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Bootstrapping from New Zealand, Scaling in America: Jason Westland, CEO of (Part 1)

Posted on Monday, May 2nd 2016

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

I have always said that you need to bootstrap your way to validation and traction. Jason did just that, and has built a robust company from New Zealand. Read on, it’s a fabulous story.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Jason Westland: That’s way back in time than I expected. I’m from New Zealand in the Southern Alps. My first job was managing a project of 25 people. I was 22 out of university. I was in project management until around 15 years ago when I became the General Manager of a software company that grew fast. I was inspired, based on reporting to a Board that I learned a lot from, to start my own business. This is the third business that I’ve started.

Sramana Mitra: Can you give me a sense of when all of this is happening? When did you finish your last job and started the company?

Jason Westland: I finished my last job in 2004.

Sramana Mitra: Where were you based?

Jason Westland: I was based in New Zealand at that time.

Sramana Mitra: You started the company also in New Zealand?

Jason Westland: Yes, the company I started in 2008.

Sramana Mitra: Talk to me about how you started the company. What did you decide to do? What did the landscape look like? What are the anecdotal circumstances in which you started?

Jason Westland: I founded my second company by then. I was in New Zealand. I’d been invited to an exclusive, invite-only entrepreneurial conference called MORGO. You sign an NDA and everyone learns from one another. Two of New Zealand’s most successful software companies were there that were growing dramatically. At the same time, the week before the worldwide financial crisis had hit. I had downloadable software at that time. Sales were down by about a third which was unusual.

Sramana Mitra: You’re talking about when you were working?

Jason Westland: Until 2000, I was a project manager. They got larger and larger to a point where we were averaging over a billion dollars per project.

Sramana Mitra: Billion dollars for software project?

Jason Westland: They were IT projects, yes.

Sramana Mitra: In New Zealand?

Jason Westland: I left university and started managing larger projects. The 25 people started at a couple of million. I think it was around $4 million. I ended up, in 2000, managing the entire strategy program for British Rails in England. We had three projects that were all over a billion pounds. I was directly responsible for managing those.

Then I went back to New Zealand. The market was too small for large projects. I took a job in 2000 working for a software company. It grew until 2004 when I left. Between 2004 and 2008, I set up two businesses and had sold the first. I was in the middle of the sale for the second business in a conference when I had the idea for in 2008.

At that point in time, the worldwide financial crisis had hurt my second business. That’s when I realised that downloadable software such as the business that I had would likely be affected. Luckily, the transaction still went through. I had the idea at the conference of starting up a SaaS business. That’s where I realised that, with SaaS, it’s a lot harder to cash flow the early days because you don’t earn the full lifetime value of a customer upfront like you do in downloadable software.

A lot of companies at that time as a result of the financial crunch were going online simply because they can cancel anytime they wanted. At the conference, I had the idea of taking Microsoft Project which was a successful downloadable software tool for project management. To do that, I needed to build the world’s best gantt. While I was at the conference, I realized that I needed the best brand, best marketing, and best online gantt. At the conference, I called the guy who owned He was desperately in need of money. I also needed the best marketing and an awesome team. I was lucky to get a handful of senior people in New Zealand interested in this concept.

This segment is part 1 in the series : Bootstrapping from New Zealand, Scaling in America: Jason Westland, CEO of
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