The definitive guide to pitching your startup

A recorded pitch-feedback session hosted by Hiten Shah (April 4, 2024). Two founders present: Steve pitching Roster — a vertical professional network/marketplace for production crews (using call sheets to seed connections) — and Michael pitching Spot — a social-media-like app for discovering local spots aimed at 25–35 year olds on temporary visas. Hiten critiques each pitch: he emphasizes concise 10–20s openings, stating "why you" and distribution strategy, tighter problem definition, target user specificity, and authentic storytelling. The session ends with rapid-fire advice on pitching (storytelling, addressing investor objections, avoiding fluff like aggregated years of experience).
Chapters
Today we're going to do pitch feedback.
This is some of the most impactful experiences that I've been able to provide. Many founders, countless founders, they give me their pitch and I give them two different perspectives. One perspective is from investors and like what they would say and the questions they would ask and the impression they would get. And then I go deep into giving feedback on the pitch itself.
Foreign.
Let's jump in 60 seconds. What do you got?
Awesome.
Yeah.
So my startup is Roster. So for a second picture, the last time you watched a movie, movies over, the credits are rolling and you know, there's just hundreds of names scrolling by, right. You're at this point you're looking for the next thing on Netflix. Those names, that's what Roster is all about. So we're talking the production assistance, the cinematographers. Right. So Roster is aiming to be a networked marketplace, a professional networking space for folks in the film, TV and commercial entertainment space could divot and, or like move over to live events as well, which is my background. I've met you before. I worked at Lend with Chris Carver a decade ago. And so yeah, Roster, we're going to leverage, you know, a, a legacy document in this industry called a call sheet that every single production you've ever seen has used. It's got all the people, all their contacts, their phone numbers and, and we're going to leverage that to build out and be the kind of the mitigate the cold start problem and start building out this network space and really help both production side, both sides of the marketplace find value. Right. You know, the folks who have produced a ton of content, who's everyone you've worked with, what roles have they worked in and where are they now? Right. The value that you and I get from a LinkedIn this space doesn't get. In fact, we talk about the Hollywood magic that doesn't actually translate to the day to day.
Right.
They're on emails and spreadsheets just like many other industries. And there hasn't been tech that has brought them into the next, the next wave that we enjoy in the, you know, in B2B and other, other spaces. So, okay, Steve, I've, I've said a.
Lot that was double the time. So that's my first. Like if you were in a pitch and someone gave you 60 seconds, they would have been cut you off at 60. The reason I didn't cut you off is because I wanted to hear more the kind of question I would ask if I was an investor and I heard this pitch, first of all, you got into a little bit was why you? So I'd be like, why are you the right person to build this? And why are you the right team? And then the next thing I would ask about, because this is a industry that's probably unfamiliar with people on the level of underneath the one layer beyond the credits, is like, oh, how are you going to get distribution? What's the deal? Okay, so now the feedback. Okay, you started out real strong, but then you rambled so long and you repeated yourself and all this stuff. But I captured certain things that were valuable there. So my advice for you here is this. Knowing that you worked on a marketplace before, knowing that you worked on an event marketplace that's similar, would be really valuable to the investors to understand why you. Now, let me tell you, Let me tell you what I got that you probably didn't understand, and that's why you kept going. When you say those credits at the end, and these are all. There is so much emotional resonance you could have. Not because I watch a movie, I see the credits, but I watch an amazing movie, I see the credits. I don't care who's behind it, frankly, but somebody cares. And so what you're saying is you're using that to help me understand in my context what the issue is. The issue is those people in the credits are not aggregated like IMDb or LinkedIn. And so to me, this is an aggregation play of bringing a bunch of humans that do a job together in what you would call a verticalized LinkedIn. And I'm not. I'm not a fan of using other companies as examples, but a verticalized LinkedIn in the entertainment industry, for all the people who are actually getting that production done, dude, that's a clear, crisp pitch. And I even know everything you're probably going to do. So the only questions I have are, why you? And what's. How are you going to get distribution? So if you can cut down that first part to 10 to 20 seconds, then you have 40 seconds to tell me why you and what your distribution strategy is. And honestly, you're done.
That's so helpful. And do I get to tell you the answer, or do. Do we have time?
I'll give you another 30 to 60 seconds so you can tell me the answer.
Since Lend, I went on to ServiceNow and then I went to Wrapbook. Wrapbook is the. The kind of the startup for entertainment payroll. They raised 27 million from Andreessen and then 100 billion, 100 million from Tiger Global. So I was their third product. Team hire and really got to see the crossovers between live events and film, TV commercial and really empathize with the space. I'm a product designer at heart, so I think I'm really well suited for this space.
Perfect. So, so those are the things you need to for sure mention. And then, and then the one question I had because sometimes this is helpful, are the people that you worked with, are any of them investing?
We haven't done a hard pitch toward with the co founders. I'm really close with one of the.
Ideally if you can lead with, I work there, it's in the same industry and they're going to invest in us. That's a huge trust point that you need if you can get it because people then feel like, oh cool.
No, it's good. It helps to hear that perspective and I can push for that.
Yeah, go get their money. That's the first money I'd go get for this. So Steve's pitch and his business is one of my favorite types because he's taking something old, stodgy and obviously lots of money and lots of activity and essentially productizing the whole experience because he's building essentially a vertical LinkedIn for one piece of the entertainment industry. You could argue it's the production side of the entertainment industry. So it's really big. And if these people don't have a place to go, discover other people that can help or kind of meet each other in different ways or even like see people's like like constructed resume that's relevant for this. Like what movies do they work on, what did they do, what shows do they work on, what do they do, all that kind of stuff, it feels like a no brainer of an opportunity. And those are super rare. Like I don't necessarily see a ton of folks thinking about problems like that and it's clear that he knows about the problem and he's experienced it in the sense of with the co founder he has who's kind of in the industry and then he's seen kind of the product software kind of side of it. And that's also why I told him if you worked at a company that's in the industry and those founders invest, that's one of the greatest signals he can have. So whenever you have a situation like that where you're going to work in the same industry and the found and you're not competing with the company you're at, it is so much validation for investors to know that those founders of the company you were just at believe in you. So much that they're willing to invest in you.
Hey Michael, how's it going? It's going well. Do you want to jump right in and start with your pitch? Let's do it.
Well, I'd like to introduce Spot, the social media platform turning local exploration on its head. Let's picture Spot as if Instagram, Google Maps and TripAdvisor merged into one seamless experience. Considering there's nearly 5 billion social media users globally and up to 3/4 of millennial and Gen Z making decisions on where to go based on social media content, Spot is tapping into an enormous market. In the last five weeks we've developed a prototype secured 500 early access registrations have been offered a Spot to present at Web Summit Qatar. We're on Track to hit 5000 pre registered users over the next month. We'll be launching our first community event to showcase our commitment to you on how we're going to help you create unforgettable memories. So what sets us apart? Spot thrives on user generated content created by you and your friends. We're empowering you to show off your favorite spots under one roof. From bars to restaurants, activities and accommodation. Not only that, but if you're in need of inspiration, we'll help you discover, share and get directions to new spots based on your interests. As for our revenue model, we disrupt the norm by sharing our IP offering businesses subscription based customer analytics. Unlike competitors, we don't burden businesses with demographic expectations when it comes to advertising. Instead, we provide verified insights enabling targeted advertising to help local businesses tell their story. Spot helping you discover Extraordinary everywhere Based.
On what I heard, I would actually be pretty confused about what you're doing. So one of the biggest things that gets debated a lot is do you use another company's name to to explain your service? And in the beginning you use three companies to explain your service. So I'm in the camp staunchly of you should very rarely say we're X for Y. And I know you didn't do that, but you kind of did that because you're like TripAdvisor and something else and something else. And I already got lost right there because you started with that. I'm now confused and I only remember TripAdvisor. But I don't think your business is anywhere like Trip Advisor except for the reviews and the user generated nature of what they developed is my guess. Right. So in your case, like I would start with what you are and who you're for. That's usually what I'd start with. But in your Case I think is super important because I still don't get it. So do you want to just tell me what you are and who you're for so that I can kind of help frame that a little bit more?
Absolutely. So Spot is a social media platform. Primarily, we're solving the problem for having to jump across different platforms to find places to go. Example, like what you might use Instagram or TikTok to get information about to save you from having to go to lists of notes in your phone to save those. And then we'd tell we're saving you from jumping across to Google Maps to find or to get directions to these spots when you're ready to go there. So instead we do it all in one roof, all encompassing, to save you time and effort.
Got it. So I still don't know who it's for and I would recommend not just for the pitch, but for your business to get more specific on the who. So there's a few angles there, but like, is it for millennials? Is it for boomers? Like, who's it for? And if, if it's for anyone, that's fine, but you're going to run into all kinds of issues. If you really, truly believe it's for everyone, because you got to start somewhere, even if it's a really wide segment, that's okay, but you have to start somewhere.
We've got a pretty specific segment at the moment. I should have expanded on that earlier. So, as a Kiwi, as a New Zealander based in London, we've run into this a lot of problems ourselves quite regularly. And the more we talk about, the more we realize it's such a consistent problem. So our Target Market is 25 to 35 year olds based in London who are here on a two to three year visa. They're here to squeeze every drop out of life, to do everything, to look under every rock and have the most fun they can over the next two years.
It's not really yet defining the problem. And I think you need to define the problem with a product like this because it's too easy to say we're going to put three things together. And I think people will call bullshit on that kind of thinking when you say it. When you do it and it works, there's no bullshit. Fine. Great. It worked, right? Like, like without Flickr existing, Instagram wouldn't exist. But could someone have said this is what Instagram is and convince you it's different than Flickr? Maybe not. Right? It's like Flickr with filters and it's mobile. That's not good enough. That doesn't give people the problem it's solving. So what I love about what you just told me is you help me define the segment in my head that you're targeting, which then gives me a very clear impression of the problems, even if you haven't stated them, especially the way you said it. So it's not for people who are local experts. It's for people who are traveling and want to get the most of out of their travel experience. Now, you could argue with me and say, actually it's for people who are temporarily moving somewhere and they know it's temporary, so they're not going to invest in the area. But they still have this need of wanting to discover new things to do in the area because they're new, so everything's new to them. That resonates with me more and that doesn't get into this whole. It's like this or like that. This is where we got our inspiration. None of that matters. What matters is you found a gap in the market and I as an investor need to understand what that gap is you found and who is perfect that you can fill the gap for. And so usually I could be really crisp and say blah, blah, blah, blah, blah, and your pitch is done and you're good. But like in this case, there's so many nuances that I don't understand by your, even your, your long pitch that like, I could get it wrong, but let me give it a shot. So what you can say is the founders of this company Spot, we moved to a completely foreign country and we did it for XYZ purpose. I don't know your purpose. And as a result we had a problem, but we needed to make sure other people had the problem. The problem is that we have a hard time discovering places and we're going in between tools and social media platforms just to figure out where to go that we will like and enjoy. And it's kind of a mess. So you can even imagine in a pitch deck the slide you would show, right? So that's a problem definition and it defines for whom and it also says we have the problem, but we needed to make sure other people did. The reason I said that and then stopped is because after you explain the problem and all that, then you can go and say, and this is our traction so far. And that's why I said we needed to make sure other people have the problem. Because one of the fears of investors when you say I have the problem is they're Wondering if other people have the problem. And as you can imagine, most of the people you're pitching, they don't have this problem. So you have to educate them on the problem and how hard this problem is to solve today and how your solution is, is what you're kind of going after. And then they want some validation. To your point in your original pitch of telling me all that, that's kind of what it is. And so ultimately, you're building a new social media platform for a certain type of traveler. That's the way I think about it.
Really appreciate your help. Thank you so much.
Of course, Michael. Take care. Now I'm going to do a rapid fire round where I'm going to answer questions from the audience as fast as I can. Let's get started.
First question, do you have any tips for pitching investors over Zoom? Oh, I love this question. Why do you think it's any different? It's not any different. You're just talking to another human being. It doesn't matter if it's over zoom or in person, because everything I've heard from people about, oh, the mannerisms and like, I can't see their reaction and this, that and the other, it's like, hey, you have a story to communicate. It's your story. Own the story. And if you own the story, it doesn't matter if you're in person or you're on a Zoom and you're telling the story, it's your story. You should be passionate about telling your story. Just get good at that. And it doesn't matter how you're pitching. It's probably not the advice you thought I'd give you, but I don't have any tips for pitching on Zoom except get good at telling your story. Is there one thing that all great pitches have? Great pitches have great storytelling. That is an honest, accurate story about you. And that doesn't have to be this whole practiced story or something that you spend a ton of time perfecting. It actually should be a genuine story. So I think the best pitches have genuine storytelling from the founder about what they're doing, why they're doing it, how they're doing it, all the details of it, but it's formatted in a way where it's like their journey. So it's pretty much like, I want to hear your journey. I want to hear why you're working on this. I want to understand you, the human, and your motivations around what you're doing. And that's more important than anything else. That's why I would say great storytelling is really about a genuine journey that you've gone on and your ability to express that, because then people will believe the journey you say you're going to go on next. And that's really what they're funding. What's the most common mistake you've seen when people are pitching investors? One of the most common mistakes I see when people pitch investors is that they try to tell a story that they think the investor wants to hear. So they spend a lot of time trying to perfect all that. I don't recommend that. Instead, I would say that you should focus on understanding what objections an investor might have about you, your team, your business, your market, and use that to talk about anything you want to talk about. Because when you are telling your story and pitching investors, they're trying to find a reason, usually to say no, not a reason to say yes. And anything you share with them should be addressing the kind of objections that they would have about your type of business. And that's their job. Right? Their job is to see many, many companies and fund very few of them. So really, their job is to figure out, is this someone I want to pursue further or is this someone I just want to say no to? Because I'm going to say no to most of them anyway. Next question. So this question is about me as an investor. As an investor, are there things that founders do that make you roll your eyes? Yeah, there's one that I just want to get out of the way. The one that gets me every time is when if they have like five years or 10 years of experience, and then their co founder has another five or ten, and then their team has another five or ten, then they say, we have over 30 years of experience with X. That kind of is fake because you're combining everyone's experience. It's not really 30 years. It's 30 years combined. And then people got to think about this too much. What matters is what have you done before? What is the evidence you have for that and how can you communicate that that's it. It doesn't matter how long you've done it. It matters how good you are at it is actually the truth. And can you show evidence of that? So I think the bottom line of this question is the thing that makes me roll my eyes the most is when people are adding all this fluff to their story and their pitch. When I just want to get to the root of what are you doing, who are you that should be doing that and why are you doing it? And then what are you going to do next and what have you done so far? It's only a set of a few questions that you're looking to answer, but when you're pitching someone and if you don't like, think of it like that and start there, you're going to add so many other things that are irrelevant, and those are the types of things that make me roll my eyes. Obviously some things you should say because they're funny, like how you met your co founder, if there's a funny story to it, or something like that. But overall, if you stick to kind of like the facts and your story, that's way more impactful than talking too much about your past and what you worked on in the past versus what you worked on recently in the context of this business. That's a wrap for the Heaton show and the pitch feedback session today. I might do this again, especially for later stage founders, if you enjoy it. And if you do, please find a way to let me know once you hear this. On that note, you should subscribe to the podcast on YouTube and your favorite podcasting platform. And you can always go to Heaton show to apply to join the next podcast. The show is produced by Supermix. Thanks for joining.
It.
More from Hiten

The Library of Minds: "The Social Network Ruined Startups" | Hiten Shah 4x SaaS Founder

This startup repair factory is worth over $11 billion #entrepreneur #founder #productmanagement

This is how a $40 billion crypto cult came crashing down #crypto #terraluna #stablecoin #dokwon

This is the only casino the government can’t shut down #gambling #tech #startup #founder






