Reading his about page should give you a clear indication why. Almost the first sentence is "I dropped out of college to apprentice under Robert Greene, author of The 48 Laws of Power." I've always been extremely wary of people who pursue power for its own sake, before they're even fully formed humans. A common technique they choose to acquire power is hucking drivel to other people who view the world the same way - commonly writing in those platitudes about overcoming adversity. I've literally never heard of this guy, but just from reading this hn post, I can almost guarantee you he has published a book that can be summed up in about 2 sentences but is inexplicably 125 pages.
Seeing titles like "Courage is Calling", "Stillness is the Key", and "Trust Me, I'm Lying" only make me more confident in my point, not less. But, I'm not going to buy these books just to see if my hunch developed over 15 seconds is correct.
I find Ryan Holiday to be pretty annoying as a marketer, I used to be on his email list for book recs but I got frustrated when the vast majority of his recs were books written by white men (I dont have an issue with books written by white men, but I do see it as a red flag when someone only really consumes content from one perspective).
But I did find "Trust Me, I'm Lying" to be a fascinating look into how to fake a grass roots campaign and create the illusion of virality (basically a step by step guide to fake it till you make it).
I also found his book on Peter Thiel/the Hulk Hogan case (Conspiracy) to be a really interesting look into a lawsuit with pretty major implications for the future of journalism. Although his musings on Thiel's motives/morality/approach seemed to overlook the idea that maybe there just shouldnt be billionaires.
Overall I would say he has interesting insights on specific situations but in general his thinking is fairly unimaginative/limited to manipulating the current system without actually questioning underlying assumptions.
I find people's opinions on Thiel to be an interesting litmus test: Seeing him as morally bad is one thing, and thinking there shouldn't be billionaires is a reasonable view, but if someone absolutely cannot or will not see that he was the wronged party when Gawker outed him without his consent while he was in a country hostile to LGBTQ+ people, they're morally blinkered at the very least.
People who judge the morality of an action based on characteristics of the people involved have replaced their moral sense with tribal affiliation. That, or they're immature black-and-white thinkers who cannot understand that even someone who is generally bad can be on the right side of a specific issue.
I agree, what Gawker did was wrong. But being wronged once doesnt excuse Thiel's actions. And (more importantly imo) the larger issue is -- are you comfortable with a random person having enough money/power to threaten freedom of the press?
Also Thiel is far from the only person to be outed, the only difference is his reaction/how much money he has. Do you think its equally wrong that Wired outed Naomi Wu while she lives in a country hostile to LGBTQ+ people?
> And (more importantly imo) the larger issue is -- are you comfortable with a random person having enough money/power to threaten freedom of the press?
OK, let's see if we agree on the basic timeline:
1. Gawker outed Thiel.
2. Gawker released the Hulk Hogan sex tape.
3. Thiel funded Hulk Hogan's lawsuit against Gawker.
4. Gawker lost the lawsuit.
Is that accurate? If it is, the problem isn't that Thiel funded the lawsuit, the problem is that Hulk Hogan needed Thiel to fund the lawsuit for him to prevail in court and get justice for the wrong Gawker did to him.
I'm for taxing billionaires. I'm also for privacy and people being protected against paparazzi. Those things don't come into conflict unless someone sees a billionaire funding lawsuits based on the right to privacy and decides that anything a billionaire does must be wrong, prima facie.
> Do you think its equally wrong that Wired outed Naomi Wu while she lives in a country hostile to LGBTQ+ people?
I found “The Obstacle Is The Way” useful and accessible, and I went on to read Marcus, Seneca and others. I appreciate the introduction Holiday provided.
Any combination of factors that allows the opening of something like an independent bookshop is A-OK by me. Maybe Tim Ferriss will open a wood-fired pizzeria.
I said I gained "more confidence", not that I am confident. After all, like I said, I put about 15 seconds of thought into it, which was how long I knew that Ryan Holiday as a person even existed.
But I think I get it. I'll make another assumption, still in about 15 seconds, this time about you: You like Ryan Holiday. You subscribe to his mailing lists, have read his writings, and may have a couple of his books on your shelf. Your views on the world are aligned with his. So you're offended that I made a negative assumption about him because he's "your guy".
I think it's very easy to make assumptions and it's good to have heuristics to make life easier. But it's not wise to double down on them.
(You're half wrong again. I dont think stoicism that Ryan Holiday talks about is the greatest philosophy. I have read a couple of his books but dont subscribe to him. Anyways I would love to buy you a copy of his work if you want to read and judge for yourself.)
