Dalton Gregory

Founder

About

I've been an entrepreneur since I was 8. Shoveling driveways. Mowing lawns. Running a landscaping company before I could vote. Almost two decades later, I haven't stopped. Now I'm building what I want to spend the next ten years on.

I'm from Wyoming. My parents have launched, bought, and grown companies for as long as I can remember.

When COVID hit, I dropped out of college and moved to Big Sky, Montana, to work for a restoration company. That led to two years in property management and gave me a firsthand look at the problems contractors face every day.

I later returned to Wyoming, finished school, started O3, ran the campus blockchain club, won the Daniels Fund Ethical Startup Award at Wyoming's Ellbogen $50K startup competition, and graduated from the University of Wyoming.

After graduation, I helped over 100 organizations and trained 500+ professionals on AI across the mountain west. I then moved into my next venture where I cofounded Jump Partners as Chief Technologist and helped launch MyProtection.AI.

Earlier this year, I returned to O3 and its customers, where I found the opportunity that turned into Plentitude. Today, I'm cofounder and CEO, building Plentitude for specialty construction companies.

Ventures

Plentitude, Inc.

Active

Cofounder & CEO · Apr 2026 to Present

Building Parity, the AI platform for restoration contractors. Turns voice, photos, and field notes into a calibrated estimate in under 60 seconds, then helps contractors win more claims.

founding partner landed

$51K

LTV

4 wks

idea to customer

O3 LLC

Founder · Jun 2023 to Apr 2026

AI implementation company focused on workflow automation, enablement, and practical deployment. Delivered end to end engagements across 100+ organizations, translating needs into scoped execution plans with measurable adoption outcomes. Rolled into Plentitude in 2026.

100+

orgs served

500+

professionals trained

Jump Partners Inc.

Cofounder & Chief Technologist · Sep 2024 to Mar 2026

Intellectual equity company providing strategic guidance, capital, and technical resources to AI native startups. Served as execution arm to leadership, ran weekly priorities, maintained action/decision logs, led M&A diligence, and built financial models across two verticals.

$350K

preseed capital raised

M&A diligence

subsidiaries

My Protection AI

Cofounder · Oct 2024 to Mar 2026

AI powered scam and fraud protection SaaS for consumers. Led cross functional execution across product, GTM, partnerships, and customer success. Built and shipped production applications.

50+

releases shipped

15+

enterprise partners

Press & Community

Sheridan Community Land Trust

O3 creates a culture of reciprocity by donating Daniels Fund award prize to SCLT

Sep 2024

University of Wyoming

Local company wins Ellbogen Entrepreneurship Competition Daniels Fund Ethical Startup Award

Aug 2024

Sheridan Media