Ruthless Podcast: "How Did We Get Here? What’s with Holmes ‘Stache? - Ruthless Q&A"

Date: December 25, 2025
Hosts: Josh Holmes, Comfortably Smug, Michael Duncan, John Ashbrook

Episode Overview

On this special Christmas Day episode, the Ruthless crew delivers a festive "present" to their audience: an extended, candid Q&A session. The fellas answer listener-submitted questions, delving into their personal backgrounds, careers, inside jokes, and the lore behind Holmes’ mustache. The vibe is light, irreverent, and chock full of insider political knowledge, blending serious wisdom with the group's signature humor and camaraderie. While policy and political war stories abound, the real treat is the peek behind the curtain into how these voices of the next-generation conservative movement came together.

Key Discussion Points & Insights

1. Christmas Traditions & Gift-Wrapping Challenges

Timestamps: 02:22–04:15

• Smug’s Wrapping Philosophy: Smug can’t wrap gifts and doesn’t use tissue paper. He simply leaves gifts in their original store bags under the tree:

  "I'll get the present, and then whatever the store bag it comes in, I leave it right next to the tree. If you look at it, it's on you." – Comfortably Smug (03:01)

• The guys riff on "being the gift" to their families, with tongue-in-cheek references to putting a bow on themselves or simply celebrating their own continued presence as a present.

2. How the Ruthless Crew Got Here — Bios, Origin Stories, and War Stories

Timestamps: 04:38–28:36

a) John Ashbrook

• Started as a congressional staff intern and driver in Ohio, learning immense lessons at entry level:

  "You can't beat yourself up because you're starting on a low level. That's where everybody starts." – John Ashbrook (06:51)

• Worked in House communications, press secretary for talk radio, eventually moving to Senate Republican leadership comms through difficult times (post-2006 major losses, during the financial crisis).
• Ashbrook became the guy with media relationships, innovating Republican messaging:

  "The way that Holmes always looked at it was like, okay, how do we make this interesting to the audience? Who are we talking to?" – Ashbrook on Holmes’ approach (10:03)

b) Josh Holmes

• Came to the Senate from a campaign background, prized for campaign acumen rather than "typical" legal or policy path.
• Innovated creative messaging (“Cornhusker Kickback” for Obamacare):

  "How about you just call it the Cornhusker Kickback?" – Holmes (14:11)

• Described the grind and impact of making Republican talking points mainstream:

  "There is no other reason why the vernacular of that era came to public consciousness other than John Ashbrook..." – Michael Duncan (12:28)

• Led efforts to recruit, message, and re-elect GOP Senators, notably contributing to the 2014 "comeback."
• Admitted to "faking it until you make it" early on, and drew parallels to learning sports from an ex-player:

  "What I love about watching NFL football is seeing Troy Aikman...he can provide you an analysis...that's instructive in a way that's different than a guy who does television." (47:25)

c) Michael Duncan

• Originated in digital campaigns, early Tea Party organizing, then transitioned to consulting:

  "My job was to make your jobs a living hell." – Duncan on his earlier role at FreedomWorks (23:04)

• Mastered online organization and digital advertising at a time when few understood it, earning trust by rejecting fundraising "scam PACS."
• Hailed for integrity and intellect:

  "If you're not providing the value that you said you were soliciting their money for, you're a crook." – Holmes (26:45)

• Collaborates deeply with the group, appreciated for both research skills and being a "human Google machine." (27:54)

d) Comfortably Smug

• Began at a hedge fund during the 2008 financial crisis, witnessing the chaos firsthand:

  "It's also insane to think...MDs going to ATMs and pulling cash and telling us that, like, well, we don't know if I'll be able to do that tomorrow." (29:59)

• Entered New York Republican politics afterward, running field/data operations for Manhattan GOP campaigns.
• Created and helms Comfortably Smug persona, blending finance, campaign, and Twitter mastery:

  "So few conservatives thought, hey, let's try to be funny about it. Even if it's gallows humor...you gotta find a way to laugh." (36:18)

• Built the Smug identity to anonymously comment without impacting finance career.
• Organized “off the record” operative and journalist happy hours, bringing together key new-media figures.

e) How Ruthless Came Together

• The crew gelled during regular campaign/consulting collaborations, then during COVID lockdowns via daily Zoom happy hours and shared online gambling (horseracing).
• Smug’s meme-savvy irreverence complemented Holmes/Ashbrook’s institutional knowledge and Duncan’s digital chops.
• The podcast was born from this chemistry and a sense of urgency to provide insider analysis with humor.

3. Holmes’ Mustache (The “Porn ‘Stache”)

Timestamps: 50:14–53:18

• The infamous mustache returns by listener demand:

  "He likes it when you bring it because it's just like, here there's DGAF Holmes. And like, we're gonna get some, like, double barrel takes." – Comfortably Smug (50:48)

• Holmes grows it partly to push boundaries with Fox and to annoy his wife, who “hates it”:

  "I just wanna see how far I can get away with something before somebody says something. And like, part of that is my wife, who fucking hates it." – Holmes (51:14)

• Movember attempts from the crew result in good-natured mockery—Ashbrook simply can’t grow one:

  "If I try to grow facial hair, it just doesn't work." – Ashbrook (53:07)

4. "Progrum" and Other Inside Jokes

Timestamps: 53:30–57:51

• The odd pronunciation “progrum” is rooted in regional dialects, college football vernacular (“it’s a good program”), and long-running inside jokes.
• It functions as a shibboleth:

  "When we go out and do shows and...they refer to it as a program, like, oh, you're an OG." – Smug (55:42)

• Watching old Senators with “genteel Southern aristocrat” accents was formative for their style.

5. Day Jobs vs. Full-time Pod

Timestamps: 59:17–60:49

• The team still has demanding “day jobs” in communications, digital, and strategy for political and business clients.
• The podcast remains a passion project and creative outlet:

  "What you hear every single time we do a show is exactly what we'd be talking about if we did not have microphones on." – Ashbrook (60:29)

Notable Quotes & Memorable Moments

• "I'll get the present, and then whatever the store bag it comes in, I leave it right next to the tree. If you look at it, it's on you." – Comfortably Smug (03:01)
• "You can't beat yourself up because you're starting on a low level. That's where everybody starts." – John Ashbrook (06:51)
• "Fake it till you make it." – Multiple hosts on early DC careers (09:09)
• "If you’re not providing the value that you said you were soliciting their money for, you’re a crook." – Holmes on PACs (26:45)
• "I just wanna see how far I can get away with something before somebody says something. And like, part of that is my wife, who fucking hates it." – Holmes on the mustache (51:14)
• "What you hear every single time we do a show is exactly what we'd be talking about if we did not have microphones on." – Ashbrook (60:29)

Timestamps for Major Segments

• Gift-wrapping/Christmas banter: 02:22–04:15
• Q&A: Bios and origin stories: 04:38–28:36
• Smug’s background, financial crisis, campaign/consultant crossroads: 29:02–36:38
• Comfortably Smug Twitter phenomenon and Ruthless origin: 36:38–40:30
• Holmes’ campaign/senate origin: 41:25–47:25
• Holmes' mustache lore: 50:14–53:18
• Progrum/inside language: 53:30–57:51
• Pod vs. Day jobs: 59:17–60:49

Tone & Takeaway

The episode is a masterclass in blending inside political knowledge with broad-appeal humor. The fellows are unapologetically themselves, self-deprecating, insightful, and willing to lift the curtain for listeners (“minions”). They provide the backgrounds that inform their takes with humility and zero pretense, making this Christmas Q&A a quintessential Ruthless experience.

If you want to know why Ruthless feels different—why its humor hits, its analysis resonates, and the guys seem to “know stuff nobody else does”—this is the foundational episode.

End of Summary