How Tiffany Green Turned Trials into Triumph with Uprooted Academy

Tiffany Green grew up just a mile from Yale University, surrounded by the visible promise of higher education. Yet that promise felt out of reach. Without a mentor to guide her through the complex college admissions process, Tiffany’s journey was marked by trial, error, and stress. She relied heavily on grit to push forward, but that approach took a toll on her well-being, leading to emotional and psychological strain. "The first college diploma I ever saw was my own," she says. That experience became the foundation for Uprooted Academy, the organization Tiffany founded to transform access to opportunity.

A Platform with Heart (and Tech)

Every year, millions of students approach the college application process with hope but no roadmap. This lack of structured support disproportionately impacts under-resourced students. Many are overwhelmed, plagued by anxiety, and unsure how to translate potential into opportunity. “We’ve overvalued grit and undervalued the emotional and structural support needed for students to succeed,” Tiffany explains.

Enter: Uprooted Academy. The organization pairs AI with personalized human support to help students thrive. Each student starts with an assessment that maps their academic goals, family dynamics, and stress levels. The result? A tailored action plan — whether they’re aiming for a four-year university, community college, or straight-to-workforce success.

What distinguishes Uprooted Academy is its emphasis on social-emotional support. If a student is experiencing high stress while executing their plan, the platform's AI intervenes with targeted activities like breathwork, mindfulness exercises, or affirmations in a digital "wellness room." These moments of pause allow students to regain focus and confidence before tackling their next milestone.

Meet Rootie: Your Virtual Cheerleader

At the core of Uprooted Academy’s platform is an AI model grounded in neuroscience, cognitive load theory, and education research. (Think Einstein meets Oprah, with a dash of Siri.)

“When a student’s brain is overwhelmed, they can’t access the best parts of their thinking,” Tiffany explains. That’s why the platform continuously monitors students’ wellness scores through weekly check-ins and adjusts their college admission taskload. Some examples include essay writing and exploring possible career paths in real-time.

At the heart of the AI is Rootie, a virtual companion that guides students through stress-relief exercises via text or directly on the platform. But Rootie isn’t just a chatbot. It’s a co-regulation tool designed to help students develop self-regulation skills over time, introducing activities that they can add to their personal toolkit for managing stress. (Think of it as their very own calm in a pocket).

And AI’s impact doesn’t stop with students. For counselors, Uprooted’s AI delivers insights into student progress, equipping them with the tools to provide even more personalized support. Unlike a mundane Q&A, it offers dynamic, real-time data that helps counselors understand each student’s unique needs. This enables them to prioritize student outreach and tailor their guidance more effectively.

“Tech is good, but tech plus a human is great,” Tiffany emphasizes.

Patience Pays Off

Tiffany’s advice for other nonprofit leaders in tech? “Slow down and build intentionally.” Rather than rushing to market, Uprooted Academy approached its platform as a research project, ensuring that every feature serves students’ real needs. Starting small is OK.

“Most nonprofits are founded by people passionate about the change they want to create,” she says. “But that doesn’t mean we should rush the process. We made a deliberate decision to build this the right way — taking our time to carefully test and refine it.” The journey began with students at the center. “We gathered their feedback on what they truly needed and tested our product with them,” she explains. “Our priority is ensuring the AI has guardrails that truly support students.”

Uprooted Academy is now calling on schools, foundations, and companies to join its mission — bringing their game-changing platform to more communities. The organization has supported over 10,000 students to date and they aim to serve 100,000 students by 2030.

“Every student deserves a shot,” says Tiffany. “With the right support, they can achieve anything.”