2555 Ventures
Background · Founder & operator

Connor
O’Hearn

I build small, durable companies at the seam of design, applied AI, and capital, plus the internal tools that make them run. Below is the path that got here, and what it has become.

2012–2016

Foundations

Shaker Heights, OH · University School · Miami University

Born and raised in Shaker Heights, Ohio. I went to University School, then to Miami University’s Farmer School of Business, where I earned a B.S. in Supply Chain & Operations Management and led in student government. It set the pattern for everything since: a habit of collecting skills, built on operations, logistics, and the discipline of running things well.

B.S. Supply Chain & OpsSupply chain mgmtOperations mgmtLogisticsProcess designLeadershipPublic speaking
2016–2019

Early career

Textron Aviation · Kansas → Boston

I moved to Kansas and then to Boston to sell airplanes for Textron Aviation. It taught me how to sell something genuinely complex, build relationships that last, and carry a large territory on my own. Different city, different industry, more in the bucket.

Enterprise salesRelationship buildingTerritory managementNegotiationAccount managementCommercial strategy
2019–2021

Back to school

Miami University · M.A. Geography + GIS

Then I did something a little unusual: I went back to Miami for a master’s. I earned an M.A. in Geography with a GIS certificate and leaned hard into the analytical side, research, statistics, Python, and spatial analysis. Going back was itself a deliberate act of collecting skills.

M.A. GeographyGIS CertificateFAA Part 107 PilotResearchData analysisStatisticsPythonGIS & spatial analysisCartography
2021–2024

Early AI experience

Pieces for Developers

At Pieces for Developers, an AI developer-tools startup, I sourced and led our partnership with Microsoft as a co-development partner for Microsoft Copilot. I saw early what agent orchestration could become, and got real exposure to building AI into business tools.

Strategic partnershipsBusiness developmentGo-to-marketAgent orchestrationDeveloper toolsProduct strategy
2024–Now

Out on my own

2555 Ventures · Savannah, GA

In 2024 I went independent, consulting for startups and investment firms while learning to build and ship in earnest. This is where the most has happened: more skills, more certifications, a wider network. I moved to Savannah, Georgia, and today I run Maai Designs, Maai Services, and Maai Machines, and I am the architect and builder behind MOCO.

Wharton FP&AApplied AIMulti-agent systemsClaude CodeModel routingPrompt & context eng.RAGLocal AI deploymentApple siliconNext.js & VercelBrand & web designDiligence tooling
Collected
A running tally, collected along the way
Skills0
Certs0
Degrees0
Scroll the story to fill the bucket…

What I’m building

Four operating ventures and a set of internal instruments, the same things you can orbit on the home spiral.

Venture

maaiservices.com

AI services for small business.

Venture

maaidesigns.com

Editorial web & brand studio.

Venture

maaimachines.com

Private local AI on Apple silicon.

Venture

askmoco.com

Multi-agent marketing platform.

Instrument

RFP Tool

Draft & answer RFPs faster.

Instrument

Quoting Tool

Scoped quotes in minutes.

Instrument

Due Diligence Tool

Investment diligence, structured.

Instrument

Deal Sourcing Tool

Surface deals worth a look.

Instrument

Real-Estate Sourcing

Find & filter property.

Building toward

Grow Maai Designs into a business serving hundreds of small business owners. Upskill dozens of teams through Maai Services. And help deploy local AI infrastructure across the Southeast and the wider United States. I believe local AI, and real sovereignty over your access to models, is going to matter enormously.