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AJ Smith | Outlander VC

48m 45s

AJ Smith | Outlander VC

In this podcast episode, AJ Smith, investing partner at Outlander VC, discusses the fundraising process. Outlander is a generalist pre-seed fund that writes large checks ($1.5M–$2.5M) for startups solving hard technical problems in deep tech areas like AI, defense, and energy. Smith shares his unique background: building defense tech at 16, a career in music (violin and songwriting), early crypto engineering, and founding startups. He sees storytelling as key—taking complex ideas and making them memorable. His favorite part of VC is working with brilliant founders daily; his least favorite is rejecting founders after deep engagement. He advises founders to pick Outlander for its track record, follow-on support, and commitment to founders who persist. For fundraising, founders should build strategic lists (using resources like VCC), be ready for rejection (pitching up to 150 VCs), and leverage their network for warm intros, though cold submissions are still accepted. Pitch decks must be concise—readable in 90 seconds by headlines—with the team slide most important. Smith values real builder experience (e.g., GitHub, project portfolios) over corporate logos, especially for young founders. Overall, he emphasizes authentic connections, persistence, and clear storytelling to succeed.

Transcription

10063 Words, 53421 Characters

English
[Music] Hey everybody, welcome to another episode of fun raising a podcast where we interview top early stage investors and ask them all the questions that you want to know about the fundraising process. And today I have a very special guest, AJ Smith investing partner at Outlander VC. We talked a little bit before. I'm expecting a little bit of spice and authenticity to this one and I think that you are going to deliver on that because that's what the founders are here for. But before we jump into the fundraising process, AJ, can you give a quick background on Outlander VC specifically what you're investing in, average check size and maybe the stages that you invest in? Yeah, 100%. So I mean, first of all, we are a generalist fund so we will basically look at everything. There are a couple areas we don't touch. My personal focus is a lot in deep tech. So, AI robotics, autonomy, defense, aerospace, advanced manufacturing, looking a lot of energy, industrial infrastructure. So, you know, basically, companies solving really hard technical problems in big, consequential markets. But generally, I mean, I'm just as likely, I tell founders to do an awesome, vertical AIDL where I believe that there's a big data defensibility advantage as I am to do something in the future of manufacturing. At the end of the day, for us, we invest at pre-sedancy big checks really early. We are a true pre-seed lead. And so that means that I might write a million and a half into an idea for the right founding team. And so when I say the right founding team, for us at Outlander, we dig in hard with our founders. We build a relationship with them. We actually have, you know, a 20 point founder framework that we are assessing our founders across in order to figure out, hey, is this a fit? Are you an Outlander founder? And, you know, at the end of that process, you know, that can end up with a million and a half to really fork to two and a half are the, you know, the check size ranges 10 to 20%. You know, again, back to being a true lead at pre-seed. But yeah, that's kind of who we are. I love it. Thank you for that. I think that the ability to be flexible across those things is a superpower that I think a lot of funds have the ability to invest in a lot of things at different check sizes and ranges is a huge value ad that founders will appreciate as well. All right, let's go a little bit into more on your background. These are questions that founders wanted to know about the VCs that we talk with. The first being, why did you choose to get into to VC? Maybe it's a little bit of context. I find that VCs have a vast, you know, variety of backgrounds, but they're almost always really exceptional people that could do almost anything. Why did you get into VC? And then what were you doing before? Yeah, 100%. So I mean, first of all, I got into VC and specifically with Outlander. I was investing in startups before this as well through it through different fun. But I specifically joined Outlander in part because I was looking at, hey, where can I invest and write big checks really early and learn how to be one of the best adventure? You know, page founder, the fund, Laura, the rest of the team here. I mean, our team has 18 unicorns out of about 150, 160 investments. And so when you're looking at, you know, a hit rate that high, to me, at that signal, hey, if I want to be the best, I need to go work with the best. The people that are experts in identifying founder talent this early. And we're such an accessible fund that that was the draw to me. And then backing up, I'll go way, way back. I was building defense tech at 16 years old at the Naval Research Lab. I was selling computer games for the TI-83 and everything like that. So all my friends and like, you know, games to not pay attention in math class because I wasn't paying attention in math class. I finished all my math stuff super early. So I was going out to the Naval Research Lab building, you know, like infrared sensors and writing all the like nighttime correction, object detection stuff. Slimaltaniously, parallel path. This is, I don't know if there's going to be a first on this or not. But I also had a pretty interesting career in the music industry. So I was a young associate to the National Symphony on violin. But let's go. Yeah, I was a young associate with the National Symphony on violin, which a lot of people think is weird. The whole like comp-sci engineering meets music. To me, it's very similar. I'll get into that in a bit. But that always gave me a bit of an entrepreneurship mindset because, you know, gigging, playing around, playing shows, writing songs. Fast forward, I went to NYU. I got my first exposure to startups and, you know, joined a, I was an early engineer at crypto company in 2012. Super, super awesome. Wild time. It was insane. Our CEO got arrested at the airport. And it was that era. And my buddy there turned to me and goes, "Hey, do you want to be my technical co-founder?" And I was like, "Yeah, that sounds amazing." Now, parallel path, I was also now starting to do some cool stuff in the music industry. I was getting it open for the Eagles. I was getting to, you know, open for Lindsey Sterling on violin. Yeah, Glenn Shrive was my mentor over there, Reston Peece. And actually, he would tell me songwriting is basically taking big ideas and putting them into small spaces, right? And so how I've translated that over the years is, "Okay, your job as a songwriter or storyteller is to take some of the biggest abstract most emotional concepts in the universe." And then boil that down to a three and a half minute song that gets stuck at your head in the shower, right? That's not what I tell my founders. And when I'm getting ready to take them out to go raise, it's like, "Okay, so here's our job. I want you to take some of the biggest most complex engineering ideas in the universe." And let's get a stuck in everybody's heads in the shower. So at the end of the day, life is storytelling. There's a whole other, you know, episode we could do on that. But to fast forward, music career was really cool. I got to write, you know, a bunch of charting songs and do some cool stuff there. I never wanted to be a starving musician. There were definitely times when I was very starving and sleeping in the car during that journey when I was coding. And that sort of dual skill set enabled me to have a really cool, just two-path career that to me merges really well in venture. I'd been down the founder road that requires a lot of creativity. I had been down the music road that requires a lot of creativity. Your small business owner as well there. And ultimately, like seven years ago, I started investing in startups. And that's where I got to see the perfect, you know, melding of my worlds. And it's been awesome. And I've been loving it ever since. This is one of the more common ones we had founders asking us was, what is your favorite part about the job and being a VC? And then what is your least favorite part about the job? Oh, well, so my favorite part hands down. I get to talk with brilliant people who are sharing the best ideas that they've ever had with me every single day. And, you know, so many are just on the cutting edge of what's possible. And I'm getting to help see around the corner of possibility and then help enable that, which is just amazing. Like I feel like I'm getting to like let's go back in time. It's as if I'm getting to work with Thomas Edison every single day. It's awesome. My least favorite part of the job is honestly, you know, I talk with thousands of founders a year. No, we had Outlander. We're reviewing. We're actually in our top of funnel that we bring in not even counting the rest of the universe of startups that we look at. That we don't end up taking, you know, a first real pass at. But, you know, we review it over 5,000 deals a year from those. We're doing 15 deals. And so my least favorite part, I would say after the first conversation, it's pretty easy to just go, Hey, you know what, it's not a fit. And like I wish you the best of luck genuinely because I do. Like you have the balls to go out there and go and like build something that you believe in. That's freaking awesome. A lot of people in life never have the gumption to do that, right? But my least favorite part is when we've gone deep with a founder. And I have to say, you know, we just couldn't get there. And a lot of times because our process, again, going back to, you know, our founder framework, it's very different. I'm having very deep intentional conversations with founders asking questions. They've probably never been asked before, which is an amazing experience for them and for us. But it's hard when you built that close of relationships throughout, you know, maybe 10, 15 hours together. And then when you have to say, Hey, it's still not a fit for us. We're not the best investor for you here. That can suck. Yeah. Yeah. And we'll dive into that later in the process too on what are the reasons that VCs are typically saying no or passing that late. But it is hard. And like you mentioned, it's the vast majority of the time too, which is also unfortunate about why we choose to do this. All right, last question here before we dive into the fundraising process, why should founders pick you and or outlander to be on their cap table? Yeah. Well, first of all, I'm picking outlander just because we have an incredible trap record of helping build multi billion dollar companies from nothing. All right. So like we've been there. We've seen every possible iteration of drama almost just about. And if it's something new, like we're ready to get into the arena with you and figure it out together. I think the other reason to just choose outlander as a whole, you know, we were now not just, you know, one check one time. Like we do follow on and we have, you know, an opportunity fund actually specifically for for coming in down the road as well. And the thing that I want founders to take away from that, because I know that there's others that do follow on investing in all that our entire, you know, method here is if you haven't given up and you haven't shown us that, you know, something blaringly awful, then we will not give up on you because we, again, this goes back to why we pick our founders and the type of outlander founders that we back. If we still believe in you as a human being to lead this business, then we're going to continue to support you financially and with everything else too. I love that. It's always good to have someone in your corner that can continue with you across the entire journey. So that's a, that's really nice. All right. Here we go into the fundraising process itself. We're going to break it off into three different parts. The first is how can founders, a lot of folks listening to this don't have a background in startups. They don't have a network How can they actually get in front of the right VC? How can they get in front of you and Outlander? So that's step one, step two, they've done that. They've gotten in front of you. They've scheduled the meeting. We have a whole section around just impressing you enough during that first initial meeting to keep the conversation going. Third phase is you've lined up a bunch of those initial meetings. You're now into the meat of the process. You're hurting cats. You're trying to push this across the finish line. We'll give some feedback to founders on how they can actually close out their rounds. And then last little bit, we'll do a couple questions on some of the mistakes that you've seen founders make after fundraise, post-frontarise. We'll set some expectations there. So let's dive in with the first one. For founders that are just getting started, they have an idea, they have a pitch deck. What are some of the feedback you would give to founders on how they build up that first initial list of investors, the funds, the names, the sizes, what characteristics should they be looking for before they'd even started the outreach process? - Some of it is pretty easy. You go to VCC, right? And then you filter, (laughs) plug, product placement, endorsement, right? So there's plenty of resources online in order to go and find lists of funds. The tricky part is being strategic about who you're actually going to try to get in touch with. Because not everybody is going to be a fit for your business. And when you just send out blasts, I mean, sure, there's a method to that, but a lot of those, that's just, if something feels too blasty to me, I may be send it to my 10 minute call or it just doesn't end up getting read, right? And so I think that's, that's just kind of generally step number one, get organized and get strategic about who you're going to reach out to. Step number two, be okay with hearing, no, a lot. I think rejection therapy is a big one. If you're going to be a founder of a company, you need to be prepared to pitch 150 VCs to get to your first check. And if you are not prepared for that, you probably shouldn't be a founder. And this, because this is going to, you're going to get knows all the time do you believe in your business? Now, at the same time, be receptive to feedback, react to it, but like hold your ground on the things that you actually have conviction in. That's, that's going to go a long way. Step number three, how do you actually get, and let's say you now whittle that list of, you know, thousands of VCs down to the 150 that you're going to go and reach out to in this first wave. How do you, how do you get there? Now, some of them, we, you can just go outlander.vc, you can submit and we are highly accessible. High bar, obviously, just from 15 deals out of 5,000, but we are highly accessible. We believe that the best ideas can come from anybody I am. And so we want to be able to talk to those founders, but not everybody's that way. And I will say, when something comes to me through my network, whether it's one of my founders, whether it's another VC that I do a lot of deals with, I do look at it more seriously, and you're more likely to get a 30 minute intro call versus a 10 minute intro call, right? But at the same time, what we really tried ourselves on is, if we're doing it, if we actually take that 10 minute intro call with you, you are getting our full undivided attention for the, for those 10 minutes. And you are just as likely to have a deal get done as somebody who gets, you know, an hour because they met us live at a conference and like 400 us on how I'll get something like that. Though don't follow somebody around at a conference forever. That's definitely the wrong thing. That's a not do. Yeah. And so I think one of the best ways that founders can actually build authentic connections with VCs, ask your founder friends. Ask your founder friends that are out there a few steps ahead of you, you know, go and try to figure, and part of that to be because through customer discovery, you might be talking with potential startups who might be customers and viewers. And that's such a great way to then go and get somebody to believe in champion and you, and then turn that into, hey, look, I'm actually getting ready to go kick off my 3C. Do you have anybody that you could introduce me to? And if they really like you and they believe in what you're doing, they will open up the phone book. So that's, I think that's a big underutilized tool at times is just actually asking your founder friends for interest. Yep. But I love that from your perspective, and this is important, I think for a lot of founders as well, is that even if they don't have that connection, they should they try to get one, but if they don't, I love it when, when fun say that they still take submissions, colds, they review them. It's one of the hardest parts of the job that we have to go through so many submissions. But all the best VCs I know do that. And it sounds like you guys do too, which is awesome. Yeah, there's a lot to do from those. By the way, even if you are going and you're pitching somebody who's not going to be able to be a lead, asking the people who are down to commit, get that, get in trust from them. It really only takes one person to start to believe in you, to start to open up your network massively. Absolutely. Yeah, and then just continue to build that momentum. One of the best ways I found is taking the step back, it's almost pre-fund raised stuff. Before you've actually sent the emails, that's what a lot of the work happens. A big piece of that is going to be with their pitch deck. You mentioned, you know, 5,000 founders reaching out throughout the year, that means you're going to be reading a lot of pitch decks. Is there a slide or multiple slides that you look at or gravitate towards as being maybe the most important slides in a pitch deck? I think you could probably guess that my answer here is going to be the team slide. That's where I'm going to go and actually, you know, collect the people's LinkedIn's and stuff and spend the most time. That said, I think my biggest pet peeve with pitch decks is when there's just too much going on. Because realistically, I'm only going to spend 90 seconds, maybe if that sometimes looking through a pitch deck to decide, hey, is this worth a meeting or not? And so one thing that I tell founders, and I know everybody has a different style, but for me, if you're a pitch deck, I can't read it headline to headline and quickly understand exactly what your business does and why it's important and why it's consequential, then you should probably take another stab at it. You know, I don't need all the detail in the world. Even honestly, even on like a quantum computing or like other kind of deep tech company, I should be able to understand over the course of 10 to 15 slides, but reading headline to headline, why your company needs to exist and why you guys are the team to do it. - I love that. I haven't heard that feedback before. That is a good one. If I just read the headlines on each of your slides, that should be enough to get me to move on to that next step. That's really good advice. - Problem is the biggest text on your screen. We have a problem. - Yeah, I love that. - It should just be what the actual freaking problem is. - Yep, exactly. You mentioned Team Slide being the most important. What makes a really good Team Slide, then? In your case. - Yeah, I think understanding, and this maybe even goes back to the headline thing. Not to cut out, but you know, why what is your statement as why you guys are the right team? Now, look, I invest in a lot of college founders that haven't really had much work experience. Even then, still understanding why are you guys the right team to do this is critical. I think obviously logos are a helpful visual tool there that can be great. I don't care as much about logos as much as I do about the impact, lifelong builder, but maybe show, I love one hardware founders actually link me to a portfolio of projects that they built since they were again. That's awesome to see. I love when people link to their GitHub. I love when people take advantage of that space to sell why you are the right founders for this company. And the answer is I hate to do that, but it depends on the founder, right? Of course. And I love that you mentioned, we're seeing a lot of this too with a lot of young folks in college is they don't have the lot of the work experience, but they are loading up on all kinds of like, they're building robots in their dorm rooms, that they're building websites and like actually building stuff just for the sake of it and linking to those things. The end of the day, sometimes those are, if not more valuable to us as VCs, as you know, experience 10 years experience at LinkedIn or something like that. Yeah, show me the photo when you were, you know, 16 building your first 3D printer or something like that. And like your robots from your robot club competitions, whatever it is, you know, I'm definitely always, I want to see that stuff. Yep, agreed. Any last bit of feedback or advice you give to founders during the pre-meeting phase? So everything leading up to the initial meeting. Don't send me long ass emails. Keep it short. Yeah, keep it, keep it concise. And honestly that having, I think people spend too much time on pitch decks. It's, you can get decent branding together in a decent vision of what this should look like. But now with all the tools that are out there, it's more about that story. So get it done, get it out there and let's talk. We recently did a review of a lot of the pitch decks that we, from the founders we've invested in. And one common trend was that they were some of the simplest pitch decks of all the other ones that went through. It had lined, it had lined to your point. But even just what they're trying to tell us, they're shorter, they're simpler. And these are complicated startups. We both invested in deep tech as you mentioned. These are really complicated startups. Yet they somehow figured out a way to make their pitch decks, 10 slides, super easy to understand. And that's important. And yeah, I did something that I'm sure you guys feel the same way. But as soon as something comes into my inbox, I am assessing every single thing and part of that. That tells me this is somebody who can take a big idea and bring it down into a small space. And that's going to be a valuable skill when you're fundraising, when you're selling across the entire lifecycle of a company. - Nope, agreed. All right, well, let's say they've done some of these things right. They didn't follow you around a conference. They didn't send you a long-ass email. They got your attention. You're now going into a meeting with this founder. What are you looking for as a VC, but then also as you, AJ? What are you? looking for that initial meeting with the founder. Clarity of vision. I think that's a big one. Uniceness of the insight. There's a lot of people that maybe have identified a problem. They think they're the only one. Have you actually done good startup competitive analysis, not just major company competitive analysis, but startup competitive analysis? I will invest in technical founders who are bad at pitching. I will. If it's again going back to all the other traits that I'm looking for, it have no problems with that. I don't care if you've never pitched a BC before. I'm happy to be the first one that you pitch on. I'll be gentle. But I think an authenticity is really important. If somebody's trying to sell me too hard, that's the nuance of clarity of vision, but not overselling where as soon as I start asking questions, it all falls apart. Yeah. I remember I see they used to say partners, you say that when a good problem is being solved, it's obvious and it may not be obvious at first, but as soon as the founder starts talking about it, it's obvious. And part of that's picking the right idea and all those in there. But if you have an obvious problem and solution, then you don't need to oversell it in many ways. Yeah. 110%. What are some of the mistakes you see founders make on these initial calls? Obviously the opposite of what you just said, you know, being too long winded or anything there, but everything from maybe the way they prepare their pitch decks to who they invite to the call or anything like that. What are some of the mistakes that founders can avoid on those first calls? On a first call, I don't need to see the entire team. That's that's a big one, especially if it's a 10 or 30 minute call, should be the CEO realistically, it should just be the CEO. That's your job as a CEO co-founder of this business. The other saying, what if if there's a connection here, if we need to dig in deeper into the tech and you haven't learned enough about it to be able to explain it, well, that's another conversation, but we can always have a conversation with the CTO next, but CEO should be out there. The other thing is telling me that you're running a tight two week process. That's. Hey, it's probably not true. I think a lot of founders are and I see and a lot of other places do a good job of teaching the founders how to create urgency around their rounds. But this goes back to the way that we're going to do deals is very relationship driven. If you want somebody to be rolling up their sleeves with you for the next decade, you shouldn't want to rush that either because it's also time for you to assess, is this the right investor for me? Yep. It definitely goes both ways. You hit it on it. It's a 10 year relationship. It's unfortunate. Honestly, that so many deals do get done so quickly on both sides because it ends up being one of the more important relationships that you might have in your life, which is saying something and there's usually not enough time to truly validate it. But this initial meeting can say a lot. So it kind of leads to do another question. It does go both ways. One of the questions that founders were asking was what questions should they ask of the V season, these initial meetings? Should they ask any questions? Is that considered, you know, arrogant or where's that line drawn? But what are some of the questions that they should be asking to take control of the process themselves? I mean, I definitely think it always speaks well when a founder can command meetings and the flow of them that said, you know, if I'm telling you, I don't need to, I don't want to walk through a pitch deck and you insist and you pull up a pitch deck and share your screen. I'm likely going to pass unless you really blow my mind. You know, I do, I do appreciate what a founder can say, hey, I'm going to, you know, own this process here because that tells me that that somebody who can probably take command in a lot of different situations. We will play with that. At the same time, I do think that there is a way to not come across as to your point, like too arrogant, right? I think at the end of the day, this is a relationship, right? Back to the whole 10 year comment like this is going to be something where we are going to explore things together. Hopefully we're going to be incredibly helpful to you. And so we should again, take the time to get to know each other. As part of that, though, make sure that you do always ask questions that are unanswered around process, timeline, check size, just some of the basic things that you should know, ownership targets. So then that way, as you are getting into final rounds and you can understand where you are in your process with the multiple different investors that you're talking to, is that 150 list gets down to 50, gets down to 25, gets down to 10, gets down to five different ICs for potential leads. You know, it is important that you know all of that information so that you know what you're getting into. Yeah. And usually VCs, I mean, we're happy to answer those and they're usually really quick answers. So we don't we can easily just give you that context and then move forward. Any other sacred vice? Yeah. Yeah. You know, asking to talk to founders in the portfolio is fine when you move to diligent stages. But I think we're not going to go and distract our founders super early in the process. I mean, if you meet one of my founders out in public, I'm sure that they'll tell you great things about us, but asking them to take time away from building their businesses for 2,500 deals a year, we're not going to do that. No, I definitely don't ask for it in the initial meeting like to your point. If you already know one of the founders, maybe that's how you got the introduction, totally fine. But yeah, you can on that first meeting, expect us to because that's a currency for VCs too. We care very deeply about our founders and we're not going to waste their time as well. Maybe the last bit on this part is the next stage is usually getting multiple meetings. You have to meet with other team members on both sides. But where do you land on scheduling the next meeting? Does the meeting usually just end and it goes to text or email, but maybe right after that initial meeting, how can founders prepare for potential next steps? Yeah. I mean, I think that's as simple as asking a question around, hey, and what are your thoughts on next steps here or what are next steps? Right. What are next steps for I comes off more confident and I might tell you that I need to marinate on it for a second because I genuinely might, especially in deep tech, I need to go and do some research myself, probably educate myself, claim verify. And so I might need 2448 before I'm saying, okay, 100% less, let's jump in. There are times at the end of calls when it's obvious, everything's clicking when I just go, yeah, let's book our next conversation. I will say investors should probably be chasing you if there's a real love match. And if that's not happening, I think it's still really beyond top of your follow up game. That is something that we also assess. Do you follow up promptly? Do you respond to emails quickly? All of that. But yeah, I'd say just asking what are next steps? What can we expect from here? We'll let you know if we're passing or. So let's say that we're now into that next phase. Could you give a little background on maybe what that process does look like for for the fund and how you go from that initial meeting to them carrying the multiple meetings, diligence and all that? Yeah. So I mean, the way that we structure our process, we have like a lead intro call, then we'll go to what we call a vetting call, which is now we're spending 45 to an hour and we're meeting ideally all the people who haven't really meaningful chunk of equity. So the co-founders of the business, right? Tech leads if the tech leads got. We bought and invested in a company that doesn't have a tech lead, but over 10%. But you know, like we're meeting. Yeah, especially in this era, which I know maybe a lot are thinking, do you need to, especially in that software AI for enterprise kind of side, right now we're holding pretty firm with that. That there's amazing creators that are able to go and use no code load code tools in order to build great marketplaces and all kinds of things. That's just not the profile of a founder co-founder team that we are investing and that we are backing. We really need technical builders on the team with a meaningful chunk of equity so that they're going to stick around and help people die. So now let's say in the vetting call, we're meeting everybody, getting a quick pulse check around the room, like getting to again, meet the whole team. We'll then decide who from the team we feel that we need to spend the most time with to really get to know as part of our process. Often it is about equity and or just meaningful contributions to the tech and defensibility of the product down the road. And so then from there, I mean, we'll spend another 10, 15 plus hours just really digging in deep on somebody's life and the decisions that they made will share about our own. So then that way we can end up really feeling like back to the analogy from before, like, okay, we're going to get married at the end of this. We should at least spend as much time together as they do on the bachelor, right? Let's try to make that happen because I'm going to be your biggest advocate when, especially if I'm sitting on your board, right? And when that board gets bigger and it has people who are, you know, I love all the amazing growth investors in my network, but they care about different things than I do. And so then when maybe the business is not doing so well on certain metrics that they care about, I can be that voice in the room that says, no, this founder is amazing. They are a badass. They are not going to give up. They will figure it out. I've seen everything that they've gone through. And I can, even if I'm just an observer at that point, I can still be a voice in the room to hopefully, you know, calm waters when things are getting frothy. Yeah, it goes back to, you know, what you said earlier in picking the right partner that's going to have your back is so critical, especially as you continue to grow your company as well. What are some of the ways that you would encourage founders to build FOMO and momentum and some of these things, but do it in a way that doesn't feel, you know, fake or disrespectful or how would you tell founders to handle this process? Because it is really hard. It's a difficult balance. Yeah, I think there's a combination of honesty with slight exaggeration is okay, completely over exaggerating not okay because it's a small world, we all know each other for the most part or we know somebody who knows each other. For sure. I think if you're on first and second calls with multiple potential leads, say so. I'm on first and second calls with multiple potential leads and things seem to be resonating. So I'm just trying to understand what your guys' process looks like and timeline as I'm starting to put together what this process is going to look like. And great, okay. You're creating a little bit of FOMO because I'm like, all right, well, they're talking, I'm not the only person that they're talking to. And then when you're on second, third, starting to move towards diligence calls, you can say, yeah, I'm now on second, third and I'm now moving towards final diligence. I've got a couple I see that are scheduled in the next couple of weeks. Say so. And we will have some urgency around that. I think trying to create fake urgency, it's an interesting strategy. You could just straight up lie, but it usually will come out and that could be a reason to kill a deal because at the end of the day, I'm not going to do a deal with somebody who's dishonest with me. I don't mind somebody who can add an extra 15% of color to something because I think you need to be able to do that as a storyteller, as a founder. But if you fully misrepresent something to me, then we won't be able to work together. I can't tell you how many deals we see where we're really excited about it and then ultimately, it's just like, like, Janka, like one piece falls and then the whole thing crumbles down because of one exaggeration. One thing I have said though on this podcast and I see this happen, not a lot, but enough to be to be weary of as a founder is VCs will also add a little bit of color sometimes to maintain their run in the race. So I've heard sometimes where a fund will say, hey, we're really excited about this. I think we're going to move forward and we're going to let you know on Friday what our terms might be. And here's that, especially if it's their first time going through this and they kind of go, oh my gosh, they're going to write, you know, the term sheets coming on Friday. They then take that to another VC and it's like, we're getting a term sheet from this fund on Friday. And it's just a miss. It's a phone, your telephone game that's just missing interpretation across the board. But then I hear that. I then reach out to that fund and like, oh, no, no, no, we actually think we might be passing and we're going to let them know that on Friday. And then now I'm like, oh, wait. So where's the disconnect? Who's lying here? So again, it's not always black and white. There's some gray area, but it's almost just as important as the founder to get the clarity and truth from the VC as well. So if they do say something like that, double check and make sure it is what they're saying. Yeah. No, that's great advice. Because I mean, I know that I've been guilty of it at times of maybe being unclear. And I'm not trying to be. But I think there's the, we hear what we want to hear sometimes. Yes. Of course, especially in this process and especially if it's your first time doing it. VC, we want to be excited too. And we are the other thing. Maybe you could shed some light on it's not just on typically. It's not just on the one VC that's making the decision. You do need to take it to a committee or a group of folks. What does that look like? Maybe internally with with your fund without landed, but maybe broadly as founders are thinking about what that means. What is it? What does it look like from a decision making process typically in a VC fund? Yeah. So every fund operates slightly differently, but it's usually similar things where you might have IC, right? And that could be an internal IC where a founder is not invited to at all. And the partner who's leading that deal goes and presents everything to the rest of the investment committee and they decide and then is the deal moving forward or not. They might have a majority rules. They might have anybody can do their own deals. But they still need at least a certain of they need a managing partner to sign off on it. Every fund operates a little bit differently. There's also the public IC, which is when the founder comes in and they are supposed to present to the team. And that could be 45 minutes to two hours, whatever it might be. And that is usually that's more what we do. We've done a couple of different iterations of it where sometimes we've done partial team and this depends on pace of the deal or just availability of the team, where sometimes we'll make sure that we have at least three partners usually in order to be on these. So in that way, you have multiple touch points. Multiple people can be asking questions and then we can get you an answer pretty quickly after that if we're moving forward or not. Or if we after that, I see maybe some things were revealed that aren't necessarily a reason to not do the deal, but an area where we realize that we need to dig a little bit more in order to stay as excited as we have been feeling. And then sometimes we'll also do, and we're actually experimenting with bringing it back to doing the full investment team in part because what we were doing for a minute was you present to the, it allowed us to move faster, but like you present to the smaller group of partners. And then you get a decision pretty much that same day or and then you would get to meet the entire rest of the partnership maybe a couple weeks later when schedules align. Yeah. But what we found is that then that means that the rest of the partnership, while they've read the deal memo and they've heard us all talk about it, they haven't had that experience that with the founder. And I think getting that experience and getting to meet everybody on the team and then when we show up wherever you live and we're hosting an event and you've already met everybody, I just think that it's a more positive experience. And sometimes we do in person, sometimes we do on Zoom, it really depends. But now we've moved back to doing group ICs wherever possible. I like that. I think we're seeing that trend with a lot of funds as well, which I think is great. I think it's scattered a little bit, especially during COVID. And you saw a lot of those decisions being made and kind of funnels. But yeah, definitely more team, broad team these days. This is actually one of the more recent questions that we had a lot of founders asking about. Now that these episodes come out, you're going to be the first one to answer it. One of the things was founders get really frustrated when they find that VCs are waiting for a lead or very desperately wanting to know who else is already involved. Can you just shed a little bit of light on why that is important from a VCs standpoint, especially if you're a fund that does not lead? So that actually brings up an interesting question that founders can ask at the beginning of their process and that original FAQs. Do you guys lead rounds? Do you co lead? Do you follow? Do you need a lead? So in order to do this, just so that I can understand, it's like, look to put this round together. And by all means, no matter what they say, if you like them, you should probably still continue that process all the way through because it can be attractive to a potential lead. If I see, okay, you guys are raising a $4 million round. You've got $5 million in commits, but you still just don't have a lead figured out yet. Now there's a couple things where I might go, well, okay, how many leads have you talked to? Why are they all saying no? I don't know that kind of stuff. Even if I know, okay, you've got two and a half committed and you've got one and a half open, you're looking for a lead. And then I might go, well, I got a right to with that, actually, so you might have to squash some people down whatever the case. That's part of the answer. Okay. The other part of the answer here is when you're frustrated with that, then start asking these people, hey, do you have any leads that you can introduce me to? I'm talking with Seppel right now. I'm early in the process. And I want to be able to help you guys get to as much conviction as possible on this. If you have anybody in your network, please introduce me. They may or may not. Sometimes when people say that, they are just reserving the option to say no or reserving the option to say yes, I hate to say it. It's the same thing as when people pass for something being too early. That can be true if they're fun like never invest in pre-seed and you pitched a series a fun and they just go, it's too early for me. That's probably true. But if they do invest in pre-seed deals often or a seed deal and you're a seed stage founder and they say that it's too early, it probably just means you are too early for us, which means you still have some shit to figure out as a founder, you have some growing to do. And we are not excited enough to do this, but we don't want to piss you off because in the event that you do figure all this stuff out, we still want to be able to profit. Exactly. Of your genius, right? And look, I get it. I tell founders not all the time. I mostly just tell founders, hey, this isn't seeming like it's going to be a fit right now, but like, let's please stay in touch. I genuinely mean that because I could be completely wrong about how quickly this is going to go from zero to one, right? But if all the sudden momentum starts to change, I will come back in and actually have a conversation with founder. I say, I need to get your investor updates. I will follow along. Now, back to the urgency in terms of like getting leads to commit. Part of this goes back to when you're making that 150 list at the very top of your process, there's good resources out there in order to see who's been leading roles. Do the research, be strategic and find a way to actually make sure that 50% of the people that you're talking to are actually lead investors. Yep, that's excellent advice. What are some of the main reasons that either you see other VC funds pass or that outlander passes? What are some of those big reasons? And I think that maybe is some context on here. A lot of founders assume they take it personal, all these things, but a lot of times there's a lot of other reasons that VCs are making these decisions. Could you send some light on those? Yeah, I think first thing to remember is that VCs for us is pretty much power law. So we're going to be wrong a lot. And so don't take it personally. This is, you're talking to somebody who has an opinion about a market or the tech or you that may or may not be wrong. They probably don't know you well enough to make a judgment on you. They are making a judgment for the most part, most likely on market and how do I just see this person in this quick gut reaction as a leader who can go after this maybe big market and maybe it's a smaller market than I would like to play in. And they're doing the math and they're just thinking the way that this was presented right now, I don't know if this founder can get here. And they could be wrong. So don't take it personally. That goes back to the build up the tough skin to be able to hear knows a bunch, right? I think some of the other reasons that people pass early is just, are you moving fast enough? Are you executing fast enough? That's one that I want to say. to understand the true timeline of a business. And again, don't lie. Like don't try to make it sound like you're moving faster than you are. I think honesty is key. But if I've gone through your timeline with you and I've seen, you know, they dragged their feet a lot. They still, it's been two years and they still don't have an MVP. And this is like an AI app layer thing. And I've asked why and the why's don't make sense to me. To me, that makes me question, do you have the right people on your team here? Or do you just overthink or do you not, or do you not move fast enough? And I think especially in this era, that's really critically important. So as your to founders, as you're building your team and as you're thinking about your own bias to action, be action oriented and bring people into your team who are absolutely going to move shit forward. That's another big reason. The other reasons that we pass it out, Landr, those are all there. Vision, how unique is your insight? That's a big one. If I don't think that the insight that you have is as unique as I would like it to be, we're probably going to pass. If your execution has been slower than we would like, we're probably going to pass. And this happens a little bit later. If there are any kind of character things that come out for us, whether it's dishonesty or we just at the end of the day, like the number one thing that any of us have to underwrite is that you are not going to give up when things get hard. That also might, you have to then take into account like are they going to have the flexibility and the, you know, have the insight to be able to pivot if they need to pivot. But ultimately, like, I'm trying to understand, are you going to give up when things get hard because things will get hard at some point? Even if it's easy right now and you've got a bunch of investors giving you turn sheets, things will get hard. And if I don't believe that you are going to stick through this rather than jump to attractive offers that start coming in once you get to seed series A, series B. And things get hard. Not going to do that. No, that's excellent. That was really good advice. Let's say that they've done all of this. They close out their round. It feels like it's celebration. Like you mentioned, though, things do get harder. It seems like they get easier in some ways, harder in other ways. But what are some of the things that founders or the mistakes they make right after they close their round? Because it feels like everything is going in their direction. But we see a lot of times, this is almost the easiest place to start making, like, jeopardizing company level mistakes. What are some of those big ones that you see? I'd be curious how you guys think about this, but I think distractions can be a big one. Because now all the sudden, maybe for the first time in your life, you've seen $2 million. And you're thinking, oh, shit, I could conquer the world. I could do anything. And we love that mentality. That's you need to have a healthy level of delusion to become a founder. But if all of a sudden you're starting to think that you can do everything, you can't. And I think lacking focus in the early, early days is a really important, you know, that can be something that can kill a business. Because then you're not actually moving towards that North Star. The other thing is we do our best to try to understand who, who all do you have alongside with you? Who all are you going to hire? And are they excellent? But if you're not honest with us and you're not honest with yourself, you might miss things that are not going well. And I think going back to the overselling and overhyping, if you don't come to us when there's a problem, and maybe that might mean that your co-founder or one of your early hires or somebody is starting to get toxic or that there's something that there's a serious problem. And you've hired it for six months or a year. That compounds daily. As soon as something, and look, we've helped co-founders navigate co-founder breakups. We've helped co-founders navigate co-founder counseling and then be better than ever. We've helped people deal with, you know, having to fire people who were along for the very beginning of the journey. And then all the sudden started getting weird. All kinds of product can start not working. Like there's, there's all kinds of things that can go sideways. But if you don't let us know when things are going sideways, don't give us the rose-colored glasses. That's for you to go and sell to your customers and your outside world and your grandma. I want the truth. Because otherwise, you know, five of the seven of us on the outlander team have been founders. Like we've probably been in a similar situation and we can help you. So let us help you. Yeah. By far, the most common answer that we get is that you either sometimes you go radio silent, which isn't always the case, but there's radio silence completely. There's also radio silence where it feels like, oh, the last six updates in a row, they've been like crushing it. No issue. Everything's great. And that's usually when nobody's always crushing it. Yeah. No, no, definitely not. As you continue to like push down that line, though, you've seen a lot of companies to your point, they've reached multi-billion dollar valuations. But then we see a lot of companies that don't make it all the way through it all. In fact, the vast majority of companies don't make it. What are some of the big reasons long term, in addition to maybe some of the ones you just mentioned on why companies fail so that founders can start thinking about that early? Yeah. Failing to align incentives, I think it could be a big one. And that's either what's your team, what's your investors as founders, making sure that you just have everybody marching towards the same mission. Taking your eye off the ball too early is a big one. Yeah, taking your foot off the gas, being a founder is not for the faint of heart. And just because now you've raised 25 mil, 50 mil, 100 mil, that's not the time to get complacent, especially in 2026. I think if anything, that's the time to say, okay, well, what we've been doing is working, but we need to keep freaking going. And I think too many people start gliding too early. The other thing is, it's hard as your team gets bigger to maintain you know, culture and intention with every hire. But the better that you are as a leader, and sometimes I think, you know, CEOs, on one hand, there aren't just the natural people who are amazing leaders that know how to do this and they're one in a billion, right? But the, there's often a need to upskill. And again, that's going back to your board, back to your investors, back to your community. Hiring a coach, if you have to, because you're struggling with team morale, continuously learning, learning how to level up yourself as a leader so that you can get the most out of your people. And make sure that you're hiring amazing people who are going to perform well and grow as leaders. You don't want people, if your team, flat toes too much, your business is going to plateau. Yep, you'll lose. AJ, this was awesome. Any last bit of advice, feedback, motivation that you'd give to founders that are just going into the fundraising process right now? Yeah. Yeah, this is one of the most amazing times I think in human history to be building right now. And I think that there's so many, especially in deep tech, which I know we didn't talk about a ton in this, but because that is an area that we don't, we're both really focused on. And I'm sure that there are a lot of the listeners here, our deep tech founders, the cost curves are coming down, innovation is getting faster. And yet the physical world gives such an opportunity for unique data sets and for unique defensibility. And if you can actually figure stuff out in the real world, there's there's the sky is the limit, right? So this is a just an incredible time to build. And I have so much respect for everybody who's out there doing it right now. And so a, have faith in yourself. If you really have conviction in your idea, you know, go after it with, you know, as hard as you can, because there's been no better time to build. I don't think in human history. And then be just get, get used to people saying no and carrying on, you know, go ask for a due projection therapy. Go ask the, the breweries for a discount every time and just see what happens, you know, you got to get used to it. Yeah, agreed. Awesome. Thank you again for being on. I think this was one of my favorite episodes. A lot of good nuggets of advice in here. Where can people continue to follow you outlander and then to follow your guys' journeys? Outlander.fc. We're there. We're accessible. I'm on LinkedIn. The rest of our team is on LinkedIn as well. So, you know, please connect with us. We would love to hear about what you're building and stay outlandish. Yeah, I love it. Awesome. Thanks again. We'll chat again soon. Maybe we'll do around two. Hell yeah. Thank you Matt. Appreciate you. Bye.

Podcast Summary

Key Points:

  1. Outlander VC is a generalist fund focusing on deep tech (AI, robotics, defense, energy, etc.), investing big checks ($1.5M–$2.5M) at pre-seed stage as a true lead.
  2. AJ Smith joined Outlander for its exceptional track record (18 unicorns out of ~160 investments) and to learn from top venture talent.
  3. His background includes building defense tech at 16, a music career (violin, songwriting), early crypto engineering, and founding startups—blending creativity with technical skills.
  4. Favorite part of VC
  5. Founders should pick Outlander for its track record, follow-on funding, and commitment to backing founders who haven’t given up.
  6. To get in front of VCs, founders should be strategic, use networks, accept rejection, and leverage founder friends for introductions; cold submissions are still reviewed.
  7. Pitch decks should be concise (headline-to-headline readable in 90 seconds), with the team slide being most important; show real builder experience over logos.

Summary:

In this podcast episode, AJ Smith, investing partner at Outlander VC, discusses the fundraising process. 5M) for startups solving hard technical problems in deep tech areas like AI, defense, and energy. Smith shares his unique background: building defense tech at 16, a career in music (violin and songwriting), early crypto engineering, and founding startups.

He sees storytelling as key—taking complex ideas and making them memorable. His favorite part of VC is working with brilliant founders daily; his least favorite is rejecting founders after deep engagement. He advises founders to pick Outlander for its track record, follow-on support, and commitment to founders who persist.

For fundraising, founders should build strategic lists (using resources like VCC), be ready for rejection (pitching up to 150 VCs), and leverage their network for warm intros, though cold submissions are still accepted. Pitch decks must be concise—readable in 90 seconds by headlines—with the team slide most important. , GitHub, project portfolios) over corporate logos, especially for young founders.

Overall, he emphasizes authentic connections, persistence, and clear storytelling to succeed.

FAQs

Outlander VC is a generalist fund that invests in deep tech like AI, robotics, defense, and advanced manufacturing. They write pre-seed checks of $1.5M to $2.5M for 10-20% equity, focusing on early-stage ideas with strong founding teams.

AJ joined Outlander VC to learn from a top team with a high hit rate of 18 unicorns out of 150 investments. His background includes building defense tech at 16, a music career, and being an early engineer at a crypto startup.

His favorite part is talking with brilliant founders about cutting-edge ideas daily. His least favorite is telling founders no after deep due diligence, especially after building close relationships over many hours.

Outlander has a strong track record of building multi-billion dollar companies, offers follow-on funding through an opportunity fund, and commits to supporting founders who haven't given up or shown major issues.

Founders should use resources like VC databases to build a strategic list, be prepared for many rejections, and leverage their network for warm introductions. Outlander also accepts cold submissions via their website.

The team slide is the most important, where AJ looks for evidence of why the founders are the right team. He also emphasizes that pitch decks should be clear enough to understand from headlines alone in 90 seconds.

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