Tim Wulff

[Tim Wulff @timwulff]

The AI trade is shifting from "who has the best model" to "who owns the learning loop."

$PLTR proved it for B2B. $LMND is doing it for insurance.

Every claim and data trace compounds their “Token Capital.” Legacy giants can't catch a flywheel born in code.

[Satya Nadella @satyanadella]

https://t.co/vLmiBKTtX3

[Tim Wulff @timwulff]

@shai_wininger Hope to be there

[Tim Wulff @timwulff]

@Neil_X10 @outlierrcapital I'm not seeing it available to watch now. Anyone have a copy or link? @TempusAI

[Eric Bryant | Multibagger Research @MultibaggerRsch]

"Isn't $LMND just another insurtech?"

This chart can lay that argument to rest.

Customers per employee, 2020–2025:
$LMND vs. $ROOT vs. 7 major incumbents.

$ROOT is the perfect test case. Same era. Same "insurtech" label. Same direct-to-consumer P&C model. Public company with clean data.

$ROOT at 457 customers per employee.

GEICO at 568.

Progressive at 514.

Root IS the incumbent band.

Why? $ROOT innovation was telematics — better pricing through driving data. That helped them reach profitability. But it didn't change how many humans they need to operate.

Root hired 341 people last year to add 73K policies. $LMND hired 47 to add 570K.

That's not a difference of degree. It's a difference of kind.

$LMND didn't just digitize the front end. AI Maya underwrites. AI Jim handles claims. The marginal customer costs almost nothing to serve.

$ROOT used tech to price better. $LMND used AI to run the company.

That's why one curve compounds and the other flatlines.

This also kills the bear argument that competitors will "just copy $LMND playbook."

$ROOT has been trying for 9 years. Backed by $1.2B+ in funding. Public since 2020. Building technology from scratch with no legacy constraints.

And they still ended up in the incumbent band.

If a well-funded, tech-native insurtech with zero legacy baggage can't replicate this efficiency curve, what makes anyone think State Farm or Allstate will?

$LMND AI-first architecture isn't a feature. It's a compound advantage that gets harder to replicate every quarter — because every new customer, claim, and interaction feeds the models that make the next one cheaper to serve.

The moat isn’t JUST the AI operating system running the company. It’s 3 million customers (and growing) training the AI.

[Tim Wulff @timwulff]

@Ironic_Ape @longoption This

[Tim Wulff @timwulff]

@ShadyJosh5 @AndersReiche @Neil_X10 @jakebrowatzke I've used thumbtack before. Not sure there's much of a moat in the space

[Tim Wulff @timwulff]

@bjmtweets Ah you're right there is exclusivity

[Tim Wulff @timwulff]

@bjmtweets Carvana has no loyalty to Root. Carvana will drive margin to near zero and partner with whoever will profit share the most

[Tim Wulff @timwulff]

@Nick_Lamparelli Seems like a great way to get customers and this is how LMND is doing it with Chewy or Root is doing it with car. There is limited growth rate since most landlords are have <10 doors and just use Zillow or PDFs for signing lease

[Tim Wulff @timwulff]

Huge shout @MotleyFoolMoney for introducing me to the company in late 2020. And my fellow canadian engineer @PaperBagInvest and his spreadsheets for educating me on the business. I never buy at an IPO and felt like a discount at $88.22.

[Tim Wulff @timwulff]

The $PLTR of insurance is born. Listen to this pod.

Nice Technologies, is a new actuarial modeling company that aims to modernize risk management for insurance companies. From hours on Excel spreadsheets to Python doing the heavy lifting for Actuarials

https://t.co/lAzUUWbhIc

[Tim Wulff @timwulff]

Ads

[Jake Browatzke 🚀 @jakebrowatzke]

I talk about $LMND's AI ontology and automation a lot, and for good reason. But @Lemonade_Inc's in-house marketing team may be the most underrated moat in their business.

As someone who has spent hundreds of thousands of dollars per month on Meta ads for my own business, and who grew a YouTube channel to 800k+ subscribers making ad compilations (Jake's Top 10, feel free to look it up), I find marketing fun. And I have some weight when I say that Lemonade's social media marketing is impressive.

Organic stuff like what I'm sharing kills on Instagram and Facebook with my younger generation (under 35s), yet companies like GEICO and Progressive are not running a single organic-feeling ad like many of Lemonade's top performers. Those I'm sharing are the tip of the iceberg, with 250+ active Meta ads Lemonade is running currently—from personal testimonies, to image retargeting, to a few super high-quality produced ads like GEICO runs.

Fun fact: It was while browsing Lemonade on the Facebook Ad Library that I decided to pull the tiger and go all in on this company. Funny when most of my posts are about their AI advantages.

[Tim Wulff @timwulff]

@jakebrowatzke @Lemonade_Inc @jakebrowatzke Thanks for sharing, awesome to see. Would love to get more info on these social media ads. Could you share more ads or do a video walk thru Metas ad platform?

What's image retargeting?

[Tim Wulff @timwulff]

@TravisVarnick @PaperBagInvest @michallangers Design of experiments

[Tim Wulff @timwulff]

@cybercatx Most important is that the app works and reminds you to stay logged in with motion tracking enabled. I've tried Geico as well and app/tech was the issue. Kept logging me out so snapshot telematics only

[Tim Wulff @timwulff]

Competition

[Sawyer Merritt @SawyerMerritt]

NEWS: Tesla has launched a new Voice AI agent that was built in-house to improve @Tesla Insurance customer support.

Tesla Insurance customers will now no longer need to talk to a human when requesting basic policy changes. The Voice agent will complete the changes for you. Also, there is a feature that will summarize your previous call, so you don't have to repeat yourself.

This new customer support Voice AI agent is now available to all Tesla Insurance customers.

[Tim Wulff @timwulff]

@ZacksJerryRig @Deandawiz why don't you test three year old phones?

[Tim Wulff @timwulff]

Very cool

[Lemonade @Lemonade_Inc]

Check out @LeeTwito & @ShayHDavidson demo @OpenAI's Realtime API in our voice agents platform 🚀

As AI Maya listens, she performs actions based on users’ requests, such adjusting coverages or getting a quote, and sends a text message in the moment to complete the request in just a few taps!