What I Learned from 365 Days living on Airbnb

An entrepreneurial-bootcamp odyssey… in pictures

Chenyu Zheng
11 min readMay 15, 2017
Doug’s Treehouse in Burlingame, CA

From Sept 2015 to Sept 2016, I embarked on a year-long experimental living without a lease, and lived in 99 (shared) homes via Airbnb. The majority of my urban nomad life was in Los Angeles — a mega city that I used to feel distant to. My goal was to travel “within” a city to uncover unique homes and hospitality, and to inspire a new way of travel in China (where I have a decent following).

Looking back, this journey also trained me as an entrepreneur in 4 ways.

First, let me explain why I dedicated 365 days on this experiment:

Growing up and studying internationally in China, rural Connecticut, Princeton, Oxford, Spain, Nicaragua, Ghana, India, I become intensely curious about new cultures. Living with locals has been my way of traveling since teenager days — when I had my first “host family” in Connecticut during high school.

They planted the seeds of hospitality in me and taught me what it means to welcome strangers home with a warm heart.

my American grandparents since 2006

Airbnb speaks to my travel philosophy and I became a super user in 2012.

I asked myself 3 questions before I started the journey:

  • What does “Home” mean?
  • What is it like to live the life of a _____ ?(fill in the blank with “pilot” “architect” “filmmaker” “vintage store owner” “Airbnb co-founder” etc)
  • What does the future hospitality school look like? (it might not be Cornell Hotel School but Airbnb hosts’ homes)

I did not quit my job, but rather Airbnb has been part of daily life. I stay at any Airbnb home from 1 day to 4 weeks, and even become a pet watcher for some hosts.

This is a journey of sharing a piece of life of a pilot, an architect, a meditation master or a vintage car collector.

What does the journey look like?

Los Angeles was my home base for 7 months.

From Monday to Thursday, I would stay at Airbnb homes within 15 minutes’ commute to my office in Venice Beach (via bikes or Uber Pool). Being a New Yorker before moving to LA, I did not have a car.

On weekends, I travel to neighborhoods as far as Pasadena, Downtown LA, and Lincoln Heights. For 7 months, I explored 15 neighborhoods in LA. You can only be a “local” if you lived there instead of driving through.

LA is a city of imagination: trailers in the backyard, Alice in Wonderland just off Abbot Kinney, tree house, art gallery, 1925 Spanish revival castle you name it.

LA homes: Alice in Wonderland | 1925 Spanish Revival | Architect’s Home | Art Gallery Home

LA is also a city hard to belong to for an outsider — its urban crawl, its Hollywood fame and glamour. At the same time, LA has so many creative and quirky artists. I wanted to know those who made that steel tall house in Venice, or that solar powered Moroccan house in Culver City. Airbnb democratized the social layer : I not only enjoyed the murals, but stayed with the artists who created local culture.

How do I pick hosts?

created a hashtag: #SuperhostSelife
  • 90% with “Superhost” badge
  • In search of interesting and well-travelled hosts:
    In China, there is a saying “Buddha says people with similar hearts will meet.” This is a journey in search of friends that I am supposed to meet in life and share a piece of their lives.
  • Curate wish lists of unique homes in each city
    Home decor is an extension of our soul and values. By looking at photos and description, I can tell a lot about the host.
  • Google Search keywords, such as “Architect Airbnb LA” to find out all the airbnbs with architectural meanings.

The Struggles

The struggle is real: I jot them down in a car ride.

Live with Less and in 3 colors

at most 2 suitcases at any given week

Belongings: Before moving back to LA, I spent 14 months in Shenzhen launching a startup. Thus, all my belongings were in storage. I came back to LA with 2 suitcases. Packing up an apartment might be the biggest mental blocker for this journey.

Living out of 1–2 suitcases also made me efficient in packing and un-packing.

“like perfect tetris”

I learned to live with minimalist style: 3 pairs of shoes, none-wrinkle, fast dry clothes of navy blue, black and white . Simple clothes allowed me to allocate time and brain space from coordinating outfits to commuting between Airbnbs after work.

My Friday night routine was taking a UberPool from office at 8pm (to avoid traffic) from Venice Beach to a far away neighborhood in LA. Or catch a flight out from LAX (20min ride from my office) to spend 48 hours in Portland, Seattle or San Francisco and flew in early Monday morning to arrive at office for work.

I lost appetite in shopping for material goods but focused on getting to know my hosts: artists, architects, vintage car collector.

Entrepreneur-in-training: 4 take-aways

  1. Be a “cereal” entrepreneur

- Be bold and apply original thinking
- Imagine the ideal outcome
- Be resourceful to make the outcome a reality

This is an Airbnb core value — the founders made cereal boxes of Obama’Os to raise $$ during the 2008 Election.

left: ObamaO in Airbnb HQ; right: Joe with a plate I made

365 Days On Airbnb is a journey of being bold and resourceful. When life throws me a lemon, I make it into lemonade.

1–1 Make it affordable

“How do you afford it?” is often the first question I receive.

This project is independent and self-financed. I set a daily budget of ~$80.

Besides savings, I found a few creative outlets:
(1) Airbnb Referral credits: up to $5000 (from every Chinese traveler who signed up via my guide and took first trip)

Referral credits afforded me 3 months of living on Airbnb

In July 2015, I wrote a guide on how to use Airbnb (first of its kind in Mandarin). It went viral and one day I woke up with a few thousand $$ credits. It came with an expiration date — I gotta use them.

(2) Sponsorship from a Chinese travel company:
I took 1 sponsorship but the responsibilities that came with it became too much (x articles, y videos etc). Given a busy full time job, I decided to not take on more sponsorship.

(3) Exchange stay with skill sets (barter system): taking care of pets when hosts are traveling and painting pets.

Chenyu as a pet watcher
Chenyu as a pet painter

Overall, staying on Airbnb is more expensive than a lease but,
(1) it freed me up on weekend to explore new neighborhoods
(2) friendship and a sense of belonging cannot be measured by $$

For example,
Isa gifted me a ticket to Burning Man.

Aaron picked me up when I got strained in an airport, and showed my mom LA insider views.

Aaron explains to my mom surf shops in LA

Toby taught me practical drawing technique and encouraged me to pursue my passion in art.

Toby Klayman, my 81 year old art teacher, who became a friend and life mentor

Every trip has profound impact on me as a human being.
Experience > Things

More importantly, this journey gave me a sense of belonging to LA : a city that I used to feel distant to. Staying in 15 neighborhoods in LA made me a local — the hidden staircases, coffee shops, flower market or just share a breakfast with my hosts and live their life for 1 day.

Moving to San Francisco from Los Angeles made my project a lot harder to afford. Exchange stays with skill-sets or taking up the last 5 days of friends’ leases became my “alternative” airbnb.

air mattress became my common stay in SF

Besides finding ways to make the project affordable, I also took an unusual approach to meet the original cereal entrepreneur — Joe Gebbia.

By thinking outside the box and leveraging my special talent in painting.

In 2008, when Airbnb founders pitched to YC, Joe brought a cereal box along. Nate told him not to. But Joe sneaked it in.

That cereal box convinced Paul Graham
Sometimes, it takes the crazy ones an extra step to make unthinkable ideas happen.

I have been following Joe’s blog Simply since 2013. From his sharings of Eames Chairs, Heath Ceramics, Japanese craftsmanship, his talks about connecting strangers and building trust, I get what is important to him and why Airbnb is a design driven, host-empowered global community. I am inspired by his story-telling talent.

In late 2015, Joe happened to be one of the first followers of my instagram @365dOnAirbnb .

I wanted to share learnings but understand Joe is incredibly busy. I decided to make a plate of his dog Beloa physical item instead of emails.

That plate earned me a chat with Joe, during which I shared a bold idea about Airbnb as a“subscription service” to productize this lifestyle for urban nomads.

Joe said “You are incredibly persistent and passionate. ”

2. Optimism and Uncertainty

An entrepreneur’s life is like a roller coaster. Living on Airbnb and constantly moving is similar in many ways.

You can plan a perfect stay, but life is full of surprises and uncertainties. Stay positive in midst of uncertainties is an important quality.

Remember the blizzard in NYC? My flight was cancelled. Stressed with no place to fall back to. I learned to stay calm during uncertainties and find alternative accommodations.

A month later, I was asked to leave a meditation master’s house by his 4 years old daughter. Later I learned the family just went through a divorce. “You are not welcomed here.” still haunts me from time to time.

Have you been locked outside your own apartment? What about being locked inside a dark apartment in historic part of Bogota? The world was sinking at 5am when I was trying to catch a flight. Uber driver was calling me outside the steel gate, speaking only in Spanish.

Because work became so busy, iPhone autocorrected my location from “Burlingame” to “Burmingham” during a 1am stay-up-booking-airbnb-for-weekend session. When I opened Uber to commute, it says the pin was too far. I sat in a coffee shop, worried, texting friends to get a crash pad. I received many “rejections” but finally a friend opened her door to me.

There are countless difficulties that I had to overcome. As a result, I am optimistic because after this journey, what else should I be afraid of?

3. Be Tough and Go Out of Comfort Zone

I slept in art gallery, tree house, trailer, and all the inspiring homes. I also had my fair share of air mattresses to make the project affordable, but basic accommodation can be both tough and inspiring.

$15 / night air mattress in an art studio lighted up the artist within me
or this Surfer couch

As an urban nomad, one skill is to “bring your own wifi data”.

In Aug 2016, a friend offered me 5 nights of air mattresses in her newly vacant apartment. There was nothing but space. I borrowed an air mattress and comforter from the neighbor. I put cardboard to make the surface harder for my back.

a true airbed for 5 nights (borrowed wifi from the neighbor)

Then I realized wifi was cut off since my friend’s lease technically ended. I borrowed the wifi from the neighbor.

This is just one example of stepping out of my comfortable zone to ask for things —
Could I borrow your wifi?
Could I do laundry here?
May I store the suitcases in your closet over the weekend and pick up on Monday?

I had to borrow shoes to hike Koko Head in Honolulu because my only pair of sneaker is all white and will be ruined after immersing in red soil.

Host Victoria told me “ You can wear my shoes.”

I cried. I fell in a bathroom. I get up again. I become more resilient.

You gotta tough up. ” when I asked for a mosquito repellent. I became tougher and more self-sufficient.

4. Communicating with people from all walks of life :

A Chinese proverb says: it’s better to travel 10k miles than to read 10k books. Yet even better is to read 10k people’s mind. 读万卷书不如行万里路,行万里路不如阅人无数

An entrepreneur will interact people from all walks of life.

My hosts and their family ranged from 5 to 70 years old:
- from retired Cuban grandma whose son immigrated to Miami via a boat
- 20-something Scandinavian student who taught me how to spot the Swedes in LA
- and a Spanish architect who taught me how to make Eggs Benedict.

This is a journey to experience a full spectrum of humanity:
- empathy
- conflict
- culture difference
- helpless
- inter-dependence

I learned to ask permission before taking photos, to treat airbnb homes like our own, to treat others how we want to be treated.

I learned to receive criticism.

I learned that “Continental breakfast does not include eggs.”

I learned communicate clearly with a host when something went wrong.

I learned how to move on from awkwardness with a host, after getting locked inside an apartment. The night before, we enjoyed Colombian coffee together with his son. 5 hours later, I was locked helpless in his apartment. It was not his fault but it took some courage to talk to him again.

I learned to be a synthesizer to pass on the lessons to my Chinese readers.

Chinese female travelers gain courage from this project

Inspiring a new and humane way of travel in China is my mission. Now, I left full time job and focus on writing a book to be published in China in October 2017 — the book is about sharing a piece of life with a pilot, an architect and a painter. It contains facades of humanity , home decor inspirations but also values of holistic living.

CBN Weekly feature story (China’s equivalent of Bloomberg)

I hope to pass on the values I learned from each and every of Airbnb hosts to the ever growing China middle class who now has a reputation of buy, buy , buy.

The best teacher in life is life itself. Living on Airbnb for 365 days showed me possibilities of life. We are only limited by our own imagination.

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Chenyu Zheng

Artfully Translating Cultures | International Advisor & Brand Ambassador | Chinese Born Global Citizen 苹果姐姐