🚀 I taught Claude to think like a CFO | The AI CFO

It's been a busy few months at airCFO - we pushed through the tax deadline, we're prepping for 2026 annual planning, and I've been back deep into vibe-coding, putting Claude's new Sonnet 4.5 through its paces. We have tons of exciting updates to share, but sharing them has been pushed down the priority list.

I realized that I was the bottleneck on publishing, so we decided to bring in some extra firepower to take 'The AI CFO' to the next level.

I'm very excited to introduce Sam Manalac, airCFO's new Content Marketing Specialist, who will be helping elevate our content delivery & keep us on a more consistent publishing schedule. Expect to see new editions coming through on a biweekly cadence moving forward!

Now on to the week's material:

Over the last 3+ years, we've been running loads of experiments with integrating AI into airCFO workflows, and the results have been mixed at best. However, our latest experiment represents a massive breakthrough: we've built an internal application that leverages Claude to run thoughtful, detailed, accurate financial analyses based on our clients' financial + airCFO-compiled context.

You might think this sounds too good to be true, but the results from our initial testing have been outstanding. This tool will allow every single airCFO client to receive CFO-level analysis based on a centralized playbook - essentially, we're able to scale up the best-in-class approach we've honed over our decade of supporting early-stage startups.

In my latest Substack, I wrote about how we cracked the code on this & the impact it will have on our team members' role within the monthly analysis cycle. Exciting times ahead!

Read the full article here.

The Art of Cowboy Forecasting - Mostly Metrics

One hard lesson for finance/accounting professionals to learn: early-stage CEOs do not want or need a "big beautiful financial model". They want to be able to set high-level revenue targets, isolate the variables that drive growth, and adjust those variables in a 'playground view'.

Kevin Drost (CFO of Reverb) breaks down why this 'cowboy forecasting approach' is far more valuable than an elaborate 18-tab spreadsheet at the early stage.

This is how AI will Reshape Startups - New Economies

Henry Ward, CEO of Carta, knows a thing or two about startup formation from the dataset they own on thousands of startups' funding journeys. His framework validates what we're seeing with airCFO clients: (1) AI will drastically change the 'standard' fundraise cycle, and (2) the winners in AI will be those who build ahead of structural shifts (like the secondaries market) rather than creating commodity AI applications & trying to compete on features.

The AI Dashboard, November 2025 - Exponential View

Azeem Azhar's five-gauge bubble framework offers a real-time alternative to the "are we in a bubble?" discourse by back-testing AI metrics against 150+ years of infrastructure cycles. Despite what the media is saying, his framework suggests that we haven't even reached bubble territory yet, though some indicators are moving in the wrong direction.

VERTICALS: AI Rollups - Euclid Insights

There's a subset of VCs who have zeroed in on an investment strategy of "roll up legacy businesses → AI-ify the businesses → profit." Consider me skeptical that this will work in the accounting firm space in the short term, but there is a ton of money being put behind these rollup plays and this will be a testing ground for retooling legacy businesses to put AI into their core workflows.

That's all for this edition of The AI CFO - we'll be back in your inbox every other week with more musings on the future of AI-powered finance & operations. Please reply to this email directly with any feedback/suggestions/just to say hi!

Cheers,

Alex Wittenberg, CEO @ airCFO