If you feel like your "quest for capital" is taking every last ounce of energy out of you, then you're probably right where you should be (like it or not).
Raising money isn't a side business - it's a fulltime job!
Unfortunately that fulltime job is both necessary and completely distracting at the same time. While you jump through hoops to satisfy half-interested investors and partners, the people that you should be jumping through hoops for (your customers!) are going largely ignored.
So the question becomes - how can you spend less time chasing investors and more time growing your business?
There are two parts to the answer:
Part One: Size up your Investor
Not every investor is worth jumping through hoops for. You really need to figure out who is worth spending the extra time with and who is just kicking the tires or stalling.
A few ways to size up the investor are:
1. Ask how long a typical deal takes. Every deal is different, sure, but they should have a rough estimate. If the investor has no idea how long the process could take and can't afford you an answer, you need to look elsewhere. A good, smart investor will want to weed you out as quickly as possible to get on to better deals. A lousy investor will string you along for months with a constant string of inane questions.
2. Find out when the last deal like yours was done. Lots of investors love to talk about doing deals, but very few actually do them! You need to know that the investor you're sitting across from has actually done a deal in the last six months, year or two years. A deal they did that was "kinda similar" five years ago isn't necessarily a good sign that there's another one to come.
3. Find out if they've been successful. Successful investors that have made lots of money doing deals just like yours are likely to write more checks. It's no different than if you were making money in the stock market - you're probably going to continue to invest more! But if you're getting your butt handed to you, you're probably going to take a long time to make an investment decision, if ever. Think about your investor sitting across from you in the same way.
Part Two: Get to NO Quickly
Unlike a sales call where you want every customer to say "yes!", when it comes to investors, you want them to say "no" as quickly as possible, so you can find one that says "yes!".
The worst mistake entrepreneurs make when raising capital is thinking that "it sounds interesting" is the same as "here's a check". They aren't, so don't confuse them. As I've said before, if the investor isn't writing a check, the answer is already "no!".
Don't be afraid to push an investor away. Investors know that the really good deals don't come along that often, so you don't exactly need to beg them to do a good deal if they like it. For this reason, you need to let them know that you're OK with "no" if that's really the answer.
A quick translation of investor "no" terms:
1. "It sounds interesting" - the answer is no
2. "We're not prepared to invest right now" - the answer is no, and will probably stay that way even when your grand kids visit the office
3. "We'll have to give it more thought" the answer is no, and the only thought we're going to put into this deal is how to best avoid your calls in the future
... the list goes on, but as you can imagine, if they aren't chasing you, they're not interested.
The Best Use of Your Time
If this sounds like raising money is a time-wasting pursuit, the answer is both yes and no. Yes, you're going to waste lots of time talking to investors who won't write a check, but it's a necessary evil to raising capital.
On the other hand, if you focus on weeding out investors the way they are focused on weeding out bad deals they don't want to do, you'll spend a lot more time getting checks, and a lot less time getting frustrated.