Lesson: Fundraising Series Seed with Jenny Lefcourt

Step #2 Pitch: Show mastery while engaging audience when pitching

I love a pitch when someone comes in and first they tell me who they are. We chitchat for just a couple minutes and a lot of times they’ll ask me, “Do you want me to pull out a deck or do you want me just to talk?” Which I think is interesting because already they’re understanding that different VCs are different. And then, I always leave it up to them and then whichever way they go, at a very high level, they tell me the story.

They tell me what’s broken. They tell how big it is. They tell me how they’re going to change that world. And they tell me where they’ve started, what they’ve done, how much they’re raising and what they’re going to achieve with that money. And they stay high. Then as I ask questions, they dive in deep. I mean one of my favorite tricks when I was on the other side and I was an entrepreneur, is I had an appendix. So when someone said, “Well, explain to me X, Y, Z.” I’d say, “Oh, funny you should ask.” And I’d pull up that slide and they thought I was a genius because I had thought about the things that they were asking about.

So I think staying high, keeping your audience interested, hearing their questions, and following that energy and that path, is way smarter than the person who comes in and just has so much information that without meaning to, they vomit their information on you. You’re left with a headache instead of excitement for a really big idea.

People should be trying to solve problems they actually believe are problems. That so, it is a problem that is in need of a solution versus a cool technology in need of a problem. So you really need as an investor, you need to know it’s a big market here and that it actually is broken and it’s ripe for disintermediation or it’s ripe for disruption, whatever your favorite word is.

I think that you have to be careful when you’re talking about your business. You have to make the person on the other side of the table care. And what is going to make them care? They need to know that it’s big. They need to know that it’s broken. They need to know that your way is better and your way is realistic.

The other thing is this interesting combination, because you have to have a big vision and that someone can buy into and want to be a part of. Then you also later, have to get tactical about how you’re going to hit these sort of smaller milestones to build up to that big vision. Those two things have to both be believable for an investor to want to be a part of it. With all of my companies, but especially the first two, I could truly speak to the market in very intimate detail. You don’t have to be the consumer of your market, but to know it intimately is very helpful.

When I was pitching Della and James which was the first aggregated gift registry which became Wedding Channel, I had just been married. I knew how broken it was, in terms of, I don’t know that you want to hear my whole pitch but, basically it was this huge industry. The brides and grooms weren’t satisfied because they had to limit themselves to how many stores they could register with. And at the same time, all the guests had no idea where these people were registered and how to go about finding them a gift.

So, we were able with conviction to go in and talk about the fact that people were still registering as if we lived in the '50s but we don’t anymore. And now there’s technology and it could be better. It could be better for the brides and grooms. It could be better for the gift buyers and it could be better for the retailers.

The thing that I can remember so clearly was the investors. This was the Amazon.com days and Amazon was taking over the world. And the investor said, “No, no. You shouldn’t work with retailers. That’s swimming up stream. You need to Amazon.com the wedding registry." And we knew that, that would not be successful.

We knew that because we, I had just been a bride, my partner hadn’t been but attended many weddings. We knew that the wedding world was not ready for that and we were right. We explained to these men, for the most part, about how women think, the traditions and that it was ready to evolve but it wasn’t ready to go that fast into that state. And we were right.

I think it’s a combination of pitching your vision. Really hearing, people ask good questions. Smart people ask smart questions. So you don’t want to be dismissive but at the same time you have to be true to what you know. So the more passion, knowledge, intimacy, you can have about what you’re dealing with, is the better.