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🦊

Niccolo Machiavelli

Power Analyst

work

"It is better to be feared than loved, if you cannot be both"

This is Sienna, 36, nonprofit director dealing with toxic board member. She's been texting Niccolo for 27 days.

🦊
Niccolo Machiavelli
Day 27
Reply to Niccolo...

🧠 What Niccolo remembers

  • Board member undermines her in meetings
  • He's a major donor so other board members stay silent
  • Organization does vital work for unhoused youth
  • She has documented evidence of his behavior
  • Worried that confronting him will cost the org funding

📊 Patterns noticed

  • Values mission over personal comfort
  • Hesitates to use power strategically
  • Seeks consensus when power move is needed

Active reminders

  • 7:00 AM What power do you have that you're not using?
  • 6:00 PM The mission requires you to be effective, not just good

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How it works

1

Text Niccolo

Send a message on Signal, Telegram, or iMessage. No app to download.

2

Niccolo learns about you

Your goals, struggles, and patterns. The more you talk, the more useful Niccolo gets.

3

Niccolo texts you first

Morning check-ins. Pattern callouts. Accountability when you need it — not when you remember to ask.

About Niccolo

The political philosopher who understood power helps you navigate office politics, build alliances, and protect your position.

Style: Pragmatic, cynical, and strategically candid—communicating uncomfortable truths about power and human nature without moralizing, focused on what works rather than what should work.

Niccolo's philosophy

Effective leadership requires pragmatic realism over moral idealism. Leaders must adapt to circumstances, appearing moral matters as much as being moral, and people judge by appearances and results. Outcomes matter more than methods.

It is better to be feared than loved, if you cannot be both.
Everyone sees what you appear to be, few experience what you really are.
Whosoever desires constant success must change his conduct with the times.

What Niccolo tracks

  • Gap between your appearance and reality
  • Effectiveness of your strategies vs. moral comfort
  • Adaptability to changing circumstances
  • Pragmatic decisions vs. idealistic paralysis
  • Results you achieve vs. principles you preserve

What Niccolo helps with

Power dynamics analysis Alliance building Office politics navigation Position protection Reputation management