Brian Chesky’s Product Masterclass

5 Lessons on building great products

Building something new is hard, really hard, and advice, even from seasoned veterans, is nearly always conflicting. Do you ignore your customers, like Steve Jobs supposedly did? Do you chart a rigid course and tack headlong into the storm, no matter the resistance, like it seems Elon Musk does? Where does the aspiring entrepreneur look for an accurate map through the wilderness?

If you’re looking for an answer, I can think of no better person to start listening to than Brian Chesky, co-founder of Airbnb, travel site extraordinaire.

Airbnb started in 2008 and within 9 years, had a market value of $31B. In this interview with Reid Hoffman, Brian sheds a bright light on their approach to crafting winning products.


Lesson 1: Everyone Struggles

In the world of the overnight success, it’s easy to conclude that things are easy for other people. These inspired luminaries had the right idea at the right time, or the talent, or the connections. Whatever it is, we don’t have it, and that’s why we are struggling.

In these moments of self doubt, it’s instructive to recall that after a year and a half of grinding away, the Airbnb team had almost no customers. In other words, they didn’t have immediate traction and were definitely not the obvious hit they are today.

So what changed? Enter Paul Graham. Paul is the founder of YCombinator, a start-up incubator, and he prompted a fledgling Brian to “go to his users”.

“If I want to make something amazing, I just spend time with you.” — Brian Chesky

Lesson 2: You have to fight for your users

There are two mindsets that often get in the way of early product teams. The first is that as a founder you have to be unwavering in your vision, ignoring all signs to the contrary. The second is that a product should “sell itself”.

In the words of Reid Hoffman, “[Mark Zuckerberg] built a great product and users just poured in, right? Not exactly.” Reid continues, “you don’t start with 100M users, you start with a few. So stop thinking big, and start thinking small, hand serve your customers, win them over, one by one.”

Brian sums up both the challenge and the solution elegantly, “It’s really hard to get 10 people to love anything, but it’s not hard if you spend a ton of time with them.”

But wait, how can this work? After all, customer’s don’t know what they want! Faster horses and all that. I hear ya, but check out how Airbnb dealt with it...

Lesson 3: Let Go of Your Plan, Sometimes

One of the most challenging parts of building a new product is deciding what to put in and what to leave out. As product people we have our favorite ideas of what will work, and our ego can start driving a roadmap pretty quickly — but what if we didn’t have to have all the answers, all the time?

As Brian was designing the host experience, he discovered that “the roadmap often exists in the minds of the users who you design things for.” How liberating! Just listen and deliver what they want. Maybe sometimes letting go of the wheel and scooting over into the passenger seat is just what we need.

“Don’t guess at what user’s want, [Airbnb] reacted to what users asked for, and then they met the demand through a piecemeal process”- Reid Hoffman

Ok, but before we go crazy and outsource product management to our customer, let’s consider a key part of the job we can’t hand over to our users. It involves a knowledge not only of what a group of user’s want, but what is possible as well.

Lesson 4: Make Something Remarkable

Marketing is expensive. Of course, Elon Musk can tweet and get the eyes of the world on his next electric doodad, but most of us don’t have that luxury. In a world of attention scarcity, only the remarkable thrives. Which means, you need to engineer something worth talking about.

In Brian’s words, “if you want create something that’s truly viral, you have to create a total mindf*ck experience.”

But how? This is where Brian’s design background shines through. In this creative, experience crafting mode, he still relies on customers, not for the product ideas, but instead on the reaction to his vision. Instead of asking small product questions, he leaps to expansive questions about the experience, or more accurately, the potentially remarkable experience.

He asks, “what would it take for me to design something that you would literally tell every single person you’ve even encountered?”. By framing the question this way, he his digging for ideas to create an experience so great, that on a scale of 1–10, it would rate an 11. In exploring this mind blowing experience, he comes up with some truly crazy ideas, but he doesn’t build them all — he uses the 11 experience as a compass and backs his roadmap off to a 7 or 8 experience, which compared to the status quo, is in fact remarkable.

Here’s the insight — there are different mindsets at work at different points in the creation a winning product. Part of the reason why start-up advice seems so tough to discern, is that how you operate should vary widely depending on the part of the journey you’re on.

Lesson 5: Know Your Mode

Brian articulates the two primary modes of the entrepreneurial journey as “design the perfect experience and you scale it — that’s it!”

Simple, but not easy, right?

For Airbnb, this meant that creating magic for a single user was the essential 1st step. The hand-crafted, perfect experience, becomes the blueprint. From there, you can begin decomposing and automating the key elements as you grow. Reid Hoffman articulates why this is a natural progression, “you wouldn’t build a skyscraper before you build a solid foundation.”

Two modes of product development.

It’s easy to become confused, operating with the wrong approach at the wrong time. As product people, our minds naturally live in solution mode — we love platforms and scaling technology, and there’s time for that, but not before you cobble together something ugly that people care about. Here’s the rule — create magic first, then scale. [See also “Do Things That Don’t Scale”]

The Road Ahead

If you’re building a product, embrace feedback and spend a lot of time with your users. Reid reminds us that “passionate feedback is a clue that your product really matters to someone.” So get out of the office and enjoy this tough bur challenging phase of the journey.

“Your product changes less the bigger you get.” — Brian Chesky

No matter how many times you hear about how hard building a company is, it’s probably harder, but it’s nice to know that there are some patterns out there we can follow as we work to bring something beautiful into this world.

Thanks to Brian and Reid for sharing their hard earned wisdom.


If you’re interested, feel free to listen to the entire interview on SoundCloud.


Thanks for reading!

I’m passionate about how people design and build winning products. If you love product and design, let’s connect on Twitter and LinkedIn.