Greg Bruce finds it hard work - and costly - to become passively rich online.

I must have been having one of my occasional massive panics about my general lack of money, because one Saturday afternoon earlier this year I found myself listening to an episode of a podcast called "Smart Passive Income".

A little part of me has always wanted to be rich and a bigger part of me has not wanted to have to work for it, so the title alone was very attractive to me.

After listening to that first podcast, I began to read through related online information about how to generate a passive income, of which there is much, and to download free e-publications, of which there are many.

What the podcast and related online information suggested was a roadmap: You start a website, give away lots of great, free "content", and save up your "best stuff", for which you charge "megabucks", or you find other ways to make money from your large audience, like online sponsorships, or consulting, or speaking gigs, or publishing deals.


The more I read about it, the more obvious it became that to get to the point where you're receiving a passive income actually requires quite a lot of activity.

Generating lots of useful content is, in itself, far from a passive act. Our world is already awash with content. What could I come up with that would set me apart? And that would only be the first step. After that, there would be marketing it, finding an audience, building an email list, search engine optimisation, email optimisation, social media campaigns, A-B testing, figuring out how to monetise, and all manner of other rabbit holes of non-passivity.

Nevertheless, the pull of the money-making impulse was strong enough that I didn't care. I started to "work up some content" and started broadening the scope of my money-making research possibilities beyond the strictly passive. I started studying the successes of world-leading entrepreneurs. I started to dream big. My plans became ever grander.

I would drive past expensive-looking houses in expensive areas and think, "I'll probably own that one day." If mindset was important, I had it, and anybody who's anybody in the entrepreneurship game will tell you that mindset is important.

When I saw my friends, I would run my latest ideas past them, ask them for feedback and ideas of their own, and generally shut down any other avenue of conversation. Instead of scrolling emptily through my social media accounts in the 15-20 nightly minutes it took to get my 18-month-old to sleep, I started using the time to brainstorm.

"When did you catch capitalism?" my rich brother asked me one day. That was probably the first time I thought of it as a disease.

For a good few months, my obsession raged. I read several books on entrepreneurship and took three separate online courses. I became a disciple of the "lean startup" movement. I drew up rudimentary business plans on a blackboard at home.

What I didn't do, in all that time, was take any action.

I had started too grand, become too ambitious too soon. I needed to start small, get my feet wet, walk before I could crawl. I went looking for opportunities with low-set up costs and I discovered Fiverr, a site where you can offer various services to the people of the internet and charge not much for them - as little as $5.

I thought hard about the intersection of what I could sell and what people might want to buy. I can write and not much else, and after thinking about it for a while, I concluded that the thing people want written more than anything else is online dating profiles.

I set up my basic bio on Fiverr, then hung out my shingle. I wrote: "Research shows that the quality of your online dating profile has a massive effect on the quality of dates you go on. Actually, I've got no idea whether research shows that, but surely, right?"

I thought this was funny, but the market didn't respond with either amusement or interest. I tried to meet the market with rewritten blurbs and new pricing, and I even put up new profile photos, including a great one of a lissom, silhouetted couple walking on the beach, but I just couldn't get any traction. A handful of people viewed the ad, but nobody ever contacted me about it.

I dropped the online dating thing and started offering to write love poems, then love poems written in calligraphy, then funny lists for people's websites. None of it made an impression. Barely anybody saw my ads.

Maybe, I thought, I just need to get some money - any money - coming in, to kickstart things. "Money begets money", that type of thing - the sort of phrase I imagined appearing in a self-help book, and I know a thing or two about self-help books.

I went through my bookshelf and picked out three of my highest-value self-help classics: The 7 Habits of Highly Effective People, The Artist's Way and Eat Pray Love. I also found an adult-size kangaroo onesie in the wardrobe and a brand new unopened neck pillow that had been given to my wife by someone who obviously didn't like her. Then I listed the lot on Trade Me.

When I told my brother about this new plan, he said, "Do you think that buying things retail and then selling them at a discount is a sustainable business model?"

He had a fair point, but you have to start somewhere and, as with anything in life, once you strike out in a certain direction, things often start going your way.

For example: on hearing that I was selling stuff on Trade Me, a friend gave me a copy of Madonna's famous Sex book, that she had been wanting to get rid of. It came complete with the original wrapping and seemed like it would probably be worth something.

Then my wife told me one of her friends was a big op-shopper who was making significant profits by buying underpriced stuff and reselling it on Trade Me, and she would be willing to take me shopping.

Things seemed on the up and up.

But I was too embarrassed to post the Madonna book on Trade Me. Then, after weeks of trying to organise an op-shopping trip with my wife's friend, she had to pull out of our planned shopping expedition when one of her children got sick.

I asked her if she could give me some tips so I could do it alone, but she told me it's something you can only do profitably if you really know your subject - car parts, say, or old pottery, or her own area of expertise (kids' clothes). I had no expertise.

My five Trade Me auctions closed with a total income of $35. Eat Pray Love attracted no bids.

There must be, I thought, a guaranteed, no-risk, no-fuss way to make money online, and so it proved. It's called "matched betting" and it's the number one ranked technique on's "40 easy ways to make money online and offline guide".

Basically, because online betting sites offer occasional free bets, especially to new members, you can join such a site, take their free bet, and place it on, say, the All Blacks to win, then go to another online betting site and place a matching bet for the All Blacks to not win. You're guaranteed to collect on one of the bets and, because you've paid for only one, you're guaranteed to come out ahead.

I found a list of betting sites offering free bets for new members and I signed up for one, depositing $10 in my account. But no free bet appeared on my account. Then, when I read the fine print, I found out that they are available only to residents of the UK.

I didn't interact with the site for a while, then forgot my password. I thought about trying to get my money back but it seemed quite hard and a combination of shame, guilt and fear prevented me. Online gambling entrepreneurs are savvier than me. Nothing is no-risk.

A couple of months ago, shortly before the birth of my third baby, I made a semi-conscious decision to not focus my attention on money-making ideas until at least a couple of weeks after his birth. For the first few days, it was pretty hard, but after that, it was really very easy. I was surprised by how little desire I had to go back to it.

I ran the idea of it through my head a few times, just to see how it might feel, but the urge had totally gone.

Two months later, as part of my proper job as a journalist for this publication, I attended a midweek evening event, which was populated mostly by bright and enthusiastic entrepreneurs. By the end of the night I had found myself completely drained by the experience: all the striving, networking and self-promotion.

At home, I told my wife that I hadn't enjoyed it, and that I thought the reason was because the people at that event weren't my people. She laughed and replied that until a couple of months ago, I was those people. I thought about that statement. It was complicated, because there was clear evidence of my months of striving to suggest she was right, but then there was also the quite concrete evidence of the fruits of that striving: $35 in my pocket, less $10 lost to a foreign gambling site, that suggested she was quite wrong indeed.