I think they are doing it right. Just find a niche and work at it progressively through life. No need to raise $100M D Rounds, no need to have an explosive exit, whatever. I think it would be nice to just steadily have six figures, work on something I love and live life (a la Basecamp). Most of all: Have complete control of your destiny. No investors, no bosses, etc.
I know hindsight is 20/20, but it's interesting to me that they could've created Airbnb, as they had both the reach and finances to potentially create a side-project that was specific to short-term rentals. They already had sublets and temporary rentals as a sub-listing since forever. I know that Airbnb comes across as warm and fuzzy hosts who engage with guests, but it's progressively more commercialized with a good…
Craigslist has 50 employees and minimal vetting of anything. It's great for what it is, but I would never use it to rent anything site unseen.