7 Lessons From Airbnb Co-Founder Brian Chesky’s “New Playbook”
New-age business and career lessons beyond product management, as heard on Lenny’s podcast
It’s safe to say Brian Chesky created quite the buzz a few months ago with his comments on “getting rid of classic product management”.
Curious, I followed the buzz to Chesky’s appearance on Lenny’s Podcast and ended up getting so much more out of it.
I’ve never felt the need to replay a podcast but on this occasion, I did.
Seldom, outside academics, have I heard someone speak with such rapid lucidity that it took some effort to keep up.
I was hooked.
I’ve been listening to Lenny’s podcasts for a while now so I’m not surprised that he was, once again, the curious and gracious listener.
I sensed a quiet acknowledgement of Chesky’s wide-ranging thought clarity. And it wasn’t surprising that Lenny put Chesky on the “near top” of his list of the most inspirational business leaders.
I know; We don’t need to idolise another tech leader and that’s not what this post is about.
I don’t agree with all of what Chesky has said but there’s something admirable about someone so committed to personal growth, they want to be able to change their beliefs — more on that in #7.
7 Takeaways
You must derive your takeaways but here are 7 of mine.
P.S.: Chesky saved his best for last.
1. Scaling Fast And Right.
Chesky hit the nail on the head when he talked about how “a fast-growing company can turn into a slow-moving bureaucracy”.
Faced with this predicament at AirBnb, he decided to make changes and deliberately built a functional operating model — one where teams share marketing and engineering resources where possible.
He did this so that all teams grow to “row in the same direction”, as he repeatedly stressed — an acutely under-represented ambition in my book.
To understand how this helps AirBnB, it’s important to understand “the general arc” of how scale leads to politics in the first place.
As a company expands, its new product teams will, at first, depend on shared resources. Absent these, they are forced to build their own, potentially accumulating technical debt.
New teams become divisions and division leaders are forced to advocate when faced with more dependencies.
As Chesky succinctly puts it, “your division is as successful as you are a priority”
Politics kicks in, creating distrust and restricted information flows.
In other words, bureaucracy emerges, which impedes a sense of shared accountability and results in complacency.
Many of us will find ourselves agreeing with the arc so far but most telling is his take on its culmination –
At its worst, such an environment could mean that engineering and marketing teams are so dissociated that despite successive feature releases and campaigns, customers have learned very little about the product.
Chesky believes adopting a functional model is one way to address this problem and that’s why he has redefined (not dropped) product management to incorporate marketing.
2. Product Management 2.0
I’ve previously written about customer-centricity and how — to quote Tony Fadell, co-creator of the iPhone — “The messaging is the product”. (See here)
At its core, that’s all Chesky is advocating for.
He is attempting to collapse the barrier between “marketing” (Product Marketing) and “engineering” (Product Managers) by mandating the latter be responsible for product marketing activities too.
“You can’t be an expert in making the product if you’re not an expert in the market of the product”, he argues.
His rationale is simple — say, you shipped a product and found it wasn’t successful, what would you change? The product itself, its messaging, the distribution channels?
By redefining product management, Chesky is forcing his PMs to build what can be marketed and sold well — a structure that could prove to be instrumental for sustaining product market fit.
After all, he argues — “If you build a great product and nobody knows about it, did you even build a product?”
The messaging is the product.
3. Marketing 2.0
Chesky’s analogies were thought-provoking and imaginative — reframing problem statements like only a designer could.
For instance, he likened performance marketing to a laser — sure it can light up a corner of a room but it’s not capable of brightening up all of it.
It’s not capable of building a brand.
In accounting terms too, performance marketing is typically classified as a variable cost because it’s a great way to meet targeted sales goals at manageable ROIs.
However, it doesn’t “create accumulated advantages” for the brand because it isn’t a fixed-cost marketing investment towards customer education.
Chesky advocates for companies to think about releasing features in “chapters” to build customer awareness of the broader product “story”.
Consequently, AirBnB developed a system of rolling bi-annual product releases, which all teams work towards.
Product management works with the communications team to “figure out the story” and it’s often the story that dictates the product.
Why?
Ultimately, it’s the story that will connect with customers and it’s the story that should become the North Star for internal teams.
Chesky’s views seem to be an evolution of another popular tech trend — one that promotes data and technical literacy as the chief skills for growth.
He advocates for PMs to go beyond their technical skills, understand the customer’s perception and build to market.
I’ve had “design thinking” explained to me before but I think Chesky schooled listeners on it without telling us he did.
4. The Significance Of Assertive Leadership
Chesky strongly believes founders should be involved “in the details”.
You might think that’s a great euphemism for micro-management, which I suspect may be true in some ways.
It also reveals a greater entrepreneurship lesson — the significance of being a leader who’s open and assertive about their vision.
Allow me to elaborate.
Chesky talks about being forced to delegate decision-making as Airbnb grew and how aforementioned politics were slowing down the company.
It’s why he decided to stop pushing decisions down.
He wanted to define a unified vision that all employees could get behind and demonstrate behaviours that became the foundations of Airbnb’s culture — a “shared consciousness” as he puts it.
Chesky believes founders shouldn’t away from asserting their vision because that’s what teams need to “row” in the same direction.
Perhaps, there’s a right time to be a democratic leader and equally to be one that brings teams together.
Chesky talks about doing so by having few management layers and going through a system of regular, transparent reviews.
“If you can’t row in the same direction, why are you all in the same company?”, he implores.
4. Thinking Bigger And Getting It Done.
This one gave me a completely new frame of reference.
We learn that Chesky has perpetuated a culture of “adding a zero “ at Airbnb and Lenny asks what he has learned about thinking big in the process.
For Chesky, it was not about hitting the number — it was about pushing people to visualise the problem at such a scale that it forces them to think differently about the problem.
How?
When you think about solving problems at a presently unrealised scale, you have to start by assuming the current process won’t work.
You have to deeply understand the problem and break it down into its components.
“Adding a zero — at least conceptually — helps people understand the problem”. Ask yourself what would it take to add another zero?
He advises leaders to follow through by “setting the right pace”, which isn’t governed as much by hard work as it is by decisive work.
6. Prioritising Happiness
When asked for tips on avoiding burnout, Chesky talked about his efforts to live in balance with health, work and relationships.
And although I fully agree with it, this isn’t about productivity hacks or dietary habits.
What I was particularly surprised by, is how deliberate Chesky was with his relationships, citing an 85-year-old study on the secret to happiness (Harvard Study of Adult Development, 1938 — 2017).
He admitted his entrepreneurship journey left him feeling isolated as he got stuck in a loop of being too busy to meet friends and them assuming he was too busy to meet.
Since then, he’s been more intentional about scheduling regular trips with his high school and college friends. He regularly visits his sister in New York and was speaking from her 2-bed flat at the time of recording.
“If you imagine your life is finite and that you’re not going to be here as long as you thought you would be — it’ll completely change the way you prioritise your time and who you spend it with”.
He relates this to business too — leaders spend too much time reacting to people, rewarding specific behaviours.
More importantly, he warns, you may end up disregarding the introverts equally deserving of your attention.
7. The Unexpected Secret To Staying Motivated
The clincher, for me, was Lenny’s final question – “How do you stay motivated to keep growing?”, he asks.
Chesky speaking of his child-like curiosity to learn deeply, which compels him to study the “source of things” that interest him.
He talks about being an advisor to OpenAI CEO, Sam Altman and yet admitting – the more successful he becomes, the more of a beginner he tends to feel.
Does the Co-Founder of Airbnb experience Imposter’s Syndrome? I wondered.
Turns out – he just has a very different framing of it.
When you scale certain peaks to encounter new frontiers of knowledge, you will naturally start to feel like a beginner, he explains.
To quote his timely reference to Pablo Picasso, “It took me 4 years to paint like Raphael but a lifetime to paint like a child”.
Try to view the world like one and be a beginner, he advises.
His final thoughts reveal a refreshingly earnest aspiration –
Chesky “sincerely hopes” he’s able to amend some of what he has said on the podcast because it’d mean he has learned something.
It’d mean he has something to keep him going.
How’s he going to do that? By being curious.
In closing, he quotes Bob Dylan: “An artist has to be in a constant place of becoming”, referring to his own identity as one.
Conclusion
Chesky does not come across as the typical tech leader. I don’t condone idolising leaders but I found his earnestness relatable and his adaptability admirable, leaving much to learn and make your own. Noteworthy lessons:
- Adopt a lean, functional operating model where teams share engineering resources to scale fast and right
- Redefine product management to include marketing activities so that you build to-market
- Ensure marketing is synchronised with product releases so that customers are progressively educated
- Leaders/founders should not feel shy about asserting their vision as they establish foundational practices
- Prioritise relationships to avoid burnout and be proactive about who you spend your time with
- Don’t be afraid to be a beginner: follow your curiosity to evolve your knowledge base and stay motivated
I always learn a lot from Lenny’s Podcasts but this was probably one of the top ones on my list. I’m sure everyone had their takeaways, what were yours?
You can find this episode of “Lenny’s Podcast” on Spotify.
