I found it difficult to deal with clones of Groupon, as it felt demoralizing to see others copy our concept without the same passion for building a startup.

One of my biggest mistakes was not documenting our culture and values early enough, which led to misunderstandings about responsibilities within the team.

While running 'The Point', we launched Groupon as a side project, which allowed me to shift my focus without admitting that 'The Point' was failing.

The mistake I made was delegating decisions to the wrong level in the organization, which hindered our ability to ship great products.

When I was at Airbnb, I focused too much on my own approach and didn't partner enough with the customer support leadership team, which hindered building true support for our initiatives.

The decisions that seemed like the worst business choices often turned out to be the best, especially when they were aligned with core values.

One of the biggest mistakes I made was relying too much on venture capitalists' advice instead of trusting my own vision.

I made a significant mistake by not investing in Facebook when I had the chance, which taught me to recognize exceptional founders without overanalyzing.

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.