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.    

Books

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. 

Films

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.   

Podcasts

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. 

Goals

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