August 25, 2026

The Octopus, the Mask and the Future of Identity — at RISE Maui

Advanced agents and a lot of aloha — August 17–21 on Maui, benefiting Lāhainā

By Seth Caldwell · August 25, 2026

Three scenes from RISE Maui 2026: a morning reiki and yoga reset on the lawn, Seth Caldwell on the Advanced Agents stage, and the New Intelligence panel — Morning reset on the lawn, the Advanced Agents stage, and the New Intelligence panel. Photos courtesy of RISE Maui.

The inaugural RISE Maui Summit brought a spirit and connection to my life in many mysterious Maui ways. For five days in August, the Hyatt Regency Maui and the hillside slopes of Hua Momona Farms hosted a new kind of summit — Regeneration, Innovation, and Sustainability, grounded in Native Hawaiian perspective, with proceeds benefiting Lāhainā. I'm still wearing the wristband.

The Talk

I spoke on advanced agents using an octopus analogy — a playful map for personal AI agents, trusted avatars, and agentic accountability. The slides, as presented at the summit:

Opening slide: The Octopus, the Mask and the Future of Identity — a playful map for personal AI agents, trusted avatars, and agentic accountability — Click to view the full deck.

The thread running through it: as agents start doing real work for real people, the missing layer isn't intelligence — it's verifiable human identity. Deepfakes get cheaper every month. The answer isn't to slow AI down; it's cryptographic proof of the human on the other end, so an avatar can act for you without anyone being able to act as you. That's the thesis behind VoiceCert and it's the foundation under every Masky avatar. My speaker profile is on the RISE Maui speakers page.

Built on Maui, With Maui

A digital clone for a Maui doctor

I worked with Dr. Norman Estin — a physician who has served Maui for decades — on creating his digital clone with AI. Watching a doctor meet his own avatar for the first time, and immediately start thinking about who it could help, is exactly why we build this.

Farms at 1,200 feet

With Suntana Villanueva I visited local farms and met folks from the Hawaii Farmers Union. The summit's regeneration track wasn't abstract — it was standing on Kapalua hillside at Hua Momona Farms, which grows food for the community it feeds.

The People

The best part of RISE Maui was the people I now message daily. Diego Sabino and I bonded over our World of Warcraft and Hearthstone histories. Jason K. Resch and I talked science fiction — and he joined me for his first snorkel. Dr. Sasha Luccioni, who keynoted on sustainable AI, was as welcoming in person as her work suggests. Matthias Scheutz and I went deep into a philosophical debate about LLM consciousness and neurosymbolic AI. And meeting Eugene Roddenberry was epic — we talked about storytelling's role in meeting the issues of our time, which is about as on-brand for a Roddenberry as it gets.

New friends Kat Wissner, Jackie Keefe, Duane Sparkman, Manesha Sian, and Anthony Moseley made the week feel like an 'ohana — many of the best conversations and connections took place at the nightly 9pm "hot tub club." Speakers like Bernard Fowler, Dr. Jun Yao, and Chef Zach Laidlaw kept every session surprising.

W. Kamaunu Kahaialii taught us an ancient connection ritual that touched my spiritual side more than anything in years — it inspired the aloha-circle.com project, soon to come alive in the Maui airport. Mahalo to founder Gary Grube and the Hua Momona Foundation — which has served nearly 100,000 meals to those impacted by the Lāhainā fires — for making the whole thing happen.

RISE Maui mahalo card: founder Gary Grube on stage, a traditional honi greeting, and Dr. Sasha Luccioni's keynote on sustainable AI — Mahalo from the summit — Gary Grube, a honi greeting, and Dr. Sasha Luccioni's keynote. Photos courtesy of RISE Maui.

AI should be used to create a better future — through a lens of sustainability and human flourishing. RISE Maui was that lens for a week. We left with new colleagues, new friends on the island, and a clearer sense of what we're building toward.

— Seth Caldwell, Masky