Finding Engineers with Empathy with Lili Rogowsky

Episode Summary

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 unconventional 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.

Episode Video

Episode Show Notes & Transcript



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 Ventures


About Lili Rogowsky
Lili 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.


Links


Sponsor
The Duckbill Group: duckbillgroup.com

Transcript

Lili Rogowsky: 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 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, like, really delicate early stage and be able to flourish, and these are founders to, like, not wanting to sound too corny, but that I really believe in, that I think are doing things that are gonna set them apart and add value in the world, and I get to help them?

Like that's a pretty cool gig. You would definitely have to pay me to stop doing it.

Corey Quinn: 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. Lili Rogowski is an awful lot of things. Professionally, she's a partner at Atypical Ventures and also tolerates talking to me.

Lili, thanks for joining me.

Lili Rogowsky: Thank you for having me, Cory.

Sponsor: This episode is sponsored in part by my day job, the Duckbill 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 Duckbill bill.

And my CEO informs me that is absolutely not our slogan.

Corey Quinn: So I wanna start at the beginning, but I sort of forget where that even started, 'cause 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?

Lili Rogowsky: That's a really excellent question. The answer is, I don't know. 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 from working with him and at some point realized how much of a value add that was going to be, and I read an article about you in the New York Times. You had a picture of yourself holding a dog, and I thought, it was hilarious. I was like, "This person is snarky and what a strange article and what a great photo. I should reach out to him." And I don't know that I had a point, and I tried to kind of hide that in my outreach to you, and 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.

Corey Quinn: I don't even remember what you said because I get those all the time, and I immediately hit the "not interested" button, or I just closed the tab or get distracted by something shiny.

But this was years ago. We started talking.

Lili Rogowsky: Yeah, I think it was that it was very self-deprecating. I think that that maybe was like the tone that we had in common, and I think maybe that's what it was.

Corey Quinn: You're definitely onto something there. I have very little patience for folks who are incredibly self-aggrandizing.

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.

Lili Rogowsky: Why does it always go there with you, Corey?

Corey Quinn: You know one wonders quite a bit.

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 a relatively recently, I'm an advisor to one of your funds, which is fun and exciting.

Lili Rogowsky: 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.

Corey Quinn: What I found fascinating about the whole story is that, okay, Atypical Ventures great. What's your investment thesis? And the answers started off with, "Oh yeah, we're basically doing nothing with software. That's not our stuff. That's nerd shit," and it was awesome. You probably do a better story of telling me what your investment thesis.

I haven't memorized the talking points yet. Hit me with it.

Lili Rogowsky: 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 for you to study from. So we, there's a few different ways that we like to frame it. I think the typical questions are, you know, "What stage do you invest in?" "What sector do you invest in?" and in those answers, very early stage, as early as we can find them, can we compel them to start this company when we read the research paper? And then we look for what we call "plausible science fiction," which we can get into, and it is, like, 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, 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 gonna make decisions in the future. 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.

Corey Quinn: I want to be very clear here because the audience expects certain directions. 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. "Oh, we invest in engineers with empathy." It's like, "Okay, so they're building what? Microsoft Excel with emoji in it," 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.

Lili Rogowsky: 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.

Corey Quinn: Insert obvious joke about AWS data transfer fees to the moon here.

Lili Rogowsky: Well Corey, fortunately, Lonestar has the spectrum rights between the earth and the moon. So there's actually, we can go down that line, but that's a very, very interesting point to point. 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, or unless you wanna dive into that a little.

Corey Quinn: No, I just wanna 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." so expanding to the moon is absolutely the loophole they're going for.

Lili Rogowsky: We always need loopholes. That's very important.

Corey Quinn: "Take you to the moon. We can horse whip you there. It'll be great." I'm kidding. Amazon does that anyway.

Lili Rogowsky: And it's interesting because 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 not in, you're not on the planet anymore. So it's a safe place for whipping, but please don't quote me on that.

Corey Quinn: It's a Libertarian paradise on so many axes.

Lili Rogowsky: Exactly. 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 are a technical expert in. Again, sort of the thinking behind that, behind the curtain is more like, if you run outta money, can you keep building?

Like do you really, 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 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, 'cause you don't need to pay someone to build it. You can really build it and understand it yourself.

Corey Quinn: The way that I tend to see VC done well is exactly what you're talking about. 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 gonna do yet, but they've raised a $3 billion seed round." Huh? Okay. I, good luck. I feel like there's some pieces of that story missing, but the interesting VC stuff is all relatively small scale. Like I like what I term "boring businesses." The idea of, "Oh, what do you do?"

It's like, "Oh, we help do backend data processing for healthcare companies." Like, oh wow, that is gonna 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, you know, pictures in the New York Times of me holding a dog aside, I don't necessarily wanna be in the headlines all the time.

Lili Rogowsky: 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 were 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?

Corey Quinn: It really does.

I wanna talk a little bit about you in the sense that 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 decided, "Eh, I don't wanna do that," went into the VC direction, but we have weird interweavings throughout our history. It turns out you were a dive instructor at the same middle of nowhere island in Thailand about within the same timeframe 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's very hard to describe to people who aren't involved in the day-to-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.

Lili Rogowsky: Well, you are utterly deranged, and I would say that is a thing that you and I have in common. And I think one of the fine qualities of the utterly deranged is that we follow our passions and our curiosities without, like, while 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 tried, I was studying marine biology in college. I briefly worked in the arts at a national arts nonprofit, and then I essentially realized I needed some tools to be taken seriously if I was going 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 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, and I went in-house out of law school to work in 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 wanna 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 it, much about it as I did. And so I kind of landed right at this company. It was post-acquisition, so it was a very small legal team, and I was trying to do compliance 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. I. 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 a.

Corey Quinn: How is that not, that sounds awesome. Let me clear my afternoon.

Lili Rogowsky: Well, like I, 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 wanna 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 I really was interest. I really was curious, and I learned a hell of a lot, and I ended up actually leaving after 11 months.

Corey Quinn: Another thing you're not really supposed to do, especially in law. In tech, you can just spin a narrative, but when you're a practicing attorney, there is a record of when you work where-to-where. You can't sweep it under the rug in the same way.

Lili Rogowsky: But I mean, why should you have to sleep it under the rug, right? People are 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 I know that this the right choice for me.

You know, time is my most valuable.

Corey Quinn: 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 market 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 my company for eight years," and an awful lot of people judge me for that 'cause I've been here for too long. No one's happy. People just want to judge other folks.

Lili Rogowsky: Well, I mean, you're just having fun I think.

I'm the same way. So, the short version of this 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. I can't seem to stay anywhere for very long," until I found Atypical, 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.

Corey Quinn: Which is fair. I find that on some level, the people who are, I guess, 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 I spend the more years I spend doing this stuff, I realize that things I do that I'm the most passionate about are the things you couldn't stop me from doing. Great. Okay. Take the company away, I'm still gonna be shit posting 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.

Lili Rogowsky: 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've ever been able to say it's venture capital, which is why I find it endlessly funny when people ask me that very famous question, "How do you break into venture?"

And if I had any idea, I would tell someone, but I really don't. For me, the thing is you can't stop me is reading about science. Being extremely hard at, like, being just extremely bad at staying on topic. So like, this 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.

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, like, really delicate early stage and be able to flourish. And these are founders to, like, not wanting to sound too corny, but that I really believe in, that I think are doing things that are gonna set them apart and add value in the world, and I get to help them. Like, that's a pretty cool gig. You would definitely have to pay me to stop doing it.

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Corey Quinn: One of the things I've learned as I spend more time talking to VCs, often against my will, has been that the day-to-day never looks the same. There, at least that ones I talk to, where that resonates with me.

If I sit down, 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. And it all builds to something sooner or later, but it's the variety that speaks to me.

Lili Rogowsky: Yeah. And there's not really like a, "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 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 and ask them questions about what they're building, and then it all adds onto itself and I think eventually makes you better and better at this job.

Corey Quinn: I would agree wholeheartedly. I think you also touched on something that I think is not well internalized by folks is that times 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?"

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.

Lili Rogowsky: 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 of money that I want to attach to my time, right? 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 or force, is renewable, right? You can be financially ruined, you can come back from it. You can make money, 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 tying 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 resource that is, and I think that's one of my weird life frameworks that I think about it with. So venture, 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.

Corey Quinn: 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 wanna spend this evening playing with my kids, or I could be billing during that time if I go do work instead? 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.

Lili Rogowsky: 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? And in that case, you would never do your billing. So I think it's a trap, 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, is everything. Time is life.

Corey Quinn: Oh, yeah. 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. We have to go back to capitalist metaphors for these things.

In other news, you, 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.

Lili Rogowsky: Maybe both. That's why I'm a good VC.

Corey Quinn: There we are. "I'm really bad at judging risk," is a hell of a pitch for a VC. All right. It's great. "So why should we take investment from you?" "Oh, we're terrible at figuring out how things are gonna go. We're basically betting it all on a well-dressed horse."

Lili Rogowsky: I don't know. I'd probably invest in a well-dressed horse if ever I met one.

Corey Quinn: Oh my stars. Yes. It's, "Hey, aren't you the horse from my last raise around?" Yeah. Yeah. It'll be great.

Lili Rogowsky: We actually see which recent investment is in the biotech space. They're gonna be making, speaking of well-dressed horse, they're gonna be making unicorns and potentially dragons. So.

Corey Quinn: 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 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.

Lili Rogowsky: Right. So I had no idea something like this was gonna come up today, but now I need a little bit more information. Are there any other animals that you deny their existence?

Corey Quinn: Sort of. I have a established 2010 Quinns poster in my home, in my kitchen, and when the dog from the front page of New York Times died, I put a circle with a red slash threw its sticker over her on that.

So yeah, I, we basically have written her out of history.

Lili Rogowsky: That dark. It's really dark.

Corey Quinn: Oh, truly. So she was a terrible little dog whom we love very much, and you know, she made it, she had a 17 year run that was a decent stretch for a little dog to ornery to die. Chihuahuas. But yeah, it was fun, and now it's, you have to laugh or you'll cry.

I'm a big fan of gallows humor.

Lili Rogowsky: 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.

Corey Quinn: It depends. I want to give nuance to that just because, I feel that I've said that before and people have taken it as license to be absolute shit heels to one another.

That's not funny because it's striking at a marginalized group and 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 if 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 people who are commonly addressed by the phrase "Senator." Great. You have a lot more license to play those games.

Lili Rogowsky: So you have to have those sort of, you have to pull back a little on those 'cause you're onto your own social media so people can come after you.

Corey Quinn: Well, it, 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 gonna 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. 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 time to think of a better one.

It's sort of a a crucible that shapes the direction that you want to go in, and the nice thing about life is we get to choose every day who we wanna be.

Lili Rogowsky: 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, not follow the herd, and not give into hype, I think these end up being superpowers and maybe unrelated to my, I'm not good about judging risks, which I actually think I very much am. And I think that's part of the humility.

Corey Quinn: You're still with us so clearly, so.

Lili Rogowsky: Correct, and I think that's part of the humility of climbing a mountain or be 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 and not having it be about getting to the top.

And it gets very, 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 like, you know, you, you get very, very close and then sometimes you have to turn back and I think not everyone does. And I think that's very dangerous.

You could put other people at risk.

Corey Quinn: What's the line about? Everest is full of bodies, every one of whom was a highly motivated person.

Lili Rogowsky: That sounds like it is a quote. I, and I think a 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 I think. Not to say that you don't have to buy a permit and I would certainly work with a guide.

Corey Quinn: 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.

Lili Rogowsky: No, I wouldn't wanna do that.

I would wanna be able to feel confident 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, right? I'm not, I think that's a risk assessment I guess. We're on a podcast, so 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. 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.

Corey Quinn: It's like diving. Anyone can thumb a dive at any time, for any reason without justification, and I've done that a few times when I thought that my dive buddy was pushing limits where it's, okay, if you call someone out, they get defensive. I'm not feeling this.

Oh, okay. Then they get to play hero. They're getting argumentative and confronting. They're being the good person to help their buddy who's struggling. Yeah, 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 gonna 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. It can lead to bad outcomes.

Lili Rogowsky: And that's like this, and again, I can tie that to venture certainly, right?

I've already invested, and this my reputation, and I've told everyone that this 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 a lot, there's a lot of egos in this industry.

I think that's very, very dangerous. I guess this 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 a hundred percent 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.

Corey Quinn: I really wanna thank you for taking the time to speak with me. If people wanna 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?

Lili Rogowsky: Gosh, that's a good question. I guess email, is that an answer I'm have to give?

Corey Quinn: I would always direct 'em to the website. That's what atypical.vc is for, 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.

Lili Rogowsky: Sure. If you try the website, the landing page if you will, but yeah, that's perfect.

Corey Quinn: Awesome. Thank you again for your time. I really appreciate it. It's an absolute blast every time we get the chat.

Lili Rogowsky: Thanks, Corey. Likewise,

Corey Quinn: Lili Rogowski partner at Atypical Ventures.

I'm cloud economist Cory Quinn, and this 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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