The philosophy

Amplified, not artificial.

What the chain stores are selling

Generic AI pointed at generic problems. One chatbot, one template, one voice bolted onto a thousand businesses that were supposed to be different. The same flattening force that turned every main street into the same main street — now pointed at how your business actually thinks.

What I'm building instead

Custom smart workflows for small business that they actually own. Your voice, your operations map, your customers, your rules — in a folder you control. If you ever want to leave, you walk with it. The AI amplifies what makes you, you. It doesn't paper over it.

Why Monterey. Why Bearing. →

This coast has always built
real things for real work.

Monterey was founded in 1770 as the capital of Alta California — a Presidio on a bluff, a port, and a town of people who built things with their hands because that's what the place demanded. Two hundred and fifty-five years later, I live and work ten minutes from where that flag first went up. This isn't decorative. It's the whole point.

Before Silicon Valley existed as a concept, Monterey Bay was already a technology story. It was rocket harpoons thrown from open boats at Point Lobos. It was Knut Hovden's cannery machinery mechanizing the Sardine Capital of the World. It was the Naval Postgraduate School taking over the Hotel Del Monte to train officers for real operations. It was Seymour Cray shipping the CDC 1604 — serial number one, the first supercomputer ever sold — to a Monterey loading dock in 1962. It was David Packard launching MBARI with a principle I think about constantly: send instruments to sea, not people. Return information, not samples.

Every chapter of this peninsula's technology story has the same shape. Someone looked at a hard, physical, unsexy problem — fish, submarines, lettuce fields, sardines, shoreline ecology — and pointed the most advanced tools of their era directly at it. And each time, the quality of life for the people who live here went up a notch. New jobs, new skills, new reasons to stay.

I think we're at the beginning of another one of those chapters right now. Maybe the biggest one yet.

1770
The Presidio goes up.

Alta California's first capital. A town founded on the premise that real people doing real work is how you build a place worth living in.

1905 – 1940s
Cannery Row mechanizes.

Hovden's Fish Hopper, automated cutters, chain-driven conveyors. 30+ canneries. Blue-collar work made 10x more productive by ruthless engineering.

1962
Cray's first supercomputer.

Seymour Cray shipped the CDC 1604 — serial number one — to the Naval Postgraduate School. Monterey was the world's first supercomputer customer.

“Send instruments to sea, not people.Return information, not samples.”

— David Packard, MBARI founding principle

And the name

Why I call it Bearing.

The word carries three meanings at once. I didn't pick it because one of them was clever. I picked it because all three of them are the job.

1. A heading
The direction you're going.

Sailors take a bearing before they set out. Every small business owner is already running on instinct — Bearing's job is to turn that instinct into a heading you can steer by.

2. A compass reading
The fix on the horizon.

Our logo is a compass for a reason. Your fingerprint is what makes you different; the bearing is the line between where you are today and where you're trying to get. The AI keeps you on it.

3. A machine part
What lets heavy things turn.

The unglamorous piece inside every real machine — boats, canneries, aircraft, tractors — that lets heavy work happen smoothly. That's the job. Quiet infrastructure that makes the hard stuff possible.

2025 — The next beat

Bearing continues the thread.

AI and open source are about to blow the doors off what a small business can do — the plumber, the baker, the cinema owner, the wedding planner, the dental office. The people who actually built this town and this country. Not software for software's sake. Real tools pointed at real work.

This wave doesn't replace the people who are already great at what they do. It amplifies them. The baker whose sourdough regulars drive across town. The plumber who's earned thirty years of trust on one street. The wedding planner who keeps a binder of every vendor's quirks in her head. AI finally gives them the leverage a chain store used to have — without flattening what made them worth choosing in the first place.

That's what Bearing is for. I built it in Monterey because this coast has been doing exactly that for 255 years, and I don't see any reason to stop now.

Meet the founder

Hi, I'm Nick.

Nick O'Connor, Founder of Bearing

Nick O'Connor

Founder · Bearing

Custom Workflows for Small Business

I grew up in a small business. My father ran a grocery store in Salthill, Galway, Ireland — the kind of place where regulars were family and the staff knew every customer by name. We all worked and pitched in: after school, on weekends, full time every summer and holiday. At the time I thought it was just what families did. Looking back, the way small business owners actually operate — the judgment calls, the trust, the hundred small things they hold in their head — became part of how I see everything. My brother runs the shop today, and it's still that kind of place.

That foundation shaped everything after. Twenty-plus years in Silicon Valley — leading product at the AT&T Foundry in Palo Alto, deploying machine learning at Rakuten that saved millions within months. A once-off opportunity to run a startup program for a Silicon Valley Fortune 500 company led me to starting and building a highly successful business running custom accelerator programs for Cisco, NEC X, NetApp, Alchemist, ZF Group, Ericsson, and SanDisk — and the thread was always the same. The startup teams that won were the ones that worked backwards from the customer. Across 200+ teams, I helped founders find their first customers, figure out product-market fit, and then scale from tens to hundreds to thousands of dollars in monthly revenue. Some landed venture funding; most did not. A few got acquired by companies like Google, Meta, Workday, Rakuten, and many more.

Which brings me to now. It's clear to me — more clear than anything I've seen in twenty years of doing this work — that the real leverage from this wave of AI is going to land with individuals and small businesses, not big companies. At least in the short run. Enterprises are too slow, too political, too committed to the old stack. The people who can actually turn this technology into an unfair advantage are the ones close enough to the work to feel what it changes — the baker, the plumber, the cinema owner, the wedding planner, the dental office. They can move this week. An enterprise can't move this year.

This wave will amplify what those businesses can do — how they serve customers, how they operate, how they compete. In the next few years it'll be obvious to everyone. The businesses that embrace it now will operate on a different level.

I built Bearing to help the people who care about using this technology to enhance what they already do — not replace it. To serve their customers better, strengthen their communities, and run their businesses the way they've always wanted to.

The journey

20+ years building things that work.

2025 — Present

Bearing

Now

Custom Workflows for Small Business

Founder

Custom smart workflows for small business that they actually own. Your voice, your data, your workflows — in a folder you control.

September 2025

Network School

The pivot

Student · frontier skills, in public, with builders

I put myself outside my comfort zone and went. I stayed. Learned the skills on the frontier and then started using them to solve real problems. It rewired how I think about the next ten years of my life — and is the direct reason Bearing exists.

2023 – 2025

Interim Head of Product Growth

B2B Startups + Enterprise Innovation

Worked with technical founders and innovation teams to bridge the gap between brilliant technology and real market demand — building things customers actually want.

2022

Head of Product — AI & Data Platform

Rakuten Symphony

Pivoted an end-to-end data and ML platform from technology-first to customer-first. Deployed dozens of high-value ML use cases, generating millions in savings within months.

2013 – 2020

Startup Accelerator Programs

Cisco, NetApp, NEC X, Alchemist, ZF Group, Ericsson, SanDisk, Tata, Citrix, Red Hat, Arrow

Designed and ran 36+ growth programs for 200+ startup and innovation teams across IoT, cybersecurity, telehealth, AI/ML, and more. Multiple acquisitions (Google, Meta, Workday, Rakuten), 14+ venture-funded startups, and an NPS of 100 — multiple times.

2011 – 2013

Product Manager

AT&T Foundry

Built a platform to expose Telco APIs in REST format for app developers, then led multiple teams solving customer business problems — from configurable IVR systems to location-based retail alerts.

Network School

The place that changed
the next ten years.

Why I went

I was at a stage in my career where I felt like I wasn't done. I wanted more. So I put myself outside my comfort zone, got on a plane, and went to Network School in September 2025. I intended to visit. I stayed.

What I found

A community built on “win and help win.” People learning frontier skills in the open and helping each other ship. It literally transformed me. I walked out hugely optimistic about the next ten years — and with the conviction that became Bearing.

“Learn the skills on the frontier. Then engage yourself in the world to help solve real problems. That is magic.

The one tip I'd give anyone right now
Education

UC Berkeley, Haas School of Business

MBA — Economics & Entrepreneurship

National University of Ireland, Galway

BSc (Hons) — Applied Physics

By the numbers
20+
Years in product & innovation
200+
Teams coached & grown
36+
Accelerator programs designed
4
Acquisitions (Google, Meta, Workday, Rakuten)

Ready to see what AI can do for your business?

Start with the free 7 Steps of AI — seven short lessons, no sales call, delivered to your inbox.

Start the free 7 Steps of AI