I'm Wayne. Pull up a chair.
I’ve been managing my own portfolio for more than 25 years — through dot-com, ’08, COVID, and 2022. I’m not a financial advisor. I’m not a YouTuber. I’m a guy who got tired of weekends spent on research that AI can do in ten minutes — so I built the tools I wished existed.
This page is the longer version. Coffee optional, but encouraged.
my own money
(by design)
isn’t this
I built the system I actually use on my own money. Every prompt. Every framework. Every page.
The honest version of "why DW exists."
Sometime around 2001, a younger version of me decided I’d manage my own portfolio. I read everything. I made every beginner mistake. I lived through the dot-com bust six months later, then 2008, then a long stretch of figuring out what kind of investor I actually was — versus what kind of investor the financial industry wanted me to be.
I never did become a financial advisor. My day job is in tech — running national vendor relationships for a large distributor in Toronto. That has nothing to do with this site, and is exactly why this site exists. Every weekend I’d spend hours on research — screening, comparing, rebalancing — using tools that hadn’t really evolved since 2005.
Then in late 2024 I started using AI for the analytical work. Not for predictions, not for tips — for the structured analysis I’d been doing by hand. The result was a kind of quiet revolution in my own process. What used to take a Saturday now took a Sunday morning coffee.
Held through the crisis. Learned more in 18 months than the prior seven years combined.
The COVID drawdown. Discovered the difference between knowing your risk tolerance and actually feeling it.
AI changed the workflow. Tested every prompt on real holdings. Started writing them down.
DW launches. The system, packaged. So you don’t have to spend 25 years figuring it out.
Deliberately Wealthy is the system I actually use on my own money. Every prompt was tested on real holdings. Every framework came from a real decision I had to make. I built it because I couldn’t find it anywhere else — and I figured I’m probably not the only one.
The whole site is built on one promise: conflict-free education for people who already know the basics. No affiliate kickbacks. No managed accounts. No “what to buy this week.” Just tools you can actually use, from a fellow investor who has skin in the game.
Things that aren't investing but will probably come up
If we ever end up at the same dinner, the conversation will drift here within an hour. Fair warning.
Chelsea FC
Nottingham Forest
Old-Time Radio
Disney World
Caribbean Cruising
Reggae
Sunday mornings, vinyl, coffee. Beyond Marley. Way beyond.
Investing (obviously)
Family
Six things I'll always do. Six things I'll never do.
- Test every prompt and framework on my own portfolio first
- Show my work — including when the work is messy
- Update tools when they go stale, and email you the updates
- Answer reader email personally (eventually — see Contact)
- Answer reader email personally (eventually — see Contact)
- Stay conflict-free. No kickbacks, no sponsored content
- Tell you when I don't know something
- Give specific advice on your specific portfolio (no licence, no exceptions)
- Run affiliate links to brokers, AI tools, or anything else
- Send "stock pick of the week" emails (they're not how this works)
- Build a LinkedIn presence for DW (it would compromise my day job)
- Sell a product I haven't used myself for at least six months
- Pretend I'm a financial advisor or pretend you should treat me like one
Currently thinking about.
The Psychology of Money — Morgan Housel
The Workbook v1
Alternative asset managers
APO, BN, KKR — the public-private convergence story is one of the most interesting in markets right now.
Paris & Barcelona, July 2026
Family trip. Already optimised the lounge stops. Possibly over-optimised.