Nathaniel Harding, Managing Partner of Cortado Ventures, discusses venture capital and investing in the mid-continent region. He emphasizes the importance of personal relationships and proximity in the investment process, especially for founders outside of traditional tech hubs. He also discusses the challenges of raising capital and the criteria they look for in potential investments.

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πŸ“ŒTALKING POINTS

06:39 Creating Opportunities in Underserved Markets

12:24 Investment Criteria and Value-Add

26:53 Stacking the Deck for Success

36:36 The Challenges and Rewards of Being a VC

πŸ”—CONNECT WITH NATHANIEL

πŸ”—CONNECT WITH TOM

Tom Finn (00:01.578)

Welcome, welcome to the show, my friends. We are learning today from Nathaniel Harding. Nathaniel, welcome to the show.

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Nathaniel Harding (00:08.79)

Thanks Tom, thanks for having me.

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Tom Finn (00:10.538)

Well, thank you for joining us today. I can't wait to dive into all things venture capital. If you don't know Nathaniel, let me take a moment and introduce you to this fine upstanding gentleman who is the managing partner of Cortado Ventures. It's an early stage VC firm investing in growth driven technology companies. He's an accomplished senior executive, he's an entrepreneur, he's a technologist, a thought leader, and certainly an advocate for his local community and we'll get to that he has been named the Young Global Leader by World Economic Forum and most admired CEO in Oklahoma by the journal Record. And he's a force in the realms of technology, innovation, startups, angel investing, all of those fabulous things. So let's get right to it. Let's talk all things venture capital today. How do you look at the world of investing and specifically where on the map do you put your money?

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Nathaniel Harding (01:07.958)

Yeah, great question. So I'm in Oklahoma and really we look at it as investors is how do you create alpha? Like what is your edge? And so for us, we focus on a region that we call the mid continent which is where it sounds like it's the middle of the continent, but imagine, Texas, Arkansas, Oklahoma, Kansas, Missouri, Colorado, New Mexico. That's the area that we believe is overlooked by some of our venture capital peers. But it's also an area where me and my co-founders built our company. So before we were investors, we were operators. We know these sectors, we know this geography. To create Alpha, our edge is to focus on the mid-continent and really investing in overlooked areas and overlooked founders as well.

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Tom Finn (01:54.71)

Yeah, so if people don't speak VC, what does to create alpha mean?

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Nathaniel Harding (02:01.09)

So being able to generate risk adjusted returns, right? So investing in early stage companies has a higher risk than stocks and bonds, you know, so you, an investor would want to see a higher level of return. But also, you know, not having just a correlation, not just tracking with the general market, right? When everything else is up, you're up, and everything else is down, you're down. So generating alpha is about having your risk appropriate levels of high return and that are really just kind of independent of the general market.

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Tom Finn (02:37.982)

Okay, beautiful. So if I'm in the middle of the country and I'm looking to raise capital, what is different about being in the middle of the country than being in the Bay area, in New York, Boston, maybe Chicago a little bit, uh, Austin. I mean, we got some VC guys in Austin now. Um, what, what's different about being sort of in the middle of the country, but versus being in one of these big capitalized cities.

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Nathaniel Harding (03:02.354)

Yeah, raising capital is hard no matter where you are. But I think anybody that's outside of those traditional tech hubs would tell you it's even harder to raise. And so especially early on when you're starting a company and you're really trying to sell a vision and don't have just years of track record to show for having that local connection, proximity still matters. Even in a post-COVID world, proximity still matters. Personal relationships still matter. And so if somebody is building a company, starting a tech company in the mid-continent or outside of these traditional tech hubs, it's really hard to get those first yeses. And many people either will then give up, go back to their day job, or have to move, and then maybe they're moving outside of the market that they want to serve. And that's really what we've seen, and even when I was an entrepreneur and an operator myself, witness and experience the same thing.

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Tom Finn (04:04.014)

Cool. So do you invest your own capital or do you just use outside capital to invest in startups?

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Nathaniel Harding (04:12.758)

Both. And so we as the general partners invest alongside our limited partners into the fund, actually pretty substantially. So about 10% of the fund. And, you know, we want to eat our own cooking. We believe in what we're doing. We believe it's the best opportunity for wealth creation. And so that's where we invest alongside the dozens of investors that we have from all over the country.

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Tom Finn (04:39.822)

So there's two sides to venture capital, and you sit kind of right in the middle. You have to go raise the money first from other people, and create a fund. And then you have to invest it wisely with a estimated return on investment for those folks to actually give you the money in the first place. So when you're doing your first raise, you personally, for capital to go invest in startups in the mid-continent, how do you sell that to an investor? I need X amount of money and I hope I can get you this kind of return. How do you do that?

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Nathaniel Harding (05:15.518)

Right, because I'm just like somebody who's starting a company that doesn't have revenue yet. If you're a VC that doesn't have a track record of returns, what do you do? And so I, for Fund One, along with my partners, we leverage our personal connections in the immediate geography, people that we personally knew as well as like family offices, institutional investors. So very much network and personal connection driven. But then as far as what we're saying to them, some of it is, look, you know me, you know nobody's gonna work harder at this. But also something that I think is, whenever somebody's raising money, if you can always answer these three essential questions, why this, why this idea? Why you or why me, why am I the one to do it and why now? And so for us, it was a matter of saying, look, this region is very underfunded, undercapitalized relative to the amount of opportunity. And so especially when we're talking to entrepreneurs and business owners, they get that. They're like, hey, I'm an operator, I'm an entrepreneur. We have good ideas, we have talent. But there's no capital here in investing in it. So they get that, you know, that there's a gap. And whenever there's a gap, if you're in a position to do something about it, that's a business right there. You know, why us, why me to do this? We answered that question again of, you know I'm not a flight risk, you know, born and bred here, I've been all over the world, but this is where I always call home. I've built companies here, you know, I believe in it. We're gonna leverage that know-how on how to build companies. We're gonna leverage our know-how in these sectors to help the companies. And then why now? This was, our first fund was in 2020. So the world was falling apart. And you know, there was, there's this general recognition that a lot of the incumbent companies, uh, were, were going to be disrupted that technology was going to win and you want to be on the, on the winning side. And so invest in VC and yet you actually see, look back at the data. A lot of VC funds were, were raised in, in 2020 because the general feel, but it was even more pronounced here because in this region, there's kind of a, we feel like we're behind in tech innovation, yet we have amazing talent and ideas being applied to these legacy industries. So that was the why now is the world's getting shaken up. There's going to be winners on the tech side and get behind it. So that was our approach as we were doing the storytelling, frankly, of raising capital.

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Tom Finn (07:57.386)

Yeah, wonderful. So in that first round of raise and your first fund, did you hit your economic targets that you and your partners set out to raise?

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Nathaniel Harding (08:07.146)

Yes, so we targeted raising $10 million. We ended up raising $20 million, which in the global scale of VC is a small fund, but it was an unbelievably massive fund by the scale in this nascent market in which we operate. And then we had several things that we kind of told our LPs that we're going to shoot for in terms of performance. You can look at things early in a life's fund, a fund's life, you see unrealized IRR, unrealized gains or multiple invested capital. We've hit or exceeded those targets. We look for graduation rates. That's where a startup, you know, hits that next milestone, starts earning revenue, then earns a subsequent investment. So that's kind of the graduation rate. The other side of that is the loss ratio. So we laid out early on here, our goals that we wanna hit, and we've been hitting that. And so we were able to raise fund two. So over the last 18 months, we raised a second fund that was $80 million. So remember how I said in 2020, everybody could raise VC fund, that's exaggeration, but a lot of people could raise a VC fund came out last week with data showing that of that group, only 12% raised a second fund. So we're in that 12% and our second fund was four times as large. And that's put us in very, very small company. So that's kind of how it started and that's where we are now, but building on being able to deliver what we said. And not everything's gone right. And we were the first ones to tell our investors when things aren't going right. And that's how you build trust, and that's how we're able to then earn an investment in the second fund from the same people and new people as well, new institutions as well.

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Tom Finn (09:54.082)

Well, look, that's a huge feat, man. Congratulations to you and your team. I mean, going from a $20 million round when you're trying to pick up 10 and you get 20, and then raising your second round of capital and getting to 80 million is not to be sneezed at. That took a lot of hard work and effort and elbow grease. So, congratulations to you all. I guess where this kind of leads me is, so we got all this money, that's good. And now we got to deploy capital. So we know that we want to be in the center of the country. We know that we're loyal to these markets in particular. However, how do you go about picking folks that you want to invest in or? What's your process for analyzing whether it's a seed or an A or a B? How do you look at the rounds? How do you look at the market and what are you looking for?

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Nathaniel Harding (10:49.71)

So we've looked at about 3,000 companies since we started and have invested in about 40. So it's a numbers game for sure. It's any VC that's doing it right would tell you that only about 1 or 2% of investments materialize.

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Our process is we try to be very public about what we look for, so that kind of the top of the filter is high quality. So for us, seed stage is our core, which is a product is built, but no commercial revenue yet or early commercial revenue, not enough to really extrapolate. We'll do some pre-seed, so kind of pilot stage, and we'll do some early series A but that's our sweet spot stage. Then the next filter is B2B. Where my partners and I built our companies, it's all B2B industries generally. And so we know how corporations think. And if they are the customers of our tech companies, then that's the market that we can understand. We understand how to think about ROI.

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And then several sectors that fit within our strategy includes energy, logistics, advanced manufacturing, as well as biotech, like life sciences, um, and bio-pharma. And so areas where we have, again, operating experience and when we feel like we can add value. So another criteria is can we be, can we help give this company an unfair advantage? Like, do we have a network and know how that's relevant? And we can connect this company with customers or channel partners, what can we do to be helpful when needed? And then really after we've kind of answered the questions of like just the filtering of criteria, then it's the big three. It's the team, the product and the market. So can we figure out if the market is there? Like, is there enough, are there enough people that care to pay for this? To build a market. And it's OK if maybe the first application or the first beachhead market is very niche, as long as we can see a pathway to be able to scale that by going to adjacent geographies or adjacent customer personas. So really be able to see that. But then also on the product side, is it breakthrough technology? That is 10 times better than anything else being commonly used. Is it novel, protected, or technology that is the intellectual output of that founder? But honestly, the most important, that's why I go in this order, is the team, and the founder or founders. Because in the early stages of company building, Plan A is not gonna happen, right? You're gonna get down, you're gonna work your way down the alphabet. And so seeing the resilience, creativity, resourcefulness, honesty to self and others, all of those are important attributes for a successful founder. And that comes from all walks of life. And so that's a big part of what we look for. Having relevant experience in that industry that they're disrupting is definitely helpful. And being able to recruit talent and capital and customers, essential. So that team is what we spend the most time on, but yet it's the least quantifiable. And that's where we believe that us having a background as founders that has successful exits, we can help divine that insight of does this founding team have what it takes?

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Tom Finn (14:46.35)

And I think that's so hard for founders on the other side. Hey, does the team have the chops to make this happen? How do you actually get under the hood and figure that out? And here's what I mean, Nathaniel. So let's, let's be straightforward when it comes to VC conversations, you, you end up with an analyst first, if you're on the, if you're trying to raise funds, you, you end up getting positioned to a partnership meeting, they take your company into a partnership meeting. They say, hey, there's this company, here's the founder, here's the profile, here's how much revenue they have. And then the partner sit around and either kill it or say, oh, we'll have a conversation, right? And most deals get killed in that exact moment, right? Where there's some analyst who, by the way, is 24 years old, probably went to Harvard or Stanford or some elite school, probably has very wealthy parents. And at times as the founder and by the way, I am one it can feel like this the the deck is stacked against you if I could just have a conversation with The the leadership the actual managing partners. They'd see that we have something different. How do you get past that step as a founder?

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Nathaniel Harding (15:59.65)

Um, you know, we'll involve a partner relatively early, right? And so, um, cause we, you know, we don't want to see happen is all this work done. You know, cause our side of that is we don't want to see all this work done by analyst and then it'd be for nothing, right? We don't want to see several weeks or months of work be done and then it just gets killed or something that could have been found out much earlier. So for the things that are a no, we want it to be a quick no. And I think that's everybody's interest, even though it's less good of an answer as yes, at least getting a quick no if somebody can move on. I know I appreciate that when I'm raising capital. But we typically have our partners get involved fairly early. And it's not like we're in there in the spreadsheets helping to put together the internal memo, meeting the founder. And so that's, I think, an important attribute. But also interestingly, sometimes the diligence process, yes, of course it's about what it's about, which is we want to look at your financials, we want to look at kind of legal to date, or your documents, your cap table. We want to talk to any customers, all the things that you're supposed to do in diligence. But seeing how that founder conducts themselves through that is it's almost like that's the other half of the diligence. Not that there's any make work, we're only looking for things that we need to know as part of our analysis, but then how is that founder interacting? And then hopefully they're looking at us the same way too. It's like, if somebody's going through a process with us and looking how we conduct ourselves, then that founder should be asking themselves, do I wanna be a part of this for the next five to 10 years? Maybe how long you're on somebody's cap table, and part of their company. But yes, being, to the other point of that is, the fact that we invest locally, it covers an area that's about a population of about 50 million, seven states, so I say locally, it's bigger than a lot of countries. But the fact that we do focus regionally in the mid-continent means that we, in many cases, do have visibility into that founder. So we can start to have that connection as opposed to just having an analyst kind of work in a black box, the partners never meet and then kill it in a private meeting. And so it makes me just kind of think, I'm glad that we do focus regionally just because we can have better visibility on the founders personally.

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Tom Finn (18:44.654)

So let's touch on that personal relationship piece because I think you've brought it up a couple of times. I think we need to kind of hit this nail on the head here. So how much of your invested capital goes to people you perhaps knew before or were a third party connection, sort of connection through a connection or one of your limited partners knows the firm. Like, is it that socialized for you all that it's like, hey, we know so and so and so and so let's talk to them and they've got an advantage because we we have some information. They're good people or or they're great business minds or whatever.

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Nathaniel Harding (19:22.462)

Yeah, as opposed to it would be unlikely for us to get like a cold inbound from somebody out of our market. Now, if we get a cold inbound from somebody in our market or in one of our sectors, then we're going to make an effort as the process goes on to have, again, one of the partners or our principal meet that person. So it's not that somebody has to be referred. I mean that helps me all the data out there will show you that, you know, if you have a warm introduction, a referral that absolutely helps. But even in the cases where it is cold inbound, um, you know, there's, there's an effort made to, you know, again, if the criteria are met. So I guess for us, the part of the, the role of the analyst is to all that criteria, that's like knowable and objective. That's where the analyst can say, yes, no, yes, no.

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And then it's like, okay, let's meet. So I would say, yes, there are lots of examples where a company comes to us through a connection. But let me expand more on that. We have about 100 investors, many of whom are CEOs in the sectors in which we invest. So we do get referrals from them, which is great because that means that they love that technology as a customer, so that's a good start. We get referrals, we've partnered with several groups and helped in some cases start the first of its kind incubator, adventure studio, accelerator. So those are also sources of DealFlow. So it's not so much just like a friend connection, but it was more let's establish a program to attract the kind of talent that we want to see, and then watch them go through the program. So that way we can have higher conviction on the end of it. So that's maybe another example where we're creating a community, we're creating this ecosystem where we can have more of these intersections. So there are, even if it's not just like a warm handoff from somebody, we get to see somebody in action before they're pitching.

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Tom Finn (21:33.102)

So can we talk about that for a little bit, sort of incubator, venture studio models? Can you talk a little bit about what those are and how they get used? And very effective for the entrepreneur, also very effective for the investor groups. So can you talk about that?

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Nathaniel Harding (21:49.358)

Absolutely. So a venture studio is probably where I'll start. So that's really, there's different models, but they're mostly around the idea of building a technology first. So identifying a problem in the market and then building the tech solution to solve that, and then building a company around it. And then the owners of the venture studio will then have an ownership in that company that spins out of the studio, as well as the CEO that they recruited to run it. And so 19 days is our partner. And so we were an early backer and partner of 19 days out of Tulsa. And they have that model that I just described. Which is great, because we'll have some of our own LPs that'll help contribute during their kind of exploration phase of identifying a unique problem that they can address. So that's a Vich Studio model. And actually, we have some interesting kind of wins out of that. In fact, because we also work with a developer, a dev shop called GitWit. That's also the dev shop behind 19 Days. One of our own LPs was inspired by a presentation by this group at our annual meeting, and then had an idea to develop a technology product with, you know, in collaboration with GitWit in 19 Days. They developed it and he launched the company and it's now one of our fastest growing companies in the whole portfolio. So that's a that's truly kind of ground up, you know, VC of going from. You know, being inspired to create a new product in the business, you know, which you operate building it, launching a company and then we back it.

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Tom Finn (23:18.414)

Wow.

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Nathaniel Harding (23:42.45)

So that's a venture studio model on the accelerator model. So generator, in fact, anew release just went out today. Generator is a nationally ranked accelerator program that will have different cohorts all over the country. They have dozens of cohorts. They focus on areas outside of traditional hubs, so they're well aligned with us and our thinking. And they've really perfected the model of attracting talent and companies and then having essentially like what amounts to a 12 week boot camp to go from an early idea stage to an investment ready company. And so they'll go through this program with Generator and we're partners with them. They're co-located with us down the hall as part of this incubator, which is the last thing. An incubator is really a place that houses different services and where companies can co-locate and have what should be affordable office space and access to services like an accountant and an attorney. And you know, just, you know, mentor programs and things that can help them as needed, but also just be around other founders. Because a lot of times like the best help that a founder gets is just from another founder who's like going through something in real time or somebody who's like a near peer who maybe just has that next step of experience and can then share that with a new founder. So we're here located in The Verge and so The Verge is Oklahoma City's entrepreneurship hub that houses all these different services. So for us as an investor it puts us in a great position physically and figuratively.

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Tom Finn (25:23.534)

Yeah, those are really nice models that get accentuated for the entire market. You know, I love this sort of phrase, a raising tide lifts all boats. And I feel like whether it's the accelerator or the incubator or the venture studio, you're trying to lift all the boats, right? By working together collaboratively kind of across the different segments to bring everybody together to create some really cool stuff. Right. I mean, that's really at the end of it, what we're trying to do. And for as an investor. You are trying to stack the deck. There is no doubt about it. You are trying to stack the deck where you know you're going to win. When you make that investment, that's what every VC firm wants to do is stack the deck, whether it's proven out, we've proven the technology works, or we have relationships that can support in a channel partnership way, or we have a network of folks that'll be able to help deploy the product, whatever it is. Um, we're trying to stack the deck as VCs so that our fund wins. And we can raise more capital and we can do it again and we can invest more, right? Isn't that the, the playbook here?

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Nathaniel Harding (26:25.098)

Yeah, that's right. Yeah, we want to have a scalable process, just like with companies we invest in, we want to see a scalable process, but we want to see a scalable process that we can repeat across multiple fund vintages. And especially when you're an early-stage investor, you got to create your own opportunities or you have to find ways to be the center of gravity for the sorts of opportunities that you want to be exposed to.

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Tom Finn (26:53.006)

Yeah. So I've raised capital a couple of times and I've had a lot of VC conversations. And one of the things that always has driven me nuts is when I get on with an analyst and they say this, Nathaniel. So I want to know if your analysts do this. Do they start with our ethos is X or our ethos? It's my least favorite way to start a conversation. But do you guys play with the ethos conversation with all of your...

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Nathaniel Harding (27:23.978)

I don't think, I don't know if that word's ever been thrown around here. You know, hopefully the way, at least the way that we've passed on how it, how it should be done is we do like to say just what we do. A we're a seed investor, you know, B2B, these sectors, these check sizes, these rounds, because we don't want it to be like a gotcha with the founder of like they do their whole pitch and they were like, Oh no, we don't do that at all. So, or, you know, the, the founder is like, thinking like, well, hey, I may do a million dollar round or I may do a $5 million round. I may call it C or call it A. Again, if a founder is still kind of like playing around with what they wanna do, like I wanna tell them what we wanna see. And then if they wanna help that conversation go well, then they can like pick that. You know, like if I say, I love doing average, you know, million dollar first check. And then that gives them a chance to be like, we're actually looking for a million dollars. Like, great. So I wanna like set things up to help just give easy wins so we can talk about the harder stuff about like how big is that market and will support this technology, all that.

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Tom Finn (28:29.774)

Yeah. So for those of you listening, that is really kind of Nathaniel to do that. Most VCs do not do that. They'll tell you kind of where they play in generalities. They'll tell you their average check size. They'll tell you the markets that they play in to some degree. But they won't, they won't tell you that you've overvalued your company. They won't tell you that your valuation is unrealistic. They won't tell you that they would never invest at that valuation, right?

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Nathaniel Harding (28:35.379)

Yeah.

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Tom Finn (28:57.422)

So you got to that, that part of the game, I've never really understood, um, the valuation piece because founders always overinflate and it's the VC's job to bring you back to reality, but I feel like it should be a conversation. And what, what I've seen and heard from other founders is if you go in with the wrong valuation, when you're having that conversation, the VC just goes, Oh no, valuations too high, let's move on. What, why do you guys do that? And it might not be you, Nathaniel. But as an industry generically, I know I'm speaking generically, but why do you and your peers, why do you guys have this sense of, oh, they got the evaluation wrong, let's move on.

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Nathaniel Harding (29:34.354)

Yeah, I mean, sometimes it may be, it could be laziness, frankly. And, you know, I'm not here saying that I've never been lazy. I always work hard. But it's kind of the human nature of, you know, fancy people call them your heuristics, right? Like shortcut mental models that you can use to wade through a bunch of stuff. So if you're given the task of looking at a thousand deals a year thinking really, really hard about all 1000 of them is not plausible. So a heuristic would be, how can I like not think hard at all about like 800 of them and then think hard about 200 of them. But there's also like, let's maybe do that in a way that honors the other person's time. And if you are like missing on like valuation or something that's negotiable, then let's negotiate. And maybe it kind of makes me wonder, how do, yeah, I take pitch calls too, by the way. It's not just the analyst or associate or principal. Everybody on the investment team takes pitch meetings. It depends on what the sector is and the stage and all that. But, you know, for me, it opens up a negotiation. I wonder, I'm wondering aloud if maybe a more junior person like doesn't feel deputized to like negotiate, you know? So even if they're not just being lazy, but if the founder says, is it, you know, $10 million valuation, then maybe there's some wisdom or just transparency to be able to say like, I think that's not a good value. If you really want to be competitive, it should be this,Β  or if it maybe would come across as like calling somebody's baby ugly, you know, it's like, uh, no, your company's not worth that much. So I do think there is like a proper way to address those things. We, I have, we, Cortana have many examples where we were able to give feedback on where we thought the valuation should be, where it was. And there's been times where the founders like it's already set, you know, the terms are set or just my mind's made up. And like, that's cool. And actually one time that happened. And then a year later they came back and our world and their world kind of met and they came back and we invested. And so like their expectations came down and the market came down. And so you can tell somebody the baby is ugly in a humane enough way to where they won't hate you and they'll come back. And if you're professional about it, and if you give rationale, you're not just being negative, you're giving rationale about where the market is that everybody just wants to be treated with respect. And so I think there's a piece of that we need to make sure is imbued across the whole organization and even the people that are more junior that may not feel kind of empowered to do that.

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Tom Finn (32:24.366)

So you sat on the founder side, you've sat on the VC side. Which side of the table fits your personality more?

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Nathaniel Harding (32:35.17)

Definitely VC. I love the idea of, I mean, I loved it when I was a founder and president and all the things. Because you feel like you're really creating something from the ground up. Like, brain birds is a new thing and people are willing to pay for it. Like, I'm making the world go round, all that, which is true. And they do make the world go round and we're all trying to ride on their coattails. But for me personally, my skill set is more the art of the start and like helping build a coalition uh around new ideas and but then like doing to the next one right i'm an idea guy you know uh or as opposed to like a product person so i'd rather um be the one that can help again build that coalition or you know build that in this case build a quartado, building a machine that just spits out new companies, right? So then I can be a part of amazing new companies all the time, my favorite part. And once a company gets into an operating mode, you know, like into cashflow positive, like kind of rinse, repeat, stable, that's when I'm like, what's the next one? You know, I'm ready for the next one. When do we do that? Other people are like, great. I want to. I want to be stable and do that for forever.

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Tom Finn (34:04.302)

Yeah, it's a very different game, right? And you do find a handful of folks that were operators that have started their own funds like you, Nathaniel. And, um, I always love when I find VCs that are that way, because they really do understand it, not just because they read about it, uh, at Harvard business school, but because they've actually lived the grind and the day in and the day out kind of work, which probably makes you a more effective speaker when you're speaking to raise money to these, to these folks um, that are in the mid continent that say, Hey, you've done it, bud. Like. And you can see the forest through the trees and you know, the BS to avoid. So, you know, here's a million bucks, go invest it. I mean, that's, that's a wonderful spot to be in. Um, hardest thing about being a VC. What's, what's the hardest day, uh, look like for you.

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Nathaniel Harding (34:49.51)

I mean, it's, it's the amount of community, like just a share volume of communication, cause again, you know, you're looking at a lot of companies, you have a lot of stakeholders, all of our companies have customers. And so the, the sheer volume of just communication and making sure that you're being responsive. Um, and because you do have a lot of companies, you know, there's days where like a bunch of like a bunch of good news rolls in and it's like, this is the best thing ever. There's also days just by this numbers game where a bunch of bad news rolls in, like all in a one or two day period. You're like, I was coming from everywhere. Like everybody's out to get me. And, but you know, that's when I remind myself that like, I remember what it felt like as an operator to have a bad day. And like that's like existential level bad. Where, you know, so whenever I'm hearing that many of our companies are having a bad day. I have a ton of empathy and, and I, you know, have, I guess, thankful in a way where it's like, now I get to be on, on this side. And the people that are in the trenches building it, like the ups are really high and the downs are really low, but yeah, there's definitely that empathy there. But yeah, the hardest part is all the different stakeholders, you know, the investors, you know, policymakers, the founders, the customers of the portfolio companies. But I thrive off that. But you know, it's like when you're operating at your optimal level, you know, you're running hot and sometimes you can overdo it, overcommit, push yourself too hard. And that's where you have to really, I have to remind myself often to focus on what we do best, what I do best. And… And so that's, I think, a really challenging part of what we do. But any good business, you got to focus on your unique value adder. The thing you can do better than anybody else.

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Tom Finn (36:50.734)

Yeah, it sounds like you've really built a nice company for yourself. Again, congratulations. That's awesome. But it sounds like you're really introspective about the way that you approach the business, which I think is just a wonderful sign of growth for all of us, right, that we're looking at things a little differently and trying to do the right thing and trying to grow it the right way, and you're doing all of that for the mid-consumption, which is awesome, man. So I'm really, really happy to hear that that type of investment is going into the center of the country where there are great people, talented people, wonderful businesses that can grow to be wonderful enterprises if they choose to do such a thing. So if somebody's looking at Cortado Ventures and they want to put their best foot forward with you all and your team, give us one phrase, one idea, one thing that you want all founders to come to you with, whether it's be prepared or be kind or what, like what does that feel like when you all are sitting around?

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Nathaniel Harding (37:48.362)

Yeah, I think if somebody just does a quick review of our website, cortado.ventures, and then is able to answer in the affirmative all the things that we're looking for, and then come in with, why this, why me, why now? So first of establishing that you can kind of fit within the boxes that we check and then answer those three questions. That's a great way to have like a, you know, a positive interaction or interaction that has a better potential to be mutually beneficial, right? So, but yeah, we're easy to hold of Cortado.Ventures. Some people, we even have a place where somebody could input information on our website as far as their company attributes and it'll schedule a meeting or they'll get feedback about where it's not a fit. But all these things try to make it really low barrier.

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Tom Finn (38:41.55)

Yeah, beautiful. Well, thank you for being on the podcast, Nathaniel. Great to connect with you on your fund, uh, on the work that you're doing in the mid continent. Really love the work you guys are doing. I think it's awesome. Uh, so, so kudos to your whole team, including your investors that are so important in this process. And we never spent enough time talking about the investors, but thank you to those wonderful folks as well that make the, uh, the world go round. Thanks for being on the show.

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Nathaniel Harding (39:03.786)

Thanks, Tom.

Tom Finn
Podcaster & Co-Founder

Tom Finn (he/him) is an InsurTech strategist, host of the Talent Empowerment podcast, and co-founder and CEO of an inclusive people development platform.

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