Holiday: The Obstacle Is the Way didn't hit bestseller lists until 2019
Ryan Holiday · The Daily Stoic's Ryan Holiday: How smart people lose their way | Masters of Scale · Oct 31, 2025 · at 18:41
Author Ryan Holiday explains how 'The Obstacle Is the Way' scaled slowly via organic word-of-mouth rather than immediate commercial success.
0:00 / 0:03exact quote · 3.8s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“It didn't hit a bestseller list until 2019.”
quote is from the automated transcript, cleaned for reading: filler sounds and stutters are removed, nothing is rephrased. names can be misheard (the analysis reads context, assessments check outside sources). how →
More from Ryan Holiday
Holiday: Elon Musk is a genius who broke his own brain
“Well, Elon is one of the smartest people on the planet, right? It's like, to say that Elon Musk is not smart, which some people have started to say, it's like saying he's not rich. Like, it's just, it's a fact, you know? He is a genius in many, many ways. He i…”
Holiday: Podcasting breeds sloppy thinking due to non-adversarial formats
“Podcasting as a medium is very enticing for, like, sloppy thinking also, because it's not like being grilled by a journalist, you know, for the most part, like, it's mostly non-adversarial, and same with most public speaking, like, you were invited, they want …”
Holiday: Productivity content serves as an entry funnel for philosophical ideas
“When I make one that's like 10 stoic strategies for, you know, owning the day, that's going to reach more people and that You can't talk to them about the social justice side of things until they've heard of it first.”
Holiday: Leaders need constraints and dissent rather than total freedom
“You think you want freedom of movement and supporters and advocates, but actually what you need is to be challenged and you need boundaries and you need limitations.”