The school of hard knocks is an effective teacher, but not a very pleasant one. While every entrepreneur will inevitably learn a few lessons in its classrooms, if you can avoid too many painful (if educational) mistakes by heeding the advice of those who've gone before, you'll make your business journey quite a bit smoother.

And what's true of small business is doubly true for venture-backed startups, where the competition is fiercer, the pace faster, and the odds even longer. To help out newbie founders VC Adam Quinton recently used his LinkedIn Influencer column to gather up lessons learned the hard way from a selection of female founders, highlighting the things they'd wish they'd known before fundraising so you can be better armed with information before you contact your first investor. Here's a selection of some of the advice on offer:

1. A meeting doesn't equal interest

You're a new entrepreneur with an early-stage startup, so when a top-tier VC agrees to meet with you to discuss your business, you're super excited, right? While that's a natural reaction, it's one that can waste a lot of your time, according to Gillian Morris, the co-founder and CEO of travel app Hitlist. Realism, not vanity, should guide which investors you approach.

"I spent a lot of time trying (and usually succeeding) in getting in front of top tier seed stage investors when our company was still very young--so young that there was no chance that they'd invest. Unless you have a very obvious track record with previous early stage startups, you're not going to get a brand name seed fund to invest in you until you have very solid metrics," she explains. "Before that, they'll be happy to have an associate talk with you and mine information, but they're not going to get involved (which would be too risky) and they're not going to help out. I wish I'd known that at the very early stage, angel investors are the only ones who can really help your business get to the next level."

2. You can say no

Turning down a big fat check may be the furthest thing from your mind, but you really should remember that just because money is offered doesn't mean you need to accept it. "Sometimes you negotiate on terms, sometimes you take a check and thank the universe, and sometimes you walk away. If an investor prove to be a giant pain or it just doesn't feel right, walk. Clarifying what your deal breakers--either internally or with your co-founder, if applicable--makes negotiation that much easier," says Allison McGuire, co-founder and CEO of Walc.

3. Investors are people too

Of course you know the VC sitting across from you isn't an alien, but when you're so focused on the business essentials, it's easy enough to forget that, just like the rest of us, investors have pet projects, personal obsessions and gut instincts too. You can leverage them.

"Investors are not just judging companies by potential returns. They may hear lots of pitches and see lots of companies with promise. But the final decision--the decision on which companies to pick out of a herd--often seems to come from the gut or the heart," Andrea Guendelman and Silvia Travesani, the co-founders of BeVisible, remind entrepreneurs.

Experienced founders, what do you wish you'd known before pitching your first investor?

Published on: Apr 28, 2015