The Pomp Podcast - #1273 Bailey Pumfleet | This 19-Year Old Raised $25 Million To Build A New Calendar

Starting point is 00:00:00 What's up everyone? This is Anthony Pompliano. Many of you know me as Pomp. You're listening to the Pomp Podcast, which is my effort to find the most interesting people in the world and sit with them for hours while I ask questions in an effort to learn. So it would mean the world to me if you would subscribe to the show on your favorite audio platform, watch episodes on YouTube, and tell your friends and family about the podcast. My goal is to help millions learn from the world's most interesting people. So let's get into today's episode. Today's episode is with Bailey Pumfleet. He is the co-founder and co-CEO of Cal.com. Cal.com is taking open source calendar management to a whole nother level. I really enjoyed this

Starting point is 00:00:42 conversation because it's all about how exactly do people manage their calendars, what you can do to become more efficient, how Cal.com is taking what they learn with some people and bringing it to the masses. This is a business that I've been excited about for a long time. I and many other people across the tech industry are investors in Cal.com and they continue to surprise me every single time they send out their updates showing just how many people want a better calendar right now. Here is my conversation with Bailey Pomfley. Anthony Pompliano runs Pomp Investments. All views of him and the guests on his podcast are solely their opinions and do not reflect the opinions of Pomp Investments. You should not treat any opinion expressed by Pomp or his guests as a

Starting point is 00:01:26 specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his personal opinion. This podcast is for informational purposes only. Today's episode is brought to you by Trust and Will. I've gone through a number of different changes in my life over the last few years. I got married, I had a kid, and I had to start thinking about how could I ensure that my wife and my child would be okay if anything ever happened to me. That's where trust, wills, and estate planning come into play. Now, most people, what they do is they get introduced to a friend, an uncle, or someone in their local community. It tends to be someone who's really expensive, a lawyer, an accountant, or somebody who does

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Starting point is 00:03:57 Bailey, calendars. Everyone hates them, but everybody got them. What are the major problems that you guys see with scheduling and kind of the calendar products that have been out on the market that made you guys want to go buildcal.com? Yeah, I mean, we're definitely far from being the first guys on the market

Starting point is 00:04:12 when it comes to calendar scheduling. But the problem is it's great if you fit into their niche small use case, but let's be real, we're people with busy schedules, all sorts of different workload and scheduling requirements, which usually leads a lot of people to requiring having some sort of EA that schedules their stuff. And the problem is nothing else just goes far enough to achieve what we want because our time is complex and we need a way to be able to manage that effectively. And, you know, as users of many different scheduling products on the market that existed prior to cow.com, none of the others just do enough. And we realize that cow.com really is the direct solution to our own problems and the problems that our community face with scheduling all the time.

Starting point is 00:05:05 Now, when you think of the use cases that fall outside of those normal products that people had been using previously, Like what's an example of something that didn't really fit into that use case? Yeah, I think a good example is anybody who's busy because the calendar is great because it just throws everything into your calendar. But when you actually want to start putting a scheduling link out there publicly and not just letting anybody book you, like your time is important, protect it, ask people those upfront questions and then decide whether you want to have a booking with them or not or have better control about like limits to how many meetings you want to preserve your workload obviously we wouldn't be doing a good job as as you know founders or

Starting point is 00:05:52 business people if you're just taking calls 24 hours a day um so you want to be able to craft a good work-life balance and i think as well a lot of other scheduling products don't go anywhere near as far in terms of like privacy and compliance so you know a lot of people who use cal.com um vcs pe funds things like that now you're booking meetings with companies that you're looking to invest in now imagine the ramifications if that data got leaked because you know your calendar is a direct insight into everything that you're doing and there are absolutely no guarantees with pretty much any other product out there but they cannot read or sell your calendar data i mean we have to have access to read your calendar data and cow.com because it's open source because you can

Starting point is 00:06:42 literally go through and audit that code and make sure that it's not doing anything dodgy like cow.com absolutely flies past anything else in terms of security and compliance which means you know we work with people in you know finance um you know banking healthcare healthcare is a huge thing for us um even government organizations and things like that um there's there's really just a multitude of assurances that you get with cow.com in terms of longevity privacy compliance and these things are huge blockers now obviously cow.com is uh i would consider the leading open source solution for uh for uh kind of scheduling platforms what is the benefits of being open source versus maybe more of a closed source type solution yeah so i think it's it's always been

Starting point is 00:07:33 very it's very much part of who we are so not just on that privacy side because everybody could audit the code but also the fact that everybody gets an opportunity to to collaborate in the development of cow.com i think when people ask you know why is cow.com better than you know calendly or savvy cow or any of the others you know i could sit there all day and tell you every single feature we have but i think the more interesting thing to talk about is because we're open source since day one we've always been very close with the community because open source is not just about one company but a whole community coming together to build something and we have listened to the unique needs of every single person in the community and either we've built it because

Starting point is 00:08:17 we're listening to their needs or they're building it and contributing it via open source and so we've been able to build so much more of a comprehensive platform that has you know talk about integrations and things like that everybody needs things to to communicate with each other and we are the only scheduling platform out there that has this completely open app store um which allows you to build apps on top of your time build integrations with your favorite services i actually spoke with the founder of a video conferencing company a few weeks ago in sf And he told me that with Calendly, it was like a minimum of two years for them to build an integration with his video conferencing platform. With Cal.com, he was able to do that in not even a day's work.

Starting point is 00:09:02 That's the power of open source. Now, when you see Cal.com's current feature set, it seems like people from across industries are all starting to use it. What metrics can you share in terms of growth, adoption, kind of the number of meetings? meetings? What are the things that you guys are measuring to see, hey, this is working? Yeah. So with 10x our monthly active users in the past year, we've doubled total signups since March this year. We actually ran some very interesting queries and found out that for every one user that's using cow.com, because they're going and sharing their cow.com link, people love the product one user is bringing in 25 new users on average um we've also um

Starting point is 00:09:50 6x user growth um in the last 12 months obviously this is coming from our complete sort of bottom up funnel we've got tons of users that are either new to scheduling have never used any scheduling technology before we've got thousands upon thousands of users every week that are switching over from Calendly and things like that, because objectively, we do have a far superior feature set. And all the way up to enterprises, the biggest Fortune 500s or governments, healthcare, all these kinds of things, they're absolutely swarming our sales teams. So Cal.com is very much something of an unexpected, hype-driven growth.

Starting point is 00:10:32 So when you start to actually understand these users, you see the growth that's happening, how are you finding the company? What have you guys raised? Where are those investors coming from? Talk a little bit about kind of actually building the business itself. Yeah, I mean, so Cal.com actually started from very sort of humble beginnings because it was literally just a project that I worked on for some fun alongside my full-time job at the time.

Starting point is 00:11:00 You know, this was about three weeks of development, and then we launched it on Product Hub. And from the day we launched on Product Hub, you know, We got products of the day, products of the week, products of the month, all these kinds of things. People were signing up in the thousands and the tens of thousands. It all came in a pretty quick rush. And obviously, as soon as you start disrupting the market like that, that's when VCs reach out. So, you know, from the time that we launched our very basic MVP, VCs were in our inbox.

Starting point is 00:11:31 We were, you know, negotiating with VCs, things like that. um i mean at the time i had like 600 to my name i was like 17 years old when i started this you know we we come literally from nothing in terms of funding but like very shortly after we raised a 7.4 million seed round um built the initial team you know actually had some good money to go behind this obviously me and my co-founder both quit our full-time jobs at the time uh and then jumped straight onto this and obviously that money really sort of kicked us off the ground and then you know as we then got closer towards the time when we actually rebranded to cow.com because it was originally called colenso you can't get domains this good from the from the get-go

Starting point is 00:12:16 um that's when we raised our series a which was uh 25 million series a back and all of this comes from an absolutely incredible um cap table of investors and supporters how did you guys meet as co-founders interestingly we kind of bumped into each other on an email chain um we were both always looking for the exact same thing because back in the day if you went out there and searched like open source alternative to calendly things like that we actually when we recount this story both of us we we found ourselves on the same reddit threads and things like that you know just scouring google for the very solution to our problems and um here my co-founder he had like an initial idea um

Starting point is 00:13:04 but his company at the time got acquired by on deck and he went into a big head of products role there and so he wouldn't have had time to work on it so he reached out to other people who were interested in this early supporters things like that i was like one of the first five people that ever sort of reached out regarding the idea. And then we sort of struck up an agreement to actually co-found this company. And obviously with the growth that it saw, we then quickly quit our respective full-time jobs

Starting point is 00:13:37 and just really went into this head on. Now, when you see two co-founders that get along, kind of bumped into each other in the way you're describing, raise a lot of money, have these metrics, where are you going right it's kind of you got all the ingredients but you still gotta still gotta produce the plate right you still gotta actually get the meal put together what is this vision over the next call it you know five to ten years that you guys think uh can take what i think most people would look at be like hey i need a calendar that works for me i need a scheduling

Starting point is 00:14:06 platform that works for me but how big can this get what does that look like well it looks like world domination in a sense so you know the thing is is i think that it's you know thank you to Calendly they paved the way back in you know sort of the the 2010s ish um and were the first people out of the door with with scheduling products and made it the new thing where you can send a link to book a meeting but the point is is you know I still have to pick up the phone at 8am just to you know call my doctor and make an appointment like they're not aware of scheduling links and things like that the point is is our long-term goal is to get this out to everyone you know we We have a great product, but we need to put in a ton of effort into making sure that, you know,

Starting point is 00:14:54 not just people who typically are aware of calendar scheduling products, you know, founders or people in tech. Obviously, within that kind of niche, we perform really well. But I personally want to see that Cal.com gets the impact that nobody in the world has to, like, pick up the phone to take appointments. like look at small businesses and things like that where they are literally you know they're doing their work and then they have to get distracted from their work to then go and pick up the phone and take appointments it's like why is that not solved by cow.com already um so it's just achieving mass mass adoption from the bottom up you know these start as maybe individual users or small businesses but then it works all the way up into i mean we already have like a few

Starting point is 00:15:42 governments that are using cow.com to power their scheduling it's making the lives of their citizens you know so much easier the question is why is not every government using it or every public service and things like that i think that's something that me and my co-founder really care about is we measure directly like what impacts do we have on the world how many times do we see other people using and benefiting from you know better scheduling technology now as i think about this technology open source is really interesting to me because you're a company you're being funded uh you then are soliciting other people to continue to improve it the product value accrual is something that a lot of people talk about in the bitcoin and crypto world here is pretty

Starting point is 00:16:29 interesting right like on one hand there's a business that is accruing value and continues to grow but there's also the open source software so how do you guys think about like open source and then like for-profit you know kind of centralized company and why is this the best model right like a lot of people in your situation would just be like you know let's build closed source technology i understand why the open source could be valuable to the user why is it valuable for you all as business owners and kind of founders building this company yeah it's a great question because i mean there's always a very delicate balance between between those things and you know in your question you said why is it the best model it's probably not even the best model for

Starting point is 00:17:06 everybody but what open source is is something that has always been you know very core to cow.com from its inception and uh you know will always be so what we see here is obviously we're here to make impacts on the world and so there's things out there like refugee camps are using cow.com free of charge through open source to you know schedule schedule services for their refugees and that's huge to us um you know there are like the reason why that some of these governments from a bottom-up side can actually even use cow.com is because fundamentally it's open source that's not possible with anything else out there so we're always here we want to give something back to to the world like we genuinely believe that scheduling is so core to what everybody does

Starting point is 00:17:57 i mean everybody has a schedule everybody um you know needs to needs to meet with others and so we see it as you know we give something back to the world open source contributors give something to us um but we can still charge you know the businesses and things like that that use cow.com and turn a profit it's not none of this with open source it's not a business strategy it's not um you know it's not a commercial reasoning behind it it's more of a we're just genuinely interested in creating genuine positive change in the world but behind a for-profit company. Now, I always look at the funding environment and I see, okay, you guys were able to raise a ton of money previously. Now, not so hot, right? In terms of the funding environment,

Starting point is 00:18:50 but the business still continues to do really well. And so what have you guys seen, not just from the investor side, but from the user side, as the market's gone up, the market's gone down, scheduling doesn't go away. So how are market conditions kind of play out with the product itself? Yeah, it's always interesting because, I mean, you know, although cow.com has always been very focused on longevity and things like that. So fundraising has never been something that's, you know, too critical for us. Obviously, there is still immense growth and things like that. We've always got investors in our inboxes and things like that having calls to us.

Starting point is 00:19:25 You know, if you want to raise your next round, we'll be here. I think a lot of them are real believers in where we stand to grow into. um and like i say once we really get sort of that mass adoption and things like that this is this is supposed to be a huge business not just in terms of um you know the dollar figure but also in terms of the the real world impact to the amount of users it has in the world also we see so part of what cow.com does as well is what we call like scheduling infrastructure so long story short nobody wants to actually build scheduling into your own product if you're out there building telehealth if you're out there building a hiring marketplace you know ask ask

Starting point is 00:20:10 any head of engineering or something like that they're going to tell you it's a terrible idea to build that yourself so part of what we do is almost like stripes for time you know we provide a ready-made developer kit um and which handles all the scheduling for you and you just focus on building your product so we see a lot of companies that come up and they're building their entire company on top of cow.com obviously they go around they're raising in sort of like the seed markets or series a's and things like that and obviously it's a very attractive thing for them to be able to put 100 of their time and effort into their core product and do what you know makes them different from everything else rather than wasting years and millions of dollars on on scheduling so

Starting point is 00:20:54 So I think in a way we've sort of helped empower some people to fundraise as well as, you know, having raised two really great rounds ourselves. What's been the biggest surprise in building the company so far? How quickly it all takes off, you know, and I seriously mean this back in the day with the MVP and things like that. this was just a project um not something that we ever said you know this is going to be a five billion dollar business in 20 years or something like that this was literally creating the direct solution to our problems because me and my co-founders are both builders at heart you know we see a problem and we we build the solution to it and it was then on that launch day and then just like going about my day and i'm like damn this this really could be something and then

Starting point is 00:21:44 you know over even the subsequent weeks we had um not just the investors in our inbox but the like even fortune 500s uh within our inbox within weeks and we we suddenly realized the impacts that we can have like i say the stuff to do with government health care refugee camps all these it's all very very close to our hearts we're always um you know very very moved by some sort like the positive impacts that can that can happen with cow.com and we'll always try and be committed to to supporting like scheduling for good causes and things like that um so yeah i think it's all just being sort of a delightful surprise in in how how much impact and how quickly something can take off when you think about um the scheduling market in general are there things that tangentially

Starting point is 00:22:37 you can expand into once you kind of have somebody's calendar? And I think of like the fintech industry, you know, if you get deposits, all of a sudden there's plenty of ways to build other features or money. How do you guys think about that for scheduling? It's huge. It's absolutely huge. So on a few things, you know, when I mentioned we have our app store earlier, the whole idea of that being able to build apps on top of your time, huge. And the thing is, is Cal.com is the one that's uniquely positioned to do this

Starting point is 00:23:03 because we're open source and very privacy friendly. you know that if we're going to be the central thing that's like using your calendar data to to do all of these useful things you want to make sure um that we are obviously respecting your privacy so we have all sorts of cool apps i mean one app that we launched recently is calder ai um which uses ai in the typical sense of like an assistant where if somebody emails you hey can we find the time to meet you can just forward it to your username at cal.ai so bailey at cal.ai and i say put this on my calendar for next wednesday and you know it will use ai that will then talk with all of the the core um cal.com logic because obviously we've built all of that

Starting point is 00:23:48 core logic and things like that so front end apps can just change the way that you interface with this rather than having to you know really write the book from scratch um and so we're able to ship like a great ai experience that people are loving and you know finding new ways to to schedule things um we work with a lot of external companies um they can you know safely use your calendar data to you know do all sorts of productivity um productivity hacks little apps things like that we have a we have an app wipe my cow you can just hit one big red button and reschedule your entire day of meetings if an emergency comes up like it's it's amazing to us that we're in such a core position to to what people do with their calendars that we can then become sort of like

Starting point is 00:24:35 the central hub for anything that interacts with your time and we have a lot of ambitious plans uh into the future as to how we're going to expand um all of our marketplace do things like if you want to list your availability on a different site, say you join an expert's marketplace or something like that, rather than filling in your availability there, that there'll be like a sign in with cow.com button and that can then pull your availability straight from cow.com, things like that. That's a lot of the real long-term stuff that we can build. Talk a little bit about some of the trends that you all see in people using the product. product is, I don't know, more successful people have busier schedules or less schedules.

Starting point is 00:25:20 Do you have any kind of trend analysis from some of the stuff that you guys see with calendar habits? Yeah. I think we see an interesting thing because of all of the advanced options and things like that that Cal.com gives you to restrict the amount of bookings you have, to not be doing more than X amount of meetings a day. always hear a lot of feedback from some of the highest profile people that like don't want to be blocking up their schedules with many things i know a lot of people have different opinions

Starting point is 00:25:53 as to how many meetings you want to have and things like that but especially for for like high profile people they always comment about like it's great i can now lock down the amount of uh events that i'm that i'm having booked into my calendar i can free up a lot of time i'm not taking anywhere near as many you know useless meetings things like that um and i think especially for positions like sales or if you're a founder things like that you want to vet who's coming through to you and with cow.com we have so many amazing subproducts and features and apps and things like that that can just help you take less meetings which is very ironic considering that We're a scheduling platform, and we want you to have as little meetings as possible.

Starting point is 00:26:42 But it's all just there to protect your time. And I think that that's definitely one of the things which I find remarkable in the irony of it, that we help busy people be less busy, I guess. Another part of this that seems pretty interesting to me is the maker versus kind of manager schedule, right? Paul Graham is famous for talking about. In that, to some degree, maybe you want your managers to have as many meetings as possible. You want your makers to have as few meetings as possible. I see people talking about artificial intelligence and like they might be able to write emails for you. They could do, you know, all these like different tasks, whatever.

Starting point is 00:27:18 Is there a world where we anticipate like AI agents meeting with AI agents? Or like, you know, like how do you kind of see artificial intelligence playing into some of this stuff? And how much of it is like hype for actual things that could be built here? Quite. I could see it being a possibility. I mean, the good thing is, as well as with Cal.com, we move fast and not just I mean, we've shipped a lot in in a small period of time with a small team, but also we're always sort of on the forefront of what's new.

Starting point is 00:27:51 You know, we shipped our AI like our Calder AI. we've shipped a number of things to do with web3 and crypto whereas like nobody else is doing that um a lot of other competitors aren't even shipping regular features let alone um some of these new things that i mean like nobody is really accepting crypto payments or allowing you to confirm you know membership within a dow or something like that um we're doing that you know we're not we're not playing it too edgy we're still you know a very rock solid and stable company but just through open source those who are passionate about some of these new things have the ability to build this on top of cow.com um so i think that we're always testing the waters and and trying to be at the

Starting point is 00:28:39 forefront of technology and you know for now that's about sort of one-sided ai um in the sense of like making it a lot more natural to to interact with your calendar e.g almost having like an ai version of an assistant that can put things on your calendar and know your schedule but i think that once the technology really expands to be able to do like fully automate the booking process between two people and you know an ai to really understand that uh i can always promise you whatever the technological advancements that are going on we're the first people in the door. Now, my last question for you is when you all are successful, and I say that as an investor who is financially incentivized to

Starting point is 00:29:27 see you be highly, highly successful, what do you see as the ramifications to the market? Is there one scheduling platform to rule them all? Everyone else dies. Is there still a couple different options for different people and how does maybe work change if you all end up being the dominant platform yeah that's um i mean to be fair we aim to be the one that rules them all and i'm not just saying that as your typical over aspirational founder you know without basis see the thing is is we've kind of flipped the script here it's taking us longer to get started and things like that because we're trying to build such a huge and complex product but the thing is is in the long run where we i mean already we can handle every use case there is out there

Starting point is 00:30:18 um no matter what products you're using we handle like even some of the more specialized ones that do certain things in terms of like um routing sales calls to the right seniority of sales person depending on the size of the deal like we've done that um i always find myself in conversations with people who are like oh we've tried every scheduling tool out there it doesn't do exactly what we want it to and i'm like try me and they tell me what it is and i'm like yeah cow.com can do that so we've really put a lot of time and effort into making something uh can really handle like every use case that you can possibly throw at us um and i think that in the the long run that will make us become quite a dominant platform because in reality there is no

Starting point is 00:31:06 reason to actually use anything else if cow.com is going to do everything under one roof and that's why i think the side of us about being open source and things like that is very important because you know if we're going to sort of monopolize the market you want to make sure that we're doing that in good faith um you know the as well this this isn't cow.com isn't something that we can just like it can disappear one day and the monopoly we've built falls is because it's open source it lives on forever um i think there's there's a certain power in that so yeah we're always aiming to be the ones to to just solve everybody's use case i think we already do that um and it's now just a question of getting everybody across all those different use cases

Starting point is 00:31:54 using cal.com because once they do they can't stop telling us and telling twitter how great the switch has been where can we send people to find you on the internet and find out more about cal.com cal.com uh we have like a ton of resources on our site we have information for every use case and we have a great domain that you know you can just type straight into your url bar after you me say it once so check out the website whatever um whatever industry you're in we have we have use cases suited for you we have features suited for you um and if it doesn't do whatever your whatever it is my email is bailey at cow.com ask me whatever it is that cow.com doesn't cover and i guarantee we will have it or if we don't have it we will build it awesome bailey thank you so

Starting point is 00:32:44 much for joining us we'll definitely do it again in the future thank you very much

The Pomp Podcast - #1273 Bailey Pumfleet | This 19-Year Old Raised $25 Million To Build A New Calendar

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