How should I ask friends and family to invest in my startup without making things awkward?
Phase 1--Send a blind email (Subject: Investment Opportunity or Investors Wanted) so that no one sees who else is on your "hit" list. Outline your plan. Do not ask directly for the money. Ask for investors. Invite questions, comments, and feedback. See if you get any bites.
Phase 2 - Directly (face-to-face) discuss your plan with anyone who demonstrates interest.
Phase 3 - Periodically, follow up with an email or letter. Keep your potential investors informed. If, however, you want the money more than you want to avoid making things awkward, ask (by phone or in person) for feedback.
Elinor Robin, Ph.D.