Nathen, Mark & the “Deserve to Win” Circus

Nathen, Mark & the “Deserve to Win” Circus

Not many discussions capture the hostility around serial TCPA litigation the way Episode 44 of the Deserve to Win podcast does. Hosted by TCPA attorney Eric J. Troutman, the episode goes straight after two names that regularly come up in TCPA circles: Nathen Barton and Mark Dembroski.

Neither one gets an easy ride. Dembroski shows up early, tied to a fight against WinRed. Barton takes over later, when Troutman walks through Barton’s jury-trial win and stacks it against a separate case that dragged on for years.

What comes out of it is a blunt, occasionally harsh window into how a chunk of the TCPA defense bar sees aggressive consumer litigation — especially once a case turns into a long, costly slog through the courts.

Before going further, it’s worth pulling the podcast’s commentary apart from actual judicial findings. Plenty of what Troutman says is straight opinion, joking, or outright mockery. The litigation outcomes underneath, though, can be checked against the court record — and this piece does that wherever possible.

The Podcast Sets Its Sights on Dembroski

Roughly two minutes in, Troutman kicks off a segment on WinRed’s win over Mark Dembroski, and he doesn’t bother hiding his tone. He jokes about how Dembroski will take being talked about, riffs on his name, and calls him the “sheriff” — a nickname that apparently comes from Dembroski himself.

Then the hosts get down to business: per the podcast, Dembroski said he’d received around 80 messages, while WinRed put the figure closer to 30. That gap in numbers wasn’t what settled things, though. The real fight was over whether the evidence actually connected WinRed to sending those messages in the first place.

Why WinRed Won

The messages reportedly included the line “powered by WinRed.” To a plaintiff, that phrase might look like an open-and-shut connection — but the legal question was narrower than that. Did “powered by” WinRed actually mean WinRed sent the texts?

Troutman says WinRed moved for summary judgment on that exact point, arguing that having its name on a message wasn’t proof it sent the message. According to the podcast, the court agreed, finding no evidence that WinRed was the platform that actually pushed the texts out.

That distinction reaches well past this one case. In TCPA litigation, someone can receive an unwanted text and still hit a wall trying to figure out who’s legally on the hook for it — branding, backend software, payment processing, and campaign vendors can all be separate entities. The WinRed piece is a good example of a problem that keeps coming up in this corner of the law: pinning down the right defendant can be just as tough as proving the contact happened at all.

The Podcast’s Mockery of Dembroski’s Deposition

Things get more personal when Troutman brings up that Dembroski deposed WinRed’s CEO. He reacts with over-the-top humor, guessing at how Dembroski behaved during the deposition and joking about wanting to watch the tape.

That’s commentary, not a court ruling, and there’s no point pretending otherwise. But it shows how far the episode is willing to go. Instead of keeping things at arm’s length as a legal dispute, Troutman and his co-hosts turn it into running commentary on the people themselves — which says something about the culture surrounding serial TCPA litigation more broadly.

Then Comes Nathen Barton!!!

If the Dembroski bit sets the mood, the later stretch on Nathen Barton is where things get more substantive. Around minute 24, Troutman mentions that the previous episode’s coverage of Barton’s jury win drove a spike in views — and jokes that Barton and his friends are probably watching this one too.

Barton isn’t just a passing mention here. His litigation history becomes the yardstick Troutman uses to explain what a real courtroom win actually looks like.

Barton’s $73,000 Jury-Trial Victory

What makes Troutman’s take on Barton notable is that he doesn’t brush the result aside. He starts with Edwards v. Tamez, a separate TCPA case that reportedly stretched on for about five years over four allegedly unwanted calls. Per the podcast, the federal court found Do Not Call violations and handed down just $1,000, along with a Nevada recording claim that produced nothing.

Then he circles back to Barton, plainly: Barton took his case to a jury and, according to the podcast, came away with $73,000. Troutman calls it “an actual win.”

That’s a real acknowledgment. Whatever anyone thinks of Barton, a jury verdict with a sizable award is a different beast than a filed complaint, a quiet settlement, or years spent chasing a token payout — and Troutman makes that distinction himself.

The Barton Comparison Becomes a Critique of Litigation Strategy

Troutman doesn’t just stop at the numbers. He uses the five-year Edwards case to question whether stretching litigation out for a small recovery ever makes sense — pointing to the toll on court resources, taxpayer money, and the litigants’ own time. He calls that kind of drawn-out fight a “pissing match” and flatly labels it bad strategy.

That’s why Barton takes up so much space in the episode. Troutman isn’t saying every TCPA plaintiff is illegitimate — he’s drawing a line between litigation that produces something real and litigation that eats up huge resources for a small payoff. Barton is his example of the first. Edwards is his example of the second.

Why Barton Remains a Lightning Rod in TCPA Circles

Barton’s litigation footprint is substantial. Public federal dockets show several TCPA cases filed by Nathen W. Barton in the Western District of Washington and beyond. One example: Barton v. Delfgauw et al., Case No. 3:21-cv-05610, filed in 2021 as a TCPA action with a jury demand — a case that turned highly contentious as it wore on. A 2025 order in that matter pointed to years of “twists and turns,” covering discovery disputes, sanctions issues, and dueling claims about how the parties behaved.

That matters because the controversy around Barton isn’t just podcast talk — it shows up in the docket itself. Still, contentious litigation doesn’t mean every accusation against Barton has been proven in court; the record deserves a careful read, and claims from either side shouldn’t be treated as settled.

Barton Has Also Won Other TCPA Relief

The full picture is messier than “plaintiff who keeps losing.” In a separate case, the Ninth Circuit weighed in on Barton’s TCPA claims over calls made to a phone registered to his minor child; the appellate record shows Barton landed a $12,000 default judgment after the defendant never showed up to fight it. More recently, in Barton v. George, a federal court first turned down Barton’s default judgment request for failing to pin down qualifying calls — then later granted it in part, awarding Barton $23,500 in statutory damages from AG Marketing.

Those results complicate any tidy narrative. Barton has racked up losses, procedural stumbles, contentious fights, and plenty of ridicule — but he’s also come away with real money judgments. That’s exactly why Troutman’s “actual win” line carries some weight.

Reputation Is Not the Same as a Ruling

One recurring issue in coverage of serial TCPA plaintiffs is mashing three separate things into one:

What the plaintiff claims What opposing counsel says about the plaintiff What a court actually decides

A lawyer can rip into a plaintiff on a podcast without that turning into a judicial finding. A defendant can accuse a plaintiff of gaming the system without any court ever backing that up. And a plaintiff can have a long litigation history without every single case being weak. Both Barton and Dembroski fall under that same logic here.

The Deserve to Win podcast is a useful window into how one slice of the TCPA defense bar views these litigants — but it isn’t, on its own, proof of every claim made on the show.

Two Different Stories

The contrast between the two men is the most interesting thread in the episode. Dembroski’s segment centers on a case where, per the podcast, the court found the evidence lacking that WinRed itself sent the disputed messages — a defense win. Barton’s segment centers on a jury outcome that Troutman himself calls a genuine $73,000 win.

Dembroski: a plaintiff whose WinRed claim gets framed as a loss. Barton: a plaintiff whose jury result even his critic calls a real win.

That contrast tells you more than just slapping “winner” or “loser” on either man.

What Does It Mean to “Deserve to Win”?

There’s a bit of irony baked into the show’s title. The closing segment asks what it actually takes to “deserve to win,” and the answers land on preparation, accountability, knowing the rules, and following through consistently.

That framing fits both segments neatly. TCPA litigation runs on technical statutory requirements, evidence rules, procedural deadlines, discovery obligations — and, as the WinRed case shows, the question of who actually caused a message to be sent. Winning isn’t just about getting an unwanted call or text; it’s about proving every required element against the correct defendant and making it through the procedural gauntlet that follows.

Why the Podcast Matters

The real significance of Episode 44 isn’t that a podcast host cracked jokes at two litigants’ expense. It’s that the episode lays bare the increasingly adversarial culture around TCPA litigation and repeat plaintiffs. Troutman’s commentary shows how defense-side attorneys view litigants who keep filing claims, pushing discovery, taking depositions, and demanding jury trials.

The humor is sharp, sometimes deliberately so. But there’s a real debate sitting underneath it: When does aggressive enforcement actually serve the statute’s purpose? When does litigation get disproportionately expensive? When does winning a judgment prove a claim had real merit — and when does a case turn into more of a fight than a violation? Those are fair questions no matter which side of the TCPA debate someone lands on.

The Reality Behind the Ridicule

The lazy way to cover this episode would be to just repeat the jokes and call it a personal takedown. That skips the more interesting story.

Mark Dembroski drew sharp ridicule after a WinRed loss that, according to the episode, came down to whether WinRed could be tied to sending the disputed messages at all.

Nathen Barton drew repeated attention after a jury trial that Troutman himself calls a real win worth about $73,000 — even as Barton’s broader litigation record includes both genuine judgments and real procedural setbacks.

This isn’t a clean hero-versus-villain story. It’s a snapshot of a messy legal landscape where plaintiffs, defense attorneys, tech vendors, political organizations, and courts keep colliding over where the TCPA’s lines actually sit — and Deserve to Win offers an unusually raw look at that fight.

Final Takeaway

Episode 44 stands out because it puts Nathen Barton and Mark Dembroski side by side while showing two very different results. Dembroski gets mocked throughout the WinRed segment, especially once the ruling comes down in WinRed’s favor. Barton takes his own share of criticism and ridicule elsewhere, but Troutman openly credits Barton’s $73,000 jury-trial win as legitimate.

That distinction shouldn’t get lost in the noise. The podcast is opinionated, sarcastic, and at times deliberately combative. But underneath the trash talk are real questions about litigation strategy, evidence, judicial resources, and what actually counts as a meaningful TCPA win.

For anyone tracking Nathen Barton, Mark Dembroski, TCPA litigation, serial plaintiffs, and the growing tension between consumer litigants and the TCPA defense bar, this episode offers a direct, unpolished look at that fight. Maybe the simplest lesson is the truest one: in TCPA litigation, the courtroom record still matters more than the trash talk — which is exactly why the Barton and Dembroski stories are worth digging into.

Sources

Deserve to Win, Episode 44: Podcast transcript covering the discussion of Mark Dembroski, WinRed, Nathen Barton, Barton’s jury-trial result, and the comparison with Edwards v. Tamez.

Barton v. Delfgauw et al., No. 3:21-cv-05610: Federal docket and subsequent court orders concerning Barton’s TCPA litigation.

Barton v. Delfgauw, 2025 federal court orders: Rulings on discovery, sanctions-related disputes, and litigation conduct.

Barton v. George et al., No. C25-5110-KKE: Federal court orders on Barton’s TCPA claims and statutory damages.

Ninth Circuit Barton decision: Appellate record on Barton’s TCPA claims and $12,000 default judgment.

Disclaimer

This article is intended for informational and commentary purposes only. It discusses publicly available court records and statements contained in the Deserve to Win podcast transcript supplied for review.

Statements attributed to podcast participants are presented as their statements, opinions, characterizations, or commentary and should not be treated as established facts. Allegations in complaints, motions, briefs, or other adversarial filings are not judicial findings.

Where a court has entered a judgment or order, the article describes that ruling based on the available record. The existence of litigation, a dismissal, a judgment, a settlement, or an adverse ruling should not, by itself, be read as proof that every allegation made by either side was true or false.

Nothing in this article should be construed as a determination that any individual engaged in unlawful conduct unless such a determination has been made by a competent court or is otherwise supported by reliable evidence.