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The Bulwark Podcast

Ryan Holiday: Life Is Too Short to Be a Bootlicker

The Bulwark Podcast

The Bulwark

Politics, News, News Commentary

4.68.9K Ratings

🗓️ 24 October 2025

⏱️ 69 minutes

🧾️ Download transcript

Summary

Members of the administration, like Stephen Miller, who spend hours every day kissing Trump’s ass look so pathetic—but since the time of the ancients, courtiers have gone to great lengths to degrade themselves before the vain and vindictive. And one lesson for the ages is to not compromise with an extortionist: it will only lead to more extortion and more pressure because the extortionist wants everything. Meanwhile, Elon’s brain is broken, Peter Thiel spends too much time at dinner parties, Trump’s media diet allows no time for presidential reflection, and authoritarians can be seductive. Plus, Tim sees the redistricting fight looking better for Democrats, and argues that the best way to shut down the talk of a decrepit Trump running in ‘28 is to make sure the Dems win the House in 2026.

Ryan Holiday joins Tim Miller for the weekend pod. 

show notes

Transcript

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0:00.0

Building a coffee business?

0:01.5

Serving the best Americano in town is up to you. But winning back time and growing your business, leave that to sum up. Take orders and payments anywhere with the new sum up terminal. Turn occasional customers into regulars with a free loyalty program. And with the sumup point of sale system, you'll always know when you're running low on your best selling blends. Visit sumup.co.com to learn more. Hello and welcome to the Bullwark podcast. I'm your host Tim Miller. Our guest today,

0:24.4

Ryan Holliday, is a friend of mine. He's awesome. And what we're going to do is try to take a

0:30.5

step back a little bit from the new cycle, see if we can find any wisdom from the ancients on how

0:36.3

to process everything that's happening. I also talk

0:40.0

with him a bit about some controversies he got in with the administration. So it's going to be a

0:45.9

great podcast. But I had a little bit, a few politics notes that I had to get to you guys first

0:50.7

before we took you into the weekend with a little bit of Zen. I will start with some

0:55.4

good news. How about that? The redistricting battle is looking better for the Democrats than even

1:02.2

it was last Friday when I was talking to Peter Hamby about this. And so I want to go through a

1:06.2

couple of developments with you and then make a plea to some of the remaining Democrats out there who've

1:11.7

been a little slow to the punch on this. The big news came yesterday, which is that Virginia

1:16.9

is starting a process that could yield three new Democratic seats, assuming the party holds

1:23.1

on to the state legislature, the state house, this coming November here, so in a week or two.

1:28.8

So that makes those elections even more important than they already had been.

1:34.3

Kudos to the Democrats in the state legislature.

1:36.8

I was kind of wondering if this might be possible.

1:39.2

I figured that Abigail Spanberger, who's running, didn't really want to make her campaign

1:43.5

for governor about

1:44.7

redistricting. But just because of some machinations of kind of how you got to get this process

1:50.4

done legally and constitutionally, the legislature had to start the process without her. And they

1:55.6

did so yesterday. So assuming that my girl Abigail Spanberger is fully on board for this,

...

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