2019 Annual Review

Every year since 2016, I’ve been doing a “Personal Annual Review.”

I’ve outlined the process in a blog post, but historically these are all safely stored for my personal use only and rarely shared.

Starting this year and going forward, I shared this review with my email list and later am posting a more truncated version on my blog.  

Why share? Well, I think there is a great power in asking for help. By sharing what I’m working on and learning, perhaps I can help someone else going down a similar path.

These reviews always have a bit of a recency bias, but I try to keep it relevant for the year. Either way, a lot happened this year.

So, enjoy. As always, open for feedback and comments - love to hear from you people.

General Life/Location Update

It’s 29-January-20, and I’m currently in Koh Tao, Thailand.

I’ve been back in Thailand since mid-December, which was my first time back after nearly 2 years after moving away from Bangkok. Feels great to be back and see some familiar places as Thailand was ‘home’ for nearly 3.5 years.

Currently, I’m with a group of “Digital Nomads” (hate that term), who are all still traveling together following the Nomad Cruise. Around 250 “location-independent workers” or “Digital Nomads” took a 17 day cruise ship from Athens to Dubai via the Suez Canal / Red Sea / Indian Ocean and then continued on to Thailand together. The Nomad Cruise is basically a conference at Sea - filled with a lot of learning and fun (and acro).

The plan after Thailand is to head to Bali, Indonesia starting on 6-Feb for 2 months, and then it’s a big ?? on where to go.

I do know, however, that I have plans to see my new baby niece (“Baby Yoda” if Indy gets his way…) AND (be the minister in) my baby (bigger) brother’s wedding in June. So in 2020 I'll be around in the US. I’ll likely stay in the USA straight until after Burning Man 2020 early September… I mean, I can’t miss that now can I.

Some Favorite quotes from the year:

"The unexamined life is not worth living" - Socrates

“All the returns in life, whether in wealth, relationships, or knowledge, come from compound interest.”— Naval Ravikant

A bonus quote I got from Ryan Holiday’s The Daily Stoic (16-Jan):

“Never do anything out of habit”….“…we are studying philosophy precisely to break ourselves of rote behavior. Find what you do out of rote memory or routine. Ask yourself: Is this really the best way to do it? Know why you do what you do - do it for the right reasons”


From a growth perspective, I read a lot more this year. This is partially thanks to Audible, which allowed me to read another extra 18 books alone by using this app. I was always skeptical about retention when “reading” a book by listening to the audio, but honestly it’s not that bad.

Post-University, I’ve been quite a reader. However, recently I’ve changed my mind on reading a bit.

Inspired by Naval Ravakant in that I don’t feel compelled to read from front to back, or finish books that don’t resonate with me. This was a total epiphany that I don’t have to finish a book that I don’t want to… Who knew? So easy. I ended up writing a post about it here: https://www.benlakoff.com/reading/

I tend to spend a lot of time ingesting new content. Jumping to a new book immediately after finishing another. However, I recognize that more time should be spent digesting. As with everything, it’s quality > quantity.

In 2019, I found myself re-reading GREAT books like: Sapiens (an absolute must read if you haven’t already), or Tools of Titans… and finally cracking some books that have been on my list for a long time such as Atlas Shrugged and Dune (oh yea).

I also journeyed a bit outside of the normal reading lists that I frequent, adding books like The Multi-Orgasmic Man, How to Change your Mind (Psychedelics), How to Love, and The Untethered Soul.

Some other favorites (business books) that stick out were: Expert Secrets, When Coffe & Kale Compete (Jobs to be done framework), SPIN Selling, and 80/20 Sales & Marketing.

I’ve actually signed up for GoodReads in December, so I’ll track my books there. Great app, I actually only have 2 friends - it’s a sad social media. Add me? https://www.goodreads.com/benlakoff

Overall, my top 4 recommendations for books this year would be:

  • Super Thinking - A book all about different Mental Models - what they are and how to identify them. I’ve tried to read books like this before, but this one was really good. Recognizing these can start to allow you to "be wrong less often" and quickly make sense of novel situations.
  • Awareness by Anthony de Mello - A short book, and not easy to get through. Mixing western and eastern spiritual thought, I find myself going back to it from time to time to reread. De Mello argues that “life is easy only if you let go of your attachments, cravings and illusions.” You’ve got to drop the labels and you’ve got to understand that the negative feelings you experience are in you and not in the external world around you. Until you drop everything, you can’t experience happiness because true happiness is uncaused unlike excitement. After his death in 1987, de Mello was censured by the Vatican's Defenders of the Faith and consequently, his books are not allowed to be sold in official Roman Catholic bookstores. How about that for marketing?
  • The Daily Stoic.  This is such a palatable entry point into Stoicism, something that I’ve embraced more fully in 2019. The three most essential parts of Stoic philosophy: Control your perceptions, Direct your actions properly, Willingly accept what's outside your control. Another great read about Stoicism is “A Guide to The Good Life.”
  • Why we sleep. Going into great detail on the Importance of sleep. Completely changed my mind and got me to buy the oura ring in Aug’19. You can also check out Matthew Walker’s Interview on Joe Rogan as he goes into many of the main points, highly recommended.

Something new this year…. I’ve shipped 3 (of my favorite) hardcover books to my Mom & Dad this year. I’ll actually be sending out other books to my brother and sister, books that impacted me that I think they’d appreciate. We’ll see how it goes :)

Helpful Tools

Some things I found interesting this year include:

  • Mute Background Noise During Calls with Krisp (for Desktop). It’s amazing, seriously.  An absolute must if you frequently make work calls in Noisy environments. It’s creepily good at this. Use my link and you get 30 days free.
  • Zero Intermittent Fasting App. I’ve been consistently Intermittent fasting for the past 2 years, and this app is simply amazing - it’s Free, simple, and great. I fasted 2200 hours in 2019, typically 2-3x per week for 18-20 hours each fast. Apparently it’s healthy and will make me live longer.
  • Blender. I mentioned this in Sean’s Podcast, but this is the best travel hack I’ve found. Buy a blender and ship it to the AirBnB you’re staying in. Instant smoothies every day for breakfast (need to email them first to see if they have one, so you’re not just buying blenders). My daily smoothie is packed full of: Whey Protein, Mixed Fruit, Avocado, Kale/Spinach, Peanut Butter, Almond Milk, Spirulina and Coconut Oil. It’s probably 1,000 calories of delicious goodness to start my days (if I’m not fasting).
  • Oura Ring. After reading Matthew Walker’s “Why We Sleep” I panicked and bought the Oura Ring sleep tracker for 2H19. It’s a great little tool and helps me prioritize sleep and not lie to myself (data doesn’t lie). It actually kinda makes me freak out about my sleep, just a bit.
  • Loom Screen Record. By far the easiest way to quickly record something on your screen and share it with someone. I’ve been using this with my assistant to explain a task I need accomplished. My old process was to write out instructions and add screenshots, now I just simply do a recording of what I want done and share the video.  
  • Gratitude and Meditation make a very noticeable difference in my day-to-day happiness. I use the Five Minute Journal for Gratitude and Oak App for Meditation. I tried out the Sam Harris Waking up app (and meditated for 50 days straight), but ultimately didn’t like it that much after the course was finished.


Literally in January, with my Family in Spain after Christmas, I had decided I was “done with traveling around” like a gypsy person and “wanted to move back to the USA.”

Whoops. In 2019, I spent less than 25 days in the USA this year, split into two trips. Much lower than normal, and well within the FEIE Limit.

My first trip, in April, I was able to celebrate my Grandparents 75th WEDDING ANNIVERSARY.

75 years married. They’re incredible.

It was an amazing time and great to see family I haven’t seen in a really long time. Unfortunately, this was the last time I would see my Uncle Hal, as he unexpectedly passed away shortly after the celebration. I’m so very thankful we got to spend the time we did together and especially that anniversary reunion. My uncle Hal was a lover of life, and he truly enriched others lives. There are many people that will miss him dearly, that’s for sure.

In May, for my second USA trip, I had the honor of being the officiant at my sister and Jeremy’s wedding in Los Angeles. It was a wonderful celebration and I was so fortunate to play a part in it. I was unbelievably nervous, and overall it went really well.

In June’20, I actually will be the officiant at my brother and Jenna’s wedding. What an honor. I feel so grateful that I can not only consider my brother and sister as ‘best friends’ of mine, but to serve such a role in both their weddings? My heart is exploding.

Then, in other news, I traveled a ton. Loads of countries.

In total, I went to 21 different countries this year, many times more than once. I was trying to stick to 3-6 weeks in each country, but ended up jumping around a lot more than I had hoped.

This would be my first full year of “location independence” and I was a bit spastic.

Searching for a bit more of community, I stayed in Multiple Coliving Places (favorites were Outsite in Lisbon and A Landing Pad in Barcelona), I went on 2 Nomad cruises, Tried out WifiTribe, and MindValley University in Croatia.

Here’s the Country Count

  • Spain (4x - also to Canary Islands)
  • Gibraltar
  • Portugal (4x - also to Azores Islands)
  • Morocco (2x)
  • USA (2x)
  • Czech Republic (2x)
  • Austria
  • Germany (2x)
  • Slovakia
  • Hungary (2x)
  • Croatia
  • Italy (2x)
  • Slovenia
  • Turkey
  • Greece
  • Israel
  • Japan
  • Jordan
  • Oman
  • UAE
  • Thailand

Most of these weren’t “new country visits” for me and oddly enough I counted up my total country count… I’m somewhere over 75 countries traveled to date, which is pretty wild.

Career Focus

Second full-year as a full-time entrepreneur and living without the US-sized salary. Here’s a recap of the projects I’m working on.

Intelligent Trading Foundation (ITF) - This was my startup that launched in 2017. Ultimately, we massively downsized and are trending toward full closure in 2020. We failed, and ultimately it’s my fault as the leader. I won’t blame it on the market, just execution by me as a leader. Ultimately, I truly believe that alternative assets, including cryptocurrencies and tokenized securities, are an essential part of an investor's total asset allocation. However, like most startups, we were a bit of a "solution looking for a problem."

We've struggled with product/market fit and really building a product that people love (and are willing to pay for). Normal business operations (such as having a bank account) were severely handicapped, we lost about 50% of the money raised due to cryptocurrency price downturns - selling the majority at an absolute low. From the outside, it was a massive failure in that the company failed, but personally I’ve grown a TON. My growth with ITF was parabolic - coming from such a low base. How to motivate, inspire and lead a team will always require tuning, but I wholeheartedly believe that at times you learn more from your ‘failures’ as opposed to everything going well. I’ll end up writing a bigger blog post on this one.

Alt Asset Allocation - I started a blog in 2019, and it’s more of a side thing. It’s a long slog, writing about things I find interesting in this space (and want to investigate further). Either way, writing is a skill I’m constantly looking to improve and I’m always interested in Esoteric Alternative Investments.

2key Network - What started as an idea to do some consulting resulted in a full-time role as Head of Business Development. This is a (rather autonomous) remote role for 2key, which is based in Tel Aviv, Israel. “Business Development” is about as generic of a title as possible, but most of my time is spent on Sales & Marketing automation, and plan to focus on this in 2020 - a skill applicable to any new endeavor. As an entrepreneur, you wear a lot of hats and rarely have time to fully focus and build up skills (resulting in being ‘ok’ at a number of tasks), and this is one role I REALLY want to get better at. Who knew that I never actually worked in sales? It’s great. Overall, I have a lot of autonomy with this role, it’s completely remote and with a very disruptive company - it’s a good gig.

MasterMinds - I ran a few paid mastermind groups in 2019. While I still believe they add a lot of value, they’re a ton of work. I’ll ramp up another mastermind sometime toward the end of 1Q20. These serve as a bit of ‘deal flow’ potential for me as an angel investor, plus, I really love it. Nothing is better than working through business problems with passionate entrepreneurs. If you’re interested in leveling up your business with a group of like-minded entrepreneurs, let me know and join the next one :)

Charity Makeover - This is the baby of my good friend Sean Tierney (who I'm now traveling with). I joined 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.

Our 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. Sean’s big vision is to turn 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.


I tend to prioritize health over all other areas. A healthy body allows me to be energized and focused during the day. Plus, I plan on living to be 150 years old, I wanna take care of this thing.“Mentors won’t make you rich. Doctors won’t make you healthy. Nutritionists won’t make you slim. Teachers won’t make you smart. Gurus won’t make you calm. Trainers won’t make you fit. Ultimately, you have to take responsibility. Save yourself.” - Naval Ravakant

Great Parts of 2019:

  • Meditated more consistently in 2019 than I ever have in my entire life. A serious attempt this year with probably an average of 5 days per week. This seemed to help a lot with a lot more clarity. I currently use the OAK Meditation App (mentioned above in tools).
  • Focused on having a good morning routine for probably 90% of the year (it fell through on vacation). My Current Morning Routine consists of Meditation, Gratitude Journaling, and 20 minutes of yoga.
  • Ate more veggies - First time in my life consistently making salads during the week (not here in asia, unfortunately). I try to stick to easy healthy goals, and eating more greens is one of them. A lot more cooking this year, which was a goal. From 2015-2018 I probably cooked 5 meals, the entire time.
  • Regular intermittent fasting (using Zero App, mentioned above in tools).
  • Consistent working out and much more consistent with doing heavy strength training and incorporating big compound lifts in my weeks (Squat, Deadlift). Rip those big muscles up. Oh yea.
  • I stopped drinking for 11 months in 2019, which undoubtedly made me a lot more healthy. Why not 12 months you may ask? Ego, that’s why. I outline my thoughts a bit more in the blog post.
  • Prioritized Sleep (using Oura Ring sleep tracker, mentioned above in tools) and made it a priority.

Need to Improve

  • Flexibility. As part of my morning routine I do tend to do a little bit of yoga, but I’m still woefully inflexible (in my mind). Here in Koh Tao I’m consistently stretching after the gym and trying to do the occasional yin yoga at night. Hopefully I’ll be doing the splits in no time next year.
  • Evening Routine. I still tend to be on my phone far too late. Although I started using Blue Light blocking glasses (Nerd alert) whenever I’m on my computer or looking at a screen after sunset, I’d like to turn my phone off earlier each night.
  • Would like to eat less meat in 2020. These documentaries really make a compelling case and I’ve always been more of a caveman eating a lot of meat.
  • Incorporating Breath Work into my practice. I’ve experimented around with the Wim Hoff Method, but can’t seem to get it to stick. Want to try harder in 2020. Breath work is REALLY powerful.

Wins - what seemed to go well this year? Losses - what could I have done better this year?

This section has been removed from my public version. I’ve outlined the process in a blog post, but historically these are all safely stored for my personal use only and rarely shared. The hotspots for “Career”, “Health”, and “Travel” are broken out above, but the rest aren’t really relevant for the readers and this email is getting much longer than I had anticipated :)

Overall: What obstacles have I overcome?  What did I accomplish?

Another huge 12 months.

Embraced Nomadism, swallowed the hard pill and downsized/closed my first company, opened myself to love and had a girlfriend. Pursued a clear head and didn’t drink for 11 months. Got ordained and officiated my sister’s wedding :) Checked my ego and took a very beneficial (longer-term thinking) job. Gave a keynote on Nomad Cruise, in front of over 200 people (Public speaking is always something that has terrified me). Started working with Sean on Charity Makeover, a movement that could significantly make the world a better place.

Overall accomplished a lot though. Quite pivotable year.

Overall:  What did I learn? How have I changed?

Constantly in pursuit of focus, and balance (which is impossible, I get it). Quality versus quantity in everything I do.

I’ve become MUCH more empathetic in 2019. One major takeaway from MindValley is that everyone is dealing with their own shit, their own insecurities, their own inner battles… That guy that cut you off, maybe his daughter is on life support and he’s rushing to see her, doesn’t hurt to remember this.

Talk about what you’re working on and what’s getting you excited. Tell People. Note: Despite me giving all the ‘manifest your destiny’ people a lot of shit - when you start talking about what you want to do, sometimes things fall into place as people actually find out what you’re wanting to do… Whether it’s the ‘universe conspiring to help you out’ or just humans genuinely wanting to help other humans… Letting people know what you’re working on can have powerful repercussions.

Learning for the sake of learning. Recognizing Ego and the way it makes its way into my decisions. Thinking hard about nomadism - as I don’t believe it’s sustainable long-term, especially the way I’m doing it.

Actions: Where I could use some help!

As I mentioned in the above section, I think it's important to talk about what you're working on and getting excited about. I don't do this enough.

1 - Charity Makeover. This is quite possibly the most impactful/ purposeful pursuit I've ever worked on (can read more about it in the "Career Section" above). The areas that we could use help:

  • We've spun out a corporate-focused Charity Makeover product. These charity makeover events are a fantastic Corporate Social Responsibility (CSR) move for big companies. These events have the added benefit of getting their staff out of the office for some team-building, new skill development and really is a way to inject purpose into their lives. We're looking to chat with any office that has a CSR budget.

2 - Masterminds. I love all things startups. A ‘startup’ is just a massive problem solving exercise with unlimited work – it’s just a matter of prioritizing that work so you don’t drown every day. Knowing which problems to work on solving each day is the fun part. I started running Masterminds in 2019 and got a ton of value from them.

Finally, I'm obsessed with Business Strategy and Sales/Marketing Automation. If you're needing any help in these areas, I'm happy to chat.

Overall:  How do I feel about the year?

I’ve had a picture above my desk since high school. It has a picture of an elephant and underneath simply says “How do you eat an elephant?”

I think about this often, as the answer is simply “One bite at a time.” This is how my years feel, constantly working on eating that elephant. Consistent forward motion.

Definitely progressing, maturing, growing toward the best version of myself that is possible.

2019 was really about journeying deeper within my mind and (getting closer to) finding out truly what I want / need and to stop pursuing things that I think I should want / need.

I’m still not “there”, but accepting the fact that I’ll never get “there’ and that it’s just a process. I’m growing more content with the idea of enjoying the ride as opposed to always wanting to “get there” faster.

Cheers to a great year.