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Bootstrapping from New Zealand, Scaling in America: Jason Westland, CEO of (Part 2)

Posted on Tuesday, May 3rd 2016

Sramana Mitra: What about money? Hiring high-level people costs money.

Jason Westland: It does. I sold my first business. My second business was sold shortly after that. I invested all of the money from those two businesses. I then went and mortgaged the house. My mom mortgaged her house. I took out some credit card debt. It was really high-risk in those early days. I didn’t take on board any outside funding.

Sramana Mitra: How long did it take you to get a first version of the software out?

Jason Westland: We had the first version within nine months. My take on it is, it failed miserably. There are two reasons for that. Our churn rate was ridiculous. The second was that the product was incredibly buggy and slow. We did a second iteration, which took another six months. Finally, two years after we started, we had a version that was super fast where all known bugs were fixed. At that point in time within three months of going live, the business took off.

Sramana Mitra: What about customers? When you said the business took off, who were the first customers to embrace your product? How did you find them and how did you sell?

Jason Westland: We didn’t use Google AdWords until about a year and a half ago. I simply built a community of people who were interested in project management. Because I had a wealth of project management experience, I was easily able to create a LinkedIn group, send out a newsletter, have a YouTube channel, and start building content. I put a lot of content up on the website.

We had the best blog at that time. We were also the only ones who were doing twice weekly webinars where I’d offer free advice. I spent, at least, 50% of my time in offering free advice, templates, and ebooks. What happened was that it built a big following to the point where if you were to go to, you will see that we’ve got seven million YouTube followers. We’ve got some really big numbers – half a million on our email list. It’s the conversion from that following that has helped us throughout all those years to grow.

Sramana Mitra: What segment were you getting the traction from?

Jason Westland: The biggest segment was people who were frustrated with Microsoft Project. The first issue is, it’s on your desktop. The second is the files are quite large. If you want to send a project to someone else and it’s 20MB, it’s not easy to do so. The third is you can’t collaborate online. The fourth is at a glance, you can’t tell if your project is on track or not. I wanted to solve that problem.

When I managed projects for all those years, we built dashboards and very visual features in the product so that people could log in and they can literally import their project plan and, in seconds, it would populate all the relevant areas of the system, and they can see if the project is on track.

This segment is part 2 in the series : Bootstrapping from New Zealand, Scaling in America: Jason Westland, CEO of
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