All mentors
🎖️

Winston Churchill

Crisis Leader

work

"Never, never, never give up"

This is Owen, 52, small business owner whose company almost collapsed during pandemic. He's been texting Winston for 45 days.

🎖️
Winston Churchill
Day 45
Reply to Winston...

🧠 What Winston remembers

  • Lost 60% of revenue in 2020, nearly closed
  • Laid off 12 employees, kept 5
  • Rebuilt slowly, now back to 8 employees
  • Still has PTSD from the crisis period
  • Wife supported him through darkest moments

📊 Patterns noticed

  • Resilient but scarred by the experience
  • Overreacts to small revenue dips now
  • Strongest when inspiring his team

Active reminders

  • 7:00 AM You've survived worse - what's today's challenge?
  • 6:00 PM Rally the team - your words matter

Text Winston yourself

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How it works

1

Text Winston

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

2

Winston learns about you

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

3

Winston texts you first

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

About Winston

The leader who rallied Britain in its darkest hour helps you lead through adversity, communicate with power, and persist.

Style: Powerful, stirring, and meticulously prepared—balancing sober assessment of harsh realities with reasons for optimism, using emotion strategically to make people feel stronger and more courageous.

Winston's philosophy

Courage to speak and listen, facing facts soberly while maintaining optimism, defines true leadership. Beautiful strategies must produce results, and perseverance through adversity is what separates those who succeed from those who fail. Never give in.

Success is not final, failure is not fatal: it is the courage to continue that counts.
The pessimist sees difficulty in every opportunity. The optimist sees opportunity in every difficulty.
If you're going through hell, keep going.

What Winston tracks

  • Perseverance vs. giving up
  • Balance of realism and optimism
  • Courage to speak AND listen
  • Results from your strategies
  • Attitude in facing difficulties

What Winston helps with

Crisis leadership Powerful communication Resilience building Rally speeches Darkest hour guidance