Dropbox and AirBnB may currently have the biggest valuations, but I imagine it would be difficult to say they are YC's biggest successes (both in financial and historical terms).
If YC had funded Paypal, they would have made a nice return with the $1.5B eBay acquisition. But their valuation would've ended there. In reality though, they currently make up 44.9% of eBay's revenue. eBay is a $63.45B company.
I don't know YC's policy on holding stock in the acquirers company after someone in their portfolio is bought out, but assuming they keep stock, a company acquired by Google a few years ago which allowed YC to accrue a few million dollars worth of Google stock could very well be their biggest financial gain in 50 years.
A lot of acquisitions are funded via stock. I imagine YC owns a sizable amount of publically traded stock through acquisitions.
My point though is that in 50 years, their minute percent ownership in Google they received via an acquisition could be worth far more than their much larger percent ownership in Dropbox.
If YC had funded Paypal, they would have made a nice return with the $1.5B eBay acquisition. But their valuation would've ended there. In reality though, they currently make up 44.9% of eBay's revenue. eBay is a $63.45B company.
I don't know YC's policy on holding stock in the acquirers company after someone in their portfolio is bought out, but assuming they keep stock, a company acquired by Google a few years ago which allowed YC to accrue a few million dollars worth of Google stock could very well be their biggest financial gain in 50 years.