Dr. No #56 – Never trust someone who loses nothing if they’re wrong

Hey Harvey Specter,

Taleb doesn’t care about politeness. He cares about survival. In Skin in the Game, he hammers one idea: never take advice (or contracts) from someone who doesn’t share your risks.

1. Food for Thought

Who in your business bets with your legal chips — while walking away untouched if it explodes?

2. Big Ideas for GCs (Taleb-style)

• Risk symmetry = fairness. If Sales wants to sign the customer-friendly nightmare clause, ask them to co-sign the litigation budget. Watch their courage fade.

• Accountability builds influence. The GC who says, “I’ll sign my name to this call” is the GC who gets listened to.

• Beware of experts without scars. Consultants love theory. Real leaders live consequences. You know the difference.

3. Mental Model – The Principal-Agent Problem

Agents act for principals but chase their own interests.
GC application? Align incentives. Or better: stop being the agent, start being the principal in risk decisions.

4. AI Booster – Pepper

Your AI secretary. Manages your meetings, schedules, and chaos so you can focus on where the real risk lies. Because the GC’s job isn’t logistics, it’s leverage.

5. Quote to Reflect

“Courage is not the absence of fear, but the triumph over it.” – Nelson Mandela

P.S.
Data privacy contracts are the new minefield: Schrems II, DPAs, hidden indemnities. One misstep and regulators (or journalists) come knocking.

Ambar fractional privacy counsel parachute in to renegotiate, redraft, and de-risk your vendor stack.

Book a call with Ambar — stop gambling with someone else’s chips.

Talk soon,

Rosa and Manuel