The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host)

Transcript from https://podmenti.com/t/a953df6ca6086f46

I wanna start with a a quote by someone you may know, Paul Graham. Much of what's novel about YC
Is due to Jessica Livingston. If you don't know her, you don't understand why she's my three co-founders were deeply technical, but I would look at other things about founders. You know, all these little social cues. Your nickname was the social radar. Every interview, everyone always turned to you and they're like, Jessica. What does the social radar say? I would look at
Do the co-founders get along? Are these people committed? And if a founder would get defensive, that was always a bad sign.
Is there anything else along the Airbnb story that would be interesting to share? He hated their idea and Paul tried to get Brian and Joe and Nate to change it. But I remember specifically, Joe brought out the cereal boxes, the Obama O's and Captain McCain's, and I just thought
Oh my god, they're gonna work hard to do whatever they can to make this company succeed. You just talk a bit about this idea of just making shit happen, showing signs of being hustlers. You sort of need that desperation. You have to burn the boat.

Today my guest is Jessica Livingston.
Jessica is the co-founder of Y Combinator, the first and most famous startup accelerator, which since 2005 has funded over 5,000 companies.
including over two hundred unicorns now worth over a billion dollars.
Including companies like Airbnb, Stripe, DoorDash, Coinbase, Dropbox, Instacart, Reddit.
The list goes on.
Jessica is also the author of one of the best selling books about startups, founders at work.
And hosts the social radars podcast.
She lives in England with her husband, who you may know, and her two sons.
In our conversation, we dive deep into Jessica's superpower of being the social radar.
She got this nickname in the early days of YC because she can read people incredibly well.
This becomes a huge unfair advantage when you're evaluating and investing in early stage startups and founders, but also becomes useful in every part of your life.
There's actually a quiz that I'm gonna link to in the show notes called Reading the Mind in the Eyes.
That I suggest you take to see how you do.
and it'll give you a sense of how well you are at reading people.
Jessica got a perfect score just as an example of her unique talents, reading people's emotions, along with her superpower and tips on how you can develop your own social radar. We also talk about her fabulous podcast called The Social Radars, some wild early YC stories, including how the interview with the Airbnb founders actually went down.
And so much more. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube.
It's the best way to avoid missing feature episodes and it helps the podcast.
Tremendously.
With that, I bring you Jessica Livingston.

Jessica, thank you so much for being here and welcome to the podcast.
Thanks, Lenny. I'm glad to be here.
I wanna start with a a quote.
By uh someone you may know, Paul Graham.
So he wrote

said that early on it had been a one man show.
It's sadly common to read that sort of thing.
But the problem with that description is not just that it's unfair.
It's also misleading.
Much of what's novel about Y C is due to Jessica Livingston.
If you don't know her
You don't understand
Why C.
I'm hoping with this conversation we help.
Lot more people.
Understand you.
Kind of a implication of this quote that I wanted to
ask you about is that there's an implication that you've never gotten the credit that you deserve.
For
Starting Y C for helping Y C.
become what it's become.
I'm just curious what that's been like.
For you.
That's it's sort of a hard question.
It is true.
Like
I was one of the co founders of Y Combinator and yet
I'm
Often sort of left out of
news articles
I mean
Wikipedia people
wanna take my entry off of Wikipedia.
all the time. I'm not as notable and I'm sort of like gosh, I'm a founder of Y Combinator.
Author of a best selling book on startups.
You know what does a girl have to do?
Um
But you know, uh
It's it is what it is. It's it's the external
Views.
And it's not it doesn't matter to me.
Do you know what I mean? Like people within Y C know what I've done.
The Y Combinator alumni know what I've done. My friends and family and people
I respect in the in the Silicon Valley community know what I've done, or most of them do.
So
That's fine.
But it is true. I've often been sort of erased and and in some cases
It's annoying.
because it's it's a lot of people who have a certain narrative about Y Combinator.
That
don't want me to exist. I've I've
I mean I'm m maybe
Making that up a little bit or
the people that d that sort of don't want me to be part of the the narrative are the ones that think that
why combinator only invests it's run by white men.
Only invest in white men.
And gosh, if there was a woman on the founding team making choices of who to fund
That would undermine their narrative. So I think
Sometimes that's what happens too.
Fascinating. Just a convenient.
Story to tell sometimes.
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So Y C
Your nickname was the social radar.
Uh, your podcast is called The Social Radars.
Yeah.
Talk too much about the skill.
Anywhere else?
And that's what I wanna spend our time on together is to better understand the skill that you've built of being this
Social radar.
How does that sound?
I will try, Lenny. I will try. I don't talk much about it because I don't
It's hard to talk about. I don't understand some some it's hard to put into words exactly what it is ab about.
Me, but it's true.
That my nickname at
Why combinator?
Was
The social radar.
And I think it was because my three co founders were you know deeply technical people.
And
I was not.
But I would look at other things about founders when we'd have these ten minute interviews
I would look at
Are these
Are are are the people do the co founders get along?
А зел коміти?
Do they really
know about their product, do they care? Are they gonna quit their job or
Are they telling us that they are gonna quit their job but really aren't? You know, all these little social cues.
that I'd try to pick up on
And in a lot of cases red flags
About them.
that I'd add to the decision making process. And so that's why they called me the social radar
And it just sort of stuck, and it's because I love
people and the dynamics and understanding what's motivating people.
I mean that's I I just love it and I love
founder psychology, founders personalities, I mean
I just I am absolutely fascinated with it.
I love it. Okay, so we're gonna try to unpack as much as we can with the context that you're may not exactly sure if you're able to
Articulate exactly how this power of yours works. Yes, yes, yes, yeah.
There's this uh line you wrote somewhere in Paul's written this and other people that every interview
that you all did early on at Y C. Everyone always turned to you.
And they're like, Jessica, what do you think? What does their social radar say?
Can you just talk a bit about that role that you played in the early days Y C of kind of seeing that side of
Well in the early days, especially before
I did I before I knew a lot.
As much as I know now about startups and founders, I mean, early on I was learning a lot in the first few years.
And in the first few years
You know, it was just the four of us.
So I would be in charge of
Going out.
Telling people wait here.
While we do the interview, come on in.
I'd be in charge of like the stopwatch that would time us and I'd say, Okay, our time's up and it was very
Administrative.
And I would
Observe.
Paul, Robert, and Trevor, my co-founders, would be asking them all sorts of questions about their product and their technology and blah blah blah blah blah.
I would occasionally ask questions, but I'd usually remain pretty silent.
And so I don't think people even really noticed me.
But I would be just watching them.
And sort of
Trying to observe as much as I could.
not understanding sometimes even the technology that they were talking about.
I let my co founders do that.
Um and then after
You know, we'd be talking, they'd look at me and they'd be like, Should we fund'em?
You know, Jessica, should we fund'em?
And
You know, sometimes I I could tell based on the conversation whether they
thought that the technology was good or how they felt and sometimes I'd say, absolutely we should, or I should or sometimes I'd say
Guys, you know, I'm a little nervous. Did you see how that
Founder interrupted the other founder and wouldn't let the other founder talk.
And so'cause my three co founders
Sometimes wouldn't notice this.
They'd be so caught up
In the conversation they were having about the technology
Especially Paul.
Paul would
get really into things.
And sometimes I always tease Paul'cause one of his
defining qualities is that sometimes someone would have an idea that he'd get so excited about
that by the end of the interview he'd be giving them ideas about how to grow their product and
You know, what they could become.
And they'd sit there saying
Yeah, yeah.
That's a great idea.
And then he'd say
Fun'em.
And I'd say Whoa Wow Wow Paul, you can't just
Fun this because you love the idea.
Let's take a step back and let's look
Like these two founders are working at Google and they
Don't say they're gonna quit. That's not good. You know, and I'd
point out these things that I had observed. But I mean we always agreed. It was very rare
That we wouldn't agree on.
on funding. Something we were usually on the same page.
I see.
It's interesting that you talk about these um
behaviors like
Co founders interrupting each other or being kind of aggressive here and there.
Some people believe it that's okay for founders to be like this, you know, like a lot of successful founders. Elon, for example, Steve Jobs, you're kind of assholes a lot of times.
I imagine
And I've read part of the reason you thought about just like the
type of person is you're trying to build a specific culture.
in the early days of Y C and you're gonna be around these people.
So maybe can you talk a bit about just like why that those elements were important to you and why'd you look for those
I mean I've definitely heard that
that Steve Jobs could be an asshole. I've heard stories, but I think I would have funded him because
He's so incredible. And he's so it was so smart and so interested in the product and new like I'm I'm very persuaded.
By
people who know what they're talking about and and love their product and are domain experts.
But but
I did
Consciously.
Especially early on, less so later on.
Early on I did
Sometimes tend to say
I really think this person's an asshole.
I do not want to fund them.
And we often wouldn't.
And I uh very early on when we were just funding, you know, ten, twenty, thirty
uh startups a batch, I would sometimes
I have been known to say like
I don't know if I can have dinner with them every week.
Like it was that point.
And
I don't think we've ever regretted any of those. It didn't happen all the time. That was rare.
But I just
Life's too short.
You know, life's too short and and I wanted like a nice
I wanted to be able to work with these founders.
And as it turns out, it was sort of important early on in
Weeding out
Like explicit assholes.
Because that was the basis of our Y Combinator community.
Which is now
Thousands of founders.
Now of course all the founders aren't
Oh
you know, running their company anymore, but most
I I would say like most all of the founders bring something
Useful.
And valuable to the table, so if you ask a question on
book face on our you know forum for founders
Someone is gonna be there to help you.
And it's
Amazing.
And that all started very early on there was this

Uh
You know, older batchmates.
Helping newer ones and this
this pay it forward mentality where everyone helped one another and rooted and
made introductions for each other and
I think it's a big part of our our Y Combinator community now.
So I wrote down a few of the things that you mentioned you look for and you looked for in the early days.
So let me just share a few of them and then let me s let's spend a little more time here.
So you look for did the founders get along?
Uh are they committed.
To the idea.
Are they ready to quit their job?
Uh are there any red flags?
So is there anything else that you remember you spent a lot of time thinking about or looking for or then or even now?
There's looking for in the application.
And then there's looking for in the interview.
And now
We have software.
That looks for all of the
red flag in the application that I used to do by hand.
In the application I'd look for
Just
Weird things.
Like was there
Like a
Huge.
Um
gap in the equity allocation, like did one founder have ninety nine percent and one founder have one percent?
That's weird. I'd wanna dig in on that. That doesn't feel right.
You know, are they gonna quit their job?
Um are they gonna
Move to the
Silicon Valley
You ha what are their current shareholders? Is like ninety percent of their company already owned by someone else? There are all these weird things that we like to just
flag and um and we wouldn't like necessarily not fund someone because of them.
But it's just more data, right?
So that was in the application and I'd look through all of those, but in the interview
I definitely was sort of w one thing I remember I would always look for was
When you'd have a conversation
Um with us.
Lotta times
Paul especially, but Robert and Trevor would really be
getting right into the idea and questioning you and how do you know this and what about this
And if a founder would get
Defensive
That was
Always a bad sign.
Always a bad sign. The best founders would say
You know, gosh, I have thought about it and here's what I figured out, or they just have this
Almost a tennis match and a conversation.
Rather than
closing up and feeling like, Oh, this person's
Interrogating me.
You could just sort of the the open mindedness, the flexible mindedness of people was really important.
I'd get really excited about
Domain expertise.
I mean, like my co founders, we all like loved that.
Um if someone
was fixing their own problem in a
Yeah, broken industry. We loved that. Definitely I'd look for co founder relationships and again
I'm not saying I was always right, but you could tell if
You know.
One founder
I'll give it a story. One founder
Once
We asked a question.
And one person started to respond.
And the other founder
Like
Put his arm in front of him and said
Oh
I'll answer that question.
It was just so
Weird.
That he wouldn't let his co founder speak.
We we'd have situations where we'd call people like hackers in a cage.
Where it's kind of
obvious we'd there'd be like a business founder
Business person.
Who had clearly
Like convinced
A programmer to join the team.
They were given the programmer was given like very little equity
And just we call them like programmers in a ca like
Hackers in a cage.
And
Sometimes that works out. I'm not saying it doesn't.
But I'd always try to observe like okay
Does this hacker in a cage have any
Like say in the company.
The direction of the product.
That sort of thing.'Cause
The programmer needs to have opinions, right?
So funny. I love this metaphor.
And I totally get what your what you mean.
I wanna unpack a couple of these'cause this is this is exactly where I was hoping we'd go. So this idea of looking for defensiveness.
And being open to change and being flexible. Why do you think that was
So important.
to successful founders. Why did you look for that? Why was that a predictor
Several things. First of all.
Being defensive is really bad.
If you're a startup founder,'cause you're you're always gonna get people who question you.
And it's your job to sort of
educate them if it's a new area, if you're doing you're doing something presumably pretty new.
You're always gonna have people who question it or say
Why you know that
Products already out there. Why's your bet yours better?
You have to educate them. You don't want to be defensive about it.
Also
A lot of times the first idea isn't
Bang right on.
you know, the right idea and you have to be open minded and maybe adjust it in a certain direction.
the famous like PayPal story how to how it started off being, you know, the palm pilot.
You know, or money transfer.
And
Money transfer between the palm pilots or whatever.
And then all the customers were like using a janky version on the web.
And
They were begging for this to be on the web and finally the founders said, Oh, I see, you know what most people want this for. You have to be open minded.

really is what your users want.
And so if you find someone
Is defensive.
Usually they're not open minded.
The other thing
Is it the best
Founders.
Well
Want
to learn from other people and listen to other people.
I mean
You talk to the Collison brothers?
And
Say something th they ask you a question, they're listening to your answer.
I
Yeah.
So many founders think, Oh, I can't learn from anyone, but the best founders are always
listening and having spirited debates.
about things. I mean that's part of the process.
And so I think when someone's defensive
Just a bad sign.
Yeah.
So I would look for that.
A loved one I'd find
Someone
sort of showcase that they'd
Make something happen.
No matter what.
Like they're scrappy.
They're hustlers.
I I remember
Yeah.
Uh, can I tell the story about the Airbnb interview?
Please.
Okay,'cause that was definitely one I'll never forget.
That was one that was clear.
The founders were really good.
The market had
Just
crashed basically with
All the banks.
um going out of business and everything. And so we were
Only funding
startups that we felt had like really scrappy founders and could be
cockroaches, meaning could live off of very little amounts of money, or or could charge customers and make money.
And we didn't fund that many people in that winter O nine batch.
So we're being very strict with ourselves, very disciplined about things.
And the Airbnb guys came in.
And I just remember they had
A contagious amount of energy. They just had an
energy about them, the way that they
Talked about.
There's
product which was crazy at the time staying in someone's you know
Bed?
Airbag?

famous part of the story, like we hated their idea and Paul tried to get Brian and Joe and Nate to change it.
So
We didn't even like the idea.
But I remember specifically they brought at the end, Joe brought out these like the cereal boxes, the Obama O's and Captain Crunch's or m Captain McCain's or whatever. Yeah.
Captain McCain's.
And
They were saying that
They are do.
They went to some like you know.
Costco or something and bought off brand Cheerios and off brand
Uh Cap and Grunches.
Took them out of the box.
Put them in this new box, glue gunned it shut.
And I just thought
Oh my God, these guys are really like going to great lengths for this. And for some reason it was silly, but it really appealed to me, like
They're gonna work hard to do whatever they can
To make this company succeed.
And even though we were skeptical about the idea
I mean I think we definitely
made the right bet on the founders. And it was just very clear in that interview.
I'm so happy to share that story. I was definitely gonna ask about it.
It's so funny because
I've heard that story at least a hundred times working at Airbnb. That's like
They tell the store the beginning of Airbnb.
Every chance they get at every all hands, it's like a recurring
Theme and it's
Great to hear that's basically went exactly the way they describe. Oftentimes there's like a
myth around what happened, but that's that's exactly how they describe it. No, it was a it was definitely a whole crazy story and how Paul called them to accept them and the
They were on the two eighty or something, or the one oh one and
The reception went down.
And so he didn't hear if they were accepted or not?
Well did you tell that part? No, I haven't heard that part.
Oh yeah.
That's part of the story. And and they had to keep driving to like get
uh to talk to Paul again and find out that they were accepted. Oh yeah. It was just a crazy
Interview.
The the element of the story I'm also curious about is the way Joe tells he had the box in his backpack.
And as they were walking out, Paul or years like, Hey, what's that what's that cereal box doing there?
Uh is that how wind or is it more like, hey, we have the serial thing?
I don't think
Paul and I
like looked in his backpack and asked. I think he I think there was definitely some pressure on Joe.
Not
to show us the cereal boxes. I I think Nate was really down on that.
Especially
And I think on their they were walking out the door and they're like, Hey, we just brought you little something. I think I think Joe did pull it out.
And and we had an extra like minute or so around the cereal boxes. That's how I heard about the glue gun story and everything.
But I think Joe w had been reluctant, but he
He did it.
At the end and I think it was
A good call.
It's so funny.
And after that
meeting, how what was that conversation like between you and Paul? Was it just like everyone's like, We definitely gotta do this, or was it like you being like, Hey, these guys are really interesting?
No, I think we all liked him.
We all liked him, but I remember saying
We have got to f I just remember being like we've got to fund these guys. I don't know about the idea.
Maybe they'll change their idea. Who knows?
But they
Sim
Really great. They just again the energy level and the passion
With which they spoke about
Their experience
you know, hosting.'Cause they've been around
struggling, but had been a a company with an idea for, you know, a little while before they applied to why see we were there basically their Hail Mary, their last
Resort.
Um
for them. And so
they they could tell us about their
story about how they hosted the people at a conference and there was
Definitely some magic to it.
Which was convincing.
Is there anything else along the Airbnb story that would be interesting to share while we're on that topic?
I mean the only interesting thing
As it relates to being the social radar is that there were just
Some interviews that I remember because I just thought
This is great.
Like these founders are so good. I'm totally convinced.
What they're working on might not work.
But I feel like
It's so worth the bet.
Um, based on these founders. And that happened there were
Definitely a couple other
of our top most successful company that I clearly
felt that way about. You just feel like they know what they're talking about. They
Thought the problem
They're not
Solving this problem because it's
Sort of uh
The
problem du jour or
fun and exciting. Like some are very unsexy problems, like
You know, when Parker Conrad applied with Zeniths.
You know?
Unsexy HR stuff.
Benefit stuff.
But he
knew how broken it was and was trying to fix it.
And I love
stories like that. You know, there's one story
In terms of the one time I did sort of persuade the rest of the group
To fund someone.
Was
Do you know the company Goat?
The sneaker.
Absolutely.
Okay.
When
Eddie and Darshan applied, they were not doing the sneaker company.
They were doing this
Group.
Sort of book a
Book a group dinner at a restaurant with people you don't know.
As a way to meet new people.
And for some reason I love the idea'cause I thought maybe it could be like a secret
dating like a Trojan horse for dating sort of sight. But I really loved
The two founders and one of the reasons again they
had this passion about their idea.
But
They had work they had had like these
This cream puff company?
before that they had run and they just told these stories about how hard it was and they
All this stuff and I for some reason just
But
These are hustlers.
These guys are scrappy. They're gonna make this succeed.
And
They didn't make the that company succeed.
But they pivoted.
and made Goat Succeed and it's doing really, really well. And I remember that one I definitely
Had
I mean not that
Paul, Robert, and Trevor didn't like them, but I think they really didn't think the idea was that great, or just sort of were Matt was like, We have to fund them.
I love sharing these stories. If you have more to share, please keep throwing'em out there.
So a few things I've
Noted so far of things that you look for. And I think it's important to note
This is very early stage evaluation.
where the founder and the team is it's it's incredibly important because the idea
Up it shifts.
Oh yeah.
This is as early as it gets, Lenny.
Yeah.
Oftentimes just a just an idea, I imagine.
Yes.
So a few things. So so far, things that you found to be really
Uh
Valuable to look for.
One is uh
This idea of making just making shit happen, showing signs of being hustlers, just like getting shit done.
Obama's
Things like that. And then I think along the same lines just like passion for this
for this idea and just like carry almost charisma, is that is that how you think about it, or is it just like
I hate using the word charisma.
Because
I wouldn't w there are a lot of charismatic people who are
Or full of baloney.
And and are just doing a start up because it's a cool thing to do now. And I wouldn't want anyone to get
Fooled by charisma.
There has to be some substance behind that charisma. Of course, we all love talking to more charismatic people.
And I've been.
Certainly talk to my
fair share of totally uncharismatic people. But sometimes
They're really good founders, too.
You know, if they know what they're doing and
Care about the user
And are fixing a problem that they
You know, have a deep connection to
So I don't want to say someone
His charismatic.
But
It definitely helps because as you know, as a founder
You have to do a lot of sales and you have to recruit people and you have to convince investors
To fund you and
You have to convince users to use your product and all this stuff. See it does help.
It does help being charismatic, definitely.
So Okay, so there's being like super hustler making shit happen.
Domain expertise, something you've mentioned a few times, just like having deep
domain expertise in area and I think
That's probably where they probably don't pivot oftentimes where they've actually have experience in that specific problem.
They might a little bit.
They might pivot a little in terms of the actual solution.
They might be trying to solve a problem and the first attempt doesn't really work.
I haven't mentioned earnestness, though.
Oh.
Do tell.
Earnestness is like one of the most
Important because
Ernest sort of to me is bucketed with authenticity.
And
To be a successful startup founder you have to care so much about
The problem you're trying to solve.
The users you're serving
And
Being earnest about it.
Is so key to success. Мінер со мані
wanna be founders. So many people
Doing it'cause it's cool.
Or they think
You know, this
idea's cool, but they don't really deep down
Have what it takes.
And I think I we always try to find earnest people.
What does Ernest look like?
In practice.
How does that come across?
Think it means being like sort of humble.
About
You know, and if if you get asked a question
In the interview and you don't know the answer.
They say
You know?
I don't know the answer to that.
I'd have to think about it.
Or I don't know the answer.
I've I've given it some thought and here's what I have come up with and they're just
honest about things and they're not trying to sort of
do whole smoke and mirrors thing, which we've definitely gotten people like that that like avoid the question or
Or doing it for the wrong reasons. I mean
Yeah, I do I remember there were just there was one
group that were like
Forty five year old men.
And they were building
An app
For like
Teenage.
Teenagers and fashion.
And I remember just thinking
I we're asking them, why have you chosen
teenagers in fashion. It was so clear that they thought they could make
Easy money.
And it wasn't because they cared about fashion.
It wasn't because
Oh I have
You know, a daughter is really into fashion and I've seen this neat It was just like
They made up the idea.
You know?
And I I that is not
Ernest, that is not authentic to me.
You talked about so there's this
Earnestness you look for also not being defensive.
Kind of on there's this also spectrum of confidence.
And people believing in what they're doing.
Do you have any thoughts on just how to find that like what does that look like when they're
too defensive versus they're just confident and they know it through.
Talking about it.
You definitely want confidence. I mean it's hard to
I think you can
See it when you experience it.
Like someone you can
Someone who's
confident in answering your questions, but isn't defensive, there's definitely a difference.
And I don't know, this is why I'm saying it's sort of hard to articulate these things.
But confidence means you can say
I've thought about that and I don't know the answer.
Like that's confidence.
You know, and they'll say, But here's what I do to try to figure it out.
Here are my plans.
to do th to address that.
Yeah, confidence.
Like is is I should've put that up front'cause that's very important, especially when it comes to
fundraising, you gotta have you you cannot go into an investor meeting.
Lacking confidence. You can come into Y C's interview Lacking Confidence.
But we will then help you and then
Next three months.
And
By the way.
One of the things we do to help people gain more confidence
Is to make them believe that they're
Their startup is a great investment.
To help them like create a startup that truly is
Possibly gonna make money, or at least worth
being a good bet.
That's the thing. Early stage.
The best you can offer is
Like I might not succeed.
But I'm
Definitely a good bet.
And
Yeah, we help them.
with their product, we help them with their ideas and
We helped them that by demo day.
They can get up on stage and legitimately say
We're a good bet, and here's why. Let me tell you about our idea.
And so we definitely I help with confidence.
Awesome.
A couple other things you mentioned earlier, just to unpack a little bit. So
Being committed is something you look for.
And co founders getting along.
In terms of committed.
Imagine these are like very practical
Things right, like how are they actually gonna stick to this? Are they actually excited to work on this? Maybe talk about that a little bit.
We all know how hard startups are.
But I think you don't really know how hard it is until you actually do it.
Lot of people would start a startup
still having a job at Google or wherever.
And they do it on the side.'Cause I I do recommend if people are just getting started.
and don't want to raise money yet, st you know, starting it on the side's a great way to get going.
But at some point you have to commit. You have to burn the boat.
Because we found that
Founders who were still getting a paycheck and health insurance
Once the going got tough
Uh
They did not quit their job.
And and you need that
Deter like you sort of need that desperation. Like I I have to make this startup succeed.
Because that
It's my job.
You know, not like oh I'll just stay at Google.
You need that.
And we found that founders who weren't leaving their jobs, it was just not working out. Or like that co founder would always wind up leaving the company.
'Cause they didn't want to actually leave their job.
And
You know, that's fine. There are people that
Can't leave their jobs for financial reasons, that's fine.
You just shouldn't be starting a startup if you're not.
gonna be prepared to leave your job.
So that's the the leaving of the job thing.
And the co founders getting along
I mean, oh my.
I spent a lot of my time at Y Combinator when I was there all the time.
Full time.
Yeah, help.
Mediating.
Co founder disputes. And
So many startups
Died.
Or had near death experiences because the f co founders didn't get along or broke up.
It just happens all the time.
And so that's why I think during interviews I was
Desperately trying to search for
Any clues.
That the co founders didn't get along.
Or if they like
Blatantly contradicted each other.
But you could also tell
If they were answering, you know, finishing each other's sentences.
You know, like I love co founders that have a history together.
Either
They went to school together, they went to college together.
Work together.
Maybe there are siblings.
'Cause when you have a a long term relationship
You trust each other and you know each other's weaknesses and
You have the same you're usually on the same page
You know, with your
aspirations and everything, it's really scary when two founders get together just to start the startup.
And don't have any history. That that
Massive red flag.
Sometimes it works out.
Like in the case of Dropbox.
Drew and Arash, you know, both went to MIT, but I think
They didn't know each other.
Before they started Dropbox.
And it worked out.
But most of the time.
It doesn't.
So we've talked about co founders getting along, looking for defensiveness, domain expertise.
The sign of making shit happen.
Earnestness.
There anything else that we miss that you look for in
the founders that tell you maybe we should, maybe we shouldn't.
Relentlessly resourceful.
I mean that's sort of Paul wrote a whole essay on that.
Yeah.
Every founder is different. I never try to say, Oh, this person doesn't have this, I'm not gonna fund them.
You always have to everyone's different.
But I mean, you're an investor. I'm curious, do you I mean, do any of these things surprise you or do you care about these things too?
Absolutely, absolutely.
Okay.
And I I I actually try to avoid pre seed and early early stage'cause
I'm not amazing at it.
Maybe.
Uh, this is why I wanna learn how to build my social readers killing. Gosh, okay.
Yeah. Tough. It's so tough. It's like so few things actually work out and Well it's because you don't have a lot of data. If someone is just applying with an idea
You have very little data. You can look at
Where they went to college.
What have they built?
In the past, that's always a great predictor.
Of their ability.
And so on the on Y C's application we asked them what
What project have you worked on before, or whatever?
But it's really hard to tell.
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When did you first
Noticed that you had this social radar ish skill.
And you're better at this than other people.
Paul used to always call me Detective Livingston.
Before I was a social radar, I was Detective Livingston.
Like I
Cannot help myself.
Noticing weird thing. Like
Just dumb things like if Paul like
Had on a yellow T shirt.
And then an hour later came in with a blue T shirt.
I'd be like
Why do you have a blue t shirt on? Like I can't I have to
I have to understand what happened in that hour.
Where that T shirt is different.
Yeah, I just
Or people's like what

Relationships what drives them.
I was always like this, and I think it goes back to my childhood.
Like I spent
Hours and hours on the phone with people with my
Girlfriends like dissecting situations and then
All through high school and college. I mean
The amount of time
We wasted
like discussing social matters with people and boys and things like that.
It was just
frightening how much time I wasted, but I just was genuinely
interested in it and what drives people and why did this happen and
I don't know when if I ever noticed I did this, but it was just my point is it's always been a part of me.
And I definitely notice
And have an aversion to like phony people. Like I
I always have. I've never been one to fall.
For like
Someone who's super phony and like
tried to have him as a friend or anything. I just can tell and ugh I hate it.
Do you feel like it was it's
Like almost all genetic, or do you think there's something in your childhood that
pushed you to be good at this.
I don't know.
I really don't know.
I w see this is why I think I'm gonna be
A bad guess'cause I can't give practical
I can't give a practical understanding. I mean I don't
Really think.
It's you know, I can't say other people in my family are like that and I can't say
That it was part of my upbringing.
It just it I just noticed these things. I don't know.
I mean I should be paying attention to other things.
But I'm not.
But I'm paying attention to this, like
I'll give you an example.
So
I looked up
Your bio.
To read a little bit about you.
And I I loved the Dalton Caldwell.
Uh, podcast. I listen to that.
Fourth most popular of all time.
Dalton's was?
Yes.
Oh, go Dalton. That's awesome.
Yeah, it was really good. I really like I learned a lot from it. I love listening to Dalton.
But like what I really want to know about you is on
the release that you sent or on the like instructions for this podcast you said
There might be some edge cases where
Your podcast isn't good enough to go out. We just want to warn you.
And like all I could think of was like what prompted that
Who who who there has to be a story of what prompted that.
No one else would pay attention to that, but I'm just
So curious. It's like
It's so weird. I'm just a weird person like this.
Uh yes. I did add that. There's a story basically it's just uh

Uh we didn't have that caveat in the in the
prep beforehand and it felt bad to
Tell the person.
See, I knew it. I knew that that had happened.
Exactly right.
Is there a kind of a way you've thought about honing this skill over time? Like once you kind of got a sense, I people keep telling me I'm really good at this, is there something you've done to help?
Strengthen it.
No
But
One of the things I do try to do is
Sort of.
reinforce like sometimes I'll have a
A feeling about someone.
Maybe we fund them, maybe we don't.
Sort of like to know.
what happens a few years later I like to follow up.
Like there there definitely have been some situations where
I
haven't liked someone that we funded.
And it's taken, you know
Five to ten years before they failed.
And in some cases like
For a bad reason.
You know, where I'll say
Oh.
I w thank God I was right about that.
I did have this feeling, or
You know, I knew they'd be successful.
And like the
The goat guys who I was saying before.
There was definitely a period when Grub with Us their first startup wasn't doing well.
And they were starting the like that maybe some people would have given up on them.
You know
And and now I can say, you know, I was right about them. That feeling was right. So I do try to sort of
Follow up with some of the
the really strong gut instincts that I had to see if I was right. I often
Often when I have a gut instinct it's like a negative thing.
So we wind up not funding someone. So I really need to know
If that
person went on to be super successful.
And I I will answer your question right now.
There's no one
That I
had a strong dislike for
That I sort of said we we should not fund them.
That has gone on to be a super success.
Thank God.
Interesting. I mean it doesn't happen all the time that I
really put my foot down. But sometimes I have.
And is the is this feeling is it like a visceral body thing for you, or is it like intellectually you're like notice, hey, this guy's interrupting her and this
More intellectual.
But it it does come from inside. Like I can't
I don't know how to hone it.
I can't it has to come natural. It you have to have a natural interest in
Sort of
people. And so I'm sometimes not listening to all the words and I'm sort of just
Observing them. I don't know.
Have you
Ever been tricked?
By someone where you didn't see something you should have seen. Is there anything there?
Oh yeah, for sure.
I can't r really talk about the times I have been tricked just'cause I don't want to say anything.
really negative about people.
But
There was well, there's one example that I do feel
comfortable sharing. Um
Ilia Lichtenstein.
Of
Mixed rank.
Do you know the guy that like stole billions of dollars in Bitcoin from a crypto wallet?
Do you not know this crazy, crazy story like I I think is in the joint now.
He was definitely convicted.
Of this and his wife
And they stole like
Billions of dollars.
Yeah.
And
You know I
Definitely.
Don't remember.
Thinking anything.
You know, bad l about him.
You know, or thinking he could be that kind of person.
Mm. So that definitely there have been some some doozies like that where
Did not see that one coming.
Oh my god.
I think what's extraordinary about
The fact that that happens rarely.
Is that your interviews are ten minutes long.
And so
Very little time to actually.

And plus their actual product and idea and
growth strategy and all these things.
Well you find
you know, a lot can come in reading the application. That's a lot of leg work at the beginning. You read the application. But then the ten minutes

As long as you need
In most cases.
'Cause we found when they were longer, like twenty minutes, you'd know in ten minutes and be like twiddling your thumbs.
trying to get through the interview for the next ten minutes. So we kept them short so we could interview more people.
But
There have definitely been cases where we've interviewed people, accepted them.
And then very soon afterward we're sort of like
Oh, like sort of crestfallen like
Oh, these people are very limp.
This what were we thinking?
Definitely.
We've been tricked in that respect.
All the time.
Or
Oh gosh.
They seemed so impressive in the interview and now
They're just posers, you know, and can't really do anything. Like definitely we're tr I'm tricked all the time in little ways.
Or
Like I didn't
Noticed two founders didn't get along and then
you know, one co founder goes missing, you know, a week into the program or something crazy. There's all sorts of crazy
Stuff like that that happened.
I I think uh in in the game you're playing, uh
It's a
Uh I would expect some some things to slip through.
Yeah. You said that.
there's been kind of an operationalization of some of the things you used to look for in founders now that you're not actually in the process.
There's kinda is there like like a Jessica as a service?
What what kind of stuff have they built that
Looks for the sorts of things you used to look for in the interview process.
No, it's all just stuff
In the application that automatically like flags
certain things. I I actually don't remember all of them.
But it's just
All it is is is a
Please pay attention to this reader of the application. It's not
This disqualifies anyone, it's just
Please pay attention.
And those are things like I mentioned
like a really crazy equity structure.
Founders not quitting their job.
Things like that.

It's important that someone is
Voting on them
And then
Interviewing them.
No.
'cause I would often some of the questions I'd ask
At the end of the interview I'd say.
It looks like you know, you have ninety percent of the stock and your co founder only has one.
Can you tell us why that's the case?
And maybe they could make a case for it.
You know, who knows?
I you know, but at least I'd ask.
So the the flags just say
Pay attention to it.
Amazing.
So if we were to zoom out.
In early stage investing.
The main
thing you need to get right and evaluate is the founder.
The social radar skill that you've
Had
From childhood.
uh is such an incredible advantage in doing this well and you could
Basically say Y C is what it is.
Because of this
unfair advantage that you all had in the early days.
I'm guessing many people
Listening to this are like I wanna we need a Jessica on our team. We need to build this skill ourselves. We need to figure out how to
Integrate social radaring into our process. I know you're gonna hate this question, but just
Do you have any advice for people that want to try to
Build the skill, get better at this.
notice some of these things.
I really think that our advantage was that my three co founders were deeply technical.
uh people.
And I think a lot of investors
Back then.
You know, weren't you?
A lot, you know, didn't have that background, and I think that that background
really helped um Y C
Cheers.
Good founders. So I I don't I don't want it to
Make it sound like
You know.
It was that big of a deal. But
Advice.
Advice for how to hone

Try to pay attention to subtle cues. If you really feel like
Gosh, I'm so clueless about these things.
Try to just tell yourself, Okay, I'm gonna go in I'm going in to evaluate these founders, evaluate this
Investment opportunity.
I know I'm bad at
these kind of judgments I'm gonna remember like
Do they seem like they get along?
'Cause there are no like trick questions. I don't have any trick questions that you could ask.
Or it's just paying attention. Like have a conversation.
Do they understand their product well?
Are they defensive? Like maybe have your own little checklist.
That you think about you don't have to have it written down, but you think about
And then afterward
You spend some time thinking like were they defensive? Like when I asked them
Why this is better than the competitor.
How did that go?
Or ask them, maybe do have some questions like
If you don't know how long they've known each other
Ask them that question.
How did you two meet?
How did you have have you ever worked together before?
How's it going?
P
A little bit more conscious about asking these types of questions to reveal
Like some key
information for your investment decision.
That was an awesome summary of a lot of the stuff we talked about.
If anyone ever doubts that you are very good at this, uh, Paul tweeted this
quiz the reading the mind in the eyes quiz
that I took. It's incredibly hard. You basically see a bunch of eyes and you're supposed to judge
uh their motion.
And uh
It's really hard. And you got thirty six out of thirty six.
Which blows my mind.
I did nail it. I do I do have to tell a funny story about this. So Paul
Sort of like late at night.
And he emailed me'cause I had like gone to bed, but I had my
And he emailed me, he's like, Check out this quiz.
I got twenty five out of thirty six.
What are what can you get? So I got my computer out'cause I was like, I have to beat Paul.
And I did it.
And it was really hard, like they'd only show the eyes.
And then it would say, What is this person
Thinking.
Are they.
Happy
Sad.
But some of them were really hard to distinguish. Are they irritated or are they angry?
Like it's kinda hard to tell the difference between irritated and angry.
And I remember
Like
Say looking into these people uh
People's eyes saying
What are they trying to communicate to me?
Are they irritated with me?
Or they madden me, kind of thing.
And as I went through would tell you if you got
Got it correct.
And as I almost got to the end, I was like Oh my God, this is gonna be a near perfect score. I have to nail this.
And when I got thirty six out of thirty six, I was like, Yes, and I told Paul
He tweeted it.
We then like a week later
had this Y C event in London.
And I swear to God
About ten people came up to me to talk about this I quiz and how they had not done well and what was my secret. It was very amusing. I never thought that
Anyone would think it would
Uh that interesting.
I love that there's this thing that totally shows this skill you have.
that is better than everyone else. I I took it every all my friends have taken it after that tweet and
Uh the highest we've gotten is thirty one of all the people I know.
Really?
Yeah. And and I think when people take it, we'll link to it, they're gonna be like, How can you get thirty six out of thirty six?
You have to look into their eyes and say, What are they trying to tell me?
You're I hope you're not trying to tell me like you're full of shit.
What here I'm feeling despondent. Just kidding, that's one of the options. I'm like, what does that even mean?
I know. Well that's the other thing. I told Paul
Also the challenge is you really have to understand
What each
Like
Feeling.
What that word means. He's like, Oh, that didn't even occur to me'cause he's such a word person and knows like
the exact definition of every single word.
But I thought some people will struggle understanding
The complexities of the
The emotion.
Yeah.
I've I've with the words I almost felt like I had to do what you did were just like what does this word feel like when I'm reading it? The spondit.
Let's see if these eyes are despondent.
I love that trick you shirt. So basically you looked at the eyes and you're like, What is this person trying to tell me?
Yeah.
That's the best I could do.
Amazing. So we're gonna link to that quiz. I'm curious what people if you uh if you take it, please leave your score in the comments.
See if anyone can get anywhere near.
Jessica Score.
Okay, so speaking of social radaring, you have a podcast called The Social Radarist.
Yeah, let's talk about it.
Okay. Um yes. First of all, just why did you decide to start a podcast? There's a lot of podcasts in the world. What made you decide to start one? Well, I'm really excited that you're asking that question'cause no one has ever asked me about the social radars. Yes. I mean it's pretty new, but we launched last year.
I decided to start the social radars because I live off in the English countryside, not really.
As connected as I'd like to be with Silicon Valley,
Partly by choice, but I do I do miss it a lot.
And I was finding that as I was catching up with
Why C alumni.
You know, that would come visit or I'd see
I just loved
The conversations we were having, and I missed that. I missed that connection with these people.
And sort of sharing their stories of triumph.
And failure in some cases, but mostly triumph.
At the same time
I became obsessed with this podcast called Smartless. Have you ever heard of it?
I've heard of it. I haven't listened.
Okay.
So
Just for the listeners.
It is
A podcast hosted by three actors, Jason Batman, Will Arnett, and Sean Hayes.
And they really they invite
Hollywood people, actors, directors, musicians, sometimes athletes.
On the show
And
The thing is one person, one of the hosts
invites the guests, the other two don't know.
So there's no preparation.
And it's the most
fascinating thing. I love movies and I love television and I can tell you
Like another weird eccentric
sort of gift of mine is I remember every name in Hollywood and know all like their children and all this this stuff,'cause I've been reading people magazines since I was thirteen.
So
I loved
Like you'd learn so much about the actors as a people'cause they weren't
Talking from a script or their, you know, media messages for th promoting a movie. It was like
Just genuine conversations.
Most of the time these actors knew the people and were friends.
And I just found it fascinating.
I could not stop en and
I thought
There should be
like a really informal conversation like this with startup founders so people could
Understand the people behind the startups.
And it's not

To
Maybe I don't want to say professional'cause I hope it's professional sounding, but it's
It's very conversational.
And authentic.
And I was trying to
mimic that a little bit. So I
I convinced my colleague and friend Carolyn Levy, who of course has a full time
Job being
one of the amazing lawyers with NYC.
And she's super busy.
I convinced her to to do it with me.
So I could have a partner in crime.
And then
We just started and I said
We'll do a few episodes, see how it goes.
And
We'll keep going if it's fun.
And I have had
So much fun.
Catching up with all the people I've interviewed. I mean, at this point, I forget how many
Podcasts I've even done, but maybe I'm not sure.
Twenty seven that have launched yet.
And there's a few in there's a few coming out season three, we're still in the middle of that. I'm still editing some and doing some.
But it's been so much fun and I love it, and I hope
That people
Enjoy
Listening, I hope I'm not just working this really small corner of the room.
I hope people enjoy sort of unstructured
uh conversations.
People open up to me though because
What I copied from Smart List
That I liked.
You know, they'd say, Hey, remember when we were at that
Oscar's party and this happened.
Like because they had that relationship with the people they're interviewing
in a lot of cases. I feel like I've had that with a lot of people I'm interviewing and I could say
Hey Brian.
Remember when you interviewed and brought the cereal boxes?
You know, and he could
Tell he shared that story.
I don't think I knew it before then that they were on the w one oh one and
The phone went out, you know, the reception went out before
Paul said that they were accepted.
So I learn a lot and it's really just fascinating to me.
Well it's an awesome podcast I've been I've been listening. I'm gonna just read us some of the guests that you've had on just so people get a sense of who you're interviewing.
Uh so you actually just had Paul Graham on the podcast. He does a very few
Podcast episodes. So that's
an unfair advantage you have there.
Patrick and John Collison, Brian Chesky.
You mentioned Brian Armstrong, Emmett Shear.
Tony Zoo. Like
Epic people.
Em it chair, by the way.
The week after he was named.
Open AI CEO for like seventy two hours. That one launched. I was like, I could not have planned that timing better.
Is there an episode you'd recommend people
start with if they were to start to
Explore your podcast and get into it.
Honestly, like I truly
believe this, I'm not BSing you. I think they're all really, really good.
And there's so many interesting takeaways from every single one. If I were coming to it for the first time, I'd probably choose I'd look at the guests and say,
Who am I interested? Have I stayed at an Airbnb and I wanna learn more about that? Or do I use Reddit?
Some uh just see who the guests are and start with someone you're kinda interested in.
And I guarantee you'll like learn more about this person.
So across the podcast episodes you've done I hate when people ask me this question, but I'm gonna ask you this question. Is there
Anything you've got.
Any big lessons you've learned, any stories that have stuck with you, any takeaways so far from interviewing all these incredibly
successful founders and people. My God, I love that question. I don't hate that question. Okay, I'm glad I I could talk for an hour just on I wanna like learn from you as an expert podcaster,'cause I'm still a noob here.
What I've learned the hard way.
And you're probably will nod your head when I say this is that I'm
I talk way too much.
I'm a huge wind bag and I
He I
Don't notice it now when I'm just
Talking to you and going off and talking, talking, talking but
When I'm editing the podcast and I'm listening to myself.
Ask a question.
And
twenty sentences when I could ask it in two.
So I've
Really had to train myself.
To keep
things short. Like you want
You want like regular short dialogue.
You know, you know this.
But
You also have to interrupt guests if they're going off too much. So so like
The talking of the host should be
Frequent but short.
That's the lesson that I've learned.
Totally.
Well content.
I mean every
Every single episode.
Is a gem.
in its own right. And there aren't like
Massive lessons cause it's
They're all sort of specific to that.
person and I never know exactly which direction we're gonna go in.
Um when we get into things.
But it was interesting. There were definitely some themes.
with like Adora Chung and Tony Zhu of
Um
Door dash.
Where they said they really made a mistake early on.
Scaling into different cities.
Before they had nailed.
You know
The original city.
And
That you know, that's an important lesson. There's lessons for everyone, I think, in addition to really getting to know
these founders their personal side
of their personality, there's some great lessons that they all tell.
I love these lessons.
Is there anything else you've learned about interviewing? That's something I'm always trying to
Get better at. I love this tr point you made. I complet I say the same thing to every podcaster. You talk too much as a host. You should
Let the guest up.
Just ask the question and let him know.
Is there anything else that you've learned about just how to interview
More effectively.
Remember I've been interviewing people
since YC started.
Um
'Cause I was working on founders at work.
one one simultaneously when we started Y C and so that was a collection of interviews.
And back then I can't say I was that good at it. I've gotten much better. And then I've since gone. I did I used to do a lot of interviews at startup school on stage with people.
And now the podcast.
I think
One thing.
That
Is that the guests trust me
They trust that I'm not
gonna try to like have a gotcha moment. I'm not trying to lure them into saying anything controversial.
I mean, do I love it when they say something that hasn't been said before? Yes.
But I'm not trying to trick them.
And just like you, I tell them
You will have a chance to review this.
Before it goes public.
And I think that
disarms people and they say okay I can open up because I know
If I regret saying something
It's not like talking to a reporter who's gonna re who's gonna publish it.
Like I care about them, I care about making them look good.
А невер вона betray their trust.
And they know that. So that's
Part of it too.
For me with the podcast, I just ta I have some questions that I do ahead of time just so I have something.
Down.
But I also just let

where it's going. And we get in we
Get into some random tangents.
That I find are really fascinating.
Is there a story that stands out to you just like that sticks with you from the interviews that just like wow, that was such an incredible story someone shared with me or a lesson or
The podcast that really sticks with me.
Is the Parker Conrad.
Uh
Yeah episode.
Of
Rippling?
But we spent a lot of time on Zenopits.
Because if you didn't follow
uh that story years ago.
The press annihilated him.
And in talking to him I
I learned why.
There was a smear campaign,
You know.
Paid for the
By someone still at Zenfits.
There were
Legal threats?
Made
To force him
To
Sign and you know not s sign the stuck
sign this um legal document that would allow them to
Have a non compete in California.
So that he couldn't start another company?
Basically making his life miserable, disparaging him.
stories planted in the press and I had him come on and I had him tell what were the what really happened.
You know?
And I
Even I
Who have seen
So much shit.
behind the scenes
with startups in Silicon Valley over the years, like
Stuff you just couldn't believe.
This was unbelievable.
And
The thing that really sticks with me is that like
No reporter ever
Like
Uh maybe no reporters listen to it.
But
No one said like, Hey, I got that wrong years ago. I shouldn't have written that.
That wasn't true. Let me set the record straight.
So
He doesn't care.
And Parker's moved on. He's successful with
Ripling, he doesn't think about this stuff.
But I do. I care about justice, you know, and it was
A horrible thing that was done to him.
And like it
It affected his health, it affected his
Lice
You know?
And
I just I'm glad to have sort of
been a conduit to set the record straight.
That's an awesome episode maybe for people to
Start with the podcast.
And then generally I just love this rise of uh
Ways for tech people to share their story.
Without
The
drive to like create clic and create gotcha moments and things like that. Just this this I think people call a techno optimism, this idea of just like tech is great. Technology is doing great things for us.
Let's just tell these stories in a really positive way versus
Look at all the harm they're causing technology. Stop slow it down.
I just and I just wanna have conversations that I personally find interesting. I'm very selfish about it, Lenny.
As long as I have an interesting conversation, I tell Carolyn this all the time.
Like as long as we have like twenty listeners.
That's all I need.
Twenty like really interested listeners.
Um
Oh we'll keep doing it.
I I love that attitude. I wish I had that the same feeling. I what I look for is is it growing. That's the thing I'm like, Is it growing at least? If it's growing.
No matter what it is, I'm feeling good. I need to be a little bit more like that. I don't know any of my statistics.
What should I what statistics
You tell me as a
Experience podcaster.
What statistics should I be
Like have taped up to my mirror every day and track.
There's like the correct one and there's like there's the simple one that I look at, which is just downloads of the episode. Like it's it's like the most basic one you see everywhere.
But
And it downloads is a weird one'cause they might download it not listen to it, but that's just the one that podcast platforms
Tell you how many people have downloaded it.
And
That's the one.
That's the one that just tells you kind of generally.
Are people listening? Are people continuing to listen to the cut?
Did they remove it from their phone?
Like in theory you should be looking at retention, like how many people are finishing the podcast episode.
Can you tell that though? I thought these
Platforms don't share that with you.
Some do, some do. Spotify gives you some of that Apple.
Yeah, there's
There's uh
The worst part about podcasting is the analytics are extremely bad.
And inconsistent.
But there's some of the stats.
The other one, okay, here's one to pay attention to is number of subscribers.
on the different platforms. People that follow you. That actually is a really important metric to watch.
Number of subscribers. Okay. One thing I also
This is just my personality.
I can't bring myself to do what I want to.
Is ask people.
If you like the social radars like
Please subscribe.
And leave a rating.
And a review. Like
I would do anything to have people leave rating and reviews.
Okay, if you're listening and you
Either check out the podcast or you're already a listener, please
Leave a rating and a review and subscribe and follow.
Thank you.
Can I ask you a question about podcasting really quickly?
Let's do it.
After you hang up with a person, can you tell do you have a gut instinct like
Oh, that was a really great one.
It's interesting is the ones that I sometimes think holy moly, that was incredible.
Don't do as well as I would think.
And sometimes ones I don't I think but didn't go amazing actually do a lot better than I think.
And I think there's like a difference between the energy and the
Fan.
versus like the content and the interesting and value of the actual conversation.
And so sometimes you feel like that was so fun, so good, I loved it.
But people are like, nah, I didn't learn anything.
So those are interesting that's something I've learned.
Okay, yeah,'cause people come to yours expecting to learn things.
Now I'm getting now I'm a little nervous. I'm gonna get acts'cause I'm not teaching them anything.
You you're so modest. Uh this was
Incredible. I think we've taught people a lot of really
Important and really actionable things and I know you don't think you did.
But you did.
And with that
We've covered a ton of ground.
We've talked through every single thing that I was hoping we talked through. Is there anything else you wanted to share?
Or maybe leave listeners with before we get to our very exciting lightning round.
No, I mean, honestly, I
I can't think of
I think I I win bagged
Enough.
This was incredible.
You talked.
Exactly the right amount of time.
With that we reached our very exciting lightning round. I've got six questions for you. Are you ready?
Ready as I'll ever be.
Okay.
First question, what are two or three books that you recommended most to other people?
Well, I definitely would recommend like my first, second and third books would all be P G Woodhouse books.
Do you do you know him as an author, Ask Jeeves?
Okay.
So he was an
You know.
Old old school author and he wrote
The Ask Jeeves books.
About
the you know butler and
Not the Wester.
And it they're so funny.
They're they're just
And
Fabulously written. Like his use of words
Makes me laugh so hard.
And so I would specifically recommend like the starter books that I'd wr he he wrote
Tons of books and he lived till he was like a hundred.
Hm.
Re start with like
Very good Jeeves or
Um
right ho Jeeves, carry on Jeeves.
Those three.
Um
Are really good.
Good books.
I tend to read so Paul's the big reader.
In the family he reads, you know
riveting books like on Roman Greens and
Anything that has to do with medieval history.
I tend to read biographies of people, and so
I
I just uh especially musicians.
Um, specially English musicians, strangely. And so I've recommended to a lot of people if you really want a good autobiography,'cause I sometimes
hate autobiographies'cause I feel feel like people hold back.
And don't really share.
Everything.
Um, Keith Richards, his autobiography called Life
is really good if you're a fan of the Rolling Stones at all.
That was really good. And then
I recently read Barbara Streisand's biography called
I think it's called My Name is Barbara.
Something and
I kept thinking as I was reading this
Like every female founder
should read this book.
And you're looking at me like that's so random.
But
It's because
She
was such a success within this totally male dominated like world of Hollywood.
And just treated like
Garbage.
And dismissed and
You know, called a diva when she was very particular about something.
Whereas a man
Would be called you know.
uh you know, a great director and she was called a diva.
And I felt like every woman should just read this to inspire them. It was such a great book. Long, but very good.
Incredible recommendations.
Next question, do you have a favorite recent movie or T V show?
I don't have to watch recent movies I watch
Old school movies like from the fifties
Through the nineties and stuff.
My favorite new T V show
Just off the top of my head right now.
Is Clarkson's farm.
Have you heard of that on Amazon? No
Jeremy Clarkson, he's in what in a show called Top Gear.
I don't watch that, but
He
Lives out.
In in the English countryside.
He has a farm and he decided that
He'd farm it.
And the whole show is about him getting into this business
That he knows nothing about
Everything goes wrong.
But it is hysterical.
And heartbreaking at the same time. I've learned so much about England and
about where I live and the the crops that are grown and how hard it is for farmers. He's really shown a light
On the difficulty of being
A farmer these days and it's
Fabulous. Clarkson's farm.
And it's I it's a good it has some like bad language in it, but I do recommend that kids watch it.
'Cause it's it's just a good it's a good show to watch as a family.
If you can deal with a little
You know, foul language.
Fell language, the Brits.
Say uh drop a lot of F bombs.
Do you have a favorite life motto that you

Share with people.
Find useful in work or in life.
So boring, but I always try to treat people the way
I'd like to be treated myself.
Really.
Is fundamental.
Life lesson.
It's like boring but so
powerful and important. So I and I I I try to live that same way.
And I think it's a good reminder to people. Sometimes the most
Think it was Michael Pollen that said the cliches are.
Cliche'cause'cause they're so true. They're like so true, we're tired of hearing it.
Sometimes it's important to be reminded of them.
Who's most influenced you?
In your career.
Who do you think of when you're like, This person's really had the most influence on me.
In my career I definitely have to say
My husband.
Paul Graham.
I've just learned so much from him.
Over the years.
And he's such he's such a good person and I don't
I think
People who know him.
All know that he is?
It's just he has such a big
online personality either through Twitter.
Or through his essays.
And so
He has a lot of people that don't like him.
'Cause he also
Speaks what he believes.
And he is not afraid.
to say anything if he believes it's true.
And needs to be said.
Whereas I'm the exact opposite, I'm like, Oh, I'm not
Going near that. I'm not touching that with a ten foot pole. I don't even want to get in someone's crosshairs.
Or fight with someone.
And
I admire that so much. Like there's so much that he's done
With Y combinator and just
in our personal life that is just so
Admirable. And I I just
I've really learned
learned a lot from him. It's such a boring thing to like learn.
But
At the same time.
I'm gonna extend this. I'm gonna win bag a little bit longer.
I have learned so much from the
Founders that we funded.
I mean some of them are just incre
Incredible people.
And
And have been through so much and survived so much and
built these amazing companies that I couldn't have even imagined when we funded them.
that these companies would be
As successful as they are, and they're all
You know, so many of them are just great people and
They now teach me things.
Honestly, like Brian Cheske
Teaches me things. The the student has become the master.
He knows so much more about me and
running a business and I often like will go to him for advice.
And so I'm really lucky
To be surrounded by
So many smart people.
in the startup world because as a startup nerd
I mean I could
Talk about startups.
You know
and think about them all the time and it's so great to have
All these people around sort of lifting
Lifting me up.
Would you believe that uh serial
Experience uh
Led to a ninety two billion dollar business today. I just looked it up. How big
Gotten.
Honestly.
I wouldn't.
And it's
I wish I could say, Oh, I knew they'd be this big but the truth is
With
All of the super successful startups
Yeah, you can remember feeling very positively about them.
And certainly feeling like as they went along in the first few years, like they're doing really well.
They're really determined.
They're doing a great job, but you just
Never really think
They don't they themselves probably didn't realize that they'd ever be that big, let's face it.
That's just the way startups are.
Okay, here's the actual final question.
Is there a
Fun story of early days Y C
Whether it's with
Airbnb founders or Paul or anything that
comes to mind as just like wow, what a
What a different time that was, or what a surprising

ideas I've had lately is that I want to start thinking about writing.
Sort of.
O Y C biography.
Kind of book.
I don't know when the time is, but I the point is I have to remember things.
'Cause it's hard when it's been twenty years.
To go way back, you have to remember
specific things that happened. I mean
Well, I see, I just remember the early days being so magical and so
Pure
When we started
Like no one knew about us.
No one was bothering us. We just did what we were doing.
With no distractions. We were helping
Albeit a very small group of founders, you know, eight in that first summer.
Um
We were just doing what we love doing.
And growing organically and no one was scrutinizing us.
Or blaming us for things or
You know
Writing negative
news stories about us. I mean the the negative
Stories in the press.
Because I'm
A people person and I'm I'm very sensitive.
Like Paul's not as sensitive as me.
And so
He doesn't care if there's a negative story in the press that's not true.
Like I do. It it really like affected me.
And I hated when we got big enough that
You know, people would
lie about us and say bad things. So I wr I look back fondly when we first started
It was the most fun time of my life, the most productive time of my life.
Didn't have kids then.
And I could just
help the founders and like learn about all these exciting
things that happened in the start up world because it was new to me.
then the startup world was new when we started Y Combinator. So I had a lot of learning to do. And I met all these cool people.
And it was just very authentic. Like no one was doing it.
To be cool.
Okay, well let me let me ask maybe one other question. Was there a moment when you felt like Y C
Was working.
When it felt like, wow, maybe this is gonna
Make it.
There were sort of two moments that I remember
I felt like Y C was working.'Cause remember we started Y Combinator
As
One hundred percent like an experiment.
Could we fund
Um younger founders
Uh with small amounts of money.
That was it. Then that summer we created this batch investment idea and then that became the idea of funding them in batches.
And that was the first aha moment was after that first summer
When we
invited people to participate in the Summer Founders program, which is what it was called. And remember that
For summer had
Sam Altman.
Emmet Sheer and Justin Conn.
Alexis and Steve have read it.
You know
Those were they were in the first batch.
And the batch thing worked really well because they all became friends.
We could have dinner every week and bring in guest speakers and w and then
Introduce them to investors at Demo Day and
That
That whole batch investing thing was an aha moment and we said
Oh my gosh.
Let's
Keep doing this. This really works.
And
So we said
that was a moment where we knew we were on to something. And that's when we then did it in California in the winter.
But
The the second
Big moment.
was probably it was I remember it was like a year later and no
Pr no reporter would write about us.
Investors really didn't
Yeah.

But I remember when
Reddit got bought.
by Condane Ast in two thousand six.
It was
That's
And then at the same time I think it was like Charles River Ventures or one of these Boston
Maybe it wasn't even Boston, but it was a V C firm.
Did like the seed program?
Where they invested maybe a hundred K in startups.
And the press like
loved that. They like wrote all about this one hundred thousand dollar investment.
And they'd sort of
Mention why Combinator.
as doing small investments.
And then that coupled with the Reddit press.
sort of made us feel like, Oh my gosh, we are sort of legitimate.
in the eyes of outsiders became sort of aware of who we were.
And I sort of felt like
We've arrived. We've been in the newsp you know, we've been in the press.
Like people are finally paying attention.
That's amazing and it's funny that Red It just went public. It's kind of the other side of that that coin. I know.
Pretty impressive. I mean
Definitely didn't
Didn't necessarily think that was gonna be happening.
I know you have to run, but I can't help but ask around the s what you just talked about, where you decided to invest in batches. You wrote this really interesting
uh point that none of us had any experience angel investing.
And that's where the idea of funding startups and batches came from. We decided to fund a bunch of startups at once during the summer so that we could learn how to invest.
And I love that
Your inexperience in doing it.
created the structure.
Like that unique.
Weakness slash strength is like what led to the
way uh Y C operates. And I think that's really interesting.
Yeah. Yeah, we definitely didn't
wanted to learn more about how to be investors. So that's when
We decided to do this
you know, f summer founders program where we could
Invest in a whole bunch at once, and then the plan was to go to asynchronous investing like normal investors.
But we realized that this there was something magical about this batch thing.
So sometimes
I always say we love domain experts, but sometimes maybe ignorance
is sort of bliss and you just discover new things.
Jessica, this was everything I hoped it would be. We covered so much ground. I think people are gonna love it no matter what you think. Oh good.
Good, good, good.
Two final questions. Where can folks check out the social radar is and anything else you want people to know about? And how can listeners be useful to you?
Uh well, you check out the social radars on all the you know
Podcast platforms.
Apple, Spotify
Amazon, all of those.
And then there's a website, but
uh social radars dot com
And
They can be helpful by just
listening to it and spreading the world because I don't do
Any marketing for it.
Besides
Like posting on Twitter.
Just'cause I'm I'm a
You know, you know, it's expensive doing a a podcast and stuff, so I don't do any marketing.
So
If it resonates with you, if you find an episode interesting
Please spread the word.
And write a review.
And and rating.
I was just gonna add that. I'm glad you threw that in there.
Jessica, thank you so much for being here.
Thank you so much, Lenny. It was a lot of fun.
Same for me.
Bye everyone.
Bye.
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