My Story

Jamie Sutton - My Story

Hi, I’m Jamie.

This blog is an attempt to be more public with my learning.

I’m interested in:

  • The Toronto Maple Leafs (hockey)
  • Relationships and emotional intelligence
  • Solo travel, minimalism, and language learning
  • Independent learning, autodidacticism, and meta-skills
  • Automation, asynchronous work, and 80/20-ing anything worth doing

Here’s a bit about my background and how I got here:

How I started working online at 17 and what I do now

How A Broken Weedwacker Led to Copywriting

It all started with a burning desire to escape the fate destined for me as teenager in a relatively small Canadian town: becoming a landscaper.

My Dad is involved in landscaping. Some of my best friends are landscapers. One of my brothers repairs landscaping equipment on the side…

But I couldn’t become a landscaper. I liked the internet too much to worry about fueling a weedwacker with the right ratio of gas to oil. (Did you know: you can completely ruin a weedwacker if you mess that up? I didn’t know that.)

After a year of crooked mower lines, uninspired gardening, and a broken weedwacker (I said I was sorry), I stumbled upon a website that would open up the world of making money online.

Seriously… I literally stumbled upon it. Does anyone remember StumbleUpon?

RIP StumbleUpon

RIP StumbleUpon

The website that changed everything for me was an internet marketing forum, where SEO, PPC, PPV, and all sorts of other intriguing acronyms were discussed in detail.

The most intriguing part about this forum was that most users there didn’t want a traditional job. Instead, they were building their own businesses, projects, or side-projects, at the very least.

I wanted in.

I studied the posts on that forum religiously. I was barely 17 years-old, a year too early to open an AdSense account (shh!), but I knew this was the kind of work I wanted to do.

This is where I was introduced to freelance writing, which is still my primary income source to this day—I now specialize in email copywriting and sending excellent text messages to friends and enemies.

I started writing for $0.01/word in the buy/sell/trade sub-forum. And I felt like a rich motherfucker.

You’re telling me that I can sit inside my semi-air-conditioned house, write 500 words about “local dumpster rentals in Arizona”, and I’m going to get paid $5 USD, as long as I mention the keyword exactly 3 times?! – Jamie, 2010

Not long after, I raised my prices to deal with demand. Then again. And again.

Jamie BST - Freelance Writing Day 0

I’m cringing reading this now, but I respect it.

Next, I learned about copywriting: If I learned how to compel readers to purchase products, I could charge higher rates.

This was a BIG deal. It was such a big deal that I took a break from writing.

I wanted to try what my clients were doing: affiliate marketing. I would build my own website, write my own content, follow random SEO blogs, and hope for the best.

It worked. Kind of…

I earned enough money to pay for my college program and cover the costs of living on campus… for 3 months, at which point I dropped out and returned to freelance writing after Google penalized my highest earning website.

Everybody loved my work.

Everybody loved my work.

I wrote about esports. I wrote about cryptocurrency. I made it a habit to find work in whatever industry was on my mind most often, before finally coming back to what I was best at: copywriting.

That brings us to current time. Welcome back.

Today, I work remotely as an email copywriter for Wavebreak, an email marketing agency for 8-figure ecommerce stores. And I’m always chewing on a side project of some kind.

My favorite people, books, all-time best purchases and more

My Favorite Resources

Some of my absolute favorite books, websites, and sources of inspiration.

I will stop what I am doing if these people release new content:

I also really enjoy:

A couple of my favorite books I’ve re-read at least once:

My favorite purchases ever:

  • Private coaching – If you want to get better at something and you’re not living paycheck to paycheck, consider getting private coaching.
  • A kettle with adjustable temperature controls. Green tea is ready in a couple minutes and perfect drinking temperature 1-2 minutes later.
  • A home gym. I bought a squat rack, bench press, and 500lbs of Olympic plates, years ago. I didn’t prioritize exercise until recently, but it’s still one of my all-time best investments.
  • Google Pixel 3 (phone) – I used an ancient phone for more than 5 years, mocking my friends who upgraded every year. Then I started traveling. Having access to memories in high quality is now priceless to me.

Some of my favorite quotes:

  • “Action expresses priorities.”Gandhi
  • “Love is three quarters curiosity.”Casanova
  • “It looked good … it might be good… he was not sure. He had no one to ask.”Ayn Rand, The Fountainhead
My favorite services, software, tech, and travel gear

My Toolbox

Here are some of my favorite gear, services, and tools I use on a regular basis:


  • Readwise – My Kindle highlights live here.
  • Instapaper – The prison where my ‘read later’ collection suffers.
  • 1PasswordX – You need a password manager. This one is my favorite.
  • HEY – Privacy-first email service from the Basecamp team.
  • Standard Notes – Privacy-first note taking app for my most personal thoughts.
  • Number Barn – Park your phone number here and get all your texts as emails. Useful when traveling.


  • Keypirinha – This is the best. There’s a learning curve, but it’s worth it.
  • PatchMyPC – The easiest way to keep your software updated.
  • Greenshot – Simple screenshots and annotation.
  • Veracrypt – Encrypt your drives!


Travel Gear

The inspiration behind this blog

My Inspiration

This blog was inspired by Nat Eliason, David Perell, Taylor Pearson, Steph Smith, and David R. MacIver, among others.

My newsletter: Proof of Learning

My Newsletter

In May 2020, I started a weekly Tuesday newsletter called Proof of Learning.

Proof of Learning is an occasional recap of my (not so) intellectual curiosity.