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The founder

I've built this twice. Simma is the third time.

For twenty years my job has been the same one: replace a pile of disconnected systems with one platform. First for the media company I started with my father. Then for a FTSE 100 global events company. Simma does it for every small business, and I built it myself.

Technical founderCo-founded a 40-person media businessFull-time from first close
Paul O'Connor, founder of Simma
Paul O'ConnorFounder · Simma Labs Limited · Loughborough, UK LinkedIn ↗
I've run the businesses Simma is for

"CRM in one place, email marketing in another, files in Dropbox, payroll in IRIS, and half the team locked out of half of it to save on licences."

My father and I started Rail Media as a newspaper. He ran sales; I ran product: I launched RailwayPeople.com, built the technology and started the events business. As Managing Director I ran it at 40 people and doubled its revenue. I sold iStudio Publisher to its developers for a 50% revenue share. Then I founded Workwear City, an online store with 22,000+ products, and sold that too. The problem Simma solves is one I paid for, every month.

What running my businesses looked like
8logins
1login

An instructor has the same eight today: TeamUp, Squarespace, Mailchimp, Canva, Google Drive, Xero, WhatsApp, ChatGPT. The problem →

The same idea, three times. Each time for more businesses.

2012 – 2017 · Rail Media

Datlyn

For one company

One system as CRM, subscriptions, event management and sales tool — replacing a set of point solutions and automating the company's growth.

2021 – today · A FTSE 100 events company

One events platform

For a FTSE 100 company

Head of Product for event platforms: a 50-person team, 2,000+ live sites, and 386 sites moving from three content systems onto one platform.

2025 – today · Simma

Simma

For every small business

One system for website, email, customers, bookings and money — with an AI team built in to help the owner run it. Built solo, in production.

The record

Twenty years of product, and two businesses sold.

50people led at a FTSE 100 company, across three squads
2×revenue as Managing Director of Rail Media
1m+monthly users on RailwayPeople.com, which I launched
2businesses sold: Workwear City and iStudio Publisher
  1. Rail MediaWith my father from day one, starting as a newspaper. Launched RailwayPeople.com; co-designed iStudio Publisher, $100k a month in sales, and later sold it to its developers for a 50% revenue share.
  2. Product DirectorBuilt Datlyn. Grew RailwayPeople.com to £100k+ a month in SaaS revenue.
  3. Managing DirectorA 40-person media, events and SaaS business. Revenue doubled.
  4. Workwear CityFounded an online store with 22,000+ products. Sold it in 2021.
  5. A FTSE 100 events companySenior Product Manager, then Head of Product: 2,000+ sites, $100m+ a year in ticket sales, an AI programme.
  6. SimmaBuilt alongside the day job; in production since September 2026.
Why now

I built it because I wanted it to exist. AI made it urgent.

01 · ON THE SIDE

Built properly, for its own sake

Simma started as the platform I always wished my own businesses had had: one record, every tool, nothing rented. I built it in my own time, with no customers to please and no shortcuts to take, and with a quiet thought that one day it might become a company.

02 · THEN AI ARRIVED

The foundation became the point

AI agents are only as good as what they can see and what they're allowed to do. The new "AI operating systems" bolt on to rented tools. Simma already owned the whole business: every customer, booking, pound and message. It's the context an AI team needs.

03 · SO, NOW

The time is now

The window for small-business AI is opening this year, and the foundation it needs is already built and in production. That part can't be shortcut. The raise turns a platform built on the side into a company with customers, and makes me full-time.

"I wasn't building an AI company. I was building the right platform. Then AI turned the right platform into exactly what agents need."Paul O'Connor
The team

Partners first. Proven people as it grows.

I'm the technical founder. The raise pays for me full-time and two employed Local Partners, who win, launch and look after customers in their areas. I train them on Simma so they can train customers. The senior people come later, as the next round funds them.

From first close

Me, full-time

Product and engineering, and selling to the first customers by hand. No co-founder: the platform is already built, by me.

Already working

Coding agents

They take work from Simma's own board, change only what they're allowed to, and check back in. Every change is recorded against the task.

Measured on Status →
In the budget

Two Local Partners, then engineers

  • Month 3Local Partner #1
  • Month 4Local Partner #2
  • Pre-seedLocal Partner #3 and the first engineers

If something happened to me? Today that's a real risk. Until the pre-seed it stays a real risk: two engineers join in month 8, one owning infrastructure and releases, so from then three people know the platform, and the decisions and the full history of the build are written down and kept with the code, where the next engineer can read them.

The bench: people who've asked to join.

Eight senior people I've worked with for years. Each knows Simma, has talked it through with me, and has asked to join. Nothing is agreed in writing, and none of them is in the first round's budget: they're how Simma grows after the next round.

Head of Engineering

Runs engineering today on a platform with 100 million views a year. We worked together for many years and think the same way.

Engineering
Head of Sales

A decade in tech sales, now selling to enterprises for a well-known brand. A friend since primary school.

Sales
Customer Success

The best people person I know: someone who genuinely cares whether each customer succeeds.

Customer success
Head of Marketing

The best marketer I've worked with. Data-driven, and brilliant at getting the right message to the right audience with the right call to action.

Marketing
Product

A data-led product manager with a growth mindset. The person to turn usage into momentum.

Product & growth
Operations

We've run multi-million-pound projects together. The most organised person I know, who sees around corners and plans for everything.

Operations
Creative

Years of building brands together. We push each other's ideas further and make brands people feel.

Brand & creative
Content & Media

Previously an editor on one of my magazines, and the person to launch a printed magazine for UK business owners.

Content & media

Unnamed for now, as each is still in a role of their own. Half of Simma is marketing, and three of them (marketing, creative, and content and media) are the people to run the marketing machine. See the plan →

Later, larger customers. Within five years, the ambition is dedicated teams for mid-market and enterprise customers: sales, product, implementation and customer success, with the security and governance those buyers expect. It's an ambition gated on the earlier milestones, and its costs aren't in the current model. No advisers yet: the franchise conversations are with an industry contact.

The raise is what makes me full-time. Here's the plan.