Writing & Ideas

The hardest part of AI is human adoption. Anthropic and OpenAI just put $5 billion behind that.

The P in ERP stands for Planning, but it hasn't planned anything in decades. Agents are about to call that bluff.

Everyone's debating whether SaaS or "Services as Software" wins. Nobody's asking the harder question.

Foundation Capital and Dharmesh Shah are both right. They're also both missing something.

BCG's prescription for scaling AI is 10% of the effort on algorithms, 20% on data and technology, 70% on people and process. That may be why the hyperscalers are hiring thousands of forward-deployed engineers and the frontier labs are bankrolling services arms of their own.

The most experienced founders treat finance as an investment, not a cost center. Here's why.

Part I covered the four dynamics that shape every venture-backed cap table. Part II is about what those dynamics do to your money.

The most consequential decisions in your company are being made inside a spreadsheet nobody's maintaining.

AI agents are entering the finance org chart. What that means for how you build your team.

Dick Fosbury and the future of AI adoption.

The finance function is changing. The role at the top of it isn't going anywhere.

The more you optimize a finance hire for one stage, the less likely they are to succeed at the next.

You don't need a strategy deck. You need a Wednesday afternoon and a willingness to be wrong.

With Charlie O'Donnell and Propeller CEO Raymond Nieuwenhuizen. Reinventing a company that still works, and the decision every founder eventually faces: rebuild while things are good, or wait until the runway forces it.

With Charlie O'Donnell. When a founder isn't confident in their own judgment, investors fill the void — expanding the concept beyond cap tables into board dynamics, executive hiring, and the founder-CEO transition.

Why the most consequential decisions in your company live inside a spreadsheet nobody's maintaining.

What's working in AI-powered finance operations versus what's still more hype than reality.

Why the title doesn't match the job, and what that means for founders building finance teams.

Why margins fall before they rise, the working capital death spiral, the Billion-Dollar Beverage Blueprint behind Olipop, Poppi, and Liquid Death, and what changes after a $100M raise.

The Hard Part of AI Isn't AI, plus the Building the Plane While Flying It webinar and a masterclass in CPG finance. Statement Stat: only 25% of financial modeling leaders hold the human accountable when an AI-assisted model gets it wrong.

Great Founders Know When Finance Pays for Itself, plus The Confidence Vacuum webinar. Statement Stat: median AI spend at VC-backed companies rose from $2,000 to $50,000 in two years.

Your Cap Table Is Your Strategy, both parts, and the launch of PropellerOS. Statement Stat, filed on Star Wars Day: 284 planets in the Galactic Empire, 33 of them aligned with the Rebel Alliance.

Your Next Finance Hire Might Not Be a Person, plus client news from KiwiCo, Pair Eyewear, The Farmer's Dog and OLIPOP. Statement Stat: one in three corporate finance job postings now references AI, up from one in four a year earlier.

The Backward Jump, on Dick Fosbury and the future of AI adoption, plus Expo West. Statement Stat: Accenture has reskilled 550,000 employees on generative AI and now weighs AI fluency in promotion decisions.

AI Won't Take the CFO Job, on why context is the new moat, plus the five AI use cases finance teams are actually deploying. Statement Stat: 37% of the time AI saves gets spent validating and reworking what it produced.

The Talent Paradox, on why your first finance hire is NGMI, plus two AI webinars for finance teams. Statement Stat: 48% of CFOs name staff resistance to new technology as a major workforce challenge.

The Leader's Guide to Driving AI Adoption Without Breaking Your Team, plus four questions with Chief AI Officer Todd Rebner. Statement Stat: five years ago 70% of CFOs took a conservative approach to AI. Today 4% do.

The Growth Stage Dilemma, and the launch of Propeller's Growth Stage Team for companies between $30M and $300M. Statement Stat: 38% of VCs expect deal activity to rise over the next year, down from 58%.

Stop Worrying About Your AI Strategy and Start Experimenting, plus when the right CRM becomes the wrong one. Statement Stat: 44% of US unicorns were founded by immigrants.

Unicorn Bingo with OLIPOP, poppi and Liquid Death, plus what to do about tariffs. Statement Stat: 2,221 public-company CEOs departed in 2024, the most since tracking began in 2002.