SHAWNACHIUPPI
Turning a factory of ideas into purposeful experiences people connect with.
Work With Me
From the hospitality floor to the frontier of tech.
Shawna Chiuppi is an American serial founder and investor with a visionary entrepreneurial instinct. She is currently Chief Experience Officer at Roonify, an AI-powered relational wellness platform, and the founder of Whimity, a micro-generosity platform, and Wepa!, a Puerto Rico-based hospitality solution agency. Alongside these, she is currently involved and co-founder in additional ventures across the DGTLGAL umbrella. After five years of observing the blockchain and AI industries, she retired from hospitality early in 2024, and now nurtures her portfolio with passion.
THE VENTURES
Roonify
The flagship company, building a category-defining relational wellness product to help people navigate difficult conversations safely and build healthier communication habits over time.
Roonify Labs
The experimental R&D arm, prototyping what comes next at the intersection between blockchain technology, AI, and wellness optimization.
Earthwiser
An AI-powered companion for conscious travel that helps you track your impact and choose where you go with intention.
StayBid
A last-minute vacation rental marketplace where travelers bid on stays and hosts negotiate in real time.
Whimity
A micro-generosity platform that turns small acts of giving into everyday moments of connection.
Wepa!
A Puerto Rico-based hospitality agency crafting standout digital experiences for venues and brands.
"I see experiences before they exist, and I build them by drawing on everywhere I've already been. I shaped my life around experiencing the world. Now it all collapses into a single instinct for how a thing should feel. Freedom lets me build without limits."