Over the years I have moderated several hundred Bootstrapper Breakfasts (since starting them in Silicon Valley in 2006). After doing a hundred or so and working with many clients who were bootstrapping I came up with a checklist for common mistakes bootstrappers and bootstrapping teams make in their first year or so.
- Leaving Your Assumptions Implicit: Not Writing a Customer Development Plan
- Believing that Anyone Will Want Your Product: Not Targeting a Specific Buyer
- Confusing the User (or the Audience) with the Buyer/Customer
- Believing Your Product Will Sell Itself (Looking for Smarter Prospects)
- Developing the Full Product: Not Selling the Smallest Piece Possible at First
- Not Focusing on Break-even and Profit
- Expecting Too Much Too Soon: Not Planning for “Target Practice”, Iteration, and Improvement
- Confusing VC with Customer: Going for (2% of) a Really Big Market
- Expecting the Same Control Over Prospects and Team Members as Your Code Base (Single Founder “No Compromise” Mindset)
- Treating the Business Like a Hobby (Thank God for Significant Others, Recently Deceased Relatives, and Crappy Day Jobs)
Five additional challenges that also need to be navigated
- Managing different aspects of your identity at personal, family, and business level.
- Understanding the emotional connection required for a successful business transaction: mission, brand promise, and logo.
- The networking etiquette in Silicon Valley: cards, introductions, how to get acquainted.
- Making the transition from selling to friends to selling to a strange
- Making the commitment to a business footing: licenses, structure, tracking expenses (and acknowledging that now you can fail).
Adapted from a talk I gave in August 2009 at the San Francisco Bootstrapper Breakfast.
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