28 Lessons for 28 Years

Well, I officially escaped the 27 club. Another candle on the cake, ring around the tree trunk, cycle around the fiery star at the center of our solar system…I’ve been able to rack up more miles on this fleshly vehicle that is my body. Cheers to that. Following up on my list from last year that was higher level insights, I’ve added some “rules for life” here that I like for their tactical nature. Here’s to continued progress and implementation. One day better, every day, for all days.

  1. When getting on a metro, wear your backpack in front of you. This will stop you from being robbed and bumping into people unnecessarily.
  2. When walking into a public bathroom, take the closest toilet, it’s been scientifically proven to be the cleanest, while most people assume it’s not.
  3. Utilize small talk as a metric in order to gauge basic evolutionary principles: is this person a threat? Anything off-putting? If they can handle a basic conversation, then they most likely will be able to interact on a deeper level.
  4. In a world of ever-growing AI, IQ is a depreciating asset while EQ is an appreciating asset. Most people listen to others with the intention to reply. Some listen with the intention to learn. But very few people listen with the intention to understand. When we do this, we can build out a map of the other person, and understand how this new information fits into their overall goals, dreams, and core values that they believe in. Hard skills can and will be automated, but the ability to truly know someone, what they stand for, and be able to relate to them, is something only humans can do.
  5. Creativity, or anything we deem perfect is only 10% substance. 90% of it is editing. Fine-tuning, tweaking, adjusting, correcting. It’s one thing to do something, it’s quite another to do it well. This is where the grace and “art” come in.
  6. When going to a restaurant, at least 20% of the time – don’t look at the menu, ask the waiter what they recommend, and just get that.
  7. Don’t have coffee for the first 90 minutes after waking up, it’s been proven to have reverse effects since you are dehydrated in the morning. Drink water instead. Along these lines, don’t drink coffee after 4pm. You need to sleep.
  8. Embrace Shoshin in everything you do. Have a beginner’s mindset and always be open to the possibility of new opportunities. Spend more time playing, and always be curious.
  9. Use ego as a driver. If I work in a public area, I check my phone less, because I want to appear productive. If I run where other people are running, my speed increases, because I don’t want to get passed. If I want to improve in a sport, play with others that are slightly better. Never be the smartest person in the room, and if you ever think you are, change rooms.
  10. Create incentives for yourself and your company wisely. When the British were governing India, they were concerned about cobras and offered a monetary reward for every snake brought to them. Soon after, local entrepreneurs started breeding cobras just to collect the bounties. After the government found out and ended the policy, all cobras used for breeding were released, which as a result, increased the total cobra population. Oftentimes the incentives we create for ourselves do not align with our own goals.
  11. Utilize Pareto’s Law – 80% of your results come from 20% of your activities. 80% of your problems come from 20% of your activities. Trim the fat, and focus on what matters most.
  12. Get paid in USD, spend in pesos, yen, rupees, euros, etc. US is the best place to make money, Europe is the best place to spend, Southeast Asia / Latin America is the best arbitrage (value per buck).
  13. Drink less. I know it’s hard for you to admit, but your parents were onto something here. Not saying you should give it up entirely, some of your favorite memories have been after a couple of beers where you and your current/new friends loosened up a bit, but sometimes a night in is better than going out. And the next day definitely is.
  14. When you are angry or stressed, go lift some heavy rocks in the gym.
  15. As far as I know, there is only one true answer to fully getting over heartbreak: time.
  16. It’s ok to reach out for help, no man is an island. And if you have ever seen further than others, know that it’s because you stood on the shoulders of giants.
  17. The ultimate form of leverage is when you are so indisputably good, that people call you when they need help.
  18. Remember the 5×5 rule – Most of us spend way too much time sweating the small stuff. If it won’t matter in 5 years, don’t spend more than 5 minutes worrying about it.
  19. Choose the third door into the nightclub of life. In life, there are always three ways in. There’s the first door, where 99% of people wait in line, hoping to get in. There’s the second door, where billionaires and royalty slip through. But then there is always, always… the third door. It’s the entrance where you have to jump out of line, run down the alley, climb over the dumpster, bang on the door a hundred times, crack open the window, and sneak through the kitchen. But there’s always a way in.
  20. Apply the principle of Misogi – Do something so difficult one day of the year (every year) that it has an impact on you for the other 364 days. Run a marathon, quit a job, start a business, etc.
  21. Follow the Rule of 100 – if you spend 100 hours in a year (equals 18 min a day) at working on one skill, you will be better than 95% of the world’s population.
  22. When I want to be more productive, go to phone settings –> Color Filters –> Greyscale mode on. Your brain will be 40% less ‘attracted’ to social media and other phone distractions.
  23. Pretend that you have a camera crew always following you around. Be the hero in your own story/movie. Your friends are the sidekicks, your music is the soundtrack, and your challenges are part of the character development. But you will come out on the other side, and it will be better than you can ever imagine.
  24. Your days are made up of good, bad, and “just ok.” 10% of the days you wake up amazing, ready to conquer the world, kiss the girl, and seize the day. These days you don’t need motivation, you are going to have a great time regardless. 10% of your days you wake up sick, heartbroken, injured, or upset – these days are the hardest to push through, and even when you do, they usually don’t move the needle forward that much. But the 80% days, the days that define your life, are the “just ok” ones. These are the mas o menos / comme ci, comme ça / so-so. They make up the majority of your life – so you need to push, squeeze the juice, memento mori, carpe diem, and do whatever it takes to win. It will make all the difference.
  25. Be a traveler. Go to the local restaurant whose name or menu you can’t pronounce. Jump in the local pickup basketball or futbol game. Walk the streets aimlessly until you inevitably get lost. Take the public transport. Have a drink with strangers. Learn how to say “thank you,” “sorry,” “hello,” and be able to order a cup of coffee in the local slang. Say yes to the randomness and craziness that life throws at you.
  26. Be a surfer. Paddle for waves, and when you catch one, enjoy it and be present. Yes, you know that wave is going to end, but it doesn’t matter nor make the ride any less beautiful. The more you surf, the more practice you put in, the more waves you catch. The collection of these raw, flashy, fleeting moments is the pinnacle of human experience.
  27. Be a snowboarder. Life is best when you are “living on the slope.” It’s here that we push past our comfort zone, try new things, and experience the most growth. Nobody ever became a pro skier or snowboarder by staying on the bunny slopes.
  28. Don’t worry. A bad day is coming for all of us, whether we like it or not. Someone we love will die, and we will die. So no need to cry over spilled coffee or flat tires. Enjoy the sunshine as you sit in traffic, be the last to release from a hug, and wake up every day cheesing from ear to ear. Life’s pretty great when you can bathe in the sun and dance in the rain.

Life Resume

A couple months ago, while I was updating my work resume, I suddenly asked myself: What am I actually proud of? I don’t give a shit about how I improved X% of a client’s operations, increased efficiency by Y, or saved Z amount of dollars for capitalistic companies that treat people as a number and data point.

So what do I care about? Enter the life resume: things that I deem important milestones for me about what I value and what has shaped me to be the “man” I am today.

LIFE EXPERIENCE 


PLYS,  Incorporated______________________ IL → OH → NJ → NY → Nomad

Son, Brother, Godfather, Friend, Lover, Athlete, Artist, US Citizen, Human

June, 1996 – Current


  • Scored 10 goals in a park district soccer game when I was 10 years old, received claps from over-competitive parents and was told that I’m a stud, thus beginning my egotistical nature and God complex 
  • Became an IHSA All-State Tennis player in Doubles due to quitting (being cut from) the varsity soccer team, missing school dances, having no social life, and realizing that Tennis players are, on average, less athletic than other sports teams
  • Won a $10K Business Scholarship after building a business plan and pitching my company called “Cake & Bake”
  • Failed building +30 side hustles, ranging from: lemonade stands to E-Commerce, selling “friendship” and the “possibility of giving my number” to affiliate marketing, coaching Tennis to selling books, trying to build physical products to coding social media apps, and everything in between
  • Built and sold Crazy Men’s Dress Socks, which, after all was said and done, probably broke even due to all my failed marketing campaigns
  • Read +50 books on self-help, productivity, and psychology to improve my crippling anxiety about not currently being Michael Jordan or Elon Musk
  • Created a Mental Models life guide that is +50 pages long and is structured on a use-case basis (when I am eating, when I want to sleep, when I want to get a job, when I want to develop a new skill, etc.)
  • Mastered how to play Riptide, Viva La Vida, Cigarette Daydreams, and other generic white boy music (except Wonderwall) in order to be campfire-ready, impress my drunk friends, and convince pretty girls that I’m actually a cool guy
  • Failed at becoming a “college dropout” and ended up getting the meaningless Magna Cum Laude accolade in Finance and Marketing
  • Cold emailed +5K prospective employers/mentors and scheduled +200 calls/coffee chats in order to land internships and full-time offers
  • Skipped my graduation and booked a bus from Ohio to meet up with some mentors in NYC
  • Made coloring books for executives (aka Management Consulting), where I became very good at going to meetings, preparing for meetings (I can make slides very fast), presenting at meetings, taking notes that could be included in meetings, and of course, scheduling future meetings
  • Cut my chin open and got stitches while riding my longboard around a neighborhood (you should have seen the pebble)
  • Traveled around North America (US, Canada, Mexico) with 3 friends for 2 years, where we visited +40 states, worked remotely from +50 Airbnbs, visited +20 National Parks, hiked, surfed, skied, and somehow didn’t kill each other in the process
  • Saved from drowning by my friend, Ben, while hiking through the Narrows in Zion National Park, Utah
  • Gained and lost +$100K in the stock market through my own personalized investing strategy, buying shares in individual companies I believe in, leveraged ETFs in particular high-growth sectors, and speculating on cryptocurrencies 
  • Quit my consulting job and solo traveled around Europe, Asia, and Africa for +1.5 years, visiting +45 countries 
  • Documented my travels and thoughts through blogs, photos, and films, yielding a culmination of +100K views across all platforms
  • Learned how to land a backside 360 on a snowboard after many attempts of falling on my ass, praying to a Snow God I don’t believe in, and putting +150 days in on the mountains (skiing US, Canada, France, Italy, and Switzerland)
  • Capitalized on my privilege and learned how to be a subpar surfer, traveling to some of the best spots in the world (California, Hawaii, North Carolina, Portugal, Indonesia, Morocco)
  • Given the opportunity to be involved in several love stories while traveling, some that I regret, some that I cherished, and other(s) that may still be ongoing (if only someone would confirm with the other party)
  • Played pick-up basketball in +10 countries around the world
  • Hiked +3 14ers (mountains over 14K feet) in Colorado, US
  • Biked across the Aran Islands off the coast of Ireland
  • Sumitted Pen y Fan (highest peak in South Wales), Bobotov (highest peak in Montenegro), and Mount Toubkal (highest peak in North Africa)
  • Bungee Jumped from Maslenica Bridge (tallest point to jump from in Croatia)
  • Paraglided (in tandem, lame I know) over Lake Ohrid, North Macedonia 
  • Experienced Oktoberfest (Wiesn) in Munich, Germany
  • Hot air ballooned in Cappadocia, Turkey
  • Island hopped around Hawaii, Greece, Indonesia, and Thailand
  • Trekked through the Sahara Desert on camel and foot with the Berbers (indigenous group of nomads) in Morocco
  • Marveled at some of the Wonders of the World (Grand Canyon, Colosseum, Eiffel Tower, Pyramids of Giza, Petra, etc.)
  • Bathed in the Dead Sea (lowest point on earth)
  • Designed a travel app (WIP) to revolutionize the way backpackers/nomads interact and stay in touch with their travel friends 
  • Informed that I could be a professional dancer by +200 drunk people in my life
  • Repeated the exact same 3 magic tricks at parties that I learned when I was 13 years old
  • Notified that only 1 of 8 of my jokes land and are actually funny, but that has never stopped me from trying (quantity over quality approach)

FUTURE LIFE


Goals: Visit +100 countries in the world, retire from the working world, drop an album, get sky/scuba dive certified, be a better surfer/snowboarder, be a better friend, be a better human


After writing this out, it’s been great to look back at this to 1) Reflect and show gratitude for the life I’ve been blessed with 2) Use it as an operating model for living. If I ever come across a challenge or opportunity that would make a bullet point on this list, then I have to do it.

“Life is our resume. It is our story to tell, and the choices we make write the chapters. Can we live in a way where we look forward to looking back?”

– Matthew McConaughey

27 Things I Learned Turning 27

Writing this in a cafe in Tel Aviv, Israel, I can’t help but think about my friend Beane while typing this. That guy is obsessed with this number. Well, it feels like just the other day I was the 17-year-old, skinny, acne-prone, cocky, full-of-himself boy who thought he was going to take on the world. Come to think of it…all of that still holds true.

Reflecting on my short time here in this massive playground we call “life,” here’s 27 things I have realized and am trying to understand/implement in my day to day:

(Note: Like most things in life, few of these ideas are original. Inspirations and mentors include, but are not limited to: Tim Ferriss, Naval Ravikant, Jim Rohn, Napoleon Hill, Stephen Covey, Gary Vee, Alex Hormozi, Bill Perkins, Zig Ziglar, and others)

  1. No one owes you anything. And no one cares about what you are feeling or how “hard you’ve had it.” People only care about what you can do for them. How you’ve made them feel.
  2. Privilege breeds more privilege. I’ve lived an easy life according to most definitions. And because I’ve been “born ahead” of other people, the race to certain life milestones has been more accessible, which gives me the ability to get to the next one quicker, and so on. If you are the best football player on your team at a young age, you will play more minutes than your peers, giving you more touches on the ball, more game time experiences, and more opportunities to grow. This only widens the gap. Making it harder and harder for those with less to catch up. It’s incredibly important for me to recognize that I was born with pocket Aces, show gratitude for the life I’ve been handed, and try to pay it forward / even the scales for others I cross paths with.
  3. Life is like Netflix. Avoid the endless scrolling, pick a goddamn movie, and see it through.
  4. Focus on ROE – not return on equity, but return on experience. Memories are all we get to keep at the end of the day. So invest in things that will give you the most memory dividends. For one-time purchases, you can have a memory dividend that pays out every time you relive or retell your stories. With this in mind, it pays more to have experiences earlier in life. Instead of constantly worrying about your Work Resume, think about your Life Resume. What would you put on it?
  5. Add a little bit of spice. Brush your teeth / eat with your non-dominant hand, angle your hats differently, lift up one sock, grow out your hair. Have fun.
  6. Personalize everything. Create your own brand. Create a unique system of writing, thinking, and talking that is specific to you and works for you. Pick a favorite number, favorite color, favorite sports team, etc, and own it.
  7. Don’t ask what the world needs, ask what sets your soul on fire. And go do that.
  8. Don’t wait for people. Do epic shit. Your people will find you.
  9. Taste everything once. You never know what you may like until you try it yourself.
  10. Introduce yourself to everyone. First and last name.
  11. All you touch and all you see is all your life will ever be. Pet the dog/cat, smell the flower, ask the girl out, try the new food, watch the sunset, book the ticket, take the flight, ride the wave, jump off a snowboard, sing in karaoke, dance in the street.
  12. Exercise the mind. Come up with 10 new ideas a day. Become an idea machine by taking the quantity over quality approach.
  13. Tell stories. People don’t remember statistics or facts, but they buy into humans. To be human is to have your own story, your own thoughts, emotions, perspective, memories, and experiences. Share it with others.
  14. Take opposing viewpoints on the world and play them against each other, adopting whatever serves your purpose at the time. Examples:
    • When I want to work harder / do more, I tell myself: This is my one life, as far as I know it. I already won the lotto, being born a human, which is 400 Trillion to 1 odds. I have around 85 years of life, so I’m in my second quarter already. The first quarter of life was just learning the rules of this video game we call life, now I need to dominate life and defeat bosses. I need to squeeze the juice and do everything possible to live my best life. To avoid being on my deathbed and have “what if” floating around.
    • When I feel overwhelmed/stressed, I tell myself: This doesn’t matter. Nothing really matters. In a hundred years, I and everyone I know will be dead, and no one will remember anything. I could go on to create the world’s most valuable company, and then be 6 feet under the ground in 50 years. I could also play video games for the rest of my life, and it still doesn’t matter. Legacy doesn’t fucking matter when you’re dead. So no point in my stress. I have lived many a conflict in my life, and most of them never came to pass, but just lived in my head. So screw it, take the day off, and stop applying needless pressure.
  15. You catch more flies with honey. Often, the best way to win an argument is to avoid one altogether.
  16. Wealth comes from VALUE x LEVERAGE x SCALE. VALUE = Time / Money / Improvement in people’s lives. LEVERAGE = Capital x People x Systems. SCALE is derived from the number of people served. In today’s world, the quickest way to grow is with permissionless leverage. (Media or Code)
  17. In a world where everything is finite, play infinite games. My friends, business partners, hobbies, and passions should be lifetime pursuits. Perfection and winning the game is not the goal. The goal is to keep playing the game, and to get one day better, every day.
  18. You get more out of reading 1 book that’s great 5 times, than out of reading 5 mediocre books.
  19. Extraordinary accomplishments come from doing ordinary things for extraordinary periods of time.
  20. Focus time and energy on Multipliers. Multipliers are activities that compound and yield dividends. Once-in-a-lifetime experiences, goodwill to others, financial investments, and personal development are examples. Activities that are directly related to your time, and cannot be shortened in the future, should be avoided, unless you get real enjoyment from them. For this reason, since I don’t like cooking, I should avoid it and prioritize other activities.
  21. You gain status by giving more to the group than you get. Note: status is a tool that can help you accomplish your goals, but it should not be the top priority.
  22. Make sure the girl sitting next to you in the passenger seat is the same girl who would be waiting with you at a bus stop if life turned out differently.
  23. The current economic system is broken. We were not meant to just study things that don’t fascinate us, work a shitty job, retire in old age, and then die. Life is a marathon, but I like to live my life in short sprints. Ideally, I break life into 3 phases: Exploration, Deep Work, and Vacation. When I wake up, I would like to have options of different projects that I find 1) Meaningful 2) Play to my skill sets 3) Make me money 4) Give me the opportunity to grow. I then can pick what I find to be the best fit at the time, and work hard on it. After that, maybe I go dance my ass off in Ibiza, surf in Bali, or visit friends in the US. Once my system is cleared, I start thinking about the next thing, read more books, take more courses, and learn/hone more skills. The cycle repeats, burnout never happens, I still save for “raining days” or old age, but I don’t miss out on the present moment of my current age. Because, at the end of the day, the present is all we have.
  24. You don’t become confident by shouting affirmations in the mirror, you become it by having a stack of undeniable proof that you are who you say you are. Outwork your own self-doubt.
  25. Ready, Fire, Aim. when you see an opportunity, take the shot. If you miss, then you readjust and take another shot. If you end up waiting, aiming for the perfect shot, the opportunity is often already gone
  26. Understand that the 3 biggest decisions in life are 1) what you do 2) who you are with 3) where you live. Practically everything else is cheese.
  27. Time is the most valuable currency in the world. A Billionaire on his deathbed would give all of his net worth for one more year. Imagine how much he would trade to be in your shoes right now. You are worth more than a Billionaire, so act as such, and be resilient with what you trade your time with.
    • Taking into account a life expectancy of 85, and just turning 27, I have approximately 1.8 Billion seconds left. Time Billionaire > Monetary Billionaire, so wake up every day smiling.

20s are a wash

I want to treat the rest of my 20s like they are a wash.

Now is not the time to get a safe job. I already did that.

Now is the time to be as risk focused as possible.

I will never be as “free” as I am now.

I have no baggage. No college debt left, no significant other, no parents I need to take care of, no children, nothing.

I can eat like shit and still be ok.

I can barely sleep and be fine.

Not saying I shouldn’t eat and sleep well, but I could survive. And on top of that, it’s not that hard to still eat and sleep well.

I can sleep anywhere (couches, beds without a bed frame, floor) and cook cheaply.

I can live for free with friends or my family.

I can stay in hostels for cheap all around the world.

I’m 26 now, so I have 4 years left.

So let’s think about the worst-case scenario: I wake up broke at 30. I have to move back home with the parents. I have to get the “safe job.”

Most likely scenario: I wake up broke at 30. But I’ve traveled the world, met incredible people, tried starting businesses, tried learning a new language, tried getting jacked in the gym, and learned about all these things I do/do not like. And then I can still use my college education and friends to get the “safe job.”

I understand this “20s are a wash” is a privilege. I am a college grad, I grew up / still have a somewhat stable family household, I have good friends/mentors, my body is fully functional, and I was born with a good mental state. But one thing I have learned in the last couple of years is it’s foolish to not recognize the privilege, but even more foolish to not use it. It would be selfish of me to not go for it. To not try and live my best possible life. If I was to just coast on my privilege, then I would be just taking it for granted. I owe it to my family and friends to go for it.

And the best-case scenario? I think we can all realize how good life can get.

But I think the best will be to look back on my life and not wonder: “what if…”

To know that I went for it.

And the chips fell where they did. But I went all in.

Hell, I was born with pocket Aces.

What a foolish thing to go silently, tiptoeing, safely to my deathbed.

I want scars.

I want the lessons, the failures, the struggles.

I want to point to the scar tissue on my body and say: Got this playing basketball with friends, this from snowboarding, this from longboarding, this from surfing…

When I was studying at Uni, I heard a quote from Peter Thiel that has stuck with me since. He said, “In a world that’s changing so quickly, the biggest risk you can take is not taking any risk.”

What a sad day it would be if I woke up and realized there was no time to try out / risk / do the things I always wanted. (Paulo Coehlo paraphrase)

The happiest I’ve been in my life has always been when I’m doing what I deem “epic shit.”

That’s often when adrenaline and risk are involved.

I could get hurt doing this. I could lose money, get my heart broken, fall off a cliff, get shattered by a wave.

But it’s all risky.

None of us are making it out of this alive.

Nietzsche said: “I know of no better life purpose than to perish in attempting the great and the impossible.”

That makes sense. Why be satisfied with average?

But the key is to listen to my own internal dialogue about what I deem ”great and impossible.”

My definition of “epic shit.”

I don’t need to surf Nazare waves.

But maybe I don’t go back to working in Corporate America for now.

Maybe I don’t play the status games of a high-paying job and instead take the zero pay of startup life.

Follow the “epic shit” and happiness model, cut out the status games and flexing that is engrained in me.

When in doubt about what to do, I should do what scares me.

Because if my dreams and plans don’t scare me, I’m not dreaming big enough.