Read time: 3 minutes 30 seconds

This weekend I stayed 2 nights in a cosy wooden cabin in Minnamurra Rainforest.

Reading. Journalling. Hiking. Reflecting.

An ideal way to spend reclaim 72 hours.

A highlight: Reading through hundreds of thoughtful responses to our recent survey.

To everyone who submitted feedback so far - thank you. Strategy Breakdowns is still in its infancy, and you’ve played a direct part in shaping what the next few years look like.

— Tom

P.S. Our audience survey is still open, and I’d still love your input. It takes just 3 minutes, and is nearly entirely multi-choice (like all surveys should be).

Thanks in advance!

How Airbnb gets users on autopilot

Chess Move

The what: A TLDR explanation of the strategy

When Airbnb was founded, most traffic for peer-to-peer accomodation demand was going to Craigslist.

But Craigslist wasn’t a dedicated accomodation network. It was a general advertising forum, enabling anyone to post a ‘classified ad’ for anything, and for any interested buyers to contact those advertisers.

Its ‘open’ nature was a cornerstone attribute that led to its widespread adoption.

But also a vulnerability to competitors optimising for specific verticals.

Breakdown

The how: The strategic playbook boiled down to 3x key takeaways

1. Bootleg ‘integration’

Airbnb knew that Craigslist had a massive user base actively seeking rentals.

In order to generate more impressions (and improve completion rate) on Airbnb listings, they constructed a seamless flow for hosts to cross-post their listings to Craigslist.

When users posted on Airbnb, they were given the option to “post to Craigslist”, which generated a pre-filled listing template.

Under the hood, the bot: visited Craigslist → filled out a handful of forms → created a draft listing → built an HTML template → copied the unique URL → served it back to the user for publishing.

To make the flow as frictionless as possible, the bot automatically added a compelling title, detailed description, category, location, high-quality images, and crucially - a direct link back to the listing on Airbnb’s website.

By equipping hosts with tools to broadcast their rentals, Airbnb tapped into Craigslist’s vast traffic base, funnelling new users back to their own site.

2. Automated outreach

Airbnb also realised that every short-term rental listing posted directly on Craiglist represented a potential new host for Airbnb’s marketplace.

They built an automated outbound sales script that reached out to new Craigslist advertisers, inviting them to try Airbnb instead.

Notably, the email didn’t come from Airbnb directly. Instead it came from a pseudonymous sender like “Jill Demi” (“[email protected]”), recommending (as opposed to inviting) the host to “check out” Airbnb.

When this tactic caught unfavourable media attention, Airbnb explained they had contracted a remote sales team to “acquire listings through person-to-person sales, but their efforts were largely ineffective."

They were unaware of the specific tactic being used, and forbade it when it came to their attention.

3. Stick the landing

In order to convert the traffic they were siphoning from Craigslist, Airbnb focussed on building a dramatically superior experience for incoming users.

Craigslist had a notoriously unappealing design.

→ Airbnb’s co-founders had design backgrounds, and developed a significantly more aesthetic and intuitive surface.

Craigslist made it difficult to navigate to relevant listings based on renter preferences.

→ Airbnb had accurate filtering for rental features, and positioned each listing on a map.

Craigslist had inconsistent listing information.

→ Airbnb ensured listings had detailed descriptions and high-quality images.

Craigslist users were mostly anonymous.

→ Airbnb built ‘host profiles’, with their picture, a bio, and reviews from previous guests.

Craigslist required back-and-forth emails to align on available dates and pricing.

→ Airbnb featured an interactive calendar that updated automatically, and a transparent breakdown of pricing and platform fees.

Craigslist offered no payment mechanism, and was prone to scams.

→ Airbnb facilitated simple and secure card payments on-platform.

Inviting. Intuitive. Trustworthy.

Once users made the switch, they had little reason to go back.

Rabbit Hole

The where: 3x high-signal resources to learn more