Mat Vogels (00:10)

Hey everybody. Welcome to another episode of Fundraising, a podcast where we interview top early stage investors and ask them all the questions that you want to know, especially as a first time fundraising founder on the fundraising process itself. And today I have the legend, Larsen Jensen.

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founder and GP of Harpoon Ventures, which may sound familiar because that is where I work. So I have the pleasure of working with Larsen every single day. is, no, we really do. And I think that we have a couple of other folks that'll be on the podcast too. I'm hoping that folks listening kind of get a good idea of how maybe not unique the process is, but after now talking to dozens of other VCs.

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Larsen Jensen (00:40)

or displeasure, Matt, depending on the day. We have fun regardless.

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Mat Vogels (00:56)

It is unique and I think we do things in a unique way, a respectful way. So I'm excited to dive into this with you. Let's dive first into a high level introduction on Harpoon Ventures. Can you give the audience just a quick background on what Harpoon is, what we're investing in, average check size and the types of companies we're looking for.

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Larsen Jensen (01:16)

Well, thanks for being here, Matt, you know, really excited to be here and share more about Harpoon and how we think about investing in early stage companies and what we look for specifically, as you mentioned, in the process in terms of how we think about what's exciting to us and what we actually want to want to invest in. So Harpoon is a really unique early stage venture capital firm. Not only do we have about half the team that's dedicated to investing, we have the other half of the team that's dedicated to helping our founders pave the road in front of them in terms of navigating Uncle Sam and the U.S. government as a potential customer, grant writer.

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so on and so forth. we not only invest, but we actually go a step further to help our companies enter the government market if and when applicable. Most of the companies we invest in are dual use, meaning that they don't only service the government market. They might be focusing on the enterprise market or something deeply technical where there's a large commercial TAM, but we also see an opportunity for them to serve in their own way by bringing their technology to solve some of the hardest problems strategically that our country is facing in this modern era.

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that can range from AI, cybersecurity, biotech and health, energy and materials, aerospace and defense, so on and so forth. Those are all the things that are really exciting to us. If you wanted to distill it down into something very, very simple, it's sort of deep deck, previously described from the past decade, but that's what we do. And so I think really one of the key nuances is that bifurcation of the team that's hyper collaborative, has deep relationships with government customers all the way from a strategic level, congressionally.

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Mat Vogels (02:27)

Yes.

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Larsen Jensen (02:41)

through the executive office all the way down to the boots on the ground guys. You know, speaking of boots on the ground, many of our team were boots on the ground. I previously served in the SEAL teams. Many of the other members of the team were previously in Naval Special Warfare as well. Bringing that unique insight as an end user and customer I think is really interesting for us to unlock new value for the companies that we invest in. You know, we've raised over $300 million to date. It's going to be more sooner if you could read between the lines or in the near future.

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Mat Vogels (02:48)

this is

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Hehehe.

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Larsen Jensen (03:08)

which we're going to be excited to announce in the not too distant future. But we've been doing this as an early mover to this space. We started in 2018 when this whole theme was not nearly appreciated. It was very contrarian at the time. And I think we're very authentic to it and we love what we do.

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Mat Vogels (03:20)

Yeah.

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Yeah, I think it's very fair to say that Harpoon was investing into these areas way before it was cool. So we have the experience, like you mentioned, especially with the team and the boots on the ground and navigating so many of the complexities that happen, not only on the government side, but on the hardware side itself, hardware is way harder in many areas versus software. And so our team does have the experience of navigating both of those labyrinths. Let's go into some more questions about you.

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Why did you choose to get into VC specifically? Maybe talk a little bit, you have a unique background, but what led you into VC?

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Larsen Jensen (03:59)

I appreciate that, Matt. And you know, I guess for a little bit more context on me and my background, I grew up in California, was fortunate to go to school in Los Angeles at USC, swam there was fortunate to make two Olympic games in 04 and 08. Subsequently, at a rather young age, hung out my cap and goggles and joined the United States military and served in the SEAL teams for two deployments, which was, you one of the highlights of my life. But during that timeframe, we were exposed to a lot of emerging technology, some of which

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didn't really seem that emerging compared to commercial electronics like the iPhone and things like that, or the things that you just got to use personally. But we did have some glimmers of hope. We were early adopters to Palantir. We got to see how some rudimentary by today's AI was really changing the game on a lot of different ways for us and in our unit and what we were trying to accomplish. And out of that curiosity and frustration, I just became infatuated with how technology was changing the world.

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not just my job in the military, but changing the world across, you know, every aspect of our society. And so out of that curiosity, moved up to Silicon Valley, was really fortunate, the folks at Andreessen Horowitz took a chance on me, gave me the opportunity to work there as my first real job outside of the military. You know, that led to a follow on opportunity to work over at Lightspeed on the Enterprise Deal team. And it's when I was at Lightspeed that I saw this, these two worlds colliding. I still have my top secret clearance.

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I saw the rise of great power competition, all the advancements that China was making, and everything that impacts our society in terms of pharmaceutical precursors, pharmaceuticals, research, know, automation, AI, automated shipyards, all of this stuff. And frankly, the United States was asleep at the wheel technologically in terms of embracing these trends. I popped my head up and said, is there a firm out there that's specializing in this investment mandate? And there is really only In-Q-Tel.

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Mat Vogels (05:20)

Hehehe

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Mm-hmm.

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Larsen Jensen (05:47)

Incutel is the only firm, they are effectively a nonprofit that is funded by the intelligence community and other government agencies and departments as well. But there really wasn't anybody that was privately doing that. And so he said, Can we create effectively a complement to what Incutel is doing, be very mission aligned, do this for the national interest, but do it in a private sector, you know, capitalist kind of way as a pure play venture capital firm. And that's what we started to do in 2018. And it's been it's been a wild ride and wouldn't have it any other way.

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Mat Vogels (06:16)

I love that. think listeners will hear kind of throughout this entire conversation, your background and the whole team's background kind of playing into how we add that support. But before we go into some of the fundraising stuff, a few more questions on you. These were questions that were all nominated by founders. I think just to peek a little bit behind the curtain on what being a VC means, the first one, what is your favorite part about being a VC? And then what is your least favorite part about being a VC?

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Larsen Jensen (06:41)

Yeah, I think my favorite part is twofold. Like I love the chase. I love competition. Like I was in the chase going for the gold medal literally and in the swimming pool, I came up a little bit short, got a silver, but I love the chase. I love competing. I love winning. That whole journey is something that I'm infatuated by, but it's not only the competition at the end of the day for the actual Olympics or to win the deal or any of that stuff. It's the hard work behind the scenes. I might be a little bit

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Mat Vogels (06:49)

Mm-hmm.

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Larsen Jensen (07:06)

of a psychopath to just enjoy the pain of doing everything I can to improve ourselves and to improve myself to be in a better position the next time. And I think that goes into the culture of the SEAL teams as well. Like it's not only the combat operation that you go on that everybody is dreaming about, but it's the hard work behind the scenes, the teamwork, the preparation, rehearsing, rehearsing, rehearsing until it's perfect and you cannot actually mess it up when the time comes. So all of that are the things that I think apply to venture and the craft of venture that really invigorate me. But beyond that,

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Mat Vogels (07:31)

And good.

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Larsen Jensen (07:35)

you know, being so team oriented for my prior career is something that I feel like is missing in the world of venture capital. And I think it's how we assembled our team. If anybody has the opportunity to work with us, it's not just me. It's just not just Matt. It's all 10 of us. We're all working together to help our portfolio companies succeed and grow. And it's literally all hands on deck for us to try and make that happen. So it's not only the chase, it's not only the competition, it's a competition that begins again, once we cross the starting line, as we invest in a company.

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Mat Vogels (07:42)

Mm-hmm.

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Larsen Jensen (08:02)

to help them be successful and accomplish their dreams. And so that's something that's super exciting to me as well. The thing that I like the least about it is probably, you know, actually the thing that founders have to do as well. They have to fundraise. It's probably their, their least favorite part of their journey. They're business builders after all fundraising is a critical part of that to resource them being able to accomplish their mission. It's the same thing with us. We need to fundraise to accomplish our mission. I love telling the story.

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Mat Vogels (08:18)

Mm-hmm.

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Larsen Jensen (08:29)

but at the same time, you know, it's still not my favorite part of the process.

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Mat Vogels (08:33)

No, absolutely not. At the end of the day, you're right. We're all builders in a way and fundraising is very important, but kind of feels tangential part of what we like to do. It kind of goes to a similar question. The next question that founders wanted to know was, do you wish there was something that founders maybe better understood about what it is to be a VC? Fundraising is definitely a common answer that we get for that. But is there anything else you want to add to potentially some things?

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Larsen Jensen (08:58)

Yeah,

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I think there is. I think it just depends on the firm, depends on the franchise. Most VC firms or a lot of the bigger household names have been around for a long time. They've proven their right to exist. They are extremely successful and we all admire them and hope to be them one day as we grow up. And so I think there's a little bit of a misnomer out there in the VC community or at least with founders as they think about the VC community applied to Harpoon and other firms like us that are still somewhat emerging. We've been around for almost a decade, but this is such a long-term game.

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know, it takes decades to build like a generational franchise, which is really, really unique in this asset class. So I think that I think that we're more like founders in the sense that we're building our business now we're not yet established, we're not yet an incumbent. And so I think a lot of founders think of VCs as people that sort of just hang around and wait for a meeting and you know, it's pretty luxurious or something along those lines. That's sort of like the

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Mat Vogels (09:48)

hehe

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Larsen Jensen (09:53)

you know, the media view of the venture capital community, which can be true for maybe some of the more established incumbents. But for the best VCs, even if they're at that incumbents, they always have an axe to grind. They're always competing. They're always trying to do the best they can to improve their franchise and to improve outcomes for their founders. And so it is actually a lot of hard work. But at the end of the day, we're not building a really core technology. It's not nearly as hard as building some hard tech thing that goes to space. So all respect to the founders out there. But I think the DNA

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of how we operate is very akin to how the DNA of the founders that we invest in.

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Mat Vogels (10:27)

Yeah, that's been a very common answer that we get from folks that were operators turned investors is that they were surprised at just again, it's not as hard, but it's a lot of it is a lot of work.

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Larsen Jensen (10:35)

What are the other things like not to interrupt, but it's so funny

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coming from my former background in the military, like the special operators, special operations, those are operators. And so when I came into like VC and the tech, I was like, oh, I'm an operator. like, I don't know if we're speaking the same language here. The operators I'm used to are the ones who are actually special operators kicking down doors and shooting bad guys. And so operators in a business context is very different. I guess everybody has a term operator, whether you're a surgeon, you're an operator.

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Mat Vogels (11:01)

Yeah. Yeah.

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Larsen Jensen (11:01)

You're a special operations, you're an operator,

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business builder, you're an operator. Everyone wants to be an operator regardless of the field, I guess.

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Mat Vogels (11:07)

Yep, but it's the same thing where they think like, VC, it's like, you just go on vacation for three months of the year and then people come to you asking for money and that's all you do. And it's usually not the case. It's your point for the best VCs, it's not. All right, next question. What are you personally excited about as far as the problem sets or innovations that you're kind of seeing right now? You mentioned some of the ones earlier from the thesis in Harpoon, but maybe for you personally, what are you excited about?

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Larsen Jensen (11:17)

That's not the case.

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I think there's a full stack underwrite of building the AI ecosystem. I mean, it's something that's a new market inflection. It's only been around for a couple years and we're tremendously early in this journey. It's probably akin but faster than you know, by by any measure than the dot com era in terms of the platform shift to the internet. And so with that, you need not only greater compute greater connectivity, you know, more more bandwidth, you need all of those things to actually just get the foundation models to actually be possible at scale in the first place. And then we have the foundation model arms race.

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which allows more at the application layer for really, really idiosyncratic problems that previously were probably not venture scale that are now unlocked to be possible. And so long story short, I think almost everything that we've invested in that's successful has some AI angle to it, whether it be on the hardware or infrastructure side of the house, you know, in space, you know, communications and other things of that nature, all the way down to terrestrial energy, nuclear,

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You know, energy, material science, it all really has room for improvement to make our chipsets more effective into the pharmaceutical industry, cybersecurity, to actually core model layer providers into the application layer. whether by by accident, which oftentimes it is or by design, really the full stack of I think everything that we've invested in, you know, intersects with this AI transformation. And we're certainly in the early innings, I think we're bottom of the first inning.

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Mat Vogels (12:48)

Mm-hmm.

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Larsen Jensen (12:59)

in a lot of this stuff. We're not even close to being halfway through we're not in the seventh inning stretch. I bring up a lot of these baseball analogies because our offices by Petco Park today's opening day at the recording of this. And so a lot of excitement around the baseball season. But you know, nevertheless, those are the things that we're really excited about. And when we look when we see a new company, it's like how even prior to AI, why is now a unique time to build this business is always a question we'd ask, and always a question the best VCs in the world ask.

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And so now that right to win oftentimes comes with a technology mode and something that previously wasn't possible until the modern era of technology that's only occurred over the past number of months to past couple years.

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Mat Vogels (13:38)

There was a kind of an interview going on around X right now from Toby at Shopify who said that 2026 is the year that every single industry and business is up for grabs and many incumbents will continue to innovate and stay there. But to your point, every inch of every business is now being affected by this, which could lead to all kinds of new opportunities and things. It feels like a Renaissance in a way, right?

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Larsen Jensen (14:02)

It does. It does. And we'll see how this all plays out. But I think everything's up for grabs. And I, you know, as you've talked about and written about very astutely, I think we are going to have a gap in the labor labor force. We have lot of traditional jobs that ultimately AI is going to be, you know, improving or displacing, depending on the situation. And so I think that not only is this a technology ecosystem, you know, thing that we need to confront, not only is this a business issue that we need to confront, this is something that you know, our own government and governments around the world.

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need to understand and ultimately embrace in order to create a more prosperous future for the citizenry. And so there's a lot of unanswered questions, but leaning into that, I think is the only way to play it because it's it's inevitable.

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Mat Vogels (14:44)

All right, last question here. This is kind of your minute or so to shine some light on Harpoon. This is a question that founders wanted asked or answered. Why should founders pick you and or Harpoon to be on their cap table?

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Larsen Jensen (14:59)

I think we're the most authentic firm to investing in the national interest, short of probably In-Q-Tel. I think they've been around the longest and they have earned it and I have all due respect to them. But I think second to that, think founders would really struggle to find another firm of the DNA of Harpoon, of people that literally have worn Team USA and represented our country across not only the playing field, but the battlefield to now the world of venture capital.

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And there's been a lot of new entrants into the space that I think just lack the authenticity that we have. It doesn't mean they're not fantastic investors. So if you want that authentic team member who not only says they're going to be in the trenches with you, but has literally been in the trenches previously, and knows what that term actually means, I think that we're the best fit. And beyond that, I mentioned at the onset here that we have not only an investment team, but a team that assists our portfolio companies in a very unique way.

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This is one of the things that I learned from the Andreessen Horowitz franchise is like they're not only investing, but they have a whole services army to help you and recruiting and PR and marketing and go to market. We really have tuned that for founders that are interested in building for the national interest or believe that their technology at some point could intersect with the national interest, which is pretty much any large scale outcome that we've seen in the history of the technology market. So it is very, very wide. Even if it's not today, if you're building a technology company of consequence, you are going to intersect with Uncle Sam.

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period, whether that be, you know, regulatorily, whether that be for funding, whether that be as a customer, you are going to have to do that. And we built the muscle movement to be the best in the world at helping companies do that.

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Mat Vogels (16:32)

One of things that we say a lot internally is that Uncle Sam is the largest customer in the world. And eventually to your point, many of these businesses will be interacting with them. having us in their corner is true.

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Larsen Jensen (16:41)

100 % I don't

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think that a founder can say two things to the same or say that you're going to build a technology company that's going to change the world. And if that's the case, obviously, there's going to be consequences on the hill, and there's going be consequences, you know, with DC, look no further than Facebook, you know, in terms of election, you know, issues, so on and so forth, look no further than x things that appear benign at the time, if they are going to be huge, end up transforming not just industries, but chant transforming civilization.

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And so if that's the case, Uncle Sam will wake up at some point or another. And so we want to be a critical part to help make sure that they are woken up in the right way.

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Mat Vogels (17:20)

I love it. All right, going into a lot of folks are here for the fundraising process itself, which has the title of the podcast mentions is actually it's no fun at all for VCs or for founders. It is one of the hardest parts. And so we created this to essentially give founders a little bit of a peek behind the curtain on what a top VC is looking for, because there's not a lot of information out there that educates founders on what this process actually looks like. If you haven't gone through it yourself, a lot of people listening are first time fundraising founders.

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Larsen Jensen (17:44)

100%.

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Mat Vogels (17:49)

and they have no idea what they're getting into here. So hopefully this adds a little bit more light for them. The first phase of the fundraising process, I like to call getting in the room. As VCs, we get hundreds of pitch decks and emails every single month from founders that are looking to fundraise. How do founders stand out? How do they create compelling pitch decks that help them get their first meeting, which we'll get into in the next phase here. But...

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What we're seeing a lot of founders do is create a list of investors that they want to start reaching out to. It's almost a mini CRM. So the first question for you is what advice would you give founders on the characteristics or traits that they should be indexing on when creating that initial list of VCs to reach out to?

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Larsen Jensen (18:30)

I am creating the list, I would look through look at podcasts like this. There's many other venture firms are going to be on this and they're already on this. And so just trying to like understand who's the right fit for you thematically and culturally. And it's okay if somebody is not a fit for us, like you know, it is what it is, or vice versa. And I think everybody else feels sort of the same way. So I think looking for making your best guess at relationship fit is probably something that's under indexed for everyone looks at sort of like thematic feet fit.

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just because they have a thematic fit doesn't mean you're gonna enjoy working with them. And at the end of the day, these are 10 year commitments in terms of like how you're engaging with your investor base. So thinking about that really intelligently, I think is something that's really good to do upfront to the maximum extent possible.

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Mat Vogels (19:13)

Yep, that's a great answer. Are there any things that founders can do on the outreach process that you think it could be just for you or for Harpoon that gives them a better chance? it LinkedIn? Is it cold emails? What is it?

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Larsen Jensen (19:22)

100%. The single

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one is coming in through an existing founder that we've invested in. Number one, everything else, very far second place, wide margin. Number one, coming in through a founder, getting an intro through a founder that we've worked with before, that we have a really strong relationship is the single best way to do it. Number two is probably through other venture firms that we've co-invested with before, to the extent they're already an investor or they're already interested.

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Mat Vogels (19:28)

100%.

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Wide margin too.

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Larsen Jensen (19:49)

But you got to be careful with that because you don't want to come in through a venture firm that's not investing and have to sort of explain that away. You know, the whole adage is like, why are we so special? If you came in through another venture firm, why didn't they invest in it? And that's the first question I'd ask. And so I think authentically, that barrier is gone. If you're coming in through a founder that we've already invested in, ideally this in the same sector that you're operating in with a thumbs up, vote of confidence saying, hey, you got to meet my friend.

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We did our degree together or we worked together at X, Y, and Z, you know, startup or incumbent. He was one of the best people there and he's got an idea like that is number one way to do it. I really to the maximum extent possible recommend against cold inbound, cold, cold, linkedins and things like that. I think going spending the time on your investor target list to come in through somebody that's a friend of yours or a coworker formerly of yours, probably the best.

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to say, you really got to meet my friend. And I think that'll help you stand out more than anything else.

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Mat Vogels (20:48)

The next question that comes from this when warm intros are obviously the best way of doing it for folks that maybe don't have as many, they've been out of this ecosystem. Any advice for them on how they can start building some of those relationships beforehand, even months before they go out to fundraise?

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Larsen Jensen (21:04)

I think this is something that goes back to like the prep preparing for a Navy SEAL mission. You got to do the work ahead of the time. You can't just go onto the target and expect that this is all going to work out. I mean, you could, but you're really rolling the dice in terms of your own safety. So why risk it? Why risk it if you have the time to prepare? So go to industry conferences, spend a lot of time building relationships, know, win over other founders in terms of how your technology is different and unique. And if you sort of like spend the time working that ground game,

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I think it'll pay off in a lot of different ways recruiting for your own team, customers down the road and ultimately investors intros like we're here talking about today.

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Mat Vogels (21:39)

Yep, agreed. Are there any, so let's say that they've done all the right things, they've gotten their pitch deck in front of you via warm intro or what have you, are there any slides in particular or things that you look for as a VC that stand out that maybe you go to first before even reading the rest of the pitch deck?

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Larsen Jensen (21:54)

You know,

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before even getting to the slide, I think one thing that I'm guilty of too, in my own fundraising is trying to kill everybody with overwhelming information in that first email. That's the surest way to actually not stand out. And I experienced this too. Like when I'm, you know, fundraising from LPs, I want to tell them everything that's amazing about us for them to try and find interest in us.

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I think the shorter that you can be, the better. And that's really, really an art and hard to do because what's the old saying? Like if I had more time, I would have written less. Like that is, that is sort of the art and the challenge with this. So if you're writing something that's literally more than four sentences, I think it's really hard to stand. If you can't communicate why you're different and what's going on with you and your technology, your team and the market and four sentences, I'd go back to the drawing board because if it's four paragraphs, it's not that people are lazy.

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It's just that it looks like you're desperate. I hate to say it, but it looks like you're desperate. And when I fundraise, same thing. If I'm over killing with all these form emails and it's a super long essay, it looks like I'm desperate. And guess what? I'm not going to do. I'm not going to get that meeting with the pension or endowment or family office that I want to meet with. So I play the game the same way that the founders do. So I think I sort of have learned by failure myself what not to do. But as far as like the thing that's a key unlock.

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It's really rarely on the technology and describing that, at least for us, maybe for somebody that's a cybersecurity expert, they wanna see that. But for us being somewhat generalist, that's not it. It's the strength of the team, first and foremost, and the market insight in terms of the problem. Like those two things, I think, are the things that make us jump out of our seat and wanna learn more. And if you have a really, really, really strong team, extremely well.

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credentialed or pedigreed or somebody that's just a brilliant savant, maybe a young guy who's 18, 19, 20 years old. Like those kinds of things actually stand out as long as it's nested in a problem that is so large. And the favorite situations that we have, at least I have is like, holy cow, this is so obvious and so simple, but nobody for whatever reason is doing it. And it's only been possible because of an unlock in technology that you uniquely have. If you can communicate that very clearly.

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Mat Vogels (23:57)

Mm-hmm.

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Larsen Jensen (24:04)

it'll get the meeting, especially if it comes in through a founder that we've invested in before.

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Mat Vogels (24:05)

Yep.

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Absolutely. Is there anything on a team slide specifically? If that's one of the more important ones, visuals, logos, what do they need to talk about or not say on a good team slide?

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Larsen Jensen (24:18)

clearly communicating how the team and if that's one person, that's fine. So the individual and or team are true outliers. Everybody thinks they're an outlier, Matt, you think you're an outlier, I think I'm an outlier, everyone thinks they're an outlier. So but like you have to like communicate that in a way that's actually like realistic and relative to everything else. Another way that I another anecdote that might help to frame this is, you know, I went to Stanford Business School a number of years ago, I went as a veteran.

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And routinely I'll talk to other veterans that are applying to go to grad school or want to get into the Stanford GSB and I'll read their essays and I'll say like and but every veteran essay pretty much all sounds the same and Obviously, these are heroic experiences like more heroic than mine by by a wide margin of like going through true adversity But if you put yourself in the seat of the admissions cadre at you name the university

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How are you standing out versus all the other veterans that are saying the same thing that you went to combat, you had some, you know, crazy experience and you you got through it, some framing of that. Well, they've got 200, 300, 500 other veterans that are saying some version of the same thing. It's not that you're not unique and special, especially in the, in the scope of the greater populace, but you're competing against hundreds of other veterans that have some version of the same story. Why is that?

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Why is your version of this truly unique and different than anybody else's that's coming in? And so if you put yourself in the founder's shoes to say the same thing, like, I'm sure you're smart. I'm sure you're well pedigreed. I'm sure that you have a unique market insight, but so does everybody else. How do you zig while everyone else is zagging? How do you outflank the enemy? How do you outflank the venture capitalists like us? How do you not just come at it with a frontal assault to say, we're different, but everyone else says they're different. So really having something to laterally move that's like,

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is truly different or adds depth to the pedigree of the team, I think is a huge, huge feather in your cap.

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Mat Vogels (26:13)

It's almost the why. Like why are you so interested in taking the 10-year journey or longer on this?

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Larsen Jensen (26:19)

Totally. 100%. You said it more clearly than I could. Thank you, Matt.

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Mat Vogels (26:22)

Nope,

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that was great. Last question in this particular section. What are some of the mistakes that you see founders make, whether it's in the pitch deck, the way that they're doing outreach? You mentioned maybe having something that's too long, maybe too in the weeds. Any other mistakes or common things you see founders make in that phase?

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Larsen Jensen (26:36)

Yeah, think in

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this part of the process something that's Less is more believe it or not people want to say more on their pitch decks and it's sort of like less is more and to the extent you can't simply describe it in a very clear way You know, I recommend going back to doing that. So I lots of decks. I think the biggest ones that are almost the ones that are Somewhat easy to dismiss to dismiss or the text heavy you know decks that just You have to

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you read a lot of them, but they clearly are written by AI these days. And they have a lot of like, buzzwords to try and like fit in because you think that's what venture investors want to see. It just really doesn't. just knock them over, you know, bang them on the head with a high quality team and a large problem that's unsolved. Like, you know, the least competitive the better. And you know, I just came back from Hill and Valley also and many folks were, you know, on the record of some interviews thereafter.

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like lots of people are trying to build the andro for x like stop building the andro for x, like just build something that's unique, don't comp yourself against anybody else and say you're doing that. And I think if you have that insight that you're building the you know, first of its kind, you're gonna go to zero to one and a first of its kind business, you're not trying to build something that's you know, effect effectively, you know, by analogy there.

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Mat Vogels (27:54)

Love it. All right. Let's say they've taken all this advice. They've crafted the perfect pitch deck, all the things right. They now have an initial meeting with you, Andor, Harpoon. So let's go into that phase of the process, which in itself, you know, it's only 30 minutes, but as you stack these up across, you know, dozens of VCs in this particular phase of all these introduction calls, it's such an important part about the, about the process from your lens. What is it as a VC, where are you looking for in those 30 minutes from a founder so they can become

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better prepared for that 30 minute interview.

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Larsen Jensen (28:26)

As crazy as it sounds, you'd probably agree with this and I've heard other venture firms agree with this. sort of know whether not for sure if you're going to invest, but your level of interest in the first five to 10 minutes, first five to 10 minutes, these calls should be five to 10 minutes long. And it's probably the same thing when we fundraise to people on the other side of the table, they know whether they like it or not in five to 10 minutes, it doesn't take an hour, it doesn't take 30 minutes, all of that is just getting into the details to validate or invalidate that initial interest.

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And so I think that first five to 10 minutes that go time is really, important, but you can't make it seem rushed. It's got to be still somewhat casual. You can't appear desperate. You have to sort of be the big dog. And if you are that really helps. And thereafter, time kills all deals. And so as you architect your fundraise, I think it's important to get some dry runs out of the way, probably with other founders to get some feedback, maybe some friendly firms with insiders. If you have some with the angels to sort of like craft this.

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But I also think I'd be cautious about who you're getting advice from, because the world of VC is different in the world of angels, unless they're like native to the VC ecosystem, which many, are these days. But I'd be cautious against working with, you know, people with a PE background, other investment experiences, family offices who have been who've gotten wealthy on traditional businesses, and taking their insights as it relates to oversight intersecting those with the world of venture capital, because it is very, very different.

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If you come in with a PE style, you know, pitch, come in based on the advice that you get from angels that are not tech native, you're going to fall flat on your face and it's not going to go well. not, not because we hope that's the case, but I just think it's just a different creature. and podcasts like this, I think will help prepare you to sort of like know how to come in. But I think right out of the gate, starting with the problem right out of the gate, be like, this is a huge problem. It hasn't been technically possible before.

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we believe it is or we validate it, we have a unique technology or there's unique technology in the market that allows us to solve this. This is a 10s of billions of dollars, you know, annual revenue business very quickly. And let me tell you why we're the only people in the world to do this, like very, very clearly, very, very succinctly. And you need to dub it down to as if you're talking to your fourth or fifth grader, like every VC thinks they're super brilliant and many, many are but

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Mat Vogels (30:36)

Yeah. ⁓

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Larsen Jensen (30:39)

Like you gotta you don't know who you're talking to at which juncture and so if you're talking to some of these deep in the weeds technology, you might want to start there. If you're talking to a generalist, you might want to say, all right, let me like boil this down to basics for you. Larson. Here's the problem. Here's the desperation. Nobody solved this. We have and we're raising a few million bucks. Go get this going.

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Mat Vogels (30:58)

No, and that should be something that is captured like right away. You can capture all of that and then almost like turn it over to the VC in a way to steer the conversation. One of the questions we have here is, so these were questions again, they were asked by founders, pitch deck or no pitch deck, which kind of goes into that. It's like, do you just want people to read a pitch deck for 30 minutes at you or how does that transaction look?

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Larsen Jensen (31:01)

right away.

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we prefer to see a deck in advance. ⁓ Personally, we can glance through it, it's probably not going to be a super deep exam, but glance through it to have a level of familiarity. And the ones that are easy for us to like understand is where we have, you know, done some investments in the space. And so we sort of like immediately know there's a problem there, because we've heard of it. That's sort of like the simplest ones to do, and I think are the easiest to pique the interest to the extent more education is necessary. You know, so be it, that's fine.

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Mat Vogels (31:20)

course.

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Larsen Jensen (31:42)

And there's plenty of times where we need to be caught up and like don't understand and don't know and we have to ramp up very, very quickly. So I think as dealers choice, I think whatever you're more comfortable with as a founder is the way to go. That speaks to the authenticity. If you're running this process, just to impress VCs, you're going to lose like you got to like be authentic. You got to be yourself. It's better to like get nose because people don't like you than it is to get yeses pretending to be someone else. And it's the same for us when we fundraise too.

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It's frustrating, but it's the reality.

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Mat Vogels (32:11)

It really is. One of the other questions was whether there's a preference on the whole founding team being there, just the CEO being there. What kind of dynamics have you seen there? Just CEO. Any particular reason or yeah.

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Larsen Jensen (32:20)

Just CEO, just CEO, just CEO. Again, because if you

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have the whole team, appears desperate.

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Mat Vogels (32:27)

So true. And also it's a weird thing of having exactly. That's what I was going to say.

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Larsen Jensen (32:28)

⁓ and also you can't and don't send your CFO. Don't have somebody stand in for

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you. You have someone stand in for you. Like, dude, it's an immediate, like it's going to be a pass unless for some reason you are the hottest company in the history of the world. And the founder literally doesn't have time for you. But like, if you're that founder, you already know it. You don't need to listen to this. Like it's already been happening in like your rounds already oversubscribed. but even then I think it's probably not the best look. So I would say just CEO for the first meeting. And if people

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Mat Vogels (32:45)

Mm-hmm.

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Larsen Jensen (32:58)

want to dig in, they'll they'll sidebar say, Hey, let's get the whole team on the next meeting, things like that.

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Mat Vogels (33:02)

Yeah, especially if it's highly technical, we see this all the time, or if it's the CEO, the first meeting, if we're excited to keep going in the future meetings, we can get more technical. Having the CTO there, somebody that's very technical can help, but definitely not in the first one. What are some of the mistakes that you see founders make during the meeting that they should really look to avoid? So within those five to 10 minutes, you've already lost interest and are now ready to hang up. What are some of the things they're doing for that?

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Larsen Jensen (33:14)

100 % 100 %

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I think the mistakes go back to the planning of this where they say, Hey, we are the only team in the world to do I don't know some version of what's happening in defense tech these days where there's literally dozens of competitors that you could just Google or chat GPT and saying, but we're we're better than everybody else. It just becomes a race to the bottom at that point. And like the the curve to get over is way too hard, which is probably sort of an indictment on the idea in the first place. It's not that you can't do it. Some people do but there really needs to be a clear differentiator.

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on like why you are the best. And some firms are really, really good at this at market mapping entire spaces that they're excited about and picking and anointing the winner that they believe is going to be the one to capture the largest segment of market share. But when things are, when you're saying that this is a market's not competitive, and it just clearly is by doing a quick Google search or a quick LLM search, it shows just like tone deafness unless the team is just

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has some novel invention and the team is just so pedigree that it's just crazy. But I think the biggest, you know, the biggest red flag is saying something's not competitive when it's clearly competitive.

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Mat Vogels (34:33)

Yeah, yeah, don't try to hide behind that. One of the other questions that founders really wanted to know, sometimes they get advice that they should also be asking questions, that they should kind of flip the table a little bit and ask VCs questions. What are some of those questions that they could ask? This isn't necessarily to impress us, but more because they should take a little bit of control and ownership.

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Larsen Jensen (34:51)

Yeah. Well, the one the ones I don't like

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actually are the ones I've been, you're a white combinator guy. You just got back from demo day. I don't like the white combinator ones where they're like, you know, forced reverse interviewing the VCs in a really abrasive kind of way that like it's a little bit of a turnoff to be frank, because we're not like doing that to them either. We're not like coming across aggressively. So it's all in the tact, right? It's all in the tact. And so I think those are, it's a great thing to do, but don't just like come off and be rude about it. And I think that's, that's hard.

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because we don't want to come off and be rude and like some of the things I'm saying here, like we would never say in a pitch because we would never say, well, you're not, you are actually competitive with these 10 others. We'd be like, we say it through curiosity. How do you think you're not competitive? Cause it appears like you might be like just like in that simple change in tone, vocal inflection in words, it matters a lot. And so in the same way, I would suggest founders to like, like I see that you have some of these other peers in the ecosystem. Like they seem really, really good too. Like why do you think that you're, you know,

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you know, the best situated to invest in a founder like us compared to like, you know, these other folks in the space, just gives us some breathing room to, you know, have an honest conversation and it becomes very cordial. And so the way that I've seen some YC founders do it is very abrasive.

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Mat Vogels (36:03)

Yeah, it's almost like we're being interviewed before we can even ask questions in some cases. ⁓ What about questions related to the fundraising process? Is it okay for founders to ask, you know, how long is this going to take? What does the process look like? Is there any questions like that that they should be looking for?

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Larsen Jensen (36:07)

Totally.

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I think it does, but it's all made up. you know, VCs are going to tell you whatever they, you know, it's not, nobody has like a farm. Some people do have a really hard and fast timeline. Like, Hey, two days, three days, two weeks. It's all deal dependent at the end of the day. And if that's why time kills all deals. So it's good to know, if somebody, listen, all VCs that are respectable out there can run an accelerated process when they're really excited about something. And so I think

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the longer a process goes on, if it's been a month and you're reaching back out and it's just it's just, you know, 90 % plus not going to be a fit, there's 10 % where maybe it is, but it would require a new inflection. So I think that's why it's so important to architect your fundraise in a point where you're well prepared, well rehearsed, you are well researched. So that when you kick it off, you actually can meet a lot of venture capitalists all in a very tight timeframe.

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to try and create a competitive constrained process. And we're going through this now founders done a great job. You what we'll see how it all plays out on our side. We're really excited about it. But you know, great, great accelerated process. And there's an old adage out there if you want to raise more, ask for less, you know, if you want a higher valuation, ask for a lower one. Like, it's sort of these like non obvious obvious things that I think some of the best in the business have sort of perfected.

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Mat Vogels (37:37)

Last phase of the process is kind of the big meat of it. It feels simple, but it's a lot of herding cats, building FOMO, building momentum. But let's say that they've had a good at first initial meeting with you or Harpoon or any of these other VCs. What is a typical...

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diligence process look like for Harpoon? Let's just start there.

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Larsen Jensen (37:55)

Yep. Typically, it's meeting the broader team. So to the extent there's other people involved, back channel references on the founder and on the market are sort of status quo, you know, independent research, you know, through various databases, so on and so forth. market mapping and competitive landscape to validate that there in fact isn't one or one where there's a gap in the market where somebody can shoot through it and actually potentially achieve success. All of those things. And it depends on timeline. I mean, although we have we have a relatively small team,

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But all venture funds like rarely dedicate like dozens of people to doing something. So it's still always a small team, regardless of the size of the fund or the firm. It's always sort of a squad size, you know, or fire team sized element of a few people who are going after this and investigating these things, which would require people to drop everything if the pressures are there and other things they have in the pipeline, other things are dealing with their own LPs, other things are dealing with from a firm wide management standpoint, other ongoing board obligations. And so

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In some ways, you just need to create an incentive structure where people are going to cancel their other meetings to dig in and do the research and the work they need to do to get there quickly. And that's even in a higher bar. Like people think about this as if it's a single deal dynamic versus but they're also but it's not at the end of the day. It's other deals they're prioritizing. It's other portfolio companies that might be having a huge problem or fundraising themselves or firing people or lost a customer or whatever.

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And so I think too often founders sort of like don't realize that there's more going on behind the scenes of the people that you're talking to. And you need to create a way where you become number one on their priority list versus all the other priorities that they have. And they certainly have other priorities. Nobody realizes that nobody thinks about that. How do you work your way up from being like number 10 priority on a given day to number one priority for a period of a week or two?

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That is the level you need a conviction you need to see and build in order to get things something through on a a semi reasonable timeline. And there might be other problems. Maybe they've invested 10s or 100s of millions of dollars in a company that lost a big deal or, you know, Claude is beating the product and it's like they got to figure that out. Like that. That's money that's already been spent. And they have to help like the founder and work through the navigation of that. Or else that company could go to zero.

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Mat Vogels (39:57)

Yeah.

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Larsen Jensen (40:17)

And so how are you as an N plus one company and investment, although extremely impressive, like worthy of that counterparties time to focus on you to getting through to to a yes or a no. That's something I think is not commonly talked about or thought of.

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Mat Vogels (40:32)

Is there any way to do that tactically? Because we see founders make a lot of slips and mistakes during this part where they're building FOMO, but maybe doing it in ways that are shallow and end up coming back to bite them.

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Larsen Jensen (40:42)

I think that's

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some of the questions that you have like, what's going on with you? Like, what are you like, you can sort of tell in the stress or the, know, of the other side, like how busy are they? How not busy are they? How excited are they with you? You can sort of like read into that a little bit. And it's not a perfect science because everyone has a different personality. We tend to be happier and more excited. Other venture firms maybe are more understated and you know, so it's, hard to know. So I think knowing who you're meeting with beforehand and sort of like how they operate is probably a good thing.

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But that's probably one of the questions like, Hey, how are things with you? Like, how's the portfolio going? What's going on? And, you know, if you could sort of like glean some of that, you might have, you know, a better chance of getting more airtime with with them. And also, it is oftentimes so much more VC led in terms of their proactive engagement. If they're calling you, they're texting you, they're emailing you and sort of like on top of it. That's a good proxy for interest. Same thing for us when we fundraise, I had to keep bringing up our own examples, but

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When somebody is constantly asking us questions and wanting to get back on the phone and looping in other members of the team and spending time in the data room and like we can see all that just like founders can see with us, like you know, they're interested and so actions talk bullshit walks, like you got to like, you know, see what the actions are to validate interest if they haven't heard from them, there's no engagement, you know, their actions don't, you know, suggest that you should re engage aggressively.

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Mat Vogels (41:59)

Yeah, a common thing that it is, it absolutely is.

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Larsen Jensen (42:00)

It's like dating man. It's like dating go back in time. I don't know I've

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been married for 13 years It's been a while but like, you know in the courts Courtsmanship process of all of this like if it's not being reciprocated the chances of being a yes or a rather low so it's the same thing put yourself back in high school and VC the ecosystem is sort of like high school like nobody says that but this is all high school man and so If it's like high school dating and the other person's not interested in you, you know

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Mat Vogels (42:15)

Mm-hmm.

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Feels like high school. ⁓

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Larsen Jensen (42:27)

you might want to take the hint.

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Mat Vogels (42:28)

funny, Andrew, our colleague, this whole part of the process, he had the same metaphor for being like the prettiest girl at the dance. Like how do you end up making yourself the prettiest girl at the dance that everybody wants to dance with? But you have to do it in an authentic kind of way. Cause we can see through that. We talked to other VCs too. So building FOMO and saying that X, Y, and Z fund and we have a term sheet with them. It's like, well, a quick text away from figuring out if that's true or not. And there's a lot of deals that ended up ending that way.

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Larsen Jensen (42:53)

Totally, exactly.

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Mat Vogels (42:56)

One of the common

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questions or things that we get here are, I'm oversubscribed. It sounds weird. It sounds like a nice problem to have, but oftentimes founders do get to the point where they're slightly oversubscribed. They have one or two VCs that maybe are circling back after saying no two weeks ago, but now that the round is about to be closed, they're interested again. It adds this weird shuffle of who do you want on the cap table and who do you want to leave off? So the question for you is what is some advice you give to founders on

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making the right choice if you can, because you mentioned this is a courtship. It's an important relationship that sometimes you only get two weeks, know, maybe two hours worth of meetings to make a decision on how can they make the right decision and picking the right investor to leave on or leave off.

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Larsen Jensen (43:31)

Yeah.

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If you're in the unique position where you have multiple offers like it depends on leads follows co-leads so on and so forth So there's a handful of combinations and permutations of this Ultimately, if it's somebody if you're if you're up against multiple parties that all want to lead saying you're oversubscribed It's probably the wrong word to use. It's probably a good word to use in terms of followers, but ultimately saying like hey, I've got multiple offers I'm trying to pick the best partner like and what I see go wrong a lot and it drives me crazy when we actually have our own

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founders that do this is they optimize for valuation versus the partner. Like, if we all believe that this company and you as the founding team believe that this is going to be a multi billion dollar deck a billion dollar outcome, optimizing for valuation within general ranges at an early stage is just not smart. I don't know what else to say. And because over if it's almost like an indictment on your own confidence of how big this is going to get.

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Mat Vogels (44:34)

So true.

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Larsen Jensen (44:34)

you optimize

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for the right partner, which is a combination of what they offer their brand, their network, you know how hard they work, so on and so forth. All those things should be taken into consideration. But if you're optimizing for value, in terms of dilution, ⁓ sort of a problem. But there's anomalies out there where some people like who are not native to the venture space will be rather predatory in terms of valuation and, you know, to a certain extent.

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Mat Vogels (44:49)

Yep. It's a common mistake.

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Larsen Jensen (44:59)

if that's the only option you got beggars can't be choosers, man. So like at some point, you got to get off your high horse and just like capitalize the business to get the job done and work with the team you have and the resources you have versus like killing yourself when you've gotten those from the people that you wanted to work with if that's case. So you know, you got to be realistic. But at the same time, don't optimize like if it's a if you're raising a series A and it becomes like

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you know, a $15 million round from like your ideal partner at a 25 % lower price versus a $20 million round at a 20 % higher price from somebody that you really isn't your favorite and doesn't credential you the best way possible, then I'd take the lower valuation seven days out of week out of the week and twice on Sunday.

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Mat Vogels (45:42)

Yep. All right. Let's say that they've made the right choices. They've closed their round. What's some high level expectations of what maybe you as a VC are expecting on behalf of the companies? What should the founders be doing for updates or communication? And then likewise, maybe what are some of the expectations that founders should have of the VCs that are now on their cap table?

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Larsen Jensen (46:02)

too many VCs invest in our sort of like gone until the next round, basically, I think that's the majority of the industry. That's the that's true for the majority of the industry. But I think for us, what we want is like not over engagement, because they have over engagement that implies that you don't know what you're doing, and you can't execute as an executive team yourself. And so I think that that is a bad thing. But to the extent like but also founders are really, bad about asking for help. And that's also I think, not great to the extent you have

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Mat Vogels (46:08)

That's expectation setting up, I think that's true.

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Larsen Jensen (46:31)

things that we could actually do we want to do it. We have one of our founders that actually like ghost writes me emails to candidates he's trying to close. That's basically in my voice. And I basically just need to copy and paste it and send it and hop on the phone and help help him to close that candidate. He puts me to work. I didn't ask for it. He forces me to do it to close these these, you high level researchers and engineers he's trying to bring on. Dude, thank you. You just made you just told me what to do. And you actually made it really, really easy for me to do it.

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The ones that think are less sort of like, you know, useful are, hey, can you help me with this? And I really don't know what to do with that, right? And it's not that I don't care or don't want to, I just don't have the action plan. Just make it easy and do the other person's work for them if you have something you actually want done. Customer intros are another thing. We have another founder who is like synced his LinkedIn with our LinkedIn to go through mutual connections. I don't know how he did it.

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And ultimately he's like, he's like, hey, do you know this CISO at this firm? Like if so, how well if you do, could you actually send them this very specific message about the thing that we're doing that I know they have a problem for? And and like we've done this like for 20 different customers on like 17 of them, like I don't know how I'm actually connected to this person, but for three of them, I'm like, yes, that's a buddy from whenever no problem.

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Mat Vogels (47:38)

yeah.

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Larsen Jensen (47:46)

you framed it in a way that's solving their problem. I look like I'm doing this person a favor by bringing you in, but I'm actually doing you a favor. Like that architecting is like really intelligent. And you know, all of us are happy to go to work and do those things. On the founder side, I think also a lot of people don't really think about investor management, regardless of the size of the investor within reason. But if they're a material investor, they own, you know, 510 15 plus percent of the company, like, it's nice to get an update.

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Especially as you grow and you outgrow sort of maybe those early stage investors It doesn't need to be monthly but quarterly would be great. Some people send us monthly just emails, you know BCC all investors or to their investor domain That's really really nice because at least like we feel like we know what's going on and we can be helpful if required And also we have investors too that we need to report to we have annual audits We have to do that too. Every firm does it's a that's institutional firm And so I think sort of like putting yourself in their shoes is a great, you know partnership

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thing to do. And partnership is a two way street, it can't be a one way street. And so I think those are the things that we appreciate quarterly updates, you know, even followed up by an individual call, you have a bigger cap table, maybe doing a group call, you know, we, you know, our founders who do that the best or sort of like a combination of written updates, and some form of a quarterly communication to sort of give a status update and ask for help where required.

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Mat Vogels (49:03)

That's incredible answer. Last question, what is, what are some of the stakes that you see founders make immediately after they fundraise? A lot of times it's the first money that they've seen, maybe ever, certainly this amount of money. What are some of the mistakes that they find? Yep. Yep.

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Larsen Jensen (49:15)

They go fucking spend it. They go spend it all. That's the biggest mistake. They spend it all.

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So like that's that's the biggest mistake. Don't do that please. But you know obviously you know I think the best thing you could do is like you fundraise on an operating plan for some period of time based you know to catalyze your success of financing route. And so I think as long as you operate you know in conjunction with that high level operating plan it's not going to be perfect. It's not going to be nuts ass. It's going to be it's going to be different. So that's fine.

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But as long as you're doing that and just keeping investors informed when you have a critical unlock or a setback say, like, I'm to need more money for this next unlock. And at least people sort of like, you know, I've heard it a few times. It's not a surprise. Everyone hates surprises, you know, unless they're like insanely good surprises, then everybody loves them. But in early stage company buildings, those are anomalous. So the biggest problem is like, you you raise some money, we never hear from you again, and you spend it all and the company dies. That's that's bad.

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Mat Vogels (50:12)

That is it. Larsen, this was awesome. Thank you so much. There was a lot of information packed into here. We're gonna try to pull some of these out and extract them as best we can. Thank you so much for being on. Any last places where people can follow you, find you, learn more about you?

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Larsen Jensen (50:26)

I'm pretty active on LinkedIn trying to be active on X so you can find me more on LinkedIn these days. So everyone has our growth areas and no one's perfect. So I have plenty of growth areas. So you can find me on our on our website harpoon.vc also black flag.vc you can find me on my LinkedIn Larsen Jensen. Find me on X Larsen Jensen USA. But I'm building that over time. So really appreciate you have me on and allow me to chat for a while.

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Mat Vogels (50:29)

Yeah, we're trying.

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There you go. Yeah.

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Yep, appreciate it. Thanks, Larsen.

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Larsen Jensen (50:52)

brother good seeing you