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Welcome back to the newsletter where we talk about how companies talk about their numbers… and also talk about how the public talks about those companies talking about their numbers.

Well, I can’t believe I'm saying this, but I think everyone is completely over reacting to these leaked Anthropic numbers, while simultaneously under reacting to how these new AI companies are calculating their run rate revenue.

We’re focusing on the wrong thing.

TL;DR: Anthropic’s FY 25 numbers got out, showing

  • Net loss of $42 billion

  • Revenue of $4.6 billion

  • Plans to spend half a trillion on compute in coming year

Why might this not be as bad as it seems?

1. You really think they aren't going to include 2026 when they file?

We are ten months into the year, people.

These are 2025 numbers, much of which we already knew, or at least sensed. And it excludes the period in which they rocketed from $9B in annualized revenue at the end of last year, to $30B in April, to $65B by the end of July (more on how that’s calculated in a sec).

That’s the fastest growing period in the history of fast growing companies… ever!

Yea, a lot of this is "not good" but it's also "not complete".

2. The $42 billion number overstates what they lost actually running the biz.

It's a shitty headline number to lead with, meant to scare people.

Yes, AI might kill us all (minor point), but that’s not the operating loss from a functional business perspective.

Because $34 billion was a noncash revaluation of financing that may convert into shares.

OK, what's that mean?

It's due to financing choices, likely convertible instruments that will cause dilution at some point as the value of the company goes up. Which is a big deal from a shareholder perspective; you do care about stock charges and warrants that will decrease the value of shares on a one for one basis. But it's a very different thing than paying people who work there, or buying compute (which they buy a lot of), or settling your AWS bill.

If we're talking about operating losses, you've gotta compare $8 billion to the $4.6 billion in revenue. In other words, it cost them roughly $12.6 billion to generate $4.6 billion in topline last year.

Again, not “good” from a unit economics perspective! But if you're assessing the costs of actually running Anthropic, look at the operating loss. If you're assessing what existing shareholders ultimately own, account for the convertibles too.

3. What this data seems to corroborate is some fugazi around the revenue numbers.

Around the same time these numbers came out, a fascinating interview dropped where Harry Stebbings spoke with Higgsfield founder and CEO Alex Mashrabov. Alex made a comment, almost in passing, that they calculate annual revenue "the same way OpenAI and Anthropic do."

They take the last 28 days of revenue and multiply by 13, which gets you to 364 days.

(Because that’s totally a standard Roman Gregorian calendar cut.)

When I heard that, it made me go back and look at Anthropic's reported revenue numbers over time. And it seems to check out.

Anthropic reported $4.6B of actual revenue for 2025. At the end of the same year, we were talking about them being at roughly $9B of annualized revenue. A bit of a gappppp.

One view tells you how much revenue you actually generated over the year. The other looks at what you did over the last 28 days and says, "OK, what if we did that (looking for random number to use) 13 times?" This view is an expression of your theoretical capacity.

(I like to sprint a mile as fast as I can, multiply by 13, and brag to people that’s my half marathon time)

And given how fast these companies are growing, those numbers are going to be VERY different. And the 2026 revenue Anthropic eventually reports is def not going to match the $65B we've been quoting in the OpenAI vs Anthropic revenue arms race.

Should we panic?

Anthropic‘s 2025 numbers and what we know about 2026 so far did not make me feel like the sky was falling. Before we start reassembling the chairs on the deck of the Titanic, I'd like to see what the 2026 figures print. Are the unit economics getting any better? Because if this isn’t “at scale” then what is?

Hopefully they aren't still selling a dollar for sixty cents… Maybe they’re selling a dollar for 75 cents now?

Time will tell, and that time looks like a late November IPO.

But back to the revenue crimes

Here's how Higgsfield described the math:

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“We look at revenue over the last 28 days and multiply it by 13.

What is very important is that we take revenue, not sales. If that is an annual subscription or annual enterprise contract, we prorate this across 12 months.

It is only live revenue. We are not taking three-year enterprise deals and baking them into a $1BN figure.”

I've written at length about the crimes of CARR, or Contracted Annual Recurring Revenue.

But with each new pricing model we get new revenue crimes. Pricing necessity is the mother of all revenue invention.

I posted this Lead Edge hierarchy last week because it remains one of the greatest pieces of finance literature ever produced.

The premise is that if the number at the top looks like shit, keep moving down the list until you find one that looks good.

I think we need to make an addition.

If companies don't have good TTM revenue, they report the last 28 days of revenue multiplied by 13.

To be fair, this is WAY less criminal than most of the stuff further down the hierarchy. They did not report that they were the 13th best place to work in Topeka, Kansas. At least it's live revenue.

They're also not taking some three-year ramped enterprise contract, grabbing the biggest number exiting year three, and pretending they're servicing all of it today.

You can’t live off CARR. If I fed my dog CARR, he'd die.

Now, I’m no stranger to “run rate revenue.” Back in the day, we'd actually call it that - take your last quarter and multiply it by four.

I like the quarterly version better than monthly (or 13) because you have three months in there to smooth things out. Twenty-eight days is where it starts to get suspect.

When a really good month gets multiplied by 13 you look like a rock star. If you run a big promotion, launch a new product, sign a whale or see a giant spike in consumption, every incremental dollar generated during that window gets 13 little friends when you report your annualized number. Suddenly a good month is a great year.

And the shorter your measurement window gets, the more sensitive the number becomes to whatever weird stuff happened recently.

We've already seen public companies wrestle with this in usage-based models. Some use a month. Some use 90 days. MongoDB has even used different windows depending on the type of customer (enterprise vs self serve).

There's no Revenue Police coming to your house to tell you which one is correct (although I will be running for deputy commissioner in 2028).

But the window matters a lot.

The other fun part is that the math eventually works against you.

If you're growing 10% month over month, using your latest 28 days is awesome. You're constantly throwing away older, smaller revenue periods and replacing them with the newest, biggest one.

Now stop growing, or worse, decline 10%.

That same math you loved on the way up will very efficiently annualize your shitty month on the way down.

I bet you dollars to donuts we start hearing a lot more about 90-day averages when that happens.

There's also a question of what you actually use this number for.

For an investor update where you're trying to show how fast a business is growing, I get it. You almost have the opposite problem with GAAP revenue. A trailing twelve-month figure for a company growing this quickly is stale AF.

But I wouldn't want to run the company exclusively off a 28-day annualized number. You could make some whacky operating decisions… Like locking in compute based on a promotional month or under hiring customer support.

AI companies already have the ability to juice demand through credits, free usage, and pricing. Much of their GTM strategy is giving away compute for free.

And this is really the bigger problem with ARR now. We took a metric that used to mean something fairly specific and tried to stuff every new business model into it, taking creative liberties along the way:

  • Subscription ARR turns into

  • CARR turns into

  • Consumption ARR turns into

  • Run-rate revenue turns into

  • 28-day annualized revenue turns into… (turn it off turn it off!)

I wrote last year that usage-based pricing had turned ARR into the Wild West.

We are now in Westworld.

There are no new crimes, just new ways to calculate revenue.

And Lead Edge is going to need a bigger piece of paper.

Weekly Valuation and Efficiency Metrics

Revenue Multiples

Revenue multiples are a shortcut to compare valuations across the technology landscape, where companies may not yet be profitable. The most standard timeframe for revenue multiple comparison is on a “Next Twelve Months” (NTM Revenue) basis.

NTM is a generous cut, as it gives a company “credit” for a full “rolling” future year. It also puts all companies on equal footing, regardless of their fiscal year end and quarterly seasonality.

However, not all technology sectors or monetization strategies receive the same “credit” on their forward revenue, which operators should be aware of when they create comp sets for their own companies. That is why I break them out as separate “indexes”.

Reasons may include:

  • Recurring mix of revenue

  • Stickiness of revenue

  • Average contract size

  • Cost of revenue delivery

  • Criticality of solution

  • Total Addressable Market potential

From a macro perspective, multiples trend higher in low interest environments, and vice versa.

Multiples shown are calculated by taking the Enterprise Value / NTM revenue.

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Enterprise Value is calculated as: Market Capitalization + Total Debt - Cash

Market Cap fluctuates with share price day to day, while Total Debt and Cash are taken from the most recent quarterly financial statements available. That’s why we share this report each week - to keep up with changes in the stock market, and to update for quarterly earnings reports when they drop.

Historically, a 10x NTM Revenue multiple has been viewed as a “premium” valuation reserved for the best of the best companies.

Efficiency

Companies that can do more with less tend to earn higher valuations.

Three of the most common and consistently publicly available metrics to measure efficiency include:

CAC Payback Period: How many months does it take to recoup the cost of acquiring a customer?

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CAC Payback Period is measured as Sales and Marketing costs divided by Revenue Additions, and adjusted by Gross Margin.

Here’s how I do it:

  • Sales and Marketing costs are measured on a TTM basis, but lagged by one quarter (so you skip a quarter, then sum the trailing four quarters of costs). This timeframe smooths for seasonality and recognizes the lead time required to generate pipeline.

  • Revenue is measured as the year-on-year change in the most recent quarter’s sales (so for Q2 of 2024 you’d subtract out Q2 of 2023’s revenue to get the increase), and then multiplied by four to arrive at an annualized revenue increase (e.g., ARR Additions).

  • Gross margin is taken as a % from the most recent quarter (e.g., 82%) to represent the current cost to serve a customer

  • Revenue per Employee: On a per head basis, how much in sales does the company generate each year? The rule of thumb is public companies should be doing north of $450k per employee at scale. This is simple division. And I believe it cuts through all the noise - there’s nowhere to hide.

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Revenue per Employee is calculated as: (TTM Revenue / Total Current Employees)

  • Rule of 40: How does a company balance topline growth with bottom line efficiency? It’s the sum of the company’s revenue growth rate and EBITDA Margin. Netting the two should get you above 40 to pass the test.

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Rule of 40 is calculated as: TTM Revenue Growth % + TTM Adjusted EBITDA Margin %

A few other notes on efficiency metrics:

  • Net Dollar Retention is another great measure of efficiency, but many companies have stopped quoting it as an exact number, choosing instead to disclose if it’s above or below a threshold once a year. It’s also uncommon for some types of companies, like marketplaces, to report it at all.

  • Most public companies don’t report net new ARR, and not all revenue is “recurring”, so I’m doing my best to approximate using changes in reported GAAP revenue. I admit this is a “stricter” view, as it is measuring change in net revenue.

OPEX

Decreasing your OPEX relative to revenue demonstrates Operating Leverage, and leaves more dollars to drop to the bottom line, as companies strive to achieve +25% profitability at scale.

The most common buckets companies put their operating costs into are:

  • Cost of Goods Sold: Customer Support employees, infrastructure to host your business in the cloud, API tolls, and banking fees if you are a FinTech.

  • Sales & Marketing: Sales and Marketing employees, advertising spend, demand gen spend, events, conferences, tools.

  • Research & Development: Product and Engineering employees, development expenses, tools.

  • General & Administrative: Finance, HR, and IT employees… and everything else. Or as I like to call myself “Strategic Backoffice Overhead.”

All of these are taken on a Gaap basis and therefore INCLUDE stock based comp, a non cash expense.

Companies Included

1. Security & Identity (16 companies) Endpoint, network, IAM, security operations. The CISO budget.

CrowdStrike, Palo Alto Networks, Fortinet, Cloudflare, Zscaler, Okta, SentinelOne, SailPoint, Check Point, Qualys, Tenable, Rapid7, Varonis, Rubrik, Mitek, OneSpan

2. Data & AI Infrastructure (13 companies) Modern data stack, AI/ML platforms, vector and analytics infra, GPU compute. Software-native by design.

Snowflake, Arista Networks, Equinix, CoreWeave, MongoDB, DigitalOcean, Nebius, Elastic, Akamai, Fastly, Teradata, C3.ai, Cerebras

3. Dev Tools & Observability (10 companies) Anything bought out of the engineering budget.

Datadog, Atlassian, Figma, Dynatrace, Nutanix, GitLab, UiPath, JFrog, AvePoint, PagerDuty

4. Horizontal SaaS & Back Office (18 companies) Software sold across industries to ops, HR, finance, and collaboration teams. Not vertical-specific.

Oracle, ServiceNow, Workday, ADP, Paychex, Paycom, Paylocity, Zoom, DocuSign, Navan, monday.com, Asana, Workiva, BlackLine, RingCentral, 8x8, Box, Dropbox

5. GTM (MarTech & SalesTech) (16 companies) Anything bought out of the revenue org. Marketing automation, sales engagement, CRM, ad tech, customer experience.

Salesforce, Adobe, HubSpot, The Trade Desk, Twilio, Klaviyo, Braze, ZoomInfo, Freshworks, Amplitude, Five9, Zeta Global, Wix, Sprout Social, Yext, Criteo

6. Vertical SaaS (15 companies) Software built for a specific industry without take-rate or transaction economics.

Palantir, Autodesk, Veeva, Samsara, ServiceTitan, Guidewire, Tyler Technologies, Doximity, Procore, AppFolio, CCC Intelligent Solutions, Blackbaud, nCino, CareCloud, CS Disco

7. Take-Rate Platforms (18 companies) Marketplaces and commerce platforms that earn money on transaction volume.

Uber, Airbnb, Shopify, MercadoLibre, DoorDash, eBay, Zillow, CarGurus, Instacart, Etsy, Toast, Lyft, Opendoor, StubHub, Upwork, Coursera, Ethos, Fiverr

8. Payments & Money Movement (10 companies) The rails. Payment processors, payment infrastructure, B2B payments, treasury. Volume game, utility margins.

Intuit, Fiserv, Adyen, PayPal, Block, Shift4, BILL, Flywire, Marqeta, Lightspeed

9. Consumer Fintech, Lending & Crypto (15 companies) The front-end. Consumer-facing financial apps, BNPL, lending platforms, crypto exchanges. CAC-driven, marketing-heavy, totally different unit economics from #8.

Coinbase, Robinhood, SoFi, Chime, Affirm, Upstart, Circle, Bullish, Figure, Klarna, Sezzle, Gemini, Blend, Remitly, LendingClub

Please check out our data partner, Koyfin. It’s dope.

Wishing you trade at a high revenue and EBITDA multiple,

CJ

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