Date posted: 01/12/2016 6 min read

The billion-dollar gift

It was a simple question that someone asked entrepreneur Linda Jenkinson, but she calls it the billion dollar “gift” that helped her build her international business career

In brief

  • In a career spanning more than two decades, the serial entrepreneur has started multi-million dollar businesses, won numerous businesses accolades, and is renowned for her philanthropic and social ventures
  • The keys to doing business in the 21st century is having imagination, and knowing how to collaborate
  • Typically, by the time you’ve spoken to 30 to 50 people, you have the answer to what you want

By Tony Malkovic

Photography by David Unwin

Linda Jenkinson is a serial entrepreneur who has a unique approach to spotting opportunities — and then making the most of them.

“I have never started a business that I know anything about,” she says.

“I’ve always brought an outside perspective, and I’ve always been disruptive and I’ve brought new ideas and technology to it.”

Jenkinson, a former chartered accountant, could be described as one of New Zealand’s most successful and respected business people.

In a career spanning more than two decades, the serial entrepreneur has started multi-million dollar businesses, won numerous businesses accolades, and is renowned for her philanthropic and social ventures.

Less well known is how she does it, and the conversation that re-defined her approach to being an entrepreneur.

It was part of a chat she had in the early 1990s in Wellington with US colleague Greg Kidd.

“He said: ‘Why don’t we start a billion dollar business?’,” she recalls.

“I said: ‘OK let’s do it’.

“Then we started figuring out how we actually build a billion dollar business.

“I was the entrepreneur, he was the thinker. And he said: ‘If we come together, we can take this to a whole new level’.

“Then I took the approach that you can do anything — it’s just a matter of figuring out how.”

Which is basically what they did.

The result was Dispatch Management Services (DMS), a start-up that bought dispatch companies and used technology to build a network of same-day delivery services which helped re-shape the courier industry.

They floated it on the US Nasdaq exchange, with DMS growing to become a US$230m business operating in the US, the UK, Australia and New Zealand with more than 6,000 staff.

And although she claims she might not know much about the businesses she goes into, Jenkinson does her homework. Heaps.

Her “formula”, as she calls it, is basically a combination of do-it-yourself due diligence and what you’d call investigative networking.

“The formula is you go to two people and you say ‘I’ve got this question, do you mind having a coffee and talking about it?’,” she explains.

“And when you’re finished, you say to them ‘Can you recommend two people that I can talk to about this?’

“Then you send the second group of people an email to thank them for the time for the interview, and ask if they can suggest two people each to talk about the issue.

“Then you go and meet with the next four people… and so on.

“Typically, by the time you’ve spoken to 30 to 50 people, you have the answer to what you want.”

You might not find Jenkinson’s formula in a standard MBA syllabus, but she says it works.

“I can tell you, I use that formula to do anything I want: raise money, answer questions, do whatever, sell a business — it’s like a classic formula,” she says.

“But it has many bits to it, and you have to do all of it.

“If you use this [approach], it changes the whole way you approach the questions you’re asking.

“Because the process of doing it will give you the answer.”

Jenkinson says one of the keys to being a successful serial entrepreneur is to spot a market trend and then make the most of it.

After DMS, she did it again.

Passionate advocate

In 2000, she realised that ageing Baby Boomers like being pampered, and bought and grew the US-based LesConcierges. This year, it merged with the European concierge group, John Paul, to become a global business employing more than 1,000 people.

Jenkinson is a passionate advocate for New Zealand business and innovation. She’s on the board of Air New Zealand and The Icehouse startup hub; a winner of Westpac’s Women of Influence awards; and the winner of a Kea World Class New Zealand Award.

She spends much of her time in San Francisco and Sydney, and a lot of other places as well.

“I’ve lived in 23 cities around the world,” she says, adding that she’s basically a global citizen, often flying to a new city a couple of times a week.

That lifestyle is a long way from where she started, growing up on a dairy farm in Palmerston North, with a three-hour round bus trip to school each day.

Typically, she made the most of her time.

“I learned how to read a book a day on the school bus,” she says.

School led to university, studying accounting/finance and computing, and then a job with Price Waterhouse (now PwC), and later a job consulting across Asia-Pacific with A.T. Kearney.

“I always wanted to make a big difference in the world,” she says.

“And I wanted to do it through business.

“My dad built more than 15 businesses but none of them more than $2-$3m in revenue.

“I wanted to build big businesses but in a way that made a positive difference in the world.

“That’s really what I’ve wanted to do since I was 21 years old.”


Jenkinson says one of the keys to doing business in the 21st century is having imagination, and knowing how to collaborate.

Which she says is why Silicon Valley, in the San Francisco Bay Area, is light years ahead of other places.

“In Silicon Valley, everyone thinks: ‘Can I make it a billion and what is the possibility?’,” she says.

“That’s the conversation, it’s a conversation of possibility.

“Instead of saying ‘I’ll get the calculator out and check the practical ABCs’, which is very much the strength of New Zealanders and Australians.

“But that is not a strength when you’re imagining something new.

“The first step of it is the imagination, imagining what it could be, following your intuition to say ‘What is something that hasn’t been there before and what could it look like?’.”

The next thing is to start talking about it with others, and letting it snowball.

“If you go to Silicon Valley, everyone talks about their ideas,” she says.

“Everyone wants to know what your next idea is, they want to tell you who else is thinking about that, who you could collaborate with or ‘here’s an opportunity’, or ‘you should talk to this person’.

“That’s the fundamental reason why it works, because it’s so collaborative, which very much fits in with who I am.”

But at some stage, you need to do your sums and ask what your business idea might look like. That’s where the skills she learnt as a CA kick in.

“I loved maths. So many people are scared of the numbers. Having that complete confidence with numbers is a huge positive,” she says.

“I can figure out business models, that’s what I do.

“I can look at something and say ‘How can you build the revenue stream, how do you structure a business so that it will work?’ ”

The flipside of Jenkinson is that she wants to help others succeed.

Her numerous social ventures include WOW for Africa, an initiative she co-founded in Dakar, West Africa, that helps grow small businesses run by women.

“I took the concept of an incubator and grants for the first lot of money to entrepreneurs to educate them how to use money, how to build bank accounts,” she says.

“By the time they finished the programme, their businesses were profitable and they could go and get money from a bank, so it was sustainable.”

Jenkinson says her next venture will also tackle a pressing issue.

“Every minute, a million disposable cups get chucked into landfill or the sea. The disposable world, I’m going to try to help eliminate it,” she says.


She might be a successful entrepreneur in her own right, but Jenkinson says three people in particular have influenced her.

“My father gave me the imagination and belief that you can do anything,” she says.

“John Green at Price Waterhouse many years ago in Wellington made me realise that it didn’t matter if it was a big company or small company, he had complete belief that I could it.

“Anything I did, he believed in me.

“And Greg Kidd asked me that question about starting a billion dollar business — How do you start a billion dollar business? — and he asked me that question 25 years ago.

‘Twenty-five years ago, I got that gift.

“When you start thinking like that, you start thinking completely differently.”

Tony Malkovic is an award-winning freelance journalist.

This article was first published in the December 2016 issue of Acuity magazine.

How to spot and maximise opportunities

  • Think big, think global

    Think big, think global, maybe ask: “Why don’t we start a billion dollar business?” You might not get there, but just asking the question will help get you to another level.

  • Positive thinking

    Have the imagination and belief that you can do anything.

  • Networking is key

    Network and tap in to your contacts’ contacts.

  • Collaborate and create

    Collaborate like you’re in Silicon Valley.

  • Plan ahead

    Figure out your business model – and nail the revenue scheme.