Mike Rudd was an online dating entrepreneur before digital entrepreneurs were even invented.

Michael Absolum was my best mate back in Otahuhu College. He is now the director at Evaluation Associates in Auckland (and he’s still my best mate). Age 17, Abbo and I shared a vision of great commercial success and all it would bring us. We were optimistic, but a little short on detail. We worked weekends and school holidays building commercial glasshouses under the kindly and clever tutelage of George Hoskins. George had competed honourably for New Zealand as a middle-distance runner in the Helsinki Olympic games in 1952.

Acquiring some building skills, physical strength and a whiff of what a successful small business looked like, we widened the net with an ad in the South Auckland Courier stating: “No job is too big or too small.” This ambitious approach brought in a decent number of responses, most of which amply demonstrated that our maximum scope was mowing lawns and trimming hedges.

Then we had a brainwave. I was studying mathematics at Auckland University and Michael was studying psychology. Computers were the latest, sexiest technology in town, so we budding entrepreneurs combined these factors and established the first New Zealand Computer Dating Bureau in 1968. It was actually a smash hit and we got quite a bit of PR. The Auckland Star ran a feature in the newspaper, and we arranged a date for a lovely young reporter, which was covered by national television.

Our questionnaire ($1 per date) explained that the profile-matching had been devised by our team of qualified psychologists and that the results would be handled by similarly qualified statisticians. The computer side of things we rented by the hour from something with less capability than a poor smartphone, which filled a house. Each query took all night to process and resulted in tens of metres of printed paper. All fine, until the New Zealand Consumers’ Institute wrote to us asking: Who were the qualified psychologists and mathematicians? And where were our registered offices? We ran a mile and closed down, terrified by the sudden appearance of authority.

We should have backed ourselves to answer the questions clearly, confidently and with a degree of chutzpah, like I’m sure many of the entrepreneurs who I enjoy reading about within these pages would do.

The early enthusiasm which fuelled Michael and me was squashed not by bureaucracy or obstacles, but by our own lack of conviction. Confidence is not about expecting everything to go right, but about knowing that when it doesn’t, you can handle it.