👋 Good Morning. Can’t believe we’re halfway through January already?! Welcome to the 3rd edition of our Weekly Recap. The news, trends, and training Producers need (with less of the boring).

😨Vibe Check: Two tech bros raised $42M calling you "deceptive," carriers are calculating how to automate 21% of your job, and GLP-1’s might be setting off ADA lawsuits very soon.

☕ Grab your coffee, stop scrolling IG for motivational quotes that won't write business, and let's get into it.

STORY OF THE WEEK

WithCoverage Raises $42M to “Fix” Traditional Broker Model with AI

Two tech bros just raised $42 million to "replace traditional insurance brokers."

And they're already winning. WithCoverage, an insurtech startup founded by JD Ross (Opendoor co-founder) and Max Brenner (scaled Compound to $1B+), closed a Series B round this week led by Sequoia and Khosla Ventures.

Their pitch: Your commission-based model is "deceptive" and "misaligned," and they're going to fix it with AI and a flat fee.

The playbook sounds familiar: Start with an AI-powered policy audit that finds coverage gaps and overpaying (shocker: they always find both). Pair it with in-house insurance experts and attorneys. Run competitive carrier shopping. Charge a flat fee instead of commission. Watch clients save "$100K+ per year."

They've already converted 700+ companies in 18 months, including GoPuff, Eight Sleep, and Blank Street. And they're profitable.

Here's what they're actually saying about you: CEO Max Brenner calls the industry "regulated and deceptive." Co-founder Ross says brokers get paid more when clients pay more, creating an inherent conflict. Sequoia's Roelof Botha says the industry has "prioritized carrier relationships over the needs of insured businesses." Ouch.

Why this actually matters (beyond the trash talk): WithCoverage isn't targeting your book of 47 auto body shops in Ohio (yet). They're laser-focused on fast-growing, venture-backed companies to start, because these clients are already skeptical of commission structures, they're used to SaaS pricing, and they'd rather text a claims attorney than play phone tag with their broker who's on the golf course.

The uncomfortable truth: They're exploiting real pain points. Opaque pricing. Email-and-spreadsheet workflows. Brokers who disappear after renewal. Coverage gaps that only surface during claims.

They don't need to replace ALL brokers to start. They just need to replace enough of them to get traction. Then it’s on to the mid market.

WithCoverage is essentially calling out the entire industry's worst actors and promising to be everything traditional brokers aren't—responsive, transparent, tech-enabled, and aligned with client outcomes.

If that pitch is resonating with 700 companies in 18 months, and raising $42 million in capital, this ain’t your daddy’s insuretech wrapper. It’s the real deal.

Sleep tight.

NEWS OF THE WEEK

💊Mark Cuban Wants to Blow Up The Healthcare System (Again)

The rant: Maverick billionaire Mark Cuban reignited his healthcare crusade on X Saturday, asking “why insurance companies pay $2,500 for an MRI when there's a center down the street that'll do it for $350?”

The target: He's pointing fingers at the cozy relationship between hospitals and insurers who inflate prices through backroom negotiations, then pass the bill to employers through skyrocketing premiums.

His solution: Cut out the middleman entirely with transparent pricing like his Cost Plus Drug Company model.

Here's the rub: Your clients are reading these headlines and wondering if their plan is actually a good deal or just an expensive handshake agreement between insurance companies and healthcare systems. If you're not proactively showing clients how to lower costs, your competitors will steal your lunch money with alternative solutions.

💉GLP-1 Drugs Just Became Your Next ADA Nightmare

The setup: The EEOC quietly decided in 2023 that obesity counts as a disability under the ADA, and now in 2026 your clients who've been blanket-excluding expensive GLP-1 drugs (Ozempic, Wegovy, Mounjaro) from their health plans are potentially sitting on discrimination lawsuits waiting to happen.

The problem: The "safe harbor" that used to protect benefit plans from ADA claims is shrinking fast. Saying "we don't cover that" based on the condition itself instead of actual medical necessity is looking legally dicey.

It gets messier: Ro (the telehealth darling) just partnered with Amgen to study why patients can't actually ACCESS these drugs even when they're technically covered. Prior authorizations, step therapy hoops, and coverage denials are so brutal that people are running to compounding pharmacies and sketchy online sources instead.

If you're not having these conversations with your group health clients, get on it ASAP.

🤖Carriers Just Figured Out How to Print Money with Robots

The numbers: Two reports dropped last week showing carrier expenses are tanking and AI is the reason. AM Best says expense ratios already fell 2.4 points over the last decade, while Morgan Stanley projects another 2-point drop by 2030 that could pump $9.3 billion straight into carrier operating income.

The breakdown: Remote work killed rent expenses, but AI is the real story. Morgan Stanley analyzed 16 major carriers using Anthropic's data to figure out which jobs get automated:

• Specialty insurers can automate 25%

• Standard carriers hit 20%

• Insurance agents get 21%

Study says carriers spend $3 billion implementing AI in 2026 while only seeing $600 million in savings. But by 2030, all systems go with 100% of savings hitting the books.

Something to keep an eye on: If underwriters are AI-assisted, service teams are AI-powered, and claims are automated, why share 12-15% with retail agents when they can go direct? Think Progressive in commercial auto. It's not as far-fetched as you think.

👻Supreme Court Ghosts on Trump's Tariff Case

What happened: The Supreme Court issued three decisions Wednesday but ghosted on the big one, Trump's global tariffs case that's got the entire business world holding its breath.

The background: Trump rolled back into office in January 2025 and immediately slapped tariffs on imports by invoking a 1977 "national emergency" law meant for actual emergencies (think wars and terrorist attacks), not trade tiffs. Lower courts called BS. Now SCOTUS is weighing whether presidents can basically rewrite trade policy solo by claiming everything's an emergency. Even the conservative justices seemed skeptical during November arguments.

Why you should care: Your manufacturing, distribution, and retail clients are either drowning in higher costs or about to be. That means replacement values are climbing, business interruption exposures are multiplying, premiums are going up, and carriers are getting twitchy with underwriting.

NUMBER OF THE WEEK

💸$556M

The settlement amount Kaiser Permanente just got slapped with for allegedly gaming Medicare Advantage through aggressive diagnosis coding. Two whistleblowers, former Kaiser employees, are splitting $95 million from the deal.

The scheme: Kaiser executives allegedly pressured doctors to add thousands of diagnoses weeks or even months after patients had been treated. They'd have doctors sit together at lunch or after work, with food and drinks provided by Kaiser, to code their visits with additional diagnoses. The DOJ claims Kaiser received $1 billion from 2009 to 2018 from these additional diagnoses.

The kicker: Five of the 10 largest insurers in the Medicare Advantage market have either settled a federal civil fraud suit or currently face one. This isn't an outlier, it's the industry standard getting caught.

PRODUCER OF THE WEEK

Tony Brunini

In this episode, Trey talks with Top Producer, Tony Brunini. Tony Brunini didn't get into insurance until he was 40. Now he writes $750K+ a year specializing in a unique RE vertical.

TOOLS OF THE WEEK

📈 Insurance Xdate: free trial here

📬 Max Revenue Letter: sign up here⁠⁠⁠⁠⁠⁠⁠

📒 Producer Playbook: learn more here

⁠⁠⁠⁠🕹️ Play Producer Games: check it out here

POD OF THE WEEK

Rules For Thee, Not For Me: The Hypocrisy of the Howden and Brown & Brown Debacle w/ Brandon Schuh

In this episode, Trey and Micah talk with Brandon Schuh, a multi-million dollar producer in the product liability space.

Brandon shares his unique insight into the Howden vs. Brown & Brown drama as an ex-Hays Cos producer, and it's implications for brokerage valuations, and the future of non-solicit agreements in the commercial insurance industry.

The conversation also covers the importance of building relationships, the challenges faced by new producers, and the structure of successful teams.

POLL OF THE WEEK

OPINION

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That’s this week in insurance.

Forward it to your buddy who just got rolled and needs a pick-me-up.

See you next week.