Ellen Chisa | boldstart

Mat Vogels: Hey everybody, welcome to another episode of Fundraising, a podcast where we interview early stage investors to give you, the fundraising founder, all the tips and tricks that you need to know about the fundraising process so that hopefully, kind of like the name suggests, it becomes maybe that much more fun in a process that is absolutely no fun at all. And today I have a very special guest. Ellen from Bold Start Ventures. We were just talking before this. I think Bold Start has one of the boldest brands in the game. And I have no doubt that I think this episode will be authentic and have some really, really good advice. So thank you, Ellen, for being on. Could we start a little bit with a brief background on yourself and then on the fun side, what you're investing in, average check size, and maybe some of the stages that you're interested in?
Ellen Chisa: Yeah, definitely. I guess going way back, I'm originally an engineer by background. I went to a tiny brand new engineering school, so one could call that my first startup experience. ⁓ and then did a bunch of different engineering and product things along the way until I became a founder and started a programming language called Darklang. I was very motivated by the idea that everyone should be able to make software and I thought an easier programming language will do that. And it turns out the answer is actually just text and using text to do that, the ultimate programming language. So right direction, wrong implementation. through my time working in Dark Lang, Ed and Elliot had invested from bold start into the company, and so I really enjoyed working with both of them. And after that when they said, Hey, why don't you come hang out for this for a while? I said, Sure, let's do it not really knowing what that would mean. now we're six years in and I'm still here. ⁓ Really enjoy it.
Mat Vogels: I love that. Before we go into maybe the fun specific things, can you talk a little bit? I always feel like founders that become investors are the best investors to have on a cap table. ⁓ you know, whether or not the returns echo that is a whole other story, but I think from for founders listening, when you can have a founder or sorry, a VC that was a founder, can you talk a little bit about the empathy that that brings to you and the experience you can have for both worlds?
Ellen Chisa: Yeah, for sure. I feel like anytime a founder is calling me and they're having a bad day, I feel like sometimes it think of it as like, ⁓ no, I'm gonna call and I'm gonna give you this bad news and it's like this much worse that I have to tell you and you're gonna be mad and I'm like, I'm never gonna be bad. Like your day is worse than my day in this scenario. Like I've been there and it was very hard when things weren't going well. so I think that like y I think you just have more understanding of what that's actually like. I think it also one of the things I brought to it is I feel like so much of the day to day of startup is just like Something happened. You're resolving it. Like you're reacting to a bunch of different things even as you're being proactive. And so I think it's easy sitting from an investor seat to like, Why don't you just do this obvious thing right in front of you? But we only see the one thing and you're in fact seeing four hundred things at the same time. And it's not so obvious when you have the all of it, all of the details.
Mat Vogels: Yeah, and you can from the investor standpoint sit in that chair and know that there's there's more behind the scenes and that you're not gonna overreact on some news because you know that there were so many things that probably led to that. I love that. On the bold start side, what are some of the the industries that you're investing in, average check size, and then the stages that you're focused on?
Ellen Chisa: Yeah, a hundred percent. ⁓ yeah. I love this because I feel like average is the like most misleading word for us. And people like founders ask me this all the time. And I'm like, there's not really an average because we do things in Inception. Like not every company needs the exact same number of dollars on day one. And we purposefully built the fund. It's a $250 million fund seven to be able to give you the right amount of money on day one. If that's like $500K because you're just getting started and you're exploring and it's a friends and family, but you want to stay as part of your friends and family. Totally fine. And if it's that first round is gonna be ten million dollars, fifteen million dollars, that is also completely fine. And so if I average it might be like five, and it would be completely misleading. so it's a no average check size, very much like maybe it's five hundred, maybe it's two, maybe it's ten. and area wise Well we started saying autonomous enterprise, which I I quite like. you kind of ignore into the categories that founders will often recognize. We do a lot in cybersecurity, kind of a quarter to a third of any given fund tends to fall there. ⁓ lot of infrastructure and developer tooling, ⁓ which was obviously the side I came in from. We do applications like superhuman, the email client. ⁓ Ed and Elliot had worked with Ruble at his last company and again on Superhuman. And then recently we've also done a lot more deep tech leaning stuff, which was really I wanted to bring back in a lot of the things I'd kind of done before my career in software. So we led the Inception in Generalist AI, for instance in robotics. We've done some stuff in tech bio and I'm kind of always looking to see we can have a right to win there and where we can be good partners. ⁓
Mat Vogels: I love that. And then yeah, I I forgot with your technical background, certainly as it as it involves investing in technical things, that gives you another it isn't the right word, but I from a founder's perspective, a unique value add that you get to bring to the table other than just being capital, which is great.
Ellen Chisa: Yeah, for me it's I've always said like everyone every investor will say it's about the people and it's a hundred percent about the people, but for me, even when it's about the people, it's a little bit how the people think about product and how the people think about engineering, which doesn't sound like a technical thing, but I feel like there's something in like if you've built enough things you can kind of recognize how the other person is talking about building something, and that tends to be where I like to build rapport with people.
Mat Vogels: Love that. So these are the next few questions are questions that we've had founders kind of nominate in or or ask that I ask. The first one is what is your favorite part about the job and being a VC, especially now that you've experienced the founder and the VC side? And then what is your least favorite part about the job and being a VC?
Ellen Chisa: Okay, my favorite part, which I think is very is kind of silly, but it's very much an ops person thing. I love that it's basically being on call all the time. Like when you're hearing from founders, like there are definitely times you're hearing where someone just wants to catch up and like you're you're a good sounding board, but it's often that something either very good or very bad has happened and you're kind of like immediately in a war room scenario. And I think that is very fun for me.
Mat Vogels: Not a lot of in between. Yeah.
Ellen Chisa: There's not a lot of in between. There's like not a lot of like there's no bureaucracy. There's no fluff. There's like no waste of time. Like every conversation you're having is good and interesting. And I think there are very few jobs where that's the case. Being a founder is probably also one of them. And so I think I I really appreciate that. think the I'll give you two different least favorite things. I think one of the best things about building a founder is you're recruiting a bunch of people to your mission and you're all collaborating on the same piece of work and you're building it together. And in a fund, you're all collaborating together and you're all supporting founders together, but there's a difference between collaborating together and building the same object together, be like be it physical object or a software object or whatever it is. And so I miss that part. although it's not really a least favorite thing. I think my actual favorite is how often you end up having to say no to people and the fact that like, You're just saying no over and over again. But for like any given person, took the time with you to hope that you were going to get a yes and like they put themselves out there to ask to work with you. And so like that kind of rejection process is unpleasant. and I probably spend more time on it than I should.
Mat Vogels: Yeah. Do you feel like though that you have a again, going back to the empathy kind of piece of being a founder, you've probably heard no a lot as well, maybe from VCs, it maybe helps you in in giving that answer, although it doesn't get easier for sure.
Ellen Chisa: I it helps in that like I actually I try to write like the real reason down for why I'm saying no. And like the hard part is like at the end of the day, all of us are kind of like we're black boxes of like you're saying no because of the overall picture and you can kind of point at a s couple specific things that might be relevant. but I I try to do that as a result.
Mat Vogels: I like that. What are some things that now that you again have crossed over on the VC side, that you could enlighten founders with in the day in the life of a VC that you think would provide the founder with maybe a sneak behind the curtain, better understanding, so that they have maybe more empathy on the VC side?
Ellen Chisa: I actually had a really good conversation with a founder in the portfolio about this once. I think when you're a founder and you're in fundraising mode, you're having kind of the same types of conversation about your company over and over again. So like you're comfortable, like you're telling the same story. It's also you're doing it all the time, even when you're not fundraising, and like you are always anchored in that worldview. For the VC that you were talking to, they like they could be coming from this podcast where they're like kind of thinking more philosophically about this work. They could be coming from with the founder who's having the worst day of their life. They could have been talking to a founder who's having the best day of their life. Like ⁓ don't really know what person is walking into when you're pitching them. And so I think when founders have like the sense of being like, okay, they're both intellectually and emotionally switching into this room, like it's on me to try to do a good job of doing that. But when the founder like can match that and kind of say, like, I shouldn't just like monologue 20 minutes before checking to get understanding or I know this person knows my space really well. I'm not gonna tell them about like why software developers are interesting. Like there's like middle ground and I think founders can realize that they're walking into a room with a person who could be coming from anywhere and just like make sure they ground the conversation that they wanna have early on.
Mat Vogels: Wow, I I I haven't even as a V C thought of it that way, but you're absolutely right. When you're a founder, you're hyper focused and you're only like a degree of separation away from the main storyline of what you're building. But on a V C you're exactly right. Like any given day, your mood or your your idea of the world at that given time change fairly dramatically from one day to the next. ⁓ course.
Ellen Chisa: Yeah. And you don't want leakage, right? Like you don't want to have a conversation with matter that's pre like completely normal but something bad happened before and so then they think you're responding emotionally negatively to what they're doing and it's in fact nothing to do with them. And so I think it's like also on people to acknowledge how they are when they're walking into something and not give bad signals.
Mat Vogels: Yeah. That's really good advice for founders. And, you know, not take it personally if if it feels like the VC is interested or that they're having a bad day. I mean, there's empathy across the board here, but I think you're right that VCs certainly have more of this sporadic of thought where they could be landing at that moment. ⁓
Ellen Chisa: Yeah, it's almost certainly not about you if they seem upset.
Mat Vogels: Absolutely not. Yeah, for for sure. Are there any areas or sectors that you personally are really excited about right now? Is it it could be from a consumer standpoint and something that you're not you're necessarily investing in, but also from an investment lens, anything that you're personally excited about right now?
Ellen Chisa: Yeah, I mean, so I guess from the investment lens, and this really started two and a half years ago now, I started going like, Okay, like I'm most interested. I felt like we were starting to build like software on top of software on top of software, where every slice was getting really narrow and it was kind of getting it like started feeling a little house of cards y to me. Whereas like, okay, like there's less like white space here than there used to be. And I started going like, okay, with this new set of technology we have, there's gonna be a lot more chances to actually overlap the physical world. And so I started thinking much more about that. what I've generally found with bold starts, since we're always investing in Inception, usually do things and then a couple of years later everyone will start talking about them. And so then we'll kind of shift on and start thinking about different things again. so I I'm still extremely excited about that. So like any of the robotics, any of any of the tech bio, we obviously have a company together that's in the mining space. That I'm also excited about. I would say what I've started thinking about recently is feel like even the generation of AI native companies to some extent feel like we kind of bolted a model in or we bolted an agent in. It's not like a truly different surface. I feel like A's AI will look much more invisible when we get like truly AI native products. I think granola is probably the best one for me so far. And so I'm thinking a lot about what consumer surfaces are go are going to get another round of updates. Like I think documents will maybe get another round of updates. That would be cool. I'm like a Microsoft Office nerd by background, so that's kind of always one I'm looking at. but yeah, just high quality consumer products.
Mat Vogels: Yep, I like that. That'll be exciting. We're in for a yeah, a wild ride over the next few years as we kind of settle or at least continue to accelerate, who knows, on on the AI front. Last question before diving into the fundraising process itself, a time for for you and or bold start to shine a little bit. Why should founders pick you andor bold start to be on their cap table? ⁓
Ellen Chisa: Okay. I like I honestly think the most obvious one here is like like you're s we were talking about our brand earlier. Like we're pretty clear about who we are. And so like you probably either like us or you don't. And if you don't, that's okay. And if you do like us, like that should be a pretty good signal for you that like you we're true to like the internet. and like Ed and I Elliot and I are all a little bit different, but like you'll you'll get the overall vibe. Beyond I think like the best reference we have is a lot of the founders in the portfolio have chosen to work with us again, either ⁓ They found another company, they've referred their early employees to work with us as their investor. So like people come back. then the tactical stuff, like we only do inception. So if you're at the very beginning and you want a partner who understands what that really means and is gonna be patient and is not kind of talking about a lot of growth like premature things before you've even like gotten the first product done, like that's definitely a point. And then I think we are also we're pretty direct. we want people to learn and we want people to learn on their own, but like if we're thinking something. We're going to tell it to you. And then like you as the CEO founder can decide if you want to use that thing or not. But most of the people who we've worked with have said they really they value that. and so maybe it can be like hard in the moment, but they think it's better in the long run.
Mat Vogels: Yeah, I I mentioned the term authenticity earlier and I feel like that that's a something that comes through on on the Bolt Start brand, which is which is great. And it like you said, it may not always be what a founder wants to hear, they're gonna ⁓ it, not only at the beginning, but it's a ten year journey. They're gonna continue to appreciate it more and more as the business maybe gets a little bit harder. ⁓
Ellen Chisa: is rough on us too. Like we don't like when someone's mad at us for a few months. But like that's part of the job is you say the hard thing and then you're like, Well, they're gonna mad at me, but hopefully it was the right thing to say and six months from now they'll be happy that I said it.
Mat Vogels: Of course. Of course. Yep, yep, agreed. It's like it's like parenting in a in a weird way. right. Let's go into the fundraising process. We break it up into three different parts. The first is about getting in the room. A lot of founders that are listening to know how they can take their pitch, their idea, their baby, and present it to a VC that will hopefully give them money. It's especially true at the inception stage and the very first checks in, which will be great feedback from you. Let's start with what feedback you would give founders at the very, very beginning, as they're even just thinking to go out and fundraise. How should they start thinking? or characterizing list of funds or individual investors or where they start? I know it's kind of a broad question, but where should founders start at that very beginning of the journey when they're like, I want a fundraise ⁓
Ellen Chisa: Okay. I have actually advice I give people here, that I think is good. It's what I would do. I think you should look at companies that you admire in your space that are not directly competitive and go through their cap table and then reach out to those people. Because like chances are those people are for some reason, maybe it's just it was a personal connection, but now they're least a little bit familiar with your space from that other company that they've worked with. And so I would be kind of looking for any signals that suggest that an investor would be interested in you. Because especially if you're cold emailing them, there's gonna have to be some reason they actually answer. ⁓ so that's the kind of starting place. I guess you could also do kind of the cold internet research on the same topic, but I have found it's like more efficient to just go through other people's lists of investors.
Mat Vogels: And is there guess like a any rule of thumb ⁓ how interesting or are you looking at size stage? is it just yeah?
Ellen Chisa: I so yes, so I think stage is very I think very important. everyone will feel differently about it, but like you want to be targeting people who actually do what you do. Like if you're trying to raise an inception round and you email Goldman Sachs, I don't think that's really gonna be very helpful for you. Same way, if you're trying to IPO your company, ⁓ you probably don't want to email me. If not, it'd be very helpful. and so like I think ⁓ making sure the person invests in the kind of company you are building is very relevant. ⁓
Mat Vogels: Yeah, of course. Yeah. Yeah.
Ellen Chisa: So and I think that's probably more s a stage sector. I feel bad. I definitely feel like sometimes when people invest in the sectors that can be harder because people don't necessarily focus on them, they end up going broader because they're like, No one does this. I'll just email everyone, but I think you're often better off having a more curated list of people to talk to.
Mat Vogels: Yeah. What I mean kinda too is that I I feel like there's a lot of VCs out there, and you probably get this all the time from founders, where they say that they invest at inception or the earliest stage. They label it on their website even, but when it comes down to it, they end up being like, ⁓ well we'll follow along and you know maybe when you get some traction or you know, you get to five million ARR or whatever it might be, then they're now early stage investors.
Ellen Chisa: Yes. This is my favorite thing about being only inception. Is like sometimes I'm really bummed 'cause I need someone great and they already raised a pre seed or they already raised a seed and I can I can't work with them unless I wait for them to come around and have another company in ten years. But on the other hand, it is so nice to be able to say no and not like send me updates continuously for the next five years, even though it's unlikely that like I will get there in the future. it is nice to have that clarity. I do think I mean
Mat Vogels: That's nice.
Ellen Chisa: And everyone's kind of gonna have their own way. And I think it's fair for founders to push on this. So like for us, inception, but some people who are inception say it's like only about the person. We usually expect we don't expect you to have built anything, but we want you to be able to say, like, this is what I'm doing first, and like this is my hypothesis and this is the unique space, and also be able to say, and this is why it's a large market. And it's actually quite a lot of thinking work. Or like background work or like pre work before you might even start like you might not even start at a company, but you've spent ten years kind of thinking about your space and you know the like the shape of what you want to do now. which is very different than just like we back people, even though you can do both of those things in the session.
Mat Vogels: Yep, yep, I like that. Is there a right or wrong way that you see founders in front of you or or getting in front of other VCs kind of at this early stage?
Ellen Chisa: I think especially in the last six months, I've started getting an onslaught of cold email that feels a hundred percent programmatically like programmatically generated. Like no one has any idea why they've sent these emails. They don't even know they've sent them. You're like still on their cadence even if you reply and say no. and that volume is so high now that if I open an email and it immediately reads like I can tell a model wrote it in the first three sentences, ⁓ don't answer the email because I feel like the email wasn't like particularly like I'm a real person reading the email. If you want me a real person to read your email, send me an email that you you actually wrote. it's totally fine to have AI augment things or help or like train something to use your voice. But like if it like clearly reads like, ⁓ this person just said please scripts and emails if he sees and blast email it everyone, like I'm not going to answer. so say that's the wrong way right now. The right way I think is just like being thoughtful about it. Like I've definitely had people reach out who's are like, ⁓ like I And I'm not saying everyone should go look up dark to email me things about dark, but like for people who genuinely like followed along with dark, they're like, remembered like when you launched this thing and I watched this video and I'm like, ⁓ like that's like a little personal rapport that can build into it, or like, when you did this work, like I was have a strategic question about this. And so then I know even if this isn't an investment I can make, we ⁓ like at least are gonna have a good conversation and hopefully like they'll get some value for the company out of it. Yeah, it's just like if it's like if it's clear you're emailing me for a reason and there might be a fit here, like I'm gonna answer.
Mat Vogels: Yeah, yeah. I we've heard this all the time where the the inbound now is kind of overwhelming. But I think it's it's still pretty hard to ⁓ surface or come above that noise, even if you were to write something that feels authentic. It's this is why we can't have nice things. Like the the hundreds of other emails kind of ruined it for you, even though you are doing the work and and putting it together. You're better your odds are still better, but I think that it still hurts across the board on the cold outreach. Not that you shouldn't do it. In my last companies I fundraised off of cold emails but it is it is harder I think today. What are your thoughts on either yeah, warm introductions, in real life meetings, or trying to put yourself in positions where you don't have to do cold? Any feedback, suggestions, recommendations on that side?
Ellen Chisa: Yeah, I think I there's a good blog post. I don't remember who wrote it of like the hierarchy of warm introductions. But like certainly if you know a founder that I work with and they're gonna say you're the greatest person ever, like I'm going to meet you. Like definitely a thing. or like someone else I've worked with before who I really liked working with. A lot of the time when at least I say no to a meeting even after a real email. It's often that I like I know that we're not going to invest in the space or like I've already spent a bunch of time thinking about it and I'm just like, no like I don't want to give you the false hope of getting on the phone for half an hour while I sit there being like, Yep, still not gonna do it. Still not gonna do it. Yeah. And so from that standpoint it's kind of like I like I don't know if a better email makes it better, as long as like the email actually makes a set of eyes or like you get it through a warm intro or you run into me in person, like I I don't think it really changes the end outcome most of the time.
Mat Vogels: Yeah. Yeah. Yeah. Yeah. Are there any things that they can be, you know, put in that that email? being authentic and feeling real is great, but you looking for a clear of the problem, a clear statement of you know why the founding team, like what are you hoping to get from that email specifically before you jump into a pitch deck?
Ellen Chisa: Yeah, I should know what you're doing. The thing I like least is when someone sends me an email that is two sentences and is too vague to know what they're actually doing and then I have to reply to say, But what are you doing? 'Cause I'm like, Well you just made an extra loop for both of us. Like we none
Mat Vogels: Yeah. Especially if they don't send a pitch deck, which I get more now. I feel like let me know if you want a pitch deck. I'm I'm not replying to that email. ⁓
Ellen Chisa: Right. Yeah. So I feel like I just wanna be like like I wanna have a good sense of like ⁓ like what are the like the three sentences of this that like make me understand what you were building and why.
Mat Vogels: Yep, I like that. And in the pitch deck itself, you do feel compelled and you open it, ⁓ there any slides that you think founders should spending more time on ones that you end up being attracted to that that help you get over the the edge?
Ellen Chisa: I definitely don't spend much time on Tam. Like I feel like either it should be obvious to me that your market is huge or it's probably not. ⁓ so like I don't like look at the math there. Like I mentioned before, like I tend to like get to know people by learning how they think about products. So I'm like usually looking for that through line of like what are they building and why.
Mat Vogels: I like that. Are there any slides? So the TAM slide that you mentioned maybe not being there. Team slide, what are your thoughts on team slide? We hear that one as being one that everybody loves and wants to see. your mind, what makes a good team slide and then what makes a bad team slide?
Ellen Chisa: Hmm. I think this is like very bespoke to investors, so I don't know if people should change their team slides based on just what I like. At the end of the day, I really care about you and your co founder. If you have a co founder or multiple co founders, I I think people sometimes try to make it seem more credible by adding a bunch of advisors, but I feel like the issue with that is it's very hard to differentiate, like, is this just someone who talked to you once? Is this someone who has equity and signed an agreement? Like, is that agreement like I feel like it raises more questions for me than answers most of the time. Like I really just want to know about you. You're the person I'm gonna work with for the next 10 to 15 years.
Mat Vogels: Agreed. All right, let's say that they've impressed you enough to hopefully go into that first meeting. It's kind of the the first time that you're gonna get a real good understanding of what they're building, the person, all these things. So it's an important meeting. what are you hoping to get out of it as a VC when you're meeting that founder for the first thirty minutes? What your goal and objective going into that?
Ellen Chisa: I'd large trying to give it this understanding, like, are we the right people for this person? Because like so much of Bullshit is like me and Ed and Elliot, and we will help ever like all of will help everyone in the portfolio, regardless of who like originally worked on something. and so sort of like, do I think we will be helpful to you is big part of that. And I think a big part of that is like, do I the world going the same place you see the world going? So like experiences are when someone comes in is like, hey, this is what's gonna happen. This is what I what where I see, this is what we're gonna do first. And I'm like, Of course. Especially if it's something where like I haven't sp like I like we're thesis people, like I don't sit down and write a bunch of stuff. But if like you come in and you tell me the story and I'm like, ⁓ yeah, yeah, no, that's definitely gonna happen. That like completely matches my worldview. Like that's a pretty good indicator that it does make sense. Because like I'm gonna have the intuition that hopefully matches yours. And like I might still point out different things, but like we'll at least be rowing the boat in the same direction. I never wanna be in a scenario where like I think the founder should be doing something different with their company than they think they should be doing. It's their company. So that's a big piece of it. And so for me, it really like it is I will spend a lot of time getting into the like, okay, like what like I'm trying to picture what is the first revolution here. Like what is the first thing that you can prove that is currently unknown? And if we succeed in doing that, we're really on the right track. And so like that's an important thing for me to understand in a first meeting as well.
Mat Vogels: Yeah, and how much of that is back and forth? the reason I ask is we have a lot of founders that are unsure of how much of this is a presentation versus a conversation. Obviously it depends on the VC, but ⁓
Ellen Chisa: ⁓ It is 100% a conversation, but it is a conversation that you are the driver of. Like you need to be like getting us back on track because like I might just wander off and like like you've got to give me some input because if you're just telling me boring thing after boring thing after boring thing, like it's not gonna like reading slides is not going to get me to make an investment. But like if you give me some context and then I'm like, ⁓ what about this? Like, yeah, sure. Like, let me go one or two leaps on that. But if you're like, ⁓ no, like we've spent five minutes on this like tangent because Ellen just got curious about it because she is an intellectually curious person, be like, hey, like, I'm happy to go into that another time, but I really think we should like refocus on our main point of this and just like reel it back in.
Mat Vogels: Gotta rope it in. That's really good advice for founders. Yeah, I always say to to maintain and take control of these meetings as best you can. You should obviously the room and and if Ellen's getting excited about something, you obviously want to be able to to pique those curiosities. But it only 30 minutes and if we don't get through what we need to, ⁓ sometimes it's to schedule the next meeting or things bleed over and and all that as well. So yeah, keep it controlled as best you can.
Ellen Chisa: And I think having the slides up helps anchor on something too. Like even if we're not just like you're presenting over and over again, it's like nice to have like a visual aid and then you can go back and forth. It like I think it helps founders remember that they are driving.
Mat Vogels: I like that. Yeah, the next question I was gonna ask you here is deck or not to deck, it's it's how often do you wanna come in and just see a deck? ⁓ they lead with it? I I agree with you, kinda there, maybe you're you're saying the same thing. I like to just have the deck up all the time. Like bring it up, maybe present the first like couple slides just to visualize some quick points and then maybe go off from a different direction. But To I don't like it when it's brought up later where you talk for a little bit, it feels kind of aimless, and then it's like, ⁓ now I'll hop into the deck. ⁓ I like I think the deck first and then it kind of like you said, it puts it on rails almost a little bit, but then you don't need to just present slide by slide as you go through it.
Ellen Chisa: Yeah. I think it's because otherwise you have that like first aimless conversation and you're like kind of building a picture in your head, but then you hit the same things again and it's so it's like I don't know, you're really trying to get the most out of the thirty minutes that you have. And so you don't want to be doing anything twice.
Mat Vogels: Yes. Yep. Yeah. Another quick question that we have founders ask all the time is whether or not they should bring their entire founding team onto that first call. Do you have any thoughts or opinion on that?
Ellen Chisa: I would generally say no. I think it's like it's i it like it just adds to the group dynamic, right? Because then you suddenly have like three lines of communication and then you kind of have the like how do we hand off between each other? I mean, with Boltz art we only work with technical founders. And so like I don't like I could see it being a different scenario if first I don't know, like if it was a consumer company and someone was like very growth y but no one believed they could build something and then the technical person came to like talk about building things like I could see scenarios where maybe it would make sense, but I would say most of the time I don't find it improves meetings. I think it is appropriate, certainly like later in the process. Like if you're getting there and you're like really close to like a term sheet stage, like of course, like we want to meet the people you're working with. It just doesn't have to be first 30 minutes.
Mat Vogels: Yep, agreed. Are there any questions that you think founders I mean going back to taking control and ownership of this meeting, are there any questions that founders should put on themselves to ask the VCs during this meeting, even if it's at the end?
Ellen Chisa: I actually it's funny, smart people sometimes do this. They they will ask what you think after the conversation and be like, ⁓ like what do you think? And like as someone who does a lot of processing offline, I'm kind of like, ⁓ like you're really putting me on the spot here. it's also true that I often do like have a gut sense of where I'm at after the first thing or what I would do next. And so I don't mind being pushed on that. And I think it probably does give the people who ask me a better read of what's going on.
Mat Vogels: Recently I've had some founders that lead with questions right out of the gate where they ask something like that to almost get it started, where it's a was exciting enough for you to take this meeting? Like leading with that, and then having the VC I've I've seen it backfire with some founders where sometimes VCs will take it to where they feel off guard and then they don't have a good answer and they almost feel like they're being attacked isn't the right word, but all of a sudden they're now kind of like, this isn't how I expected this meeting to go, and it throws everything off. But other VCs can answer those questions and it becomes comes an excitement like well we're really excited about the fact that you're thinking about this because we have a portfolio company that did this and we know these customers that like this. Cause then as a founder you can kind of drive the conversation in these ways that feel it. I've seen it work kind of in in all ways, but it's it's a dance and it's not guaranteed at all times.
Ellen Chisa: Yeah, I think that it also goes back to like where the person was like, that's definitely gonna work if it's someone who's been like chasing you for a long time and they're really excited about the company. It's not gonna work as well if it's a week where someone was kind of like, like, mm, I'm on the fence, but like I have some time. I love meeting like I th there's probably like some sort of argument here of like how convicted should you be to take a first meeting at all. You certainly can't say, I'm only gonna take meetings where I'm gonna write a check, because if you're only writing two, three, five checks a year, that would be very few meetings.
Mat Vogels: Yes. So true.
Ellen Chisa: And on the other hand, you can't take every meeting. And so like there's always gonna be some zone like you might be s like I've definitely taken meetings where I was didn't think I would get there and then I did.
Mat Vogels: Yeah. Yeah, and you're always surprised by those things too. especially if they were introduced to somebody that you trust and value, even if the the the entry you're like, I don't like this, but you trust the person that made the introduction and then you end up liking it. ⁓ Are any mistakes that you see founders make during these these first calls? I mean, not just the opposite of what you were saying, or maybe they don't do a good job of convincing you of the problem or articulating or storytelling. Any other tactical things maybe that founders do on these calls that are a complete mistake?
Ellen Chisa: Is that right? I mean you called it out, but like insisting on staying fully on script is definitely a tactical error. I think assuming the investor knows either too much or too little, there's like a a right place to be. The other one is definitely like trying to turn it around. Where like said before, like I try to be we try to save people time. And so if if we're we know we're a no, we try to say it right away. Like to the point where if I realize I'm a no twenty minutes into a meeting, I'm going to tell the founder that.
Mat Vogels: Wow, that's awesome.
Ellen Chisa: And then they can have ten minutes of free time with adventure capitalist to get any input they want, kind of like our podcast, but like live. sometimes when I do that, which really like I I do do it because I respect people and their time and their effort, ⁓ people will like try to turn it around and start arguing live and I'm kind of like, ⁓ like arguing with you doesn't it doesn't change the like the overall meta that I have.
Mat Vogels: I have had founders on calls that get argumentative when we're like, ⁓ but what about this? And you ask a question that you think you're just being curious about, but it strikes a weird nerve and then all of a sudden they get they're very vocal and like you could tell that there's like a switch that goes off. sometimes that's that's not a good sign. ⁓
Ellen Chisa: I was in this once from the other side as a founder. Not like yeah, it was
Mat Vogels: Yeah. Where you feel like you wanna be like, You're you're wrong and there's you know, obviously VCs are wrong more often times, so f I always tell founders to be you know, give a little grace on those, but it can be hard. All right, going into final process of the fundraising, this is ⁓ such a weird like blob because usually you're lining up all these intro meetings, the rest of the fundraising process is hurting cats, you're building momentum and a little bit of FOMO and you're trying to build out your cat table. It's definitely the meat of the process. Could you talk maybe a little bit about starting with on how Bold Start handles it, what is the the diligence process look like or the process between Ellen just had a first meeting to you're you're writing a check or or sending things over on a close?
Ellen Chisa: Yeah, I think there's two important things we do there. is we tend to make introductions to potential customers. Like we want to understand, like we usually think this is a large market, but we want to hear that like the way you're thinking about solving it is going to be interesting to something, someone on a like reasonable timeline. which means actually I spend a lot of time in that initial call trying to like get very clear on like who would send this to to be able to have them be like, Yes, I want to angel invest, yes, I wanna be the first customer, yes, I wanna be a design partner. Like I'm looking for those signals from people we know and trust. And so that's a big piece of it. We often will try to do them two founders in the portfolio if they're founders in the portfolio who fit the bill, because then you can kind of reverse diligence at the same time. We're trying to be efficient. and then the other one is just because like we like we're very unsiloed as a set of people and we are all distributed. So like we're not in person in an office together all the time, which means it's like very like push, pull, who can help with this, who can help with that. we do like for people to meet all three of us, but like it's not I don't know, it's like I like don't want to say it's a partner meeting 'cause it's not like the thing where like you walk in with the laptop and you do presentation and there's twenty people staring at you and it's a whole thing. It's like very much like it's kind of the same thing again, but with three of us and with like some more nuance in the questions.
Mat Vogels: But again, it's probably more like real conversations because I I've been on those too as a founder where you go in and there's like partners ⁓ you've net you haven't met most of them. So it just and you're kind of in this weird position where, especially if some of them start asking questions and you're like, ⁓ do I have to spend five explaining something that I've already explained to like the other partner like two weeks ago? so there's value. Smaller team, but also I think I could say the bull start more down to earth in real conversation, which is nice. ⁓
Ellen Chisa: That's yeah, that's what I think is 'cause like we all want to be having a conversation we're interested in having too. None of us are I don't know. We aren't people like to sit and listen to ourselves though.
Mat Vogels: Yes, yes. You got time for that. Yeah. It's it's kind of a hard piece where when founders are in here, sometimes they have to make decisions on to keep on the cap table, who to keep off. Sometimes it's picking the lead. Maybe you have a little bit of allocation left and you're trying to pick it. Maybe it's even just the beginning and you find a VC that feels like you know in your gut is telling you is a red flag and you don't like it, but offering you money and so you kind of feel there. Any just advice you would give founders that are picking a VC if they're lucky enough to be on their cap table, what they be looking for. What characteristics, what things are are green flags, red flags? Because again, a lot of these founders have never done this before, and it's such a new process.
Ellen Chisa: Yeah, I would definitely This may be a little fluffy, but like I would definitely think about like why do you want this person? Like what role are they gonna play for you in this company? Like beyond just capital, obviously. And then I would like kind of ask yourself the things that indicate if you would work well with them or not. Like would you feel comfortable giving them feedback? Like if they like if you thought they weren't being very helpful as a board member, would you be like would you talk to them about that? Do you think they would adjust if you did that? you feel comfortable with them advocating for you? Like this person is also gonna be running around in the universe talking about your company. Do you think they understand your company well enough to do that? Like, do you think they'll say the right things to people? Do you think they'll talk to the right people? Like, how do you feel about the idea of them pitching your company? and even more high level than that, just like how do you feel after talking to them? Cause like there's some smart people that you talk to them and you walk away being like, This is great. I learned so much stuff, it was really fun. And there's some smart people where like I walk away from talking to them and I'm like, I feel dumb. I don't think I'm Mm, that wasn't good. And so like you wanna like always walk away from those hopefully. with that person making you you feel better. Yeah. And so I guess yeah. ⁓
Mat Vogels: It's oddly vibes based. It's like there's a lot of vibes that go into it in a weird way, but I'm a kind of a vibes person, but I still feel like there's vibes in that that you just kind of feel, and you're exactly right. You have to feel talking them, meeting with them, texting them when things are going wrong, asking for feedback, giving them feedback. Those are all things that you kind of feel and I think in your gut a little bit. Ooh.
Ellen Chisa: Yeah. Like would you wanna hire this person and have them like obviously we're not gonna be your office every day, but like if you were thinking about it from that perspective, is it like the same choice?
Mat Vogels: Yeah, that's that's really good advice. are there any mistakes you see founders make kind of in this process? 'Cause again, it it may be even said differently if you want to slide it in there for building momentum, building some that FOMO, any advice on you on how founders can do that, but then also where you see biggest mistakes in trying to do that during this part of the process?
Ellen Chisa: Yeah, the part ⁓ the one that comes up it's not super often, but occasionally that I always feel bad about is founders sometimes misread early customer signals where like I'll make an i an introduction and like generally if I'm introducing someone, like they're gonna be nice to you. Like they're not gonna be cruel, but like there's a big difference between like, ⁓ that's an interesting idea and can I buy that? Like there there's a huge range there. ⁓ and so I think founders sometimes will read like a pleasant conversation as being like that was great diligence and they should definitely do it 'cause this customer said it was a cool idea, which is like it's not gonna get there. And so I think that can kind of create a a rough point when you don't actually get there even after making those conversations. I think the other one is just like The FOMO art is hard, right? Like you can't push people too hard. Cause like people will like like I think a thing that can go wrong is like I might like someone and then I'll like they'll ⁓ well we're deciding on Friday. And I'm like, ⁓ like I can move by Friday, like when I really want to, but like when I look at like the calculation here and the type of diligence I want to do, and maybe it's a new network or whatever it is, like I'm not gonna do it by Friday. And then they're like, wait, wait, wait, wait, never mind, you can have longer. And I'm like, so it wasn't really Friday. And like that kind of definitely I think that's an unforced error.
Mat Vogels: Yeah. Yeah, it's the hey, we're closing on Friday and then I get an email next week or two weeks where it's like we have more allocation all of a sudden or we've extended the timeline to think through more and it's tough to to lose that. And sometimes it's true, and to your point earlier about customers giving mixed signals, I think VCs are even worse at giving mixed signals. So founders can sometimes take an excited VC meeting because VCs always want to feel excited about what you're doing as super strong signal, and then they're gonna be like, Ellen, this VC, they loved it. They're definitely writing a turn. sheet and then you could text that VC and they're like, ⁓ no, we're we're we're passing and you know, tomorrow. Yeah. Yeah.
Ellen Chisa: ⁓ yeah. It it's like it's like they met one one junior investor at a giant like yeah, it's like a whole thing. Yeah. That's definitely also a mistake that happens.
Mat Vogels: Yes. It is tough. It's it is really tough. But if you can
Ellen Chisa: I've had to explain it's like the job for investors, like they want you to like them. Like it is kind of salesy, like we're all selling a commodity product. And so like the investors want you to like them.
Mat Vogels: Yeah. Yep. And I think the hard part too is a lot of these investors are multi-stage, ⁓ also don't want to burn the bridge. Maybe they can't get there now, but they maybe write up check its seed or series A. And that's the problem I think with multi-stage is it's really tough to get funding from them, but also to get really honest answers from them because they to keep their cards open for the lifetime of your journey, which can be difficult if you get really good feedback. All right, let's go into The last bit, which is after the fundraise. it feels really exciting. You celebrate for five seconds, but there's this weird shift that happens, I feel like, where founders go from fundraising mode to you know back to building mode. Any feedback that you would give founders that just closed around and how they can kind of snap back building mode, what should they focus on for the first like week after, three months after? 'Cause it is a transition, I feel like.
Ellen Chisa: Yeah. I especially depending on how long the round takes. I would definitely say one I see, which I love, is many of the teams we work at Insecture, they have everyone lined up to go. And so it's basically like I wire the money and they hire six people that week. And then it's like everybody starting together, which I like I love. And I've definitely the people who I've seen do that who kind of like have that forethought to play in the slate of people and they know the slate of people they want to have. Those companies really do execute. It tends to go very well. so I kind of like
Mat Vogels: Wow, that's awesome.
Ellen Chisa: That I'm trying the other part of it is like I think it's really easy once you raise venture capital, get distracted in like the game of like I have a startup and I'm being a founder. And it's like playing a character on TV, basically, in like a little bit. Like I'm doing I'm doing the thing. And I'm like, I don't actually care if you do anything other than build a thing that really matters that people want. And like if you don't go to all the parties, like you know what? You're gonna be just fine.
Mat Vogels: It is.
Ellen Chisa: It'll be fine. If you build a thing that people want and it's growing very quickly and everyone is excited about it, people are gonna give you money. They're not gonna go, Why weren't you at the whatever, whatever meetup on Tuesday of whatever year? Like no one cares. and so I think it's like very tempting to like try to think about too many things and trying to get them right. And I'm kind of like, everything else can be kind of bad as long as you do like the one thing that matters.
Mat Vogels: Yeah. And the other thing too that I always see happen is that as soon as you close around and it's made public, that's actually when VCs actually come out of the woodwork and now all of a sudden they're like, Is your round still open? Could I slip in a check? as a founder, after you know, especially if it was a long, grueling process, to feel wanted for a little bit can be a huge distraction. Because now you're starting to think, ⁓ should I open up more money? Should I do that? You open the door a little bit though, and then you're kind of back in the fundraising process. But it is funny where the thing that you just spent months doing, ⁓ was really hard for some reason starts to feel easy right away after and I I'm convinced it's the universe just like trying to trick you into into pure failure.
Ellen Chisa: I don't know if it's trying to continue to failure. I actually think that's the thing about fundraising that's so funny. And when it is actually fundraising. When I was a founder, while I was fundraising, I was like, this is the worst thing ever. I hate fundraising. I never want to do this ever again. And then we would close around and the next week I like I would just be at home and I would be like, fundraising's great. And my husband would be like, This isn't true. Like you don't like it. ⁓ is going ⁓ So it's like a very special type of like, ⁓ it just finished. Now I feel great. Therefore it must have been great, even even though it's not.
Mat Vogels: Yeah. Uhhuh. Yeah. But that's what I mean is that y I think you're right, but if you have other foun or other VCs that try to pull you back into it, you forget very easily where it's just like all of a sudden you're like, ⁓ wait, yeah, ⁓ I could go back and fundraise another million or something, but then it distracts you another three months and it's never as long or short as it takes and yeah, it can be it can be stressful.
Ellen Chisa: I think you definitely shouldn't. I feel like like the way I would scope it is like if someone emails you that you do genuinely want to work with on the next one, I would cap it at no more than three to five conversations and you can do three to five conversations in the first three months after you fundraise and then not until you're fundraising.
Mat Vogels: Yeah. Any advice you give founders on the relationship and you know, investor updates or or how you think VC or founders should think about the ongoing communication relationship with with of VCs, especially at the very early stage?
Ellen Chisa: I feel like it's time is funny in startups where there'll be times where you don't really need to talk to your investors that much because you're just kind of heads down executing on something, and then there will be times where your investors are high leverage and you want to spend more time, and I think that's okay. and I would definitely think of it as you don't want your investors to feel uncertain, like where did the money go? What are they doing? What is happening? Like you need to like enough of a relationship that people have a sense of what's going on. I don't have a strong opinion on what format that takes. I think like if you d have chosen to do a round where you have a lot of angels and a lot of people you want to keep in the loop on like more public facing things, like I think those should definitely be email updates. for like elite investor that you're collaborating with all the time, I don't necessarily need an email if we're texting every day. Because like I'll kind of like have the state in the c of the company in my head as well. and I would definitely think of it more as like, okay ha if I could pick one thing a founder should do after this, it's they you should have an idea of what is actually feasible and useful for an investor to do for you and make sure they have that thing in their head. And that can be like trying to talk about your market space with other later stage investors without even mentioning your company exists, but just like queuing up like, hey, this space is kind of starting to go with its inception. it can be like, ⁓ I'm specifically looking for customers of this profile. If you run into someone with this job title or like I saw you're going to this event, can you like make connection to this person for me? But like have like tactical things that people can actually help you with. ⁓ And probably be more useful than being like, we're building things. Customers. Like just be really specific.
Mat Vogels: And you're right that it's something that you can kinda just let the VCs almost marinate a little bit so they can kinda think about it over. It's not something like I need your help hiring this person n now. Like go off and find me ahead of sales. And then it's like, ⁓ okay, well, okay. But if it's just ongoing, help me find, you know, yeah.
Ellen Chisa: Yeah yeah. You could be like, ⁓ like and maybe it's six months early, where it's like, ⁓ like after this next milestone, I think that's when we bring in a great head of sales. If you start running across people that you think are great that I should know to start like building my understanding of what great looks like in this role. Like then you've just given me something where every conversation I walk into with a great head of sales, like I'll kind of have you in the back of my head.
Mat Vogels: Agreed. are the biggest reasons? You see a lot of companies, especially at the very earliest stages. My guess is you see a lot of companies that don't even make it past to the to the next round, or they they fizzle out early. What are the biggest reasons why you see that? So that founders can again try to embed themselves in some of these common reasons why they may not make it, even just to the next round.
Ellen Chisa: I mean on it like I think very unsatisfying for founders, but like sometimes the market hypothesis is just wrong. And like that is the nature of venture capital where you're like that thing could be really big. I think Yeah, people are like, ⁓ like I had this disagreement or like we didn't build this feature in time and I'm like, I don't know, like it just wasn't there. And like I think a lot of times the answer is like it just wasn't there. ⁓
Mat Vogels: I think that happens a lot more than people think. It's just like out your control. Yeah, timing, you just didn't as cliche as it is, like the YC advice of you just didn't build something people want. ties into market, it ties into execution, it's all these different pieces. But yeah, sometimes you're right, it's a boring answer.
Ellen Chisa: Or I guess the other one is kind of what I was saying before, where it's like founders get distracted on all the things that don't matter. Is like another one. Yeah, yeah. Hiring Clang startup, managing all these people you've hired. Like you shouldn't like the first six like if you have to manage the first five people in an early stage startup team, something is wrong.
Mat Vogels: Hiring too quickly, playing startup, ⁓ All right, last bit, any advice, know, speech that you would give founders that are in the middle of the fundraising process right now, or they're just getting started, or in the thick of it. Any any final words that you'd like to say to them?
Ellen Chisa: It'll be fun after you're done.
Mat Vogels: That's so true. It hope well, but then the work kinda does begin. but yeah, it is fun. You're right, you're right. Ellen, thank you so much. Where can folks continue to follow you, continue to follow along with Bold Start? yeah, and follow both journeys there.
Ellen Chisa: It was fun. Yeah, ⁓ boldstart we're boldstar.bc. I think we're at boldstart bc everywhere. I am Ellen Cheesa pretty much everywhere on the internet. I'm very easy to find. You can also email me. I'm Ellen at boldstar.bc.
Mat Vogels: I love it. This was awesome. Thank you, thank you very much. You ⁓ you lived up to the expectation I I had of having very honest feedback, definitely no textbook feedback here, which was great. So thank you for being on.
Ellen Chisa: Anytime. for having me.