Posted on Thursday, Jan 21st 2021
If you haven’t already, please study my free Bootstrapping course .
I have always said that you need to bootstrap your way to validation and traction. ProjectManager.com Founder CEO Jason Westland did just that, and 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 further 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, just 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 to start my own business based on reporting to a Board that I learned a lot from. 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 start 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, I started the company 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 had 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 that were growing dramatically were there. 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. The projects were getting larger and larger to a point where we were averaging over a billion dollars per project. Sramana Mitra: Billion dollars for a 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 Projectmanager.com in 2008.
At that point in time, the worldwide financial crisis had hurt my second business. That’s when I realized 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 realized 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 could cancel anytime they wanted. At the conference, I had the idea of taking on 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 projectmanager.com. 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.
The discussion continues
here. This segment is a part in the series : Best of Bootstrapping . Bootstrapping to an Exit . Why is Bootstrapping Important? . How Can You Play this Low-Probability Game Intelligently? . Do NOT Go to VCs as Beggars - Go as Kings . Excess is NOT Required for Success . Bootstrap First and Raise Money Later . Some Bootstrapping to Exit Case Studies . The Buy Side of Bootstrapping to an Exit . Blitzscaling vs. Bootstrapping . Bootstrapping to Unicorns More »» . Cinedigm Acquires Bootstrapped 1Mby1M Company Future Today for $60 Million . Mailchimp Bootstraps to $600M Revenue . Bootstrapping from Arizona to $10 Million . Bootstrapped Basecamp Executes a No Nonsense Strategy . How Under30Experiences Bootstrapped to $5 Million . Bootstrapping with a Paycheck . How Algo.ai CEO Amjad Hussain Bootstrapped using Services from Michigan . Seed Investors Who Like Bootstrapped Businesses . How iHeartRaves CEO Bootstrapped a Niche e-Commerce Company to $20 Million . Bootstrapping with Services . How The Intern Group CEO David Lloyd Bootstrapped to $13 Million . How Passageways CEO Paroon Chadha Bootstrapped from Indiana . How SmartBuyGlasses CEO David Menning Bootstrapped to $50 Million . Death by Overfunding . How RainmakerForce CEO Mack Sundaram Bootstrapped Decisively to $5 Million+ . How FormAssembly CEO Bootstrapped a Virtual Company with a Paycheck . TimeSlips CEO Mitch Russo Bootstrapped to Exit with Sage . The VC-Entrepreneur Compensation Disbalance . BioConnect CEO Bootstraps with Sophisticated Strategic Maneuvering . Tremend CEO Marius Hanganu Bootstraps from Romania . Gesture CEO Jim Alvarez Bootstraps to $10 Million . SproutLoud CEO Bootstraps to $30 Million from Florida . Tuft & Needle CEO Bootstraps to Over $100 Million . Co-founders Bootstrap Linguamatics to Over $10M from the UK . Ownership Matters . Vainu Co-founder Mikko Honkanen Bootstraps from Finland . Entrepreneur Couple Bootstraps to $10M from Colorado . 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Discussing the Evolution of the Indian Startup Industry with Sasha Mirchandani, Kae Capital . Lean Company Bootstraps to $7M . Saatva Co-founder Bootstrapped a $25M E-Commerce Company . Looking at Terms with Heidi Roizen of Threshold Ventures . ADDA Co-founder CEO Bootstrapped with a Paycheck in India . Duda Co-founders Bootstrap with Paychecks . The Importance of Building Value with Shomit Ghose, Onset Ventures . Get Real Health Founder Bootstrapped Using Services . Bootstrapping Unique Vintage Using a Paycheck . Discussing E-commerce Startup Trends with Daniel Gulati, Forecast Fund . Bootstrapping a Digital Startup with a Paycheck . Discussing Seed Stages with Amir Banifatemi of K5 Ventures . Bootstrapping Avelead Using Services from Atlanta . Founder Bootstrapped a Big Data Company Using Services . Discussing Future Unicorns with Warren Weiss, Foundation Capital . Founder Bootstrapped Axosoft with a Paycheck . Raised a Series A with $10 Million in the Bank . 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Co-founder Bootstrapped a SaaS Company in India . Bootstrapped MindTouch to $12M+ and Exit . Mobiliya Technologies was Bootstrapped Using Services . What Traditional VCs are Looking for with Scott Sandell, NEA . Bootstrapped Srishti Software Applications with Services from India . How Robust SaaS Company RateGain was Bootstrapped from India . Bootstrapped eGroup to $20M in Charleston, South Carolina . Gravitant CEO Bootstrapped Using Services to $15M in Venture Capital . CEO Bootstrapped Sitecore Using Services from Denmark . Co-founder Dan Hermann on Bootstrapping Paint Nite . Founder Krishna Kumar Bootstrapped App Orchid Using Services . Bootstrapping a Web Hosting Company to $60M . Bootstrapping CloudSense with Services on Force.com from London . Bootstrapped Book E-Commerce Business BookPal . Student Entrepreneurs Bootstrapped a Zero-Logistics E-Commerce Company to $19M . Bootstrapped to a High Growth Inc. 500 Company . 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Bay Dynamics Co-founders Bootstrapped Using Services . Building an AI Software Company from Dallas . RJMetrics Co-founders Bootstrapped First, Raised $22M Later . Bootstrapping Niche E-Commerce Business BuyAutoParts to Exit . TemplateMonster was Bootstrapped to $15 Million . Bootstrapping Edge Hosting to $18 Million . Bootstrapping, Fund Raising and Exiting with Sefaira . Bootstrapping IdeaScale to $5M from Scratch . Bootstrapping to $10M from Finland . Happy Grasshopper CEO Dan Stewart Bootstrapped to Inflection . Bootstrapping Gravity Pro Using Services . Founder Builds Multiple Bootstrapped Education Software Companies . Bootstrapping to $10M from Australia, Raising $25M from the US . Bootstrapped Y Soft to $30M from the Czech Republic . Bootstrapped from Belarus, Raised Money from Silicon Valley