He has handed the day-to-day reins to the next generation - his daughter Abby - but Manawatu businessman Simon Taylor still plays a guiding role at the company he founded in 1995, Fleetwise.
Formerly owner and dealer principal of several motor vehicle franchises, he reckons he could be described as unemployable but that's the beauty of running your own business - you do the hiring.
With several serious contracts signed with major government-funded bodies, including MidCentral District Health Board, and another Pool Vehicle Booking System pilot going live this month, many big fleets are now also Fleetwise.
Why did you become an entrepreneur?
Probably by necessity, in hindsight I was an appalling employee. While demonstrating good strengths in areas, my weaknesses were generally the areas highlighted in performance reviews. A lot of people like me struggle with consensual decision-making. We see it, rightly or wrongly, as slowing progress. I remember clearly a high-profile business friend declaring that he "didn't truck with committees, ask a man with a watch what the time is and he'll tell you but ask a man with two watches and he's not sure". His venture crashed and burned, unfortunately. It taught me to listen better and accept criticism more readily but it's all a little unnatural and I still have the tendency to be a bit of a one-man band if allowed.
What have been the biggest obstacles in running your companies?
Getting the right people and ensuring that they share the vision and work to their potential. It's a rare commodity and once found should be nurtured. I have tended to get ahead of staff with a vision for the company model and relied heavily on trust, often sacrificing communications. The unfortunate by-product here is when that type of confidence is established and relied on, liberties can be taken. Find out what your staff are thinking and feeling as often as you can.
Do you have any tips for budding entrepreneurs?
Certainly, keep hold of your dreams, believe in your concepts and if any self-doubt or boredom sets in along the way, drop it and move on. Total belief and commitment are essential.
What have you sacrificed to be an entrepreneur?
Nothing really, because I'm not made any other way. Peace of mind and total security are nice-to-haves but boring, and I'd sooner find something to test me, something to risk and put me back on the edge. We're all made differently.
Are you prepared for failure?
Who is, fully? And what constitutes failure? I know many fellow entrepreneurs whose business models have commercially failed, but at least they had a go. Is that successful failure? I personally don't do failure, touch wood, but I'm sure there are times when my stable and cosy accountant thought I was sailing too close to the wind.
Who is your "business guru" and who do you admire and why?
My daughter Abby, who runs Fleetwise, is one of the best I've seen. There is plenty of me in her, but more. She's certainly not frightened to challenge, which is healthy and she's had a better, more rounded formal education, she works hard, knows the business and it's widely held that she is now - unquestionably - New Zealand's leading expert on vehicle fleet management matters. She is the "guru" of vehicle fleet optimisation and utilisation. I enjoy supporting her as the new generation of professionalism in this field.
What would you do if you weren't running your own business?
I would probably be musing on where the hole in the market was to start another one.
What do you do in your downtime?
I spend a lot of time at home, creating an environment in which one can relax. I love art and design and enjoy finding inanimate things I like to live with. As a full-on people person I have to have a rest from people also and find that time therapeutic.
What has been your biggest disappointment since you started your business?
Knowing that you've created a solution that will genuinely save a client prospect time and money but for some reason, either personality or otherwise, the door remains firmly closed.
Do you feel better off than at this time last year?