Nowadays all of that infrastructure exists as generic services on the internet you can throw together in a few days, with costs that scale with your needs. I recently watched a Q&A Mark Zuckerberg gave to the Harvard CS50 class in 2005 [0]. He explained that what made Facebook possible to start with was cheap hosted servers running open source software, and the ways that had changed over the previous decade. Nowadays with AWS and Google Cloud its even easier and cheaper. The same applies to physical goods now with eBay, Amazon Marketplace, Etsy, Shopify, running your own one-person media empire on Youtube, etc.
The negative connotations with "selling out" were the fact that you had to sell out creative control. You don't have to do that anymore. Dave Chappelle is rightly still sore about how he was cheated over the Chappelle Show. Nowadays you can build an audience independently, and that fact means that even if you do make a deal with big business, they know you're not as dependent on them anymore, so creatives have a much stronger hand than they used to.
So I really don't think this is down to the generation themselves, the world they live in is just different.