What I did in 2019 (my yearly review)

Another year goes by, and another decade, and with it comes the yearly reviews.

I don’t think I’ve done a recap for a long time, but this year was a good one for me and putting it down in writing helps me to see the bigger picture and how the efforts I make will compound and continue to grow over time.

Sabbatical & job quitting

I hit the 5-year mark at Automattic and WordPress.com in December 2018 and one of the many benefits of that job was a 3-month paid sabbatical. Through clever use of my Christmas time off, I managed to finish work around December 20th, with a view to going back to work on April 1st.

During the sabbatical I:

  • Fixed up my office with new flooring, new dog-proof paint, and a new desk
  • Bought, used and subsequently sold a gaming PC and monitors
  • Bought one ultrawide monitor
  • Did a lot of yoga
  • Rode my bike
  • Broke my bike
  • Fixed my bike
  • And much, much more

I learned a lot about myself during the sabbatical but the most important takeaway was I would never be truly satisfied with my life whilst working for somebody else.

Ask my wife and she’ll tell you that I HATE being told what to do. It’s almost to the point where I will do the opposite of what I’m told, just because I’m told to do it. Even if it’s the right thing to do.

Now, Automattic didn’t really “tell” you to do anything. It’s probably the absolute best possible gig I could ever find. But I was still working for somebody else.

So, after much deliberation, I quit before my sabbatical ended. In doing so, I missed out on a trip to Costa Rica, but that will be rectified at the end of this month. I will see those damn sloths!

I’ve missed the people I worked with this year, but it was 100% the right decision and I’m now free to explore my creativity and build my wealth in a way that working for a salary will never allow for.

Building humble internet businesses

The businesses I’ve worked on this year are humble. They are simply built, simply run and generate dependable revenue and profit.

We’re not trying to swing for the fences and dominate a market. We’re not looking to get funding and scale operations. We’re not trying to innovate.

What we ARE doing is providing products people want, at a price they are willing to pay for it.

I’ve definitely been triggered by people on Twitter this year because so many of the discussions around revenue, markets, and scale are from a software/SaaS perspective. We don’t do that.

Here’s what we do:

  • 15m+ pageviews across six membership sites
  • mid-six-figure revenue ($)
  • 80-90% profit margin
  • fully outsourced customer support
  • fully outsourced content/product creation
  • thousands of happy customers

What I find most impressive about the scale of our operation this year is that our primary customer is elementary and high school teachers.

Trust me when I say that it’s like getting blood out of a stone selling to them! It’s a true testament of the products that we’ve built that they are finding the budget to purchase them when so many teachers are overworked and underpaid, often funding the purchase out of their own pocket.

Buying and selling

In addition to the core business, we also did some pretty impressive wheeling and dealing as well.

We bought a network of ~60 websites in September for low-mid six figures at a very decent multiple.

What I’m most proud of with this purchase is how quickly we were able to get the capital and make the purchase. So many buyers get a due diligence checklist that is dozens of pages long and work through them one-by-one.

Our process is much more straightforward:

  • Do we know/trust the seller?
  • Can we verify the organic search traffic?
  • Are there any potential risks?
  • What is the potential for growth?

That last one is important because I think one of my primary skills is in seeing the potential for growth in an existing asset. These sites were not being grown and had so much potential that we HAD to get the deal done as soon as possible.

Of the sites we bought, three of them were incredible, and one of them, in particular, is a site both me and Ryan have coveted for years: Nine Planets

It quickly became apparent that taking 60+ content sites and migrating them all to WordPress, producing content schedules for each, and then outsourcing the content itself, was going to be a huge task.

Added to that, a lot of them were very niche and not likely to grow at a rate that made it worthwhile investing in.

We reached out to an advertiser who had wanted to buy the sites before we did the deal, and we agreed to sell all but the three sites we really wanted.

One final sale

There is one more deal that we didn’t manage to complete in 2019. All of the paperwork was essentially done, but we ran out of time to sign the contracts before the Christmas/New Year break.

Personally, I blame the lawyers and their archaic back-and-forth Word document revisions.

I’m not sure how much I’ll be able to talk about the sale when it goes through, but it’s our primary asset and I think it’s a good deal for both parties.

I’ll probably write a post about the generalities of why we decided to sell but, for me, the time value of the money was the primary motivator.

Having the next x years of profit in cash right now is more valuable and useful to us as we look at alternative ways to compound our wealth.

Health and fitness

When your wife is a yoga teacher, you’re obligated to do it, and I actually really enjoyed a daily practice, especially during my sabbatical.

Yoga helps to calm my mind and forget about the to-do list.

I also did a 90-day “SIX PACK REVOLUTION” plan and lost 5kg of fat. Yes, I did get a six-pack. No, I won’t show you. Yes, I did lose it over Christmas.

I started lifting weights again for the first time in 2 years after tearing my rotator cuff and turning to bodyweight and yoga exclusively.

Like anything, fitness is pretty simple. You know the steps to get in shape, but maintaining the habit and showing up every day is the true secret.

During the six-pack fitness program, we did pushups and squats daily, eventually up to 170 a day. It became a battle of the mind and dropping down to do sets of 50/40/30/20/10/whatever even when you really didn’t want to.

Travel etc

Since leaving Automattic I haven’t travelled as much as in previous years BUT when I have travelled it’s been with family – which is more fulfilling.


10 days of all-you-can-eat madness.


No kids, no selfies, but lots of eating, drinking, and cat cafes.

Kattencafe Kopjes

Download Festival

The kids definitely enjoyed rocking out in the rain.

Ultimate Strongman

Flexing on the World’s Strongest Man, Martins Licis, and the legendary Big Z.

Here’s to more fun in 2020.