Pillar
Money decisions
Forecasting that doesn’t lie. Pricing that doesn’t apologize. Cash, capital, and the line items most owners avoid until they can’t.
Every money decision a founder makes lives somewhere between a forecast and a regret. The forecast is the version on the slide. The regret is the version the company actually paid for.
The pattern that produces the regret is consistent across companies, stages, and industries. Inputs that should be honest get bent toward the answer the room wants. A renewal that should have been derisked becomes the bridge that didn't hold. A line item that should have been cut at 12 months of runway becomes the layoff at six.
The essays below cover the mechanics — forecasting that doesn't lie, the four signals that fire before the bank balance does, the customer concentration nobody named, the deferred revenue you already spent. They are the money decisions the operator can still make. The ones you cannot is what makes them worth writing about.
Start here
Never pay SDRs for meetings booked
Pay SDRs on meetings booked and meetings double while closed-won falls. The plan pays for what it says, so write it on the number you want moved.
Your Real CAC Is 3x the Dashboard Number
Your dashboard CAC skips the hours you spend selling and onboarding. Price them, set a payback ceiling, and stop spend when loaded CAC crosses it.
The Reserve Account Nobody Touches
At one company, $300K sat in a checking account earning 0.1% for fourteen months. Nobody moved it, because moving it meant a decision nobody wanted to own.
More on money decisions
- The Interest Rate on Your Customers
- 0.7% now, $480,000 in five years
- The Procurement Conversation You Skipped
- Your Pricing Page Is a Sales Tool, Not a Disclosure
- The Renewal Math Nobody Runs
- The Bridge Round Prices You
- Three Customer Concentrations
- October's Forecast Misses by Seven Figures
- Working Capital, Quietly
- Margin Drift
- Three Numbers, One Page
- The Discount Nobody Tracked
- The forecast number nobody would bet on
- The CFO who reported gross instead of net
- Sixty Percent More Dinners