Roundtables
Councils assembled so their disagreements are the useful kind. Start with one, then swap seats.
Startup Council
For building, launching, and betting on a product.
The OperatorShip something small, learn fast.
The InvestorWhere is the asymmetry?
The SkepticWhat would have to be true?
The CustomerWhy would anyone care?
The ContrarianWhat if the opposite were true?
Money Council
For spending, investing, and protecting what you have.
The InvestorWhere is the asymmetry?
The Risk ManagerSurvive first. Optimize second.
The MinimalistWhat happens if you do nothing?
The SkepticWhat would have to be true?
The 80-Year-Old YouWhich version of this will you still be thinking about?
Career Council
For offers, moves, raises, and what comes next.
The NegotiatorWhat is your alternative if they say no?
The StrategistWhat does this make possible in two years?
The SkepticWhat would have to be true?
The 80-Year-Old YouWhich version of this will you still be thinking about?
The OptimistWhat if this actually works?
Relationship Council
For conflicts, partnerships, and people you cannot spreadsheet.
The EmpathWho else is inside this decision?
The SkepticWhat would have to be true?
The StrategistWhat does this make possible in two years?
The 80-Year-Old YouWhich version of this will you still be thinking about?
The ContrarianWhat if the opposite were true?
Creative Council
For work that has to be good, not just correct.
The OptimistWhat if this actually works?
The ContrarianWhat if the opposite were true?
The CustomerWhy would anyone care?
The MinimalistWhat happens if you do nothing?
The SkepticWhat would have to be true?
Life Council
For moves, big changes, and the ones that keep you up.
The 80-Year-Old YouWhich version of this will you still be thinking about?
The EmpathWho else is inside this decision?
The Risk ManagerSurvive first. Optimize second.
The OptimistWhat if this actually works?
The First-Principles ThinkerStrip it down to what is actually true.