Bert Kreischer on sobriety, stoicism, and letting go of outcomes

Executive overview

Bert Kreischer has spent his career in an industry where success is measured entirely by audience response — yet he's wrestling with how to stop letting that response define his day. Ryan Holiday and Kreischer explore the gap between what you can control (the work, the effort, the craft) and what you can't (rankings, reviews, the internet's verdict).

The conversation circles a core stoic problem: how do you care enough to do great work without being wrecked when the outcome disappoints?

Detaching your sense of success from other people's reactions is the real practice — harder than any physical discipline.

The witching hour and sobriety

• Kreischer is currently sober for health reasons (medication-related), not by choice — which makes this stint feel different from previous ones
• He identifies 5pm as the "witching hour": not the morning after, but the daily pull toward the night ahead
• When sober, his "blinders open up" — he notices the world around him instead of narrowing to immediate discomfort
• He describes a exercise bulimia pattern: drinking at night, then punishing himself in the gym the next morning — and admits the shame-fueled workout might hit harder than a sober one
• Journaling started at 53, motivated by wanting more original thoughts

Waiting for results

• Both Holiday and Kreischer describe the same trap: wasting a day either doom-scrolling for news or euphoric/devastated once it arrives
• Holiday's counter-move when his book Stillness debuted: saw the unread texts, went swimming and journaled first, got the news after a good morning — he's prouder of that discipline than the number-one debut itself
• Kreischer's version: woke early the morning Free Burt launched, tried not to check Netflix, failed, found the show debuting at number two — then immediately lost the gratitude to habit
• The problem isn't the bad news; it's that the good news doesn't stick either

Defining success on your own terms

• Holiday's reframe: by the time a book is out, you've already captured 95% of what the project can give you — the craft, the challenge, the growth, the advance
• Royalties, awards, and reviews are all "extra" — and they're the parts outside your control
• For standup, Kreischer pushes back: the audience's laugh is the product, so audience response can't be fully dismissed
• The practical question: is your definition of success weighted toward what you controlled, or what other people decided?

The Tom Brady roast and trusting your own experience

• Kreischer and Tom Segura performed at the roast; Tom came back the next day saying "the internet says we bombed"
• Kreischer's position: "I was in the room. Not one person told us we bombed. Why would we listen to the internet over our own experience?"
• This became his first real lean into stoicism: making your own direct experience the primary evidence, not the aggregated reaction of people who weren't there
• He acknowledges the limit: if there are no laughs in the room, that's real data — but online commentary about a live event is not

Wanting a Seneca in real life

• Kreischer says he's jealous of people in recovery who have sponsors — someone to call before doing something dumb
• He wants the equivalent: a wise older figure (a "70-year-old man") to serve as a check on impulsive decisions
• His current sober period has given him a glimpse of what that clarity feels like from the inside
• The goal he keeps returning to: staying playful, keeping the "sparkle" in daily life without needing alcohol or external validation to feel it