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VIDEO TRANSCRIPT
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Title:       17 Year Old Raised $32.4M to Connect a Billion People – Bailey Pumfleet | The 021 Podcast
Channel:     Siam Hossain (https://www.youtube.com/@SiamMH)
Video URL:   https://www.youtube.com/watch?v=U5ZYJMPAUYo
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a a quote that really sticks with me and I always paraphrase this but it's Warren Buffett's quote um
when others are greedy be fearful when others are fearful be greedy we used to use kalanly and our
entire organization switched to cal.com this podcast itself was scheduled through cal.com we are
here to connect anybody you know crazy idea it's really out there but what if we made it like really
free for individuals like Gmail free like the refugee camp which is using cow.com to schedule
incoming refugees with uh you know doctor's services or immigration services. I don't think you'll
find an item of clothing above like $10 in my entire family's home. You raised 32.4 million total.

Bootstrapping is awesome because who doesn't like to, you know, stick their finger up to the VCs and
be like I don't need you.

Did you face any issues being an immigrant here?

You anything can happen. and they can just, you know, take away a visa whenever they want. Every
time you go to the border, you get questions, what do you do? What are you a founder of? What what
made you deserve the 01 visa? The burden of proof there is like so high. But the thing that will
keep you awake every single night as any good founder is you're like, why are we not doing more?
Welcome to 0ero to1. I'm your host Sam Hussein. I'm an immigrant founder. I boost up my company to
seven figures while creating a community of 220,000 members. Currently, I run a hedge fund for
immigrants. I started this podcast to share 0ero to1 stories of people who started with nothing but
created something meaningful and impactful despite the odds. Today's guest is Bailey Pump Fleet, co-
founder and CEO of Cal.com. It's an open-source scheduling platform. They have raised 32.4 4 million
handled over 10 million in bookings and wants to connect 1 billion people by 2031. Without further
ado, let's dive in.

Bailey, I met you last year, almost a year now.

Yeah.

And I remember when I met you, it was kind of like a fanboy moment for me because I have been
already using Cal.com by that time for almost two years. We used to use kalani and our entire
organization switched to cal.com and then I met you and I have been following you since then uh and
I've seen your growth and interestingly actually this podcast itself in this venue was scheduled
through cal.com that was uh kind of like a interesting moment and you're very public about your
vision for the company which is connecting 1 billion people by 2031. So I wanted to dive directly
into the question that how did you come up with that specific date? How are the numbers now and
what's the road map?

Yeah, I mean uh 2031 was just 10 years from when we started. So we did start in early 2021 and you
know the vision for cow.com has always been a mass infrastructure company. We are here to connect
anybody no matter whether they're just you know random individuals booking each other. So that could
be friends, that could be small businesses or that could even be governments and enterprises and
things like that. So you know, we really wanted to shoot big and we look at companies like WordPress
and things like that on how they power like half of the internet and things like that and we really
wanted to shoot for a really ambitious number, say like a billion people um in those 10 years. And
now, of course, we we never imagined it to be exactly linear progress. Just like anything with
cow.com is very exponential. I love going on to all the dashboards and metrics and and watching just
the the number of bookings, the number of users, everything just climbs and climbs and climbs. you
know, on cow.com alone, we're um just over 10 million people connected and uh across all of our
self-hosters and things like that because, you know, we're open source. There are different people
running their own instances. I think we're around 30 million across all self-hosters. So, yeah, we
really want to build this sort of like network effect of just infrastructure and something that's
just so embedded into the web, into technology itself, much like WordPress or things like that. um
where it's not necessarily super centralized but through the power of open source it's just
everywhere and then you know in those 10 years from now I should be booking my doctor's appointment
I should be booking anything you know all of these podcasts should be booked on cow.com there's no
uh there's no reason why we can't be the the operating system for everything scheduling related

I mean that's an interesting I always was curious 2031 so specific 10 years did it change after you
started like did you recalibrate your goal now or like how is that or it's still 2031?

It's still 2031. We're still going to go for it. You know, it is a very sort of outlandish goal. Of
course, we we recognize that from the start. You know, we don't mean to sound like every other
overaspirational set of founders. But that being said, a lot of what we started off with, a lot of
what we have now remains fundamentally the same. Um, we've always had this kind of tagline of sorts
since day one, which is scheduling infrastructure for absolutely everyone. And throughout the four
and a half years that it's been, we never really deviated too much from it. That was always the
long-term vision. And that still plays the biggest part in what we do. Um although of course we
spent like the first year building consumer then we built you know teams which was like small SAS
you know over the long term we're always working towards this goal of truly truly creating that
infrastructure for everyone and so I think that's one of the things that's been really remarkable
you know a lot of startups pivot you know like I've done that before everybody's done that but
what's been incredible for us is just how um almost unwavering our goals, our mindset has been since
even coming up with the idea of the company, let alone incorporating it or even formally starting
it.

When did you start like Cal.com or like when did this whole thing start?

Um, it was it was around April 2021. I know we we launched on April 15th, 2021. Me and my co-
founder, we spoke in the in the early days, kind of worked on it a bit throughout late February. And
basically what happened is is once me and my co-founder met each other and decided it was a good fit
to be working together. Once again, we set an outlandish goal. We're launching on April 15th. It
doesn't matter what has been shipped. It doesn't matter what hasn't been shipped. We're launching.
And so we really had just a very fixed deadline as to when we actually needed to put something out
there. And uh I worked as hard as I could towards that that launch date and pulled many many like
3:00 a.m. nights every night. Um definitely fun times, definitely a lot of good memories. But yeah,
I mean I think it's that thing of just like set yourself that goal and and try to stick to it no
matter what. And that's something that I try to apply throughout like personal life and things like
that. Um is just a very concrete goal.

Yeah. So couple of good points there. One is setting the goal. How old were you when it was like
April 15, 2021?

I was uh I was 17.

17. You're not even at the age of drinking alcohol basically. Like you're

No. No. How did you like come up with this idea of like solving a scheduling problem and not going
for a like there are so many that time like you could have gone for crypto, you could have gone for
like just a AI I mean AI wasn't as hyped back then but it was still kind of going there. Why? I mean
I shouldn't say like boring but topic like scheduling is not the sexiest thing people can solve.
what made you get into this?

Yeah, that's absolutely true. And I think in general, it just really goes back to like the kind of
person that I am. You know, I don't chase the latest thing whenever anybody says, "Oh, have you
watched the latest Netflix show?" You know, whenever everybody's saying, "Oh, have you seen Squid
Game?" Chances are, no, I have not. Um, and you know, I don't I don't get influenced by what
everybody else is doing. And so I've always remained a skeptic of a lot of new hyped up technologies
and and that was crypto back in the day then web 3 and I was always like ah I don't really believe
in this and even to some degree AI now I mean I think AI is absolutely here to stay. I think it's
proven the the test. It's crossed the threshold

but uh I think everybody right now is just scrambling to embed AI into their products no matter
what. And you know, if you're not working on AI stuff right now, you're a laughingtock. But I think
that sometimes the better approach is to sit back and wait. I think if you look at Apple right now,
everybody's laughing at them because, you know, they're they're not really progressing with AI. But
at the end of the day, they're going to sit and wait around, wait till everybody's, you know,
finished the race of building the best like foundational models and then they're just going to go in
and like buy anthropic or buy, you know, something like that. Um, and I think that there's something
pretty smart in that. You know, for us still, we don't chase AI features. We we sit there and we're
like, "Okay, we're doing something very fundamental here. Let's just focus on that." And then, you
know, AI features and things like that. Let's truly see what the market wants without all the hype
first and then we do it. And so, yeah, over time, as much as everybody thinks, you know, let's do
web three, let's do that, has never really been what it's about. And I think that I really do
believe that the the strongest companies do the most boring of things. Well, like the huge
companies, Docu Sign, like does anybody care about document e signatures? Is that a fun thing to
build? No. I am the most boring guy to talk to at networking events when they say, "What are you
working on?" I always feel like I go to networking events and they're like, "I'm building the an AI
product that lets you talk to your dog or um I'm building this crazy decentralized web 3 whatever."
And I'm like, "Yeah, I do scheduling." And in a sense, that's kind of boring, but I genuinely
believe that that kind of results in the best companies. I think if you take any large startup that
you think of like Stripe, God, payment processing, that that's a hellish nightmare. But the thing is
is companies like Stripe, I mean, we're all very bullish on because they solve something fundamental
that nobody else wants to solve. We just solve something else that's fundamental that nobody else
truly wants to solve.

Yes. What an amazing like the first learning uh from you is basically like boring is cool. like we
have to make boring cool again. Um and something I can relate to personally on with you here because
I have also seen a lot of these hypes like technology in general as a field goes through all these
innovation. Uh but if you are sticking to one focus like that that has been I think like your main
thing that you are like not getting deviated with whatever is coming because there are always
something new coming in technology. So that is something very interesting your focus. Um I'm really
curious and I was curious. I wanted to ask you this question for a long time. Um is that I want to
understand how your mind operates from your childhood perspective like how you grew up. Is there
anything in your own operating system which made you this way? Not chase the FOMO you know. chase
the boring having this focus like what made you this way because we can take whatever is built on
cal.com let's say and you can start from zero again but I think you can again do it because your
mindset is already like solid so tell us a little bit about like your childhood how you grew up and
what are the things we can yeah share your story

yeah and it's a great question because I really do owe so much to my parents my childhood and the
experiences that that entailed. And I see a lot of similarities as to like how that just influences
me as a person today. So I I grew up I grew up just east of London. Um in a in a family that like
was relatively poor. My my parents always worked like super super hard. Uh my dad has worked really
hard throughout his entire life, even still to today. And you know, we grew up just being
complacent, never like chasing the the material things. Um, I actually made a joke earlier about
this to to someone else on my team, but I said, I don't think you'll find an item of clothing above
like $10 in my entire family's home. Um because even though that through just pure hard work and
dedication that my my dad brought us, you know, like up into, you know, comfortably middle class
now, I think a lot of those traits and those experiences and things like that really stay with you.
And so I think that we we sit in a reality today where yeah, of course it's about not chasing the
the shiny new thing. And that shiny new thing could be a I don't know a Gucci belt or it could be
you know like web 3 or AI. There really is something to just value about just good like going back
to basics. Good hard honest stuff. Um and that's really what kind of like scheduling is. That's
really what any of this is. And it also changes the way that I operate as a founder. I think there's
a lot of people say oh I don't do this for the money. I mean like 90% of founders do it for the
money. the 10% that don't are doing it for fame or something like that. But, you know, for me
genuinely, I'm really driven by the vision of of cow.com. And that is the thing that keeps me going
every single day. And, you know, without trying to sound like everybody else is saying this and be
such a cliche, you know, there have been times where we have had an opportunity for an exit. Um, you
know, one way or another. an exit that would probably have put me, my co-founder, and even the team
in like a a very nice financial situation, we'll just say. And I'm just like, "Nah." And they're
like, "Huh?" Like, you didn't even really think about it. I don't really sit there and deliberate
about it because that connect a billion people by 2031. That's what drives me. Like, I cannot give
up on this thing until I have fulfilled the vision of maybe not necessarily a billion people. You
know, that's a that's a very sort of like quantitative goal, but but rather on the qualitative side,
I want in 2031 to be in a in a situation where everybody's using cow.com and it becomes a household
name much like, you know, if I want to send you some money, I'm just going to Venmo you. That's
become a household term. Like, I want cow.com to just become part of everybody's core stack. And
then as well as that, you know, I want to work with all of these businesses and governments and
charities and things like that to just make all of the scheduling inefficiencies easier. Like
everybody jokes to me like, "Wow, can you guys partner with the DMV and things like that?" But in
reality, we've worked with government organizations that have like made things so much better for
people. you know, we we work with uh a part of the Brazilian um government where when you get like
passports and ID cards and things like that before it was first come first serve basis. So people
were queuing in like the cold and the rain outside in the morning um you know waiting for their like
ID card collection and now they just book their appointment on cow.com and it's wonderfully easy and
there are there are so many other use cases and examples and you know for me the the stories that
mean the most to me are not the times when we closed a sevenf figure deal or something like that but
it's rather the story I hear about the the refugee camp which is using cow.com to schedule incoming
refugees with uh you know doctor's services or immigration services and and things like that as as
they come in um you're just connected viacow.com with the experts that you need and you know that's
making a real impact on people's lives and and that that is the thing I'm the most proud of. I do
not sit here bragging about any numbers of ARR use count anything like that. The thing I really brag
about is that we make a difference in people's lives. And um you know that also goes out to all of
the tens of thousands uh of like small businesses as well which operate on things like cow.com. Um
you know we all have some kind of tech stack. You know what would you do if Google Drive disappeared
or you know suddenly Venmo disappeared or this? We all rely on some of these things and I just want
cow.com to be one of those things that that you rely on. So you know that's the thing um my
childhood taught me about dep like being dependent being just like sticking to the roots keep it
simple and just build something worthwhile. Yeah, thanks for sharing this because I when you're
sharing this whole thing. I realized that you are actually building something which you yourself
experienced as a child is that you're very ground it seems like you come from a very humble or
grounded family. Uh I mean thanks to your parents to be honest for raising you and essentially with
the tool you're creating you are you want like to help like average people help basically that's the
that's the goal you want every average family every average small business to use this tool and feel
that how it helps their lives become simple that's awesome man I actually didn't know this like this
grounding story. Um, I think you also basically like changed the name. I I saw that in hacker news I
I was just doing some uh like research on you that 2021 hacker news you launched and it was called
kalenzo. Why why change the name? And the reason I'll ask you why I'm asking this question because
like I have thought of changing my company's name couple time because like is it too big? So yeah,
like why did you change and what was the motive?

Yeah. Um, we launched as Kenzo. Um, it was just one of those domains that was available to be
honest. You know, nowadays you you want a.com, you don't exactly have the pick of the bunch. Um, so
yeah, Kenzo was the original brand name. It was okay. We had we had a nice little branding and
design guidelines and things like that, but it was like it was like a cute little competitor. it
didn't really scream like we are the scheduling um you know software and um you went a few months in
um we were obviously going along doing our thing growing and we really started to think about like
we we need a really good brand name I mean first of all we're in the link sharing business um you
know I am cow.com/bailey I tell you book me cow.com/baily cow.com this it sounds a little bit better
than kenso.com /bailey. Um, more the more syllables, the less, you know, cool it is uh to to tell
someone your scheduling link. But no, I mean, uh, we we looked at various brand name options and,
you know, especially for acquiring a a.com like that can get very expensive. But like I say, half of
our business is link sharing and we wouldn't be we wouldn't be who we are today if we weren't
cow.com. Um, people wouldn't look at us the same if we were Colenzo. And not to say that, you know,
go buy a one-word.com and you'll suddenly be the best company on earth, but it certainly like
commands a a respect, like a persona around the brand. I kid you not. Like, you literally see it um
you go tell somebody brand new about this stuff and I'm like, "Oh, yeah, it's cow.com." And they're
like, "Oh, that's a nice domain name." and you you immediately see their brain just turn on. And I
use that in the context of say like a networking event where like a million people are going to
pitch you their startup and you know you're not really going to care about like 99 plus% of them.
Soon as I tell people cow.com that oh let me check that out. Oh you have a you have a nice name and
then as well invest in the branding. Um we put a lot into design and branding and things like that.
they see the landing page, they're like, "Hm, this looks nice." And I kid you not, that motivates
people to sign up by like multitudes more. I'd love to get a some kind of study one day that
actually like quantifies this, but it's absolutely incredible just how more interested people are in
the brand when you've got like a a short brand name like that. So, um I always think that changing a
brand name is one hell of an expense both in terms of money and time and you know formerly known as
Kenzo for a while but wow is it worth it. Um I always say just in terms of like the money I think we
would pay many times what we paid for the domain name and it would still be worth it because it just
really makes you who you are. I I agree that I also love gal.com's name and also the branding around
it is that you give everything very simple and minimalistic. There is something about your overall
uh execution that it has to be very minimal and it's not so glossy. It's like flat design. Even the
design is very flat and simple and cal.com so easy. How would you mind sharing how much did you buy
it for? Is it a disclosable number? You know, the weird thing is with uh with a lot of these domain
acquisitions, most of them have to be under NDA,

I assume. So, it's we can't go tracking down the dude that sold it to us and then we know like how
much money he now has in his bank account.

Sure. But figures wise,

yeah, it's it's definitely well into the the seven figures. And and when it comes to like
oneword.coms, the range is so wide. You have some people who bought incredible oneword.coms for like
50k and then you have some that paid like 30 million and you know like I say that is really a range
but although we we definitely paid you know not not up in the 30 million for sure but you know we'll
just say into the seven figures

um

it was still it was still very much worth it um and yeah I mean like you say the investment in when
you add on the investment in the brand and just really nailing that stuff as well. That's been just
tremendously helpful for us. I guess the uh the secret thing about our brand is that it was uh I
actually got inspired by Uber in particular um for this the very black and white design, very
functional user interfaces. Um because once again, old people have to use Uber. You want it to be as
just like bold and easy to interpret. Um, and that's essentially what cow.com is supposed to be.
Now, over time, I've tried to make it, you know, a little bit, you know, polished and make it look a
little bit sleek, but at the end of the day, it's always a very like black and white minimalist,
very clean, very unopinionated as well, cuz the unopinionated part about the design looks really
nice for businesses that want to like white label um, and everything like that that you don't have
to replace. Back in the Kenzo days, it was a light blue, you know, just some generic light blue that
probably everybody uses. Um, but you know, the the user interface would feel very opinionated and
things like that. Whereas cow.com now is just almost like a a blank canvas, albeit a very functional
one. Um, that everybody just kind of looks at and they're like, hm, you know, this is this is very
neutral. This is very adaptable.

Yeah. Yeah. Simplicity rules. I think you obviously had to have some money to be able to buy that
domain. So, we'll go to that stage like it was a later stage business decision. But how did you get
your first like literally first customer? I was doing some research also on this and I saw that I
think you guys launched in product hunt and you had almost like a thousand signups or something and
I guess I wanted to know the early stage because once you are in the millions range you are a little
different stage of game but tell me about your first dollar the first person who paid you. Yeah,

you know, back in back in like the late February that I said when we even kind of started to work on
this, all that Kenzo was effectively was just a landing page with a weight list sign up. Um, it's a
habit of my co-founders where like if he's exploring an idea, he'll buy the domain just like
everybody else does. Um, build a little landing page but put like a weight list sign up. We do that
as well for many sort of like subproducts, features and services within cow.com. just stick a
landing page out there with a weight list on it and see how many people sign up. Um, that was what
Kenzo was in the early days and you're right, there was a thousand people signed up to that weight
list. Um, we ended up drumming up some interest uh by creating like a community Slack, posted some
like regular updates in there, tried to get people involved. Um, worked decently well. And then, you
know, I I said that we just we set this date far out. And part of that reason was is we wanted to
build people up and build a clear momentum up to a a singular sort of launch. And so yeah, we
basically told everybody on the on the Slack, mark your calendars. April 15th, we're launching. Then
we start prepping. We we reach out to like everybody we've ever known. To be honest, I'm not just
going to say friends because like when you when you're doing your big launch for your startup, you
reach out to like anybody you've ever known. even like that dude from five years ago that's like,
you know, 10 hours of scrolling down in your messages, you know, like you message everybody about
this stuff. And we just built up uh an absolute army of people that at 8:00 a.m. or whenever it goes
live on Product Hunt on the 15th that there's like a bunch of people that just, you know, give it
that kick off the ground because like with anything, you know, success is compounding. If you're
already at the top of Product Hunt, more people are going to see you, more people are going to
upvote you. Um, that applies to literally anything. That's why tweets either have like 13 likes or
130,000 likes. So, yeah, I mean, we're we we rallied everybody. They absolutely like came and
delivered. Like I say, also on the day just like calling up anybody you could, you know, share this
around. Oh, I think like I don't know how many members of my family got a Product Hunt account that
day to upvote Kenzo on launch day, you know, but yeah, I mean that that little kick off the ground,
that's all all that you needed to just like start that momentum. I think everything in life is about
momentum. Um, and it's never more true than when it comes to to launching something. So, yeah. Um,
launched a we we actually started as it was a paidon product. It was it was 15 bucks a month. There
was no free plan. And I honestly don't think I even knew how to build a free trial. Um, so it was
literally just like a paid product. And yeah, I mean that morning we get like a Stripe notification,
you know, like $15 invoice generated too and then just like a random customer name. And we were
like, "Wow." Um, there's always like it's always a remarkable moment. like it doesn't matter. It
doesn't matter whether you're making 10 bucks, whatever. I see these tweets on Twitter all the time,
people like starting their first startups and it's like that's just such a such a relatable such a
um incredible moment. And yeah, from there it's like it's like droplets of water. You drop, you
know, $15 drop drop. And throughout the day we were watching as as you know, definitely like
hundreds of dollars of um of subscriptions were started. um even on that day and it was like wow
this is like this is really cool and yeah it's definitely one of the most memorable milestones

definitely because it's the first 021 the excitement when you uh basically launched like you said
like you didn't have the trial you went directly to paid how did you build the trust around the
product that people are like like was there some trust built around you or your co-founder like how
did how were people comfortable paying that where there are gallanly or like other giants already?

Yeah. Um I honestly don't think there was like a huge amount of trust or anything like that. It was
simply too early for that. And you know who are we? Just any old pair of idiots that that built a
little SAS app. But I think in reality the thing which really got people um to to kind of like
subscribe or or sign up or anything in the early stage is we were open source. We were the
opensource calendarly alternative and people love open source. Um open source is just such a a
strong beautiful community, a community that we that we love and is still a very sort of like close
part of of who we are and our values and things like that. And yeah, there's a lot of people in open
source that like you want to support open source. I I do the same thing. If I can go ahead and use
an open source product, I'll use it. if I'll donate to them. I'll, you know, like sign up if they
have like some kind of paid plan and they're doing like a little bit of a commercialized open
source. Yeah, I love supporting open source companies and so do a lot of other people in that kind
of space. So, in the early stage, I think that we did we we hinged on like open source as like day
one. Then like weeks two and three, it was like, oh, cool new product. They're like they're giving
it a bit of a a new design and certain new features, you know, just a few bits. So then we got like
SAS enthusiasts and then over time we built it up into being like a a real viable product. But I
honestly think um I don't even know how long this was. I think there was probably a period of like
three or four months where I just did not think that like Kenzo was even really a viable competitor
or like a viable product to Calendarly. Um, in all honesty, as much as I of course did send
everybody my Kenzo link, if it was me, I'd have probably just used Calendarly. um cuz say what you
will about Calendarly, but it's a damn solid piece of software, especially for um you know, just
like an individual taking bookings. So, there was always that um imposter syndrome almost that um
are we are we a viable Calendarly competitor or are we just some like niche cool little thing that
people, you know, are like, "Huh, I'll check this out. I'll sign up. We'll see."

Yeah. And like when you actually launched uh I love that you basically went open so open source was
basically kind of like your crowd originally. Were you intentionally open source from day one like
that was the goal of the company like you will start as open source company. Yeah, we were more or
less open source from they minus whatever because like the like I say the original landing page with
the idea that was open source, you know, we always said like it's going to it's going to be under an
open source license. You can do what you want with it. It was a real fundamental part to who we
were. Now that being said, that's one thing that has really changed about us and we uh we
overestimated how big of a part that open source will play in the real world business. So as much as
I say open source and the community and everything like that is is terribly important to us and you
know like we are big open source people. We believe in like you know we believe in it and everything
like that. In reality cow.com is not what it is because it's open source. Not today. To some degree
it helped us get off the ground. It helped us become noteworthy remarkable. Um maybe it could be
fair to say that we wouldn't be where we were um without it. But um you know nowadays cow.com is
cow.com because it's simply just the better um scheduling product out there not because oh it's open
source let me try this thing. So yeah the the initial crowd was definitely open source enthusiasts
though and I'd be lying if I said it didn't help us. Yeah. And I I am maybe wasn't in your original
crowd because like and like that is a great business learning here is that like always having the
crowd like early stage you need that support. I was actually honestly I switched to cal.com for a
very specific reason is because your advanced feature when I started rolling it was like for a free
product it was so much it has so much uh capability like I could approve my bookings which is like
very important for me to actually make sure that not not everyone is booking my calendar and I was
like I think that was my main single reason but you have so much feature for the free product. I'm
like, wow. Like, why would anyone use any other tool?

I want

Yeah. Like, I mean, for for a free product, honestly, honestly, your free version is already very
good. When we did the rebranding, that was kind of part of there was 2.0, there was announcing the
series A, there was the rebranding, and there was the free there was like the free plan. And I
remember this was like this was just one of those like crazy ideas that me and my co-founder
mentioned on like one of our daily calls. We were like, you know, crazy idea. It's really out there,
but what if we made it like really free for individuals? Like like Gmail free, like there's nothing
to pay. And we were like, yeah, that's crazy. That would be cool, though. That's crazy. That would
be cool, though. You know, and then over the next few weeks, we're like, that would be cool. That
would be cool. Until we formulated it into a real plan that cow.com is truly free for individuals.
One of the best moves we made.

Yeah. Yeah, I agree. Um so like you started as a B2C what I'm understanding because like individuals
when did you transfer to like B2B or enterprise customers and tell me a little bit about like your
first customer I guess enterprise.

Yeah. So um you know what I said earlier was that cow.com has been pretty unwavering in its long-
term vision because you know we always wanted to be serving these like infrastructure use cases but
the thing is is we had to start somewhere and after the product hunt launch nobody really cared if
we made scheduling APIs or enterprise stuff you know we had to address the people that supported us
and those were the consumers. So we started out yeah being pretty BTOC in the sense that we were
just trying to build like the best individual scheduling product there is. And that means that we
build all these little things that everybody so desperately wanted from the other competitors over
years and years. Like for instance being able to approve or reject a booking based on like the the
context of it. um which you know is something that like pretty much any busy founder, you're going
to get random people that email you that try to book your links and you want to have some control
over that. So that's kind of where we play into the whole typical thing that everybody says listen
to your users, build what your users want. Um that kind of thing. And that's where we had to that's
where we had to sort of fulfill that. But the the consumer side is just like the first part like a
four stage plan. And we this is the plan that we really didn't waver from. It's um we have the the
free plan. Then we have teams which is just good SAS. You know if you're working with multiple
people using cow.com in a business context uh there are like collaborative features and things like
that in there. It's just nice little self-s served SAS. And then above that we have enterprise which
was building like the the industry's first truly enterprise ready um scheduling solution because
there aren't any out there that are actually um that have all of like the check boxes that a true
enterprise company would need. And then finally the the fourth and final tier is that scheduling
infrastructure, the APIs, the things that you need to build cow.com scheduling technology into your
platform. And that's what we kind of like executed across for all that time. So, and it really went
like that. You know, I remember our first, you know, individual customer back when it was paid, but
then I remember like the first teams plan upgrade that was like a huge sort of like feature release
and everything like that. We we released teams and back then the only difference in the team's plan
is that you could do a roundroin event. That was it. had like one tiny little like selection for a
roundroin event and I was like nobody's gonna pay like a 15 bucks a month upgrade from a free plan
just to get like a roundroin option. Couple days later, yeah, somebody bit on on Stripe and I see
the notification. I'm like, huh, that's that's cool. Um, and we're like, we really need to add some
value to this now to, you know, to not, you know, disrespect the uh the people that are paying us
for this. It's been so exciting every time we we spend months and months of work building the
enterprise product. That was a long time huge engineering effort and so much brainstorming. So much
everything goes into this and then once again you get your first enterprise customer. It feels so
rewarding each time because it's really just a continuation of when you get your first customer day
one. You know, I think that a lot of founders have spent a lot of time building something for it to
just not take off. It just flopped. That was honestly what half my life was before cow.com. I built
things and they flopped. And so to get that validation of like, wow, somebody's ready to like, you
know, hand over some money for this. It doesn't just stop once you've got your first customer on day
one. It really happens every time you sell a new product or feature or add-on or something like
that. And each time it's a really beautiful experience.

Yeah. You have this single KPI which you're following is about Yeah. delighting your customers uh
they can change over time. Um I wanted to learn a little bit about like your highest ROI decision
you have made where I guess like you made a very small change tweaking in your process but it had a
massive jump either in the MR or customer acquisition like it could be an simple UX improvement I
don't know what you changed pricing improvement but it has a huge bump and you're like so surprised

I think it's definitely just in terms of like quality assurance I think one thing that everybody's
probably heard from somewhere before is like as a founder always keep your finger on the pulse.
That's a lot harder in reality than than you'd think and especially when my work nowadays is so
abstracted away from the product. Like I don't code anymore to be quite honest. I don't even use the
product a huge amount because cow.com is a lovely like set and forget piece of software. like I go
in to say like, "Oh yeah, I'm going to be in like SF next week, so like change my time zone for
that." But aside from that, I don't log in too much. And uh you know, a few months ago, I went in
and I was like, "Okay, I'm just going to like private tab uh one of those disposable email
addresses. I'm just going to sign up for this from scratch and, you know, just take screenshots and
put it in Figma and just add comments everywhere." And wow was I surprised. Um, turns out that if
you just let engineers build things without too much oversight, then your product will have shitty
UX. But yeah, there were so many little bits of lowhanging fruit, all little five minute fixes and
things like that that I could just go around and um and fix. And that has made such a huge
difference um in just a how the product feels, b it reduces a lot of customer confusion. There there
were people were shipping new like advanced configuration options and just putting them like smack
on the main screen and I was like there's like under 1% of our users are going to use this. Like
let's tuck it away into like an advanced section um and things like that and that leads to people
being less confused. It also helps upsell people more, especially if we go from like free to teams
or teams to enterprise, which you can all do self-s serve. Some of our self-s serve flows were
lacking to say the least. And just simply going through and you know, at the end of the day, it's
the founder that always has the vision, that always has that attention to detail for the product
that nobody else does. Harness it. I know everybody says it, you know, but you've really got to um
just keep your finger on the pulse always. I always know as well, the other one is uh one day you
should uh you should just apply for a job at your own company and just be, you know, like undercover
boss or something like that, you know. Um go through the experience because you find all of these
things that you're like, "Oh my god, like who approved this? Who who's responsible for this?"
Because yeah, you're the only one that's really going to catch that stuff out. Yeah. Uh, you have to
be the user yourself like once in a while. Um, I wanted to move to a little bit like funding because
people are always interested in funding. You raised 32.4 million total, 7.4 4 in seed and then 25
million u in series A and you have big names like Alexisan from Reddit or 776 and then Toby Lutk
from Shopify, Naval Ravikan, Balaji, Anthony Pump like all the mega celebrities in the field. How
did you like get to know these people or how like tell us tell me a little bit about the
fundraising? Yeah, fundraising was uh both simultaneously fun and terrible. Like I said, everything
is about momentum. And I remember when that first droplet hit, and that was actually on launch day,
I got an email at maybe like 10:00 a.m. in the morning or something like that, and it was uh a VC
reaching out and saying, "Hey, I saw your um I saw your success already on Product Hunt." and you
know really cheering for you guys. Um you know like hope the day's launch goes well. I would love to
like chat about you know like a potential fund raise. And I was like oh wow. Turns out that guy then
went on to lead our seed round which was crazy because he was literally the first guy you know that
that ever uh messaged us. But then once you talk to one VC and then you talk to another and it's the
same thing with angel investors too. They all talk. all VCs and investors and all that, they all
talk. And so if there's a if there's a cool startup that comes across the table, if I put in a
check, I'm going to tell you, "This startup's really cool. By the way, you're going to put in a
check." Um, all that sort of thing. So, um, that's actually probably one of the most effective sort
of like networking things I've seen in operation. Like, if VCs think there's a cool company on the
table, like, wow, you'll meet so many people so quickly that you never knew was possible. And so by
just building up um you know more and more hype and more and more taking over Twitter, Product Hunt,
uh Hacker News, all these sort of things which of course leads uh VCs to find you and angels too.
But as well as that, the all the intros and all of like the VCs like sharing notes on the back end.
Um that just led us to having an absolute array of investors that were just dying to invest to the
point that I mean we were lucky. This was also 2021. I was I'll say that, you know, a little bit of
a cheat code, but you know, we literally had to like either turn away VCs or we had to tell certain
angels are like, "Oh, let's put in a million." And I'm like, "No, no, no. Like, let's do like 250K."
Um, like like chill. We don't have um we don't have the space for this. I mean, we were over
subscribed, hence the point4 on the end of the 7.4 million. But yeah, very very exciting time and
very validating to see people so ready to, you know, like write checks for this sort of thing. But
yeah, genuinely do cool things and people will come to you and that's going to put you in like the
best possible seat and the best possible leverage to get yourself a good deal. You know, I think
that one way or another you can get in front of a VC. I think that's possible for for everyone, but
that's not really the question that anybody asks. It's always um it's always about like how do you
raise a really good round? And in a sense, the best way to do that is never reach out to a VC. We've
never I've never sent a VC outbound email as it's all been inbound. And I mean, of course, maybe we
were lucky in that sense, but if you're building something truly cool and making waves on the
internet, VC's entire job is to see who's making waves on the internet. And um I think that that
aspect, the aspect of just like put everything else aside, just like heads down and build something
cool, that is probably one of the biggest components as to why we raised two I'll just say like very
preferential rounds. Two rounds where we're like that's great. I haven't given away too much of the
company or control or just you know any of the rubbish that's usually

Yeah. I coming back to the basics uh build something people love um and you have been like focused
on the product honestly if I could I would invest in cal.com I saw that you have like 1% of the
customers who have like 1% like very small of the customers who also owns part of the company

it's really cool to see that

yeah yeah um I think last year when we spoke you you are already profitable and growing and I don't
know if you are like thinking of buying back some some shares from the investors. Uh did that happen
or like uh did you buy back some shares or like are you like stable on that side?

We we didn't actually. Um although it is an idea that still remains in our minds and I can't help
but smile as I as I say that you know because that's a very fortunate position for us to find
ourselves in. I mean the benefit is is we just truly have such a wonderful cap table of incredible
investors both you know institutional and individual. We really love having all of these people on
board. Um and the only kind of adjustments that we really make to look to the cap table is people
who may not want to be there. for instance, uh, ex employees who left a few years ago and they're
like, I could really use this money to like buy a house, then, you know, we we probably find a way
to connect them with someone else or or something like that. But, um, you know, in general, although
it's an option that we have, um, we do actually really love our investors. And I think that's I
think that's quite a lucky thing to say, but I think that it's it's very much sort of a net positive
having them around.

Yeah. Amazing. I like what is your advice on and this is actually like almost advice for me. uh is
that basically I have been bootstrapping my company to seven figures and we're a different type of
company more focused on immigration but what is your thought on bootstrapping versus raising venture
like what what is your simple decision metric for early stage founders

yeah bootstrapping is awesome because who doesn't like to you know stick their finger up to the VCs
and be like I don't need you that's always fun and of course I I kind of played that game in a sense
that um when we raised is the seed round. I always said to VCs, I'm like, hm, maybe we raise or
maybe not. Like, we have plenty of money to fund this. Like, if I pull out my phone, I had like $600
to my name, you know, like total savings and everything. I was like, yeah, you know, do we need VC
money? Uh, only if it makes sense for us. So, that being said, it's always cool to like put off VCs
and wait till you get like a really good deal. And you know, I I sit here right now smiling a lot
because we always got such good deals. I'm not in a position where yeah, like we've ever given too
much away or any stuff like that. That being said, I think that the biggest companies are built with
funding. Um I think that that is just a reality that we see and I mean YC and VCs and all that,
they'll all tell you that and I think they even have some metrics. But truly, if you want to build
like the next massive massive companies, then yeah, VC funding is going to help you get there. It's
a it's a real thing. But, you know, there's there's applicability to it. There is a world where I
would build another kind of business, but not really be shooting for being the biggest possible
company. Um, and it's okay to do that. Um, I just don't think that maybe you're building the next,
you know, Airbnb or Uber or Stripe or something like that without any VC funding. But, you know,
like I say, it's it's kind of an each to their own.

Yeah, I agree. And I like your position is probably the best position in the way that you can
technically bootstrap if you want to. You could have,

but you wanted to go to a billion users and and you basically were in a very like sweet condition. I
wanted to know a little bit about your like struggle as a as an immigrant founder because you're not
from the US. You are from UK and I actually don't know which visa status you came with or

did you face any issues being an immigrant here

to some degree? Yeah. I mean, uh, it's the US. Immigration is never easy unless you marry a US
citizen, you know. But, um, there was kind of a point, yeah, 2023, midway through 2023. Um, we
basically made a decision, um, that like I needed to be in the US um, for for various reasons, but,
you know, like I needed to get to the US as soon as possible. And this was like uh, almost like
timesensitive. And then it's like, okay, great, but like how does one get into the US? Uh, and then
we hear about like the, oh, there's the 01, but like the 01 is not an easy feat. And sort of like
the burden of evidence and things like that there is is huge. You know, it it took quite a long
time. I mean, I actually so say halfway through 2023 um is when I decided I need to get to the US
and it was December 27th that I actually picked up the visa. I remember it cuz it was just after
Christmas and I was like, who wants to go on a trip to the US embassy? Um so, uh yeah, I mean the 01
is is never easy. And then you know I get here and visas uh visas get you in the country but they
also don't afford you many rights. And so no matter who you are really you're always very much
sitting like at risk of um you know anything can happen. They can just you know take away a visa
whenever they they want. And every time you go to the border you get questioned and they're like
what do you do? What are you a founder of? what what made you deserve the 01 visa? You're here for a
conference. What kind of conference? You know, all of that stuff. You know, you're at the the mercy
of them, not just being like, h, rip out the visa and then like send you back home. Um, so it was
really weird because, you know, moving to the US was not my personal choice. Like I I sort of had to
do it for the company. Um, but nevertheless, I realized that of course I'm trying to work on this
company for a long time. the US ultimately has to become my home anyway. You know, it's always
pretty scary that you know, your your immigration status is tied to the fact that your company is
doing crazy things and that like if if cow.com ever went into some kind of like stagnant period
where we're not like growing massively and doing crazy things, then they might just be like, "Yeah,
we're not renewing your visa. You need to get out." And it made me very like made me very anxious to
kind of like plant roots here in 2024. Once I moved here, only a couple months after moving here and
being on the 01, uh I was like, hm, there's a US election coming up in a long time down the road.
I'm like, I have a feeling Trump is going to win. I just had that like I just had that like gut
feeling. I'm like I also have a feeling that like if I want to go for the green card, it will be
tougher in that case. And so I was like, "Okay, let's go for the green card." And I get on a call
with the lawyers and I'm like, "Great. This will just be like it'll be just like the 01." And
they're like, "No." They're like, "If you want to do the EB1," they're like, "It's like the 01 is
like the top whatever percent and like the green card is like the top minuscule portion." And
they're like, "The burden of proof there is like so high." Um, and you know, as well, I think one of
the things you have to do is prove that you're of critical importance to the to the United States.
Like that's a that's a damning sentence right there. And it's like how how are most of us supposed
to achieve that? And so that's the thing that's like such a a struggle I think for for absolutely
anybody is that, you know, the the only path to safety, you know, we let's assume a green card to be
safety because it's kind of permanent is is tied behind. So such a high degree of achievement and
you know luckily as you can imagine cow.com can power many um very fundamental services in
government in healthcare and things like that and ultimately it's because of that specifically as to
why I was actually able to get the EV1 but you know you you're told that it's like such a high bar
and I have I have a lot of friends who do absolutely incredible things are like practically famous
their companies are doing so well, but because they aren't of critical importance to the United
States, they they can't get it. And that's crazy.

That is so crazy. Yeah. Um I cannot believe like a company like Cal.com's founder has to go through
this kind of stress. Uh but yeah,

nobody's exempt from it. And um you know, you can

and there's no way around it as well. Like you can get yourself immigration lawyers, but you still
have to do the work. like you still have to prove to the US that like I'm the one that's putting all
of that evidence together. And um I spent like so much time on so much time, so much money. Um it's
really not cheap. It's and that's that's the scariest thing as well is I think when you put together
like the total cost across the O1 and the EB1 it must be like 30 $35,000 or something like that.

Also the stress of not being here you know like the stress. So Bailey these are like some very quick
10 seconds like rapid fire questions silly questions. Um, dark mode or light mode in laptop? Light
mode. Favorite SAS application? Superhum. [Music]

Favorite open-source project other than cal.com.

I think it would be GitLab.

Tremendous project and organization.

Okay. Any recent favorite books? I got to admit, I haven't had the time to read for a long time. I'd
love to get back into reading, but

Okay. Um, iOS or Android? Oh. Uh, it's always been iOS for me. That makes sense. And is there any
like uh one word your team would describe you with? Like one word your team would describe you?

Direct. Direct. Okay. Awesome. Do you have any role models? I don't like traditional role models and
I always think that it's silly to to um to sort of subscribe to just one person's way of thinking. I
like to take a lot of inspiration from very like unconventional people. Like my dad is like my
biggest inspiration for sure. Um but you know I'm not one that is inspired by you know like the the
top people in our industry and things like that because none of us have any idea what we're talking
about.

Agreed. And your dad is a perfectly amazing role model. I guess I wanted to know a little bit about
your like like what is keeping you excited right now now that you're in a special position in
cal.com it's growing it's what is the moonshot feature you're really you cannot sleep right now

yeah I mean we're doing well like we're we're four and a half years in and we're doing well and you
benchmark us against startups and you know we're we're doing well but the thing that will keep you
awake every single night as any good founder is you're like why are we not doing more um you know
when you see companies like was it cursor and deal and things like that the fastest revenue growing
companies out there you always wonder like where's the gap between me and them and you there's
always somebody bigger than you to compare yourself to and I ask myself that question a lot and a
lot of the answer really lies in growth and go to market and things like that so the most exciting
thing for us right now is that we're typically a fully async, fully remote company. I'm the only
person in the US even. But what we're now doing is we're going to be opening an office in New York
and hiring a team of like really good like sales and marketing people to just like really own the
funnel start to finish and just build like a really cracked in-person team that are like sitting
there brainstorming, collaborating, put a whiteboard on the wall and start drawing. you know,
there's something that's really exciting about like the kind of productivity that that can unlock.
So,

yeah, I love that you chose New York as the as the center. I also am very pro New York for startups.
Um, any I would say like advice for the early stage founders like if you or someone who is starting
in 2025, the game is very different. any communities you would recommend joining or like how would
you tackle the startup space like SAS specifically in 2035?

Yeah, I think if I was to do it again um a quote that really sticks with me and I always paraphrase
this but it's Warren Buffett's quote um when others are greedy be fearful. When others are fearful
be greedy. Um always look for the angle that everybody else isn't doing. Whenever you look at, you
know, the most successful people, the most successful things in life, it's when others are looking
this way, look this way. I think that that's still the thing that we should be doing today. If I
started again today, I would not just jump on the AI hype train and do the same thing as everybody
else. I think with um you know, establish that in a sense, but if you really look uh what nobody
else is looking at, but what's such a such an important and fundamental thing, scheduling is one of
those things nobody looks at scheduling. Nobody really builds in scheduling. We don't really have
any competitors to what we're doing aside from say like Kalan Lee and a couple of like big like
incumbent players. There's no other startups that are like racing us to do the same thing that we're
doing. Um so yeah, always look where like nobody else is looking. Communities and things like that.
I would say don't stress it. Like it's always fun to like talk to other founders and things like
that, but I think that people push way too much importance on like networking events and things like
that. At the end of the day, like random people that you meet at um you know, a mixer event are not
really going to make or break your company. I built I did everything significant in Cow.com's
timeline from a house in a town just east of London. My co-founder lives on a farm in the middle of
nowhere. You could like yell at the top of your lungs and nobody could hear you. We're not here in
SF or here in New York, you know, like networking and doing all these things. So, really just like
heads down. Don't distract yourself. This is like your early days. What was the single biggest
mistake in your early days where which caused like losing your customer base? like you made like one
silly mistake and you almost lost your customer base. Oh, we totally got carried away with like ship
fast and break things, you know? Like that's an incredibly fun thing to do in the early stages.
Yeah, I remember the days where like I would just pull out my laptop, spend a couple of hours coding
and just ship a new feature. But there comes a point where you really do have to, you know, mature
your engineering efforts and always find that balance between never shipping anything but being
stable. Um, and you know, being on the cutting edge and shipping things and breaking things because
at the end of the day, we live in the scheduling industry. It's an industry where like nothing is
allowed to break. Really, nothing is allowed to break. Oh man, if if we messed up something before
you just like push a bad code change to production, that results in like sales calls not being
booked. That means in revenue getting lost for for some of our customers. Like if we're down for
like 15 minutes, like the revenue that that loses them is like crazy. And of course, we catch the
heat for that. There have been some like chilling moments where um where we've messed something up,
the customer's shouting at us and uh and we really learned something and and those were like really
good early points of learning that just led us to um to really like reshape our engineering culture,
DevOps, and sort of like

so not not ship as fast like to break it.

Trying to understand the

check things a little bit more before you you're build those like mature engineering processes.

Makes sense.

I wanted to ask you a question on running a remote team because I was looking at your website and
it's very pretty. I think you used a tool for like visualizing all these I forgot the name of the

metabase. Metabase. Yeah. And um how many countries are your team located right now?

Uh good question. It's got like 10 plus

I'd say. Yeah. like 12:13 something like that

12:13 so I have been I mean I read your enter about section I like some interesting points that you
are running an open startup uh I first heard about open startup actually from buffer originally then
I have been also a big fan of Peter levels of nomad list I have been myself a nomad for a long time
I have been a full-scale digital nomad from covid I stayed three months in 21 countries So each
country for 3 months.

That's crazy.

So I'm a very pro-digital nomad person. And when I was like, oh this is a this is also becoming like
a very big digital nomad supporting company. Um how do you run a remote team which is so globally
distributed but still keep them aligned in the vision because this is something I struggled a lot
with like how do you do that? It's always a struggle. Um, you know, being remote is has its
benefits, but it also has its drawbacks. And for us, you know, one of the drawbacks is is is keeping
people motivated, keeping people aligned, and also like connecting them with with other team members
and things like that. You know, it's it's so easy to get to know someone face to face in person, but
it's not, you know, across Slack. And the thing is, as well, because we're in so many different uh
time zones, we're asynchronous as well. Um, so not only are we not face to face, but we also have
very little Zoom calls. There are only just tiny little handfuls of people that like actually get on
calls with each other during the week. There are people, oh, I had a call with somebody two weeks
ago. Uh, he's been with us for over a year and we're like, "Oh, wow. This is our first time on a
call. Oh, like nice to meet you." Um, it's crazy. But yeah, I think um just really like sharing all
of the updates that you can. you you can never overshare really uh as a founder. Make sure as well
like the stuff you're putting out internally, externally like these guys read my like Twitter posts
and things like that where I talk about like the visionforcow.com. Um they see the the interviews
and the conference talks and things like that. You know, just like anything, you can kind of be
inspired by anyone and really you should aim to inspire um your team and just kind of like your your
values will then become their values. They have equity. They are part of something. Show them show
them what that is.

Yeah. I think you're very active online on like sharing your thoughts and your team is also seeing
the thoughts. So like that's a good good way. I wanted to know the impact of AI right now in Cal
especially on the team side because when you started in 2021 it wasn't as crazy in terms of the AI
innovation happening I mean previously people were just growing their teammates do you think that
you will reduce the number of employees eventually or how are you tackling this whole AI shift
happening in the workforce

the good thing is we don't have to reduce employees and we actually told everybody that um always a
good thing to kind of like put a statement out and just be like, "Yeah, we're not like firing
anybody to replace them with an AI engineer." I believe in making people 10x engineers or whatever
it is that they do um using AI. Like I can do so much more as a founder because of AI. Um you know,
like I can do like legal work or finance work and things like that which I'd never previously be
able to do because of AI. We implement the same thing across the team. We just have people that are
really really good and we tell them we kind of made it a policy like you should be you should be
making the most out of AI tools like you should be as much of a 10 or 20x engineer as possible by
you know give uh give like Devon or some kind of like AI software engineer any of the small tasks
you don't want to do at the same time then jump into cursor or wind surf or something like that and
then start working on this if you're in uh like our growth team or something like that. Uh, you
know, use AI to like automate content production and things like that. You can, um, you know, like
all the blog posts and things like that. Um, you can get all of like the ideas and the outlines and
all the research, these things with AI. Let's build all of these like automated workflows to make us
do a lot with the little people to an even greater degree than what we were even able to do before.
I wanted to actually know also Bailey on the like you as a founder do you know the three age the
hacker hustler and hipster framework that you can either be a hacker who is building things hipster
who is the designer and hustler who is a better salesperson

usually this three combination is the most ruthless combination in the founding team what are you as
a person are you a designer builder or salesperson or all three.

I'd like to say I can at least somewhat do all three, although some of them not so well. You know, I
think like I'll tackle design first. I'm not so good at, you know, like I don't think I'd be
designing, you know, like the the cow.com UI by myself, but I think there's a there's a good thing
if if you really have an eye for design and an eye for like nicel looking products, uh, especially
UX and things like that, that's going to really help as as a founder. I think that's probably even a
fundamental thing as long as like as long as you know what's good and what's not. You like sometimes
I push back to the design team and I'm like, "Hey, look, I don't really like what we've done here."
And sometimes I will make like terrible mock-ups in Figma um or something like that. You know, I'm
not I'm not a designer. I don't know how to use like auto layout and all the crazy stuff in Figma.
But, you know, like I'll try and put something together which explains my vision and then like
they'll just refine it. Of course, hacker. I think that always remains true for both me and my co-
founder. Neither of us are exactly best-in-class software engineers, but um we absolutely get our
hands dirty. All the quick fixes and things like that. Sometimes it's just so efficient just to like
just open it up and fix it yourself. Like by the time I like find the right engineer to do it and
then send them a message and then all that, you know, like I may as well just get it done quick. But
uh you can also kind of apply that to all the other aspects of business. talking about we we
automate a lot of things. We look at a problem and we're like, "Okay, how do we do this?" We have a
ton of people who apply for our like internships. So, the thing I'm building right now is I'm coding
like an AI um application thing where it will go onto your GitHub profile, look at your open source
contributions to cow.com and it will like use AI to like uh review the quality of the code and like
rank these people to see like do you meet the threshold uh to like get the internship or something
like that. Um, I think you should just always be automating. And then I think first and foremost, I
think I'm more of a hustler than anything. Um, maybe not necessarily in sales, although I'm pretty
okay at it, but I just think in terms of like being the guy that like gets things done that like
that works with just works with everybody. Um, you know, like I'll go around the city to to existing
customers offices or, you know, to new customers, shake some hands, get some stuff done. I would say
that's like my favorite part about being a founder.

Yeah, you are basically a very interesting combination of like almost a balance of all three
characters a little bit mashed up. so excited to follow like what happens uh to you as a as a
founder as you become more mature. I wanted to know a little bit about your processes as a founder.
So for example, I like a little bit different process in a week or a day. What you think you do
daily or weekly which is very different as a founder. For example, I'll give an example. I love
journaling like physical nondevice journaling. like I would be so chaotic if I didn't have a writing
device. How do you start your Monday or what is your process?

I I live a pretty like chaotic lifestyle. Um you know I'm jealous of people like you who have their
who have their routines set out and you you know that you you journal every day and have you know
consistency. Yeah. I'm always like I'm always just kind of like at working at different times and um
and doing different things each week or I always plan things at the last minute as well. So uh
whenever I have that like small talk with co-workers and like what are you doing this week and I'm
like I don't know. Um like I'll probably like find out by Friday night what I'm doing Saturday
morning or something. Yeah. I don't really follow too much

structure in life.

You follow the going with the flow water.

Yeah. And that's that's kind of like part of who I am. You know, some people have to like plan
things to go out. Whereas like me and my dad, if we would go somewhere, it would it would be like
Sunday afternoon. We're like, "hm, it's 400 p.m. Do you want to just like drive a couple of hours,
go here, we'll just do whatever. We'll like find something cool that." And I think that that really
God that really influenced how I am as a person.

Yeah. Just just vibing. Just vibing. Just vibing. Um in the last four years do you think that you
had to evolve in some places as a founder uh like because whenever we start we are a little im like
new right and then over time we have to learn some new skills what do you think that you learned in
the last four years as a individual founder like on your own character set that you didn't have much
but you grew into it a little bit

I have changed entirely as a person both in the business and the personal context since being a
founder. It it really changed who I am. I can't even begin to describe just how entirely different
of a person I was. I always grew up relatively like introverted. I was always a bit of a more of a
shy one. You know, I was always uh when it was a Christmas play in school, I'd be the one like back
there in the corner because I never wanted a part. I didn't want anybody to like see me on stage,
you know. Now I'm like I'll go to like a conference and like speak in front of a bunch of people and
things like that. But no, I think it also just changed like a lot of being a founder is just you've
got to be confident. You've got to radiate a certain thing and like number one is that going to
command respect with um you know people that you're selling to with your employees. Like you pay
their wages you know like their their family eats on the money that you give them. they they want to
feel like the person who's at the helm is like is like truly in control and is like confident about
that. So you know for for just everything investors as well um you know how do you just make
investors entirely believe in your company believe in you a lot of it is like is just confidence
charisma you know just learning new ways to work with people yeah I suppose there are there are
skills that you develop I never knew how to do sales I never knew how to do um finance or legal
stuff or compliance. So, you know, like in terms of actual real world skills of what I do in my day
job, I knew none of it before. Being a founder is so different day one than it is to like day 900, a
thousand something like that. Gone of the days where I could just build for fun.

Yeah. I love that you basically are almost like building this company almost helped you coming out
of the shell like you are like it's it has given you so much new skill in terms of confidence
charisma

being outspoken and if you didn't build it you wouldn't you'd be like kind of like in this shell

I I suppose so um yeah I think it was actually a few years leading up to when I started cow.com that
I did like I I slowly started to become a bit more extroverted but like

I I think once you get thrown into the being a founder is being thrown into new situations. Yes. And
yeah, I was like thrown into like I now need to talk to investors and so you kind of like you fake
it till you make it like you you puff up the chest and you like put on the confidence and then over
time that just kind of becomes your personality. Um

the same thing I'm doing with the podcast like

Exactly.

Yeah.

Um Exactly. We're all We're all just out here, you know, trying to be the most confident version of
ourselves. Yeah. Um and yeah, I mean eventually that really changes your personality.

Definitely. I agree. U I was so scared before the episode today. I was like, "Oh my god, my first
episode ever." I think for me like I changed a lot on so previously I was I mean I have an
engineering background and I was primarily a builder persona but I think in the last four years I
had to see that how do I empower my team to almost like self-manage themsel without needing me for
every small decision because like I'm really never fully free on the strategy until I have to be
very busy on the day-to-day operations. So that I had to grow a lot because I was so bad in managing
people. I'm sure you you also probably grown. I maybe you are already

No, no, definitely. Um there are there are always like learnings and good and bad experiences and
things like that.

I I love your anti-OMO approach to life. Like that's that's basically what I'll take from today. I
wanted to thank you Bailey for you know like being in our first podcast.

Um

of course it's pleasure.

Yeah. and wanted to give you something a gift. I want you to open and see basically what is inside.

Yeah. So if you can like Yeah. So this is actually a this is a bottle which says for immigrants by
immigrants.

Oh nice.

Yeah. You can open it if you want to.

And it has a temperature display.

It has a temperature display. Who

that's crazy.

Yeah.

Oh, I love this.

Yeah. for immigrants by immigrants

from me to you.

That's crazy.

And this is actually like a silly

almost silly pun of giving you a physical calendar.

This is uh

this is cal.com. We looked in Amazon like can we find something which looks like cal.com in terms of
font simplicity.

You know what's crazy? Most most day I don't even know what the day is. I'm like

there we go. This is

like I genuinely do not know what day of the week it is right now or what like number day we're on.
Like I would have to look at my watch for that.

This is your like

I can't look you in the eye and tell you what day of the week it is right now.

This is your physicalc.com. Thank you.

So So now when I have such little sleep and you know like right now I I wake up and I'm like what
day is it today?

Yeah. There we go. Thanks.

Amazing. Thank you so much. It's been a pleasure. Yeah.