In the last eight years I have moderated several hundred Bootstrappers Breakfasts. 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.
Ten Mistakes Early Stage Bootstrappers Often Make
- 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 But High Paying 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 strangers
- 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 Bootstrappers Breakfast.
Related Blog Posts about Mistakes
- Think Twice Before Saying
- 5 Mistakes CEOs Make In Demos
- Five Mistakes to Avoid in a Nurturing E-Mail
- Five Blogger Outreach Mistakes To Avoid
- Five Serious Financial Mistakes Bootstrappers Can Avoid
- Common Mistakes in New Product Introduction Demos
- How I Avoid Sending E-Mail I Regret
- Stay Tuned: We are being purposefully vague right now.
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