From Infrastructure to Investment Edge: Cycles, Conviction, and the Next Era of Digital Assets | Courtney Olujobi, Moon Pursuit Capital

[00:00:04] [SPEAKER_01] This is the Crypto Hipster Podcast. This is not a traditional interview show. These are perspective-driven conversations with founders, builders, and independent creators shaping what comes next.

[00:00:26] [SPEAKER_01] We go beyond headlines, beyond hype, and beyond price to explore ownership, freedom, and opportunity in the digital economy where builders talk freedom, not price. Hello and welcome back to the Crypto Hipster Podcast. This is your host, Jamil Hasan.

[00:00:54] [SPEAKER_01] And today I'm joined by Courtney Olujobi, who is the Principal of Portfolio and Investment Strategy at Moon Pursuit Capital. Courtney's path into digital assets is an interesting one because it crosses enterprise technology, infrastructure, private capital, emerging tech,

[00:01:16] [SPEAKER_01] and ultimately crypto investing. At Moon Pursuit, he now helps think about portfolio construction and investment strategy across the market that has spent much of its history being driven by narratives, cycles, and speculation. Now, I don't want to spend today's conversation predicting where Bitcoin will be next month. No one knows where it'll be tomorrow.

[00:01:42] [SPEAKER_01] I want to talk about something harder, which is judgment. How do you allocate capital when narratives move faster than fundamentals? How do institutional investors distinguish between technological transformation from investment opportunities? And how do you manage risk as an asset class where uncertainty is not an exception, it's part of the architecture? Courtney, welcome to Crypto Hipster.

[00:02:10] [SPEAKER_00] Thank you, Jamil. Great to be on.

[00:02:13] [SPEAKER_01] You're very welcome. So, you spent years around enterprise technology and infrastructure. How did someone from the world of that technology and infrastructure end up allocating capital to digital assets?

[00:02:28] [SPEAKER_00] Mm-hmm. Yeah. So, if you look at my background, it may help kind of level set. My technology journey started roughly 2013. Actually, previously about 2011. I ended up joining a VAR, which is a value-added reseller.

[00:02:57] [SPEAKER_00] One of the largest VARs in the US focused on all technology needs for enterprise clients. And I was also heavily focused in the data center space. So, I would work with these Fortune 500 companies to help them acquire their technology needs. And it was across all technology buckets.

[00:03:27] [SPEAKER_00] So, if you think about servers, energy, if you think about power, route switch, networking, heavily focused on the data center. And that was across the US. And there's really an underlying theme when it comes to technology and many aspects of, you know, how we live.

[00:03:55] [SPEAKER_00] So, and that is core to edge. So, if you look at historically, companies would house their data center needs within their regional or local office. And then you saw a progression where things move from core to edge. Things like edge compute.

[00:04:22] [SPEAKER_00] There was a shift in larger entities like your Amazon's. Now would be your Facebook, your Microsoft's creating these very large data centers. And then the companies now moving their compute needs from edge to core. Well, this track line you can see in several different industries.

[00:04:51] [SPEAKER_00] And I was fortunate to win a contract to build a data center for a UK-based contractor. And the director at that time mentioned, hey, you know, can we leverage what we're doing here so I can get some additional servers because I'm interested in mining Bitcoin. And that was back in 2016.

[00:05:21] [SPEAKER_00] And knowing that things kind of followed the cycle right core to edge, I began looking into crypto and what was happening from a decentralization of monetary policy.

[00:05:40] [SPEAKER_00] And also a shift from, call it government-based currencies to a currency that wasn't necessarily controlled. Now, some may argue in some case there is a centralization because you have sort of large holders. But for all intents and purposes, it can't be controlled by one single entity.

[00:06:10] [SPEAKER_00] So then I began my kind of crypto journey in 2017. Very much school of hard knocks. Hey, let's see, you know, what happens with this coin. I was buying Bitcoin at that time. And I've gone through every cycle from, you know, the ICOs to NFTs.

[00:06:36] [SPEAKER_00] And now, obviously, we're running a fund where we're doing more kind of institutional diligence of founders and their teams. And then we've made investments that we think will do really well for us.

[00:06:55] [SPEAKER_01] Excellent. So I don't think I've talked to anybody yet who has your background as far as edge compute. So what does that background teach you that a lot of crypto native investors don't understand?

[00:07:12] [SPEAKER_00] Yeah, I'd say, again, that everything is cyclical, right? So when you're looking at how you transact, right? You know, even, I guess, I'll equate it to this, right?

[00:07:37] [SPEAKER_00] With a lot of folks that, you know, you could see this track line in other industries. And I'm going to tie it to what we're doing today. So, you know, the media industry, for example, is very centralized. You have folks that are doing movies. You have folks that are creating news in a centralized way, right?

[00:08:05] [SPEAKER_00] There's not a lot of variations in the channels that you could watch going back in time. Now you have things like YouTube, which give access to folks, right? But this is also at the edge.

[00:08:25] [SPEAKER_00] So the core example would be previously a limited amount of media channels and news channels, whereas now we have access and we've empowered people at the edge to create their own media. So, again, if you're looking at any industry, you would try to judge where we are in that cycle.

[00:08:54] [SPEAKER_00] This is also in medicine, right?

[00:08:58] [SPEAKER_00] There's parallels across every industry where if you can see, hey, this particular service or this experience or this offer is very core based with a limited amount of people that are doing it to, hey, now this is very edge based.

[00:09:25] [SPEAKER_00] Where, you know, I'm looking outside for my services or I'm going outside for my services or I have way more opportunities to, in this case, transact that are available to me.

[00:09:46] [SPEAKER_01] And you could do the same thing with portfolio construction, obviously.

[00:09:49] [SPEAKER_00] Yeah, absolutely. Yeah.

[00:09:52] [SPEAKER_01] So what's the difference between, you know, believing a technology will change the world and believing it's just a good investment?

[00:10:03] [SPEAKER_00] I think the two are, you know, largely different, right? So we can look at a technology and see that, hey, this technology is going to improve my way of life, right? That judgment can be made pretty quickly.

[00:10:23] [SPEAKER_00] Also, if we look at things like AI, if we look at things like what Google search was able to do for us, and now the progression that in addition to a better search, now we're able to get additional information, right?

[00:10:44] [SPEAKER_00] So AI is enabled, endless research, referenceable, you know, with an idea. You can pretty much create MVP or, you know, what you think this technology should look like.

[00:11:04] [SPEAKER_00] So that is very different than, hey, is this company the right fit to, you know, ensure that their technology is going to work? They have a moat. It's the team that's going to survive. They're able to raise enough capital. There's product market fit.

[00:11:29] [SPEAKER_00] So there's, you know, customers on the other side that are interested in this. So this is very different. So globe, like if you look in larger scale, right, every company plays a part. So people are talking about AI bubbles or, you know, website bubble, the website bubble.

[00:11:55] [SPEAKER_00] So this was necessary to build and drive the infrastructure, right? If you look at, you know, the railroad companies back in the day, most of the railroad companies actually went bankrupt. But the railroads were used for several years, right? They were a necessary thing.

[00:12:20] [SPEAKER_00] So the bets that you take on different companies that are furthering this infrastructure has a multitude of markers that you're looking at de-risking that investment to see. But, you know, this is all, it's all still a risk, right?

[00:12:44] [SPEAKER_00] So, you know, you do your due diligence and then you support the teams accordingly. And then, you know, you diversify within that.

[00:12:59] [SPEAKER_01] So let's talk about your job today in the pursuit of capital. So I think one of the things that is an important aspect of running a fund is this concept of conviction versus discipline, right? So at what point does conviction become stubbornness?

[00:13:24] [SPEAKER_00] I think conviction, stubbornness, that's a good question. I mean, I guess you could be stubborn with, I don't know, maybe ask me a little bit differently. Okay. Okay.

[00:13:52] [SPEAKER_01] Let me, let me, I held onto a crypto portfolio, a crypto holding and been putting money into it since 2020. It's done nothing. And I said, okay, I'm going to go to the next level. And yesterday it went on 3x. I'm like, people, like I said, I shouldn't be doing this one anymore. And all of a sudden it just pops up. Like, okay, my stubbornness paid off.

[00:14:18] [SPEAKER_01] But like, how do you draw the line between this being, you know, holding something for the sake of holding it? Ego or something that you think is going to, you know, have true conviction in? Yeah.

[00:14:32] [SPEAKER_00] So thanks for that. Yeah. I think that, you know, if you look at historically the best traders, they've either lost their keys or lost access to their wallets or unfortunately they're dead.

[00:14:52] [SPEAKER_00] So what that means is, you know, we, I think as humans have, you know, our idea of when things should happen. But if you look at the markets, the folks that make the most money spend the longest time in those markets.

[00:15:16] [SPEAKER_00] Now, there's a number of different cryptocurrencies, but if you're looking at the grandfather, right, Bitcoin and then the top five or 10 coins from there, you are looking at, you know, something that's been around since 2009.

[00:15:39] [SPEAKER_00] So our idea that things should go up within a certain amount of time is really based on, you know, us wanting something to happen very quickly when historically the money is made, you know, over time. You know, you can't, it's, you can't time the market. It's time in markets.

[00:16:11] [SPEAKER_01] So I used to do this. I used to chase when the number is going up. Now I buy the laggers, you know, is, is selling, selling harder psychologically than buying?

[00:16:27] [SPEAKER_00] I mean, it really depends on who you ask. I mean, if you ask me, I think when folks are seeing continuous appreciation on their accounts, it becomes difficult to sell.

[00:16:51] [SPEAKER_00] And then it's even more difficult to sell when you're losing sometimes. So it, it really depends. I mean, at some point we get into the psychology of, of money, you know, which is also greed based, right?

[00:17:17] [SPEAKER_00] Which we think that, Hey, this is just gonna, this is something that's continuing to move up. And I want to stay in. But our, our life, just referencing what I said before, everything is cyclical. So it's peaks and valleys across all markets, across everything that we're involved in.

[00:17:42] [SPEAKER_01] So let's investigate that time in markets concept. So, cause the moon pursuit says your approach is using quantitative strategies, you know, designed to perform across market environments rather than just relying on markets go up, which everybody likes to say markets go up, you know?

[00:18:03] [SPEAKER_01] And so, you know, crypto was built around this, this idea, this extraordinary idea of upside mentality. So what happens when institutional investors come in and say, I don't actually want one directional risk.

[00:18:22] [SPEAKER_00] Yeah. I mean, so we are in, let me just give you some background on moon pursuit. So our fun one, we started off as directional bias. And then it was a pivot into venture, which holds, we hold about 16 portfolio companies in various stages of launching.

[00:18:52] [SPEAKER_00] And then our, our second fund, which we'll be launching by two, one of 2027 is market neutral. And that's largely based on market feedback, right? The interest around market neutral strategies that can generate alpha in, you know, any, any environment.

[00:19:22] [SPEAKER_00] So the interest is there. I think the amount of, I'll call them conflicting interest in monetary policy, fiscal policy has driven a lot of uncertainty around markets, right? There, there's no shortage of headlines in regards to what's happening with the treasury.

[00:19:57] [SPEAKER_00] So there's a lot of uncertainty that says like, Hey, if I want to make an investment, I want to invest in folks that can generate alpha in any, any environment.

[00:20:13] [SPEAKER_01] So this morning, this morning, this morning, the commodity futures trading commission proposed rules that would create a new federally regulated category of crypto asset markets, right? That's the government getting involved and more and more institutions getting involved. So with this institutionalization of crypto in the markets, make it more boring.

[00:20:41] [SPEAKER_00] I don't think it will make it more boring. You have institutional capital, you have investors, you have a number of folks that are looking for a more defined framework.

[00:21:02] [SPEAKER_00] That, you know, not only protects their capital and interest, but also serves as a guide for these early stage founders and companies. So I think, you know, we've seen continued growth. We've seen continued interest and adoption, right? For cryptocurrency.

[00:21:31] [SPEAKER_00] We've been hopeful for additional guidance coming out of clarity, but regulators have, you know, continued to provide support and also step up and say, Hey, you know, we're going to help further this industry by providing this guidance.

[00:22:24] [SPEAKER_00] Got it. Investment edge. Investment edge. Investment edge. In my opinion, comes from being on the street, you know, what's happening out there? What are the problems that folks are looking to solve? And then identifying if there's product market fit.

[00:22:48] [SPEAKER_00] So for us, one of our companies is heavily focused on a quantum wallet security, right? So we know that this is coming and how are people going to be protected? You know, the headlines are very relevant, right?

[00:23:15] [SPEAKER_00] A lot of, there's a lot of noise about AI. Now we're seeing, you know, almost the equivalent in quantum protection, quantum security. Well, the opportunity, right? It is, you know, knowing that this is coming maybe three or four years before it hits the headlines.

[00:23:43] [SPEAKER_00] And then doing your research, right? Your due diligence. Is this product viable? Is this founder thinking, you know, five, 10 years ahead? And then making a decision.

[00:24:01] [SPEAKER_00] So it's really, you know, with anything that you're involved in, you want to be close to call it the core before it hits the edge. And I think that's where the opportunity is.

[00:24:20] [SPEAKER_01] So quantum, you know, the people are saying that quantum might distract or take away some from Bitcoin. You know, the jury's out on that, right? But it is a longer term play, right? So is patience being patient? Is that itself alpha?

[00:24:44] [SPEAKER_00] I would say so. Yeah, I would say so. That's a part of it, right? Even if you look at AI, for example, AI has been around for 20 years. And if you watch a lot of the podcasts and the videos, you can hear these large entities say that, you know, we had some of these services five years ago,

[00:25:13] [SPEAKER_00] but we've been rolling them out as, you know, adoption slowly increases. So it's not that, you know, we're utilizing these tools now, but a lot of them have been created maybe 10 to 15 years ago and they're just being rolled out.

[00:25:36] [SPEAKER_00] So that conviction requires patience because, you know, you've been involved in it so long that you have no choice.

[00:25:49] [SPEAKER_00] And typically from an investment perspective, you know, I won't say a large percentage, but there is a percentage of investors that come in, you know, typically after all of the development happens.

[00:26:09] [SPEAKER_00] And then they have kind of outsized expectations on returns when it's, hey, let's look at where's the infancy of this product or this offering. And then do we have an opportunity to get in and be patient until, you know, you reap the reward?

[00:26:33] [SPEAKER_01] Yeah. I know you've argued that one of the earliest quantum opportunities might actually be protecting the infrastructure we already have, right?

[00:26:45] [SPEAKER_00] Right.

[00:26:46] [SPEAKER_01] So does crypto take the quantum threat seriously enough?

[00:26:53] [SPEAKER_00] Yeah, I'd say for sure. There's no, I don't think there's anybody that isn't taking it seriously. So there's different teams working on different parts of what the quantum security looks like as it relates to infrastructure, blockchain and wallets.

[00:27:17] [SPEAKER_00] And a significant amount of investment is going into, you know, support them. So, yeah, it's being taken seriously and we'll see how it plays out.

[00:27:32] [SPEAKER_01] Got it. So quantum is serious. AI has been slowly rolled out for five years. Digital assets are still evolving. As everything matures, right, where do you see genuine convergence? And where are people simply stapling, you know, narratives together?

[00:27:56] [SPEAKER_00] So I don't think that you can remove narrative from anything that, you know, we do, right? There's always going to be a certain narrative. What you would look at is where the conviction is.

[00:28:14] [SPEAKER_00] And things like Bitcoin, for example, you know, about 63 percent of all Bitcoin has not moved off chain in a year. 48 percent in two years and about 34 percent in the last five years. So that shows very strong conviction.

[00:28:43] [SPEAKER_00] It has been a market leader. The performance has been there. You know, price has moved significantly up since 2009. So it's really the conviction in the space now. You have increased regulatory framework. You have increased support from large government entities globally.

[00:29:14] [SPEAKER_00] So when you are looking at, you know, the industry and maturing as a whole, that's the indicator that it's here to stay. Remove the narratives and look at, you know, what's actually happening behind the scenes. That's what would be my feedback.

[00:29:40] [SPEAKER_01] So a lot of people depend on narrative. At least in the crypto culture, in the crypto community, everybody depends upon narratives. But if digital assets become an institutional asset class only, will the crypto culture disappear? And if it does, what would be missing? What should survive?

[00:30:04] [SPEAKER_00] I don't think culture ever disappears, right? Culture is established by, you know, everybody having interest in it.

[00:30:13] [SPEAKER_00] And it could be argued that crypto has, you know, crypto has like this subculture that might have really influenced the valuations on projects that, you know, weren't turned out to not be good investments.

[00:30:39] [SPEAKER_00] But as a whole, you know, this is what was necessary to establish the industry, meaning that, you know, it raised awareness. It caused growth.

[00:30:57] [SPEAKER_00] Also, if you look at traditional investment opportunities, they've been restricted to only accredited investors, for example, right? When crypto has been largely accessible to anybody who has internet access, who, you know, their IPs haven't been blocked, right?

[00:31:27] [SPEAKER_00] And I'm talking on a global scale. So when you're looking at specific investments, you, with something that is widely accessible via internet, you're going to have folks that say, hey, look at what I invested in. And I was able to make a X return, right?

[00:31:54] [SPEAKER_00] So this is also part of that, the asset class maturing. People are going to use whatever narrative they want because there's nobody saying you can't, right? So, you know, these things are all a part of the story of crypto growing. So what we're looking at is, is it still maturing?

[00:32:21] [SPEAKER_00] Is there still growth and adoption? Are there still larger entities like government agencies looking to improve the experience for investors and further de-risk those investments?

[00:32:39] [SPEAKER_01] I definitely see that happening. Yeah. So that's good. That's good. So, awesome. So let me ask you one last question. 20 years from now, say, say you and I have this conversation, I hope I'm around 20 years. But when we look back at, you know, at this period, what do you think that we'll realize where we were completely wrong about?

[00:33:12] [SPEAKER_00] I think we have to give ourselves grace. I mean, we're wrong about a lot of things, in my opinion. That is, that question is, I mean, it's a very interesting one. 20 years from now, who can predict? I know I can't. The world changes so quickly.

[00:33:42] [SPEAKER_00] It's changed quite quickly in the last, you know, year, two years. So I think as a whole, humans are very interested in connecting. And then all of these tools are, we're doing to connect us more or better.

[00:34:10] [SPEAKER_00] You know, there's a lot of interest in longevity because we want to live longer, right? We want to preserve things like our health. And then, you know, we have things that, like, we want our livelihood to improve.

[00:34:35] [SPEAKER_00] It would be nice to see that globally, right? Not just with one area. But yeah, in my opinion, there's no shortage of resources.

[00:34:54] [SPEAKER_00] And, you know, 20 years from now, my hope is that we were wrong with maybe how we treated some people. And then creating, you know, things that don't distribute or decentralize things that increase our connection and make us live longer.

[00:35:27] [SPEAKER_01] Good. I want to thank you very much for your time today. I have one last question. It's how can people find out more information about you about Moon Pursuit Capital?

[00:35:36] [SPEAKER_00] Okay. So you can follow us on, we're online, MoonPursuit.com. I'm easily found on LinkedIn, Courtney Olujobi, C-O-U-R-T-N-E-Y-O-L-U-J-O-B-I. And yeah, we're on socials as well. But yeah, we're easy to find. Awesome.

[00:36:03] [SPEAKER_01] I love speaking with you. Thank you very much for your time today.

[00:36:06] [SPEAKER_00] Thanks, Jamil. Enjoyed it.