foot when you’re sitting somewhere. We had one guy who did this and it saved him from a theft and they caught the kid who tried.
TRX has been pretty fantastic for staying in shape on the road. The other alternative is to join a gym in each city but that can be expensive and it just adds another moving piece to worry about in each town. My buddy Chris has led TRX classes in most places we’ve lived and it’s a great training system for travelers.
Take some basic infosec precautions like enabling Filevault disk encryption on your Mac. Setup a mouse corner gesture that locks your screen and just make it a habit every time you leave your laptop open. Do periodic encrypted time machine backups or get one of the SaaS backup services setup. Use a VPN at all times - I use Cloak and love it.
I’ve heard you can activate Google Fi on an Android then swap the SIM to an iPhone. Haven’t tried it yet but that’s pretty fantastic if it works.
When you land in a new city do the “offline sync” for Google Maps as connectivity can be sometimes spotty but GPS works independent of your cell connection. BTW weirdly in some cities Apple Maps is more accurate than Google. I know, crazy right?
This Schengen Calculator is really useful when traveling in Europe. If you don’t know what visa-less Schengen stays are (I didn’t before) look it up.
Research the Foreign Earned Income Exclusion for Federal tax purposes. I helped facilitate a good webinar on it here. RY can’t advise on tax-related matters for legal reasons but you should really educate yourself on this before you leave as qualifying for it can potentially pay for your entire trip.
FOLD OR CRUMPLE?
Assuming toilet paper, definitely crumple. Assuming clothes, roll tightly. Best way to pack.
FAVORITE WORDS TO LIVE BY?
“Get busy livin’ or get busy dyin’” - Andy Dufresne
ANY FINAL THOUGHTS FOR SOMEONE CONSIDERING APPLYING TO REMOTE YEAR?
Yep. If you’re like 90% of the Muggles out there you’ll talk about it, apply and then invent excuses why you can’t do it. Don’t be a Muggle. Be a freakin wizard. Just sell all your crap and go. Your life is not going to get any less-complicated a year from now. I recognize not everyone has the circumstances to be able to do this program but if you are in that lucky group who does, just take the leap of faith and go. If you want it bad enough you will figure out a way to make it happen and you will celebrate it as a great decision a year from now.
Also, there are wide swings of up’s and down’s during the course of this adventure - it’s definitely not all roses. But here’s the great thing about this: if your life is a sine wave, don’t you want to flatline or do you want max amplitude to have greater breadth of experience? The highs will give you impossibly unique memories and stories that will be your treasures forever. But even the lows (as much as they suck at the time) are actually a gift in that they give you appreciation for what you already have. And what better way to amass wealth than to have your “currency” be instantly worth more than it was before? You’ll get an immense amount of perspective during this year.
Also I talked about the concept of “parallax” as it relates to travel in my Belgrade video. Moving your point of reference repeatedly only makes you stronger, more resilient and shows you what’s truly fixed & constant in the world and which pieces are moveable. It 100% broadens you as an individual.
If you want to get a flavor of some of the places we’ve lived and worked, I’ve been good about posting a video on my blog in every city. I also put together an aggregator site that syndicates the posts of all the other Remotes and is a great way to keep up with what everyone is up to across the Remote Nation. Good luck if you’re applying and I hope to see you at some point on a future cohort via the Citizen Alumni Program they just announced. cheers.