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Best of Bootstrapping: Scaling to Over $10M by Bootstrapping Using Services

Posted on Friday, Mar 20th 2020

We’re big believers in Bootstrapping Using Services, as you know. Here’s the story of CEO James Kane who scaled RWS to over $10 million in revenue using the method.

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?

James Kane: I grew up in a very small town in far northern New York. It’s a college town of about 2,000 people. My father was a university professor. He taught Mechanical Engineering at Clarkson University.

Sramana Mitra: What did you do for college or university?

James Kane: I left high school early at the age of 16 to attend university. I studied Math and Computer Science at Clarkson University. I ended up leaving Clarkson when I was 19 which is when business had picked up to the point where it had exceeded what I had expected to make working as a programmer.

Sramana Mitra: You started doing jobs while you were still in your undergraduate program. You were making so much money that you decided you wanted to quit.

James Kane: That is essentially the case. I had applied to several top tier universities. I had been accepted into Carnegie Mellon and Cornell. I wanted to study there, but our family didn’t have the money for me to go do that. I could attend Clarkson for free. The original plan was to go to school at Clarkson for free and start doing some side work to earn enough money to transition to a more prestigious school. The plan ended up being invalidated at the point where the amount of money I was making through working exceeded the amount of money that I can reasonably expect to make with a degree at a more prestigious school.

Sramana Mitra: What year does this bring us up to?

James Kane: Roughly 1998 in the beginning of the dot com boom. I finished around 2011.

Sramana Mitra: What happens next?

James Kane: The initial business that we had ended up failing.

Sramana Mitra: What was the business idea?

James Kane: During school, we built a computer algebra system called Calculus Machina for John Wiley & Sons. The purpose of that was to be able to build a computer system that could solve calculus problems in a way that students could reference to see step-by-step solutions. All throughout college, I was working on that software. It was ultimately released but was largely unsuccessful. Right around that 2011 timeframe, the relationship with John Wiley & Sons came to an end.

Sramana Mitra: What was your next move?

James Kane: I didn’t have a particularly good next move. I went and learned how to fly airplanes and I worked, for a couple of years, as a pilot.

Sramana Mitra: Why?

James Kane: There was no good reason. I was quite young at that time. I always liked learning new things and it was very different from what I had been doing before, so I threw myself into it. I really enjoyed it.

Our conversation 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

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