Sep 24

Crete week 2 recap:

We find a beach where the water is impossibly blue.

But to get there we have to share this single-lane dirt road with some Cretan mountain goats. Crete doesn’t believe in guard rails and these goats don’t believe in road rules so it makes for an interesting car ride.

@benlakoff and I finally get our Oura rings. I propose to it immediately on the beach (she says yes). Feeling quantified AF now.

Next day we find this gorge with a waterfall. It was gorgeous.

Jon-o decides he’s going swimming but enters by doing a Triple Lindy off the rock ledge.

We drove to the western most point of the island and get there just in time for sunset.

In spite of applying half a bottle of SPF 1000 I’m a potato crisp (thank you Irish genes).

After dinner that night I get replaced by a mannequin. It’s more photogenic and gets less sunburned.

That’s fine though because I discover the Greek dessert Kataïfi and commit to ordering my body weight in this sugary walnut goodness while we’re here.

It just means daily TRX sessions which i have zero issue with given the view.
In summary, Crete is pretty fantastic. Good food, good people, good times. For more fun check out the Pagely podcast we just launched: (at Kournás, Khania, Greece)

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Sep 17

So first week… lemme recap:

We’re staying in what appears to be either a new or newly-remodeled triplex compound on the island of Crete.

2nd day we’re exploring the 4000-year-old palace of Knossos which apparently is the oldest ruins in the oldest civilization in Greece. It’s really old.

They’ve got old jars. On the one in front you can see the thumbprint of its creator on the handle. A 4000-yr-old thumbprint!

There are some really old paintings like this one but most burned in a fire ~1300BC. It’s a stone palace but a) all the columns were cypress trees covered in plaster b) the floors were wooden c) they were using olive oil lamps. Doh!

This is the place where the mythical Minotaur was allegedly underground in the catacombs. Turns out that was just a misinterpretation of a weird procreation screening ritual that involved grabbing a bull by the horns and jumping over it. If you couldn’t then… you didn’t. We didn’t find any Minotaurs but we did find the oldest known throne.

It’s crazy to imagine people living here 4000 years ago. They even had flushing toilets. My Airbnb sometimes don’t even have those…

Anyways this peacock shows up like it owns the place…

So we left and went to dinner at a bombass restaurant called Peskesi (highly recommend).
This is the view off our balcony. Not mad about this for a month. Opa! (at Kournás, Khania, Greece)

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Aug 02

As far as an update on the professional front, I’m still with Pagely having just celebrated four years with the company. It’s been a great experience starting a fairly early-stage (employee #8) helping grow it to a 42-person company. My role has morphed considerably from what it was when I first started. I’ve been lucky to extricate myself entirely from the day-to-day operational sales role into primarily a strategic one nowadays. My
trajectory with the company has gone from their sole sales/marketing person -> sales director -> growth hacker marketing commando and I’m now transitioning into a fourth phase as content producer having produced a bunch of different stuff. I’ve begun doing educational webinars, booting up a podcast and conducting video case studies with our customers. Historically the our biggest deals have come not from advertising nor marketing but via well-established relationships and the thinking here is that these endeavors will be a way to advance that cause at scale. I will let you know next update how that bet
plays out.  

In terms of my side hustles, I’ve just minutes ago interviewed my 30th guest(s) for Nomad Podcast and have amassed a solid repository of advice and experience for people seeking to take their lives abroad. The weekly podcast is designed to work in conjunction with the course I developed which supports the same goal of facilitating the transition to a location-independent existence. The root motive of the project is two-fold: 1) to develop a source of passive-recurring revenue that covers my living expenses while simultaneously 2) working in alignment my Simon Sinek Why of helping others to beat gravity so they can be free to do what they’re born to do.  The Nomad properties are an important project to me. This post explains why if you’re interested.  

I hit a key milestone in episode 22 of successfully outsourcing all the production work involved in delivering the show (about 5hrs per episode). I now have a guy in Macedonia who does all the grunt labor for $12/hr. That process of extricating myself from the operational grind and delegating that work should pay dividends once it comes time to implement the same for Pagely. Gaining leverage via delegation and automation has become a recurring theme. Mastering this skill and then teaching it to others I believe is part of my path.   

Personal-growth-wise the achievements I’m most proud of this past six months are improving my skills significantly in the sport of kite surfing, notching up the quality of the podcast in all respects and adhering fairly consistently to a morning routine. Being on Europe hours gives me the mornings free and my full routine at this point consists of a gratitude journal, doing the Sam Harris Waking Up meditation, Wim Hof method, alternating between TRX & minimalist running, cold showers and intermittent fasting. I’ve found this combo of activities gives me an optimal state to be at peak output most days. You can find discussion of this routine in a recent interview I did for The Maverick Show here.  
We did a Charity Makeover back in May after the last Nomad Cruise and built out some useful digital assets to support a couple local causes. In thinking about what’s next once Pagely runs its course I’m intending to channel my energy into turning Charity Makeover into a global movement similar to Startup Weekend. If I’m successful in lobbying Pagely to sponsor me in that regard it may happen sooner than later but ultimately I believe this is where I can create the greatest impact and contribution to society.   

Per the subject line of the email I’m currently in Martha’s Vineyard on my last day of vacation with my parents celebrating their 50th wedding anniversary. I was lucky to sit down with them just now and interview them jointly as my 30th guest(s) for the podcast. If you’re interested in hearing about their 50-year journey together be sure to subscribe. They will be episode number 30 airing Sept 9th and you can subscribe via any platform using the header link of this page.  We talk about how they met in the Peace Corps in
Venezuela, building the law firm in the early days of Phoenix, AZ, their respective professional careers and the immigration issue facing the US.

With each of my guests I always end the podcast by asking a series of standard questions. I’ll now start a tradition of answering these below myself and plan to incorporate this practice in my semi-annual updates going forward. The scope with me is obviously constrained to the past six months instead of the lifetime frame that I ask of my guests:   

Most influential book: Super Thinking & Sapiens. Super Thinking is along the same lines as Charlie Munger’s “Seeking Wisdom
and teaches 600+ mental models for improved thinking and decision making. Sapiens is history of humankind delivered in an engaging format and should IMO be the text book for history in high school. Super Thinking was powerful but a lot to digest – I’m now in process of converting the 650 mental models into spaced repetition cards via this app.  

Gadgets: ZoomH6 and Zhiyun Smooth 4. The Zoom is compact device I use to capture high-quality audio for the podcast interviews and is excellent at what it does. The Zhiyun Smooth 4 is a stabilized selfie-stick I started using to shoot the video trailers with podcast guests starting at episode 24.   

Movies: Winter on Fire. I haven’t watched many movies lately but this was a powerful documentary on the revolution in Kiev Ukraine back in Winter of 2014.  

Music: Wookiefoot & this 90’s playlist. Wookiefoot was a discovery that came via my Spotify Discover Weekly list. Try this
first and if it resonates just put them on shuffle and listen to all their music because it’s all excellent. I don’t know how to classify their style but they remind me of Phish meets Flobots meets a bluegrass band using sitars, tablas and other ethnic instruments. They have some really thoughtful lyrics that grow on you over time. For the 90’s music I went down a rabbit hole one day constructing a playlist of a bunch of 90’s songs and 235 songs and hours later I created arguably the most exhaustive song list of tunes capturing the music from my college years.  

As amazing as Lisbon has been as a place to live I have yet to establish deep roots community-wise there so there is no telling where I will be for the next
update but I will keep you apprised of my unfolding journey and plan to email you again in early 2020 (BTW how the heck are we more than halfway through 2019??). At any rate thanks for your continued interest in my weird life. If I can help with anything you’re doing don’t hesitate to reach out (and/or just to say hello). If you do subscribe to the podcast any rating or review you can leave greatly helps grow the audience for that and thereby supports the goal of that project.


PS. if you’re on Instagram and want to keep up with my travels I post  pics regularly here. Below is a photo with my folks earlier this week at Farm Neck Country Club in Martha’s Vineyard.

Aug 01

My brother and I grew up going to the Vineyard every summer as kids. This place hasn’t changed in the 18yrs since I’ve been here- it’s still a magical place. This is the cottage campground in Oak Bluffs in early morning. (at Oak Bluffs, Massachusetts)

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Dec 14
sitting here Friday evening overlooking the ocean in Fortaleza in my last night in Brazil before heading back to AZ for the holidays. Justin you had subscribed to receive my biannual recap of notable events over the past six months. This is that recap.

Nearly a year ago I moved to Lisbon, Portugal and have been living there since. After having done nearly two years of constant nomadic travel it’s been nice to finally plant in one place for awhile. I had done a travel program called Remote Year which allowed me to work remotely and took me to a total of 18 countries over the course of a year. I’ve been
continuing my role for Pagely as Director of Sales working out of the RY workspace in Lisbon for the past nine months. This has allowed me to meet nine other Remote Year groups that have come through Lisbon and I’ve gotten to be a steward of Lisbon to those people.

The best analogy I can give is that previously I was in a stream of people flowing through a bunch of interesting places. Now I am the rock in the city of Lisbon with a stream of interesting people constantly flowing past me in the workspace. People who sell everything and commit to a year on the road are inherently interesting people to me and it’s
been a unique privilege to meet over 400 of these folks since February.

Over the holiday break last year I created the Nomad Prep eCourse with the goal of demystifying the transition to a nomadic lifestyle and thereby making it more accessible to others who want to make this leap. The course has to date served 90+ students and helped many people prepare to take their job on the road. I realized early this year though that I had committed a typical entrepreneurial mistake in building a product before I had built an audience. To solve that issue in April I launched
Nomad Podcast as a platform to interview nomads, founders and domain experts to both disseminate useful info while simultaneously creating a fountain of prospective students into the course.

The podcast has had a total of fourteen guests so far and I’m proud of the high-caliber content there. I paused the effort however last month because it requires a significant time investment and is not yet delivering the results in terms of paying students to justify that investment. I intend to “reboot” it eventually but with limited spare cycles I believe my time for the nomad stuff is better spent figuring out a different
way to drive enrollments. My last interview inadvertently sold me on a program for solo-preneurs as a methodology for “building the audience before building the product” and I’m currently taking that course and implementing ideas there towards building and serving the prospective nomad audience.

You might ask, “why spend so much of your spare time encouraging the nomadic lifestyle?” I have two motives:

  1. The Remote Year experience was probably the single most-transformative thing I’ve ever done. I have a theory/hallucination that helping to usher more people into that lifestyle transition could unlock & awaken others and recover a few of the Lost Einsteins as it did for me. You can read more here about that theory but that’s motive #1.
  2. I have a goal to have all my living expenses covered entirely by passive-recurring income
    by end of 2019. This podcast episode struck a nerve with me and my takeaway was that the most high-leverage thing we can do is not to marginally optimize our retirement investments but rather to set up a side hustle that produces income on auto-pilot and requires low-maintenance. There are undoubtedly other side businesses which could be easier and more lucrative to start but this is the effort I’m most passionate about so I’m taking the hard road here to try and figure out a profitable model that also accomplishes motive #1.

Speaking of podcasts… I’ve rediscovered this medium in the course of building
my own and I’ve become a big fan of ingesting new ideas in this way. This is my OPML file of the shows I currently listen to. Podcasts are great as a medium (especially for runners) as they allows you to consume all kinds of current, interesting, themed content in audio form.  

In October I did a 30-day plant-based challenge based on this interview on my podcast. Since then I’ve become what I would call a “fair-weathered pescatarian” having added fish and seafood back into the mix but keeping beef, poultry and pork out of the diet. That said, if you put a Christmas ham or Kobe beef serving in front of me, I have zero issues with taking that down ;-) Overall the decision to go pescatarian was largely a function of seeing this talk by the Dr. behind His talk, titled “How Not to Die,” presents compelling evidence-based arguments for switching to a completely
plant-based diet. I’ll report back after more track record. If you’re considering testing out this switch yourself I highly recommend the 30-day challenge from my podcast guest (linked in her interview above).

As far as my work for Pagely, I just finished writing up my annual “State of the Union” summary for our sales department recapping everything we’ve accomplished over the past year. In all it was a lukewarm year revenue growth-wise compared to last year but our team executed a number of important strategic projects which should set us up for success in 2019. I appeared as a guest on a few podcasts, did this talk in Lisbon and received some good press for the novel approach I developed and deployed applying the concept of “scaling personal attention” via interactive video. I’ve been with Pagely now for 3.5 years and intend to see us through an acquisition before transitioning to whatever is next.

On the topic of what’s next: I feel drawn to a project I had started and dabbled with called Charity Makeover. Our Remote Year group executed this event and it was one of the most satisfying things we did. After Pagely I foresee working at least part-time to turn that into a movement similar to Startup Weekend. I’m now reaching out to some people I believe could be linchpins in making that happen and putting a revenue model around it that would enable it to be a self-sustainable effort.  More to follow but a small group of us are intending to finish what we started for and treat that as a pilot of this initiative.

Learning-wise I’m taking a few different eCourses as time permits. I’ve been doing this Udemy course to learn the music DAW Ableton that I see as enabling incredible possibilities for live improv. My hope there is to become proficient enough and to secure a resident monthly gig in Lisbon at one of the live music places for fun and to scratch the musical performance itch. I’ve done the Headspace Meditation program for nearly three years now and feel like I capped out in terms of
advancing my practice via that app. I trialed the app for meditation but found the narrator to be too annoying and ultimately went in search of another program for guided meditation. I ultimately settled on this program after having listened to a bunch of his free guided
meditation podcasts. Jury is still out on whether this helps take that practice to the next level but so far so good.  I’ve been devoting more time to developing my chess game. has some pretty fantastic tutorials and gives you personalized analysis of your past games (pretty slick you load in the chess notation of your past games and it steps through your game and offers advice). I picked up this snazzy robotic chess board which allows me to play with physical pieces against the AI and then analyze my chess game after the fact to learn from mistakes (yea I’m a huge nerd). I also got one for my friend Benny for his 40th b-day which in theory allows us to play each other remotely over the internet although I’m now mobile for the next few months so that will have to wait until March.

In terms of recs for various books/music/gear:

  • This is my Spotify playlist of music that’s resonated ever since I finished Remote Year. It’s a smattering of very different music but there are some gems in there.
  • For books, Principles, Power of Habit & Man’s Search for Meaning would be my top picks. I just finished one called Shadow Divers too which is a fascinating nonfiction account of a dive team’s efforts in discovering and identifying a missing German U-boat from WWII. You can find my Goodreads profile here with all my reading recommendations.
  • Gear-wise the item that’s hands-down had the most ROI for me this past year has been the TRX suspension trainer. I’ve used this in place of a gym membership ever since my gym in Lisboa pulled some shady stuff in June and it’s been a great way to stay in shape. It works great in conjunction with this app for getting an exercise regiment complete with videos showing how to do each exercise and it tracks your progress through the 12-week program. Highly recommend.

In the relationship department I am still single having had a short-lived but intense relationship with one of the participants of the RY Kanyini program. The blessing and curse of this nomadic lifestyle is that while it exposes you to a bunch of amazing people, you’re perpetually saying goodbye to everyone and relationships are destined to be short-lived. I tried my first
“life coaching” session which yielded the assessment that love is the one “broken spoke on my life wheel.” Maybe so but I couldn’t bring myself to continuing the life coaching thing after the initial session because it just seems like the people who become life coaches are the ones who don’t know what to do themselves.  For better or worse I have to feel someone is an authority on a topic before trusting their expertise. I may give it another shot at some point but for now I’m content to execute for Pagely and my own side business initiatives and do a bunch of kite surfing in the process.

Anyways, I head back to Phoenix, AZ tomorrow to hang out with my folks and friends there for the next two weeks around Christmas. I’ll then be continuing on to Mexico City for New Year’s, La Ventana for what I hope to be two full weeks of kite surfing, a wedding in Cabo, 2 weeks in Puerto Escondido, 2 weeks in Bucerias for kiting and then a quick reunion with some
folks from our RY group in Sayulita, MX before returning to Lisbon in March.

If you’re in Phoenix come join us at this happy hour next Friday and let’s catch up in person. And if you listen to podcasts I would be hugely appreciative if you take a sec to subscribe and review mine. Happy Holidays to you and your fam and I wish you a healthy and prosperous 2019.


PS. if you’re on Instagram and want to keep up with my travels on a more frequent basis I post about a photo per day of something interesting and unique from my travels here.
Below is a pic of a magical moment at sunset in Pipa Brazil last week.

Jul 24
Howdy Drew,

You had requested my semi-annual update of what I’ve been up to and it’s that time to fill you in but before I do I have a quick favor to ask: 

I just last week launched this podcast with the goal of helping 100 people get “unstuck” by demystifying location-independent work and making it more accessible. It’s received great reviews thus far but I need your help: I’m trying to crack into the New & Noteworthy Travel section of iTunes because that jumpstarts listenership. I have one shot this week to make it and every download and subscription helps towards that cause. 

If you could take 30 seconds to subscribe & download my podcast via iTunes that would be massively appreciated. If you don’t use iTunes you can visit the link above and get it via any of the other major platforms like Spotify or Google Podcasts using the link in the header. I’ve poured most of my free cycles into this effort over the past few months and have been fortunate to get some really high quality guests for the show. 

Today’s guest is my friend Andrew Hyde, founder of Startup Weekend, cycler of a bicycle across the US, moderator of TEDx Boulder, wearer of a huge beard, traveler of 80 countries now banned permanently from Nepal (find out why) and all around teller of amazing stories. Check out his episode here and keep reading once you’ve subscribed. 

No seriously. Subscribe now. I’ll wait ;-) 

Scroll down for my update once you’ve done that… 

Oh and maybe tell just one friend who has talked about the idea of taking his/her job on the road about the podcast. This is a direct quote from a girl who heard it who just reached out to me: 

Hey Sean, I just listened to your latest video with Eddie. Just wanted to let you know I really enjoyed it! I think it’s valuable for current remotes, premotes, and definitely inspiring to people who haven’t yet taken the leap and deciding to do this crazy adventure (or something like it). I love the realness of it (and I also like that it’s not directly correlated with RY… it feels more believable this way and less sales-y) I’ll be sharing this around. Hope you get some traction man. You’re going to change so many lives out there!!

It would be amazing to eek into the featured Travel section on iTunes and I’m calling upon all my connections today to execute this “thunderclap” of concentrated interest. Apparently the secret to getting featured is the velocity of downloads within a short time-frame and now is that window. Anyways mucho appreciated if you dig the cause and are able to help spread the word. 

Alright. Thanks for that. So now I’ll fill you in on what I’ve been up to since my last update in January: 

 February 6th I moved to Lisbon, Portugal and have been living here since. This city captured me when I was here two years ago as a part of Remote Year and it has my heart. 

 March was cold and rainy. It rained for three weeks straight so not much exploring but I met some amazing people in the Remote Year Excelsior group that month who I’ve continued to remain in contact with. 

 April brought the Sisus of RY and they were my favorite group yet. It was sad to see them leave but likewise I’ve remained in contact and will undoubtedly regroup with these people at some point. 

– In May my folks visited Lisbon and I saw them for the first time since leaving the US. We had a blast while they were here. While they were in town on May 21st after 10mos of hoop-jumping I secured a residency permit which now allows me to live and work indefinitely here and I couldn’t be happier. 

– I lived in Barcelona Spain for the month of June with my friends Trevor and Trish (Trevor was actually my first guest on the podcast). Midway through June I skipped out to Mallorca to surprise one of my best friends for his 40th bday. We then had our 1 year reunion since completing Remote Year in Prague. It was amazing to see 30 of the 50 people who finished the year return to Prague to reunite. Like with any good friend it strangely seemed like no time had elapsed with our friendships. 

– I’ve begun burrowing into the local tech startup scene here in Lisbon and am now the newest mentor for Startup Lisboa and coach a handful of their startups on growth marketing and sales strategy.

– I gave this keynote talk two weeks ago for the Canopy City entrepreneur demo night to share my experience of systematizing the sales process at Pagely. The 7-step framework I show in that talk is a universally-applicable methodology for any growth-stage business and I hope will help other entrepreneurs with a promising product through the challenge of bringing it to market in a more reliable way. 

– Nomad Podcast was a project I started after building and launching my Nomad Prep eCourseover Christmas & New Year’s break earlier this year. I realized after expending a ton of energy to develop the eCourse that I went in with no real strategy for gaining distribution outside of Remote Year. The podcast is a logical extension of that effort to reach a broader audience and embodies the advice of “create value first then harvest some small percentage of it.” I wrote up this blog post over the weekend to explain the motive and why I’m spending all my spare cycles pushing the nomad thing. The short answer is: I believe the “Lost Einstein” phenomenon proposed by a NYT piece is actually at work in adults as well and that an antidote that worked for me is the stimulation that came via this nomadic lifestyle change. 

– In July one of my good friends (who happens to also be the CEO of Pagely where I work) visited and we drove a really fast sports car from Lisbon to Madrid to see one of my favorite bands Pearl Jam. That was a bucket list experience for sure. 

– This past weekend I finally got back into the sport of kite surfing and purchased some gear to be able to do this the rest of the summer season here on the beaches south of Lisbon. This was one of the items on the 10-year plan I made shortly after New Year’s and I’m super stoked to finally be making that a reality. 

– I’m now packing for a 10-day working trip in Hossegor, France with one of my oldest friends and his family. My role at Pagely has evolved nicely and I’ve been able to extricate myself from much of the day-to-day grind and move into a more play-maker role of planning and executing projects that support our sales team in achieving their revenue goals. 

– I have half a dozen interviews I’ve recorded for the podcast now which I’ll be producing and releasing as time permits over the next few weeks. It’s a bit surreal to film an interview from Barcelona with someone in Bolivia and find yourself later on a plane over Lisbon sculpting the content that then gets released from a surf town in France and eventually winds up in ear buds of someone I may never meet in who-knows-where… It’s both completely normal now but mind-blowing at the same time. 

– I believe crypto currency has turned the corner in its 6mo correction and we’ll see it making a rally from here. It may falter for another month but I suspect we’ll see another massive tidal wave of interest as Wall St and institutional money pours into the space. If your investment portfolio currently has no crypto in it I encourage you to first watch this video by the one and only Andreas Antonopoulos so you understand why censorship-resistant money and blockchain is so important and then carve out even just 5% of your savings and investment portfolio and allocate it to a handful of the top cryptos. Gemini and Coinbase are the two exchanges I recommend (Gemini is unfortunately not available in Arizona nor Portugal). 

– As far as plans for the rest of summer, I’ll be in Lisbon likely until November at which point my current plan is to migrate to warmer temperatures maybe at a beach town in Mexico. I’m hoping to spend Thanksgiving and/or Christmas with my folks and potentially my brother’s family in San Francisco. Other than that no plans to return to the US at this time. I should be in La Ventana, Mexico for two weeks in January then back to Lisbon next year. If you are ever out this way please drop me a line and let me show you around this wonderful city that has completely captured my heart. 

If you’ve read this far, thanks as always for taking an interest in my weird life. I hope you and your family are doing well. Send me an update on what you’ve been up to when you have time and live epicly. 


PS. if you’re on Instagram and want to keep up with my travels on a more frequent basis I post about a photo per day of something interesting and unique from my travels here. Below is a pic from this past weekend kite surfing with local friends in Fonte da Telha, Portugal.

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