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Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe

Transcribed podcasts: 277
Time transcribed: 11d 5h 6m 45s

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What's up, everyone? This is Cortland from IndieHackers.com, and you're listening to
the IndieHackers podcast. On this show, I talk to the founders of profitable internet
businesses, and I try to get a sense of what it's like to be in their shoes. How do they
get to where they are today? How do they make decisions, both at their companies and in
their personal lives? And what exactly makes your businesses tick? And the goal here, as
always, is so that the rest of us can learn from their example and go on to build our
own successful internet businesses.
Today, I'm talking to Aileen Lerner, the founder of a company called Interviewing.io.
Aileen, this episode has been a long time in the making. Glad to finally have you on
here.
Hey. I'm very excited to be here, big fans.
Right at the top of your website, you say that technical interviewing and looking for
a job as a software engineer are annoying, and that at interviewing.io, you make both
of these things less terrible. Tell us about how you do that.
I wrote that copy. I'm very pleased with it.
That was one of my questions I was going to ask. Who wrote this copy? It was a youth.
It was me. It was me, for better or for worse. I'll tell you a bit about some earlier copy
we had later, if you'd like, the one I was very proud of that we can't use anymore. So
what was the question?
What a great start to this interview.
This is amazing.
What do you do? What is Interviewing.io? Who uses it? Why do they use it?
So Interviewing.io is, well, depending on who I'm pitching, I position it very differently.
But given that this is mostly, I think our listeners are mostly software engineers, we're
a platform that provides people with really high-quality, free, and completely anonymous
mock interviews. Then we also make it easier for you to get a job if you want.
So I can go into a bit more detail on what that means. Basically, I used to be, maybe
I should introduce myself. What do you think?
Yeah, who are you?
Yeah, why not? I'll come back. So I'll tell the windy story of why I operate in this space,
even though hiring is gross. So I was a software engineer for a few years, about five. One
of the things that was always hardest for me was hiring people. It was at best kind
of a painful distraction. And at worst, it was just this kind of Kafkaesque nightmare.
So one of my biggest frustrations when I was an engineer was just that a lot of the best
people I was working with didn't look good on paper. There's a guy that, one of the best
engineers I ever worked with at the job where I was the longest, who I think did a semester
at some fifth-tier state school and then dropped out because he realized it was dumb and then
went to work. And when he applied, we almost turned him away because of that, even though
his high school friend, who was among the best engineers I've ever worked with as well,
really gave him a strong referral. So that really upset me. And stuff like that happened
all the time.
I think we all have friends that are amazing engineers that just don't look great on paper.
So I ended up, in part because of these frustrations and in part because I didn't want to write
code for the rest of my life, ended up transitioning to technical recruiting. So I started by just
doing recruiting stuff at the software company where I was working because all of us were
constantly getting interrupted to do interviews and then we had to go back to work.
And we were doing everything from our own scheduling to just looking at resumes. It
was not the best use of our time. But then I really got into it and I just saw how broken
recruiting was. So I ended up running recruiting at a couple of companies. One was trial pay
and one was Udacity. You've probably heard of Udacity, maybe not trial pay as much. Then
I started my own recruiting firm.
And what was really annoying was, again, I just kept running into this issue over and
over. When I was recruiting for a bunch of startups in the Bay Area, I would have candidates
that I knew were amazing because I had run them through super rigorous technical interviews
myself. Then I just put the alien learner stamp of approval on them. Not that that necessarily
meant that much, but in my world, I like to think it meant something.
And I would present them to companies. And companies, the recruiters, these companies
would just look at this candidate and be like, we don't want to talk to them. And I'm like,
but they're really good. I know they're really good. And they're like, yeah, we don't care.
We're hiring from these five schools and they have to have worked at one of these companies
as well. And that just really pissed me off.
So I started interviewing IO to stop that kind of thing from happening. So on our platform,
if you're a software engineer, when you sign up, you can just grab a time slot. And then
when you show up at go time, there's going to be a senior engineer from a Google or a
Facebook or a Dropbox or a Microsoft or any number of other companies that tend to have
pretty difficult technical interviews. That engineer is going to run you through a very
realistic, either algorithmic or systems design interview, and they're not going to know who
you are. So you can screw up all you want without any negative ramifications. And if
you do do well, then you can unlock our jobs portal. And then with one click, you can book
a job interview at a number of great companies. So we work with companies like Twitter and
Lyft and Uber, Dropbox and a number of others.
The nice thing is now instead of having to get your friend to refer you or having to
apply online, which is like screaming into a black hole, right? You never hear back.
Or having to hope that the recruiter that contacted you six months ago when you weren't
looking is still working there. They're probably not. You just press one button and then you
have a guaranteed technical interview at that company probably the next day. And it's still
anonymous. So the company doesn't know who you are until you do well.
That was a very long answer to a very short question. Did that make sense?
It made perfect sense. You said a couple of cool things in there that I want to talk about.
You said that you work in hiring even though hiring is gross. You said that recruiting
is broken. Let's say you could snap your fingers and change the industry, change the
entire industry of hiring software engineers. And you can do this once with each hand. So
you can change two things. What two things did you change?
I feel imbued with God-like powers.
You are.
Gosh.
Welcome to the index podcast, Aileen.
Some butterfly effect stuff here. I don't know. I'm just very, very paralyzed. Well,
look, the thing I find just immensely frustrating is just that good people don't have access
to opportunity. So I guess what I would do if I could snap my fingers is... Well, actually,
I'm going to answer this a bit facetiously first. I just wish everybody used interviewing
IO because the thing we've built there is the thing that I want to see in the world.
This idea of you're evaluated on what you can do and not how you look on paper. And
also this idea of... Just to back up a bit, the way hiring works, and this is why I said
it's gross, is it's just such an antiquated process. I think a lot of our hiring approaches
come from a time when there was a shortage of jobs and a surplus of candidates.
If you read a typical job description, they're garbage. They're the worst. And if you read
a typical job description, it's just this long list of bullet points saying stuff like,
you have attention to detail and you're not a murderer. And just all this dumb stuff that
has nothing to do with the job. I guess not being a murderer, maybe you want to filter
for... I guess it depends on the job. But generally, the way these things are written
is meant to exclude. And it's meant to be like, oh, we have all these people beating
down our door and make sure that you fit these criteria. That's not how hiring works anymore.
Especially in software engineering, there is a shortage of good people in a surplus
of jobs. But the processes we're running are not optimized at all to make candidates move
through the process fast or to add value or do anything. It's weird. There's this tension
between we need to hire all these engineers and then you apply to a company and then they
give you a two-week coding challenge to do that they don't pay you for. It doesn't make
any sense.
So I just want hiring practices to line up with market dynamics. So if there's a shortage
of candidates, you should roll out the red carpet for them and treat them well. And if
there's a shortage of candidates, you should be looking at talent pools that aren't just
Google and MIT alums.
That's actually the right answer when asked what everybody should be using to answer your
own company name. So yeah, this is a test.
Did I pass? I hope I passed.
Yeah, you got it right.
Thank God.
So you are hiring and recruiting expert. There are a lot of people listening who are themselves
software engineers or who are starting companies that hire software engineers. So I want to
come back to this topic and just mind you for information. But first, I want to talk
about why does this process of interviewing and hiring suck so much? I know a lot of people
who would not be founders today if it wasn't so scary or difficult to interview as a software
engineer.
I'm so terrified of having a job, my God. Oh, there's so much shit I will do to not
have a job.
Let's go through this list. What would you do to not have a job, Aileen?
Oh my God, I don't know.
Star company?
Yeah, I think I would definitely do that. And starting a company is miserable. I mean,
I guess it's, what's that line about war? That it's like long periods of boredom punctuated
by moments of sheer terror. I think that's entrepreneurship is kind of like that too.
Nevertheless, you are a founder. So why are you founder? What do you like about doing
this?
I feel like I'm lying on a psychoanalysis couch at the moment. I don't know. I think
that there's a certain personality that goes with being a founder. That's not always true.
Founders come in all shapes and sizes and temperaments. But for me, I've just always
had issues with authority, I think. So I've had issues with just having to do stuff that
didn't necessarily make sense to me. And at least when you have your own thing, you might
be telling other people to do all sorts of stupid shit. My staff will attest to this.
But at least it's your stupid shit. And you have some control over your destiny. So that's
one. Two is, I don't know if this has been your experience, Cortland, but there are some
things I'm pretty good at. There's a lot of stuff I'm bad at. But I don't know that there's
just one thing I want to do with my time.
Here when you're a founder, you get to solve all sorts of weird problems all the time.
And I think that's really interesting. And those problems are cross-functional. And they
really just stretch you to the limits of your ability. And some of them are really boring
and you wish you didn't have to solve them. But a lot of them are things that you've never
done before. And I think that's really cool.
It's definitely been my experience as well. You've been at this with interviewing I.O.
for four years now, right?
Mm-hmm. That's right.
You've got a dozen people that you're working with full-time on this. You've got many more
contractors. So you've created jobs. You get to tell them what to do and no one's telling
you what to do.
Well, I mean, people still tell me what to do. I'm grateful for it. A lot of my employees
know what to do better than I do. So I try to listen.
Yeah, great. That's even better. Your employees are so good. They're telling you what to do.
You've got a cool company that's actually helping fix an industry that you know a lot
about and that you're passionate about. You've grown your revenue to multiple millions of
dollars per year in just the last four years. So overall, you've come a long way. You've
accomplished a lot.
Thank you.
You've accomplished all this. Would you say that it's worth it? Are you happy?
I don't know if I'm happy, but I'm certainly happier than I've been before I had this job.
I think one of the nice things, and I think you and I talked about this in the past, right?
This idea of like when you're a founder, even if you're sort of tactically miserable, right?
You don't have time to be existentially miserable. So you're so busy and hopefully you're doing
something that you find meaning in, even if certainly nothing has meaning, right? Everything
is completely chaotic and meaningless and the universe gives zero fucks about you.
But in your little corner, you've kind of created the suspension of disbelief that what
you're doing matters. And as long as you have that lodestar of like, hey, I'm doing this
something that matters and you pretend that it does, then all of a sudden, even if your
life is terrible, even if one quarter, your revenue goes down or people leave your company,
all sorts of things happen that are very, very stressful when you run a business.
But you don't lay around at night thinking, you know, why am I here? And what am I doing?
And this is the first job where I felt that way, where I feel like I'm doing what I'm
supposed to be doing. And I don't care how miserable I am on a day to day basis, I will
trade that for being kind of existentially purposeless.
Okay, let's talk about this. Let's talk about some of these other jobs where you didn't
feel like you were doing what you were supposed to be doing. What were some of those jobs?
I've generally been fortunate enough to work in companies where I've liked the people that
I work with and some jobs I stayed at way longer than I would have otherwise because
I love the people. But every job I've had after the first, I don't know, sometimes the
learning curve was more steep than other times. But eventually, once you figure out what you're
doing, and you're not overwhelmed, it's like, why am I doing this? And it didn't matter
how great the company was, it didn't matter how good my coworkers were, ultimately, although
that did keep me pretty happy day to day, it always felt a little bit empty.
I used to cook for a living. I guess that job for a minute satisfied my existential
longings because it was so difficult, and I was so bad at it, at least for the first
few months, that I didn't have time to think about other things. And that job was really,
really cool.
And then eventually, I figured out that I'm never going to be Tony Bourdain. God, I don't
even know how to pronounce his name. That's embarrassing. But I realized I wouldn't be
him. And at that point, I quit. But for a little bit, that job was almost as fulfilling
as doing this, but never quite as.
I want the story of how you got there. I mean, how does someone who is now a software engineer
running a tech company, how did you even become a cook in the first place?
Well, so as you know, we're both MIT alums. And it's a great school, but it also kind
of bleeds you dry, or at least it bled me dry. I didn't really know what I wanted to
do. And I was just so burned out on academics that when I graduated, I didn't really have
a plan. And I really liked watching Food Network. Like let me if there's a time in my life to
do something absurd, right? It's when I'm 21 and 22, and not when I'm 30. And I thought
about going to culinary school. I think culinary school is like the the coding boot camp, right?
So you know, if you look at coding boot camps, websites, and you talk to the people that
are trying to get you to go there, they'll promise you the world, right? And they're
not cheap. Fortunately, these days, some of them are aligning their incentives better
with students, and then you don't have to pay until you actually get a job. But that's
not how it always was. And there's still plenty of them where you just have to pay quite a
bit of money up front. So I thought about going to culinary school, which as it turns
out, here's some something crazy. Back when I was at MIT, I think it was fully if you
pay a full if you pay retail, going to college is something like $17,000 a semester, I think
it's a lot more now dates me a little bit. But back then culinary school, you'd go for
three semesters, it was like an associate's degree, and it was 50 grand. So to go to some
crap culinary school, it costs the same as going to MIT. So that was just not an option
for me, especially I went and I talked to some chefs, and I realized that once you graduate
from culinary school, you're going to get the same job as people that didn't go to school
at all, except you're now $50,000 in debt and you're making $11 an hour.
What a deal.
So with the best, right? What's the deal for the schools? They're fucking killing it.
How do I get into the school business?
Yeah, right. Let's open a culinary coding bootcamp, just like really screw everybody
in every capacity, right? I chose not to do that and I found a restaurant that I just
looked on Craigslist and there are all these restaurants that were hiring cooks and I didn't
know how to do anything. I had taken one class in college called kitchen chemistry. Did you
ever take that one?
I didn't even know that was a class.
See? Yeah, it's like during, you get like two credits or I forget what a credit is.
You get some nominal portion of whatever credit you'd normally get for a regular class and
then you make pancakes and you hang out and it's really great.
So I took that class, but that was about it. I didn't know how to chop anything. So I found
finally, after applying to like a hundred restaurants in Craigslist, most of whom laughed
at me, I found one that was like, hello, you can come here and work for free. And I was
like, great. So I worked for free for three days. They taught me how to chop vegetables
and then they started paying me. And then from there, I tried to make the next job I
went to better than the previous one.
During your stint as a cook, were there any experiences you had or lessons you learned
that have helped you out subsequently during your life as a founder?
I think actually the most lasting thing that I learned was about hiring too. I'm not just
just making that up to bring it back. This is 100% true. Like I was fascinated by how
restaurants hire people.
So if you want to work at a restaurant, nobody gives a shit about your hopes and dreams.
Nobody really looks at your resume or your resume is kind of meaningless in that industry
as well. You just come in and you bring your knives. And in the morning, they show you
how to set up your station and you're prepping. So that means you're making sauces, you're
chopping vegetables.
I mean, in some restaurants, they also like put an onion in front of you and they're like,
chop this onion. And you're like, okay, then you chop the onion. You basically set up your
station and then during service, so come 5 o'clock, people start showing up for dinner.
They show you how to do the dishes that your station is responsible for. And then all night,
you're just putting out those dishes and then they're watching you and they're like, are
you doing a good job?
Then at the end of the night, if you do a good job, then they feed you and they make
you an offer. And if you don't do a good job, they send you home. Maybe they feed you if
they feel sorry for you. But it's very, very fair, or at least much more fair than anything
I'd ever seen in an office setting.
And I didn't quite realize how much of an impact that had on me until years later, but
I filed it away. And that's the kind of fairness I'd like to bring to our industry.
Yeah, that'd be like being a developer, just going in and working a real day on the job.
Exactly.
Of course, you wouldn't do that because it'd take you a whole day just to get your environment
set up.
Yeah, totally. I wish somebody would crack that. And I think it's harder because you
don't have a day to give. And when companies are interviewing you the standard way, it's
a lot faster.
So it's a complicated thing. But there has to be a proxy where you don't really have
to spend... I mean, like you said, a day is unrealistic because you have to just clone
your repo and mess with config files and do whatever the hell you have to do. So you don't
have to spend a few weeks working, but there has to be a better way than what we do now
that serves the same purpose.
So fast forward a little bit. You eventually quit your job as a cook. How did you transition
into tech?
So I quit my job as a cook after about three years in the industry. And then I just had
no idea what I wanted to do. I was sort of going through this quarter life crisis. I
think I was 25 at the time, so it was apt. And I remember... Well, one, I was out of
money. I was just completely out of money. I had saved a lot of money because I started
a tutoring business when I was in college. And at the time, my friend and I were raking
it in. We're making like $50 an hour. We're like, holy shit. We're rich. We're so rich.
And then I burned through most of my tutoring money and went into debt and I just had nothing.
So I saw this advertisement for this MIT program called MEAT. They changed what it stands for,
but back then it stood for, I think, Middle East Education Through Technology. So the
idea was they fly you to Jerusalem. And then you teach programming to a mix of Israeli
and Palestinian high school students.
I thought that was amazing, right? Because the whole thesis was, hey, instead of sitting
around and talking about politics and the conflict, what if we just make... This is very
kind of hippy-dippy. What if we just make people build stuff together with code? Then they'll
find a common language and then they'll build some foundation for mutual respect. And I
thought that was really cool. I wanted to be part of it. And I also had no money and
there was a stipend and I had a place to live for the summer if I went to Jerusalem. So
it was just a win-win on all fronts. I don't think I've ever admitted that to the program.
So hey, guys, if you're listening, sorry. I did it for good reasons also. But that kind
of got me back into programming because teaching something is the best way to understand it
better yourself and fall in love with it, I think. So after that summer, which went
super, super well and where I made some very lasting friends, probably among the best friendships
of my life, I came back and I was like, you know what? I can do computers. Computers aren't
as bad as I remember. It'll be fun. And then I did computers for five years.
I'd worked in tech, I guess, during college. I had a number of internships. So it wasn't
my first foray into writing code and production, but it was close to it. And I remember preparing
for job interviews back then after spending three years drinking and having plates thrown
at me. It was interesting to get back out there and interview. I remember I had to reverse
a linked list and I'd forgotten what a linked list was. So that was cool. But eventually
I figured it out. And then I spent most of my time actually at one company, which I never
would have thought I'd end up there, but it ended up being an amazing place to work.
And so many of the people that have worked that have gone on to be very, very successful.
They're still around. It's called Click Time. And they did SAS time and expense tracking.
So I spent five years making time sheets and it was not as horrible as you would think.
Okay, so you've got this amazing job making time sheets. The people around you are great.
Why ever leave? Why ever go on to do your own thing?
Well, I fell into recruiting there, right? So that was the place where I said, you know,
we were all kind of jumping in and ramping up and ramping down and constantly getting
interrupted. So I was like, Hey, this is this is cool. I think there's a real problem here.
I think I, what I didn't know at the time was that technical recruiters were not technical
usually. Like that, that blew my mind. I was like, how can people that aren't engineers
be involved in filtering and vetting engineers? Just crazy. But that's, that's how it works.
And I thought, you know what, I'm an engineer and I think that there's an opportunity here
that and after five years of doing computers, as I like to put it, I, I don't think I wanted
to do it for the rest of my life. I like writing code to solve problems, but it doesn't like
when I was in school, there are all these people that just lived and died for this stuff.
Like this is all they lived and breathed. And, and you know, it was just so thrilling
to them to code. And I knew that I would never, I want, if I'm going to do something, I want
to be the best editor, at least among the best. And I knew that if I didn't have this
level of passion for the craft, I would never be the best. That and I, I'm not saying that
I was a great programmer despite that, right? Like I was decent, but if you're decent and
you don't love it, like your odds of excelling are very, very low.
Yeah. Because you're competing with people who are really good.
They want to do it.
Who love it. Yeah.
Do you like programming?
I love programming, but it's also a means to an end.
People like you.
It's a means to an end for me. I wouldn't code if it couldn't create cool things. I
wouldn't do it just to sit on my computer coding all day. So I think I'll also probably
never be the best software engineer because I'm not only doing it for its own sake.
Yeah. Yeah. Like the truth and beauty and beauty and truth thing.
Okay. So at this point, you leave your job as a software engineer, you get into recruiting.
You're a person who wants to avoid existential angst. You want to keep yourself busy. You
want to be the best at whatever it is that you're doing. How do these two things inform
how you approach your job as a recruiter and the next decisions that you make?
Yeah. Well, so I didn't quite quit my day job yet, so to speak. So what I tried doing
was just moonlighting as a recruiter. Because I saw with third party, there's so many shitty
third party recruiters out there. And we were trying to fill roles and we were using agencies.
And I'm like, my God. And then I found out how much of those people were getting paid.
And I'm like, shit. Just like with the other. This is a case where my hopes and dreams and
financial incentives line up really well. I'm like, this is a problem. I hate how unfair
hiring is. And my God, there's so much money in the space.
How much were they getting paid?
So back then, it hasn't changed very much. So I think right now, industry standard for
a contingency recruiter. Contingency means you get paid when you make a hire. So industry
standard is somewhere between 15 to 20% of first year's base salary.
So if a software engineer makes $150,000 a year, what's a fifth of that? Well, $30,000.
So you get $30,000 every time you make a placement. So it's a lot of money for not very much work.
It is more work than people think, though. There are a lot of people that think recruiting
is very, very easy. And I was naively one of them. It's not easy. There's all this nuanced
stuff that you realize once you get in there. But it's not a backbreaking job, I'll put
it that way.
So I started moonlighting as a recruiter. I had a few friends that had startups. And
I was like, hey, guys, can I just try to make some hires for you? And we'll see what happens.
And I could. And it worked well. And one of those companies was TrialPay. And they took
a chance on me and gave me the title head of technical recruiting, even though I had
never worked as a recruiter before. So I'm forever grateful to them for doing that, because
that's what got me started in this space. And I was very fortunate to be able to land
that position.
One of the weird things about that job, too, was that I was kind of half recruiter and
half technical interviewer. So because I could do technical interviews, and I had been an
engineer for years and years, they're like, hey, what if you're the one that just interviews
our candidates and it'll sort of take the heat off the edge team? I was thrilled to
do it. I was like, I'm going to learn something no matter what. This is going to be cool.
And I ended up doing something like 500 or 600 technical interviews in the year that
I was there. Yeah, there was somewhere I was doing like six a day. And then I would just
go home and sit in the dark and just like, God, what a day. But that also sort of helped
me get here because I started realizing there are a lot of patterns and repetition to how
interviews are done. And there's a lot of stuff that's bad. And that job also, whenever
I'm doing something that makes me miserable, I don't know if you do this, but whenever
I'm doing something weird or something that is arduous, I think I'm going to write about
this one day. And then it makes it better. And in this case, I was doing these interviews
in part because I thought maybe I could write something interesting about it. And what I
ended up doing, because I was the person that decided who got interviewed and then the person
wasting my own time, when I interviewed the wrong people that I felt okay, like casting
a very wide net. So I talked to a lot of people and ended up writing a piece about what attributes
of a resume might predict whether somebody gets an offer.
So I interviewed all these people, looked to see who was successful. And then I looked
to see who was already working a trial pay. And I looked at their resumes and tried to
see is it the number of years of experience? Is it whether they went to a top school? Is
it whether they know a specific programming language or framework? Do they have their
own website? Do they have a GitHub? Do they have lots of projects? Did they work at a
top company? Looking at all of these traits. And this is the first thing that I ever really
wrote on the internet that took off that also shaped what I ended up doing later. But in
that analysis, when I wrote about it, I found out that the thing that mattered most much
more than where people worked. And incidentally, where people went to school didn't matter
at all.
But the thing that mattered most by far in a way was how many typos and grammatical errors
people had on their resumes. Yeah, it was insane. I mean, I spent months manually counting.
You can't have a computer count typos because all resumes are full of acronyms and all sorts
of weird proprietary technical terms. So like, yeah, really, there are three things that
mattered. Number one was number of typos and grammatical errors. And of course, the fewer
the better. I almost said the less the better. And then I corrected myself. The second thing
was how clearly they explained what they did at each position. So a bad explanation would
be, I took part in the software development lifecycle. Whereas a good explanation would
be, my team was responsible for upgrading this thing or building this feature. And this
feature had this much traction. And here's why it mattered. Basically, what you'd expect.
And then the third thing that mattered was whether somebody had worked at a quote unquote
top company. That mattered least. Everything else. Years of experience, advanced degree,
large GPA, all these other things didn't matter at all.
That's interesting because it implies the top companies aren't doing that good of a
job filtering people. Because if they were, then working at a top company would be a pretty
good signal for whether or not somebody's good.
Yeah, I think the idea was like, at least if somebody else was willing to marry you,
maybe you're not the worst. Which is not necessarily the best way to make decisions.
No, it's not.
So you're a software engineer. At this point, you're working as a recruiter, basically. Did
you think about how you can apply your skills as a software engineer to perhaps scale this
business and turn it into something bigger?
Well, so I did. Well, part of the reason I wrote that blog post I was just talking about
is I was trying to come up with the ultimate logistic regression of truth. Where you could
have a... It started as a hackathon project. I put in someone's resume and it would just
give me a score. The score was really either yes or no because that's ultimately all you
care about.
So I started that way. I realized very, very quickly that that was not going to work. The
resume fundamentally just does not have enough signal to extract any kind of meaningful decision.
That's why I'm very skeptical, incidentally, of any AI hiring startups because I don't
know what they're using to get signal. But there's no magic. There's not that much info
available from people's public profiles to decide can they code or not, right?
So when I realized that didn't work, I realized that there has to be some other way to get
data about candidates that would be more meaningful. And I kind of got there organically. So after
I wrote this thing about typos and grammatical errors, I published it and people liked it.
And then by this time, I had started my own recruiting firm where rather than just working
at trial payer Udacity, I was doing my own thing and hiring for about 40 or 50 companies
because I had started writing all this stuff on the internet about how hiring was totally
broken.
A lot of really good candidates started approaching me saying, Hey, you know, I'm non-traditional
on paper. Can you help me get my foot in the door at a top company? And I didn't know what
to do with them because, you know, my normal approach is useless here. I couldn't look
at their resume and didn't tell me very much. And their resumes in particular, I didn't
know how to parse because I'd never heard of their employers or their schools if there
was even a school. So I just started interviewing them. And then I realized, you know what,
if there's a way I can make a platform where we get people's interview performance, and
then on top of that, if we can trick companies, I told you earlier just how frustrated I was
that companies wouldn't talk to my candidates, even though I said they were good.
So like, if there's a way to like get candidates to hang out on this platform, do interviews,
the best people and then force companies to talk to those best people despite themselves,
then there's going to be a business. And that's how interviewing IO came about.
Was this like a flash of insight? Like one night in the shower, does boom, it hits you
or?
It might've been on the toilet, I think, which is where I do a lot of my best thinking. I'm
not sure, but it's very possible. It was either the shower or the...
This is not the important half of the question.
Sorry. No, but I'm like, I've got the answer. Cortland, listen, it was on the toilet.
All right. A flash of insight on the toilet.
Did you at some point turn this into a plan for your business or a strategy or a roadmap
or something?
To this day, I'll be honest, I have no idea what a business plan is or how to write one.
People keep... And people keep talking. I'm like, what is that? I don't know. This seems
like a waste of time.
The way I tried to validate it was... Well, I mean, I tried to do something out of necessity.
So I was running this recruiting firm, and then I had this idea. And then I thought,
well, I'm making a lot of money being a recruiter. Do I really want to just shut this down and
do this random thing? I don't even know if... I think people want interview practice, right?
That's something I'd kind of figured out from doing a ton of technical interviews back when
I was at trial pay, but I wasn't sure.
So I put up this really, really shitty marketing site on Hacker News, and it said, free anonymous...
Maybe it's a practice. Actually, it said something pretty similar to what our marketing site
says now. So it said, practice interviewing with engineers from top companies anonymously,
something like that.
And it was number one on Hacker News for, I think, two days, and something like 7,000
people signed up the first day.
Whoa.
So I was like, okay, time to quit my job. Time to shut down my little recruiting firm
and do this instead. My favorite piece of copy from that site, incidentally. So I was
like, practice interviewing. I promised you earlier I would tell you my favorite piece
of copy, for better or for worse. I may regret this. But I was practice interviewing with
engineers from top companies, blah, blah, blah. And then underneath it said, it's like
Chatroulette, but without the dicks.
And we had this marketing site probably for the first year that we were in business, maybe
more. Still said it. We were signing all these enterprise customers that were hiring through
us. And at some point, one of our favorite customers, my main contact point from there
called me up and he's like, Aline, I like you. We like working with interviewing. I
always think this is funny, but not all of us think this is funny. Some people on our
team think that the dicks thing is a little offensive. Can you please take that down?
And we did. We're a bunch of sellouts.
You are. You had a personality. You had a soul.
Yeah, no more.
This is what happens when you start a business.
Kids don't start businesses. Eventually, you have to take down the dicks.
It's true. Okay. Well, this leads perfectly into my next question. As a founder, you're
the person who really wears all the hats. You're not just sitting on the toilet coming
up with ideas, but you're also the person who's writing the marketing copy as you did
so artfully, Aline. You're also building the product. In most cases, you're hiring
the people to build the product. You're doing sales. You're doing everything really. And
I think as an employee, sometimes it can be hard to make that transition because you're
like, oh my God, I have to do everything. The responsibilities in my job are usually
pretty circumscribed. How am I going to wear all the hats? How did you deal with making
this transition, Aline? Because you were a software engineer for five years. How was
it for you to transition into basically being responsible for everything?
Yeah. I think one of the things that's... If I think about me before I started a company
or I think about people I know that are not founders, one of the biggest attitude shifts
that I've had to make and that maybe people that have a normal job don't have is that
there's no playbook and that there's also no wrong answer. I think people often get
very paralyzed before they do something because they don't know exactly the right way to do
it. I think the worst thing you can do is just... Especially if you're starting a company
is to just sit there and agonize over what you should do. It doesn't matter if you pick
the wrong thing. You just have to do something. And then no matter what, just accept that
everything you're going to do is probably going to be wrong. But as long as you're right,
sometimes that's probably good enough. And as long as you can figure out what you did
wrong and iterate on it. And this is not rocket science. This is like every blog about being
a founder will probably say the same thing, but I will cast my vote. This is absolutely
true. So even if you're trying to hire for your startup, let's say you started a company
and you need somebody to come work for you. It's very tempting to spend hours being like,
oh my God, who do I reach out to? Are they even going to respond to me? How do I source
talent for my new startup? And the fact is the worst thing you can do is just sit there
and not source talent. No matter what, the first few batches of emails that you send
to people are going to be crap. You don't know how to talk about your business. The
things that you think are interesting about your business may not be the things that other
people think are interesting. You're probably not good at talking about what you do concisely
because in your head, there are like 50 moving parts and each of them is endlessly fascinating.
But the reality is most people don't give a shit. So how do you distill your messaging?
And that just comes with failure and with repetition. I think that's the big difference.
Or if you're a job seeker, I'll go with your analogy, right? Especially if you don't look
great on paper. The best thing you can do... I mean, people just get in this rut where
they just start robotically sending resumes to companies and then getting annoyed when
they don't hear back. The fact is no one's reading those in the first place. So you shouldn't
feel bad and you shouldn't be annoyed. But the best thing you can do is probably reach
out to people that work at those companies. And that's really hard because you're making
yourself vulnerable and you're reaching out to a person that you have known nothing about
and you don't know what to say. But that feeling, if you can get over it and actually just write...
Let's say somebody at a company you want to work wrote a really cool blog post and it's
about something you're interested in. Maybe it's a project that you'd like to work on
if you worked at that company. If you can get over that sort of terror and write to
them and say, hey, I saw that you did this thing and it's really cool and I've been thinking
about something along the same lines and I really wanted to know how you did this. That's
good enough. And then once you do a few of those, that breaks the seal. And if you can
take that approach to every unknown that you encounter in the future, you'll be okay. So
I think just finding the activation energy, getting over that little hump and doing that
is the big difference and some people never get over it. And the people that do, I think,
especially if they have the temperament to be a founder, are probably going to be much
happier.
I love that point. There really is no well laid out path as a founder. There's nobody
patting you on the back saying, good job, Elaine. You're doing the right thing. Keep
going in this direction.
Well, my mom still... And dad, they do that sometimes.
Yeah, my mom does.
Yeah, right.
She thinks every episode of the podcast is the best episode.
Yeah, my parents too. Well, my mom texted me recently and she's like, your podcasts
are great. You sound so intelligent, but please, please, can you stop saying fuck?
Sorry, mom.
Sorry, mom. I'm sorry.
Okay. So as an employee, you've got a track laid out in front of you. You've got a boss
telling you what to do, what not to do. You've got promotions. It's all very comfortable.
It's all very guided. As a founder, you've got none of that, but you still have to make
decisions and actually take action. I want to talk about the actions that you took at
the beginning of interviewing IO. What was the very first thing you did after you decided
that this was the problem that you wanted to solve?
I think I tried to find a co-founder that... Because I felt really overwhelmed actually.
I kind of felt like I was holding an atom bomb in my hands and I didn't know what to
do with it. So I put up this crap marketing site with the dicks on it or the ref, whatever
it was. And people just signed up and I was like, the universe has handed me a gift. And
in the hands of a more capable person, this gift would be taken to fruition and realized.
And instead, this gift has been handed to me.
That's a lot of pressure.
And yeah, what do I do with this? And I was like, you know what? I don't think I have
the wherewithal to do this alone. I think I need help. And I certainly don't want to
build... This is going to be a complicated product. Our product hasn't really changed
from inception until today. We've made some changes. Certainly, the UI has gotten better.
We've built more features for employers. But at the heart of it, we had to build something
where people could talk to each other anonymously and write code and submit feedback. And then
we wanted those people to get ranked and we wanted scheduling to work.
It's not rocket science, but it's a lot for one person who hates coding to build. So fortunately,
we were able to use CoderPad. I remember you had Vincent on the show, one of my favorite
episodes.
So I think maybe even I went to him and I'm like, what do I do? We had met because he
read my blog. I think it was the post about how resumes are stupid and typos matter.
So fortunately, we were able to use CoderPad within our product and license it. But even
outside of that, there are a lot of moving parts. So I went around trying to find a co-founder
and my friend Art, he wasn't really willing to leave his job full time, but he was willing
to jump in and help and build something to get the product off the ground.
On top of that, I remember as a proof of concept to do the first few... We wanted to see if
anonymous interviewing could even work before we built too, too much. We generally tried
to build as little as possible and validate. It's this lean startup idea. At the time,
I didn't know what lean startup was. I just thought it would... Because we were so strapped
for resources that we should make sure this thing can work before we spend weeks trying
to build it.
So I remember it was me, Vincent, Parker, Parker Finney, who runs Interview Cake. You
should have him on the show. He's fantastic. Who else? Art was there too. We just emailed
some of the people that had signed up through that marketing site that was on Hacker News
and said, hey, we're going to book you some anonymous practice interviews.
And then we used Uber Conference and CoderPad and just stapled together some disparate things
to try to make it look like it would be... It wasn't anonymous interview. It was just
basically combining some tools together and making a flow that wasn't the worst.
We just interviewed those people to see if they liked it and to see if it would work.
And then it seemed like it would. So at that point, Art and I started building some stuff.
I'm a huge proponent of starting small. I think almost everybody should get started
that way. And you really started well before writing any code for interviewing I.O. You
were interviewing hundreds of software engineers as a recruiter. What was it like interviewing
somebody to be your co-founder?
Very different. I've never asked any... So Art ended up, like I said, he didn't join
full time. Eventually I got my friend Andy to join and he's great. But none of those
people I put through any kind of technical interview. I mean, in part because I had worked
with them previously on stuff.
So I think for me, the biggest questions were, one, do this person and I get along? Do we
make each other better? Is it fun to be around them? Can I see myself being walked in a room
with them for 12, 16 hours a day without biting each other's heads off?
The second thing was, and this is really important for all early startup employees, not just
co-founders, but can this person ruthlessly decide what matters and not get lost going
down technical rabbit holes? So can they build whatever? Can they just hack some shit together
and then fix it later rather than having to build the thing perfectly?
And also, do they know when it's important to stop hacking shit together and actually
build something more robust? Like that, especially for a technical co-founder, that's so much
what you do all day is make those decisions.
And then lastly, I knew for me, I'm not a very linear thinker. I go all over the place.
I think this is something that frustrates the hell out of my employees. But I wanted somebody
that was more of an analytical linear thinker and could sort of round out some of my flaws
and imperfections and fill in those gaps, and hopefully I could do the same for them.
That ended up being the case and was very lucky.
That's such a good point about wanting to hire early employees who know how much to
code, know when to hack something together, know when to stop. It's basically knowing
what the bigger picture is and not being so absorbed in the money details of your job
that you just want to be the best software engineer possible and you create amazing software
that the company doesn't really need.
Yeah, yeah. It doesn't make you write the most beautiful stuff and you're out of business
a few months later and didn't even get to see the light of day, right?
It's super tricky for people who come from a software engineering background where it's
all about having the right unit tests and making the best decisions and writing the
best code because that's all you have to worry about. To being a founder, when you've got
15 other things to worry about and the code's not the only thing that matters, so you have
to be able to make these trade-offs. What kind of questions can you ask somebody to
determine whether or not they're that kind of person?
Honestly, gosh. I mean, what I did with Art and then later with Andy was to just try working
together. I mean, again, I knew both of these guys pretty well. I knew I got along with
them. I knew that we made each other laugh. That's also really important, right? It's
like dating, right? Or marriage, you and everyone says this, but it's true. You have to just
enjoy being around each other and you have to be able to diffuse tension with laughter
because there's a lot of tension. But for us, we just got in a room and we're like,
all right, let's just build some stuff. Let's say we want to build this part of the product.
Let's just start drawing some stuff on a whiteboard and being like, what would this look like?
Are we aligned? Do we care about the same things? It's really hard to ask that, I think,
without just working on it. I think maybe if I were a better interviewer, which is ironic
because I run a company called Interviewing IO, but if I were a better interviewer, maybe
I could suss out some of these things through a series of very intensive top grading behavioral
interviews. For me, the best thing to do is just get in a room, be like, let's build this
part of the product together or let's design it together. Then it comes out very, very
quickly if you're not aligned on things. You don't always have to be, but then is it constructive
when you disagree? Can you communicate well? Can you limit the communication overhead?
How many words do you need to explain things to each other?
It's basically a relationship. It's like a romantic relationship without the romance.
Yes, exactly right. Or maybe you're both in love with a product rather than with each
other.
There you go. You both have your baby.
Yeah, it's like a weird three-way.
It's a love triangle.
Or maybe with your users. Maybe you should be in love with your users and the product.
It's too complicated now.
Just get out of hand, Aileen. It's like a love square now.
Yeah, we don't need that.
I think with interviewing I.O., it's obvious to me why software engineers love this. If
you had told me 10 years ago, hey, you can do free anonymous interviews online. Is it
free for engineers?
Yeah, of course. Of course. Of course it has to be.
Yeah, you can do free anonymous interviews. I would have signed up in a Jiffy because it's
like I get to save face. I get to practice my interviewing skills, get better. I might
even get a job out of it. The other side is probably much harder because you're dealing
with probably a lot of engineers who aren't that confident to go through the normal channels
who aren't already getting interviews.
As a company, maybe you don't really want to do business with interviewing I.O. because
this is a weird new thing. How did you get your first few customers to sign up from the
business hiring side of things?
Yeah, thank you for asking. The first few were harder than the last few. Our pitch to
companies is basically, hey, do you want to talk to some randos off the internet without
knowing who they are and put end time into it? You can imagine how that pitch can raise
some eyebrows. Of course, that's not literally what we say, but that's what people internalize.
We explain how it works. We say, look, resumes are stupid. Increasingly, in the climate that
we're in, fortunately, more and more companies are bought into this idea that a resume is
not the source of truth. That's been to our advantage and I've written a lot about resumes.
That's also helped things move along.
Honestly, for the first few customers that we landed, we had to let them try it out. Now,
the proof really was in the pudding there because they would talk to a few of our candidates
and then they'd be like, holy shit, this is so much better than the people we're getting
through our other channels and certainly better than the people that maybe even we're sourcing
ourselves because when you're sourcing, you're looking at the same signals everybody else
is. There's no opportunity to arbitrage anything.
Our employers would basically talk to a few candidates. We'd do free pilots where maybe
they would talk to four to six. Then after that, they'd see that most of those candidates
are ones they wanted to engage with. In a typical good hiring process, maybe 20% to
25% of candidates make it from the technical screen to the onsite. That's on top of spending
10 hours a candidate to source them and then having to do recruiter calls before you know
if the candidate is good. You're really investing a lot of time and then only about a fifth
or a quarter of people actually make it through to the next step.
In our case, it's around 70% and you don't have to spend any time sourcing. We save something
like 200 recruiting hours per hire and something like 15 to 20 hours. It's non-trivial. Once
people got their heads around that, they were generally very committed.
The other thing is, especially if you're thinking about starting a business where you want people
to try your product, think about how your pricing can reflect that. Fortunately, in
our case, at the beginning, we were charging these per hire fees and companies were already
used to this idea of paying a recruiter only if they made a hire. It was de-risked and
the pricing model was something that was already familiar to them. Does that make sense?
Yeah, that makes perfect sense. What's fascinating to me is that usually when you see an industry
is crowded as the one that you're in, recruiting and hiring and job placement, you see prices
get driven down. You see a lot of people coming in and saying things like, hey, you're charging
20% of the first year salary, I'll charge 15% to place an engineer. Hey, I'll do it
for a flat fee, $5,000 a head. Why hasn't that happened here? Why are you able to charge
as much as you do?
It's moving in that direction. It's gotten a little more commoditized. These days, most
of our revenue is coming not from these per hire fees, but from large flat fee deals.
We'll approach a company. They'll try us out. They'll talk to a few candidates, see that
those candidates are good. Then they'll generally pay us for a year of candidates upfront, which
ends up being about 50% cheaper than paying us per hire a la carte. Exactly what you describe
is what's happening.
But the other thing that I've seen that aside is that I think the reason it isn't as extreme
as you described is that companies are hurting so badly for engineers that price generally
is just not a friction point when you're selling. If you can promise people that you can get
really good butts and seeds quickly, they're willing to pay a premium for it.
You said something earlier that really resonated with me. That's that with Interview.io, it
felt like you've been handed a gift. You knew that in the hands of a very capable person,
the gift would be taken to fruition, but it's in your hands. You've got to be that capable
person and you've got to be the one who makes this company work. I think that's something
that a lot of founders can identify with. I identify with it. What are some of the best
decisions you've made since starting that have helped you get to where you are today,
where you're making millions in revenue, where you've got thousands of engineers who are
hoping to find jobs, and where you actually do feel like you're the right person for this?
I think most of my good decisions have been the people I've hired.
None of this would be possible if it were still just me. It's been unreal. Every time I look at,
I'm sitting in an office that has a glass window. I'm looking out onto the office right now and I'm
just looking at the people that work here. I'm like, why the hell are they here? They could be
anywhere. All of them could be anywhere and they could be making more money. It's crazy to me.
I'm just so grateful that people that are really good are willing to put their time into this.
I guess the thing I'm most proud of and I think one thing that I did do well is create a business
model where doing good is the thing that gets you paid. I think that's rare. In our case,
we're trying to build this efficient marketplace. The more efficient it is,
that means, not hopefully, definitely, the more meritocratic it is. In hiring,
efficiency is defined by are you hiring the right people for the right jobs?
So the more you can place the best people and the right opportunities,
the more efficient you are. Then, by extension, the more money you're making.
So that's crazy. You don't have to do mental gymnastics to be like,
oh, we're doing this thing. Then, through some kind of Rube Goldberg machine,
eventually, some good will happen in the world. It's like, no, this is a very,
very direct A to B sort of journey. I'm so happy that that is true.
I'm happy that the people that work here see it.
I don't have a ton of experience hiring people. A lot of people listening in right now are fledgling
founders or aspiring founders who are very soon going to have to start making hiring decisions.
We're probably going to do a lot of things wrong. What are some things we can do to get it right
the way that you have? People think that just because I know stuff about hiring that it's easy
for me, I've made some bad hiring decisions. I've let people go. People have left, right?
These things happen. It sucks. They do. But I think one piece of advice that I would give,
especially to new founders, is to remember that if you're trying to hire software engineers
in the market that we're operating in, hiring is not a vetting process as much as a selling
process. People don't have to work for you. From the moment you engage with somebody,
maybe you're sourcing them. You're writing to them saying, hey, come work for me.
Maybe you're interviewing them. Make sure that every time you interact,
you're adding value for them and you're giving them a reason why your company is awesome.
When you interview people, if you're fortunate enough to even get people to talk to you,
think about what kinds of questions you can ask them that don't just vet their ability to write
code but also showcase why the problems you're solving are interesting and unique.
Try to ask them cool, real-world stuff. Take them to lunch. Spend a lot of time with them.
Care about what they care about and weave a narrative where
the disparate path they've had up until this point culminates perfectly in working for you.
If you can't tell that narrative, maybe they're not the right person.
Also, don't be afraid of saying no to a hire if it doesn't feel right.
Sometimes there's a lot of pressure. You're like,
shit, I need somebody working right away. I'm drowning.
If it doesn't feel right, it's probably not.
Okay, so let's get back to talking about how you grew Interview Young I.O.
from something small into what it is today. Specifically, I want to talk about
the sales side of things. You calling up companies and convincing them to take a chance on you
to trust their hiring process to you, basically. I know in the early days,
you were doing a lot of demos, a lot of trial periods and just sort of hoping that people
would choose to use you after they saw that it worked. I imagine things have changed a lot since
then. So what are the biggest milestones and how your sales process has evolved?
We still, you know, it depends on the size of the company. If we're piloting with some like
huge brand, I mean, we're going to bend over backwards. We'll do whatever.
Okay, try as many candidates as you want. I'm exaggerating a little bit because eventually
we do want to get paid. But I don't know, it hasn't changed that much. Certainly,
I remember the first time I made a deck to sell. Like most of the selling, when I was the only one
doing selling, most of the selling I was doing was just like trying to have coffee with people and
just doing a demo. Well, of course, listening to their needs first and then showing them the
parts of the product that I thought spoke to their needs. But then eventually you get to the point
where you have collateral and different decks and different decks for different audiences.
And your sales process matures. Eventually, one of the milestones for us actually was
hiring a customer success person where we have enough enterprise brands that work with us now
that are used to a certain white glove, high touch kind of experience. And one of the guys
that works for me whose job it wasn't even to do sales, he was mostly doing marketing and product.
He and I were just running around playing whack-a-mole trying to pretend that we had
a customer success department. We were just running ourselves ragged and it wasn't good
for anybody. So making that hire was great because we put on our big boy pants at that
point. And I was like, okay, we have a person who's dedicated to making sure that customers
are getting value out of the product. Other things that changed. Early on, I keep talking
about how there's practice and then there are real interviews. Early on, we didn't have that.
Everything was just one big pool. So some people were there as practice interviewers. Some people
were there as candidates. And then we also told companies, you can just hang out in this pool and
you'll be matched with people and hopefully they'll want to work for you and you can just sell them.
So every interview was kind of practice until it wasn't. It was kind of this enders game
situation where it's like, oh, well, shit, I just ruined enders game for everybody. I'm sorry.
I'll cut this out. That's what I'll do.
Don't cut it out. It's funny. I want to ruin it.
I'm going to watch.
I know you're not sorry.
No, I'm not sorry at all. I hope this whole exchange stays in.
No, so it was just like this one big pool. And one thing we learned from talking to our bigger
customers and from listening to some of their interviews on our platform after the fact was
that they did not want to have to sell that hard because they were leaning on their brand. If you
have some big brand, you should be able to leverage that. So then we changed up our product.
So we had a practice pool. And then for our bigger customers,
candidates could sign up. And that was sort of a big turning point for us.
Another big turning point was getting into subscription pricing. So stopping just doing
per hire fees and making it so companies just paid us some flat fee for some number of candidates.
And that increased our revenue like 6x over the span of like a quarter or two.
Oh, that's nuts.
So there's a lot of advice floating out there for founders. We've talked about it a little bit
this episode. We've talked about starting small and iterating. There's also do things that don't
scale, talk to your customers, etc. Is there any advice that's common for founders out there that
you don't think you follow, that you just kind of skipped over and things were still pretty much fine?
There are a few things. So I don't know if this is controversial or not. But I don't agree that you
should be doing a lot of management early on in your growth. If you find yourself doing a lot of
people management, when you're like five people, six people, seven people, you're probably doing
something wrong or you hired the wrong people. When you're hiring this early, you should find
people that can sort of figure out what to do. And it's your job to communicate constraints
and goals to them. And then you kind of just want to set them loose on those constraints and goals.
Doesn't mean that you don't check in with them. It doesn't mean that you aren't helpful.
But ultimately, if you're looking over their shoulder all the time, either you're doing it
wrong or they're doing it wrong, or you're both doing it wrong. Another thing is people talk a
lot about having a ton of different perspectives. If you have people that work for you that
fundamentally aren't aligned with your mission and don't fit into the culture, it's bad, especially
early on. And this may be a bit controversial because you do want to kind of be encouraging
of discussion and you want people to suggest things. But fundamentally, everybody has to be
marching in the same direction. And if they're not, it's going to kill you. It's exhausting.
We had some friction at interviewing IO, for instance, where externally people often think
that we are first and foremost a platform that's dedicated to diversity and inclusion.
And we certainly believe in both of those things. But that is first and foremost, not what we do.
We believe in talent being evenly distributed. We believe in surfacing it. And we believe in
giving great people opportunity. But we don't specialize specifically in creating opportunities
for women or people of color. We're just like, we're just going to try to make hiring less bad
for everybody. And we hope that that ends up creating a more inclusive environment.
And that anonymity is something that's useful for people that feel marginalized.
But we're not a DNI platform. There are cases where people at the company wanted us to go in
that direction. And that's not something that I wanted to do. So fundamentally, it's important
that everybody has their eye on the same North Star.
Okay, we've talked about some of the things that have gone right with your business,
some of the decisions that you're proud of. What are some of the things that have gone
wrong? Whereas you could go back in time, you would change them. And also in the present,
what obstacles lie between where interviewing IO is today, and where it could theoretically be,
where it's like the only solution that any company uses for hiring?
Yeah, I think the main thing that's stopping us from being the only source of candidates for
companies is our candidate supply, right? It's really hard to run a two-sided marketplace,
because you've got to balance, in our case, the number of candidates and the number of open roles
in companies. And keeping those balanced is really difficult. A lot of my job is running back and
forth between those two sides, where I'm like, okay, shit, it looks like we're running out of
candidates. All right, how do we turn that up? Oh, shit, okay. Now we have a surplus of candidates,
and I need to go back out and sell, or I need to empower other people to sell.
So I wish I were kind of better at that stuff, because it's really, really hard to keep things
balanced. And I think that maybe if we were more aggressive and just went all in on getting a ton
of candidates and then said, screw it, we're going to find the companies later, maybe that would be
a better way to do it. I just try to keep things balanced, and that may not be the best way to do
things. But so far, it's worked okay for us. Another thing that I think I did wrong is it
just took me way too long to get started. So after I put up that... And this maybe will be poignant
for your audience. So don't make this mistake. So I put up that marketing site. We got all those
signups. And then it took me months to mobilize because I was terrified. And I wish that I'd just
found a co-founder or just went for it myself the next day, in retrospect, instead of just sitting
there being like, Oh, my God, what do I do? What do I do? I've been handed this gift, and I'm going
to screw it up. What finally got you over the edge to actually start moving? I just got really angry
at myself. It's the honest answer. Like, what are you doing? What are you doing, you stupid piece of
shit? Just like, you know, what's worse than doing the wrong thing is doing nothing. And it sounds
so trite. But coming to that conclusion, yourself can take time. There's a lot of stuff like that,
where you kind of just have to have that raw emotional experience on your own. And somebody
can tell you the answer. Somebody can be like, alien, here's what you need to do. They can tell
you what to do. You could read it in a blog post or a book. You could listen to it on a podcast
like this. But it won't really resonate with you or make a difference until you actually struggle
through it on your own and come out the other side. And you did come out the other side. You
are now running a team. It's no longer just you struggling by yourself to get something done.
I'm curious how your role has changed since then on a day to day level. You could still be getting
your hands dirty with everything. You could be sitting back and making high level decisions about
sales and increasing the supply of developers. You could be delegating a lot of the stuff as well.
So what's the balance like for you today? Yeah, well, we actually... So we brought on our...
I mentioned earlier, we brought on a customer success person who's under the sales umbrella.
And that's made my life a lot better. We've also brought on our first actual salesperson,
which has made my life better already. I guess a lot of my day to day is thinking,
like generally as a founder, you're spending time hiring always, or you're thinking about
when you need to do more hiring. One of my favorite things about my job is writing. So doing
content marketing. Our blog has been such a great channel of users for us. And it's also been great
for me because I get to write about things I care about most of our blog. If you check it out,
of course, I'm going to plug it. It's blog.interviewing.io is about data in interviewing.
So how deterministic are technical interviews? How consistently do people perform from interview
to interview? What happens when you make women sound like men in interviews and vice versa?
How does that affect outcomes? What matters in your coding style when it comes to technical
interview outcomes? Does it really matter if you write super modular code or not? And we've
examined all of these questions and a ton more. We've looked at what traits make people better
interviewers. And this is my favorite thing. I guess if I could just sit in a cave all day
and write, maybe I would. Fortunately, I can't do that. But to this day, because I really enjoy
doing it, I still do it. Though fortunately, other people on the team are now doing it as well.
I do a lot of high-level product vision stuff like what should we be focusing on?
What should our voice be? What features are going to get us the most bang for our buck
without as much work? Although again, I'm trying to work myself out of jobs on all of these. And
we have great people that work for me now that think about the details of that and probably do
it much better than I do. And then of course, fundraising is something you generally have to
do all the time as a founder, whether you're actively raising or thinking about raising or
thinking about what metrics are going to matter for your next raise. It's always in the back of
your mind. What's the future look like for interviewing IO? At what point are you done?
And at what point are you happy?
I'll be happy when hiring is fair. That may never happen. I also may never be happy.
I don't know. I really love what we do now. And I just want to do it as long as it feels
like it's fruitful. And it feels like we're moving the hiring world in the right direction.
People have asked me about whether I see an acquisition in our future at some point.
And my answer to that is always, if it's a partner that shares our vision for
hiring being fair, and if they can amplify our efforts, and if we believe in the way that that
partner has done things to date, then we'd be very excited. I would love to be in a position
where we're figuring out what makes people good at stuff. And no matter who people are,
we just can put them in front of the right opportunities, then I'd feel fulfilled.
But short of having a bunch of resources and a partner that's going to do that,
I think we're just going to keep doing what we're doing and try to do more of it.
Sounds good to me. I've kept you long enough, Aileen.
It's kind of a tradition. At the end of every episode, I ask you what your advice is for people
listening in. We've got an audience full of people who are primarily, but not exclusively,
software developers working full-time jobs. And a lot of them are considering starting a company,
considering starting a startup of their own. What's your advice to somebody in that position,
Aileen? I think you just dip your toe in the water.
Sometimes you think you're sitting on the best idea ever. And if only you had the
fortitude to get out there and do it, then everything would be great. The fact is, whatever
idea you have is probably going to be very... Either it's wrong or even if it's right,
it's going to change a lot. So you don't have to be so attached to that particular idea and put
all your eggs in that basket. But if you do think that you're onto something, find a way to try it
out. In our case, it was putting up that marketing site and seeing if anybody signs up.
That's not the solution to everything. Some businesses are much more complicated than just
putting up a marketing site saying, join our waiting list. But many businesses aren't.
So think like, what is that core idea that you have and how can you validate it very,
very fast? And then if it looks like there's something there, then go all in. But I think
just seeing some encouragement from the world where somehow the world says back to you,
I want your idea, is going to be very fulfilling and is going to make it easier to take that plunge.
But before you take the plunge, you can just dip your toe in the water.
Dip your toe in the water. You heard it here first.
Aileen, my pleasure as always talking to you. So glad you came on the podcast.
Thank you.
Can you tell listeners where they can go to learn more about what you're up to with
interviewing IO and what's going on in your personal life as well?
If you share that sort of thing online.
Well, you can go to interviewing.io. You asked me stuff I did wrong. I think like
there's sort of a blessing and a curse when your name is also a domain name.
But that is the name of our company. That is where you go. Please check out our blog.
And if anybody has questions about starting a company or hiring or anything, you can email
me at Aileen, A-L-I-N-E at interviewing.io.
All right. Thanks so much, Aileen.
Thanks, Cortland. You're the best.
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