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Presenting an Annual Plan (AI-Era Edition)
What I present to the board for approval and how AI stuff has impacted it
Nov 3
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October 2026
A $300M Earnout Goes Poof 🫠 | Pepsi vs Poppi
Don’t count on the earnout... How often do earnouts actually pay out?
Oct 30
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🚀 Anthropic’s S-1: Finance Takeaways
Key financial numbers, accounting stuff, and things I found interesting
Oct 26
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The Current State of AI Tokenomics | What CFOs Should Know
Guest post by Peter Walker (Head of Insights at OpenRouter)
Oct 22
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Stop Using The Term “Renewal”
Procurement in the age of AI
Oct 15
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ARR vs GAAP Revenue | Spotting “ARR” Lies
Your board wants to understand the gap between ARR, GAAP revenue, and cash
Oct 13
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Cognition vs Factory | Conflicts of Interest in the Boardroom
Board observers joining rivals. VCs backing both sides. When do competing interests become a problem and how should they be handled?
Oct 7
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September 2026
Harvey vs Legora | When Are Terrible Gross Margins OK?
Plus: Where AI costs belong on the P&L and what actually goes into COGS
Sep 30
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How I’d Use AI to Commit Fraud
Fake receipts, fabricated email approvals, and the controls that kept an AP team from falling for a sophisticated fraud attempt
Sep 23
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New ICONIQ Benchmarks | AI-Native Metrics Are Insane...
🚨 Warning: This report might make you feel like a failure. Proceed with caution.
Sep 20
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Pulley is “Winding Down” | What Happened?
They grew to ~$20M in ARR, had a decent product, and couldn’t find a buyer?
Sep 17
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Top 10 highest-paid people at your company
Are sales reps overpaid? Here’s how I think about sales rep vs executive compensation.
Sep 10
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