He had a challenge this year on flipping items from free section of Craigslist, yard sales, thrift stores for profit.
What is this all pretty much useless? He gives away 99% of information for free (I've been watching his videos for 3 years). He comes out with a book once every two or three years that's a synthesis of mostly what he has already given away. Think of Tim Ferris' book Tools of Titans.
Do you think advise like work to make money so you can fund your own businesses if no one else wants to fund you is useless? How about figuring what you want and reverse engineering the path? Or to successful entrepreneur who doesn't find money rewarding anymore, that it's good thing, because most people never get past the phase of chasing money, that he can focus on what he wants and finds meaningful.
Sources? I suspect origin will be himself. What does it mean to invest early in Facebook? FB completed its last traditional round in 2006. Personally, I’m a fan of GV, but it’s weird when someone says they invested early to mean outside of an angel investment / funding round. I’d be surprised if he was part of a FB round. Instead like other social media entrepreneurs he likely picked up some on secondary market or directly from a shareholder 2007+ as much for the narrative as the financial investment.
Crunchbase does list him as Angel/Seed Round investor in Uber in 2010[1].
[0] https://outline.com/8HHZFF
[1]https://www.crunchbase.com/funding_round/uber-angel--c76f942...
Anything pre ipo, they’re going to be the first 1% of shareholders if the company does well. And many times you can’t even buy into those rounds without the right connections. Early is subjective vs if he said he was an angel round investor.
He runs a really successful marketing company (https://vaynermedia.com/) a sports agency (http://vaynersports.com/), gives most of his content away for free on YouTube, wrote 4 books and is a NYT + Wall Street Journal Bestseller, and is pretty respected in the early stage Silicon Valley investment community (https://www.crunchbase.com/person/gary-vaynerchuk/investment...).
Like most things on hacker news, don't speak on something unless you know what you're talking about.