Screaming in the Cloud - Finding Engineers with Empathy with Lili Rogowsky

Episode Date: April 15, 2025

If you believed, they put a data center on the moon. No, for real, they did, and it’s partially thanks to Lili Rogowsky, partner at Atypical Ventures. Lili joins Corey to discuss her unconv...entional leap from law to venture capital. Although she made a sharp turn career-wise, Lili remains grounded in the often heartless world of venture capital—highlighting the importance of empathy and technical prowess in founding successful enterprises. Out of all resources, time carries the heftiest price tag, and this half-hour episode is a low-risk, high-yield investment.Show Highlights(0:00) Intro(1:12) The Duckbill Group sponsor read(1:46) How Corey (kinda) met Lili(3:38) What attracted Corey to Atypical Ventures(5:58) How Atypical helped put a data center on the moon(8:34) VC “done right”(9:59) What led Lili to run a VC firm(13:43) Quitting jobs until you find something you like(16:28) The Duckbill Group sponsor read(16:54) The value of sharing your time(21:44) Risk assessment, well-dressed horses, and punching up in comedy(24:44) The importance of humility in life and business(29:15) Where you can find more from Lili and Atypical VenturesAbout Lili RogowskyLili is a dynamic investor, attorney, advisor, and entrepreneur. She is a partner at Atypical Ventures, an early-stage fund that identifies and invests in “engineers with empathy” working on plausible science fiction. A voracious reader driven by her curiosity and love of type 2 fun, Lili’s experience includes (in no particular order) mountaineering, visual arts, marine science, founding a law firm, cave/ shark diving (not necessarily at the same time), data privacy/ security, gardening, recruiting, battling NYC rats that eat her car, and interplanetary internet.LinksAtypical Ventures: atypical.vc Email Lili: lili@atypical.vc SponsorThe Duckbill Group: duckbillgroup.com

Transcript
Discussion (0)
Starting point is 00:00:00 After the tech company, I actually had my own law firm where I was helping companies from around pre-incorporation through series A. And I didn't really like taking their money because they didn't have any. That's not a great business model for a law firm, but it is for VC. So I get to now give them that money and still provide them that support and be of service. And it kind of feels like in some small way, maybe I'm helping to put that data center on the moon. Maybe I'm helping this company get past that really delicate early stage and be able to flourish. And are founders to not wanting to sound too corny, but that I really believe in, that I think are doing things that are going to set them
Starting point is 00:00:33 apart and add value in the world. I get to help them. That's a pretty cool gig. You would definitely have to pay me to stop doing it. Welcome to Screaming in the Cloud. I'm Corey Quinn. Today's guest is a little bit off of the usual beaten path of folks I talk to who are deep into the cloud space. We'll get there. Lily Rogowski is an awful lot of things. Professionally, she's a partner at Atypical Ventures and also tolerates talking to me. Lily, thanks for joining me. Thank you for having me, Corey.
Starting point is 00:01:12 This episode is sponsored in part by my day job, the Duck Bill Group. Do you have a horrifying AWS bill that can mean a lot of things? Predicting what it's going to be, determining what it should be, negotiating your next long-term contract with AWS, or just figuring out why it increasingly resembles a phone number, but nobody seems to quite know why that is. To learn more, visit DuckBillGroup.com. Remember, you can't duck the duck bill bill. And my CEO informs me, that is absolutely not our slogan. So I want to start at the beginning, but I sort of forget where that even started
Starting point is 00:01:50 because you reached out to me years ago on LinkedIn. And I forget even what it was that you said, but I get a lot of folks reaching out and I'm also bad at clearing out inboxes. But for some reason, I wound up replying to you. What did you even want back then? It's a really excellent question. The answer is I don't know.
Starting point is 00:02:08 I started working in venture and Chris, my partner at Atypical, told me I should be cold, outreaching, interesting people to build my network. And I think I ignored that advice for about a year working with him. And at some point realized how much of a value add that was going to be. I read an article about you in the New York Times and you had a picture of yourself holding a dog. I thought this is the... It was hilarious. I was like, this person is snarky and what a strange
Starting point is 00:02:37 article and what a great photo. I should reach out to him. I don't know that I had a point and I tried to hide that in my outreach to you. And I think I think the message was something along the lines of, I am kind of a venture capitalist. I think you seem interesting. Can I talk to you? And somehow it worked. I don't remember what you said, because I get those all the time. And I immediately hit the not interested button, or I just close the tab or get distracted by something shiny.
Starting point is 00:03:05 But this was years ago. We started talking. Yeah, I think it was that it was very self-deprecating. I think that that maybe was the tone that we had in common. And I think maybe that's what it was. You're definitely onto something there. I have very little patience for folks who are incredibly self-aggrandizing.
Starting point is 00:03:21 It's not polite to say, but I say it anyway, that I believe that LinkedIn is borderline a porn site because it's where people go to pleasure themselves publicly. Why does it always go there with you, Corey? You know, one wonders quite a bit. So one thing, so I've been very public about being skeptical of the entire VC world and it's odd that I spend time talking to VCs and saying nice things about them. And as of relatively recently, I'm an advisor to one of your funds, which is fun and
Starting point is 00:03:53 exciting. Yeah, we're very excited to have you and it took only I don't know years to convince you or years for me to figure out what to do with you until I realized that this was an unbelievable value add for us. So very happy to have you and thank you. What I found fascinating about the whole story is that, okay, Atypical Ventures, great. What's your investment thesis? And the answer started off with, oh yeah, we're basically doing nothing with software,
Starting point is 00:04:17 that that's not our stuff, that that's nerd shit. And it was awesome. You probably do a better story of telling me what your investment thesis is. I haven't memorized the talking points yet. Hit me with it. Well, we're gonna have to fire you as an advisor if you don't know this. So this will be, you'll now have it recorded
Starting point is 00:04:33 for you to study from. So there's a few different ways that we like to frame it. I think the typical questions are, what stage do you invest in? What sector do you invest in? What sector do you invest in? To those answers, very early stage, as early as we can find them. Can we compel them to start this company when we read their research paper?
Starting point is 00:04:53 Then we look for what we call plausible science fiction, which we can get into, and it is intentionally nebulous. But I think the more interesting part of our thesis, and I think maybe what is a little bit more out of the norm, probably from our original conversation, is we look for a very specific founder archetype, and we call that engineers with empathy. So we look for technical founders who have the hard skills to build the thing,
Starting point is 00:05:18 and then also have the soft skills to build the right people around them. This could be folks who have intellectual humility, people who are coachable, people who want to be coached, people who are capable of changing their minds. And then we spend a lot of time trying to figure out what their mental models are, understanding that what you believe today is kind of less important than how you think and how you're going to make decisions in the future.
Starting point is 00:05:42 Because what you believe today, and especially with the early stage venture, which I like to call a shared hallucination, that should and will change. So how this person thinks and the way that they build up their mental models is a really important factor, we believe, in what their future success will look like. I want to be very clear here, because the audience expects certain directions.
Starting point is 00:06:04 We operate in a bit of a bubble here. When you say engineers, people think, oh great, what's your development stack? I want to be very clear that that was my reaction when you and I first started talking of, oh, we invested engineers with empathy. It's like, okay, so they're building what? Microsoft Excel with emoji in it?
Starting point is 00:06:20 And you're like, no, we're talking data centers on the moon style stuff. And I thought you were kidding. And you weren't kidding. You actually did it. Yes, we just landed our second mission to the moon last month. So yes, we've now put a data center on the moon with another one that will be due to go up.
Starting point is 00:06:39 Insert obvious joke about AWS data transfer fees to the moon here. Well, well, Corey, fortunately, Lone Star has the spectrum rights between the Earth and the moon. So there's actually we can go down that line. But that's a that's a very, very interesting point to point, right, when you're able to drop a ground station on the Earth and speak directly to your data center on the moon. So their business model is a little bit more disaster recovery and data security. But I digress. So, yeah, when we are, unless you want to dive into that a little. No, I just want to point out that when Andy Jassy became the new CEO of Amazon, he added two additional leadership principles, both of which are bullshit. One of those bullshit leadership principles is strive to be the Earth's best employer.
Starting point is 00:07:20 So expanding to the moon is absolutely the loophole they're going for. We always need loopholes. That's very important. Thank you. The moon, we can horse whip you there. It'll be great. I'm kidding. Amazon does that anyway. And it's interesting because it is, it is a, that's one of the interesting things about the moon as well is that it is sovereign, right? Like it's because you're, you're not in, you're not on the planet anymore. So it's, it is a safe place for whipping, but please don't quote me on that. It's a libertarian paradise on so many axes. Exactly.
Starting point is 00:07:50 So yeah, when we think of engineers, we use that term very loosely. I think of it as more of a builder or a technical expert than necessarily, yeah, somebody who's building software. So we have a lot of scientists who are doing biotech or hardware design. We're pretty agnostic in terms of what kind of engineering you are, as long as it is a thing that you
Starting point is 00:08:09 are a technical expert in. Again, sort of the thinking behind that, behind the curtain is more like, if you run out of money, can you keep building? It's like somebody can be really good at selling an idea and being a salesperson. You see that all the time in startups. But can that person also build the thing
Starting point is 00:08:23 that they're pitching? And if they can, then that gives you a lot more leeway in terms of financing and staying alive in all kinds of funding environments, because you don't need to pay someone to build it. You can really build it and understand it yourself. The way that I tend to see VC done well is exactly what you're talking about.
Starting point is 00:08:40 The problem is that's not what gets the headlines. It's, hey, someone who worked at OpenAI for a time has decided to leave and start their own AI company. They have no idea what they're going to do yet, but they've raised a $3 billion seed round. Huh. Okay, good luck. I feel like there's some pieces of that story missing.
Starting point is 00:09:00 But the interesting VC stuff is all relatively small scale. I like what I term boring businesses. The idea of, oh, what do you do? It's like, oh, we help do back end data processing for healthcare companies. Like, oh wow, that is going to sound, A, incredibly boring and B, extraordinarily lucrative. That's the fun stuff. It doesn't make the headlines, but let's be honest, other than pictures in the New York Times of me holding a dog aside,
Starting point is 00:09:28 I don't necessarily want to be in the headlines all the time. I think, yeah, I would agree with you entirely, although I don't think a lot of our companies I would describe as boring. I do think that similar to what you're saying is they do solve a real problem and not just, you know, how many Twitter followers, no offense to present company, do you have in order to market your product, right? One of the things that we like to say is, look crazy, be right. And so you don't have to capture the attention if you're really solving this foundational problem, the market creates itself, right?
Starting point is 00:09:58 It really does. I wanna talk a little bit about you in the sense that you don't, you aren't shaped like the traditional VC type because frankly you're not really shaped like anything I think I've come across before. You're an attorney, which okay, I've seen some of those before. You have got, you said, eh, I don't want to do that, went into the VC direction.
Starting point is 00:10:22 We have weird interleavings throughout our history. It turns out you were a dive instructor at the same middle of nowhere island in Thailand within the same time frame as I was there getting certified 15 years ago. We probably passed like ships in the night. You do a lot of interesting stuff. And I empathize with the aspect that a lot of it is very hard to describe to people who aren't involved in the day toto-day of it because when I go to cocktail parties with other dads from the elementary school or whatnot and they ask, oh so what do you do? It turns out that outside of our space there's no answer I can give that doesn't make me sound utterly deranged. Well you are utterly deranged and I
Starting point is 00:10:59 would say that is a thing that you and I have in common and I think one of the one of the fine qualities of the Utterly Deranged is that we follow our passions and our curiosities without like more throwing caution to the wind. And I think I've been really lucky to be able to do that throughout my life, really lucky or really motivated or just really deranged, I suppose. And yeah, I actually even prior to becoming an attorney, I studied marine biology in college. I briefly worked in the arts at a national arts nonprofit. Then I essentially realized I needed some tools to be taken seriously if I was going
Starting point is 00:11:33 to be this ridiculous. So I more or less became an attorney to get a seat at that table and to be able to work on some of the problems that I thought were important and to have that value that I knew I could have. But apparently I needed a piece of paper to let everybody else know that I had that ability to add value. So became an attorney and then did what I guess a lot of folks in law wanna do.
Starting point is 00:11:55 And I went in-house out of law school to work at an ad tech company doing privacy and data security work right during the rise of GDPR. So sort of like right place, right time, if that's what you want to do. But in the sense that it was a level playing field, right? Like privacy and all of this was pretty new. So even really seasoned attorneys knew about as much about it as I did. And so I kind of landed right at this company, but it was post-acquisition. So it was a very small legal team and I was trying to do compliance
Starting point is 00:12:27 and I guess data audits of a company and I had no idea what that was. So I went and I sat down with every engineer in the company who would speak to me. It's like, you know, new attorney, hey, I'm doing compliance, can I please hang out with you and ask you some questions? There's no...
Starting point is 00:12:43 How is that not, that sounds awesome. Let me clear my afternoon. Well, let's put it this way. I developed a skill that I think has served me really well, which is if you lead with curiosity, like I want to understand what you do, really show me the logs, really show me on a technical level, let me show interest in what you're doing. And if I really was interested, I really was curious. And I learned a hell of a lot. And I ended up actually leaving after 11 months another thing you're not really supposed to do. Especially in law, in tech you can just spin a narrative,
Starting point is 00:13:14 but when you're a practicing attorney, there is a record of when you worked where to where, you can't sweep it under the rug in the same way. But I mean, why should you have to sleep under the rug, right? People say you have to stay at one job for one year. And I kind of looked around and I was like, what magical thing is going to happen to me in this one month? If I already know that it's time for me to move on and I have enough information and
Starting point is 00:13:34 I know that this is the right choice for me, you know, time is my most valuable. Because lawyers are judgy. Well, people are judgy, honestly. The thing I've learned is until I started this place, I never crossed the two-year mark at any company. So I was consistently dealing with folks in job interviews who were like, well, you haven't really stayed around anywhere for a long period of time. But then I talked to other people once I started this place and like, oh yeah, I've been at
Starting point is 00:13:58 my company for eight years and an awful lot of people judge me for that because I've been here for too long. It's, no one's happy. People just want to judge other folks. Well, I mean, you're just having fun, I think, because I know I'm the same way. I so like the short version of the story is I just kept quitting my job anywhere from 10 months to 11 months. And a certain point, I was like, maybe I should just be a consultant.
Starting point is 00:14:21 I can't seem to stay anywhere for very long until I found a typical. And now I've been there for four Years and I probably shouldn't joke about this on a podcast But here I will I used to tell Chris when I first started that he would have to get a restraining order to get me to leave Which is fair. It's a I find that on some level you whine you the people who are just able to actualize what it is They want to do like what should I do with my career? Early on no one knows, but the more years I spend doing this stuff, I realize the things
Starting point is 00:14:50 I do that I'm most passionate about are the things you couldn't stop me from doing. Great, okay, take the company away. I'm still going to be shitposting about big tech because it interests me to do it. I have a perspective that for better or worse is not often well represented. And I frankly like making fun of things that can't punch back. I couldn't agree more. I think everything about now like if you had asked me what I wanted to do, I don't know if I would have ever been able to say it's venture capital, which is why I find it endlessly funny when people ask me the very famous question, how
Starting point is 00:15:20 do you break into venture? And if I had any idea, I would tell someone, but I really don't. For me, it's the things you can't stop me reading about science, being extremely hard, like being just extremely bad at staying on topic. So like this is like, I'm basically ADHD for a living now. And then I think the important thing is I really love being of service of smart people who are building cool things. And one of the things that always irked me about being an attorney and I was helping a lot of after the tech company, I actually had my own law firm where I was helping companies from around pre-incorporation through series A. And I didn't really like taking their money because they didn't have any.
Starting point is 00:15:56 That's not a great business model for a law firm, but it is for a VC. So I get to now give them that money and still provide them that support and be of service. And it kind of feels like in some small way, maybe I'm helping to put that data center on the moon. Maybe I'm helping this company get past that really delicate early stage and be able to flourish. And these are founders to not wanting to sound too corny, but that I really believe in that
Starting point is 00:16:18 I think are doing things that are going to set them apart and add value in the world. And I get to help them. That's a pretty cool gig. You would definitely have to pay me to stop doing it. This episode is sponsored by my own company, the Duckbill Group. Having trouble with your AWS bill? Perhaps it's time to renegotiate a contract with them. Maybe you're just wondering how to predict what's going on in the wide world of AWS.
Starting point is 00:16:43 Well, that's where the Duck Bill Group comes in to help. Remember, you can't duck the Duck Bill Bill, which I am reliably informed by my business partner is absolutely not our motto. One of the things I learned as I spend more time talking to VCs often against my will has been that the day to day never looks the same. They're the ones I talk to.
Starting point is 00:17:08 That resonates with me. If I sit down and, oh yes, if you look at my calendar, there are a few standing things I do every week at certain times, but not a lot. I don't tend to go in and, well, the first four hours of the day I'll be doing Project X and then move on to Project Y. Some days I'm doing podcasting, some days I'm doing consulting work, some days I'm meeting random folk to have conversations about esoteric nonsense.
Starting point is 00:17:29 And it all builds to something sooner or later, but it's the variety that speaks to me. Yeah, and there's not really like a, like if this, then this. It's not like, oh, here, like getting these tasks done will like lead to hitting these marks for this quarter. It really is that talking up to random people about esoteric things, being generous with your time whenever you can be learning about people, trying to add value for people. And it
Starting point is 00:17:55 really does start to sort of build on itself. So yeah, I mean, in some ways, it's a blessing and a curse because I think so much of my life I've designed around things that will improve my capacity as a VC. So whether it's the things that I read or what I pay attention to, time and attention, I think being your most valuable assets in life and that's what motivates me. So I, yeah, I get to learn something new. I get to talk to brilliant people
Starting point is 00:18:19 and ask them questions about what they're building. And then it all adds on to itself. And I think eventually makes you better and better at this job. I would agree wholeheartedly. I think you also touched on something that I think is not well internalized by folks is that time and attention is the most valuable thing you have. I get a whole bunch of crappy sales outreach of, hey, can we jump on a quick call so I could talk to you about my thing?
Starting point is 00:18:42 Like, okay, great, Budget half an hour for that. Impute what your hourly rate is and imagine how you would respond to an email of like, hey, can I have fill in the blank here dollars because that's functionally what it is. And people would have a negative visceral reaction to that. Whereas, oh yeah, just give me time. Well, people don't value that in the way that I'd argue they probably should. Well, I'll be sending you my bill after this, certainly. Well, that's actually one of the reasons that I left the law is that there isn't an amount
Starting point is 00:19:12 of money that I want to attach to my time. I think in some ways I understand that framework of thinking about it. But for me, I think time is your only non renewable resource and money for better force is renewable, right? You can be financially ruined, you can come back from it, you can make money and lose money in a lifetime, but it's not finite, right? Like there's more of it in the world. There's different ways of making it. But time you really, I mean, maybe now like we'll see with like some of this like longevity stuff, or maybe if we upload ourselves to the cloud, see tied it back. That's not renewable. So I'm not going to tie it to a
Starting point is 00:19:49 resource that is. And I think that's one of my weird life frameworks that I think about it with. And so venture, I think, I think one of like the tricks then is how can you separate the two? So I think in venture, there isn't really a correlation between the amount of time that you put in and how much money you make, right? I think some of it is like luck, some of it is building relationships, some of it is putting in the work, but it's you can have exponential returns that are not tied to an hourly rate. And I think that is an appealing thing to me in a profession. It absolutely is. I think that that is
Starting point is 00:20:22 to me in a profession. It absolutely is. I think that that is a mistake a lot of folks make. When I started consulting after being surprised fired from BlackRock before I went out on my own, I looked for something I could do on a fixed fee project basis at first just because otherwise, as soon as you view things through a lens of billable hours, it forever colors how you interact with folks. Do I want to spend this evening playing with my kids or I could be billing during that time if I go to work instead?
Starting point is 00:20:51 Should I grab coffee with this interesting person? Well, I don't know. What's the opportunity cost trade off? Over-indexing on time leads to missing out on a lot of moments in life that I'm not interested in giving up. And I find it a little bit depressing to actually track your time in that way. Because when you do think about it, how could you ever value spending time with your kids versus doing your billing?
Starting point is 00:21:12 And in that case, you would never do your billing. So I think it's, I think it's a trap. So I think, and I feel very lucky that I figured that out for myself. And I know it's probably not true for everyone, but it is something that I make every effort to avoid putting that context of time is money. It's like, no, time is everything. Time is life. Oh, yeah.
Starting point is 00:21:32 Oh, yes. It's the one currency we can't mint more of. But it's also don't step over dollars to pick up pennies, if that makes sense. I hate it when we have to go back to capitalist metaphors for these things. In other news, we mentioned that you're a diver. You're also apparently a cave diver. You also go alpine climbing a fair bit. So, really bad at risk assessment or just no sense of self-preservation? Maybe both. That's why I'm a good VC. There we are. I'm really bad at judging risk. It's a hell of a pitch for a VC.
Starting point is 00:22:04 Why should we take investment from you? Oh, we're terrible at figuring out how things are going to go. We're basically betting it all on a well-dressed horse. I don't know. I'd probably invest in a well-dressed horse if ever I met one. Oh, my stars. Yes. It's a, hey, aren't you the horse from my last race around? Yeah, yeah, it'll be great. We actually see which recent investment is in the biotech space they're going to be making, speaking of well-dressed horses, they're going to be making unicorns and potentially dragons. I am so angry about that. You have no idea because look, unicorns don't exist. A horse with a horn, that's absurd. Counterpoint, look at giraffes. Those are somehow supposedly
Starting point is 00:22:47 real. I'm a giraffe denialist. I say that they are not real. I mean, I've seen them. I still don't believe they're there and I insist that they're not real and I make that point adamantly to my children who will no doubt take that to therapy when they're older. Right. So I had no idea something like this was going to come up today, but now I need a little bit more information, are there any other animals that you deny their existence? Sort of, I have a established 2010 Quins poster
Starting point is 00:23:13 in my home, in my kitchen, and when the dog from the front page of the New York Times died, I put a circle with a red slash to it sticker over her on that, so yeah, we basically have written her out of history. That's dark, it's really dark. Oh, truly so. She was a terrible little dog whom we love very much.
Starting point is 00:23:31 She had a 17 year run. That was a decent stretch for a little dog too ornery to die, she always. But yeah, it was fun. And now you have to laugh or you'll cry. I'm a big fan of Gallo's humor. That is a thing I've picked up on from you. The less funny, as I've learned today, your greatest compliment is that wasn't funny.
Starting point is 00:23:53 I want to give nuance to that. I feel that I've said that before and people have taken as license to be absolute shitheads to one another. That's not funny because it's striking at a marginalized group, it's punching down. That's not funny. You should probably find a better joke. That's not funny because I didn't personally laugh at it. Okay. Or that's too far. Sure, but someone isn't harmed by it. If it's not aimed at a particular demographic or, alternately, is punching clearly up at giant companies or
Starting point is 00:24:26 people who are commonly addressed by the phrase Senator. Great. You could you have a lot more license to play those games. See you have to see you have to you have to have those sort of you have to pull back a little on those because you're on social media so people can come after you. Well it's partially that but it's also the I don't want people to have a bad time and I don't want to inspire, I guess, crappy copycats who are doing the oh, I'm just going to go ahead and do the snarky thing that you do. John Scalzi famously has said for years that the failure mode of clever is asshole and he's not wrong.
Starting point is 00:25:01 If you get it wrong, you have potentially harmed some people through no intent. And then the question is when you learn you've done that, what do you do with that? Do you double down and double down and double down again, like so many seem to? Or do you realize that, spoiler, apologies are free. And if it hurts people, maybe the joke's not that funny.
Starting point is 00:25:22 Time to think of a better one. It's sort of a crucible that shapes the direction that you wanna go in. And the nice thing about life is we get to choose every day who we wanna be. Yep, apologies are free and they're also a superpower. I mean, I think in similar to cold outreach and similar to not being afraid to have your own opinion
Starting point is 00:25:41 and not follow the herd and not give in to hype. I think these end up being superpowers and maybe unrelated to my I'm not good about judging risk, which I actually think I very much am. And I think that's part of the that is part of the humility. You're still with us. So clearly so. Correct. And I think that's part of the humility of climbing a mountain or even I mean, I can certainly relate it to my job, but using the mountain as a metaphor, getting close to the summit and knowing that you have to turn around
Starting point is 00:26:05 and not having it being about getting to the top. And it gets corny very quickly talking about these things, but it is a very hard thing. You spend the whole year preparing, you have the gear, you go on the trip, you get very, very close, and then sometimes you have to turn back. And I think not everyone does.
Starting point is 00:26:22 And I think that's very dangerous. You could put other people at risk. What's the line like Mount Everest is full of bodies, every one of whom was a highly motivated person? That sounds like it is a quote. And I think a lot of question people ask me often is if I would try to climb Everest and I absolutely would. And I think the caveat there is I wouldn't pay my way up.
Starting point is 00:26:40 I think not to say that you don't have to, you know, buy a permit and I would certainly work with a guide and. I'm gonna hire a bunch of teams of people, of Sherpas, who wind up doing this weekly for a living and they're gonna basically drag my ass up the mountain so I can say I did it, no thanks. No, I wouldn't wanna do that. I would wanna be able to feel confident
Starting point is 00:27:00 in my ability to self-rescue, I'd wanna feel confident in my ability to do, like I wanna feel like I could do it on my own. And then I think it's okay to also have help. I think that's a risk assessment. I guess we're on a podcast. You can't tell, but I am a fairly small human. And I think that I know some of my limits and I think I would make that judgment call at the time. So for something like Everest, I would do all the work. And if I felt like I was prepared enough to do it, I would go ahead with it.
Starting point is 00:27:26 And if I didn't, I wouldn't. And I think I am proud of my ability to pull back when I need to. And the joy is in the work. It's like diving. Anyone can thumb a dive and edit it at any time for any reason without justification. And I've done that a few times when
Starting point is 00:27:43 I thought that my dive buddy was pushing limits where it's okay I if you call someone out they get defensive and I'm not feeling this. Oh, okay, then they get to play hero They are getting argumentative and confronting. They're being the good person to help their buddy who's struggling Yeah, there's a there's There's something to be said for being able to do that and still maintain face. When people feel that they would be losing something by backing down, so they're going to go through it regardless, that's where things get really dicey. Not just with personal risk, but with like, I'm not comfortable doing what I'm doing, but I've come this far. I have to keep going.
Starting point is 00:28:20 It can lead to bad outcomes. And that's like this. And again, like I can tie that to venture certainly, right? I've already invested and this is my reputation and I've told everyone that this is great. Maybe I've learned something else about it. Do you take your obligation seriously to pull back when you need to pull back, right? Is there like a sunk cost here? And I think when you start thinking about it in that sense, I think there's a lot of egos in this industry. I think that's start thinking about it, in that sense, I think there's a lot of egos in this industry.
Starting point is 00:28:45 I think that's very, very dangerous. I guess this is maybe the lawyer in me, but I feel very strongly about my job. Like, ultimately, I'm a fiduciary for my LPs. And I feel very strongly about being that custodian of their capital. And so I have to remove my ego from it. And if I'm wrong about something, I can be wrong about it, right? I'm not promising that I'm right 100% of the time, but I am promising that I'm going to be honest and self-aware and admit when I am wrong and not just double down to prop up an investment, for example. I really want to
Starting point is 00:29:16 thank you for taking the time to speak with me. If people want to learn more about what you're up to these days, where's the best place for them to find you given that you are one of those people we term as happy who is not on social media? Gosh, that's a good question. I guess email, is that the answer? I'm allowed to give. I would always direct them to the website. That's what atypical.vc is for.
Starting point is 00:29:38 And we will of course be putting that in the show notes. For once, it's me being self-promotional as well. So I'll go for it. Sure, you try the website. the landing page, if you will. But yeah, that's perfect. Awesome. Thank you again for your time. I really appreciate it. It's an absolute blast every time we get the chat.
Starting point is 00:29:56 Thanks, Corey. Likewise, Lily Rogowski, partner at Atypical Ventures. I'm cloud economist Corey Quinn, and this is Screaming in the Cloud. If you've enjoyed this podcast, please leave a five star review on your podcast platform of choice. Whereas if you've hated this podcast, please leave a five star review on your podcast platform of choice, along with an angry comment in which you categorically refuse to even slightly consider the possibility that you might be wrong about something.

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