Finding Engineers with Empathy with Lili Rogowsky

Summary

Podcast Summary: Screaming in the Cloud – "Finding Engineers with Empathy with Lili Rogowsky"

Introduction and Backgrounds

In the episode titled "Finding Engineers with Empathy with Lili Rogowsky," host Corey Quinn engages in an enlightening conversation with Lily Rogowski, a multifaceted professional who has traversed diverse career paths from law to venture capital. The discussion delves into Lily's journey, the philosophy behind her venture firm, Atypical Ventures, and the unique concept of "Engineers of Empathy."

Notable Quote:

Lily Rogowski [00:00]: "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."

Atypical Ventures and Investment Thesis

Corey initiates the discussion by exploring Lily's venture firm, Atypical Ventures. Initially intrigued by Lily's unconventional approach, Corey seeks to understand the firm's investment philosophy. Lily elaborates on Atypical Ventures' focus on early-stage investments, specifically targeting founders she terms "Engineers of Empathy."

Notable Quote:

Lily Rogowski [04:28]: "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."

Lily emphasizes the importance of founders possessing both technical expertise and the emotional intelligence necessary to foster strong team dynamics. This duality ensures that startups are not only technically robust but also culturally resilient.

The Importance of Empathy in Engineering

A significant portion of the conversation centers around the concept of "Engineers of Empathy." Lily defines this archetype as founders who blend technical proficiency with empathetic leadership. This combination is pivotal for navigating the complexities of early-stage startups, where technical challenges are often intertwined with interpersonal dynamics.

Notable Quote:

Lily Rogowski [04:28]: "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."

Lily underscores that the ability to adapt one’s mental models and decision-making processes is more critical than static beliefs. This flexibility is particularly valuable in the dynamic landscape of venture-backed startups.

Personal Experiences and Career Paths

Corey and Lily share insights into their personal journeys, highlighting Lily's transition from law to venture capital. Lily recounts her experience running her own law firm, assisting pre-incorporation companies through Series A funding, and her desire to provide both financial support and valuable guidance without the stringent constraints of traditional law firm models.

Notable Quote:

Lily Rogowski [16:28]: "I get to help them ... these are founders that I really believe 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."

Lily's transition was motivated by her passion for supporting innovative founders and her discomfort with conventional law firm profit models, which often prioritize financial gain over meaningful engagement.

The Value of Time vs. Money

A profound segment of the dialogue explores the intrinsic value of time over money. Both Corey and Lily express a shared philosophy that time is a finite, non-renewable resource, unlike money, which is seen as more renewable and fungible.

Notable Quote:

Lily Rogowski [19:03]: "Time is your most valuable because lawyers are judgy."

Lily articulates a framework where time is prioritized over monetary compensation, arguing that the former cannot be replenished, whereas financial setbacks can often be recovered from. This perspective informs her approach to venture capital, where the focus is on long-term relationships and value creation rather than short-term financial metrics.

Risk Assessment and Personal Interests

The conversation takes a personal turn as Corey highlights his perceptions of Lily's adventurous spirit, noting her interests in diving, cave diving, and alpine climbing. Lily connects these high-risk activities to her professional life in venture capital, suggesting that risk assessment is a critical skill both in extreme sports and in evaluating startup investments.

Notable Quote:

Lily Rogowski [21:32]: "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."

Lily emphasizes the importance of self-awareness and humility in both personal and professional risk-taking, advocating for a balanced approach that recognizes one's limitations while striving for ambitious goals.

Navigating Failure and Accountability

Corey and Lily discuss the inevitability of failure in both personal endeavors and venture investments. Lily stresses the importance of accountability and the willingness to admit mistakes, highlighting her role as a fiduciary to her limited partners (LPs). She advocates for transparency and integrity, ensuring that egos do not cloud judgment or lead to unfounded persistence in failing investments.

Notable Quote:

Lily Rogowski [25:53]: "I have to remove my ego from it. And if I'm wrong about something, I can be wrong about it, right?"

This approach fosters a culture of honesty and continuous learning, essential for long-term success in the volatile world of startups and venture funding.

Conclusion and Final Thoughts

As the episode draws to a close, Corey and Lily reflect on the importance of authenticity and the courage to follow one's passions without succumbing to external pressures or conventional expectations. They reiterate the value of time, the significance of empathetic leadership, and the necessity of balancing risk with self-awareness.

Notable Quote:

Corey Quinn [30:34]: "It's."

The conversation ends on a light-hearted note, underscoring the mutual respect and shared values between Corey and Lily, both of whom are passionate about their respective fields and committed to fostering meaningful change within the cloud computing and venture capital landscapes.

Key Takeaways

1. Engineers of Empathy: A unique founder archetype that blends technical skills with emotional intelligence, essential for building resilient and innovative startups.
2. Time vs. Money: Prioritizing time as the most valuable, non-renewable resource over monetary gains, leading to more meaningful and sustainable career choices.
3. Authenticity and Accountability: Emphasizing honesty, self-awareness, and the willingness to admit mistakes as foundational for personal growth and professional success.
4. Risk Assessment: The ability to evaluate and manage risk effectively, both in extreme sports and in venture investments, is crucial for long-term stability and achievement.

Connecting with Lily Rogowski

For listeners interested in learning more about Lily Rogowski and her work with Atypical Ventures, the best avenue is through the official website of Atypical Ventures, which will be provided in the show notes.

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This summary encapsulates the key discussions, insights, and humorous exchanges between Corey Quinn and Lily Rogowski, offering a comprehensive overview for those who haven't listened to the episode.

Transcript

[Lily Rogowski]

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 not wanting to sound too corny but that I really believe in that 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.

[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. 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.

[Lily Rogowski]

Thank you for having me, Corey.

[Corey Quinn]

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. I want to start at the beginning, but I sort of forget where that even started because you reached out to me years ago on LinkedIn and I forget even what it was that you 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?

[Lily Rogowski]

It'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 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 and you had a picture of yourself holding a dog. And I thought this is the. 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 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. But this was years ago. We started talking.

[Lily Rogowski]

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 people go to pleasure themselves publicly.

[Lily Rogowski]

Why does it always go there with you, Corey?

[Corey Quinn]

You know, one wonders quite a bit. 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. As of relatively recently, I'm an advisor to one of your funds which is fun and exciting.

[Lily Rogowski]

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.

[Corey Quinn]

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. That's not our stuff. That's nerd shit. 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.

[Lily Rogowski]

Well, we're going to 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 is your. What sector do you invest in? And 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? And then, 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 of Empathy. 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 going to 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 of, oh, we invest in engineers with empathy. It's like, okay, so they're building what, Microsoft Excel with emoji in it? You're like, no, we're talking data centers on the moon style stuff. I thought you were kidding. And you weren't kidding. You actually did it.

[Lily Rogowski]

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.

[Lily Rogowski]

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 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 want to dive into that a little.

[Corey Quinn]

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. So expanding to the moon is absolutely the loophole they're going for.

[Lily Rogowski]

We always need loopholes. That's very important.

[Corey Quinn]

Take you to the moon, we can horsewhip you there. It'll be great. I'm kidding. Amazon does that anyway, and it's interesting.

[Lily Rogowski]

Because it is a. One of the interesting things about the moon as well is that it is sovereign. Right. Because you're not on the planet anymore. So it is a safe place for whipping. But please don't quote me on that.

[Corey Quinn]

It's a libertarian paradise on so many axes.

[Lily Rogowski]

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 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 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.

[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 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. 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, I don't necessarily want to be in the headlines all the time.

[Lily Rogowski]

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 how many Twitter followers, no offense to present company, do you have in order to market your product? 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 want to 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. I don't want to do that. Went into the VC direction. 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 timeframe as I was there getting certified 15 years ago. We probably passed 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 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.

[Lily Rogowski]

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 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 to study marine biology in college. I briefly worked in the arts at an 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 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 want to do. 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, 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 I. 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 a.

[Corey Quinn]

How is that? Not. That sounds awesome. Let me clear my afternoon.

[Lily Rogowski]

Well, let's put it this way. I developed skill that I think has served me really well, which is if you lead with curiosity, 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 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.

[Corey Quinn]

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 worked, where to where you can't sweep it under the rug in the same way.

[Lily Rogowski]

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, 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 is the right choice for me, Time is my most valuable because lawyers are judgy.

[Corey Quinn]

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 are 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 because I've been here for too long. No one's happy. People just want to judge other folks.

[Lily Rogowski]

Well, I mean, you're just having fun, I think, because I know 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 at 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.

[Corey Quinn]

To leave, which is fair. I find that on some level, people who are able to actualize what it is they want to do, 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 the 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, 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.

[Lily Rogowski]

I couldn't agree more. I think everything about, 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 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 in reading about science being extremely hard, like, 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. 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 not wanting to sound too corny but that I really believe in that I think are doing things that are going to 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]

This episode is sponsored by my own company, the Duck Bill 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. 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'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. At least the ones I talk to where 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 sometimes 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.

[Lily Rogowski]

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 really does start to sort of build on its. 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 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? 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 argue. They probably should.

[Lily Rogowski]

Well, I'll be sending 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. 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 for worse 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 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 one of 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. I think some of it is luck, some of it is building relationships, some of it is putting in the work. But 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 want to 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. 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.

[Lily Rogowski]

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. 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 everything. Time is life.

[Corey Quinn]

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, 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?

[Lily Rogowski]

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 going to go. We're basically betting it all on a well dressed horse.

[Lily Rogowski]

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

[Corey Quinn]

Oh my stars. Yes. Hey, aren't you the horse from my last race round? Yeah, it'll be great.

[Lily Rogowski]

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

[Corey Quinn]

So 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, 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.

[Lily Rogowski]

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?

[Corey Quinn]

Sort of. I have a established 2010 Quinn's poster in my home in my kitchen. And when the dog from the front page New York Times died, I put a circle with a red slash through its sticker over her on that. So, yeah, we basically have written her out of history.

[Lily Rogowski]

That's dark. Really dark.

[Corey Quinn]

Oh, truly. So she was a terrible little dog whom we love very much. She had a 17 year run. That was a decent stretch for a little dog. Too ornery to die Chihuahuas. But yeah, it was fun. And now you have to laugh or you'll cry. I'm a big fan of Gallo's humor.

[Lily Rogowski]

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]

I want to give nuance to that just because I feel that I've said that before and people have taken his license to be absolute shitheels 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.

[Lily Rogowski]

See, 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.

[Corey Quinn]

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 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 crucible that shapes the direction that you want to go in. The nice thing about life is we get to choose every day who we want to be.

[Lily Rogowski]

Yep. Apologies are free, and they're also a superpower. I mean, I think similar to cold outreach and similar to not being afraid to have your own opinion, 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.

[Corey Quinn]

You're still with us so clearly, so correct.

[Lily Rogowski]

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 and not having it being 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 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? Mount Everest is full of bodies, every one of whom was a highly motivated person.

[Lily Rogowski]

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. I think not to say that you don't have to buy a perm. I would certainly work with a guide.

[Corey Quinn]

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.

[Lily Rogowski]

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'd 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, 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 and edit at any time for any reason without justification. And like 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 are 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 going to go through it regardless of. 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 and that's like this.

[Lily Rogowski]

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 very, very dangerous. I guess this is maybe the lawyer in me, but I feel very strongly about my job. 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 and admit when I am wrong and not just double down to prop up an investment.

[Corey Quinn]

For example, I really want to 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?

[Lily Rogowski]

Gosh, that's a good question. I guess. Email? Is that an answer I'm allowed to give?

[Corey Quinn]

I would always direct them 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.

[Lily Rogowski]

Sure, 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 absolute blast every time we get the chat.

[Lily Rogowski]

Thanks Corey.

[Corey Quinn]

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.

[Lily Rogowski]

It.