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Best of Bootstrapping: Bootstrapping ProjectManager.com from NZ, Scaling in the US

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
. 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
. Power2Motivate CEO Bootstraps to $80M from Canada
. Financial DNA CEO Bootstraps to $10M+ from Australia
. Big Barker CEO Bootstraps a Niche E-commerce Brand
. PrecisionLender CEO Bootstraps to Over $10M from North Carolina
. Master Bootstrappers with Over $1B in Exits
. Ultra Mobile Founder Bootstraps to Over $100 Million
. Bootstrapping a Two-Sided Marketplace to $10M
. Can You Bootstrap a Virtual Company to Over $5 Million?
. Capital Efficient Entrepreneurs Turn $1M into $80M
. Discussing the Journey Through Failure to Success
. From a Small Town to $12 Million
. Bootstrapping to Y Combinator and $10 Million Series A
. Bootstrapping a Marketplace to Over $10 Million
. Freightwise Bootstraps to $33 Million
. Bootstraps First to $5M ARR, Raises $10M Later
. Bootstraps in Europe, Raises Money and Goes Global in the US
. English Major Bootstraps a Tech Company
. Bootstraps with a Paycheck to $15M from Tennessee
. Queue-It Bootstraps from Denmark to the US
. Bootstrapping A Virtual Company To $25M
. ActiveCampaign CEO Bootstraps Using Services to $40M
. Alteryx Bootstrapped with Services to a Public Unicorn
. Inspyrus Bootstraps Using Services to an Awesome Business Model
. CEO Bootstraps Using Services to Millions from Russia
. Wiredrive CEO Bootstraps Using Services to $10M
. Scaling to Over $10M by Bootstrapping Using Services
. Bootstraps Using Services from Poland to a US SaaS Company
. ButcherBox CEO Bootstraps a Perishable Meat Business to Significant Scale
. Waveform CEO Bootstraps to $8M
. Bootstrapped Entrepreneurship from Estonia
. From Laid-off Engineer to Successful Startup CEO
. Imagine Easy Solutions CEO Bootstraps to Exit
. BannerBuzz CEO Bootstraps to $35M
. Bootstrapping a Virtual Company to Scale
. Bootstrapping Using Services from Wisconsin
. Best Tactic for B2B Startups
. Bootstrapping by Piggybacking from Romania
. Bootstrap First, Then Scale with VC Funds
. Bootstrap to +$10M First, Raise Money Later
. Madwire CEO Bootstrapped First, Raised Money Later to $120M
. Bootstrap Using Services First, Raise Money Later
. Wonderful Bootstrap with a Paycheck Story
. RushOrderTees CEO Bootstraps to $23M
. Bootstrapping with Freemium and Free Trials to $13M
. Bootstrapping, Pivoting, Gaining Liquidity, Scaling to $100M+
. Bootstrapping with Affiliate Marketing
. Bootstrap to Exit, Bootstrap Again, Then Raise VC Money
. Bootstrapping Using Services to $12M
. Bootstrapping an Ad Tech Company from Paris
. Bootstrapping a 100% Virtual Company from Ireland
. MiQ CEO Bootstraps with Services from London
. Bootstrapping to $8M During the Covid Crisis
. Bootstrapping a Marketplace from Brazil
. Bootstrapping Using Services from Sweden
. What Should Startups Do To Raise Seed Capital in 2021?
. EdTech Unicorn Bootstrapped First from Canada
. Coalition Technologies Co-founders Bootstrap to $10M
. Bootstrapping a Virtual Company to $10M from Atlanta
. Bootstrapping a SaaS Company with a Paycheck and Scaling
. Bootstrapping with Services to $20 Million
. Onit CEO Bootstraps First, Raises Money Later
. Pura Vida Founders Bootstrap to $130M
. Lawline CEO Bootstraps to $10M
. Bootstrapping a Technology Product Company from India
. Codesigned CEO Bootstraps Using Services
. Rukkus CEO Follows Bootstrap First, Raise Money Later Strategy
. Bootstrapping and Managing a Successful Pivot
. Ukrainian Entrepreneur Bootstraps to Global Scale
. Bootstrapping a Niche E-Commerce Venture
. Bootstrapping Planon to $100M from The Netherlands
. Co-founder Bootstrapped with a Paycheck from Indiana
. Bootstrapping an Education Company
. Bootstrapping an IoT Company from North Carolina
. Serial Bootstrapper Bootstraps to $27M
. Bootstrapping Identity Automation Using Services from Houston
. Bootstrapping ProjectManager.com from NZ, Scaling in the US
. Bootstrapping to $15M in Three Years
. Peruvian Entrepreneur Bootstraps to $200M
. JotForm Founder Bootstrapped with a Paycheck
. WeGoLook was Bootstrapped from Oklahoma
. Bootstrapping AutoClaims Direct to $15M
. Meltwater Founder Bootstrapped to $200M
. Bootstrapping to $20M From London
. Synechron CEO Bootstrapped to $300M
. Unique Vintage was Bootstrapped with a Paycheck
. Toptal CEO Bootstraps a Virtual Company to Scale
. Bootstrapping to $45M from Chicago
. Vacasa Co-founder Bootstrapped to $100M
. Bootstrapping Infinitely Virtual All The Way
. Bootstrapping to Exit Discussion with David Lambert, Right Side Capital Management
. Bootstrapping a Healthcare IT Company to $100M
. Discussing Seed Rounds with Cindy Padnos, Illuminate Ventures
. Auction.com Bootstrapped to $180M in Online Real Estate
. Discussing the Silicon Valley – India Corridor with Naren Gupta of Nexus Venture Partners
. Bootstrapped with a Paycheck to Techstars and Acquisition
. Discussing People vs. Market with Jon Staenberg, Staenberg Venture Partners
. Bootstrapping a Highly Profitable Company in Social Media Marketing
. Discussing Investments in Indian Startups with Anand Daniel, Accel Partners
. Bootstrapping an Evergreen Business from Oregon
. Discussing Startups in Africa with Osayi Igharo, Ripple VC
. Investing in Concept Stage Startups with Matt Holleran, Cloud Apps Capital Partners
. Serial Entrepreneur Bootstrapped Two Startups to Huge Revenue
. Discussing Investment Strategy With Deepak Jeevankumar, Dell Technologies Capital
. Bootstrapping Hotelplanner.com to $20M with Intelligent Financial Engineering
. Discussing Investing Across Sectors in India with Swapna Gupta, Qualcomm Ventures
. Bootstrapping Cleverbridge From Germany
. Discussing Open Opportunities with Hemant Mohapatra, Lightspeed Venture Partners
. Bootstrapping E-commerce Company Fun.com
. Discussing Seed Rounds with Bruce Cleveland, Wildcat Venture Partners
. From Friends and Family Funding to $30M Exit
. 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

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