As a result, in most cases, reality is worse than the plan. Therefore, you should always raise more money than you think you will need. Forget the issue of dilution at a low valuation. The process of raising money is time consuming and disruptive. Involvement in continuous fundraising typically causes more damage than the dilution.
Managers often wait until the last moment to tell investors bad news.
This is a grave mistake because it shakes investors confidence in the ability of management to monitor and manage the company in the world of change. The golden rule is not to promise more than what you think you can deliver, and, if there are problems, report them as early as possible. Entrepreneurs are often not objective about their business, perhaps because of their optimistic nature. As a result, it is very dangerous to invest personal or family money. The entrepreneur invests enough in terms of opportunity costs and the cost borne by the family.