Startup Success doesn't teach you much

title: Startup Success doesn't teach you much
author: Founders Podcast
publication: Founders Podcast
published: 2025-12-09T09:36:00
source_url: https://anchor.fm/s/10542bd40/podcast/play/111359052/https%3A%2F%2Fd3ctxlq1ktw2nl.cloudfront.net%2Fstaging%2F2025-10-18%2F412709590-44100-2-2be764d58c109.mp3

word_count: 10186

Hello, Andrew. Welcome to the founders podcast show. Thanks for having me. How are you doing today? Good. No complaints yet. It's morning in New York. Great step. Great step. Andrew, we've been talking just about a joke you share with founders around the journey to take the right direction. Would you be able to share it with their audience? Yeah, I tell them a lot of jokes. Probably the one that I can actually share with the audience, because I'm not going to start a podcast with like F-bombs is the one I tell about. There's an old older guy in the middle of the street kind of looking straight down in the middle of the night. And his friend comes over to him and says, you know, what's going on? What are you doing in the middle of the street? You know, he says, well, I lost 20 bucks. He says, I'll help you look for it. So they're looking and like, you know, about a minute later, like it's in the middle of the street. There's not a lot of places for money to be hiding. So his friend says, I don't see it. Where exactly did you lose the money? And he goes down that alley. So well, if you lost the money down the alley, why are we looking for it in the middle of the street? It was right in all the lights better. So thank you for the courtesy lap. So most of the startups that I work with, I'm an accelerator, I get a laugh whether it's funny or not. But the critical thing here, I'm just going to just find my lighting. I've got to do that. The critical thing here is what I'm trying to get to them is we'll have our comfort zones. So maybe you are a technical founder. So your gut, like the happy place for you, the well lit place for you is the middle of the street. But what you may need to do more than anything else at this point in your company's juncture is understand your go-to-market, test different marketing strategies. And that's the scary dark alley view because that's not what you're comfortable with. So that's how I kind of get across in a non-threatening way that a founder like you're doing what you're happy and comfortable with. You're not doing what you need to do right now to take your company to the next step. Very interesting. And thanks for sharing the joke. And I think people who are going through their founder's journey, they would definitely understand it because we all made this mistake at some point of our life. So yeah, that's quite relevant. So Andrew, you have lived almost all the sides of the startup table. You've been founder, you've been investor, you've been an accelerator director, teacher, you know, whatnot. You have also created I think two companies already from the ground up, right? Yeah. So let's start from there. Would you be able to share your story around how did you came up with an idea to start your first company? What was the struggle starting it? How did you make it successful? And what was this exit looks like? Yeah, sure. I'm happy to do that. So a lot of things in life are luck. A lot of things in life are intention. And a lot of things are, you know, intentions that you're ready for luck. You can actually take advantage of it when it happens. So, you know, I was in business school back in the dawn of time. It was a kind of pre-internet sort of I remember seeing my first like, wow, net scape. That's kind of cool. If there's ever anything here other than government data sets, this will be huge. So when I came out of business school, they're becoming a startup founder. No one knew what that was. There was one guy in my class that was in VC and no one knew what Ben did. Ronically, I ski with Ben. So now, I'm like, oh, I know exactly what you do. I do it too. But at that point when I went out, I was in a consulting world because that seemed like the interesting thing to do at the time. And I had a friend who I went to business school whose brother was starting this company called Bunk 1. So Bunk 1 is what we would call SaaS for summer camps. Pass were protected photo galleries for kids, messaging systems where, you know, he was a parent could send the message and receive a message, but the kids would be nowhere near like electronics. Like this was hard stuff back in 2000. So I ended up joining the team. I was a third founder, third founder of that team. Getting to them was luck. Like, I knew I wanted to do something startuply by that point. It didn't know how. So I was fortunate in that I had networks and I just kept talking to people and I got on to it. So we did that for eight years. We went through, we were paying attention. I joined in 2000. So we went through the 2001 crash. That was no fun, but without salary for a long time. Ultimately, we did well. And by mid 2006 or so, we were thinking about maybe selling the company before at a banker. He got exactly what I thought was a good deal for it. The main founder of the CEO wanted more. So I said, you know, Ari, I'm happy with this deal. If you want more, you should be thrilled to buy me out at this price. So we negotiated an exit by 2008. You know, when I was out, get my last buyout check. If you remember what happened in 2007 and 2008, you'll understand where, you know, Ari's like, I think I should have taken the deal. But just happy ending for them, the company sold in 2016. So, you know, everyone else got out too. That's nice. That's night. Would you be able to share number of users? How big you went from zero to, you know, big number? Yeah, I can tell you, we went from like zero camps because everyone starts with zero to a couple thousand camps within five or six years. That's not bad. And did you engage with any kind of growth hacking technique strategies? Or was it pure because of the pain in the space? Yeah. So it's interesting. We had a B2B2C model, right? Which is a very strong model if you can pull it off. So what it meant in our case was, you know, we go, we would sell to the camps. So we go to camp conferences. We make outbound sales, phone calls. That's some really interesting people that way. And but in many cases, the camp wouldn't pay for it themselves. They could, but often they would pay part of it. And then they would have the parents pay for other parts or the day for all of it. And when it came to photo sales, it was all driven by the parents buying the photos that the camps had taken. So we would sign up a camp. And in some cases, that would be zero money upfront. And then we could market to their user base, their parent community. So B2B to lock them in and B2C after that to actually convert it to revenue. It's a really strong model if you can make it work. I see that with a lot of my portfolio companies in the real estate property management space, though sign up a building, but then they have to sell to residents. So it's a cool model. But I'll be honest, back in early 2000, like no one even knew what the phrase on rotation wasn't. What's on that? Yeah. No. There were a couple of blogs out there, like Fred Wilson had one of the early blogs, super sharp guy, very nice guy. But it just wasn't that many. There wasn't like this overwhelming amount of people for better or for worse riding about what they matters. So there was a lot of like experiment. There was a lot of like AB testing on email deliverability. There was a lot of AB testing on web pages. There was a lot of just sitting around the room and saying like, Hey, you know, when I'm at a conference and I say we do XYZ, they just keep walking. How do you get them to stop? I'm very interesting. And that's why I love the conversations with, you know, matured entrepreneurs like yourself, because you've gone through all the struggles you have navigated through these trenches. And then you came out of it learning all these things. And one of the quotes which always stays with me that success doesn't teach you much because success is mostly mostly about enjoying it. It's all the failures in your life which teaches you everything, right? That makes you powerful. You know, the world is exactly same. It's just you becomes more stronger to manage that, right? So the phrase that I heard ash was like experience is what you get when you didn't get what you wanted. There you go. There you go. You always get something. Yeah. Yeah. Great. So and let's move on to the second company then which you started. What happened there? Why did you? So obviously you got an exit and then, you know, we all know what happened in 2008. But when you were, uh, were you doing something at that point of time? How did you came across this opportunity? And what was going on in your mind when you thought, okay, let me start this one now. Sure. Sure. Sure. Bear in mind what I just said about experience. The second startup was a hell of an experience. So let me kind of paint the picture 2008. You know, I'm gone. Sorry, end of 2008. I get out and starting in 2009, I'm working at a family office. Right. So I'm bringing deals to this high net worth individual. I'm managing his private equity funds, his hedge funds, all of whom are like, you know, tanking because of the the world meltdown. And, uh, you know, along the way, I'm starting to bring in deals like secondary. I can buy a big chunk of Facebook. This was back when it was equivalent of a buck 35 a share. Or I'm trying to pitch a new startups for him. Not the best time to do it. But if you're liquid, when everyone else is not, you can get some great deals. Now, unfortunately, the guy I worked with was very, very difficult. All right. And not like, oh, he's difficult, but you learn a lot. Just like difficult, like, oh, my god, I'm gonna bang my head against the wall every night when I come home. So I was looking to get out. So I put the word out there that I'm looking at. I might want to do another startup. I had some of my own ideas. And I was approached by someone on my network who kind of like a consultant for startups. Uh, so going back to what I said before, makes a purposeful and luck. Like, I was being purposeful about getting my name out there. I had started to build my network a bit more, which was a mistake I did during my first startup. I had built it enough. But I was doing stuff during that time at the family office, like writing for Ali watch and other things that got my name out there. And ultimately, I was recruited to help a, quote, the idea founder actually put flesh and blood and bones to his, uh, who his idea in a digital memories type start after called layer kick. So the idea is like, you know, as parents, we have tons and tons of photos, tons and tons of notes of some sorts, even voice notes if we wanted to. All of these things just exist. And there's a big bucket in the internet or several big buckets of the internet. And effectively, since they're not organized, they're not tagged. Like you really have none of them. It's not like the old days where, you know, you had your album, your album had 50 photos in it. Those were all the photos you had. So you looked at them. Now we have 15,000 photos. We never look at them. So the idea was to solve that problem. Uh, and he had this big, uh, bold vision, you know, for like, down the road with all the features. So I needed to boil it down to an MVP, which by that point, I was really good at. I needed to recruit a CTO, which at that point, I had the connections for I need to pre-sell it to VCs, which at that point, I'd gotten a little better at doing, uh, and it all done. Uh, and then he got impatient. Right. I knew it was going to take six months to come out to market the three months. He's like, I can take it from here. And I said, uh, respectfully know you can't and equally respectfully, that wasn't our deal. Uh, and at that point, it devolved into lawsuits and crying and hurt feelings. Now I totally understand that, um, would you be, I know you might not be because of all the legal, you know, aspects of it. Were there any learnings from that kind of, um, interaction experience? Sure. Um, which you could share with our audience so that, you know, they can learn from your experience. Yeah. So headline is, uh, and I've heard this not my phrase earlier. It was when I was contracts keep honest people honest. The main reason to write something down is to make sure that you're actually talking about the same thing. You might think you're talking about the same thing when it's all verbal, but you actually put it on paper. Oh, then you're as, oh, we never dealt with this scenario. We never dealt with that scenario. And you fleshed them out and like, great, now we agree on something. And if there's a disagreement down the road, because it was a gray area in the contract, you know, it's a good faith. It wasn't like I thought X she thought why it was like, oh, neither of us thought about it. So that's great. If the fundamental is that you both trust worthy people, right? Now, once you get into a situation where someone's going to say, I know the contract said X, but guess what, sue me, uh, it's not going to be worth your while, the sue over this, just roll over and take it. Then, you know, the contract doesn't help you. Right? I've learned that actually a little bit before I had like a small claims case against like a mover who damaged my couch. I won. I'm like, great, collect. I had to go attach out, and I had to go find out who owned their van to like collect against them. Once you're in that space, especially if you're a founder, you're often in the situation where life's just too short, right? I mean, your startup's going to be dead because you're wasting too much time in lawsuits. Even if you're still in, ultimately, he ended up killing the startup for other reasons. But it's just the numbers are usually too small to deal with it. I happen to be kind of nasty if I think someone's taking advantage of me for lack of a better word. So I happen to get a really, really, really good employment lawyer who also thought this was a slam dunk. She'd send the letter on her letter. It would be done in two weeks. The other party dragged his heels. Then she got mad and you don't want to see an HR lawyer get mad. It's actually like scary, awesome to watch. That's an interesting part because you know, dealing with people, dealing with all these technicalities, we always think that it's easy because if you're an employer or a founder or a startup, you know, entrepreneur, you think that you have some kind of leverage, but you don't. You're actually in a losing side of the game when it comes to all the legalities and the rights we have in the system, isn't it? Yeah. So I don't know if you're from the game theory. I don't want to like, you know, put everyone to sleep, but just think of it as at every point, there's like, I can do X and the outcomes could be A or B. I do X or Y outcomes A or B, but where it gets interesting is something we talk about sub games. So it's like, we don't negotiate with hostage with hostage takers. And then they take hostages. Can you really hold to that and not negotiate or it's the pressure from your constituents can be so strong that you have to? So like you could say I'm going to do X, but then when push comes to shove later in the game, you do Y. So to take that out of the abstract, you know, I think a little bit more about what happens down the road. Like the contract says these are my rights. Okay, if they don't do it, then what happens? Right. Where do you have leverage in it? And if you're a startup doing a deal, let's say a very large corporate who's going to be your partner, it's just have to go into it, realizing you don't have any of that leverage. Right. There's very little you can do later on. Now you can flip that a little bit like once they're so addicted to your startup that you will pry their cold dead hands off it. Then you have leverage. So don't be an asshole about it pardon my language. But then you have a certain amount of leverage because like we're not going back to the old way. So it pays to think through the game at all the stages, just to say, I know what the contract says, but where's the real power lie? So that's kind of take away number one from that big point takeaway number two, or maybe I should flip the water. It's just spend more your time getting to know the people that you're going to work with. Before you even go down that path, before you even worry about who has power when, just try not to get in bed with anyone that you're not really comfortable is like a good person. Right. Trust were the professional individual, diligence them through your network, who's worked with them before. If it's a VC, how did they treat the portfolio companies that didn't succeed? Right. What happens when push comes to shove? You know, what do they like and try to get as good a feel for that as possible before you even bother trying to paper over things with contracts? Yeah. No, definitely. Great. Well, thank you so much Andrew for sharing both the experience. I think that these are very good for our listeners to understand like what kind of challenges you might be facing going forward in the similar journey. Right. So let's let's move to the next milestone of your life, which is why did you thought or why did you decide it to go forward and write this entrepreneurs Odyssey book? Was it because you've won through the experiences which you thought not everyone in the same space is experiencing it and then you wanted to share that? Or is it more around reaching to the point in your life where you have, okay, I do have everything sorted in my life, my sustainability, my lifestyle, dependencies on me, something is missing and that is the happiness I get by helping other. What was this exactly? Yeah. I mean, I certainly don't have everything sorted yet. I feel like, I'll give you an example from my friend. He lost his mother. I think she's 93 and she had tons of projects going on. Like she was renovating a bathroom and she was studying some other hobbies and he's like, it's a total mess for me to try to clean any of that up. But I was good with that because if somebody passes and there's not a lot of stuff going on, that kind of means he's just waiting to die. Right. If you have a lot of stuff going on, you're still living life richly into its fullness. So I saw a lot going on. I still don't know what I want to be when I grow up and that's totally okay because I've enjoyed a lot of things along the way and I'm going to enjoy a lot more. So to take it back to kind of put you in the mindset I was in when I was thinking about the book. You know, I had done the two startups with the family office in between. I was on the verge of doing the third startup and then I got pulled in with Dream It, which at the time was one of the top five accelerators slash VC funds in the world. The third one ever right after white combinator and tech stars, the archetypical sit your butt in a chair for three months and we'll bring you speaker's beats of beer demo day model was basically invented by tech stars and Dream It. And I came in to run the New York office and then I made this kind of interesting change. So I went from being a founder who thought about one company at a time to an angel investor who I got, you know, maybe if I got one or two or three really interesting deals a month, I thought about him and I pulled the trigger on five like kind of interesting. I'm seeing it from the other perspective but still a handful of companies to suddenly having to look at over a thousand startups within a two month period to pick 10 that I wanted to work with and then I had those 10 I'm working with the three months where you do the math. I'm meeting with each one for minimum an hour and then I got all the follow up work and I'm trying to introduce some customers. It was a step level quantum level up in of my game there. So I started learning other things. I started learning how to do that effectively and one of the things I learned is that giving advice in the context of a story or a joke was just far more effective. I could tell them, listen, you need to test your cost to customer acquisition. Your company lives and dies on it. I looked at your model. Here's what happens if, you know, if we change the conversion from premium to pre to premium just by a little bit like your company dies. I could tell you that or I could tell them the story of this company that was a block discovery platform. They had this model. Everything was ready to go. They, well, everything but the premium features and they're like, oh, we're going to go just build. And then in, you know, two months, we'll have it. We'll roll it out. And I'm like, dude, you're going to get the demo day. And if you don't have those, if you don't have those metrics in place, what are you going to show them? Like, oh, that's a good point. What do we do? So I said, instead what you do, and actually, I'm going to, there's two stories. I'm going to tell the other story that happened before me. This is my partner, Mark. He's saying this. Mark tells this, this blog discovery platform. Like if you, if you want to, you can test that right now. Right. You go up there. You put the, you know, hey, here's what the premium is. Here's how much it costs by now. And when people click the buy now button, you can say, I don't have a merchant account. It doesn't matter. I say, hey, Ash, guess what? Two months free on us. But it doesn't matter that you're not taking the money because to the customer, it looked exactly like they would purchase it. So now you know exactly what your conversion from free to premium is. And you can go back and plug that into the model. And see if the model works. And like, oh, what happened? Right. Because now the story they want to know how the story ended. So I said, they came back a week later and they said, we're screwed. Right. We're like, attentive where we need to be on conversion. But we have an idea. Instead of being a blog discovery platform, can we help people find the best seats in sporting events or concerts? Because that's where a lot of the blogs they were directing people were too. And if you're here, we got a lot of people there. What's new? That. So that company ultimately became Seakeek. And if they had gone and done it the way they thought they were going to do, build, see what happens. Rather than stop, don't build, test. Seakeek never would have been. Now I tell them, I tell these other startups that story. And it's just like, oh my god, we got to test this yesterday. So I told that to another company in the, there were tools for startups to like tell their stories and big decks better. They did tell, they didn't have a merchant account. They said, it doesn't matter. We're going to test it. The same we Seakeek did. They hit their number and they were able to keep going. But I learned that like you embed those ideas in the stories. It just makes it's more powerful, which I had a way when you think about it. Every religion known to man starts with stories. They don't start with, hey, here are the 10 things you can't do. Right. worry out. They don't start like a constitution with here or your rights. They start with a genocidal story. So it's just a more effective way to do it. So sorry, this turned into a long answer. I had that as the experience I was picking up when I'm running the accelerator. And then things started to click. Because I remember back when I was in business school, I read a book called The Goal. And the goal for those you're not familiar with, it was very popular in business schools in the 80s and 90s and a little less so today. But it was a novel written about a guy who was sent to turn around the printing plant that was failing somewhere in the Midwest. Totally over as I didn't know what to do. He meets this mentors consultant on an airplane, who like kind of mentors him through the process. And completely unrealistically, he doesn't try to charge him, but that's a different point. So I'm like, I got it. Right. That book, the book that I remember from business school because it was written like a novel, but it was actually a textbook for strategy and operations. So I, that was memorable. The stories I'm telling to help startups like understand where they need to focus. Those are effective, more effective than just how to guide or blend advice. If I ever write kind of the accumulated wisdom I have on what it takes to build a startup, I'm going to write that as a novel. I'm going to write the goal for the startup journey. So that's where it all came together. That's why I decided to write it this way. Plus, you know, between you and me, Ash, like a lot of business books are just deathly boring. They're just really hard to read. They're the same kind of dorky, earnest, ghost written, anecdote, anecdote, anecdote, name drop, name drop, name drop, one page chapter summary. It makes my eyes glaze over. So I can only imagine what it does to people who, you know, everyone else out there was reading five or six of them just to clean, insights from them. So I wasn't going to write that. Yeah, no, I totally agree with you because I read tons of books every year and I think I can literally name a few of them on my fingers, for example. I think Profit First was one of the books which I read, which I really like. The Nudge, the tools of Titans, you know, and I'm thinking to read, pitch everything later this year. So these are the few books which I thought was really, really helpful to run my business and learn from them. Otherwise, you're absolutely spot on on like anecdote. It's a format basically for every writer nowadays because they know that this, this kind of work. Well, I'll take a great step further. Even the good ones. Like I read a book called Who, which was very, it was about, you know, how you actually recruit top players. And it's actually great content, but it was hard to read. It was hard to read. Even the good ones are hard to read. Yeah, because we have to make the reader's life easier by making it easy to read instead of making it harder for them to read and understand and then potentially learn from it, right? Yeah. Great. So let's move on to the next part of our interview then. And a lot of people nowadays want to get into startup or founder space. The reason behind it is not just 2008, but there is a consistent crunch of feeling in the market right now. So for example, a couple of years back, we heard these news around Amazon fired for 15,000 people that affected the whole market in UK. Last year, Microsoft fired 11,000. And more and more, these things are happening. People get into their habits of being comfortable. They live in million-dollar houses, they drive Tesla's or rangerors. They don't really necessarily need that. It's just because they work for these big giant companies. They can, you know, acquire the capital through the salary or other other form, former self-payment. They get habitual of it. But the sudden hit makes them think that this is not necessarily my journey is. I wanted something different in my life. People want to get into the startup space, but they're not clear how. Or I shouldn't, I shouldn't say, let's talk about why and then let's talk about how awesome. You actually raised like five or six interesting topics. So let's start with the which may be a little late for a lot of your audience who are already doing it. But let's start with the, like, should I do this at all? So let me give you kind of a persona. I'm sure a lot of your audience will identify with this because this is where they started, right? They're working for a large company. Maybe they're in an office. Maybe they're in a cube. They're dealing with one relatively important, a very important part of what they do. And it's just horribly painful. All right. So they have some variation of this. Gotta be a better way. Light bulb goes off. Oh, I think I have a better way. So then what do they do? So you got to decide, right? Do you have the temperament and the hunger and the desire to leave the comfortable environment you're in and go start a startup? And I'm going to say something that's a little bit maybe controversial here because we're also gong a hoe about, like, it's great. Do it. Leave your dreams, right? I'm going to say it's not for everybody. There's a lot of stress there, especially if you're in the stage of life you're talking about, I got a mortgage, right? I got two kids in private school, right? My wife is also on commissions like she's a real estate agent, right? Doesn't have health insurance through her, you know, through her company. That's more of a US issue. I know. Maybe it's not right for you. Maybe you're just not comfortable with that level of risk at that point in your life and you shouldn't do it. Or maybe you're worried about all that, but you just don't know what the day-to-day is. Like you've seen the Facebook movie. I was like, oh, dramatic. We've read the Steve job, like biopic. So that's really cool. That's not what the real, that's not what the real startup journey is like. Now, startup journey is a lot of staring at a computer. It's a lot of people telling you no. So the other benefit of writing, you know, my book as a novel was that you actually get the feel for what it's like. You're a gut. You can kind of say, you know, I don't know if I can see myself doing that. Or, oh, yeah, I can do that. So to ask the first of your points, yeah, it's not for everybody, but there needs to be, and I think I've written a way for people to decide, like, is this for me or not? So that was point number one. Point number two, which is kind of a bigger issue, which is kind of the the the ebbs and flows of the startup market. It gets really hot. People are excited. Everyone wants to come in. Then all of a sudden there's a crash or a reversal. And then all of a sudden, I was like, everyone's scared and they leave, right? It's kind of the waves. They come in. The tides come in. The tides come out. A lot of people get caught up in the excitement. They come in where everything's great. And then like they leave because like, oh, that's nuts. I can't do this, right? You know, I'm not getting funding in the three months. People like told me it would take. So I'm out. So there's a lot of that, you know, you just got to understand about, you know, understand what it's really like and understanding if you have what it takes to stick to it is what matters. But there's an interesting side effect, right? So let's let's do a little thought experiment. Let's say you were an alien and you know, you're looking down on the earth in 1960. And instead of like, you know, I don't know, ripping up cattle or making circles in the crops fields, you're like, they're on the verge of a really interesting startup revolution venture capital is going to explode. startups are going to explode. Their whole world's going to change. Where do I think it's going to happen? What's the epicenter going to be? So you as that alien might think, well, I want a place that has good concentration capital, right? So you might need to make it work, but really well educated workforce. Maybe they got a lot of universities nearby. And then maybe the headquarters of a lot of the big companies that can be customers. So you'd look around the globe and maybe New York would be your first choice. Arguably London also, but let's take the US, right? You'd say New York, would you pick like this, like unincorporated, not even close suburb of San Francisco? Never in a million years. Like, okay, you got some schools out there, but it's all spread out and like there's no customers in Palo Alto. And you know, when you compare like the capital and the customers between San Francisco and New York, no, you put your money on New York. Maybe I'm Boston, right? I didn't play out that way. And there's a, you know, I don't really have a lot of great theories. One of my theories is like the first wave of innovation required hardware, which means you need a garage to work in and we don't have garages in the city. So maybe that was it. Why it was just a matter of at that very beginning, where everything is like a green field, little things snowball. Because I got lucky with one startup, they made some money, then all those founders went out and started their new startups. And it's just kind of a little bit luck of the draw where that, you know, the snowball world this way instead of that way. So San Francisco and the Bay Area became like the leading in that leader in that space, but then 2008 hadn't, right? So there's something really interesting in New York. Before 2008, if you were a super shark person, quantitative or very entrepreneurial, you'd probably go into finance, hedge fund. I'm going to start a quant fund. I'm going to make a ton of bucks. And it's a lot less risky than the start of things that people are talking about. So the best and the brightest and the most talented and the most risk tolerant went into these financial services. And then the big crash comes with Lehman. And all of a sudden like, oh, my job's not that secure after all. And at the same time, like everyone's making like bokeh bucks with a lot of the consumer facing startups in the Bay Area. So like not as safe as I thought. And oh, this could actually be a lot bigger than I thought. So a lot of talent migrated from kind of the financial services sector into the startup world during that crash. A big change in mindset. And it wasn't soon thereafter. It wasn't long that they're after that New York overtook Boston as a number two startup ecosystem. And now depending on the type of startup you're doing, the answer might be no, you stay in New York, right? And maybe get some money from people in San Francisco. Or maybe they already have an office in New York because they have to be in both places. But that's kind of the second point you were making about like these crashes sometimes do interesting things to the ecosystem and to people's perception of what's riskier and what's a better opportunity. Indeed. Indeed. Definitely. Let's also talk a little bit more about the strategies you have mentioned in your book. Because Andrew, I think it's a great idea to read above which is easy to read and understand it from perspective of somebody who has lived it in, you know, practical world. But also understand what kind of value people will get if they go through this. One thing which I loved about Mike's profit first is now I have a set idea in my brain that if I go and start a new business, this is how I have to structure my banking or my sales and marketing and everything in my business. Is there is there something similar or in contrast? Is there something which this which your book actually gives as a value to the readers which you think could stick with their mind for the life? Yeah. So conceptually, I like founders to think about their startup like a chain rather than as a rope. So let's kind of unpack that a little bit like a rope has a lot of strands to it. And you've I'm sure seeing like ropes that like a couple of strands are afraid and broken, but the rope still holding. Sometimes it's holding on by a thread, right? That's a common saying, but a rope will still hold even if some individual strands are not, you know, sound. That's not a startup. A startup's more of a chain. If any one link in the chain is broken, the startup's not going to work. So you might have the best go to market out there, but if your market size is too small, it's not going to happen. Right? Or if your solution isn't the quantum level better, then the alternative is just a minor improvement. It doesn't matter if everything else is great. So as a VC, especially when I started looking at those thousand startups as applicants to accelerate a program, I got very good at I guess or you know focused on just scanning the chain. Where are the weak links? I don't need to dig into the market size right now. I think it's big enough. I'll deal that later, but I don't think the go-to-market is going to work. I don't think their cat is low enough relative to LTV. I need to focus my effort there. So if you're a startup, you have to think about the chain kind of ballistically, right? What parts of my business and then of course the pitch deck that represents my business are potentially weak links or might be perceived as weak links in the investor's eyes. And how do I address that? So that's kind of the overarching mentality of if you're going to be into a startup, that's how you got to think about it. Very interesting. Great. And was was there anything you thought or you experienced with somebody whom we were helping as a mentor, as a guide, as a coach, which you might thought would be helpful for our listeners in the case of a new founder, like a full-time founder. Sure. Sure. So I wish I could remember where I learned this. It's called an index card prototype of your site. I wish I could remember where I learned it, so I can get credit for it. It is a chapter in the book under customer discovery. So let me kind of explain on the little background. So the startup in the book is called Call Jaur. It's actually loosely based on a startup that I'm working on on the side. It's a speech to text startup. As a funny aside, I actually wrote about 80% of the book, speech to text directly to Google Doc. So it's a book about a fictional speech to text startup based on a real speech to text startup that I wrote 80% of using speech to text. That's a little meta. But so the founder has this idea of what he wants it to do. He's talking to the his mentor and his mentor is talking to who's your ideal customer profile. He thinks it's going to be like a B2B company. They talk up through it. It's like, no, it's wrong because of X, Y, and Z, right? They go through like visualizing what that persona would do. And he changes his focus many pivot to the kind of on the go professional who is juggling their phone and trying to take notes at the same time while they're running to a different job site like a real estate agent or general contractor. So once he's got that and he's kind of rethinking what the app looks like, he goes to a process where he's actually written out sketched out what each screen of the app looks like. And not even photorealistic. Just like a pencil sketch like using Balsamic or one of those tools out there. And the process he goes through is he finds a bunch of people, 20 plus people, but in the story of this one chapter, real estate agent, super busy. And he says to this woman, he says, listen, he's what I'm going to do. I'm going to put these index cards in front of you. Each index card is a screen. I'm going to put one in front of you. And I want you to interact with that card as if it's your phone. So if there's a button, touch it. I can't read your mind. So I just want you to verbalize what you're thinking. I won't answer your questions because I'm not going to be there when you have this app. But I want you to talk like, I'm not sure what this button does or oh, yeah, I need to do X first. Say that out loud. So I understand what's going through your your your mind when you're doing stuff. Depending on what you press, I'll give you a different index cards. I'll be a different screen that you get to. So for the cost of a pack of index cards, he was able to run through the user interface with a customer, understand what parts were confusing, what parts were not, what features people actually cared about and which ones nobody cared about. So we didn't have to build those. And then also understand where the hesitations might be. Like, oh, I'm not sure about what happens at this point. I'm afraid to go on or I don't I need to understand what you're going to do privacy wise with this information before I trust you. So he's able to get all that information without coding a single lie. And you can do it fast. That's one of the one of the learnings that, you know, I wish I learned before my first startup. We did it exactly backwards and wasted a ton of money. I wish I could remember who to thank for that because it's an awesome idea. But if you read the book, you can thank me for it because it's like chapter seven or something. Great stuff. Cool. Well, Andrew, thank you very much for sharing all these wisdom with our listeners. We have another part in our episode, which is called the Lightning Round. We got six quick fire questions for you prepared at any stage. If you feel like you don't want to answer any of them, just give me a skip and then we move to the next one. How does that sound? Sure. One hour sounds like fun. Great. Okay. Question number one, what are the top three strategies to find out if you want to do a particular startup or not as a founder in 2025? Got best thing to do is work with the startup. Maybe not as a startup, but a prior startup where you're close to the founders. You'll see what it's like. You'll see firsthand what the stresses are. We'll see firsthand what actually happens day to day. Not what you think it is, but what the actual flow of work is. Full stop. Best way to do it. Second thing you should have, especially if it's a B2B startup is domain expertise. It's very hard to sell, say, to real estate developers. If you haven't been working in the industry for five years, 10 years, know the lingo. So if you're thinking about doing it and you don't have that expertise, maybe you take a two or three year prelude and start working on that. And the third thing, why my book? Let me roll that back a little bit. The third thing you do is a tons of resources out there. There's a lot of resources out there. So go out and learn from other people's mistakes. Now, the tricky part is the quality of a lot of those that advice varies. Some people are great. Some people don't know what they're talking about. And if you do find it, it's usually fragmented between like a blog post here and a blog post there. So you're trying to stitch together. Kind of cohesive. Like this is all I need to know, which is kind of why I wrote the book, so you don't have to do that. Indeed, indeed. And then my next question was around the book. The question is, what book would you recommend to our audience and why? So it depends on, obviously, as a VC, the phrase we use most often is it depends. But if you are a founder who's been working on a startup for a while and is ready to go and to raise money, but doesn't really understand or doesn't know enough about how VCs operate and what they're looking for. And kind of what's happening on that other side of the table so you can relate and be effective. There's a book I read over 10 years ago called Mastering the VC Game by Jeff Buskang. Well written, it covers like things like, oh, you know, we raise, we have a three year investment period. After three years, we're probably not making initial investments, so feel free to ask like how long has it been since you've raised? How much drive powder you have? It was, you know, at that point in my career, it was a real eye opener for like what that other person I was talking to, who I had just think, you know, they're a pile of cash, right? But, you know, what actually motivates them, what the constraints there and how they're rewarded. So it's a really great book, if you're at that stage in your startup. Awesome. Great. So thank you for that. I might add that into my Kindle. I have a like a kind of like a playlist on Spotify, where I keep adding the books to read through one by one. So thanks for that. Sure. Let's write it off to the entrepreneur's Odyssey. That's, you know, it could be the next book in your playlist. There you go. Okay. So what's an attributor or correct to just stick in your mind of a successful founder? Again, I heard this from somebody and I can't remember who told me so I apologize for not citing my sources, but I like a founder who was well-reasoned, but loosely held theories, beliefs. So for example, I ask a startup, okay, you're going to target, you know, the real estate developers who are doing projects between one and five million dollars. Why that instead of the bigger guys? Well, you know, these guys generally don't have any software solving the problem I'm talking about. The bigger guys have something, maybe it's homegrown, maybe it's like a partial solution, but it's harder to get them to switch than it is to get these new guys who are green field opportunities to, you know, adopt tech. Like, okay, that's a well-reasons opinion. And now let's say I come back to them and I say, actually, I work with a lot of really large developers, and I got to tell you like the solutions you think they use, 99% of them aren't using anything. We should get in front of them and see how they feel. So a kind of a founder who's half good will then justify, no, no, it's not the case, you got to do this that the other thing, right? They're kind of stuck into, you know, their original conception. The really good founders will be like, that's interesting, that's new data. How can we test this? Tell you what, set me up with 10 informational interviews with these guys. Let me see what they use. So that's what I mean by well-reasoned, but loosely all the opinions. Indeed. And what's your favorite personal productivity tool or habit? Spatiatext. Spatiatext. It's just so much faster. And it's gotten to the point where the transcription errors are probably less embarrassing than my typos and the auto-corrects. Interesting. Now, I use dictation on the word when I'm writing something, but I'm guessing this is also a good idea to create content and, and potentially, you know, get the word out there, right? Yeah. I mean, I'll tell you like in addition to the book, I've written maybe 70 articles in the startup press or the trade press. You know, I write them. I'm in the subway on the way to another meeting and I'm dictating right into my notes app. That's my first draft of almost every article I've ever written. Awesome. Awesome. That's actually really good idea. I can do that while I'm traveling in the trains and, you know, that's cool. Great. What's a new or a crazy business idea? You would love to pursue if you had time for myself or ones that I'm looking to back right now. Yeah. Well, let's say you won't, you won't back something up if you don't believe in it, right? So sure. Okay. I'll give you two answers for that. There's a deal I'm looking at right now. They make robots that clean the trash shoots in office and, you know, multi-family rentals or condos too, right? Doesn't matter. So instead of just pouring disinfectant down or deodorant down the shaft every night and then like twice a year having some professional manual service cleaning it. This is a robot. It kind of stays in its like little layer at the top of the trash shoe and at 3 a.m. it locks all the doors and it comes down, scrubs the walls. If there's ever a blockage, right? Carton got jammed in sideways. It locks the doors. It comes down. It knocks it out before it becomes a big jam but everything else piled up behind it. And the economics are kind of the same as the old school way of doing it. It's just really cool. My kids think it's the most boring thing ever but I think it's really cool. So I'm working on that deal right now for myself and for maybe a lot of the founders in the audience. I've worked on On and Off a tool that makes getting warm introductions to the right investors for your startup easier. So so many people do this poorly like the cold email, the spray and pray like it just pisses us off to be brutally honest, right? If you were selling a $50,000 software package to a large company, you would spend hours of research before you sent that email out but you want 10 times that much money or 100 times that much money from an investor, you're sending out the same generic. I did zero research email, right? The best thing I can say for it is we're not going to open it anyway so we won't remember you if you reach out to us later. So the right way to do it is you you know you go through your potential lists of potential investors however you get it, you're looking at their investments to make sure they are in fact relevant to you and then you're finding through your network, through LinkedIn or what have you. The right people put you in front of that. Ash, I know you know Fred Wilson at Union Square Ventures, can you make an intro and you make that easy. All of that is amenable to automation. The tricky part is linked in API doesn't let you have access to second degree contacts. So I banged my head up against that wall that wall on and off. I tried different other tools used AI in creative ways but one of these years I'd like to actually build that out properly. Yeah, that would be really cool. I mean usually the first stop for founders to go to find investors is engine network. So they have different hosted clouds. I think for one for Europe, one for US, one for Asia, everything. And then the moment you register you have to like subscribe to it. I don't know, it's $200 or something a month and then you get like tons of leads, tons of investors coming to you every day. We are interested and you find out later after spending so many hours that okay they are the people either trying to sell you something or their comments. I'm not saying they're not genuine investors there, there are but mostly you don't find genuine investors just by putting your pitch somewhere online and then just letting people pour in you have to do all the hardware, right? There's no magic bullet, you know crowdfunding also. It's not a magic bullet. I've got one company that's been very effective with it but by and large like you know you got to do the the lag work. I mean if it was easy everyone would do it. Yeah, exactly, exactly. Wait and then last but not least what's an interesting or fun fact about you that most people don't know. I mean there's lots of interesting things are fun to me but let me see it will be fun for other people. I guess as one of my hobbies is military history. So like when I'm not reading unfortunately business books or I'm not reading like sci-fi or fantasy to unwind or I'm not reading kind of like select nonfiction that I've missed that a lot of people have recommended. My go-to will be like reading about like Zerce's campaign against the Greeks or you know what really happened at the Battle of Agincourt. That's interesting reading. I think more and more easy access to more entertainment and you know these dopamine hits is just making humans in general I'm talking about you know very anti boredom but but in in in reality boredom actually gives you the creative juices in your brain. It gives you that feeling of being creative and one of the things which I found really interesting is reading so yeah definitely if you have something similar to that kind of lead just helps. I'll build on that a little bit right so I'd read 100% you can't hear yourself think until you create a quiet space for it. So if you're constantly listening to other things I'm it's great but if you're constantly doing and reading and watching and listening you're not actually hearing yourself yet. So one of quarter for my secret weapons on this is actually Sabbath. So I observe Sabbath I turn my phones off my computer off you know the TV off yeah right so I'll go out for a run in the morning before services but I'm running without my phone without listening to anything. So I am entirely in my own head at that point and you know if you've ever been to like Jewish services they're long so there's a lot of times where I've zoned out and I'm entirely in my head there but creating that space whether you know whether it has to be religious observance or even just you know one day and seven disconnected is not a bad thing reconnect with family with yourself that can pay huge dividends. Definitely definitely well Andrews thank you so much for joining me and sharing your wisdom with all our listeners if people want to get in touch with you people want to learn from you what is the best way to do it. So number one you can come to my website it's still a little bit of a work in progress it's Andrew be isn't boyacraman.com but I'll tell you a little bit more about myself I will also totally sell serving plug it'll show you how to get the book if you are investing if you have a startup that might be relevant to me first stop go to my LinkedIn profile on the LinkedIn profile it says right front and center what I invest in if you're in that space you can reach out to me send me an email it's again Andrew beacraman at gmail.com just say I saw you on founders pad podcast you know founders podcast follow up dash company name right it's like hey I saw you on that my startup does two or three cents is get a right front and center and then we can talk but if you're not in my space like your add tech startup and I don't do that you know probably not the best person for you to reach out to in that case by the book and it'll tell you you know how to find the right people to reach out to that you definitely Andrew thank you so much for joining us today and sharing your inspiring journey and then back for Vogue you're doing in the founder space it's been an absolute pleasure having you on founders podcast thanks for having me and great questions thank you