In the mid-1980s, I was living in LA – working in the rock concert industry, fresh out of college. I’d find short-term jobs as a roadie, or work corporate sponsorship gigs, before being fired pretty quickly.

It was around this time that airlines were launching their loyalty schemes, desperate to secure regular custom. Before, nobody cared which airline they travelled with – it was all about getting the cheapest fare. Frequent flyer programmes radically changed things. By introducing mileage schemes that rewarded travellers with flights and hotels, airlines hoped to build loyalty.

I was paying all this little attention back then. But by the late 80s, work had dried up. One day I was standing in the unemployment line when I noticed an advert in USA Today: fly with United around Thanksgiving, it said, and see your reward miles tripled. Later that week, I read a note on a noticeboard in my apartment building: a local man was selling cheap plane tickets to the east coast for the holidays.

That’s when I had my brainwave. In those days, rules were lax and IDs weren’t checked at airports before domestic flights, so I could have multiple people flying under my name. If I could find cheap fares, and people willing to help me, I could play the system. Of course I’d have to spend money to earn miles, but I could make it worth my while if I did so cleverly.

I soon got to work, learning how each airline scheme worked. The goal wasn’t to spend spend spend, but to use my money wisely. That November, I had 20 people fly under my name. And yes, I spent six or seven thousand dollars, but in one weekend I clocked up 1m points: that was worth 14 business class tickets to anywhere I wanted.

At that stage, I couldn’t make use of my points. I could fly somewhere, but didn’t have the cash to pay for the rest of a trip. When I realised how many miles I could accrue by playing the system, though, I knew I could set myself up financially for the future.

Often I wouldn’t think up a scheme, but take other people’s tricks and grow them. Take the Thai baht run. In 2001, a guy came up with this novel idea. He realised you could fly between two Thai cities for $8 return. If you flew back and forth 100 times, you would be in the top tier of United’s programme.

On Air Canada, I worked out the rewards for that same trip would be even greater. So I hired 20 local people to fly back and forth 100 times for me, also under my name. They were a mix of out-of-season rice farmers and masseuses. I set up their accounts and linked them to mine, managed their bookings, and of course paid them. At one stage, the authorities presumed I was running some sort of drug smuggling ring – until I showed them my spreadsheets brimming with complex mileage calculations.

I’ve always been totally open with everyone about my plots, often booking thousands of tickets in one transaction. I’ve had run-ins with industry lawyers who have tried to intimidate me, to no avail. Over the course of 20 years, I racked up in excess of 40m miles.

My wife was also, at times, less than pleased with me. For years I sat up late thinking up ideas, constantly scribbling down calculations. Occasionally, I’d get her involved. One night – pre-online reservations – we had to book 1,600 tickets over the phone, with a limit of three tickets per call. I’m sure it’s not what she bargained for when she married me.

Back in the 90s, those miles would have easily earned me 500 international business class flights. Over time, however, airlines have taken back the advantage. Points have been devalued; rewards are no longer fixed at a certain price. You simply couldn’t make the calculations now. During my peak mileage earning period, climate change was not a front-burner issue, so it had no impact on my thinking. With what we know now, I’m not sure I’d want to try out some of the mass-buying schemes.

Today, though, my wife and I can enjoy the fruits of our labour: I’ve still got miles in the mid seven figures. This year, we’ve been scuba diving in Egypt and to French Polynesia. My greatest fear is the miles outlasting me: why should my kids get to have my hard-earned fun?

• As told to Michael Segalov

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