More specifically he says you're probably not working enough if you're running some sort of personal narrative that you're all that business-wise or ever going to be a multi-millionaire/whatever.
He frequently says that sort of life is not for everyone and people who are happy doing a dayjob and devoting their time to personal pursuits should be envied. But if you want to be chasing the beasts of big money and big business and be all about being the big-I-am, you better be working long and hard.
I don't know where I read it, but I like the idea of life stages. When you're in your 20's, hustle and grind and work a lot. You will never have as few obligations and as much energy as you do when you're young.
Take advantage of youth.
But if you're a 40-something with 3 kids and spend 16 hours a day grinding and working, and no time spending time with your family ... don't. Slow down.
A lot of GaryVee's advice is aimed at people who have few responsibilities and obligations in life and spend 5 hours every day watching TV or playing video games and complain that success doesn't come. Yeah, obviously it doesn't. Work harder.
If you're already working harder, you're not GaryVee's audience. How do you even have time to watch his stuff? ;)
I honestly don't believe that he took less than a weekend off during his entire twenties. The way that statement comes across to me is hyperbole used to drive home the main point of "stop complaining and trying to look successful, and start working".
At ~12:50 he also says "it's okay to enjoy a little bit now too" and that the advice he'd give to himself at 25 is "go have fun". He tends to provide more realistic advice than a lot of other people who produce this type of content, at least from what I've seen.
> So you are playing a fake narrative instead of putting in the actual work that's needed to actually pull it off.
> Wishing instead of Executing.
Last week he told someone who took a weekend off that that was more time than he had taken off for his entire twenties.
[1] https://www.youtube.com/watch?v=qRj144Gd7EA