[英語] The Risk of Playing it Safe

At work, I was so stressed out I wore a red rubber band on my arm to snap myself whenever I had a depressing thought. It really worked. But one day, I realized how sad it was to wear the rubber band in the first place. It was a shackle.

The thing is, I actually liked my job for the most part. In the one year I worked as an associate at one of Japan’s top venture capital company, I got to fly around the world to meet potential investees, helped run a startup accelerator, met amazing entrepreneurs from around the world, single-handedly ran the first FailCon in Japan, and even helped publish the Japanese version of Disciplined Entrepreneurship. Every month was different, never being too repetitive.

But I wasn’t happy.

I worked 9:30am to 21:30pm every day. Eat, sleep, work, repeat. There was no time for personal growth, leisure, or friends. The worst was working hard all day, only to wake up and realize it was all a dream. It was bad enough that all I did was work, but now I don’t even get to enjoy my own dreams? Was this how I want to live my life? Was this what the path to success looks like? It didn’t feel like it.

I wanted to travel. I wanted to gain new skills. I wanted to create products rather than just fund them. I wanted to not have a clue where my life would be in 6 months.

So, after one year of joining the workforce, I quit. I put in my two month’s notice. I didn’t have a concrete plan of how I was going to make a living. No brilliant transition to something immediately grand. I just knew that if I stayed, I would be tired and depressed, like the rest of the salarymen I see on the subway, and the thought of it suffocated me.

(via http://gendai.ismedia.jp/)

Many people want to quit their jobs and pursue their passions. I understand it’s not an easy choice to make, but it was honestly one of the best life decisions I’ve made. I felt in control. My path was my own to narrate. I’ve got my fair share of problems, but I’m happier and am growing as a person, faster than ever.  All that rubber band shackles now is a deck of cards.

This is NOT an article on how to quit your job. Rather, it’s a fascinating look at the universal pattern of how people grow, and why forging our own path in life should be our first priority.

Enter The Hero’s Journey

I’m intrigued by Joseph Campbell, who uncovered the concept of the Hero’s Journey, a narrative pattern found in almost every major work of literature:


The Hero begins in the familiar world, but must depart to navigate the unfamiliar world. In the unfamiliar, the Hero is faced with numerous trials of fear and death. Out of struggle comes a new strength. The Hero takes possession of this new strength to defeat his ultimate tribulation. Our protagonist completes the journey by returning to the familiar world with the new-found power to transform society, just as the Hero, himself, has been transformed.

I believe that, at any given time, we are all protagonists in a narrative, going through the Hero’s Journey, over and over again. But when I look around, it’s easy to see who has countlessly ventured into the unfamiliar world, and who has always remained in the familiar. I see the latter as a tragedy. Especially amongst young adults.

Young adulthood is the first time you become the main author of your life; the sole architect of your narrative.

It’s the liberty we’ve won for ourselves after years of preparation, and we should be taking advantage of that. While we’re young, we should spend as much time in the unfamiliar world as possible. We need to continuously cycle through the Hero’s Journey to grow ourselves in ways we never thought we could. To find out who we could become. To see where we could end up:

A ship in harbor is safe, but that is not what ships are built for.”
– John Augustus Shedd

You don’t need to rush to a salaried life and have someone direct it for you again. Because, unless that’s your dream job, the cost will be your youth:

“You can always sit down and work. You only have a period of time where you’re at your peak physical. Use that shit up.”
– Michael Dorian Bach

Once you grow older, you become in charge of other peoples’ narratives; it won’t be just about you anymore. And that’s ok. But your journeys will have to become less frequent. And you begin to worry of losing against the trials and taking your loved ones down with you. So, a fantasy broods amongst these late heroes, thinking that their personal journey can start after 65. But by then, they’ve become too fatigued to go conquer the big quests.

Here’s what people in the last years of their lives had to say:

via Barking Up The Wrong Tree

Bronnie Ware worked in palliative care for many years, tending to people during the last three to twelve weeks of their lives. A handful of themes cropped up in the things they regretted during their final days:

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
2. I wish I didn’t work so hard.
3. I wish I’d had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish that I had let myself be happier.

Looking at this list makes it clear how vital having the courage to challenge your self is, when you have the health to do it. Some people are afraid of quitting because of financial security or what they’ll look like if they fail, but the only thing you should be afraid of is regret.

Health is temporary. TEMPORARY

It truly is the only time you can rapidly undergo self-transcendence. So pursue those crazy ideas. Create things. Travel to new countries. Get lost. Fall hopelessly in love. Experience the ecstasy of the present. Find your goosebumps. Lose a finger or two.

Then return from it, stronger than ever. Share your tales to help others.
And when you’re ready, start the journey again.

[英語] ¥0 to ¥500,000/mo Revenue in 6 months with Airbnb


Airbnb is the reason why I can be on a rooftop cafe in Bangkok and write this article, while I still generate income in another country. I was able to go from nothing to ¥560,000/month ($4635) in recurring revenue in 6 months. The picture above is what my booking schedule looked like in January.

How to start/improve an Airbnb listing is what I get asked about the most, by friends and strangers, alike. It was getting ridiculous, and there was way too much advice to cover. For posterity’s sake, I thought I’d write some of the things I learned along the way.


Airbnb hosting is one of my favorite jobs. Not only is it highly profitable and flexible, the whole operation can be run on a smartphone app. You also get to chat with fascinating wanderlusters from all around the world! I’ve spent entire days with some of them, exchanging crazy cultural stories and enjoying each other’s perspectives on life. The benefits of hosting can change your life.


Above are my two places I rent out in Tokyo. One is a designer house in the west suburbs, and the other is a single room apartment near the downtown area.

The apartment I rent out entirely. The house, I live in along with two housemates, and we rent private bedrooms on the 2nd and 3rd floor. Together, they produce a total of ¥560,000 in recurring monthly revenue. It takes around 2 hours a week to run; 7 hours if I do all of the cleaning myself.

The biggest costs are, in order: rent, utilities, cleaning, wifi, household supplies.That leaves me with roughly 46% of the revenue (¥257,600) as gross profit, which puts the income generated per work hour at ¥9,200. Not bad for something you’re running from home.

Enough about my place. Let’s talk turkey.

The Unfair Advantage

What makes your place THE place to stay?

One of my listings is a house. It’s farther out than most of the listings in Tokyo. It’s not shown in that general area range shown when you type “Tokyo” in the Airbnb search bar. It’s not an ‘entire place’ listing, we only offer private rooms, since I live on the first floor. It’s not even cheap. Despite this, my house gets 24~28 days booked on all months for ¥12000~¥22000. Why?

That would be thanks to my unfair advantages. The unfair advantage is the special value of your product/business that can not easily be copied. My listing is a spacious designer house that can host 7 people at once, in a city where the competitors’ listings are mostly small apartments that can only host 2 people. Therefore, the unfair advantages are “spacious,” “designer,” “house,” and “rentable to groups of 2-7.”

Unfair advantages can make Airbnb users go out of their way in their vacation just to stay at your listing. Some examples would be supreme location, short distance to a train station, space to host over 3 guests in a crowded citymassive amounts of reviews, or having unique architecture like a castle,  ethnic home, bus, or even a treehouse.


Before I came to Bangkok, I looked at Airbnb to see what great offers there were in Thailand. I zoomed out of the map a bit, only to have that treehouse pop up.

That place isn’t even in Thailand. It stands on the sands of Taal Lake, a volcanic caldera on the island of Luzon, Philippines. I immediately reserved it on impulse. There’s a million apartments on Airbnb but only one volcano lake tree house. The unfair advantage of this tree house was so powerful, it made me book a flight to a country that I wasn’t even planning on going to.

What can you offer that will become your unfair advantage? If a bus, treehouse, and castle fit in the same ‘advantage’ category, it’s obvious that you don’t have to be rich. Just creative. 

The Competitive Advantage

You also need to simply offer things that are comparatively better than your surrounding competitors, even if they are copiable. That’s your competitive advantage. Things like, making your place look clean and beautiful, wifi (especially pocket wifi), or even bicycles. It’s the combination of unfair and competitive advantages that make an excellent Airbnb listing.

Screen Shot 2015-03-10 at 11.32.28 AM

“Why bother with offering something that others can copy?” Because most hosts are lazy. With effort on your part, you can beat out most of your competition, even without a strong unfair advantage.

The most frequently used competitive advantage is the interior design. The most successful listings are always beautiful, proving that most people go to Airbnb to find lovely homes, not simply houses. I’m not going to get into interior design principles here. I will suggest, however, that you can use interior design to create a semi-unfair advantage. Good examples are adding a hammock


or even making the entire place Hello Kitty themed. Not kidding.

Screen Shot 2015-03-10 at 11.34.39 AM


The Photos

Photography is the reason Airbnb went from a failing startup to a successful one. It is the key medium used to convey your unfair and competitive advantages. I mean, just look at the Airbnb user interface.


Notice that the screen space is used up by 40% map, 40% listings, and 20% every thing else?  Now look at one of those listing spaces.


Roughly 80% of the space is used to convey the photos. That’s a huge monopoly of space use, considering there are 10 species of information there (image, price, title, host image, type of room, review number, location, instant booking availability, favorite status). It conveys how immensely important images are when users are choosing a listing, and Airbnb knows it.

Once you’ve made your place look clean and well furnished, go reserve Airbnb’s free professional photography service (yes, free!). After that, take your own HD photos of the neighborhood. Find the most unique locations in the area, so you can show it off as a strong advantage.

“How do I know my location is good?”

Use AirDnA to determine if you live in the areas with a lot of listings. Those areas correlate to the areas highest in demand.

In Tokyo’s case, the popular areas are Shibuya, Shinjuku, then Asakusa. As they should be, since every Tokyo travel website features these areas.

Not in a super popular area? No problem. You can still test how much money you can make by going to similar listings in your area and checking their calendar. Click the “Check In tab” to make the listing calendar pop up.


Let’s see how this listing is doing…


These guys have 21 days booked this month. Their price is ¥13050, so that’s ¥274050/month in revenue. Even over-estimating their total cost at ¥150000 a month, they are still in the green. That’s at least one listing making money in your area. Keep looking at more.

(Side note: Be careful of checking demand this way. Some hosts only rent their places out on certain times, and block out rentable dates for months at a time. It’s easy to mistake that on that on the calendar as fully booked months.)

“What should I set the price to?”

A $30 customer is completely different from a $90 customer.

That $30 customer will take longer to book, ask for discounts, have more requests,  and leave your room dirtier than a $90 customer. It seems counter intuitive, but it’s generally true.

You want to have the customers that are less price conscious. They tend to be more mature, well-mannered, and more loyal. And best of all for you, the profit margin will be higher.

What you need to do is to search for similar listings to yours in your area like you did earlier, and look at the ones with the most review numbers. Price it around there from the start. Once you’ve gotten a few reviews, bump up the price more than you’re comfortable with. Nope, even more.

marchairbnbAirbnb lets you change the price of any specific date. If there are upcoming dates in the next 0~15 days that aren’t booked, reduce the price back to the area average just for those days.

The Reviews

Reviews are genuine karma points.
Lots of 5 five stars will gain you trust and you’ll be prioritized by the Airbnb search engine. Anything below a 4 will wreck you.

Its nothing hard: just genuinely be a good host, clean well, respond to any of their questions kindly, and don’t lie to them about what your place is like. If you’re lazy or fake anything, you’ll get bad reviews.

And seriously, don’t do that to the guests.

In my experience, most of these people that use Airbnb are really nice folks. They’re on this site because they want to experience foreign cultures in a new way. They know using Airbnb is infinitely more risky than getting a hotel room. And for many, it’s their first time using it. Don’t make it a bad experience for them.

The Title

The best listings I see use the title as a space to convey the unfair and competitive advantages you couldn’t in the photos.

Frequent keywords are: location, minutes from the train station, “free portable wi-fi”, or a variety of comforting adjectives. Mine include: “near Shibuya”, “12 min” “Shinjuku” “wi-fi” “designer.” If you’re not sure what to put, look at a few of the top-listings with the highest reviews in your area as inspiration.

The Profile Image

People will judge your listing by your looks. That’s human nature; gotta deal with it.

My advice is to treat it like an online dating profile: Use a photo with friends in it or a selfie with the opposite sex. I use a picture with my girlfriend in it to convey trust and safety. Just please don’t take a picture with you standing alone under the fluorescent light in the VERY ROOM YOU’RE RENTING.

Don’t skimp out on the profile description, either. Make yourself approachable to guests. It’s not going to make or break your listing, but it definitely helps.

The Conclusion

Airbnb is just like starting any other business. Do your market research, consider what’s unique about your place and push it, offer more perks than competitors, give guests an excellent experience, present your place and yourself well, and be confident about your high prices.

I know it’s a handful.

Remember that this article only helps to maximize profit for your listing. Understand that you’ll get a fair amount of guests even if you don’t have the perfect listing. My apartment listing first had amateur pictures I took myself, and I still got 5 bookings that month.

As Reid Hoffman, co-founder of LinkedIn, said,

Just launch and see what happens. Then, improve it.