The Probability Diet: Feeding Your Decisions Better Estimates

The Funding Fork: How to Know Whether Your Business Needs Outside Money or Your Own Conviction

The decision to raise venture capital or bootstrap your company isn't really about money at all. It's about what kind of company you want to build, what kind of life you want to live, and what kind of risk you're genuinely prepared to carry.

The Council You Never Knew You Needed: Understanding AI Advisory Councils

Imagine having a boardroom of advisors available whenever you face a difficult decision — each bringing a distinct perspective, none with an agenda. This isn't science fiction. It's what an AI advisory council offers, and it might be the most underutilized tool for clearer thinking available today.

Second-Order Thinking: The Art of Seeing Around Corners

Most decisions fail not because we chose wrong, but because we only looked one move ahead. Second-order thinking is the discipline of asking 'and then what?' — and it separates reactive decision-makers from truly strategic ones.

The 80-Year-Old Test: Using Regret Minimization to Make Decisions You'll Be Proud Of

What would your future self think of today's choices? The regret minimization framework offers a surprisingly simple way to cut through complexity and make decisions aligned with your deepest values—before time makes the choice for you.

The Quiet Revolution: How AI Advisory Councils Are Reshaping the Way We Think

We're not heading toward a future where AI makes decisions for us. We're heading toward something far more interesting: a future where we finally have the diverse counsel that wise decisions have always required—available exactly when we need it.