March 8, 2023

#106 Dotcal: The Calendar Wars

#106 Dotcal: The Calendar Wars

There are tons of companies popping up in the scheduling space now that Calendly is valued at 6 billion dollars. Everyone wants to build the next billion dollar calendar app, including David Matthews, founder of Dotcal. He thinks he’s created a scheduling platform that will take over the space. But will the investors place their bets in Dotcal or is the scheduling race already overbooked? 

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Jillian: the 5th pitch! [clap]

There is nothing more universal than a calendar. Everyone's got one, and let’s be real, they kind of run our lives. Not just all those meetings, but all those emails back and forth, trying to find a time that works for everyone.

There’s already been a massive business built off making scheduling easier: Calendly. They're valued at over $6 Billion dollars. 

Today's founder Dave thinks there's room for another, with his new calendar solution Dotcal. But there are other startup founders who think the same.

The Calendar Wars are just heating up. And the investors want in. But is scheduling software already overbooked?

I’m Josh Muccio, welcome to The Pitch. Where real entrepreneurs pitch real investors for real money. 


Neal Sales Griffin: I’m Neal Sales Griffin, Managing Director here at Techstars Chicago, and I’m happy to welcome y’all to my city

Elizabeth Yin: I’m Elizabeth Yin, and I’m a General Partner at Hustle Fund

Phil Nadel: I’m Phil Nadel, I’m the Managing Director of Forefront Venture Partners

Jillian Manus: I’m Jillian Manus, Managing Partner of Structure Capital

Charles Hudson: I’m Charles Hudson, Managing Partner, Precursor Ventures

The pitch for Dotcal is coming up after this.


The information provided on this show is not intended to be investment advice and should not be relied upon as such. The investors on today’s episode are providing their opinions based on their own assessment of the business presented. Those opinions should not be considered professional investment advice.

David: hello, David

Charles: Hey David, Charles, nice to meet you.

Elizabeth: Hey David, Elizabeth.

Dave: Hey Elizabeth, nice to meet you.

Phil: Hi David, I'm Phil.

Dave: Phil. Nice to meet you.

Jillian: Hey David, I'm Phil too.

Dave: You're Phil too?

Jillian: Yeah. Together we're Phillian. I can also be called Jillian.

Dave: Nice to meet you, Jillian.

Jillian: Nice to meet you.

Neal: Hey David. Neal.

Dave: Nice to meet you, Neal.

Neal: Good to see you, man.

Dave: All right. So let's do this.

Jillian: Yeah.

Dave: Okay. So hello. My name is David Matthews, I'm the CEO and co-founder of Dotcal, and we're building the world's most human interface for scheduling. A few years ago, my cofounders and I were traveling the world as digital nomads while running an agency with dozens of clients around the globe. As you can imagine, scheduling across multiple time zones with a million back and forth emails was an absolute nightmare. To make matters worse, even the best scheduling tools in the market consisted of boring white pages that hurt our brand at the most pivotal conversion point for our business, that of booking a meeting. So we built Dotcal. Dotcal's the first scheduling platform that allows users the ability to create customized booking pages that perfectly match their brand while also providing a more delightful way to find time. We're addressing the billion knowledge workers and businesses worldwide that schedule meetings each and every day. Since opening up our beta three months ago, Dotcal users have created over 8000 booking pages and are scheduling over 100 meetings a day, a number which is growing at a 45% month over month rate. We're raising 1 million dollars to fuel that growth and build a better booking experience for all.

Phil: David just tell us a little bit more about sort of how you think about the market, how you're differentiating from Calendly and some of the others that are out there?

Dave: Totally. So at the core of what we do is we try to make scheduling just more intuitive, more human, more natural. And when you're using a Calendly or you're booking a salon appointment or something, it's very like robotic and it's very inhuman and I take the opposite approach. I say, hey, actually, you create the experience you want for your brand so that it will probably increase conversions. So a lot of people think that we're just Calendly with pretty colors. The next phase of what we're building is a booking page builder which no one has done yet, and so you can create the experience from the ground up. And so to that end, we are very different than Calendly. Calendly just did a $10 million rebrand or whatever and they touched everything on their platform except for their booking pages. They have a philosophical perspective which is - it should be utilitarian. Everyone should look the same. And for me, coming from a marketing background, running a growth agency and building a lot of landing pages. And I was using Calendly and it just wasn't converting as well as it could have. And so that was, kind of gave us the genesis idea.

Phil: That's interesting insight. And it's something frankly I hadn't really thought of. Do you have any statistics about what the conversion rates are, like on Calendly? Because I would think that if two people say, yeah, let's schedule a meeting, and I send you a link to my Calendly, that the conversion rate -

Dave: It's pretty high. Because you want to schedule a meeting.

Phil: I would think. Like, you have two willing parties, right? So tell me, like what are the numbers on that?

Dave: Yeah. So we've run a lot of A/B tests with 10,000 pages at this point. And, and Dotcal conversions are about 25% higher than Calendly conversions for marketing purposes. But we already have enough -

Phil: But - so the 25% lift is in a marketing context?

Dave: It's in a marketing context. Yeah. And so the design and the booking experience and the call to action, which effectively is booking time, for some professions, in particular sales people, recruiters, that's actually very, very important, right. In fact, actually, the reason I'm here today is because we looked in our database one day and we saw this username Josh who had tons of bookings. And so we looked into it and that's how we found The Pitch show, right. And so Josh uses Dotcal for The Pitch show, and in fact actually he left - I think he tried Calendly and Vimcal and uses Dotcal, right. And so to answer your questions, yes, on one hand if you're just scheduling a meeting with me, it's gonna be 100% conversion rate. I think we're more akin to say a Squarespace. Squarespace has a templated approach and that templates allow them to verticalize into different spaces. If I'm a photographer, I have a photography template. And the carousel is useful to me as a photographer. If I am a non-profit, maybe I use the widget that takes more money in. So the templatization of this is actually like a pretty powerful part of our platform and it's something that will set us apart in a huge way from Calendly. 

Neal: You mentioned sales and recruiting. What's the early adopter use cases here?

Dave: So, so far we have about 50 industries on our platform. These are anyone from a sales team, actually like 25 people from Zoom. So a lot of sales people, a lot of visual people, wedding planners, a lot of photographers, a lot of those agencies, they're using us. Another really cool example that we've seen, a lot of emergent behavior we've seen, is with a feature we call our shared booking pages. If we wanted to follow up right now with all of us, like, say next week, how do we do so? We’d, I probably email your EAs, or your chiefs of staff, or you and have a million back and forth emails. But in one second, I can easily invite all of you to a shared page, you sign up for Dotcal in say 30 seconds, you attach your calendar, it pulls your availability. So now all of our availabilities are on one page.

Jillian: That's big.

Charles: Yeah. I think I actually have to be out due to a conflict. I'm an investor in a company called LetsMeet that does the group scheduling thing. But so I just wanted to flag that -

Dave: No worries. No worries.

Charles: I thought I should just…

Phil: So is that a similar function?

Charles: They sort of realized that group meetings on Calendly are difficult. They have the polls feature which is kind of okay, and they're like, no, look, what you really want is if in the end you get to a time where you found something that works, it'll automatically, hey, everyone has said that this time works. And obviously if you're all on the network, it can find the times for you. And it works actually quite well for the use case that you mentioned. But that's like their core use case, is like multi-person group meetings that are hard to do on Doodle, that are kind of a little clunky to do on Calendly. And to your point, they're like we're gonna optimize for that use case.

Neal: I just had that problem like yesterday. Can you solve it?

Dave: We can easily solve that right now with our shared functionality. But I don't think that's even the most interesting feature. So shared pages are useful for all of us getting on, you know, own page and sending it to Josh, he can book on all of our calendars. But what's really interesting is they're most useful for one-on-one interactions. So for instance, I have a shared page with my therapist. And the reason I do that is instead of calling a secretary and, you know, going back and forth, or instead of me actually sending my Dotcal, which then he has to see when he's free, I just say, hey look, let's just create a shared page with us, right. And so now, every time I book a therapy appointment I have this page that immediately books and only shows times we're both free. And so there's a lot of emergent behavior with the one-on-one scheduling.

Elizabeth: I really like some of the innovation that you're doing here and understand these use cases and see how they're very separate from the general booking link use case, but unfortunately I think we're probably going to be too close to this with Vimcal. 

Dave: Oh yeah. No worries. No worries.

Elizabeth: Thank you.

Elizabeth, like Charles, is already invested in a competitor to Dotcal. So unfortunately, as the locals say, she’s conflicted out.

Two investors in the room with direct competition could make it impossible for Dave to close the remaining investors. Or could that make Dotcal even more interesting? We’ll be back right after this.


Welcome back to the conflicted pitch. Elizabeth and Charles are already invested in dotcal’s competition. I wonder how that will affect the other investors in the room. Here’s Jillian: 

Jillian: So can you tell us a little bit more about your background? You sort of slid over the fact that you ran or built a marketing...And what about your team?

Dave: So I was a digital nomad before it was cool, before Covid.  I was traveling the world running a marketing agency, essentially acting as a fractional CMO for tons of companies around the world. My cofounder Rylan I met in Croatia, and our other cofounder John we met in Lima, Peru. Our team of engineers are six in Ukraine, and it's been a super interesting year, as you can imagine, with them.

Charles: Yeah.

Dave: But we love being a remote team.

Phil: So can you talk a little bit about your revenue model and how that works?

Dave: Yeah, exactly. So we're freemium, where if you want to use one booking page, you want to use a shared, you can use us for free forever. But if you have more than one booking page, then we start charging you. We charge $10 a month if you want to use more than one booking page. And we charge $15 a month for teams, per seat.

Neal: So are you primarily pulling people from these existing scheduling tools like Calendly? Or are they coming from other places?

Dave: Yeah. So our kind of initial go to market to test our hypothesis, was, do people even care about branded booking page? And so we built our platform and we initially targeted Calendly users. We just reached out to them and said, hey, we are Dotcal, we exist, do you care? And to that end, about 3000 people have already moved over from Calendly and actually Vimcal, sorry - right now..

Jillian: So what percentage of the 3000 are paid?

Dave: So 11% right now is paid from our free users right. So we have a little over 300 paid users and we have hundreds of active users. And that's growing. Booked meetings, there's about 100 meetings a day. That's growing about 45% month over month.

Jillian: Those 300 paid, what does that represent in revenue?

Dave: Yeah. We make about $5000 a month in revenue, because some of those users are team users. 

Phil: How are you acquiring customers now?

Dave: Mhm. So one is actually just reaching out to Calendly users at scale and just letting them know we exist. So that's kind of the first core way. The second one is through confirmation pages, so through booking pages. Once you do a booking, it says, do you want to sign up for Dotcal? And people are signing up. The third way is gonna be teams. So if we sell a team of 20, we now have 20 nodes, 20 people are using us, and they're getting more people on to that. And the most interesting way, and I think this is the way where we become really big, is through shared. In order to use shared, if you want to use it with one person, say my therapist, he comes in our ecosystem, he uses it for his other clients, these things kind of spread. If I brought everyone on to a shared page here, that's five people who are now using my platform, who now see Dotcal and can use us in other parts of their life. So that's the fourth way that we're going to spread, and I think in my opinion, we're going to look back in a few years and be like, oh, Dotcal became a billion dollar company because of shared.

Neal: So it looks like the water's getting a little red, right, in this space. Long term vision, like where do you see yourself amongst these other players.

Dave: I see us as like the anti-Calendly. I see us as the Apple to the Microsoft. Both of these players work, Microsoft works great, Apple works great. But whichever ecosystem you want is determined by who you are as a person. Our booking pages are very visual. They're very different. And to that end, we think that there's a huge market for people to choose to have more visual booking pages. We think in time, we can prove that Dotcal is actually better than these.

Neal: Yeah. I'm trying to gauge how big of a business you want to build. Like what's the motivation to go far? Because this seems like it could be a great, relatively, like small business. You could get it up to a certain point and then just run it.

Dave: Totally.

Neal: So outside capital, like, how are you planning to produce a return for yourself and for investors? What does that look like down the road?

Dave: Yeah. So first and foremost, my goal as a founder is to make our company anti-fragile. I think that's like the biggest thing. We need to not die. So I think about no matter what happens, if we raise from y'all, or don't raise any money at all, we're still going to survive. Fortunately, for this type of business, and for our lifestyles, we're super capital-efficient. Like we don't - we don't have a big team. But these platforms maybe take a little bit of time to grow, but when they grow, they grow in a big way, and they scale in a really, really big way. Our company is product-led growth by its nature, so when you send out a booking page, you're advertising for us. As long as we get the nodes out there, it will grow itself really big over time. Calendly took eight years and now worth $6 billion. But the truth be told, I've talked to thousands of people over the last year, and most people don't use scheduling tools. And in fact, most people never even heard of Calendly. I know that's super surprising to talk to a group of VCs about that, but that's the truth. And so to answer your question, we want to be very big. We want the nodes to spread, and they will given enough time. My goal to fundraise is to allow us enough breathing room to build the features we want to scale at the rate we want.

Jillian: So I'm just wondering, why wouldn't Calendly or any of the other ones add these booking pages. Where's the moat here?

Dave: People of course can have shared features and in fact we have one, but one thing they might not do is they might not go as visual as we are with the booking pages. This is another core differentiation. So again, I -

Jillian: Why wouldn't they? Why couldn't they?

Dave: They could but - if a company wanted to copy us, or they wanted to do that, they would have to lean is as heavily as we are and make it a core part of who they are. And will they do that? Sure, if we're successful enough, people will copy us. Everyone copies, right. So as long as we bring you in and we provide enough value for you, hopefully you'll stay and you'll be in our ecosystem for a long time.

Elizabeth: It's just a different form factor. Like Calendly's thing is working so why would they move away from their white pages that are working, right? It's like very efficient -

Jillian: Yeah. Yeah.

Elizabeth: - here are the times. It's just a different experience. It's kind of like you know Ford and Honda both exist, they both provide the same utility, but everyone has a different style of car.

Dave: Yeah and my take on the market is that we're in the very beginning stages. Because most people don't use these apps, there's room for multiple billion dollar companies in this space. I think it's like a corollary to esignatures and these grow in a way that esignatures grow. You send out a DocuSign and someone signs it and now you sign for DocuSign, you're using them for years, right.

Phil: That's a good analogy, yeah.

Dave: And so there's lots of - there's EchoSign that sold for a billion dollars and.. scheduling, I think, is even more interesting, because more people use scheduling, more people live on their calendars than actually sign documents, right.

Elizabeth: I think there'll be many unicorns in this space. In fact, years ago, I made an offer to Calendly, so I know a little bit about how it was back then, and people had asked about - what was that app called? Sunrise? But Sunrise was taken out of the market pretty quickly for - what was it? A couple hundred million bucks. There -

Dave: I think they're called Sunset now.


Dave: That was so bad.

Jillian: That was good.

Dave: It was so bad.


Elizabeth: Scheduling is just a critical part of people's lives and so I think there'll be a handful of big players and some will be bought out or, you know, Calendly's probably gonna IPO or be bought.

Charles: All these products work well with network effects. And there's not - like, you can't be a part of multiple networks. Like, having a Calendly doesn't mean that there's not value in having a Dotcal..

Elizabeth: Yep. And I actually still have a Calendly account, too.

Jillian: Did you mention how much you're raising?

Dave: So we're raising $1 million, and we've already raised $600,000, so we have 400k left of the round.

Jillian: And what was the valuation?

Dave: $15 million valuation.

Jillian: Post or pre?

Dave: Uh Post.

Phil: Who committed the 600,000? Is that an institutional investor? Or friends?

Jillian: Angels?

Dave: Yeah, institutional investors. Corporate VC and some angels.

Phil: It sounds like you have some really interesting product innovations that would differentiate you from some of the other companies out there, and I love businesses that can scale quickly with that kind of network effect, where - by definition, you have to share and a number of people are going to sign up, and I think your free trial to paid conversion rate is good. 11%'s not bad. The struggle I have is just that it's very, very early. You know, at only a few hundred paid users at this point. I'd be super interested in your next round.

Dave: Cool.

Phil: Really interested. So, let's stay in touch.

Dave: Thank you so much.

Neal: Yeah, David. I like you. I'm out as well. There's two companies that I invested in through Techstars Chicago. One called Tangram, the other one called We Sparkle. They're not directly directly competitive. But I need to check with them first. But the other, I guess, hesitation on my part, would be - I'm not completely convinced on the grand vision and that long term piece there and how big of a business you want to build. And also there's I think more nuance that needs to exist with your breakdown of how you're going to differentiate your product. The aspect of being more human is, while well intended, I think I'm trying to understand the folks that are coming to your platform. If you're gonna switch from pulling from Calendly and other places to being people who don't use calendar bookings at all.

Dave: Yep. Cool. Thank you so much.

Jillian: I - you know - I always really try to be personally excited about an investment as well as professionally. I think you're exactly the founder because you are, sort of, a seasoned CEO in many different, across many different disciplines. But I'm not excited about this product. I'm not - potentially because it's too early and I just need to better understand the defensibility on this. But if there's room in this space for many, which it seems, as Elizabeth and Charles have brought up, I want to see where you sit.

Dave: Totally. Understandable.

Jillian: Thank you.

Dave: Thank you so much for your time.

Phil: Thank you.

[good job and thank yous]

Jillian: Yeah. Absolutely.

Neal: Great.

Jillian: He's gonna build this.

Neal: Oh he's building it. He's off to it.

Jillian: Without us

Elizabeth: He may not need any more money. So let me tell you my Calendly story. So I was a very early Calendly user. I loved the product. I cold emailed Tope and tried - I was running the 500 Startups accelerator program then. So I made him an offer on that and he was like, pushed back on the valuation. 

Jillian: Yeah the valuation was high.

Elizabeth: Went away, later came back and tried to see if he would take something at a higher price, because I was talking with some mentors of mine who also wanted in. So there was like more momentum now on this. But at that point he already was like, I'm doing enough revenue, I don't… I don’t need your money. And that was it. He gave me a t-shirt. But that was it. And he literally only raised half a million dollars - a little less than half a million dollars until the most recent raise which was in the billions of dollars valuation. 

Jillian: This guy's not gonna need it.

Neal: Bootstrapped that bad boy.

Jillian: I mean, if he already has 600 …Yeah

Josh: Extremely capital efficient business.

Jillian: Yeah. Absolute -

Neal: You like him.

Josh: Yeah. I've been trying to find the right balance between - you know, Calendly can come off as really cold and impersonal and transactional.

Jillian: But it works.

Josh: And - it does, but like when you're meeting someone for the first time and you're trying to create a new relationship, which I think about a lot as we're building relationships for the show, like how you schedule the meeting really matters.

Jillian: Really?

Josh: How you approach that. Oh yeah.

Phil: I think so.

Josh: Yeah. Think about it from a power dynamic perspective. Right, when you say, oh, go book time on my Calendly -

Elizabeth: Yeah, that means that your time is more important -

Josh: - your time is more important.

Jillian: No, no, no. I agree with that, but -

Josh: So what this allows me to do -

Jillian: But Calendly can do this.

Phil: Wait, let me hear it.

Jillian: Go ahead.

Josh: So what this allows me to do, is I don't just send on to my Calendly link, I go over to my Dotcal, it auto-generates three times in the next couple days, and I can edit them if I want, but basically within ten seconds I can copy and paste it into my email and send it to anyone I want.

Elizabeth: Vimcal offers that.

Josh: I used Vimcal.

Phil: And what was that -

Josh: But I just found Dotcal easier and faster because I book meetings all over the place. So I'll book meetings over email, over Twitter DMs, right. 

Neal: Mmm. I'm gonna try it.

Elizabeth: So let me ask you, when you had Vimcal, did you feel like there were too many features and it was too complex?

Josh: Yeah.

Elizabeth: Okay.

Josh: And it took too much -

Charles: I tried it for a while - it's doing too much.

Jillian: Okay. I'm gonna try this.

Josh: I just think he's just a product founder that just gets it.

Elizabeth: Yeah. 

Josh: I just think -

Phil: That's a good endorsement.

Jillian: He knows what he's doing. I mean, that was just - this is a confident founder that's like this is a nice to have all of you, but I don't need to have all of you.

Phil: Yeah, that's kind of -

Jillian: That kind of - that's kind of sexy.

Neal: Go make the money honey.

Elizabeth: I think he's going to be successful.

Josh: He's another one I really wanted to invest in through the Pitch fund. We needed a VC to co-invest with me.

Jillian: You might still have one. You never know.

So Dave left the room with no money. But as you heard, there were only really two people in the room who could’ve actually invested. All the others already had a horse in this calendar race. 

But later on that day….  after another pitch, DotCal was still on the investors’ minds. 

Jillian: I really, really want to learn more about Dotcal

Elizabeth: he's gonna be really successful

Jillian: You know, right? In my head I keep thinking to myself, okay, maybe I just go in for 50 K. and just call it, and I, my gut says, just do it. and it's an area, it's a category that I don't have an investment into. And I would like to learn with someone like that.

Elizabeth: and this is your only chance. I mean, I think the reason the valuation is so high is he just literally does not, he doesn't need it, need the money and doesn’t care

Jillian: and by the way, the valuation's ridiculous. It's absolutely ridiculous, but it's going to be even more ridiculous. 

Neal: Yeah. I’m cool 

Josh:  You're saying you think it'll be his last round for a while?

Elizabeth: Yeah, I think so. Yeah. Well, but just because I saw how Calendly played out. 

Jillian: yeah

After the break, Dave gets a second chance.


Welcome back. The investors couldn’t stop thinking about Dotcal. So a day later, we invited Dave back to the studio.

David: Hey friends.

Neal: My man.

Phil: Great to see you.

Jillian: Thank you for coming back.

Phil: Good to see you again. Oh you saw my email!

Jillian: Yeah. Our digital nomad.

Phil: Awesome.

Neal: Yeah. Elizabeth walked out of here yesterday, just so you know, with high conviction that you were going to be successful. She's seen this story before, she had an opportunity to invest in Calendly early on, didn't get the opportunity to get in, wishes she did. You know, there's a whole thing there. So you've got great energy, David. Like, I love it. So.

Jillian: Can I - well, can I - so, there's a big - not problem, but can you explain your valuation?

David: Sure.

Jillian: Because it's really frothy.

David: Yeah.

Jillian: Okay.

Phil: That's the -

Jillian: That's the big elephant in the room, truthfully.

Neal: He's like - yeah.

David: Well, and I mean, yeah, totally. Look -

Jillian: What am I missing?

David: So valuations are based on the market. Right. And the market is - the market is the investors you speak to, right? We have already raised $600,000 at a $15 million valuation. There's no way we're going lower in valuation. If I had my way, we're building a $10 billion company, I would - I'd raise at a $100 million valuation right now. But the truth is,

Jillian: I love his honesty.

David: Is the market for the investors - the market that we've raised from so far has an appetite for 15 million. And be it because they're in San Francisco, or be it because they're just bullish on our company, they agreed to that and so I'm not interested in going down from there. I think it's a fair valuation based on what we're building but I can totally understand your concern. And is it frothy in this market right now?

Jillian: Yes.

David: For sure. Unequivocally. You can make a case for that, for sure.

Jillian: So when did you start the raise, the 600 -

David: Yeah. Three weeks ago.

Jillian: Okay.

David: It was maybe three to four weeks ago.

Jillian: So it was in this market.

Phil: How much runway does it give you? the million?

David: Yeah. So with the money we have in the bank right now, we have 12 to 15 months of runway. We are very capital efficient.

Jillian: I might go bigger than this, but right now, I'm looking at just investing  50k.

David: Okay. That's great. Thank you so much. We would love to have you in.

Jillian: Fantastic.

David: We'd love to have you in.

Jillian: Well, I'm so happy you came back. There's no way you're not going to build this right. You have a sales mind, you have a marketing - you have the engineering. You really are quite the package.

David: Thank you.

Jillian: You're like a little super human.

Neal: Yeah. You're special, man.

Phil: I really want to invest. I really want to invest in this. Ah - I'm a disciplined investor, though.

David: Yes.

Phil: And I just - I cannot get comfortable with the valuation. I mean, I want to, man. I really do. But I just - at, you know, just out of beta, 5000 a month in revenue, 15 million dollar valuation - I just can't - I can't.

Jillian: This is gonna come back and bite you, you realize that? 

Neal: That's what Elizabeth said.

David: We can get you in another round. We can get you in another round if -

Jillian: Yeah. Another round. And that's me 3x, 5x, and then you're going to turn to me and you're gonna -

David: Well, hopefully more, but you know I’m kidding.

Jillian: Fantastic.

David: Thank you so much.

Phil: Keep me in mind for that one.

David: Cool. Thank you. Thank you.

Jillian: Absolutely.

After all that, despite the valuation, Jillian is ready to invest 50k in Dotcal.

And I got my wish! A VC to invest with me. As you might remember from episode 101, The Pitch started a fund where we co-invest alongside the investors on our show. And as someone who is apparently quite passionate about scheduling apps. This was a deal I didn’t want to let slip through the cracks.

After The Pitch I connected Dave to Jillian. A few emails went back and forth and everything looked good to go. Dave sent the investment docs over for a signature. And then… we all got a message from Jillian. Here’s Dave.

Dave: So, it turns out that one of her portfolio companies has pivoted into a competitive space as ours.

Josh: Wait, one of her portfolio companies is not already building a calendar app, they pivoted into what you're doing.

Dave: Yeah, presumably they were working on something totally unrelated. You know, Jillian was, Jillian was going off this information and then, one of our companies said that they had pivoted, into something that we're doing. So look, scheduling is a competitive landscape. So yeah

Josh: Yeah, apparently lots of money in scheduling Everybody's pivoting into scheduling. What did you think when you saw that email? Like, she was all pretty excited to invest. Like she was ready to wire the funds, 

Dave: You know, I, I don't know. It was bummed. I, I, I think Jillian as an investor would've been a fun person to work with. She has a lot of good energy. She brings a lot of good ideas to table. She has a lot of good connections. So with regards to that, yeah, like, am, am I bummed that I can't take her along for the ride right now? For sure. Definitely bummed, but, the $50,000 will come. It's fine. We'll get other investors.

Josh: So.... That leaves me in a bit of a conundrum cuz we have this fund. I don't know if you've heard about it.

Dave: Yeah! 

Josh: We've raised almost 1.5 million in seven days. So like, 

Dave: congrats!

Josh: listeners of our show are so amped to invest alongside the investors on our show but Perhaps I should have seen this coming where like an investor like backs out because of a technicality, right? Where like great business, they still want to invest and would invest if it weren't for, one of their portfolio companies pivoting. But like still this is a great opportunity. So I'm kind of stuck with like how do we make this work for the fund?

We, at the pitch, had this simple idea for our fund. Invest alongside the investors on our show. But what exactly were we supposed to do here? Jillian got all the way to the finish line, but had to back out because of a conflict. 

It almost felt wrong for us NOT to invest. The opportunity is right here, for a company that all these smart investors think could be huge. But they can’t invest. So …. shouldn’t we? 

Willem: am I loud and clear? Sorry about the technical difficulties. I'm actually calling in on my phone…

This is Willem van den Bosch. He’s an Investor at Soma Capital. A seed stage venture capital firm out in Silicon Valley. 

Josh: How much Did soma put into Dotcal in this round? 

Willem: So we invested 200,000, which is like relatively standard, for us at that that early stage.

We wanted to talk to Willem, because depending on his answers, Soma capital could be a VC we choose to invest alongside.

Josh: I would love to hear how you came to a decision to invest in DotCal and you know, how the conversations went starting, I guess, with that first meeting with David. 

Willem: Yeah, certainly. One of the first things that initially struck us when we connected with David was he has this deeply ingrained passion and enthusiasm for what he's building, and this excitement is immediately well understood as soon as he begins talking about Dotcal.

Josh: Mm-hmm. 

Willem: I think this spark is one of the intangible characteristics of founders that we've noted kind of within successful founders in our portfolio that like aligned. It's like you have kind of strong founder product alignment. And founder conviction. Which ultimately is very important as dotcal continues to scale. It's very easy to, to kind of see that David just has a love for building things and tinkering. I, I think like ultimately we like supporting these people. We kind of like to back scrappy founders, non-traditional, that have been immersed in various startup ecosystems. 

Josh: Yeah.

Willem: Have tried, maybe already failed. 

Josh: Okay. So like, he doesn't he doesn't come from an Ivy League background, like I know about his experience in startups, but…

Willem: yeah, so, so, so he is not an Ivy League, he's not a Harvard MBA or former investment banker. But in terms of street smarts, I think David could stack up against the very best founders, just given the diversity of roles that he's been involved with, as well as kind of having this longitudinal view of the startup ecosystem over the last 10 years. 

Josh: Yeah. So, yeah, I guess jump into the thesis next

Willem: Awesome. So I think the core kind of thesis, I think at the end of the day, whatever way you cut it, the market is still largely underpenetrated. There's something like 1 billion knowledge workers in the world, is the, the market large enough to support several unicorns in the scheduling space. And this is where it gets really interesting. DocuSign, multi-billion dollar publicly traded company, they currently, dominate the, the kind of e-signature space. They also have an enterprise product. 

Josh: Yeah. 

Willem: Calendly is currently the market leader in scheduling. Our kind of approach to like, can this like coexist, stand on the shoulders of giants along these like larger later stage or publicly traded companies. Our view was that DotCal's taking their business in a slightly different direction. David's broader ambition. It's the vision to create a networking platform that allows professionals to connect with other professionals and book time within this Dotcal ecosystem. And this is a little bit further out on the product development curve, but like how I understand it is a LinkedIn plus Slack plus Calendly for your professional network. So a scheduling hub, a knowledge exchange.  And a platform where I as a VC investor could connect with Josh even before we were connected. And I could go onto your kind of scheduling page and say, write you a note. Say, Hey Josh. Noted that you're kind of closely following,you're in touch with a number of phenomenal investors, and may maybe you have a number of friends we have Mutuals. I would love to spend 15 minutes getting to know you and that entire end-to-end process is done kind of seamlessly within the Dotcal ecosystem. 

Josh: Yeah. Like a system for, for meeting people where the scheduling is already integrated. All you need is like an, an opt-in from both parties.

Willem: Exactly.

Josh: And in this case with, with Dotcal, when you looked at their fundraise, David's got a $15M cap on a SAFE note. You know, what's the calculation for you guys? in determining whether that's a, a good investment.

Willem: Mm-hmm. I I think in terms of how we evaluate dotcal at 15, I think a couple of things that maybe stand out, the first of which is, I, I personally like look at David's experience and say like, this is, like, he has multiple notches on the belt. He is not a like call it like 17, 18 year old kid that just dropped out of college. Like this man understands startups.

Josh: there's a value in that 100%

Willem: Yeah. And then the, the second thing, when the, the deal crossed our plate, he already had 7,000 booking pages created and it was growing at 45% month over month, booked meetings. And so there is traction, there are real users and growth is starting to inflect. Point number three is like at maturity, I, I think like as I kind of envision this business, there are relatively low operating costs. This should be an 80% gross margin business at its core.

Josh: Mm-hmm. 

Willem: And then the last piece to, to kind of mention here is like, it it is a recurring revenue stream. And so when you're comparing this against a capital intensive business that's, let's say, building satellites. Like you start to think that like this 15 million is, is more attractive.

So will The Pitch fund invest in Dotcal? Subscribe to the Pitch+ to find out…

Just kidding just kidding! Sorry… I had to do it.

Charles has LetsMeet, Elizabeth has Vimcal, Jillian has whatever company just pivoted into scheduling, and now The Pitch Fund …. has placed our bet on Dotcal.

Josh: Do you want to do a syndicate and let listeners invest as well? 

Dave: Yeah, totally. I would love to do a syndicate. Yeah. 

Josh: Okay. So you just wanna do like, do a hundred thousand and see if we fill that up? 

Dave: I, I think it's awesome. I, I think I would love that! 

If you would like to invest in Dotcal, alongside Soma Capital and The Pitch Fund go to - that’s d-o-t-c-a-l. 

Let the calendar wars begin.

The Pitch is me, Josh Muccio, Lisa Muccio, Kerrianne Thomas, Anna Ladd, and Enoch Kim.

Music in today’s show is from The Muse Maker, Breakmaster Cylinder, Sol Rising, Shaky Faces, Fairing and Memory Palace.

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Next week on The Pitch… 

Elizabeth: Can we go back to the business model for a second?

Kehan: So the current business model is we take a part of the commission.

Elizabeth: And have you gotten any commission to date?

Kehan: Yes. We closed one transaction.

Jillian: One transaction.

Kehan: Yeah.

Jillian: okay.

See you next Wednesday.

The Pitch, Inc. and their respective employees and affiliates do not provide investment advice or make investment recommendations. The information provided on this show should not be used as the basis for making investment decisions. Listeners should conduct their own research and consult with their own investment advisors before making any investment decisions. 

Jillian Manus // Structure CapitalProfile Photo

Jillian Manus // Structure Capital

Investor on The Pitch Seasons 1–10

Jillian Manus is Managing Partner of an early-stage Silicon Valley venture fund, Structure Capital. Branded “Architects of the Zero Waste Economy," they invest in underutilized assets and excess capacity. She was named one of the top 25 early-stage Female Investors by Business Insider in 2021. Jillian serves on numerous corporate and non-profit boards, these include: Stanford University School of Medicine Board of Fellows, NASDAQ Entrepreneurial Center Board of Directors, Fuqua School of Business at Duke University.

Charles Hudson // Precursor VenturesProfile Photo

Charles Hudson // Precursor Ventures

Investor on The Pitch Seasons 2–10

Charles Hudson is the Managing Partner and Founder of Precursor Ventures, an early-stage venture capital firm focused on investing in the first institutional round of investment for the most promising software and hardware companies. Prior to founding Precursor Ventures, Charles was a Partner at SoftTech VC. In this role, he focused on identifying investment opportunities in mobile infrastructure.

Elizabeth Yin // Hustle FundProfile Photo

Elizabeth Yin // Hustle Fund

Investor on The Pitch Seasons 6–10

Elizabeth Yin is the Co-Founder and General Partner at Hustle Fund, a pre-seed fund for software startups. Before founding Hustle Fund, Elizabeth was a partner at 500 Startups, where she invested in seed stage companies and ran the Mountain View accelerator. She’s also an entrepreneur who co-founded the ad-tech company LaunchBit, which was acquired in 2014. Her book is called Democratizing Knowledge: How to Build a Startup, Raise Money, Run a VC Firm, and Everything in Between.

Phil NadelProfile Photo

Phil Nadel

Investor on The Pitch

Phil Nadel is the Founder and Managing Director of Forefront Venture Fund and of Forefront Venture Partners, one of the largest syndicates on AngelList. He has started and sold several companies and has invested in more than 200 startups with several exits.

Neal Sáles-GriffinProfile Photo

Neal Sáles-Griffin

Investor on The Pitch

Neal Sáles-Griffin is an entrepreneur, teacher, and nonprofit leader. He co-founded the first beginner-focused in-person coding bootcamp, and ran for mayor of Chicago in 2019. He's currently the Managing Director of the Techstars Chicago accelerator as well as the Techstars Rising Stars fund, and is an Adjunct Professor at Northwestern University's McCormick School of Engineering where he teaches entrepreneurship.

David MatthewsProfile Photo

David Matthews


CEO of Dotcal and serial entrepreneur with a knack for product-led growth companies and design-first startups. Previously ran YC-backed Partnered (SaaS), Billowby (e-commerce), and Ree Rah (growth agency). Walker of long distances and lover of cute dogs.