Before Paypal he sold a rudimentary yellow pages search engine to Compaq for $305 million so that they could merge it into their search engine. Compaq managed

Before Paypal he sold a rudimentary yellow pages search engine to Compaq for $305 million so that they could merge it into their search engine. Compaq managed to sell AltaVista for $2.3 billion 6 months later and not long before the crash so maybe it wasn't the stupidest move on their side.