About
An operator who builds the system, not just the slides
Years of doing the work, a lot of it from the road. Here's the path that led to building AI operating systems for real businesses, and the point of view that came out of it.
The background
From a one-way ticket to building AI operating systems
The short version of a long road, and why it shapes how I think about AI in a real business.
- 01Business school
A one-way ticket out of the classroom
I spent the final semester of my business degree abroad and caught the travel bug. The standard path of desk, commute, and stay put was never going to be the one.
- 02First role
Agency account management
Back home, I started in account management and business development at an agency. That's where I learned how client work and growth actually run day to day.
- 032020
Laid off, then all in
A pandemic layoff pushed me to go all in for myself: freelance copywriting, email, and automation. Years fixing the human version of copy by hand trained my eye for what doesn't sound like a robot, which is exactly why the systems I build now still sound like you.
- 04Nomad years
Running the work from 28 countries
Jess and I went nomadic. Every workflow had to be async, documented, and able to run without me in the room. That constraint became the methodology: if a system can run from anywhere, it can run anywhere.
- 05Pre-ChatGPT
AI-early in marketing
Five years working AI into marketing and ops for startups and online businesses, writing SEO content on GPT-3.5 before ChatGPT made it a category. The foundation under everything I build today.
- 06Now
Re-rooted in Toronto, building Digiwell
I ended the nomad chapter to be closer to family and friends, and to build the AI systems business for real.
- 072026
A packed Toronto Tech Week workshop
My 'AI Fundamentals for Founders' workshop at Toronto Tech Week drew 150+ registrations and 118 attendees at George Brown's Harbourfront campus. Six months of cold outreach hadn't moved the needle. One workshop rebuilt the authority.
In their words
What people say after working with me
“Trevor has been a huge asset across multiple companies in our portfolio for more than three years. He turned messy content and newsletter processes into smooth systems that now run reliably with sharper messaging and better results. If you get the chance, I highly recommend working with him.”
Scott Oldford
Investor, mentor, and coach
“It's a breeze to work with Trevor, he totally gets the space and messaging, has a brain for marketing, and writes really really well. I would highly recommend Trevor for all of your marketing needs.”
Dave
Co-founder, Breakthrough Academy
Want me in the room?
Podcasts, stages, and workshops. Tell me about your audience and I'll bring the angle that fits.