A few people have asked me how I got started in blogging and apps. And so here’s the brief story. Well, as briefly as I can be bothered…
Before Discover Discomfort and the umbrella company we formed around it, Disco Media, I had dabbled in startups and apps.
I had previously launched a watch brand, Eureka Watch Company, in 2016 as kind of an “experiment”, and then shut it down prematurely because I thought it wasn’t doing well (it was doing fine, I just was impatient). I had also dabbled in a few other businesses, including a custom lingerie brand (which my partner went on to build to something much bigger), and even launched my own app, Pilgrim Coffee (here’s that story).
All of these were fun — but were really just dabbling. So here’s the story of how I got started.
My Last Job — Lyft
Pilgrim Coffee was fun. It was working — I was getting users and engagement. But it was hard work (I was coding and marketing, and not that good at either), and I didn’t have a clear path to revenue.
When I got divorced, I didn’t really want to look at things I was doing “pre-divorce” anymore. So I got a job and moved to the US — to work for Lyft. This would be my last — I hope — formal venture into suit life.
At Lyft, my job was something like a corporate hitman. My title was literally “Special Ops Manager”, something they made up to lure people like me in. In reality, this meant they just wanted to hire smart, adaptable people who could do projects with little guidance or supervision, which is a way of working I love, anyway.
I had a lot of fun at Lyft. I enjoyed the autonomy. I made a ton of friends. I made decent (not great) money. And I even met my partner. Things were going well for me there. I was well respected, well-liked, and was getting raises and promotions. I even won an award.
But still, I wasn’t really satisfied. The best parts of my day were the motorcycle ride to and from work, and the run I’d do at lunch with a weighted vest, doing push-ups and pull-ups off construction equipment along the San Francisco Bay. The rest was just usual work: meetings, presentations, and meetings about presentations at other meetings. It was dull work with good people.
Every day, I’d go to CrossFit at 6 am, have a shower, blast on my motorcycle to work and park. I’d give one longing look to my Ducati Monster, knowing I wouldn’t see it for another eight hours. Then, I’d give the best hours of the day to someone else, helping them realise their dream, and making them richer. Finally, I’d come home, scarf down a dinner, and get ready to do it all again.
I was making good money — not developer money, but I wasn’t poor. I could easily afford my rent, simple motorcycles, an expensive gym, and going out sometimes.
But the crazy thing was that I was saving almost nothing. I didn’t live an expensive lifestyle. I had a motorcycle, but it cost me around $5,000 all in. I didn’t travel a whole bunch. And yet money didn’t accumulate in my bank account.
The Apocalypse of San Francisco
On top of this, San Francisco kind of sucks. I was there pre-pandemic, and it was already rife with problems. A spiralling cocktail of homelessness, mental illness, and drug use meant that in the middle of town I’d frequently encounter things like parking lots littered with syringes, people hurling obscenities at the top of their lungs at 4 am, and people defecating in the middle of the street in broad daylight.
The price we had to pay to live in this inferno was hellish. In my first two years, I paid around US$2,000 to share an apartment in the Mission with one other guy (it was $4,000 total). After that, I side-graded to a 1-bedroom apartment in the Inner Sunset area for US$2,800 a month. This was a good chunk of my take-home salary. (Luckily, I was sharing the one-bedder with my partner.)
Besides the rent, there were many other ancillary costs to living in San Francisco. Traffic was terrible, and the public transport system sub-par. Prices for everyday goods were high. And crime was through the roof. On average, our car would be broken into five times a year. It was usually when we had to park on the street, something we couldn’t avoid at times (e.g. when visiting people).
San Francisco has actually gotten worse since the pandemic. Who in their right mind would pay through the nose for a one-bedroom apartment in such an apocalyptic city? Fewer and fewer people, actually. People have left in droves.
So, given this context — not saving any money and living in an objectively terrible city — something had to give. My partner and I decided to leave. It was bittersweet, as there was much to enjoy about Lyft — as I wrote in my goodbye letter.
But something beyond was calling. In my coffee breaks at work, I’d often see people in cafés on laptops, wearing skinny jeans or athleisure. I always wondered what they were doing. Well, I wanted to stop wondering, and to become one of them.
Choosing Blogs (and Apps)
We chose blogs through a process of deduction. Yes, I had some history with apps and websites, but we did an open-minded examination.
We started with what we wanted our lives to look like. This was straight out of Tim Ferris’ Four Hour Work Week, a book I think is best for mostly the first few chapters.
In those chapters, Tim asks what you’d like your life to ideally look like in the near future and the far future, and to use those as goalposts towards which to move.
We thought about the times we were happiest in our lives: when we were travelling to places where we didn’t speak the language, immersing ourselves and learning to get by. I was so confident that this was what I wanted that I literally turned down a $1,000,000 job offer for something that was previously my “dream job”.
So we decided that our criteria were:
- Online businesses only — No fixed assets
- No e-commerce (it’s a headache of product inventory management, returns, and customers)
- No “trading time for money” — no teaching online, etc.
This gave us a raft of options. Things like apps, software, courses, affiliate marketing, and so on.
We had a brainstorming session and stuck a bunch of sticky notes on the wall. To be honest, I don’t remember what many of the below mean!
Some of our leading contenders were
- A service to help with final round interviews (which in big companies for management positions often involves a presentation)
- A website to help people start eyelash extension home businesses
- A course of some kind (I don’t remember)
“Blogs” was an intriguing one. We didn’t know how blogs made money. We looked into it and learned that they make money through ads and affiliate marketing.
But how much money? This was a difficult question to answer. Luckily, many blog vendors had started to sell “How to get started in blogging” courses and so had taken the interesting measure of publishing their revenue online. Very interesting indeed!
We started collecting the data from a number of these sites.
Based on these, I started to get pretty comfortable that we could earn $20-30 per 1,000 sessions. So if I could get to 100,000 sessions monthly, we’d be on $2-3K per month, which would be enough for self-sustaining travel — though not with any level of luxury.
We did consider a few of the other businesses. But blogs had a few points that were attractive.
- They’re easy to start, with low capital investment. Sure, we didn’t know anything about the technical side, and didn’t understand SEO (one never truly understands it…)
- I like writing
That’s it, really. Apps are hard to make and competitive. Courses seem passé. So blogs it is.
The rest, of course, is history — though history still in the making. Our online business has very much not gone to plan — but it also has taken us to places we didn’t expect. I think the one year review encapsulates the craziness of it quite well.