Introduction

This week I found myself deep into the mind of Brian Chesky, Co-Founder of Airbnb.

Two weeks ago, I stumbled into this concept of ghostwriting. You can get paid to write on behalf of intelligent business leaders. Who knew?!

A friend connected me with Tom, a writer that has his own newsletter, ghostwrites, teaches writing to others, and advises companies based on his research. After a great conversation learning about the world of online writing, Tom mentioned that he could use some help with research for a current project.

I jumped on the opportunity - which led me to listening to Brian Chesky talk for 15+ hours this past week.

I’m excited to share a few lessons that I will incorporate into my business and life.

4 Lessons from Brian Chesky

Lesson 1: Build things that don’t scale

Sounds counterintuitive at first, but here is what he means - perfect your product while you are still small and can stay agile.

Brian received this advice from Y Combinator Founder Paul Graham, “It’s better to have 100 people that absolutely love your product than 1,000 people that kind of like it”.

Back when Airbnb was only in a few cities, Brian would fly to New York and pretend to be a photographer for hosts. He would gather in-depth feedback on the platform to understand every pain point and find out what was missing. He used this time when they were still small to iterate and make the best possible product.

Then once you have 100 people that love your product, growth begins organically because of network effects.

This is a great use case for long term thinking by not rushing a product to market and letting the compound effect take place.

I’ve starting applying this concept to a potential ghostwriting business. It starts by talking to dozens of business owners, creators, and corporate executives to understand their current copywriting challenges. As I start working on projects, I’ll learn where the pain points are and adjust my offerings accordingly.

Lesson 2: Hiring is the most important decision you will make

Brian interviewed the first several hundred employees at Airbnb.

The main question he would ask himself was, “Would I want 100 people just like this person working here?”

People you hire contribute to the organization culture and will be responsible for hiring the next wave of employees. This goes back to the saying “You are the average of the 5 people you surround yourself with”. Engage with people who share similar values and contain qualities of the person you want to become.

This has been a main driver for a lot of my decision making recently - from choosing which friends to hang out with to finding mentors and business partners.

Lesson 3: Establish a set of principles to optimize for

In the early days of Airbnb, Brian created timeless principles that are foundational for company culture and guide decision-making.

When the COVID-19 Pandemic shattered 80% of revenues in 8 weeks, Brian leaned on his core principles to make difficult decisions (see a few examples below)

1. Be decisive

2. Act with all stakeholders in mind

3. Do the right thing

Based on these principles, Airbnb decided to refund all guests their money back even if it was against the cancellation policy. This significantly hurt the hosts, so the company also paid out $250m to subsidize a portion of their lost income.

Airbnb was optimizing for doing the right thing and acting with all stakeholders in mind, not just their shareholders.

I have my own set of principles that help guide me in life and business:

1. Be deliberate in decision making

2. Control perceptions and accept what is outside my control

3. Run towards fear

4. Align what I think, say, and do

5. Take consistent daily action

6. Believe in the end of the story

Following these principles will lead to very different outcomes than if had principles like create a stabile environment or focus on high yield tasks.

Lesson 4: Apply the 10-star service concept

When designing a product, Brian thinks above and beyond the traditional 5-star rating scale.

5-star service is what customers expect. But Brian shoots for 10-star service - things that most customers wouldn’t even dream of. Here’s an example:

• 6 stars: You get to your Airbnb and there’s a bottle of wine and fruit waiting for you with a hand-written note

• 7 stars: A limo picks you up from the airport, and when you get to the house there’s a surfboard because the host knows you like surfing

• 8 stars: You ride back from the airport on a giant elephant and there’s a parade in your honor

• 9 stars: You land at the airport and there’s 5,000 teenagers cheering your name and you do a press conference in the front lawn of your Airbnb (”The Beetles Check-In”)

• 10 stars: Elon Musk picks you up from the airport and says “we’re going to space”

8+ star service are not realistic but it stretches your creativity on how to improve the product from traditional expectations.

This got me thinking how I can apply this to other areas of my life.

When a friend comes to stay with me in Austin - how can I make it a 7 star weekend?

Planning a date - what activity can we do that is unconventional?

Hosting an event for charity or work - what could I do that nobody expects?

Final Thoughts

After listening to podcasts with Brian ranging back to 2015 until the present, one thing stood out to me: consistency.

In 2015 Airbnb was valued at $1B. Today, it’s valued at close to $100B. A lot has happened during that timeframe so the stories vary, but he still references the same underlying principles now as he did in 2015.

Studying Brian has opened my eyes to the importance of design (in all aspects of life) and establishing a set principles that contribute to how we operate both personally and professionally.

My favorite Brian Chesky podcasts

Master of Scale (Oct 2017)

Out of the Crisis (May 2020)

Jordan Harbinger (Sept 2021)

Lenny’s podcast (Nov 2023)

Thank you for reading! As always please reply and let me know what resonated with you, what you disagree with, or what this made you question. I love chatting about this stuff!

Cheers,

Andrew