In hindsight, we shouldn't have launched with a free service in the first place; we ended up becoming a truly premium model based on ticket prices. We won't monetize a free product, which allows us to undercut our competitors and led to thousands of free events being published on our platform.

We started with a freemium model, but realized it distracted us; we shifted to a paid model and consistently increased prices over time, which helped us focus on serious customers.

Initially, we thought we were on the path to success, but I later realized that we were not converting users into paying customers because we were too focused on fundraising and PR instead of creating a product that people actually needed.

We initially tried offering photography services for customers, but nobody wanted to pay for it, which was a failure for us.

Despite having a promising product, we struggled to secure investment, leading us to consider launching on Kickstarter, which was suggested by Paul Graham. We built our Kickstarter page and filmed the video ourselves, starring our friends and interns.

At that time, there wasn't a clear monetization route for Reddit; we didn't have advertising or any real way to generate revenue, so we operated as a lean startup to survive with scarce resources.

In hindsight, we didn't track revenue effectively; we focused on usage metrics, which made it unclear how many monthly active users we needed for fundraising.

After our initial launch, we didn't see immediate success and even explored creating a roommate matching website before pivoting back to Airbnb.

I launched Airbnb in August 2008 without a presentation deck, relying solely on the live website, which ultimately failed during a pitch to an investor.