From Nesheim Online
People come with the money. That person is the investor. He will sit on your board of directors and direct you. He is your new boss. You will have to live with him for half a decade. So pick wisely.
If you pick family-friends-fools money, you will have to live with less-than-the-best investor professional. That can slow you down when they ask so many naïve business questions. But it may give you freedom from a heavy handed boss (the occasional ego-centric angel or arrogant venture capitalist).
If you pick an angel, you will live with a person expecting to often meet with you, give you advice that is expected to be followed, and dig into your business in minute detail. That may interfere with your time to execute your business plan. But it may give you the executive experience in your industry that you are missing.
If you pick a venture capitalist, you will live with a tough minded professional who expects to be in charge (“The person with the gold sets the rules.”). That may pressure you into making strategic moves you think are not wise. But it may give you connections to large customers, strategic partners and to a lot of precious cash.
You manage each type of investor in different ways. Family-friends-fools are best managed with regular (every two weeks will do wonders) email communications about progress (be honest about the bad things) and a phone call to each, one-on-one, every month. One person will attend monthly board meetings (but others will occasionally request to observe at a meeting).
Angels are managed by embracing their eagerness to jump into the business and help. They have less time than they think they have (“Ops, time to go fishing for three weeks for black marlin off the outer banks of Australia”). So make appointments, perhaps for a weekly in-person morning of work. Hand-on work is expected of you and the angel. Take full advantage of the time offered. Assign work tasks to the angel, just as you would a vice president. Angels are experienced business people, from successes in the past as outstanding managers. They can be of significant assistance if you manage them proactively.
VCs are hard ball professionals. They expect you to meet monthly at board meetings and tell them everything important. You manage them best with frequent communications between board meetings. Emails are used to ask questions (copy everyone on the board, including observers). Use ad hoc telephone conference calls (including everyone, just like in a full board meeting) to address an important issue that has popped up and to make a decision (“We need to decide on how to respond to attacks at our customers in Asia by XYXCorp whose sales reps are telling lies about us going bankrupt.”). If you do not manage the VCs, they will manage you. Give them homework and hold them accountable for results (e.g. the introduction to the VP of business development at Amazon).
VCs are optimists, just like you, the entrepreneur. So they promise more than they can deliver. Serial entrepreneurs know that means CEOs must do the heavy lifting. VCs will do their best to provide a few introductions to strategic partners, customers and other VCs as requested. Experienced CEOs will not lean on VCs because they know you cannot win a race running with crutches.
If you respect that a person comes with the money, then you will not be disappointed. You can then plan to manage your new enterprise to get the most out of that person.