April 15, 2025 • 30 mins
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.
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
- Atypical Ventures: atypical.com
- Email Lili: lili@atypical.vc
Sponsor
The Duckbill Group: duckbillgroup.com
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(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 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.
(00:20):
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.
(00:46):
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.
(01:09):
Lili, thanks for joining me.
Thank you for having me, Cory.
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
(01:31):
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.
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
(01:55):
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?
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.
(02:17):
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.
(02:39):
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.
I don't even remember what you said because I get those all
the time, and I immediately hit the "not interested" button,
(03:02):
or I just closed the tab or get distracted by something shiny.
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 like 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.
It's not polite to say, but I say it anyway, that I
(03:23):
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, I've been very public about being skeptical of the entire VC world, and
(03:44):
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.
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.
(04:04):
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 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.
(04:25):
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 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,
(04:47):
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
(05:11):
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
(05:33):
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
(05:55):
believe, in what their future success will look like.
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."
(06:17):
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.
Yes, we just landed our second mission to the moon last month.
So yes, we've now put a data center on the moon
(06:37):
with another one that will be due to go up.
Insert obvious joke about AWS data transfer fees to the moon here.
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
(06:57):
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.
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
(07:19):
to be the Earth's best employer." so expanding to the
moon is absolutely the loophole they're going for.
We always need loopholes.
That's very important.
"Take you to 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 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.
(07:42):
So it's a safe place for whipping, but please don't quote me on that.
It's a Libertarian paradise on so many axes.
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.
(08:04):
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?
(08:24):
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.
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
(08:46):
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?"
(09:07):
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.
(09:28):
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
(09:50):
right," and so you don't have to capture the attention.
If you're really solving this foundational
problem, the market creates itself, right?
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.
(10:13):
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.
(10:34):
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.
(10:55):
That doesn't make me sound utterly deranged.
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.
(11:15):
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
(11:38):
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.
(12:03):
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
(12:24):
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.
(12:44):
How is that not, that sounds awesome.
Let me clear my afternoon.
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,
(13:05):
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, 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.
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
(13:26):
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.
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.
(13:47):
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.
Well, I mean, you're just having fun I think.
(14:11):
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
(14:31):
have to get a restraining order to get me to leave.
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.
(14:53):
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.
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
(15:15):
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.
(15:38):
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.
(15:59):
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
(16:19):
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.
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
(16:40):
what's going on in the wide world of AWS.
Well, that's where The Duckbill Group comes in to help.
Remember, you can't duck the Duckbill 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.
(17:04):
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.
(17:25):
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.
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.
(17:45):
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.
(18:07):
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.
(18:27):
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
(18:48):
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.
I'll be sending you my bill after this, certainly.
(19:08):
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.
(19:30):
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
(19:50):
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,
(20:13):
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 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
(20:35):
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?
(20:56):
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?
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
(21:19):
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.
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.
(21:40):
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.
Maybe both.
That's why I'm a good VC.
There we are.
"I'm really bad at judging risk," is a hell of a pitch for a VC.
(22:03):
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."
I don't know.
I'd probably invest in a well-dressed horse if ever I met one.
Oh my stars.
Yes.
It's, "Hey, aren't you the horse from my last raise around?" Yeah.
Yeah.
It'll be great.
We actually see which recent investment is in the biotech space.
(22:27):
They're gonna be making, speaking of well-dressed horse,
they're gonna be making unicorns and potentially dragons.
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.
(22:48):
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 gonna come up
today, but now I need a little bit more information.
Are there any other animals that you deny their existence?
(23:10):
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.
That dark.
It's really dark.
Oh, truly.
So she was a terrible little dog whom we love very much,
(23:30):
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.
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.
(23:53):
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.
(24:16):
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.
So you have to have those sort of, you have to pull back a little on those
(24:40):
'cause you're onto your own social media so people can come after you.
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.
(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 time to think of a better one.
(25:23):
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.
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,
(25:47):
I'm not good about judging risks, which I actually think I very much am.
And I think that's 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 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.
(26:08):
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.
What's the line about?
Everest is full of bodies, every one of whom was a highly motivated person.
(26:31):
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.
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
(26:53):
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 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
(27:15):
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.
It's like diving.
(27:35):
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.
(27:58):
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.
(28:20):
It can lead to bad outcomes.
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,
(28:43):
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?
(29:03):
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.
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
(29:24):
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 an answer I'm have to give?
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.
(29:44):
Sure.
If 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.
Thanks, Corey.
Likewise,
Lili Rogowski partner at Atypical Ventures.
I'm cloud economist Cory Quinn, and this Screaming In the Cloud.
(30:06):
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.
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.
(00:20):
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.
(00:46):
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.
(01:09):
Lili, thanks for joining me.
Thank you for having me, Cory.
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
(01:31):
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.
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
(01:55):
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?
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.
(02:17):
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.
(02:39):
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.
I don't even remember what you said because I get those all
the time, and I immediately hit the "not interested" button,
(03:02):
or I just closed the tab or get distracted by something shiny.
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 like 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.
It's not polite to say, but I say it anyway, that I
(03:23):
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, I've been very public about being skeptical of the entire VC world, and
(03:44):
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.
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.
(04:04):
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 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.
(04:25):
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 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,
(04:47):
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
(05:11):
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
(05:33):
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
(05:55):
believe, in what their future success will look like.
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."
(06:17):
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.
Yes, we just landed our second mission to the moon last month.
So yes, we've now put a data center on the moon
(06:37):
with another one that will be due to go up.
Insert obvious joke about AWS data transfer fees to the moon here.
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
(06:57):
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.
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
(07:19):
to be the Earth's best employer." so expanding to the
moon is absolutely the loophole they're going for.
We always need loopholes.
That's very important.
"Take you to 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 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.
(07:42):
So it's a safe place for whipping, but please don't quote me on that.
It's a Libertarian paradise on so many axes.
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.
(08:04):
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?
(08:24):
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.
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
(08:46):
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?"
(09:07):
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.
(09:28):
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
(09:50):
right," and so you don't have to capture the attention.
If you're really solving this foundational
problem, the market creates itself, right?
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.
(10:13):
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.
(10:34):
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.
(10:55):
That doesn't make me sound utterly deranged.
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.
(11:15):
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
(11:38):
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.
(12:03):
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
(12:24):
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.
(12:44):
How is that not, that sounds awesome.
Let me clear my afternoon.
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,
(13:05):
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, 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.
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
(13:26):
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.
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.
(13:47):
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.
Well, I mean, you're just having fun I think.
(14:11):
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
(14:31):
have to get a restraining order to get me to leave.
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.
(14:53):
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.
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
(15:15):
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.
(15:38):
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.
(15:59):
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
(16:19):
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.
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
(16:40):
what's going on in the wide world of AWS.
Well, that's where The Duckbill Group comes in to help.
Remember, you can't duck the Duckbill 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.
(17:04):
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.
(17:25):
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.
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.
(17:45):
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.
(18:07):
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.
(18:27):
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
(18:48):
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.
I'll be sending you my bill after this, certainly.
(19:08):
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.
(19:30):
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
(19:50):
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,
(20:13):
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 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
(20:35):
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?
(20:56):
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?
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
(21:19):
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.
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.
(21:40):
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.
Maybe both.
That's why I'm a good VC.
There we are.
"I'm really bad at judging risk," is a hell of a pitch for a VC.
(22:03):
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."
I don't know.
I'd probably invest in a well-dressed horse if ever I met one.
Oh my stars.
Yes.
It's, "Hey, aren't you the horse from my last raise around?" Yeah.
Yeah.
It'll be great.
We actually see which recent investment is in the biotech space.
(22:27):
They're gonna be making, speaking of well-dressed horse,
they're gonna be making unicorns and potentially dragons.
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.
(22:48):
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 gonna come up
today, but now I need a little bit more information.
Are there any other animals that you deny their existence?
(23:10):
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.
That dark.
It's really dark.
Oh, truly.
So she was a terrible little dog whom we love very much,
(23:30):
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.
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.
(23:53):
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.
(24:16):
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.
So you have to have those sort of, you have to pull back a little on those
(24:40):
'cause you're onto your own social media so people can come after you.
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.
(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 time to think of a better one.
(25:23):
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.
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,
(25:47):
I'm not good about judging risks, which I actually think I very much am.
And I think that's 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 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.
(26:08):
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.
What's the line about?
Everest is full of bodies, every one of whom was a highly motivated person.
(26:31):
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.
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
(26:53):
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 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
(27:15):
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.
It's like diving.
(27:35):
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.
(27:58):
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.
(28:20):
It can lead to bad outcomes.
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,
(28:43):
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?
(29:03):
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.
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
(29:24):
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 an answer I'm have to give?
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.
(29:44):
Sure.
If 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.
Thanks, Corey.
Likewise,
Lili Rogowski partner at Atypical Ventures.
I'm cloud economist Cory Quinn, and this Screaming In the Cloud.
(30:06):
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