The fact is fundraising can be a colossal waste of time. You give your pitch hundreds of time when there are only a few investors (you want) that will get to the finish line. Here's how to narrow the field.
1. Stop Talking to People Who Will Never Invest
"You're a bit too early," said every investor to every early-stage founder. Especially when you're running a B2B SaaS company doing less than $40K of monthly recurring revenue. As the founder, you're thinking, "WTF, aren't you early-stage investors? If I had that revenue, I wouldn't be talking to you in the first place."
If you want to avoid banging your head against the wall, talk to investors who invest at the stage your company is currently in. Don't raise $4MM from institutional VCs if you have an enterprise software company that's not generating revenues.
Don't talk to FinTech investors if you're starting a robotics company. Don't talk to a series A firm if you are raising a $20MM growth deal. It can be emotionally defeating to hear "you're too early" or not a good fit meeting after meeting. Know details about everyone you're talking to and who they invest in so you can talk to the right investors.
2. Get Good and Curated Introductions
How you meet the investor matters because most of the time they are thinking, "Who is this person, how did they get in front of me, and are they going to be smoking hundred dollar bills of my money in some office with a ping pong table?"
The best introductions are from people (entrepreneurs, other founders) who have already made the investor money. Those are solid leads. Also, don't get upset if you are pushed down to the associate or the junior person on the team and you're not meeting a partner on your first go round. If you're successful with that meeting, you now have an advocate and internal sponsor--and a very strong one at that given they will be helping you pitch the business to their boss.
Also, you never want to get introduced to an investor by someone who should be investing but isn't. That subtext is not going to help you ("this deal isn't good enough for me, but I think you should be investing"). Obviously, I'm generalizing--you can get excellent introductions from investors who are not investing if it's not their space or their thesis, but general intros from people who should be investing but aren't? No bueno.
3. Don't Go Out for Coffee
Never have an informal cup of coffee when you're out raising (that's a tier D investor move). Many investors will disagree with me and say they need to build relationships before they invest, but very few of those people have ever raised capital for your type of business and all of them have invested in a company they've only recently met. So you need to get in there and present a formal pitch.
Otherwise, it's just a social call. Thursday is the best day to meet--many investors don't work on Fridays so you will still be fresh in their minds for the Monday meeting. By the following Tuesday or Wednesday, good investors will tell you why they are passing or what they need to move forward.
The not-so-good ones make you follow up with them and see if they are engaging. Either way, a "pass" is sometimes the best answer--cross them off and move on.
4. Practice on Bad Investors
Raising capital is all about volume, no matter who you are and what anyone tells you. I don't care if your Board says, "We are only going to talk to a select group of five people who have expressed inbound interest."
You aren't going to. You're going to wind up speaking to at least 20 investors, sometimes 5x that amount. I've seen some founders treat fundraising like the bar scene in NYC's Murray Hill on a Saturday night. They punch a clock and go to work and speak to every single person at the bar until they're drunk at 3am and need to go home.
So before you start pounding the pavement with your hit list of hot leads, if you must, talk to the wrong investors first--practice on them. Hear their questions and start refining your storyline. Develop appendix slides you can flip to when the question (which you know is coming) is asked. Capitalize on it as a chance to perfect your pitch.
5. Ask Them the Tough Questions
Start the meeting with something like, "Before we get into my Reversible Diapers ecomm play, can you tell me more about your investing thesis, fund size, deals you lead, and normal check size and approach these days?"
This will (1) be a good ice breaker because everyone loves talking about their business--even investors; (2) help you tailor the storyline and approach based on the response (e.g., if they don't lead, their check size is too large/small, or all of a sudden you really need to push the "AI" shtick of your biz), and (3) provide some validation and credibility for you because only proven entrepreneurs with traction and experience tend to ask such normal questions (while everyone else is glossy-eyed panhandlers and just happy to be in the room).