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Why most schools are preparing kids for 1985 — and how to fix it. Join 5,000+ Ruckus Makers who want to Do School Different 👉 https://ruckusmakers.news/subscribe Anna Rita Pergolizzi-Wentworth is building a future fluent school on Wall Street. Her students launch AI companies, travel globally, and grow cultural intelligence. This episode is a masterclass in bold leadership, balance, and building a school worth showing up for. ⌚️ TIMESTAMPS 00:00 - Future fluency vs. 1985 education 01:07 - Meet Anna Rita Pergolizzi-Wentworth 03:31 - Why she almost became a spy 07:08 - Building a jungle school in Costa Rica 10:57 - Leadership design principles for “doing school different” 12:21 - How having kids changed her view on education 15:01 - The power of being a founding student 16:37 - AI sprints, risk-taking, and balance at Pine Street 20:17 - Why Pine Street isn’t for everyone 26:23 - Teacher happiness as a retention strategy 30:13 - The “Green Book” tradition 34:52 - Culture fit and recruiting happy teachers 37:22 - Why staying small creates bigger opportunities 40:00 - Powerful parent partnerships 42:04 - School marquee message: Raise thinkers, embrace humanity, teach for tomorrow 43:08 - 3 principles for building a dream school 44:55 - Final message: Live boldly WHENEVER YOU ARE READY … HERE ARE 3 WAYS TO CONTINUE YOUR DO SCHOOL DIFFERENT JOURNEY: 🗞️ Read Ruckus Makers — Exclusive content on Substack. Premium leadership insights, AI prompts and custom gpts, new books before the bookshelf. https://ruckusmakers.media 💥 Join The Ruckus Maker Club — Our private network + workshops, The Automatic School tools, AI Prompt Library, and more: https://ruckusmakers.club/join 🧨 Apply to the Mastermind — Weekly coaching, peer mentorship, and our proven leadership system (The Ruckus Maker Flywheel) to help you transform your campus: https://betterleadersbetterschools.co...