Jan 05

Sawasdee krab from Koh Tao, Thailand. 

This is my semi-annual impersonal update email to friends, family, acquaintances and strangers in which I recap learnings, failures and events of significance in retrospect. If you want to read my past updates they’re posted at the bottom of this page

I’ve been living in Thailand the past few weeks with some amazing people who are still traveling following the conclusion of the Nomad Cruise. 250 of us location-independent workers took a large cruise ship from Athens to Dubai via the Suez Canal / Red Sea / Indian Ocean and then continued to travel to Bangkok, Koh Tao and are planning to hit Bali before disbursing and returning back to our respective homebases. 

I’ll now recap some of the stuff I’ve experimented with and learned from this past year. This is all stuff I think could be helpful to others. It’s divided up into these sections and is a 5min read @300WPM: 

  • Personal growth-related
  • Professional growth-related
  • Books
  • Films
  • Podcasts
  • Hacks
  • Goals

Personal growth

2019 in retrospect was mainly about finally integrating into Lisbon and acknowledging that the “Lisbon experiment” is a long-term one. I’m happier abroad than I was living in the US. It’s a weird thing to come to terms with that I’m an expat with no intent on coming back and this decision means I don’t get to see a lot of my close friends and family but I believe those who have the latitude to be able to choose where they live should deliberately settle in a place that amplifies them and Portugal does that for me so I’m planning to keep it as a homebase indefinitely and continue to explore the rest of the world as work and residency requirements allow. 

One thing I developed this past year was a solid morning routine. Having followed Tim Ferriss for awhile I’ve known that many successful people swear by developing strong habits around getting into an optimal mental state early in the morning and then driving their day via staying focused on high-leverage tasks they dictate vs. being at the mercy of inbound email & social media. I fully drank this kool aid this past year, experimented with various practices and finally settled on a sequence of activities which works well for me. I was interviewed on Tomas Lau’s blog about it and you can read what all is involved but basically I do: 

  • a 25min meditation (variant of breath-focus) 
  • 5min gratitude journal practice
  • 20min Wim Hof method on alternate days 
  • TRX or run (alternate) 
  • Cold shower 
  • Anki spaced repetition cards

If I do the full thing it takes around 2hrs. The European hours work nicely giving me most of my mornings free since Pagely’s core team is largely west-coast business hours.  A useful epiphany that was helpful early on when the meditation practice felt frustrating was the realization that wandering thoughts are actually useful in the way that weights at the gym are useful: they provide the resistance training that allows you to refine the practice of observance and dismissal of thoughts. It’s a simple yet profound and liberating realization that broke the mental gridlock and enabled the benefits. 

Spaced repetition cards have been very useful for committing important concepts to long-term memory. I tried a number of apps and ultimately settled on the open source Anki app as it allows me to syndicate decks to friends. More on the importance of that in the books section. 

I got very serious about sleep this past year after hearing a podcast which led to me reading a powerful book which led to me buying a sleep tracker ring and ultimately prioritizing sleep as a critically-important activity. I have a bunch of highlighted snippets in my Goodreads for this book but it’s probably tied for the the #1 book I’d recommend if I had to pick one for this past year (the other one being Super Thinking – more in a bit on these). 

Professional growth

Professionally I compartmentalize my life into three realms: my full-time day job for Pagely as Director of Sales, my side hustles for passive income with the Nomad stuff I’m doing and my work on building up Charity Makeover and turning that into a movement.  

Pagely: 2019 was a frustrating year. Almost all of our gains in sales were washed by churn & contraction. It’s the first time in my 4 years at the company that we failed to add at least $1MM in ARR. I’ve got plans for addressing the leaky bucket that ate our gains and for building out a stronger pre-sales funnel to feed us more prospects but it didn’t happen in 2019. On top of that we unfortunately had to let most of our marketing team go at the end of the year. The business itself is stable and remains strong but cracking the ceiling we have right now with our monthly recurring revenue is the #1 priority. The good news is we have a very capable new Dir of Marketing and looks like we’ll be solving a hole on the engineering side that should improve product which will help on retention. There’s a high likelihood we’ll be migrating our CRM to Hubspot. I’ve been a long-time Active Campaign advocate but I’m excited to learn a new platform and roll that out for improving our top-of-funnel efforts. I’ll report on how all this plays out in next update.  

Nomad Prep/Podcast: My hope last year was to get to the point where passive income via my Nomad Prep eCourse I built could cover my living expenses. That fell way short and that course has just barely covered its hosting & licensing fees. The podcast has had favorable feedback and gotten me access to talk with and learn from some impressive people. I’ve reframed how I’m viewing this whole experiment and am at this point chalking it up as basically free expert consulting with a side benefit of raising my visibility/rapport amongst the nomad circles. I was lucky last month to be invited to give the opening keynote for Nomad Cruise X and in a meta twist, I converted that talk into a podcast episode itself.   
I have a number of interesting interviews queued up set for release in the coming weeks and I’m rolling out a multi-level affiliate program that should hopefully solve the distribution bottleneck for the course and podcast. If you listen to podcasts you can subscribe to it via the header link here. I’ve also been producing the Pagely podcast which has likewise received some favorable reviews. That’s more squarely focused on SaaS business topics and with a mix of hosts – you can find that here

Charity Makeover: My good friend Ben Lakoff (who I’m now traveling with) has joined up with me in this effort and helped organize the last event we did in Barcelona. This is currently a purely volunteer effort that’s basically a series of organized hackathons to build high-leverage digital assets for local charities to help them rise up from the operational grind and be more effective in their cause. You can read about what all we accomplished at that event but it was a fun and productive experiment. My goal this year is to get CM to a point where admins can bring these events to their cities and have the tools/playbook for conducting them effectively. We have a model envisioned for how this becomes scaleable and can be done in a fairly low-touch way while permitting me to remain performing my full-time duties for Pagely. I envision turning this into a movement similar to Startup Weekend and having it become a lever to tip the under-staffed nonprofits poised to make a real difference in their respective realms. If you’re interested in potentially running these events in your city, read more about our past events on the site then get in touch and let’s talk.    


You can find my full 2019 book list here. I’ll briefly summarize key takeaways from the ones that had important ideas: 

  • Why We Sleep – if diet & exercise are the pillars of health then sleep is the foundation upon which they rest. We are woefully neglecting the importance of sleep as a society and it’s having all kinds of detrimental effects. As the author says, sleep is the most under-utilized legal performance-enhancing drug that has no harmful side effects. This is one of two books I’m recommending all my friends read and act upon. We need to abolish this nonsense “badge of pride – I don’t sleep” work ethic BS that is rampant in the entrepreneurial communities and start prioritizing sleep as a society. 
  • Super Thinking – This is the other one that I will say is a must-read. It’s a catalogue of mental models organized and presented in a really compelling format with interesting examples to help with encoding and recall. Mental models are like design patterns of thought that can be used to “be wrong less often” and quickly make sense of novel situations. Goodhardt’s Law, Chatalier’s Principle, the Lindy Effect, Cargo Cult… these are just 4 of the 300 models that represent some replicable design pattern that recurs in places and can be used to understand and predict behavior.  This is co-authored by the founder of the DuckDuckGo search engine. It’s a book I wish I had early in my career as it gives you all these useful lego block ideas that you can use to make sense of situations and predict outcomes. I found it so important that after reading I went back and made Anki cards for about half the models in the book so I could periodically review and commit them to memory. Highly recommend. 
  • Permanent Record – this is Edward Snowden’s memoir and it’s an important work. For the people that believe he was a traitor, read this book to understand the importance of what he did and how incredibly brave and essential his work was to inform the public of unconstitutional bulk surveillance on the part of the US government. 
  • Untethered Soul – I heard Tony Robbins’ interview with Michael Singer and then read his book. I typically shun “woo” spiritual stuff but this was a powerful book. The small group of us who are living in Koh Tao the next month are doing a book club and making this the first one. I’m looking forward to re-reading it as the concepts were just at the very periphery of what I feel I can comprehend so I’m interested to reconcile initial takeaways with stuff from a second reading. 
  • Sapiens – This is Yuval Noah Harari’s brilliant work summarizing all of human history in a single book. Most people I know have read this book by now so I felt a little late to the game but this should be required high school reading and likely should replace history books everywhere. History books (at least the ones I read in school) were terribly boring and therefore ineffective at the job of getting students excited and invested in learning the subject matter. This book is a compelling safari through time making sense of the different eras and progressions. I liken it to Neil deGrasse Tyson’s Cosmos series only for history instead of science. He also turned this book into a video lecture series on YouTube – I don’t have the link handy but you can likely find it via his video page if you’re more an audio/visual learner. 
  • Principles – Ray Dalio lays out his framework for how he operates in business and in life. He built Bridgewater Capital which is arguably one of the most successful companies of all time. If you’re into systems thinking this is a fascinating read by a bright & humble individual who is attempting to package his battle-tested methods for operating what he calls “a believability-weighted idea meritocracy” (mouthful). It’s broken into 3 Acts – the last one drags on a bit and the first one is more a recounting of his accomplishments. If you have to read only one section read Act II. Very valuable. 
  • Power of Habit – I’m coming to realize that we are essentially stacks of habits in the end. Learning to program our minds and instill desirable habits is a huge advantage akin to business people who can learn to write some code. This book deconstructs the mechanics of how habits are formed and stick and then gives the method for retraining new habits. Very good read. 
  • Man’s Search for Meaning – This was simultaneously depressing and uplifting. It’s Victor Frankyl’s story of surviving a Nazi concentration camp against all odds and the stoicism philosophy that kept him alive. We can be such awful and wonderful beings- this is a powerful first-hand account of what life was like in the concentration camp. It gave me both gratitude for having to not suffer that but also respect for the mindset it took to endure it.     
  • The One Thing – I’m halfway through this one now but it’s good enough to merit making this list. This is basically fractal 80/20 philosophy that Gary Keller used to build one of the most successful real estate brands out there (Keller Williams). It advocates for relentlessly pruning your todo list to continuously find the single most high-leverage thing you can do that makes all the other activities either easier or irrelevant. It can be applied both in business but in any situation and the elegance of it is that you can decompose todo’s into pieces and apply this philosophy universally. This is a game-changer and I’m excited to apply this lens in my projects going forward. 
  • Courage to be Disliked – I read this at the recommendation of my friend Hiten Shah under a tree on the beach in Thailand. I need to re-read it because it was one of those fables with layers of meaning and with ideas so simple yet so profound that they need to be unpacked again. It’s basically attempting to make the ideas of psychologist Alfred Adler more accessible by packaging them into a conversation between a philosopher and a student. They’re easy to understand in theory but difficult to apply in practice. 


I only watched two movies I can remember this year and both were excellent: 

  • The Great Hack – shows the behind the scenes with the Cambridge Analytica scandal that tipped the 2016 US election and let to Trump winning. Huge eye-opener on the power of weaponizing data for surgical, strategic manipulation in influencing elections. With AI improving, privacy erosion, deep fake videos, fake news stories… these will be important-to-solve compounding challenges for us to resolve as a society this decade. 
  • Winter on Fire – was the story of the Ukranian revolution that was largely absent mainstream media. Very well done. I was oblivious to the strife in that country and how it narrowly escaped President Viktor F. Yanukovich pulling a fast one. Find the trailer here.   


I listen to a bunch (find my OPML file here) but if I had to boil it down to just five I’d say these: 

  • The Maverick Show – hosted by my buddy Matt Bowles this is a weekly interview with an impressive location-independent entrepreneur. Matt was on the last Nomad Cruise and he and I are perpetually mistaken for one another (two tall lanky white guys with podcasts). He gave me inspiration and tips to pursue my own podcast and does a banner job of extracting their genius and exposing actionable lessons. Highly recommend. 
  • How I Built This – NPR-sponsored interviews with entrepreneurs on how they did what they did. Very high production quality and content value. 
  • Tim Ferris Show – the OG podcaster. He’s become far less douchey as of recent and has really grown into his own skin. His guests are top-notch and I generally come away with at least one idea I can implement in my own life from each episode. 
  • Nomad Podcast – shameless plug for my own show. I’ve interviewed upwards of 40 guests at this point and have tried to draw out ideas and lessons I think can be transformative for others in business and in life. 
  • Pagely Podcast – ditto only this is the podcast I run for my employer Pagely. We are more focused on business topics but conversations tend to wander in and out of personal and professional growth stuff. There are three hosts for the show and I’m one of them. 

Hacks & Tools

These are all tools I’ve found useful over the past year in saving time/money/headaches: 

  • Skyscanner “everywhere” for flights – this is a game-changer and they have a mobile app. If you’re flexible in your travel plans you can use this to find amazing flight deals that get you 90% to your destination for 1/10th the price then you just solve the last 10% via separate flight or alternate transport method. Blablacar is an awesome ride-sharing option in Europe for covering the last leg and you get to meet interesting locals. 
  • Oura Ring – this is a ring you wear that tracks your sleep & activity and advises you on when to workout and how hard. It’s been really useful in forcing me to confront and prioritize my sleep when it becomes deficient. 
  • IFTTT – This is basically Zapier for the average person in consumer apps. You can use it to wire together disparate services and make stuff happen automatically. I’ve been horrible about blogging but I’m in a rhythm of doing weekly micro-blogging via Instagram so I setup a iFTTT that pushes my IG update to my blog under the travel category. Super useful. You can do a lot with home automation and integrate with Google sheets, location tracking, etc.  
  • Overcast & Insight Timer – two useful mobile apps. Overcast is how I listen to podcasts. I now listen to most at 1.7x and whatever tech they’re using makes it really listenable at fast speed. Insight timer is a nice free timer for doing meditation that lets you program interval gongs that aid with recentering you intermittently. 
  • Eye mask & silicon ear plugs – these two have been great for situations when there’s construction going on or the room is really bright in the morning. The eye mask is silk so you forget you have it on but it’s thick enough to completely block out all light. I tried wax ear plugs but found silicon makes a perfect seal and make it perfectly silent. It takes some getting used to hearing your own heartbeat at first but these used in conjunction have been game-changers for sleep in difficult situations. 


I have just four goals for 2020: 

  • Get Pagely past $800k MRR. 
  • Get my living expenses completely covered by passive recurring revenue from side hustles.  
  • Be able to reliably ingest and make sense of info at 3x speed of the average person. 
  • Automate, delegate and/or eliminate those things which consume my time but don’t add proportionate value to my life. 

I have other things I want to learn and do but in the spirit of that “The One Thing” book they all become irrelevant and/or easier if I can do these four things. Tune into the next 2020 half-time update to see how those goals unfold.

Thank you for your continued interest in my weird nomadic existence. Hopefully some of these learnings are useful to you. Here’s to your health & happiness in 2020. Would love to hear back from you. This is an “impersonal update” in the sense I write it once and blast it out to a number of people but I always enjoy hearing back what people are up to. Also drop me a line if you’re ever out in Lisbon and want to connect. cheers 

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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.

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 NutritionFacts.org. 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 Caraya.org 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 Calm.com 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. Chess.com 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.

Feb 01

I’m 30,000 feet above the Rockies en route to Sioux City, South Dakota on a brief stopover in the US and figured now is as good a time as any to write you a quick update email. I had originally intended to send these updates quarterly but semi-annual seems to be the frequency they want ;-)

The Remote Year program I joined back in May of 2016 concluded in May of 2017 in Buenos Aires. I never returned to AZ after it ended but instead chose to continue traveling working my way up South
and Central America via Chile, Costa Rica, Nicaragua, Dominican Republic and then making another stint through various countries in Europe. I spent the last three months living in Mexico City and the last two weeks kite surfing and working in La Ventana, Mexico.  I’m now up to a total of 61 cities, 18 countries and 4 continents in the last year and a half while still performing my role for my company Pagely as Director of Sales. It’s been one heck of an adventure.

Remote Year just last week did this piece on me and it’s a great summary of all I’ve been up to since that program concluded if you want more details.

One of the Remote Year groups that followed ours was named “Ikigai” which is a Japanese word that roughly translates to “the intersection of one’s purpose/mission/talents with what the world needs.” Late last year I took a hard look at all the experience I’ve acquired over the past two years in sales, travel, marketing automation, teaching, WordPress, writing and through this lens of Ikigai decided I was uniquely positioned to deliver an online course that would help others to make the leap and do what I had been fortunate to be able to do in taking my job on the road.

I started formulating an idea for an eCourse in October
and thought “yea I can probably knock this out in a few weekends, no problem.”  Four months later I’m *nearly* done with it (and by nearly, I mean, four months from now I’ll probably still be tweaking the content and learning management system ;-). But I’m proud to finally unveil what I’ve been toiling nights and weekends building: NomadPrep.com is the first course of it’s kind as an online academy to help the aspiring digital nomad to make a successful transition to this lifestyle.

Jul 23


Hola from Playa Grande Costa Rica!

Here is a quick update from me since my last email at Christmas. I’ve been traveling and working remotely now for the past thirteen months as a part of a group called Remote Year. My travels so far have spanned 53 cities, 17 countries and 4 continents and during this time I’ve been lucky to be able to realize a 70% increase in my sales volume for Pagely vs. the year prior to traveling. I did a lengthy write-up here summarizing the entire year in review. All in all it’s been an incredible experience. I had opportunity to speak at the PressNomics conference in April on how we’ve made this work and gave this talk which was well-received:

^ that’s a solid 30min overview of what’s been involved in making this travel/working arrangement effective over this past year. 

In each city I’ve been diligent about doing a blog post, photo album, narrated walking video and music playlist to capture the local flavor. Here is the recap of all the places I’ve been since Christmas:

Bogota in January: we flew from Mexico City on New Year’s eve and celebrated that night in Bogota, Colombia. I then did two weeks of travel all around the coast and jungle of Colombia with a friend (great pics at that link above). The latter half of the month I spent heads-down on work stuff. Elevation of Bogota is 8,500′ – was great for high-altitude training on the runs there. 

Medellin in February: was one of my favorite cities. We stayed in an area called
“Poblado” with a bunch of great little parks and restaurants. Contrary to the long-running Pablo Escobar stigma from the various films portraying Medellin as an unsafe drug capital, it was extremely safe and welcoming. Medellin is a place I could comfortably live at this point.

Lima in March: Lima had amazing seafood and our workspace there was probably the best of anywhere we’ve been. Unfortunately they had terrible floods while we were there that displaced some 20,000 people in the outlying areas. The highlight of the month for sure was hiking the Inca Trail and getting to walk around Machu
Picchu and Huayna Picchu. I left Lima early to come back for a handful of things that were happening in AZ. 

Cordoba in April: I did a 48hr travel “day” to Cordoba Argentina the 2nd week of April. Cordoba was a nice “rest stop” before Buenos Aires and after Lima in the same way that Valencia, Spain had served that same role between Rabat and CDMX.  The highlight in Cordoba was the work we did via the Charity Makeover effort I started to help a local monkey sanctuary. I remain actively involved in that effort today helping transition the project amongst Remote Year groups that are still flowing
through that city each month. 

Buenos Aires in May: up there with Lisbon, CDMX and Medellin as one of my favorite cities Buenos Aires was our final month in the program. The last month was a whirlwind with a side trip to Iguazu Falls (incredible) and all the goodbyes and farewell parties. Argentina just yesterday announced a promising plan to put it on par with Chile in terms of making it friendlier for Entrepreneurs to start businesses. I have my eye on BA as a potential place to return if/when I start the next thing following the successful exit of Pagely.   

After Buenos Aires I did a trip with a friend to the wine country of Mendoza, Argentina en route to Santiago, Chile where I spent the last three weeks. I arrived in Costa Rica three days ago and enrolled in a week-long surf camp here. Unfortunately yesterday I broke my toe which will likely put a damper on my surfing lessons. Fortunately I was able to get up on the board twice before the toe incident. I’m intending to move north to Nicaragua in a week and then meet one of my oldest friends in Dominican Republic for kite surfing all of July. Our old drummer for Cold Turkey is getting married in Seattle in early August so I’ll be back
briefly in the States for that then (provided I’m not exhausted) bounce to Europe for summer and ultimately plant in Mexico City around October. 

If you want to read the massive recap I did this is the single best summary of everything. I always enjoy hearing from people especially when on the road and isolated from friends. Drop me a line when you have time and let me know what’s new with you. I’ll part with this photo I took last night on the beach of Playa Grande at sunset. It’s beautiful here
right now. I hope you are keeping cool this summer and look forward to hearing from you. 


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.

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