The Exchanges

Q question for you is, For founders or future founders that are listening to this today, and they're wondering, okay, there's a lot of good stuff here, but if there was one or two specific things that I could do or implement today to improve the quality of my pitch or improve the probability that I'm able to raise money in the future, what would those one or two things be?

A I'm gonna give one that's super, just like specific and tactical. And this is one that is really challenging for people. It's how long should a story be? And I think a story when you're telling the vision story, it should be about three minutes long. Three minutes for anyone out there is about 600 words. Um, it's, it's a little bit less if you're speaking slower, but many founders tend to speak fast. So anywhere between 500 to 600 words is about three minutes. That's the first piece is like, that's very tactical. Don't, don't build a story that's going to take you more time than that. And what you should do when you build that story is go through the process of practicing, practicing it, refining it, internalizing it so that you can say it no matter what's happening around you. So that's kind of piece one that I would say. And piece two is remember the frame that you're wanting an investor to be looking at the deal through. And it's this, what if I'm right? And what I find many founders try to do in investor calls is they try to prove to the investor that they're right. They're trying to make them say with a hundred percent certainty, Robbie, you're right about the thing that you're saying in the future. And I tell founders, you can't know a hundred percent what the future is going to look like because things are going to change. Things are going to happen. Right. And the examp…

AI assessment note: “when you're telling the vision story, it should be about three minutes long.”

Q picture because you're selling Basically the investor on the future and why they trust you to attain that future, but then you start talking about whether it's series A, series B, and I think at least the story that people have in their heads is this is where metrics start mattering more. This is where financials matter more. How do you see the startup pitch evolving as your business evolves?

A It does evolve, and that is one of the traps that many founders fall into is they rely on the story that got them there and thinking that it's still going to work at the Later stages. And the reality is it doesn't. It's just like you as a person grow, you evolve, and the same should be true for a story. At the beginning stages, right, the pre-seed seed, you don't have a ton of metrics, but you still have some metrics. You need to be able to use data to back up the world that you're talking about. And that really comes down to understanding how to frame numbers correctly. I always say this numbers on their own are meaningless. I can make numbers say good or bad, no matter what. And this, you know, comes back from my background as a trial lawyer. In every case I tried, the facts were the same, but the way the prosecution me positioned, it was very different from how the defense positioned it. The facts were still the same, just like the numbers are the same. Numbers mean what we say they mean. So even at the early stages, you need to have some numbers, but they're going to be more about the opportunity size. Right. Whereas the numbers you're talking about in later stage is going to be the numbers of your business. It's going to be all those metrics that we're talking about, right? LTV, ACV, CAC, all the things that you've got to be able to explain and say, Hey, this is why we see…

AI assessment note: “It does evolve, and that is one of the traps that many founders fall into”

Q Yeah, man, I love that. Um, okay, so let's talk, you talked about what, A good pitch and a good story, uh, irrespective of stage looks like. Let's talk about some of the biggest mistakes you've seen. When, when founders really botch pitches, what are the most common things you're seeing in what they're saying or what they're sharing?

A A couple things. One is a lot of founders make the mistake of not sharing anything about who they are as a, both as a person and as a founder, which I think is One of the biggest mistakes that we see, a lot of founders think that investors only care about like the business side of a founder, and the reality is I want to know also the things about who you are as a person. Investors want to know that. We can learn a lot about someone if they were a competitive gamer growing up. We can learn a lot about someone if they did debate. We can learn a lot about someone if they're an immigrant and they speak five languages. Like we can learn a lot about Whether or not they're going to succeed based on who they are as a person, even if it's not directly business related. So I think a lot of founders make the mistake of thinking investors don't care about anything about who I am. I just want to focus on business. And what that does is it puts the investor into the logical brain side because all it is now is a business transaction and a business transaction is going to be much harder to prove because they're seeing so many business transactions and business transactions. You look for red flags. When we like somebody, when we believe in them, when we connect to them, we look for green flags. We look for reasons to say yes. That's just human nature. And so that, that's kind of piece one. Piec…

AI assessment note: “One is a lot of founders make the mistake of not sharing anything about who they are”

Q a lot of, kind of, introverts or people who are more reserved in nature worry about, like, is there one way to tell a story well, and it's very, like, you know, it feels like, you know, a better version of the used car salesman. What would you say to people who are more reserved or introverted in nature and how they can still be really good storytellers and pitchers?

A I've worked with a lot of founders. I mean, you know this, the founders I've worked with, we've raised six hundred million dollars so far in capital, and I'm gonna tell you right now, not a single one of them looks the same. They all Communicate very differently. Some are very charismatic. It's effortless for them to carry on a conversation. Others are like way on, on the end of the spectrum, super technical, don't like talking to people. But what we do is we lean into those strengths. So we just create the, the training ground and we help them understand like, what is an investor looking for? So that they understand the process, whether they're extroverted, introverted, anywhere on that spectrum, what's an investor looking for and how can you show up in that way to deliver it to them? And so the technical founders tend to be much more like they kind of follow a, a program out in their head. They know that if they say this, then I say this, if they say this, then I say this. And it's like, that's great. Do that for the ones who are more comfortable and at ease and flow. We're like, Hey, just kind of like carry on a conversation. See where it goes. Don't be afraid to go down rabbit trails. Like you have that level of mastery of communication. Great. We do that with them. And the ones in between were like, Hey, let's kind of blend. Let's blend these two. So like on certain topics…

AI assessment note: “what we do is we lean into those strengths. So we just create the training ground”