Reena Jadhav breaks down why pitching startups is so hard: investors are skeptical, competition is fierce, and time is limited. She argues storytelling is the core of a pitch and that every pitch must answer three questions: what, how, and why.
Chapters
Thank you so much. That was lovely. Yes, I am a dreamer. And I think if you're going to be a founder, you absolutely should sit under apple trees and dream. OK, well, let's get started. By the way, I'm on Twitter @ReenaJadev. I'm on LinkedIn. If you want to connect with me after, just say I'm a friend. And just tell me that you saw me at Draper University and I'll absolutely be happy to connect with you. And Startup Den is my virtual workshop site for founders. So we're gonna talk about pitching today. Pitching is really, really hard. In fact, of all the things that I've ever done in the last— I think it's been 18 years now since I've been doing this— pitching has actually been one of the hardest things that I've done. And why is it so hard? In fact, You know, I think back and I, I look at every time that I've gotten butterflies and sweaty palms and all of those experiences. It's actually been when I've been pitching, not negotiating, not hiring, not firing, not fighting, not arguing. None of those things have made me as afraid as when I'm actually pitching. Why is it so hard? Well, first of all, it's really hard because the listeners are skeptical. So you gotta start with the assumption that people that are gonna be listening on this side of the table, as I call it, they are skeptical. I didn't get that until I crossed over. I'd always feel, you know, I would do my pitch and I'd be so excited and I'd think, of course they'll be writing out the check now. And, you know, I'd see confused looks and kind of head scratching and head bobbing and I'd go, why don't you understand? This is such an amazing idea. I'm revolutionizing something, something. For example, my second— my first startup was mobile messaging. We're gonna allow you to, you know, get tasks on your cell phone, and it was built on WAP, and you're gonna be able to do all these things. I had a lot of skepticism failing— facing me. Why is that? Why do you think there's a lot of skepticism when you pitch? We're gonna make it interactive, by the way.
Because a lot of people are great at pitching but really terrible entrepreneurs, so you don't want to trust necessarily the people who are good at pitching.
That's one reason there could be skepticism. Oh, yes?
Execution is hard.
Execution is hard. It's even simpler than that because far more companies fail. I was talking— so I'm also setting up an incubator in Berkeley and I was talking to one of the other managing partners and we were joking. He's like, I'm so cynical now. I am— I just don't believe anything anyone tells me anymore because I have failed in so many investments. I failed as many times as I've succeeded. The ones that I thought would fail The ones that I thought were gonna succeed failed. And he's one of the Midas touch guys. So what you realize is that as an investor, it's actually really hard to predict success because it's a combination of so many moving parts, from execution to timing to market momentum to luck, serendipity. So there's a lot of skepticism when you walk in and say anything 'cause most investors have heard it all and they've probably seen it not work as well. So that's one reason. So you wanna go in knowing that they're looking at you a little skeptically. You wanna start there. They've seen and heard it all. It's so funny. You walk in and you go, this is— I'm special. This— no one else is doing what I'm doing, guaranteed. And you know what? There's— the numbers are there's 7 people at any given point in time that are either thinking or doing whatever it is that you're trying to think and do. So assume that there's competition. Assume that there may have already been competition that didn't succeed. And that's the ADD, right? Who talked about so little time, so much info, so little time, so much info, so little time? Even when you get an hour with an investor, you always feel like you're running out of time. There's never enough time. Can you give me advice on how you try to talk fast and then other people, they're not able to catch up?
Then I go to dinner and everyone's like, oh, you're talking so fast, you're not able to catch up. And I'm like, I want to squeeze in all the info in just 1 minute. And how do I bring emotion and just make them understand what's going on, the points in just 1, 2 minutes? Did you hear that?
1 minute is very hard to get everything you want to say. So poor thing, she— what is your name?
Maha.
Maha. So Maha learned the trick of speaking really fast. And that didn't work very well, did it? Speaking faster doesn't help. You know, drinking coffee and being on a fast train doesn't really work very well because then you're not really connecting and resonating. So here's the reasons why it is hard. You can't change these. None of these can be changed, meaning you're always gonna be stuck with a skeptical audience. You're always gonna be stuck with the fact that they've heard it before and they've probably seen some other people doing this, and the fact that there's gonna be so much information that needs to be shared in very little time. So my goal, hence, is to help you craft a winning pitch that wins over the investors. Now, that's what we're gonna try and do over the next—
2 hours.
45 minutes or so, gets you new team members, convinces the targets that you're a must-buy. Your pitching is not just about investors. I know we're talking about the pitches primarily today from an investor standpoint, but keep in mind the art of pitching is applicable to hiring, recruiting team members, to getting customers to buy from you. And frankly, if you've got customers buying from you, all those reasons on slide 1 kind of go away, right? Skepticism, boredom, ADD, who cares? Your numbers are to the right and up. So pitching, just keep in mind as we're going through pitching today, these don't just apply to investor pitches. These actually apply to customers as well as recruiting and any other place you may want to pitch. For example, trying, you know, proposing to your spouse. OK. So what's your pitch? What is a pitch? I've heard different people say different things. But what really is a pitch? It's the most important emotion-evoking story that you're going to tell. It's a story. It's not a listing of facts. It is not a clinical, you know, cut-and-paste section of the 5 things you want to tell someone. It's actually the most important story you're going to tell. Not all of us are Not all of us are born internally creating connections, but if— how many of you enjoy watching movies? Wow, there's a lot of people who don't like movies here. So if you do enjoy movies or sitcoms, notice how they build out the story. Notice how there's always some level of suspense, some level of climax, some thrill. You've got to tell a story. A good pitch answers believably 3 questions. What are you doing? How are you gonna do it? And why? Why is really important. The journey for entrepreneurs is a long one. It's a marathon. It's a 7 to 10 year cycle. And if— obviously some of you are gonna get really lucky and exit out in 6 months, 1 year, 1.5 years, 18 months. But for a lot of you, it may not be that short of a journey. It may be an Airbnb or a Pinterest or a Zappos. Multibillion-dollar valuations 10 years later. You didn't want to ask them how they were doing in their first 3 to 4 years, right? So really important is why are you doing this? Why are you embarking on this journey and what kind of commitment do you have? So those are the 3 things that your pitch must answer very believably.
