Derek Handley. Photo/supplied

Are entrepreneurs born or made?
I’m convinced that if you surround yourself at any period in your life with the right people, environment and encouragement, you can become an entrepreneur. Entrepreneurship is hard, whatever it looks like on the outside. You really have to want what you’re doing to get past the barriers and pitfalls.

In your book, Heart to Start, you write: “Break a rule. Fix it later.” At 16 you were selling knock-off games; in your twenties you borrowed to make money on shares and tried to start an online betting site.
As long as you’re not breaking the law, I think what I’m referring to more is convention and paradigms. When you’re younger – and you can be young for quite a long time – that’s a natural element of youth: being braver to do that. It’s one way of learning very fast, both the good and the bad. As long as you can get up off the floor and continue, it’s definitely a technique to exercise at certain times in your life.

[With the online gambling site] there was still an enormous amount of grey area in what was the lay of the land. The grey area is often where the most groundbreaking things are taking place. Laws, especially in technology and innovation, lag behind pioneering individuals and organisations that try to push the boundaries. That’s a large part of technology’s role in society – it gets ahead of the current framework.

You lost a lot of money at 22. Are setbacks like that the making of an entrepreneur?
It wasn’t so bad because I had good friends. I had to work my way back from a minus-six-figure starting point before I’d even basically entered the world. I knew enough about money and work to know there was no solution other than to create a successful company to pay back the people I had borrowed the money from.

What makes a good entrepreneur?
It’s not different to what makes a good leader in a lot of aspects. The vision is No 1. What does the future look like? And that drives along people to believe you, your customers, your staff, your partners. The second thing is the persistence to carry through a path while there are continual barriers being put up. The third thing is the ability to convert that vision into actual action.

Sometimes you get [all] that in two people; so you might get a co-founder who is very operational and implementation-oriented, and the other founder may be very visionary and charismatic and at the front of the bus, showing the way. If you only have the vision, you can never deliver, and if you only have the execution, you’re really never going to do anything bold enough.

Are New Zealanders more action-focused than thinkers?
People are very happy and eager in New Zealand to get to work on a problem, but the real way to solve major problems is through changing the system itself. And the worst situation we have is that we are currently led by people who are not leading by thought – they are just doing. I don’t think there is any global thought leadership of what are some of the fundamental challenges we face this generation or the next 10 or 20 years, as opposed to between now and the next election. If you don’t have that in the national dialogue, it’s difficult for the rest of the country to get behind anything of significance.

Fellow entrepreneur Peter Thiel. Photo/Getty images

Many people have great ideas but go no further. How do they turn them into reality?
There are a bunch of tips in the book, but one that leans into my personal traits – it’s not for everyone – is about really researching and thinking about what it is you believe you’re trying to do. But as soon as you are convinced that it is worth doing, the tip is to cut off all ties to your previous existence and commit to doing it. Taking the leap is the first step, and once you’re in there you kind of start drowning, and have to start looking around for people who know what it’s like to drown, because they are the ones who will pull you up to make sure that your chance of succeeding in this is as high as possible.

How can we grow world-scale New Zealand businesses when so many are sold at the budding stage, including one of your own, The Hyperfactory?
The selling part is important for the next five to 10 years. At that point we might have a base of, say, 50 or 100 entrepreneurs who have had some level of success and are able to help the next wave. We have more models coming out at the moment, like Xero and Diligent, which are looking like globally significant companies with a committed New Zealand base. There’s lots more infrastructure to be able to do that, with The Icehouse and the Venture Investment Fund. We could hand-pick a bunch of great entrepreneurs from America or Israel or Europe and woo them to come and live in New Zealand and start companies. Create special visas for them, special funding arrangements. Because at the moment we’re growing [companies] organically with a very limited pool of mentors. Another thing could be to accelerate partnerships with global investors who understand how to back and scale companies. We only really have one at the moment, [PayPal founder] Peter Thiel. He invested in Xero, was the first investor in Facebook. He helped them enormously.

Is the tall poppy syndrome overstated?
For us, it was [about people] on the lookout for something to go wrong. For someone like Geoff Ross of 42 Below, certain bars wouldn’t stock the drink in New Zealand because they thought [the company was] trying too hard or being too ambitious. There’s an increasing community who are now encouraging of people doing things that involve risks.

Virgin Group founder Sir Richard Branson. Photo/Getty images

You have given up a year of your life to work with Sir Richard Branson on the The B-Team. What is it?
Its intention is to be a highly visible group of individuals who are suggesting that perhaps many people in business are misunderstanding what the fundamental role of business is in society to the detriment of their own community and their children’s future. Such as how business has got so incredibly short term in its outlook, versus a multigenerational, sustainable version. That it’s now a badge of honour to work to death to the negative impact on your health and relationships. To specific things like how does business eventually get to the point where it does have to account and pay for its planetary use.

Should all businesses hard-wire philanthropic/social motives into their plans?
Future businesses should be ones that build in those three elements: financially sustainable, but with significant social benefit and environmental sustainability. We have had 20, 30 years of what’s called CSR – corporate social responsibility – but that’s about companies setting up some kind of PR division with a small office in the corner that does a few things like sponsor a marathon.

What’s your proudest moment?
That’s an easy one. Seven months ago, a baby was being born. I was very proud.

Heart to Start, by Derek Handley (Random House, $39.99), is out now.