Guy Haddleton is a walker. It's the slow and steady, one step at a time approach that appeals to him. He knows from experience that the Alps, the Himalayas and the Pyrenees can all be broken down into the effort it takes to put one foot in front of the other. And he sees no point escalating things to the discomfort of a run or even a light jog.
"If we were supposed to run, I would've been given four legs like a dog or horse," he says, struggling to hide his grin. "I'm not supposed to run, so I don't try it."
This philosophy has also seeped into the way he talks. In stark opposition to the cliché of the brilliant mind that moves at a million kilometres an hour, Haddleton doesn't blurt out his thoughts. He pauses after every question, searching for the right words, and delivers his views carefully, straying away from the rational path only sometimes to share the odd anecdote. Minds, like feet, don't always have to rush into things.
Haddleton, who last year saw Anaplan, a software business he co-founded, debut on the US stock market with a market capitalisation of US$3 billion ($4.6b), tells the Herald that these things don't happen overnight. The unicorn – the name given to a business with a valuation above $1 billion – came at the end of 12 years of long nights and hard yards, and that isn't counting the work that went into his earlier ventures.
By the time he started Anaplan with long-time collaborator Michael Gould in 2006, Haddleton had already worn in his entrepreneurial boots with his earlier business, Adaytum, which he founded in 1990 and eventually sold to IBM Cognos for a modest US$160 million (NZ$240m).
Add to this the fact that Haddleton was one of the early investors in a then-little-known company named Xero, and it's evident his business tenacity was matched with an eye for a good opportunity. But these incredible fortunes came from a somewhat inauspicious place.
"I was Mr Average at school," he recalls. "I was average at academics, I wasn't in the first XV, I wasn't in the first XI, I probably drank too much and I probably smoked too much. I was your typical 17-year-old Kiwi."
This ordinariness followed him through to university, where he dropped out of law and commerce in his first year. Not because of laziness or a lack of ability, but more because of an abject lack of interest in what he was studying.
"To be frank, it was my parents' dream, not mine," he says.
During this uncomfortable limbo between youth and adulthood, Haddleton stumbled on a recruitment advertisement calling on civilians to join the New Zealand Special Air Service. This moment of serendipity marked the first step in what would turn into a military career spanning more than a decade.
Business founded by Kiwi hits $4.6 billion value on US stock exchange
"I spent eight years as a full-time territorial force soldier in SAS and then ultimately ended up as a troop commander," he says.
Close calls hammered home an important insight for Haddleton: being surrounded by the right people can mean the difference between life and death.
"That taught me a lifelong lesson, to surround myself with outstanding talent," he recalls.
"Everyone in my troop was far more skilled and far more capable at doing certain things than I ever was."
His experience also meant he never suffered from the insecurity some executives feel when they are surrounded by brilliant people. He understood from the outset that his role was to assemble the best possible team and make them believe in something bigger than the trenches dug today. In other words, his business career has been defined by a militant focus on purpose and people.
Scavenging cardboard boxes
Haddleton met the first person he'd hire while scavenging through leftover cardboard to make the packaging for the first products from Adaytum.
"While out on the streets on Bristol, I met an artist who was also scavenging," says Haddleton, shaking his head as if he still can't believe it.
"I asked him to come work with me, and he ended up staying with me for 18 months. You never know where you're going to find outstanding talent."
While his hiring processes grew in sophistication alongside his businesses, Haddleton still leaves a little room for the emotional nudge that tells him this is the right person for the job.
"For any appointment, I assess the natural talent of an individual and then I look at what skillsets he or she has built around that talent. And I look at what they've achieved in their lifetime," he says.
"But then a key question I ask, and it's one that many don't ask, is 'Do I actually like this person?' And that's the gut speaking, and it's so important."
This is about the cultural fit of a team member and their willingness to support the rest of the team.
And this rule is most important when it comes to appointing a chief executive.
"It cascades down," he says. "Get the wrong CEO and the company will go off the tracks. I think there was only one critical decision a board has to make outside of general governance and that is: Is the CEO fit for purpose for that particular stage of the business? I don't think enough boards challenge that on a regular basis."
The point he's making is that CEOs shouldn't be allowed to sit in a cosy position indefinitely as the business chugs towards oblivion. The CEO position should be challenged. And when the person in the big chair is no longer suitable for the evolving objectives of the business, they should be removed.
"Business is quite simple if you think about it like that: do you have the right person in the right spot at the right time?" says Haddleton, before conceding that the practical application isn't quite as easy as the theory.
"It's terribly hard for founders because they build their business on the sweat of the first executive team. And then to say it's time to move on is tough."
As even a cursory glance at CEO pay packets reveals, replacing the big boss doesn't come cheap. So is it worth forking out extra cash for the best?
"Look, some of the executive remuneration out there is absolutely ridiculous," says Haddleton.
"That said, if you want somebody who is really exceptional, drives culture and drives growth in the business, then you've got to pay the market rate. The market dictates the rate. And I know it's crazy, but I don't know how you fix it."
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Profit isn't everything
To explain the issue of purpose, Haddleton harks back to the early days of his business career when he was working at a start-up in the UK. He recalls seeing a group of three or four staff sitting outside the chief financial officer's office building spreadsheets to evaluate business opportunities.
"I suddenly said to myself that someone needs to automate this. Why does everybody need to build a new spreadsheet from scratch?"
This tiny observation would evolve into the purpose that came to underpin Adaytum – and one that would later be fully realised at Anaplan.
Haddleton explains the point of all his efforts was to remove arduous steps and make it easier for businesspeople to focus on actually running their enterprises.
A purpose, he says, can't be faked. "It's not just a slogan for the day," he says. "People quickly see through a fake purpose. You know what's real."
He says that if you can match your idea to a clear purpose that has a large potential market, then it's always worth going for – even if it means burning through cash in the early days.
Haddleton says far too many start-ups are stunted by investors who get bogged down by a premature fixation on immediate profitability rather than looking at the broader picture.
"A board member once said to me 'we need to make profit'. My response was 'why?' And everybody looked at me like I was crazy. And then I continued, 'well, of course, you need to make profit eventually, but let's have a look at the economic future of the business and the future market. So doesn't it make sense to invest like hell and take that market? You have to move really fast these days."
This strategy can be seen in companies like Uber and Netflix, which are willing to sink billions of dollars into debt while keeping their gaze firmly focused on the goal of dominating a market worth many billions more.
"The inherent profitability is there. It's in the growth. You're just scaling."
Economies of scale provide a seamless segue to Haddleton's next big area of interest: the marijuana industry.
Last year he was confirmed as lead investor in Kiwi cannabis company Helius Therapeutics – a start-up he was drawn to because of the business credentials of its founding partners Paul Manning, Gavin Pook and JP Schmidt.
While marijuana isn't the obvious move for a software guy, Haddleton says he sees a group of talented people coming together with a joint purpose that has enormous commercial potential.
The global cannabis market is already worth well over $100b and Haddleton says this will only continue to grow in coming years.
One thing you won't see Helius doing, however, is getting involved in the recreational side of the business. Haddleton says that as long as he is involved, Helius won't touch anything recreational.
The reason is that this doesn't align with the purpose of the business.
"Helping 720,000 Kiwis come off pain is a purpose," he says.
"That has real merit. As does removing the dependency on opioids. If we can just make a little movement on that, you can do something useful."
This story is also personal for Haddleton, who has seen the restorative impact of medicinal cannabis first-hand, on a co-worker who had long struggled with health issues.
This is Haddleton speaking from the heart, or the gut, but it drives home the point that there are people who need what he and Helius are working on.
While Haddleton has his hands full on the cannabis side, he's still keeping a little space in his life for his old passion, computing.
"I'm involved with a high-performance computing start-up out of Cambridge called Nyriad and I have great hope for that."
Once again, the animated Haddleton is betrayed by a small grin that hints at his optimism about the venture.
"It's pre-revenue, so it's a long way to go with that one," he assures the "Herald", offering a reminder that he's a walker rather than a runner. Which is to say he's still focused on taking one step at a time.