The Bootstrapped, Scalable Start-up: Charlie vs. Ted
October 23, 2009 – 1:21 pm | by Matt AckersonCharlie and Ted are two web entrepreneurs, equal in brain power and wit.
Chapter 1: Background Stats
- Charlie’s company, Charlie Inc., has hired 4 employees and has $100,000 of his own money in start-up capital; Ted Inc. has brought on board one business partner to work on the tech side of things and has $1,000 in capital.
- Charlie Inc. and Ted Inc. both have the same web-based B2B product idea, called Digi-Widgets.
- Their target customers are small to medium sized businesses (SMB’s)
- This is Charlie’s first start-up, while this is Ted’s second (his first one failed)
- Both Charlie and Ted happen to start work on their businesses at the exact same moment on the exact same day…
And they’re off!
Chapter 2: First Steps
Ted:
- Sets up a make-shift office in his apartment with his business partner.
- Talks to several customers about his product idea.
- Designs and sketches what the Digi-Widgets will look like.
- Asks for feedback.
- Tries to identify the problem being solved.
- Asks customers to quantify, in some way, the problem, if it exists.
- Creates a crude version of the Digi-Widget for customers to use for free.
- Collects feedback to make changes.
- Makes changes; unfortunately they don’t have the time or the resources to implement all the features they wanted.
- After 2 months of hard work, he begins charging $100 per Digi-Widget; 10 customers sign-up.
Charlie:
- Rents a cheap office for him and his team for $2,500/ month.
- Pays a modest salary to himself and each of his four employees ($10,000/ month).
- Charlie and his team set to work building version 1 of the Digi-Widgets.
- They work with their heads down for 3 months.
- Charlie in the meantime initiates talks with potential angel investors.
- Charlie also occasionally goes out and gathers testimonial quotes from potential customers about why they might buy the Digi-Widgets.
- Builds a few strong relationships with several customers.
- The 1st version of the Digi-Widget is delivered a month late, but it has all the key features.
- Customers start using the service for free for 1 month.
- Makes some changes based on customer feedback and starts charging $75 per Digi-Widget; 4 customers sign-up.
Who will succeed? Both? Neither?
Tune-in tomorrow for the exciting conclusion!

One Response to “The Bootstrapped, Scalable Start-up: Charlie vs. Ted”
By John Exley on Oct 26, 2009 | Reply
Matt, I think this is another great example of your creativity! Nice idea for a blog.
I think Charlie seems to followed a recipe to succeed, however as you know the ‘game’ of entrepreneurship is incredibly difficult to predict! I love how Charlie offers his product free for the 1st month.
The ‘freemium’ (sp?) business model is one that I think has more promise, as it removes obstacles and risk for the buyer/potential customer.