Ten Mistakes Early Stage Bootstrappers Often Make

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

1. Leaving Your Assumptions Implicit: Not Writing a Customer Development Plan
2. Believing that Anyone Will Want Your Product: Not Targeting a Specific Buyer
3. Confusing the User (or the Audience) with the Buyer/Customer
4. Believing Your Product Will Sell Itself (Looking for Smarter Prospects)
5. Developing the Full Product: Not Selling the Smallest Piece Possible at First
6. Not Focusing on Break-even and Profit
7. Expecting Too Much Too Soon: Not Planning for “Target Practice”, Iteration, and Improvement
8. Confusing VC with Customer: Going for (2% of) a Really Big Market
9. Expecting the Same Control Over Prospects and Team Members as Your Code Base (Single Founder “No Compromise” Mindset)
10. 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

1. Managing different aspects of your identity at personal, family, and business level.
2. Understanding the emotional connection required for a successful business transaction: mission, brand promise, and  logo.
3. The networking etiquette in Silicon Valley: cards, introductions, how to get acquainted.
4. Making the transition from selling to friends to selling to strangers
5. 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.