How Mayday Is Building an AI Calendar Assistant on $3.75M Raised With 13 People (Interview with CEO Jeremy Bell)

Introduction and Guest Background

Nathan Latka

00:00Hey, folks. My guest today is Jeremy Bell. He's the founder and CEO of Mayday. Previous, was the founder of wadid.io and partner at Teehan+Lax, which was acquired by Facebook. Also helped create the Facebook portal based up in Toronto. Jeremy, you ready to take us to the top?

Jeremy Bell

00:13>> Yeah. Pleasure to be here. Thanks for having me.

What Is Mayday and How Does It Work

Nathan Latka

00:15You bet, man. Alright. What is Mayday? I I believe you're competing in a very competitive space, I think.

Jeremy Bell

00:19>> Yeah. So I mean, if you look at it from kind of the surface, it looks like we're building, you know, a calendar or a scheduling tool, there's definitely a lot of products like that in the space. But what we're really building is much more like an assistant. We're we're creating a piece of software that helps people spend time in better ways. It's something that learns what your priorities are and how you spend your time, and it

00:39>> works to ensure that your schedule and your priorities are in alignment. So it's more like an assistant than it is like a just a regular calendar.

Nathan Latka

00:46So what if the only rule I wanted to feed into my scheduling was I want as much blank time on my calendar as possible? Mayday will just cancel all my meetings for me?

Jeremy Bell

00:54>> So right now, we're certainly not gonna just blindly go and remove meetings from your from your schedule. The goal is more if you think of your calendar as something that fills up over time, like if you think about a few weeks out, your calendar is likely pretty empty. What we're doing is building something that as new things come into your schedule, it is smarter about where they go. It's smarter about like how and when they're scheduled,

01:16>> how many things are being scheduled around a particular thing. So that as your schedule starts to fill up, it is more in alignment. And if you think of it like a puzzle, all the pieces are in the right place. When your day starts to go a little sideways, it'll automatically block out that time or try to protect it so that someone else can't take it or that you don't find yourself in a scenario where you've overcommitted.

01:36>> But as it stands right now, we don't have any plans just to blanket go and like remove stuff. Because I mean, people's schedules and calendars are important, right? The way they spend their time and the things that they've booked, we certainly don't wanna be in a scenario where we remove things that were not intended to be removed.

Nathan Latka

01:52Yeah. I mean, my biggest pain point right now with calendar is I always I basically wanna optimize for as many free chunks of time. Chunks, big chunks of twenty minutes of free time is useless because it's just context switching. You know, three hours of free time is valuable. So, like, batching stuff is really difficult. So right now, use Acuity, and all we do is we schedule for, like, you know, one hour for podcast interviews. And when that

02:12hour fills, we add three more slots on before or after it to batch it, but it's a pain in the butt to log in every time to do that. It sounds like maybe you can do that with some rule based system or something.

Jeremy Bell

02:21>> Yeah. Like what we're building again, if you think of like a really great assistant, that assistant would have that context, that kind of macro view. So there's really a few kind of parts to it. Mayday is an app that you use on your phone and your desktop. Its intention is to replace the calendar that you use every day. In the cloud though is where we're doing a lot of the intelligence. It's where a lot of the

02:41>> analysis is happening. And it's how we look at what's coming in and what's going on in your schedule. And we start making changes based on what we see. We map out your we analyze, like, how you spend time and also who you spend time with. We also have a feature that we call smart tags where you can for instance, you can create, a scheduling link where you've you've created some things behind the scenes where you've tagged

03:03>> it essentially saying, anyone who schedules something, treat this meeting like this. And with that smart tag, you can assign rules and budgets and buffer times and other things like that so that as you're scheduling things, the times that are made available are reflecting of those rules. Yep. So that you don't need to micromanage your schedule. Like, you shouldn't have to go in and change all the different rules as your calendar fills up. Like a really great

Product Deep Dive: Smart Tags and Scheduling Intelligence

Jeremy Bell

03:28>> assistant, that assistant would be doing it for you so that you can trust that when you give that link to someone to schedule, it's taken care of Understood. You want to spend time. Right?

Nathan Latka

03:36Yeah. Okay. I think you guys all audience understands the product now, which is great. Let's dive a bit more into the sort of the economics here. So is this for a consumer or a business is gonna pay for 100 seats right off the bat?

Jeremy Bell

03:46>> Yeah. I mean, the the reality is the answer is yes to both of that. We've taken a kind of bottoms up bottoms up approach where we're building this for individuals in the sense that managing your time is a hyper personal thing. So you you the individual needs to want to and love to use the product. As we scale, I mean, it's so much of how you spend time is with other people. Like, the things that you

04:07>> schedule in your calendar are often with coworkers and other people that you you know, that that that are either at work or business related. So we what we have teams functionality that's coming and this will be there will be teams offering a company like offerings as well. So short answer is if you wanna use it individually, there's an option for that.

Nathan Latka

04:21Got it.

Jeremy Bell

04:22>> There'll be a free option, there'll be a paid option, then there'll be a

04:25>> teams option.

Nathan Latka

04:27Oh, what's going on there, YouTube? Good to see you guys. Now imagine this. You love watching these interviews with SaaS founders, but imagine if we took all of the valuation data out from over 2807 interviews I've done manually. Saves you a lot of time. Well, we've done this. We've built it into the beautiful interface inside of Founderpath. Check this out. I'll show you how you can access this in a second, but you log in, you connect

04:50your Stripe account, you see your valuation real time, you can see what it changed over the past eighty eight days and even set goals for valuation this year. Now the secret evaluation is there's many different ways to value a SaaS business. So the reason you're gonna see three or four different valuations inside of your Founderpath dashboard, this is all free by the way, is because depending on who's doing the buying of your SaaS company, you're gonna

05:14get a different valuation. A VC is gonna pay a different valuation, Private equity firm is different. If you're gonna do a minority sale, that's different. And if you sell the whole business, that's a different valuation. You can see all those when I hover over here. Right? So the teal is what a VC would pay. Yellow is what private equity and red is if you sold the whole thing outright. Now what's cool about this is this is

Business Model: Consumer vs. Enterprise

Nathan Latka

05:36not built off random data. Again, you guys hear these interviews on YouTube. All these datas are built from real time valuation data points founder share with us on the show. So traction 1,200,000 seed round 3.7 raise. They sold 22% of their business. Go in here and filter by the event. Maybe you only wanna see companies that have sold the whole business. Well, here are a bunch that have been acquired the valuation and the multiple. Maybe you're

06:02going out right now and you're raising your seed round. We'll go in here and look at all this recent seed deals that went down, what they raised, what valuation they raised at, and what percent that they sold. There's never been a larger dataset of SaaS valuations than what you can get now inside of Founderpath. And we're thrilled to bring it to you. All right. We're gonna go back to the YouTube video here in a second. But

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Beta List Size and Growth Tactics

Nathan Latka

06:50the interview. So what what is the average paying customer pay today?

Sponsor Break: Founderpath Valuations

Jeremy Bell

06:54>> Well, right now, we're in a closed beta, so no one's paying anything.

Nathan Latka

06:57Alright. So pre

06:58revenue, how are how many folks are on the beta list?

Jeremy Bell

07:02>> We've got we've got tens of thousands. I don't know if I'm ready to to share the exact number yet, but

Nathan Latka

07:06we're I mean, who care I mean, who cares? Right? It's a beta list. But what is important is how you're building it. Right? So how are you how are you building such a big beta list? What's the tactic?

Jeremy Bell

07:15>> Yeah. So the way we've been we've been building out the list has been it's predominantly has been organic. There's been a lot of word-of-mouth. Some of the people that are in the we do have a closed beta. Those that are using it are also referring coworkers and stuff that comes through that process. We also have set up a well, describe as like a social listening kind of program where we have some things set up that are

07:33>> looking for people who are tweeting and posting stuff on Reddit and LinkedIn and those those messages that are talking about things that are related to what we're we're building, those get brought to us and then we usually respond to them in those respective channels. We found that to be a pretty effective method. It doesn't scale. Like, I don't think this will, you know, work for that much longer. But it's been a perfect kind of slow What

07:55>> do you use it?

Nathan Latka

07:56What tool are you using to do this the social listening?

Social Listening Tool Built with Zapier and Slack

Jeremy Bell

07:59>> It's all it's all built in it's a custom thing that that I built using Zapier and Slack. And, I mean, those are really the kind of the two main things, and then and then I respond directly in whatever channel is. So if

Nathan Latka

08:12it's So it's like if if tweet with min favorites greater than 300 and mention time management

Jeremy Bell

08:21>> Correct. Yeah. We're we're looking for things that we're looking for phrases and things that they're talking about that are relevant. So it's it it is a pretty kinda set of custom strings that we're, you know, we're filtering things by.

Nathan Latka

08:30With audience though. Right? So minimum a 100 likes or minimum five retweets, whatever.

Jeremy Bell

08:35>> You got it. You got it.

Nathan Latka

08:36Interesting. Very interesting. Very compelling. So are you you're an engineer then by trade?

Jeremy Bell

08:40>> My I started my career as an engineer, but that was many, many, many days or years ago. My background is more design and product, actually.

Nathan Latka

08:48Ah, okay. Interesting. When did you write the first line of code or your team write the first line of code for Mayday?

Jeremy Bell

08:53>> It was probably about mid two thousand nineteen, I think, is when we really started diving into it.

Funding History: Pre-Seed and Seed Round

Nathan Latka

08:572019. Okay. So you're still pre revenue today, which means you are either really rich and you're funding losses for a bit or you've raised capital.

Jeremy Bell

09:04>> It's, mean, it's a bit of well, I mean, I wouldn't say I'm rich by any stretch, but we were we were we were good at at bootstrapping and just being very, very tight with how we spent the money in the early days. We did act we have raised funds. We just actually closed a seed round. So I raised a $3,000,000 seed round that we closed just at the end of of of last year. So right right

09:23>> before the holidays, we closed that that round.

Nathan Latka

09:26Uh-huh. And what did you do? Pre seed round as well?

Jeremy Bell

09:28>> We did a friends and family round that you could call a pre seed. Like, it basically was a combination of funds from When was that? Some small some small funds here in Canada and some some friends and family.

Nathan Latka

09:39When when was that?

Jeremy Bell

09:41>> I got it kind of mid two thousand nineteen is when I did

Nathan Latka

09:43the first little bit.

Jeremy Bell

09:44>> We did in two tranches, and then the second one was probably about mid twenty it's probably like yeah. It was probably about mid twenty twenty.

Nathan Latka

09:52Okay. And what? You were talking like 500 k here, a million, or what?

Jeremy Bell

09:55>> The total the total amount in US was about 750, I think.

Nathan Latka

10:01Okay. Interesting. And so it sounds like you're able to use your past experience as a vetted entrepreneur who sold a company to Facebook, right, to sort of raise this money, hopefully, on terms that didn't dilute you too badly.

Jeremy Bell

10:12>> Yeah. Correct. Like, so my you know, to to kind of clarify, like, I was at Teehan+Lax, which was which was acquired by Facebook, I had actually left to start my first startup just before that happened. So I didn't partake in the in that, like, that exit.

Nathan Latka

10:28It was you was it your company or you were an employee there?

Jeremy Bell

10:30>> I was I was a partner there. So Okay. Jon Lax and Geoff Teehan. So Teehan and Lax were the two that founded it. I joined shortly there after they had started it. So I I was there from pretty much the beginning, but but it's definitely it was definitely their company.

Nathan Latka

10:44Mhmm. And and you I mean, was that the sort I mean, I wanna get into your personal financial situation, but did you make enough there where you have whatever, a million, $2,000,000 scrub buffer? You can sort of do whatever you want as as the next swing at the start up bat?

Jeremy Bell

10:56>> When I no. So when I left that one, I started my first start up. I mean, was again, entirely bootstrapped. Like, didn't I didn't participate in that exit whatsoever. Yeah. I raised a bit of money and then ended up exiting on that one and sold it to a company called Precision Nutrition. Made, you know, basically made all of our existing investors and myself like whole, so it wasn't like a huge liquidity event by any stretch. Enough

11:19>> that, you know, it was a good learning experience where no one walked away losing any money. Coming out of that though, I, to be frank, I had a bit of crypto that I had had put aside and there was a little bit of money that I had that I was able to pay basically myself while I worked through the the bit the little bit upfront. That kind of kept me going and then then we raised the

11:37>> the friends and family around to kind of do it proper. Interesting.

Team Size and Engineering Breakdown

Nathan Latka

11:40Alright. So what's the full team size today? How many people?

Jeremy Bell

11:42>> There are 13 of us, I think. We just hired someone actually. There's another person starting on Monday, so I think it's, like, gonna be 14 on Monday.

Nathan Latka

11:48And how many engineers?

Jeremy Bell

11:50>> It's about half of the team is engineering. All of them are actually now.

Nathan Latka

11:55And so imagine people listening going, okay. This guy launched in 2019. He's built startups before. They've got 10,000 on the wait list. Like, what is he waiting for? When does the paywall go up?

Jeremy Bell

12:03>> Yeah. So one of the challenging and interesting things I think about building what we're doing is so there's there's there's calendars that exist already. Right? Like, there's an expectation of what the product can do. So the surface area is actually quite broad in terms of features and functionality. We're walking this line between like, what are the things that people need and what are the unique things that are gonna truly set us apart and like really like

12:25>> build our business and, you know, build our moat, if you will. And one of things we learned early on is I didn't wanna build another calendar. I didn't think the world needed another calendar. But when you get into time management and the things that are going on, it's a really high touch thing. We heard from a lot of our early users. They're like, wow, this is really great. I love what you're building here, but I need

Why Still in Beta: Building the Full Calendar

Jeremy Bell

12:43>> to be able to see my schedule or book a meeting or change a schedule. And the idea of having to jump between different products was not great. So we we kind of realized that if we were gonna truly achieve the things that we were setting out to achieve, we had to build the whole thing. So that's what we did. We really we started on mobile. It was a kind of a a companion to your calendar. And

13:05>> now we've built a full, it's on desktop, it's on mobile. There's a lot of features and functionality that are already done, but there's still a lot of stuff that we think needs to be really there before you can truly, like, I think make it available to everyone. So we're we're taking an approach that I think is very similar to, like, the way that, like, like, Superhuman went as an example.

Nathan Latka

13:23Yeah. This is exactly I mean, this is exactly Superhuman email Mayday calendar. Direct comparison. So, I mean, do you have a guess of what you think the paywall might look like and a timeline on when you think you might launch it?

Paywall Strategy and Monetization Plans

Jeremy Bell

13:37>> Yeah. We're gonna we're definitely gonna be launching later this year. I don't know if we're gonna completely remove the wall and let everyone in. I think we'll probably still open up. Still be a waitlist, we'll still open it up more while we continue to build stuff out, but start monetizing, with what we've got. So, I mean, the objective or the, the plan is to definitely get to monetization sooner than later. I don't want us to, you

13:59>> know, this is not gonna be sustainable if we just kind of keep doing this kind of path.

14:05>> But on the flip side, like if you look at I if you look at what Superhuman's done, they've also been very methodical about how you roll it out, how you let people in, just because the expectations of what the product can do is just so important. Like, if you mess up someone's schedule, like, there are real world ramifications to that, and we want to ensure that we don't burn those bridges with early users as well.

Nathan Latka

14:24Yep. Yep. Interesting. Well, look, we'll see what happens. Certainly rooting for you. Now, are you there's a lot of ways to reverse engineer how you want your first paywall to perform. One approach is to say, okay. What's the number one usage usage activation metric on the app? Stack rank every user, and then say you only want 1% to pay, and then you set the paywall at that usage limit. So maybe it's 50 new meetings per week.

14:48Another is to just say, we don't care if it's 1% paying that see the paywall or 20% see the paywall. Anyone that adds more than three meetings per week sees the paywall. So are you taking sort of a feature based approach to the Paywall or, like, a percent of your user base approach to the Paywall?

Jeremy Bell

15:02>> We've been we've been investigating both of them. I think one of the interesting things that we have in front of us is that with calendaring and scheduling tools is you can create and build a habit with someone if there's a routine, but that happens over a period of time. So we need to find what's the right kind of threshold where we can start to enable people to get value, start to develop that habit and routine, and

15:21>> then start to pay when they've got it kind of ingrained in their lives. So we've been we've been investigating if it does make sense to have a free offering always, and then you hit a certain threshold of things and it it locks. We've been investigating some of the obvious, like, features might make sense to, like, to to paywall so that you can use the product individually, but as soon as you try to do something with someone

15:42>> else, you that you would have to pay for it. So we're still working through what's the right place to draw that line, and I don't think we've got a a complete answer yet. But I do know that it won't just be you have to pay to get in, period. So we're not gonna go down the path like a Superhuman. Like, it won't be like that.

Famous Five Rapid Fire

Nathan Latka

15:58Very cool. Alright, Jeremy. We're out of time here. Rapid Fire Famous Five. Number one, last book you read.

Jeremy Bell

16:03>> Oh, I'm actually reading The Cold Start Problem. Reading it right now.

Nathan Latka

16:07Number two, is there a CEO you're following or studying?

Jeremy Bell

16:11>> Oh, man. I mean, the original I mean, I'm sure everyone says Steve Jobs, and that was kind of, I would imagine, the inspiration. But, yeah, I can't help but follow a bunch of them on online and just watch, you know, watch how they're they're all playing out.

Nathan Latka

16:21Number three, what's your favorite online tool for building Mayday besides your own?

Jeremy Bell

16:26>> Notion. Everything that we do at at at Mayday, like, literally everything is in is in Notion.

Nathan Latka

16:31And number four, how many hours of sleep do you get every night?

Jeremy Bell

16:33>> Oh, you know, as a as a company that cares deeply about how people spend their time, we work, pretty aggressively to build a business that's sustainable and and or a staff that's sustainable. So I I get a good seven hours of sleep.

Nathan Latka

16:45That's great. And what's your situation? Married, single, kids?

Jeremy Bell

16:47>> I'm married. I got two kids.

Nathan Latka

16:48That's awesome.

Jeremy Bell

16:49>> Like eighteen years now.

Nathan Latka

16:51That's awesome. How old are you?

Jeremy Bell

16:53>> I'm 42.

16:54>> 42.

Nathan Latka

16:55Last question. Something you wish knew when you were 20.

Jeremy Bell

16:58>> I lived in Toronto and have lived here my entire life. I probably, when I was younger, would have probably benefited from just going west and and getting into the into the Silicon Valley scene a lot sooner than I did later. So that's probably one thing I probably would have would have told my younger self, was just go go on an adventure and see what what's over there.

Closing Summary and Outro

Nathan Latka

17:16Guys, part designer, part engineer. He sold companies before really cutting his teeth. Nothing massive in terms of finances, but he knows what the process looks like. Now he wants to reinvent the calendar. First line of code for Mayday, launched in 2019. They've built up a beta list of over 10,000 using some interesting things related to who's tweeting about time management with a large following or on LinkedIn, etcetera. Built up that wait list, planning to launch

17:37a paywall later this year. 3,000,000 raised recently back in December for their seed round as they continue to scale with their team of thirteen, fourteen next week. Jeremy, thanks for taking us to the top.

Jeremy Bell

17:46>> Hey. My pleasure.

Nathan Latka

17:49One more thing before you go. We have a brand new show every Thursday at 1PM Central. It's called Shark Tank for SaaS. We call it deal or bust. One founder comes on, three hungry buyers, they try and do a deal live and the founder shares back end dashboards, their expenses, their revenue, ARPU, CAC, LTV, you name it, they share it and the buyers try and make a deal live. It is fun to watch every Thursday 1PM

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