At my last startup, I met with over 400 investors over the course of ten years and raised over $20M. I got rejected A LOT. One of the most frustrating parts was not understanding all the fundraising paradoxes that exist. So here are three fundraising paradoxes I wish I had known when I was fundraising

• The more you look like you want to raise, the less you raise - Don't let your hunger be mistaken for desperation, which can make it look like there’s something wrong with your startup. Always present from a position of strength, even if you don't have any. It's really the only way you’ll get funded

• The more specifics you say, the worse your chances - Unless your startup is absolutely crushing it, treat specifics (i.e., users, revenue) like land mines, the more you put out there, the more likely an investor is gonna ask you 10 questions on it and blow your fundraising chances to a million pieces. During your coffee chats with investors, stay vague but excited, and make them want more. Show them the trailer, not the whole movie.

• The more time you spend fundraising, the lower your chances - Time is your enemy in fundraising. If you’re out in the market too long, investors will start asking, “What's wrong with that startup that hasn't been able to raise money? To counter this, stack all your meetings in a two-week time frame.