Pitch Perfect: Lessons learned from pitching investors.

Advice from Kate Bradley Chernis, Co-Founder and CEO of Lately. Lately is an AI-powered marketing dashboard that’s reinventing the marketing process to give individual marketers and companies the power to create and scale smarter, more consistent messaging.

1. Don't be afraid to be authentically you as well as entertaining when pitching investors.

For a dozen years, I was a rock and roll radio DJ. I programmed all my music. I worked up and down the Eastern seaboard, and then XM was my last gig. What I loved about it was the journey. I learned to leave in the mistakes to make it sound more human. You cultivate a persona of sorts that is still you, but the you that would talk to 20 million people. You have to pretend like you are one-on-one to create that trust. I learned to reveal in a way that wasn't too revealing. A great radio mentor of mine used to say that you should leave space because the listener will turn up the dial to hear if you are still speaking. So, I used to experiment a lot with that. When I started pitching, I was terrified. Then it occurred to me that this is a commercial, and I have done a million of those. I use pauses in my pitching. All those nuances I had learned in radio.

What to do in pitching is practice, practice, practice. I usually recite the pitch 400-500 times before the first one, so it is coming out not memorized. You know it, and you know how to get out of a mess. That is really important. I write it out in my own vernacular and put in my mannerisms, and then I learn it audibly. If you ask a question when doing a pitch, you wake people up. What you don't want to do is drown on and on. You need to be slightly entertaining. This is an emotional sale. I have found that a lot of people that pitch are not engaging with their audience. It is cliché, but it is about authenticity. My authenticity gives people permission to be authentic as well.

2. Don't be polite all of the time.

I learned not to be polite actually which is weird. My mom taught me that you walk in a room and smile. You are kind, you follow up, and all these things. I have learned to be tougher. I will never forget I walked into a meeting once, and I went and shook this person's hand, an investor, and he said: "we are not shaking hands today." I was like, what?? We went through our pitch, and they were all smiling. And, I got up and said you are going to shake my hand now. And he did. It was just this weird thing — investors throw wrenches at you. You want to be likable, but you also want to be stern.

This process is a two-way street. I have something to offer to you, and it is valuable. I expect that to be the understanding between the entrepreneur and the investor.

3. The cat and mouse game of pitching investors.

Make them understand that they are chasing you. It should be equal. With investors, you have to be very careful. Everybody wants a little piece of you. They want to feel cool, but at the same time, they don't want to know the real deal. That is hard because you have to learn what that line is, and it is moving all the time. That is something I thought a lot about in the last six months. How much do I share, how much do I hold back. It is that cat and mouse game. My co-founder who had been in the venture world for a long time kept saying that it is just like dating. You just want to get their number. Finally, I turned to him and said I don't know what you are talking about. When I was in college I didn't need to get somebody's number; I was the girl. They were coming to me. I find that very irritating because I am pretty straight forward and doing that social dance just feels like a waste of time. But, I have had to learn how to do it.

I read an incredible book called Pitch Anything. A sales guy wrote it. He would use psychological, manipulative tricks. That is when I understood the game clearer. It is sort of funny because you want to do the cat and mouse thing which I believe is inherently flirty. That is the deal. I am learning to use that without being sexual in any way. One tip he gave that if you put something in the middle of the table that has the person's name on it like a folder, leave it there. You will find that they are going to try to keep trying to grab it. And then you say "we will get to that later."

One thing VC's do is try to get you off track. You got your pitch, your rolling along and they inject a bunch of questions. I have gotten good at saying "that is a great question; I will get back to that." It is a useful skill. You do it with a smile. There is a lot of power there. That is where the flirty thing comes in. I can wink at you. I can smile at you. I am a fan of being womanly and professional at the same time.

4. Take the credit for what you have built.

I am guilty of saying "we" instead of "I." I had to learn to own the stuff that I created. I built this company. I am the one who had the foresight to see the opportunity. I am the one who got us to $30K MRR. My instinct is "we" because I am a woman, the nurturer. Certainly, my team is everything. I couldn't do this without them. But, investors want you to take the credit. They want to know that you are the leader.