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80 | Your 5-Minute Investor Pitch Litmus Test w/Ali Dastjerdi

42m 15s

80 | Your 5-Minute Investor Pitch Litmus Test w/Ali Dastjerdi

The discussion emphasizes the importance of finding the right investor fit early in the fundraising process. The guest, Ali Dijardi, co-founder of Rayleigh, advises founders to research investors' portfolios and tailor their pitches to align with past successful investments, as this increases chances of interest. He warns against confusing investors' curiosity with genuine commitment, noting that investors often enjoy learning but may not invest. Rayleigh addresses the inefficiency of traditional sourcing by allowing investors to define custom theses in their own language, using AI to discover niche companies that match. This approach helps investors differentiate themselves and find less competitive deals. For founders, being discoverable requires only a public description of their business online. Current investment trends show a split between AI-focused moonshots and capital-efficient vertical software, with less funding for other large-scale ventures. The platform serves VC, growth equity, and private equity firms, helping them find companies that align with their unique criteria.

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Okay, welcome back. If you are struggling to get investors to take the next step, it's probably not because your ideal investor doesn't exist. And in today's episode, we're going to show you how to tell in five minutes if an investor is the right fit, if they believe in the same world that you do and what to do if they don't. So our guest today is Ali Dijardi, co-founder of Rayloo, which is an AI platform helping investors discover and build relationships with companies they actually want to back. So I'm super excited to hear about that because I think we always want to understand how investors are looking at companies and what they're looking for. And in his early career, he spoke with over 5,000 founders so he knows a thing or two about pitch decks. And he has also since raised both a seed and a series A round for his own startup made tons of near-death pivots along the road to product market fit. But he is at a point now where they are hiring for nearly all positions. So he figured out the method to the madness and is doing something right. And he's going to talk about what most founders get wrong about pitching. Why selling yourself is everything and how to keep your team aligned. So let's get into it. Ali, welcome. How are you? Good doing well. Thanks for having me on. Yeah, very fun. What a wealth of knowledge. It sounds like you are so I'm happy we finally connected. And I think this sounds like a really cool platform that you've built. Where are you at today? What's keeping you busy? Yeah, we are in the fun part of a startup where we're growing in every direction possible. We're you know, they always when you're in the early days of starting a company, you always wonder what product market fit will feel like. And founders are a little bit further down in the journey. Say like you'll feel it. It's a wave. And at the moment, we're currently in that wave phase. We literally have more people who want what we do than we can service. So that's where we're at. At the moment. That's like that's better than landing a huge round of funding. You know what I mean? That's like sustainability and growth. Like that's what you're in need. That's what you need. So congrats. That's amazing. Thank you. It was it was a circuitous journey to get here. But it's awesome to be at this phase. And I mean, I think the fun of startups, I mean, there's lots of things that are fun about them is that at every phase you have new challenges and new things that keep you up and ask you to do different things. And yeah, you know, definitely underwater with all the work that we do. But it's always one of those moments where I say, you know, about a year ago, I would give anything of the world to have the problems I currently have. So I got to keep that perspective. Isn't that funny how that works? It's like you reach a goal. And then it's like, but it's like, oh my gosh, look how far I've come. So yeah, that's very exciting. So before we get into, I want to hear a lot about your story. So obviously you've been through, you know, the all the trials and tribulations that go with, you know, launching and growing a startup. But let's talk about, you know, previously you working for a VC, being exposed to, you know, tons of founders, what can founders do to find out, you know, if they are talking to an investor that's a good fit for them. Because I think this is such an interesting thing is so often entrepreneurs just assume any investor is a potential fit, but that's not the reality, right? It really is like a matchmaking thing. You got to find the right fit. So from your perspective, like, what can people do to identify if it might be a good fit, like right out of the gate? Yeah, that's a good question. Yeah, this discovery process is very imperfect. And, you know, over time, there's all sorts of tools that have been built for founders to maybe help them narrow down, you know, from like a traditional crunch base, et cetera. But some of the advice here is simple. It's like right stage category. But I think people, one, don't spend enough time looking at the portfolios, a particular fund, a fund invested in in the past is usually a pretty good indication of what they'll invest into the future. And especially if things went well or poorly for those investments. So if a fund has a few winners that look a certain way, there's actually a very big chance that they will back something else that if you squint hard enough, looks like it. And that can be all sorts of different things. It could be that they have the same business model. So maybe it's that there's a maybe the same go-to-market wedge. Maybe it's the same network effect. It doesn't have to be the same thing. And it almost never is. But it's kind of the squint that they look similar. And one of the things that a lot of founders early on in their journey, sometimes these days ask me for help on pitching. And the first thing I tell them is, well, you should not have a pitch for every fund. Your pitch is very distinct to the fund and person you're speaking to because the story has to be the story that they want to hear. If you are talking to an investor whose biggest win was a story because the market was really big and they were the first entrant. And you should tell your story that way. And if you speak to another fund whose biggest winners are because enterprise sales execution was just incredible. And they just hit the ground and they were grinders. Like you should tell your story that way. But it is a game of identification and a game of reps. I think the biggest thing I have to tell other founders is like it's a for sure volume game. And it's important to figure out where to spend your time and not where to not waste your time, I would say. And one of the things that I used to always think about when I was back to as a VC fund as an investor is it's really cheap for investors to ask more questions and to spend more time like is our jobs to do so. And so we'll do a lot of it. And also, you know, most investors are inherently very inquisitive people. Like I remember when I first got a job at a VC fund, I asked why do you do this? And he said, you know, I love talking to founders and they teach me about things. And those are awesome. But it doesn't mean they're necessarily want to invest. They just like what they're learning and they enjoy the idea of learning. And so it's important to kind of figure out if you're talking to the person that's interested in a more material way really quickly. Yeah, that's such a good point. I think two things there. One, it takes time and you have to be willing to dedicate the time to research the background of who you're talking to. Like this is not a five hour a week, you know, process. Like you got to be willing to really put in the effort and it is time consuming to do it right. And I think, yeah, passion is also contagious, right? And when an investor is someone sitting there talking with a founder and there's, you know, it's obvious they're so passionate about what they're doing and they're all in. Yeah, it's easy to keep engaging, but you can mistake that for interest, the real interest, right? Which, yeah, you can go down a lot of rabbit holes and waste a lot of time doing that, which I have done. Tell us about then. So I think great advice. Like do your research on who you're pitching. Find the angle that interests them by, you know, past investments. I think that is just gold. People should definitely be doing that. What does Ray Lou do then? So how like, where's the struggle? Because I think a lot of times it seems like there's way more entrepreneurs looking for funding than there are investors, right? And, but basically the platform that you have says that investors are also having a hard time finding the right fit for them, right? Which I think is really interesting. So tell us how did you, you know, stumble upon that discovery and realize it was such a pain point that you decided to build this platform and then how does that really serve investors? Yeah, it's a good question. I'll start off with a little bit of a history of how investors and tooling and data has existed here. So essentially in the past decade or so, almost every fund kind of took on open, I've described as a data-based approach to finding the opportunities for them. And there's a lot of different ways to slice and dice it, but the end all be all of that data is some indicator of either momentum or excellence. And these are databases that investors will use that'll show, hey, this company is hiring a lot. This company has job postings. This company has maybe other investors invested in it that we think are strong signals. Maybe this company has a founder who has a background that is in a very strict mold that we think is exciting in some way. And so that's kind of how a lot of investors for the past decade or so have found their deal flow in many ways. Obviously this is what I, this is kind of what I would describe as proactive outbound deal flow. There's obviously the whole universe of just inbound many investors side networks. They cultivate those networks. They get warm leads. But when it comes to investors trying to find stuff outside of their own network, that's typically what they've done. Rayleigh was a little bit of a response to a lot of issues that basically came from that kind of sourcing. The basic idea is that if you start to look for these signals every fund on earth started to look at the same signals and the same molds and the same data and they bought the same data from the same data vendors. And so for the investors, it became like a very difficult problem to decipher signal from noise, but also just even to get in front of companies because some companies would be getting inundated all in the same day, all from the same, all from 50 investors because some database that covers companies for investors flagged something about them. And so Rayleigh was a different response to how sourcing we think should be done, which is a lot more aligned with how investors actually think. We describe ourselves as a somatic sourcing tool. The way that Rayleigh works is that you as an investor come in and say, hey, I'm interested in companies along this thesis. And that thesis can be, and we get all sorts of interesting things. It can be everything from, hey, I'm looking at, you know, novel technologies for crop monitoring. And they'll explain that that could be satellites or drones or airplanes. It could be investors say, hey, I'm interested in niche vertical software. And that can be everything from flooring to forests to everything in between that I want to build software, you know, find niche vertical software for. And so the way that Rayleigh works is that investors literally in their own language. Some investors come with like a whole paragraph, some come with like a few words, explain to an AI agent. This is the type of stuff that gets me really excited. And we basically construct AI agents that traverse enormous quantities of company and public web data and people information to essentially find companies that meet the mold, no matter how niche precise it is. And so it's a little bit of a kind of turning around of this process, you know, instead of just lagging indicator, who's hiring, which, you know, by the time someone's hiring, They probably raise capital and it's probably to say it. It's not that useful to instead truly explain to us like what is a type of business that you, you know, maybe you think space is the next frontier and microsatellites matter to you and maybe you want to find other people that are leveraging usages for that. Explain that to us. Maybe you're looking at more traditional industries. You want to find food and beverage companies that are looking at low ABB alcohol. Maybe that's interesting to you. You can explain a particular thesis and we find you every company that does it and continually monitor it for it. Wow, that's amazing. So as the entrepreneur, as the founder, the small company, what kinds of kind of presence do you have to have and where for them to be found, you know, and kind of picked up or highlighted or used on, you know, platform? That's a good question. Somewhere on the web, you need to have explained what you do is the line. So the lowest threshold there and probably the earliest we ever find companies is either A, you're on like, then you've kind of said, hey, I'm stealth or I'm starting something new or something like that. But at the very least underneath that or somewhere in your header, you explained what you're starting. So we won't cover you if it just says doing something new. If somewhere you have a public web page that just says here's our stealth site, but like we're working on space products, we'll find you. And then a lot of companies, even before they raise capital, sometimes build a crunch base profile for themselves because it's a way to get startup credits. Like I remember early days of our company, like one of the ways you can verify the people who give you free software as being a startup is to have a crunch base profile page. And so that's also the other way that we'll find you as you register a company entity and crunch base as a universe. Yeah, as soon as anywhere on the web you explain what you're doing, we'll find you. Okay, so not hard. Yeah, that's amazing. And then what kind of criteria? So let's just say, you know, such and such company pops up in your, you know, in the research. What, what kind of criteria or, you know, is there a criteria that has to be determined for it to kind of make it through the filter? Or is it just like that it gets matched with the investor and then it's on them to kind of find out more and figure out if it's fit? Yeah, that's a great question. A lot of really, because we're not a traditional data product, is that we make sure that our AI agents construct data in the way that our customers, i.e. investors, want to filter and view the universe. So I'll give you a simple example. Some of the incumbent tools in this space have a strong founder tag. And what a strong founder means is that, you know, you can think of your own tropes, it's like certain schools, certain places. And that's, it's really static. Like, it's that and they tag some companies as strong. And we work with a lot of funds who say, we don't, that's not what we think a strong founder is. Like, for example, it matters to us if the founder is building a company in a space that they worked in before. Like, that is the most important indicator to us. Not that they went to a certain business school, for example. We meet certain folks who care about how many years of experience they have versus not, maybe some funds are indexed towards younger founders versus older founders. Every fund has like a pretty distinct vision. I still like, what is that archetype of a quote unquote, great founder? And you know, I don't know how a little bit is discernible from public web data, but some of those indicators certainly are. And so the way that really works is that for each of those customers, when we build them a custom thing about as a column of data, that's great founder and the criteria that's to find out what great founder is is custom to each fund. So that's both what we love about what we do is that we try to get closer to this matching problem of, you know, if we labeled great founder as a great founder to every fund on Earth, they're all reaching out to the same people who are already probably have enough people reaching out to them. There's a lot of funds who have a pretty distinctive viewpoint on like things they look for. In the end, money is the least differentiated thing on planet Earth. And so VC funds have to be differentiated and how they find and do everything else. And funds have a huge incentive to be differentiated to not go after the same deals as everyone else. And they use us to essentially build tooling at scale that helps them do that with it. Got it. Amazing. And what level of investors? So angels, VCs, anybody, or is it mostly kind of VC firms? It is a little bit. So today, I mean, mostly by like a capacity perspective, we sell to VC funds. So everyone kind of in the VC growth equity universe, we sell to, we sell to a lot of traditional private equity funds too. Believe it or not, the same problem exists for the folks who are looking at commercial HVAC businesses have the same type of problems too. Interesting. Yeah, that is very cool. So from like what you're seeing at a really high level funding and obviously you've been in this world for a while, are you seeing any investment just in general pick up or slow or people are cautious? Like what are you kind of seeing in the? And I'm a believer that where there's a will, there's a way, despite what's going on in the market and everything. So I don't think it's a deterrent one way or the other, but I think it's just interesting to kind of see what the trends are. Obviously, AI is a big one, which could be slowing a little bit, but we love your perspective on that. There's all sorts of different perspectives we see, but I'll maybe point out two trends that we see more than than others. One is the simple one. It's AI. Like we do have just a lot of customers who look for AI destruction in the different markets. I would say the other genre is a lot of especially in the VC market. We see kind of like a bifurcation. Like you're either chasing the really big, really expensive, really flashy things. And most of that capital goes to AI at this point, or you're kind of fatigued from that, or it's not a part of your strategy for one reason or another. At which case, you're looking for the types of stuff that are what I've described as like capital efficient, fast growing, and fast to liquidity outcomes. So as an example, we see a huge amount of focus on vertical niche software, like a truly extraordinary focus. And I mean, these niches, not to criticism, I mean, like we're a vertical niche piece software. We make software for private equity firms and VC firms. Like we're in this boat with you too, but you'd be shocked by the types of industries and things that I've never even thought about. There's a, you know, everything from, you know, cattle, like the entire genre of like cattle management, trucking health to literally like flooring, like vertical software for flooring to elevator inspection management software. You know, I don't say needs to be disparaged again, just saying there's a whole universe. And so we have seen a really big uptick in people who are interested in backing outcomes like that because they're capital efficient. There's a lot of private equity buyers who eventually want to purchase and roll up these businesses. And so you're not looking at 10, 20 year outcome horizons for liquidity. You're looking at much smaller windows, you know, AI and just AI code generation has made it a lot more code efficient to capital efficient to build these kinds of businesses. So especially in software and venture, we see a lot of that. I will say the last thing we'd see is that there is a lot less money flowing to moonshots, not an AI is probably the last inverse I'll say. So a lot of the funds who are willing to deploy capital to things like novel medical devices, to space, to autonomous vehicles, kind of larger moonshot type projects that are capital intensive, lots of capital before you see revenue, less willingness to devote capital there because I think the end added there is like we can either give money here or like I could just go buy more Nvidia stock is like a thing that people will ask themselves and it's like maybe I should just go be a buying like if I'm betting on a moonshot might as well just bet on a GI and so yeah, I would say bifurcation to either niche hyper capital efficient businesses or money moving to the moonshots and that's almost always AI. Yeah, interesting. Okay, thank you. So one more question then I want to get into your background for the many, many entrepreneurs who do what I did and pitch to VCs way too early. What are you seeing as the threshold like a lot of VCs, they say they invest precede. I think tech is obviously different than you know consumer product goods. What are you seeing as the earliest stage and any early signals that VCs are willing to get involved at that stage? And for the entrepreneurs who are not there yet, any recommendations on finding aligned angel investors who kind of are the right fit for them to you know get to that next step to be VC ready. Yeah, totally. I'll give some piece of tactical advice. I these are not novel for me. These are from friends that I know have also helped us when we raised the first thing I'll probably say that maybe most a lot of founders don't know is the first people you need to get on board is an angel not an institutional investor. When you get started raising any round, you need some anchor of credibility. It is a lot easier to actually get that anchor credibility by getting an incredible angel to back very small. It actually doesn't matter at all what the size of that check. The first angel who said yes to us, I think wanted to put it a $10,000 check, like a tiny quantum of money to have a real raising. Really? Okay. But it meant that this person who is a founder who had a successful business who has a name brand in a relatively insular industry, that name brand was associated with our race. We could say, "Hey, we're raising." And as we would say the name of an angel, we'd say, "Hey, this angel, we've got this." It is a very rapid way to build momentum, to open doors. One thing is just to ask the angel to introduce you to a few funds that they know and they'll almost always do it for you. But the part of it here is just like if you can name drop three angels that have decided to be in the round before you have the first conversation with institutions, you will get a lot farther with a lot of funds than you would without them. For a lot of angels, it's probably easier to pitch them. To be honest, most angels are founders. Founders have a much greater risk appetite than VCs do. And so, yeah, the first thing I say is like first go after the angels, not to actually raise capital from them because they're probably not filling around, but to get their credibility and stamp and approval associated with the round that you're raising is like a night and day difference in your ability to get the round together. It's the first thing I would say. Second thing I would say is just volume. I know I said this before, but I'll get a little bit more specific. We, when we were raising our seed round, we probably. probably raised our seat round too early. We probably did it in some not so great ways. I mean, it worked in the end, but I did 160, and looked back at this, on 16 meetings in 30 days, to raise that round. - Wow. - How much for raising? - We were raising about, we were trying to raise like a $3 million seat round, and it ended up being a $4 million round, but we were raising a $3 million seat at the time. And we talked to a lot of people, and that volume matters, and by the way, volume and speed matter. So as soon as investors know that a round has been, quote unquote, being raised for too long, it starts to create negative signaling. - Uh-huh. - And so if you're gonna raise, like someone needs to stop doing anything and everything else, it could be, you know, at the time, my two other co-founders did everything else, and I literally told them like, I have nothing to do with the business anymore for these next 30 days, like I am just raising capital, and I did not sleep for 30 days. But the speed factor matters a lot, because if it takes a long time, people know. Like people will hear from other people, like, oh, you, I met, oh, you're looking at this, I met them a month ago, and as soon as an investor hears that, they think this is negative signaling too many people that passed here, like I don't wanna touch this anymore. And so I would say do a lot, do it very quickly in a compact phase of time, is the other thing I would say. And then lastly, it's about the like, no which investors are interested or not. My biggest take is that you can never convince investors something that they don't already believe in. And I know that sounds counterintuitive, but DC's almost always only back things that they already believe. And your job in that conversation is to paint a picture about why you fit into the mold of the thing they already believe. And sometimes it's not possible, which is okay, and you can move on from that person and keep pitching other investors, but the core job in those first five to 10 minutes is not to haggle with them about whether or not your tam is big enough. Like if there, actually, there's a certain series of questions that as soon as they're asking, like you know it's over. Like if they're pushing back of, is this market big enough? The conversation's probably over. If they don't like your market, like you're not convincing them that it's big enough to support it. If they're pushing back heavily on you as to like, can you do this? Like is your founder, is your co-founder good enough or are you good enough at doing it? There's conversations over it. Like it's never gonna get from point A to point B. Questions that indicate to you, like they get it, is that very on early on in the conversation, they will probably stop you and say, I get it, like you're thinking, X, Y and C, I like this, this, and this. Here's my tactical questions. How do you get your first customer? How do you, what's the wedge? What is the good market model? Like how are we gonna think about long-term gross margins? That's how you know that they are actually interested. As soon as they start asking you questions about the big high-level stuff, team, market, you know, is the product possible? Is there differentiation against a group of incumbents? As soon as they're asking you the really like first level of questions, there's like a incredibly low likelihood you're gonna get very far with that person. If the people that are gonna get cut you a check, very quickly, like in the first five minutes, they will nod their way quickly through all of those things and they're gonna say, okay, I'm gonna do my like secondary level of diligence here. Like let's get a little bit more tactical. Let's get a little bit more specific. And that's how you know which ones are actually interested in what you're doing. Last thing I will say is that if you're talking to someone and they push you too hard on momentum, so like how many customers do you have? How much have you, like questions that are a little bit too tactical about sales, or like are you further along enough? How's it they invest in you are very low unless the answer to those numbers are crazy good? Like if the answer to those numbers are anything but below your socks off, they're not investing. 'Cause like invariably a company is always too early. Like, especially if you're raising a C or a pre-C round, like if you're getting asked questions about how good are certain sales numbers, again, unless it is the answer to your question is jaw dropping, it's always gonna be not good enough. And you're just talking to the wrong person. 'Cause at those phases, I mean, even in the Series A a lot of times, there are investors who are backing team and market, that's about it. - Yeah, wow. - So if you're getting really in the weeds on financials or revenue with someone early, that early on, it's really unlikely unless your answer to those questions are jaw dropping. - Yeah, oh man, that is all such good advice. So I just wanna kind of touch on a few of those things. I think the advice to, you know, someone throwing in obviously money, wealth is all relative, right? But somebody, the reality is there are a lot more people who are willing to part with $10,000, would then say $500,000 on a high risk thing, right? And so even if you're in a food and beverage space, finding a previous founder who grew their company, like you said, and hey, just throw in 10 grand or commit 10 or 20, that is really nothing. All they have to do is just like you and believe in what you're doing and you can probably find people. So I think that's such great advice. It doesn't have to be this K, K minimum amount to invest. So that is just really great advice. And I think yeah, having that, you know, whether it's a lead investor or just somebody who is that credibility, you know, person is definitely key. I think the other thing too that you pointed out is, you know, for you with your background, which we'll get into more in a second, but I mean, obviously you have got a much more expansive network in this space than a lot of first time founders who haven't worked in BC, right? And you still had to have dedicate over 40 hours, you know, 24 hours a day for 30 days in 160 meetings to get that round together. So I think that goes to show like if you don't have that network, you really just need to set the expectation that you've got to put a bunch of time and effort into this. And I totally agree with like, you know, if you're still raising six months later, three months later, it doesn't look good. And there's ways to finesse that, you know, and network ahead of time and then open the round and then have, you know, be ready to close it. And I had never say you're raising until you're ready. You build your whole network and then say it. Don't say those words do early, absolutely. - And the last thing too, I think you really pointed out, 'cause I see so many founders who, you know, start pitching and they go right into all the basically detail of the product. And exactly what you were just saying, that should be that second layer of questions that comes up if someone's interested. Like if they're interested at a high level, let them then ask those questions, but focus on the market, the team, position that the right way to get their interests. Like don't go down a rabbit hole on how your thing works, you know, until you know they're interested. So I think, and to hear that that's the same at the VC level, this really impactful, 'cause it goes to show it's not just at that, you know, very early angel round. It's kind of across the board. So let's pivot and hear about your pivots because you went to Harvard, right? So you've got that, which I love is, you know, just I feel like it's, is a thing and it's not a thing, right? So, you know, it's like having the great degree is amazing, but it also shouldn't stop anybody in their tracks. But how early on, like, did you know it well you were at school, like in that environment that you want to be in this space or what sparked your interest in VC and entrepreneurship and all of that? - Yeah, it's a good question. I'll tell you the stories. Before I was becoming a senior in school, that me and my college roommate at the time, Nathan, tried that summer to like build a whole bunch of businesses together, totally unsuccessfully. And by the end of the summer, come August. He and I looked at each other, we're like, we have to go get real jobs, huh? And we kind of said, yeah, and then tried our best to look for crude and figure out where to get a job right out of school. And Nathan went to Amazon. I went to a VC fund. I'll explain why I went to a VC fund. It was honestly a lock into an extent. There was an alumni that I knew, who was a mentor to me when I was a freshman. She at the time was a senior, pulled my hand through to the fund that I went to. And if it wasn't for her, there was no shot I would have gotten that job. So I owe a lot of that to her. She just said, hey, like I got like let me help you here. And she was a really helpful person. And the reason honestly that I really liked the idea of joining BC is that I knew I always wanted to go back to building a business, but I felt like I wasn't good at it. And there's all sorts of different ways to get, quote unquote, good at being a founder. And there's probably no real paths to doing that. And there's probably no feeling of it for being good enough to be a founder. At the time, the like options in my mind were, well, what's better than just wanting to join a startup. I had a friend who had recruited the year before to try to join a startup and had one of the most miserable experiences, which I now understand. As someone who runs a startup, it is very difficult for me to hire a kid out of school. It's just like even if you're the absolute best at it, that logistics around it, the timing around it, it's just really hard. And so she had had a terrible time joining a startup. And I was like, I still wanted to learn how to be in startups and whatever. And VCs felt like a way that I could be very close to what I wanted to do. And so that's how I got started in VC. And there's not many VC friends that hire graduate of school. There's very few of them. And the ones that do are kind of focused on this model of like, hey, we want to hire a lot of young people to go through kind of like a apprenticeship program where it's your job to speak to a ridiculously large number of companies. And the basic hope here is, is like, by sheer virtue of volume, one, you'll learn something. Mm-hmm. And two, if you speak to 5,000 things, hopefully one of those companies is genuinely interesting and the fun wants to invest in it. And so that was kind of the model of the fun that I joined. And it was an awesome training ground to learn a lot about what works, what doesn't work. And through the lens of literally like thousands of founders that I was keeping on top of speaking to building relationship with. Wow. Yeah. It's such a great point because I think it does matter like who you have in your now. right? And so going to a school like Harvard or an MBA somewhere you are naturally surrounded by more people with bigger networks and pull. And I think, so if you're a founder, I was in the situation where I started a company that had nothing to do with all my my background. You know, my previous network was useless to me. So I was like, I need to figure out how to tap into a new network that can help me do this and I can find funding and take some effort, but it is important to build and find that network that you know, so whether it's like your local startup groups or communities like who in your local area is tapped into that network that you can go and start building relationships with. So even if you didn't go to a school like Harvard or have that built-in network through your family or you know whatever, it is important to kind of make an effort to find, you know, actually build your network not just the posting on website, something linked in. I think it's important to go out and actually build that network because it opens a lot of doors. Sometimes the most unexpected ones, you know. Yeah, and build up with founders. They're the ones who will, they will help you a lot more. I mean, it's just like most founders are scrappy. They're a lower ego. They have been through the pain and suffering and so they are very well-eaked to help. You'd be shocked. So. That's great. So okay, so you got the, you know, that you got the bug. You you decided to do this. Jumped in. Tell us a little bit about your experience, you know, the near-death pivots because I think that it's something ever, you know, it's so easy to highlight the successes and nobody, you know, people rarely talk about the stuff behind the scenes because it's just one. You're busy. And two, it's sometimes it's just so much it's hard to explain. But I do think, it's helped me over the years to hear those stories and hear that everybody has to go through those. For me, being aware of when to pivot is so important and that can make or break your success. If you try to hold on to one path for too long, it can burn you out, stall, run out of money, whatever. So tell us like a little bit about your experience there and kind of advice you have. Yeah, really is a story of a lot of pivots. I've maybe lost kind of how many. It's some of them small, some of them big. We're like three and a half year old start up at this point, but I would say we've we have been what we are today for only about a year and a half. And I would say that we only had true product market fit for like nine months. It's a journey for sure. So you have two years of really not having like a product market fit that made sense. Original business was essentially crushed by chat GBT. That's why I would describe it. So we were really focused on certain methods and traditional machine learning. It's like my educational background is in and we're building some software tools inside of it. And LMS basically just like put that world on its head. So three or four months into us starting our company, two P3 and then eventually chat GBT like completely flipped our world upside down. And so the company we wanted to build like overnight became relatively irrelevant. And so we then went to try to find product market more product market fit. And we tried a lot of things. We built things, gave them to people for free. We interviewed anyone who would ask us. It would talk to us about anything. At some point that was like more professionals or call that rage at some point, I literally just grabbed every friend I knew and I said, Hey, are you willing to spend 45 minutes with me telling me what your job is and how you do it. And what things make you the most frustrated about your job just so that I can maybe see if there's something they were doing that I could automate or support or augment. We did all sorts of things in a long period of time. And it was genuinely really difficult. And sorry, real quick, who was how big was your team at this point? You and co-founder or mean to co-founders, but at the time we we were building our first company. We had hired a founding engineer to join us. And that founding engineer had been with us through a lot of the pivots. Before we found product market for the left us. And I'm really happy for him in that departure. Like he needed to go build something for himself. And we were company with that product market fit. Like nothing, no ill will there. And so yeah, especially with the team, like it's it's hard. And at some point we built up a team a little bit because we thought we had product market fit and they realized that that wasn't going to work. And a lot of that team also left us again. And so that the team part is super painful. You know, with the co-founders, you look at each other and you're like, like, like, we're doing this to the ends of the earth, I guess. Like, like, but for people who've tagged along to that journey with you, it's a lot harder. And I actually think you should give them grace to leave. And I think that's something that took us a little bit of time to learn. But it's not that they're disloyal or don't believe in you or whatever. It's that look, the business doesn't have product market fit. There isn't a momentum for them either in their careers. And so the best thing to do is let them gracefully depart you know, don't don't fire them like give them a graceful path getting to a next opportunity that's positive for them. Um, yeah, we went through a lot of pivots. I would say that the two things that kept us alive through them is that one we picked it fast. We fitted very fast. So I kept this adage in my head and I wrote it on the board and that inside of our company that says like, we will feel when we have PMF. And it's one of those things that every founder gives us a piece of advice. And it's one of those things that you can internalize because you don't believe it. You don't feel it. And then it's one of the reasons I like we wrote it on a board inside of our office is like, if it was working someone, you know, obviously like you have to do some cycles, you have to make it better or you have to explore or like don't give them too early. But if it's working, you will find someone who is willing to rip it out of your hands in the worst version of it. Someone will rip it out of your hands and be like, you know, not everyone, but you'll find someone who will do that. And if you're working on something that some you haven't found someone after speaking to X number of people, is it willing to rip it out of your hands and it's worst version possible? There is very little chance that there is something quote unquote, bear that you're building towards. And so that was the standard barrier we kept ourselves to built shut down built shut down. And eventually we built the thing that honestly looking back at the first version of it was I'm shocked. Someone paid us for it. But someone did pay us for it. And they were like, they had a thousand feature requests. They're like, this thing is broken half the time. Like literally like it would down time, half the time because we had all sorts of scaling issues in the first days of building this thing. Like it was borderline impossible to use. But this person was like, look, when it does work, it's so good. I like it so much that I will pay you for it. And that was kind of the ahamma. And I was like, huh, this works funny enough. We we're building other AI products for PCs. And then in one VC meeting, someone asked for the thing that ended up becoming our product around sourcing and in deal and out of finding deals. We were like, you know, do that. But tell us more. And they were like, okay, if you could do X, Y and Z, I would love it. We're like, okay, we'll go build it for you. And then they loved it and ripped out the worst version of it. And then we were like, okay, how like is this scalable or is this just a thing that this one fund wants? And then we pitched it to dozens of others. And you know, all sorts of oppositions. They're like, uh, maybe whatever. But we met at least a handful of more people who were like, yeah, I ripped that away. Like I ripped that out of your hands. Give it to me, even if it's terrible. And we then hit the pedal from there. Wow. Amazing. Yeah. It's interesting like what goes through my head is, you know, comparing the ability to do that, you know, in a software type space versus, you know, consumer product goods. And in a lot of CPG companies that I talk to, the goal is to just like get as much distribution as you can and then show success versus proving it out like finding that one customer in a very narrow space who is like wants it and prove it out there because basically don't go so far down the path that you can't pivot. I think that's one of the benefits with tech and software, you can pivot faster. It is harder when you've invested a bunch in inventory. You're sitting on the inventory. You have to sell it through your marketing, all that, you know, same challenges. I mean, you guys are investing to build it and, you know, put time into it. So it's not, you know, a complete, you're investing there. But I think it is interesting that sometimes you just have to be willing to scrap what you did, call it a sunk cost and pivot. I think, you know, people try to hold on and almost convince, right? Not just convince investors, but convince their customers versus, like you said, people want to rip it out of your hands. I think that's such a great description for it. So worry. Yeah. Go ahead. So I'll just throw one thing on there. Even I think in the CPG context, what I'll throw out there is that maybe the bigger point here to make is like, you'll find people who like a thing and just liking a thing is not enough. It's maybe never enough. You need some group of people who are like crazy about the thing. Like they love it so much. They tell every single one of their friends about it. That's actually very important to like a classic NPS question is like, would you recommend this to a friend or colleague? The thing has to be good enough that without you asking them or prodding them or promoting them or giving them something, they independently of their own volition like the things that much they tell everyone else, you should also have this thing. Yeah. No, that is such a great point. And it's not an easy, not, you know, if they were that easy to find that thing, but it takes being open. And I think you mentioned earlier how many people you talk to and spent time with to really do the research, you know, again, yeah, lot, a lot of work goes into it, right? So where are you guys at now? What's the next big goal and what do you focus on? Yeah. We are in full team building mode is really all I do every day all day today. We are a team of 14 in New York City. We need to be a team of 40 by the end of the year. And so there is not a role or function that we aren't hiring for. We have a philosophy at Rayleigh that says if we meet someone who's extraordinary, we don't even know what role to put them in. We're just going to hire them and figure that out after the fact. So that's all I do is just try to meet people and fill our team. So that's all I do every day all day at this point. How fun. That's great. And are you guys so you're growing your, your focus on kind of this space in particular? Yeah. We're building a ton of new features, ton of new data that we're going after, ton of more autonomous capabilities. So trying to make it even lower and lower lift so that investors are continually being notified and suggested with fewer inputs from them, they're getting closer to the thing. is that might interest them. So a really long roadmap to build. And then otherwise, it's a lot of good market. A lot of what we do is to work with investors to really shape and mold to them. It is where our other efforts are just mostly about getting our customers to be as happy as possible. Yeah, very cool. Love it. Anything else you want to share or advice or and where can people, if anyone extraordinary is listening and decided, I want to hop on that train rather than pushing, pushing my own big rock uphill, where can they find you and reach out? Yeah, of course, we're at RayLew.ai's our website at the bottom of it. You can see our careers page and there's lots of open roles. But also if you don't see an open role, just paying us. Also speaking of CPG founders, our head of product and customer success is a X CPG founder. She tried to start a business. It didn't work, which happens all the time. And she is one of the most successful people at RayLew and we love hiring X founders. So that's you. We'd love to work with you. That's very cool. Yeah, I think it's amazing. You don't realize how much you learn in the process of starting a company. And I just, it really is so true that it's never a failure. It's just, you know, again, it might be a personal pivot, but you learn so much going through that process. It's just crazy. So amazing. Well, thank you for joining us. Congrats on all the success. We will post the link to RayLew and promote that and the link to the careers page down at the bottom in the show notes and best of luck. So excited for you. What a fun ride. Thank you for taking the time, you know, this is a really fun conversation. Okay, we'll talk to you soon. Thanks for listening to Seed Money and especially thank you for sharing the show with other people. Every time you share the show, you're helping someone turn their idea into reality. If you've enjoyed listening, the best thank you is to rate and review the show on your favorite podcast app. It not only helps give me feedback for what kind of information you need, but it helps the show reach more people just like you so they can start their business, raise capital and get the funding they need. And stay tuned for the next episode of Seed Money.

Podcast Summary

Key Points:

  1. Investors are more likely to back companies that resemble their past successful investments, so founders should research portfolios and tailor pitches accordingly.
  2. Founders should avoid mistaking investors' curiosity for genuine interest; it's important to quickly determine if an investor is seriously considering an investment.
  3. Rayleigh, an AI platform, helps investors find companies based on custom theses rather than generic signals, improving match quality and reducing competition for the same deals.
  4. The platform uses public web data to discover companies early, even before they raise capital, as long as they explain what they do online.
  5. Investment trends show a bifurcation

Summary:

The discussion emphasizes the importance of finding the right investor fit early in the fundraising process. The guest, Ali Dijardi, co-founder of Rayleigh, advises founders to research investors' portfolios and tailor their pitches to align with past successful investments, as this increases chances of interest. He warns against confusing investors' curiosity with genuine commitment, noting that investors often enjoy learning but may not invest.

Rayleigh addresses the inefficiency of traditional sourcing by allowing investors to define custom theses in their own language, using AI to discover niche companies that match. This approach helps investors differentiate themselves and find less competitive deals. For founders, being discoverable requires only a public description of their business online.

Current investment trends show a split between AI-focused moonshots and capital-efficient vertical software, with less funding for other large-scale ventures. The platform serves VC, growth equity, and private equity firms, helping them find companies that align with their unique criteria.

FAQs

Research the investor's portfolio to see if their past winners match your business model, go-to-market strategy, or other key traits. Tailor your pitch to align with their specific success stories.

Founders often use a generic pitch for all investors instead of customizing it. Each investor has unique preferences, so your story should highlight the aspects that resonate with their past wins.

Investors may seem engaged out of curiosity, but it's cheap for them to ask questions. Quickly assess if they have a material interest by focusing on those with a clear track record in your space.

Rayloo is an AI platform that lets investors describe their investment thesis in their own words. It then builds AI agents to find and monitor companies matching that niche criteria, unlike traditional data tools.

You just need to explain what you do somewhere on the web, like a public website or Crunchbase profile. Even a stealth page stating your focus is enough for Rayloo to find you.

Rayloo creates custom data columns per fund, like defining a 'great founder' based on their unique preferences, such as industry experience or years of work, rather than using static labels.

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