I’ve been to Japan before, but never like this.
Back in October 2023, I had the once-in-a-lifetime chance to explore Kyoto and Tokyo with Entrepreneur’s Organization: Los Angeles for one week led by an EO member named Takeshi who is from Japan and wanted to show us his version of the country.
The trip was perfectly planned, with hotels, activities, dinners at amazing restaurants, transportation and almost everything figured out for us. It spoiled me so much that I honestly never want to have to plan a vacation again. (Some people love creation vacation itineraries, I prefer delegating all of that when possible)
If you want to see some previous travel posts, check out my recent trips to: Poland, Mexico, and Dubai (which is my favorite city in the world and now my permanent home). There will be a big post on why I moved from Arizona to Dubai coming up soon.
The cool thing about this trip was that it was with me, my plus one (winky face) and a 30-person group of EO LA members and their plus ones. Sometimes, on long trips, I crave new interactions and fresh conversations. With this setup, I had a massive variety of people, cultures and relationships to build and everyone had unique entrepreneurial backgrounds.
The trip started in the serene beauty of Kyoto for a few days and ended in wild and lively Tokyo. Here were some highlights:
Swinging A Samurai Sword
In Kyoto, one of my favorite activities was learning to use a samurai sword. A group of us entered a samurai’s real home, which was designed to evade attackers and defend itself with hidden passageways and secret exits.
It began with an experienced samurai expertly chopping bundles of bamboo (to simulate severing a human limb) with dramatic drumming in the background.
We got a demonstration with a huge drum roll before a real samurai came in and chopped some bamboo rods.
Dressed in kimonos, we headed outside and practiced swinging a fake sword to learn the movements. The instructor guided us to breath, move fluidly and focus on the sword and our movements.
Then we got to hold REAL swords. I managed to chop the bamboo in one-go and the instructor said I had “great focus.” It was thrilling!
It ended with a meditation session…and many cool photos.
The Life of a Sumo Wrestler
In Tokyo, we went to a sumo wrestling training facility. It has a large circular covered in sand and huge men, wearing very little clothing practicing the sumo technique of crashing into each other with the goal to grapple your opponent and force him outside the circle. Their trainers gave them tips as we watched for about an hour.
Sumo wrestlers typically wake up at 6:30AM and train while fasted. They practice for hours and you can see the bruises and cuts on their legs and arms from all of the dragging and grappling all day long on sand. After 4 hours of training, they bath and eat a huge lunch, take a long nap, wake up and lift weights. Then it’s dinner, relaxing and they’re in bed by 9:30pm. The cycle repeats itself for months.
They get a chance to compete and the rounds are often very fast, often 60 seconds to a few minutes in length. If you lose, you are disqualified and there are no rematches. Few make it to the elite level and earn a good salary.
It was fascinating to watch their focus, dedication, and endless hours of ramming into each other. It does a lot of damage to the body, but that’s the sacrifice they make to perfect their craft.
After their training, we got to take pictures with the wrestlers (which helps pay for their training)
The Food of Japan
The Japanese diet is one of the most flavorful, lightest and healthiest cuisines in the world. It’s filled with vegetables in many forms, that could be steamed, sauted or pickled. Meals are accompanied by rice, soup and mostly seafood. I think I ate sashimi almost everyday, but never got bored of it because it was often presented in unique ways.
Their breakfast is a work of art: filled with vegetables, salmon, egg, rice porridge and fruit. It’s delicious and energizing, without feeling heavy.
Other Food Highlights:
In Kyoto, we had an epic multi-course meal with EO Kyoto members. Each dish looked like a work of art. I even ate turtle, which was kind of gummy and fatty, but tasty. We chatted about life, business, family, friends, taxes (one of my favorite subjects ;), food and everything else.
In Tokyo, we met with members of EO Tokyo at a very cool and unique restaurant. You sit at a counter and in front of you are tons of vegetables, fish, potatoes and meats that are raw. You point to something, and the chef uses a paddle that’s about 3 feet long to pick up the item, cook it in front of you, then immaculately plate it before serving it to you piping hot and
fresh. It was so much fun (and a bit expensive…because we didn’t know the price of everything and indulged a lot in urchin, steaks, fish and so much more!). Worth it
Geisha Games
One night, the EO chapters of Kyoto, Osaka and Los Angeles teamed up to throw a big party, which included real Geishas.
Geishas are female entertainers, musicians and dancers all rolled into one. They are young women with lots of white makeup and traditional clothing meant to provide liveliness to any event.
First they sang and gracefully danced.
Then they played games with the crowd.
One game involved a 1-on-1 competition. The Geisha and participants would clap their hands, then touch a brick, then clap their hands. At any point, either person could grab the brick and the other person had to respond to this with a specific gesture. If they didn’t do the gesture, they lost. The brick could be moved back to the main playing area at any point. It’s a fast moving game of dexterity and focus.
When it came to my turn, my competitive instincts kicked in and it got intense. The round lasted a long time, and sometimes I grabbed the brick and other times the Geisha grabbed it. After what seemed like endless minutes..the Geisha messed up and I won! I was the first of the group to beat the Geisha!
I was so happy and it was a blast.
My EO Brethren
After all my travels, I’ve learned a key tip: “It’s not what you do, but who you do it with.”
That “who” could be fantastic new people you meet on your journey to a new destination.
Or it could be the people you went on your vacation with.
Or it could be BOTH.
On this trip, as a member of EO Los Angeles, I made many new friends and shared memories with people I already knew.
We all have a lot in common because the group is designed for entrepreneurs and there is a shared passion for adventure, connection and learning.
One time, while walking through Tokyo I was chatting with Ken about life, business and EO stuff while our dates were behind us. We had just seen the Tokyo Sky tower, a massive 2,000+ foot structure that dominates the city skyline. At the top, it has incredible views for miles.
At a stop light, the girls asked us, “Are you guys STILL talking about business?”
With a grin, I said, “Yes!”
We laughed and went back to our never-ending chat about life as an entrepreneur…while on vacation…in Tokyo on a sunny weekday afternoon… while our teams were busy working at keeping our clients happy.
It’s moments like that, where you step back and think “Life is good”
Learning From Those Ahead of You
Sitting at dinner, with a 5-course meal ahead of us on the last night of the trip, I struck up a conversation with a more seasoned entrepreneur who had sold his business for…8 figures.
Immediately, my interest peaked and I had to learn how he did it.
We went into a deep dive conversation about the-ins-and-outs of getting a business ready to sell and how to position it for success.
To increase the value of how much you can sell your company for, you have to have several key factors like:
- The Switzerland effect: Your business can run without, you the owner, stuck in the day-to-day activities
- No “Whale” Clients: No one client is over 20% of your annual revenue, so you’re not afraid if one ends up leaving your company in the future
- 3 Year Growth: Each year your company shows year-after-year uphill growth.
- Strong Gross Margins: your direct labor and direct supply costs for your product or service are very reasonable/low.
- High Net Profit / EBITA: You have a very nice and very sizable net profit after all expenses are paid like internal team costs, software, legal fees, supplies, office, marketing and more.
- Fully Built Leadership Team: You have a team of leaders that grow the company and keep clients happy and coming back for more without the owner involved.
Hearing this guy’s story was so cool and inspiring. We must have talked for at least an hour on just the business, while dining on perfectly plated wagyu beef.
Karaoke Craziness
After that meal, we had to cap the trip off with karaoke.
In America, karaoke is typically in a crowded bar with a ton of strangers, but I like how in Japan you get to rent a private room (with your own bartender) reserved exclusively for all of our friends.
On that night, we pounded cocktails and sang our hearts out.
(I’m not gonna lie, I can be a bit of a showman at times.)
My go-to song, even though I’m not a good singer but a pretty good performer is Bruno Mars; “Uptown Funk”
I like to dance, and the song is much more about energy than it is about vocal performance.
Plus, everyone likes it!
And then there’s the real show stopper: “I Want It That Way” by The Backstreet Boys
Everyone knows the words, and everyone loves that song.
The energy, comradery, learning and sheer amount of FUN could not have ended on a higher note.
And then the next day I got a Japanese chef knife with my initials so I could do more “chopping” at home.
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While that trip ended, another EO Los Angeles event awaits me in April: a trip to Nepal. And then Armenia in October…and many more ahead with this wonderful group.
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