A good way to think about this issue: As you prepare to sell preferred shares to raise money, ask yourself "Is this product worth the next ten years of my life

A good way to think about this issue: As you prepare to sell preferred shares to raise money, ask yourself "Is this product worth the next ten years of my life?" Come up with an answer that will satisfy your parents or spouse, not just your co-founders and seed investors. What can make it worth ten years? 1. A product with the potential to delight paying customers and make them talk to each other about how great it is. (If your revenue depends on ads, your customers are advertisers, duh.) 2. A big enough stake in your company (after you sell those shares) to give you good choices when it's time to do the next thing.