YouTube was still in its infancy in early 2008, along with how expensive even decent capture equipment was. Stuff like Patreon can exist now because the cost of entry has come way down and ease of access has increased tremendously.
Yup.
The internet was so different back then. So many services today you can use simply didnt exist. Youtube wasn't really a way for people to make money and still had a 10 minute cap for crying out loud. Ustream was the premier live streaming website. I dont think Twitch even existed.
For a lot of stuff you simply needed to build that stuff yourself. And yeah. Capturing console video was a multi thousand dollar ordeal and so was live streaming. Jeff and Co couldnt simply launch the site on their own.
Also there are so many roads Jeff could have gone down after the GameSpot split.
I remember Jeff mentioned before that he had a offer to be the games news guy for Penny Arcade that Ben Kuchera ended up filling. Or maybe he could have become a consultant.
He was lucky that Cnet founder was starting Whiskey and Ryan and Dave where buddies and they could make that happen