The Firm Behind the Show: Ruthless, Cavalry, and How a ...

Most of the fortunes in this series are old, and their structures are public because size eventually forces disclosure. Here is a smaller, newer, and more ordinary case that is useful precisely because it shows where the public record stops. The people behind the conservative podcast Ruthless run two closely held private companies, a political consulting firm and a media entity, and their wealth, to the extent it exists, sits inside those companies. Because one of those companies is paid by political campaigns, campaign-finance law pries open a narrow window most private firms never have. Read carefully, that window shows a lot of money moving and tells you almost nothing about how much anyone keeps. This is a study in what is knowable, handled neutrally and from the record. It takes no political side.

The podcast

Ruthless launched in October 2020, just before that year's presidential election, and brands itself, with a deliberate misspelling, as "a variety progrum" (Axios; Ruthless Podcast). It is widely described as a conservative counterpart to the progressive show Pod Save America, mixing news analysis with comedy and interviews, and it publishes three episodes a week distributed across Apple, Spotify, YouTube, and other platforms (OutKick; Fox News). The only circulating audience figure is a self-reported "average of around 5 million unique listeners," which is not independently audited, so it is best treated as the show's own claim rather than a verified number (Cavalry LLC).

The business model is a familiar podcast mix: merchandise, advertising sold through a marketplace, and ticketed live shows, including one at Washington's Anthem in 2022 and broadcasts from the 2024 Republican National Convention (OutKick). The most significant business event came on July 15, 2025, when Fox News Media announced a licensing deal that placed Ruthless in a new-media division and made the four hosts Fox News contributors. The financial terms were not disclosed (Fox News press release; Axios).

The hosts

The show has four hosts, and three of them are principals of the same firm. Josh Holmes was chief of staff to Senate Republican leader Mitch McConnell from 2010 to 2013, then ran McConnell's 2014 reelection campaign, and in 2015 co-founded the Republican consulting firm Cavalry LLC, where he is president (PolitiFact; Roll Call; LegiStorm). Michael Duncan, a digital strategist, and John Ashbrook, a communications specialist whose most recent Capitol Hill role was staff director of the Senate Republican Communications Center, are the other two founding Cavalry partners (Cavalry LLC; LegiStorm). A few widely repeated details do not hold up: this Michael Duncan is not the former Republican National Committee chairman of the same surname, and no journalism role appears in Ashbrook's documented record, which is Senate Republican communications and campaigns throughout.

The fourth host uses the pseudonym "Comfortably Smug," and here the record requires care. Fox News's own July 2025 press release, a primary source distributed by the show's business partner, publicly names him: the program is co-hosted by Holmes, Duncan, and Ashbrook "as well as Shashank Tripathi, pseudonymously known as 'Comfortably Smug'" (Fox News press release). He is described as having a finance background and guards his appearance in public. That same persona was at the center of a documented 2012 episode: during Hurricane Sandy, the @ComfortablySmug account posted false claims, including that the New York Stock Exchange floor had flooded, after which the account holder was identified as Tripathi and resigned as a Republican congressional candidate's campaign manager, and apologized (BuzzFeed News; Poynter). The link between today's host and that 2012 account rests on a continuous persona and the name his own business partner now states officially, not on a personal admission; the host has neither confirmed nor denied it. That is the honest level of certainty, and it is worth stating plainly rather than either asserting or hiding.

The money, and the limits of what it shows

The wealth question here has an unusually bright partial answer and a genuinely dark remainder. Cavalry LLC is a privately held consulting firm that files no public financial statements, so on its own it would be a closed book (Cavalry LLC). But because it is paid by political campaigns and committees, and because those committees must itemize their spending to the Federal Election Commission, the firm's revenue leaves a public trail almost no private business has. Aggregated, the committees paying Cavalry disbursed roughly $36 million in the 2020 cycle, $13 million in 2022, and $12 million in 2024, concentrated among McConnell-aligned committees and the Senate Republican campaign arm (OpenSecrets).

Those numbers look enormous, and this is the single most important thing to understand about them: they are money routed through the firm, not money the firm keeps. The largest individual line items are media buys, digital advertising and list rentals, that the firm places on a campaign's behalf and largely passes through to ad platforms and vendors (FEC records). Because a vendor does not have to disclose what it pays its own subcontractors, the public figure overstates the firm's actual earnings, a well-documented pattern for digital political firms (OpenSecrets). The podcast itself sits in a separate company, Bobcat Media LLC, which has no campaign-finance records at all, meaning its advertising, merchandise, and Fox licensing revenue are entirely private (FEC records).

And the personal question, what any of the four hosts is individually worth, what they invest in, what boards they sit on, has a clean and defensible answer: it is not in the public record. None of them is a federal candidate, officeholder, or senior appointee, so none is required to file a personal financial disclosure, and absent that filing the information simply does not exist publicly. The only documented ventures are the two firms themselves. Where their personal balance sheets are concerned, the correct statement is that they are not publicly documented, and this piece does not estimate them.

How the Fox deal works, and how the two sides fit together

The July 2025 licensing deal is worth reading closely, because its structure explains what changed and what did not. It placed Ruthless inside a newly created Fox News Media division called New Media, led by Fox News Digital president and editor-in-chief Porter Berry, who kept his existing digital role and reports to chief executive Suzanne Scott and executive editor Jay Wallace (Fox News press release). Trade outlets described it as the first time Fox News had licensed a podcast, a "first" that comes from the trade coverage rather than from Fox's own wording (Barrett Media).

The key structural fact is that this is a licensing deal, not an acquisition. Fox distributes and brands the show inside its New Media portfolio, alongside programs like Will Cain Country, but the hosts keep their own company and the podcast continues to be published by Bobcat Media LLC (Variety; The Desk). What each side gets is fairly legible. Fox gets a young male audience it has trouble reaching on cable, citing its own commissioned polling from National Research, Inc. that called Ruthless a top news source among men ages 18 to 45, a figure that appears only in Fox's announcement and rests on an unpublished poll, so it is best read as Fox's framing rather than an audited number. Fox also gets four new contributors and content for its podcast division, and Scott called the show "a natural extension of our powerhouse brand" (Barrett Media). The hosts get Fox's promotional reach and an undisclosed licensing arrangement layered on top of their existing revenue, while keeping their independence.

The two work together mostly through cross-promotion, and it runs both directions. The hosts appear on Fox programs, for instance unpacking the Sydney Sweeney American Eagle advertisement on The Will Cain Show, and Fox maintains a dedicated Ruthless show hub that pushes episodes and clips (Fox News Radio; Fox News show hub). It is worth being precise about what that promotion is and is not. No discrete paid television commercial promoting Ruthless could be found. The documented promotion is on-air appearances, a dedicated Fox web hub, and cross-posted clips, not a standalone ad buy, and the terms of the deal, including whether the licensing arrangement even involves a cash fee to the hosts as opposed to distribution and promotion in kind, were never disclosed (Axios). So the honest description is a promotional and distribution partnership of undisclosed value, not a measured advertising campaign.

Where the podcast money comes from, on channel and off

The podcast's own revenue sits inside Bobcat Media LLC, a private company with no campaign-finance trail, so the amounts are not public. The sources, though, are visible, and they split cleanly into on-channel platform income and off-channel events and deals.

On channel, the core is advertising against distribution. Ruthless publishes about twice a week on YouTube and more than thirty audio platforms, and it sells ads in two forms: host-read "baked-in" direct-response spots and dynamically inserted ads, placed through Libsyn's AdvertiseCast marketplace, with the show represented by the Baltimore ad agency Club Road Associates (Podwires; Podnews). The show has moved its hosting from Simplecast to Libsyn to Megaphone by mid-2025, an enterprise platform built for dynamic ad insertion and third-party measurement through Podsights, Podtrac, and Nielsen; the timing lines up with the Fox deal, though the two are not explicitly linked (Podnews). YouTube advertising and any channel memberships add to the on-channel mix, though those amounts are not disclosed either.

Off channel, the money comes from events, merchandise, and now Fox. Ruthless has produced live ticketed shows, including a "Variety Progrum" performance at Washington's Anthem in February 2022 with tickets around 20 dollars, although attendance and gross were never released (Ticketmaster). It has run on-location, self-described "NFL-style" broadcasts from party conventions, including the 2024 Republican National Convention in Milwaukee (Apple Podcasts). It sells branded apparel and accessories through an official store (Ruthless store). And the undisclosed Fox licensing arrangement now sits on top of all of it.

The honest bottom line matches the rest of this piece: the sources of the money are visible, the size of it is not. Ad rates, YouTube income, merch sales, ticket grosses, and the Fox terms are all private, the show's own "roughly 5 million unique listeners" is a self-reported figure rather than an audited measurement (Rephonic), and no public Patreon or premium subscription tier is documented. A political podcast's income map is easy to sketch and, in a privately held company, nearly impossible to price.

How it fits the series

Set against the dynasties elsewhere in this series, the Ruthless team is a useful small case because it shows the default state of private wealth, the state that trusts and holding companies and foundations are all built to preserve. The wealth vehicle here is exactly what those larger families formalize: equity in closely held private companies, plus the cash those companies throw off, opaque by default. A consulting firm and a media company owned by a handful of partners is, structurally, the same kind of object as a private law firm, an advertising agency, or a family media business, its value sitting in the company and its relationships rather than in disclosed securities.

The one twist is the campaign-finance window, and it is worth appreciating exactly what it does and does not reveal. Political-vendor status pierces part of the normal opacity of a private firm, forcing disclosure of who paid, when, and for what stated purpose. That is far more than most private businesses ever reveal. But it stops at the top line. It shows the dollars moving through the door and never the profit, the margins, the ownership splits, or the partners' draws. It is a reminder that even the brightest public window on private money usually illuminates the flow and leaves the fortune itself in shadow, which is precisely why the families who most want to preserve wealth build the structures that keep it there.

Fact-check notes and sources

The podcast (Ruthless launching in October 2020 and branding itself a "variety progrum," its description as a conservative counterpart to Pod Save America, its three-a-week cadence and multi-platform distribution, the self-reported roughly 5 million unique-listener figure, the business model of merchandise, advertising, and live shows, and the July 15, 2025 Fox News licensing deal that made the hosts Fox contributors on undisclosed terms): Axios, Ruthless Podcast, OutKick, Fox News, Cavalry LLC, and Fox News press release. The exact launch day differs across sources (October 9 versus October 22, 2020), so only "October 2020" is asserted; the listener figure is self-reported and not independently audited.
The hosts (Josh Holmes as McConnell's former chief of staff and 2014 campaign leader and a Cavalry founder and president; Michael Duncan and John Ashbrook as the other founding Cavalry partners; and the pseudonymous fourth host): PolitiFact, Roll Call, LegiStorm on Holmes, Cavalry LLC on Ashbrook, and LegiStorm on Ashbrook. Several commonly repeated claims are not supported and are avoided here: this Michael Duncan is not the former RNC chairman of the same surname, no journalism role is documented for Ashbrook, and Holmes's 2014 NRSC role was senior advisor rather than executive director.
The pseudonymous host (Fox News's July 2025 press release publicly naming the fourth host as Shashank Tripathi, known as "Comfortably Smug," and the documented 2012 Hurricane Sandy episode tied to that persona): Fox News press release, BuzzFeed News, and Poynter. The name is on the public record via a primary source; the tie between today's host and the 2012 account rests on persona continuity and that official naming, not on a personal admission, and the host has neither confirmed nor denied it.
The money (Cavalry LLC as a private consulting firm; the roughly $36 million, $13 million, and $12 million in committee disbursements routed through it in the 2020, 2022, and 2024 cycles; the crucial caveat that these gross totals are largely pass-through media buys rather than firm profit; the separate Bobcat Media LLC producing the podcast with no campaign-finance records; and the absence of any public documentation of the hosts' personal net worth, investments, or board seats): Cavalry LLC, OpenSecrets vendor data, FEC Schedule B records, and OpenSecrets on political ad-buying. The gross FEC totals overstate the firm's earnings because vendors need not disclose payments to their own subcontractors; the personal financial information does not exist in the public record because none of the four is required to file a disclosure.
The Fox deal mechanics (the July 15, 2025 licensing deal placing Ruthless in a new Fox News Media "New Media" division led by Porter Berry under CEO Suzanne Scott and executive editor Jay Wallace; the four hosts as Fox contributors; the structure as a licensing deal rather than an acquisition with the show still published by Bobcat Media LLC; Fox's own National Research, Inc. "men 18 to 45" framing; the Scott "natural extension" quote; and undisclosed terms): the Fox News press release, Barrett Media, Variety, The Desk, and Axios. The "first podcast Fox has licensed" characterization comes from trade coverage, not Fox's own wording. No paid television commercial promoting Ruthless was located; documented promotion is on-air appearances and a dedicated Fox show hub, and the polling figure rests on an unpublished poll cited in Fox's own announcement.
The podcast income map (twice-weekly distribution on YouTube and 30-plus audio platforms; host-read baked-in plus dynamically inserted advertising sold through Libsyn's AdvertiseCast marketplace with the agency Club Road Associates; the Simplecast-to-Libsyn-to-Megaphone hosting migration with Podsights, Podtrac, and Nielsen measurement; the February 2022 Anthem live show at roughly 20 dollars; the 2024 RNC on-location coverage; the merchandise store; and the self-reported, unaudited "roughly 5 million unique listeners"): Podwires, Podnews, Ticketmaster, Apple Podcasts, the official store, and Rephonic. All revenue amounts are undisclosed because the podcast is held in the private Bobcat Media LLC; the listener figure is the show's own promotional claim, not an audited measurement.

This post is informational and neutral, not financial or political advocacy. Figures are reproduced from the cited public records, campaign-finance data, and reporting, with self-reported, single-source, and undisclosed items flagged as such. Individuals and companies are discussed as nominative fair use from the public record, with no affiliation implied.

The Firm Behind the Show: Ruthless, Cavalry, and How a Political Podcast's Money Works