John Li - Vimcal

Vimcal: Overcoming a 1.5 Month Runway and Getting Traction – with John Li [355]

Vimcal: Overcoming a 1.5 Month Runway and Getting Traction

John Li is the co-founder and CEO of Vimcal, a calendar app designed to help busy professionals and remote teams.

In 2017, John and his co-founder Michael were accepted into YC with an idea for an augmented reality product.

However, they soon discovered the market wasn't ready, so they pivoted to a fitness app, which also didn't get traction.

After two years of hard work and long hours with limited results, they had only eight months of runway left.

The two founders were faced with a critical decision. They could either quit and go back to full-time jobs or they could fight and keep going.

They chose the latter and in 2019 the idea of Vimcal was born.

But building a calendar app proved more difficult than they'd imagined, and by the time they launched, they had just 1.5 months of runway left.

Once again, they were on the verge of shutting down. Yet, despite the odds, the founders managed to keep Vimcal alive and gain traction.

Today, Vimcal is a trusted tool for professionals aiming to optimize their calendar management and save time.

In this episode, you'll learn:

  • How the founders shifted gears when their initial ideas didn't pan out, moving away from AR and fitness app concepts to find a winning business idea.
  • How they hustled to keep their dream alive when cash was running out, turning limited runway into a successful business that eventually gained traction.
  • How they tackled the complexities of developing a calendar app, overcoming significant technical challenges, and finding success.
  • How the founders refined their sales strategy, successfully attracting customers and investors to save Vimcal from shutting down.
  • How they built valuable strategic partnerships, leveraging industry connections to scale up and enhance Vimcal's offerings.

I hope you enjoy it.


Click to view transcript

This is a machine-generated transcript.

[00:00:00] Omer: Welcome to another episode of The SaaS Podcast. I'm your host, Omer Khan, and this is a show where I interview proven founders and industry experts who share their stories, strategies, and insights to help you build, launch, and grow your SaaS business. In this episode, I talked to John Li, the co-founder and CEO of Vimcal, a calendar app designed to help busy professionals and remote teams.

In 2017, John and his co-founder Michael, were accepted into YC with an idea for an augmented reality product. However, they soon realized the market wasn't ready, so they pivoted to a fitness app, which also didn't get traction after two years of hard work and long hours with limited results. They found themselves with only eight months of runway left.

The two founders were faced with a critical decision. They could either quit and go back to full-time jobs, or they could fight and keep going. They chose the ladder. And in 2019, the idea of Vimcal was born, but building a calendar app proved more difficult than they'd imagined, and by the time they launched, they had just one and a half months of runway left.

Once again, they were on the verge of shutting down. Yet, despite the odds, the founders managed to keep Vimcal alive and eventually gain traction. Today, Vimcal is a trusted tool for professionals aiming to optimize their calendar management and save time. In this episode, you'll learn how the founders shifted gears when their initial ideas didn't pan out.

Moving away from AR and fitness app concepts to finding a winning business idea how they hustled to keep their dream alive when cash was running out, turning limited runway into a business that eventually gained traction how they tackled the complexities of developing a calendar app, overcoming some significant technical challenges in order to find success.

We also talk about how the founders refine their sales strategy, which enable them to successfully attract both customers and investors who helped save Vimcal from shutting down, and how they built valuable strategic partnerships, leveraging industry connections to scale up and improve Vimcal's offering. So I hope you enjoy it.

Okay, John, welcome to the show.

[00:02:11] John: Thank you. Thank you for having me.

[00:02:13] Omer: Do you have a favorite quote, something that inspires or motivates you that you can share with us?

[00:02:16] John: Yeah. My favorite quote is from the movie Lone Survivor. It goes, “Anything worth doing is worth overdoing”. And I see that as kind of a mantra for everything I like to do.

[00:02:26] Omer: Nice. So tell us about Vimcal. What does the product do? Who's it for? What's the main problem you're hoping to solve?

[00:02:32] John: Vimcal is the world's fastest calendar, and it's beautifully designed for very busy people. Our ICP are people with a mix of a lot of internal meetings as well as external meetings. So we build mainly for founders, VCs, managers, and even executive assistants.

[00:02:49] Omer: Nice. Okay. So there's a lot to unpack here. Let, let's, let's start by, What were you doing before you started Vimcal? What's your background?

[00:02:58] John: Yeah, I was trained as a software engineer. I worked at Twitter as well as Apple and a smaller startup before I worked at Vimcal. But I always knew that I wanted to do my own startup pretty much since college.

So the business was founded in 2018. How did you, where did the idea of Vimcal come from?

We got the idea for Vimcal when we started our previous company, which was actually a fitness company. When I was fundraising after YC Demo day, I had to schedule I think 30 meetings with investors per week, and it was just chaos.

I had to schedule meetings in Barcelona with people in Asia and Australia and all over Europe, and I ended up actually making a lot of mistakes with time zones, booking meetings at 4:00 AM for people. And so it was always this kernel that was in the back of our minds. And in 2019, after doing the fitness idea for a year, we actually decided to pivot.

And that was one of the first ideas we had. Just looking back at problems we had in our own past. I had also built a calendar as a side project when I was in college just to learn. I was development so. We already had kind of that interest in calendaring, in productivity, just from the get go.

[00:04:14] Omer: So lemme get this straight. So this did, did it start out, I think as a augmented reality idea?

[00:04:20] John: Initially, yeah. In 2017, on nights and weekends, Mike, my co-founder and I would hack on this AR idea and we actually applied to YC with that in 2018. And when we got in, we quit our jobs. Did that, but. It actually didn't end up working. So mid batch, we pivoted to that fitness idea I was talking about.

Did that for a year and then in 2019 we pivoted to Vimcal and since, since then it's been all Vimcal.

[00:04:48] Omer: So. Okay. And so, so from AR to fitness to calendar, from what I understand, you, you wrote a, a Twitter thread and one of the things it said was that when you started Vimcal, you had about one and a half months.

Of runway left and so the, the business almost died. And so you and your co-founder, Michael, were basically like mentally preparing yourselves to go and apply for jobs, but something kind of made you guys kind of push this through to the end. So just tell me like what was going on during that period where, you know, you've got a month and a half runway left and so you come up with this idea of doing a calendar app as kind of the third iteration of this company.

What were you thinking? Like, there must have been a, a, a sense of urgency not only to ship this thing but accomplish what in the next month, month and a half?

[00:05:51] John: Yeah, that's a good question. Like you mentioned, it was the last shot we had on goal. When we launched we had a month and a half of runway.

And so I remembered about two months before we launched, we were in office hours with our YC partner, Aaron at the time, and we were just dejected. We were like, we're outta money. We don't know what to do. You know, this thing is taking a lot longer to build the prototype for the MVP to launch and while we were dejected, there was also the sense of lightness. Cuz there was no other option, right? You just had to do this the best you could. If it works, it works. If it doesn't, it doesn't. So it's this like juxtaposition of feelings inside. It's like this piece, but also this like high-strung stress.

And I remember just sitting there and we just decided, Hey, launch this as quickly as possible and try to grow the thing and get money from investors, from users charged from day one. That was a decision we made out of necessity, not because it was a strategy. A lot of companies like to launch a free product, get users, grow that, and then convert them.

I had to jump on every single call with every single user. When we launched and I would show them the product. I had this script, I would practice over and over again till I would say I perfected it. And at the end of the call the user would be pretty excited and I would say, okay, can I send you a $15 invoice?

And a lot of times they said yes. So we got a little bit of revenue. Wasn't really enough to save us. But on one of the calls, and I think we had three weeks or a few weeks of runway left at that point I said, Hey, can I send you a $15 invoice for a subscription? And that user said, how about I put in a $5,000 check instead?

And that moment, I can't even describe. It was like so much weight was lifted off my shoulders. We had already prepared legal docs to shut down. I have a screenshot of Mike's email to our lawyer asking how much the legal fees are, and, and the lawyer was like, oh, in California it's like $800 for your company or something like that.

So we were fully prepared to do that. But that $5,000 saved us. A few days after that, I think we got another check for like one 50 and that really put us in a good position. And for the next six months after that, I actually used those onboarding calls as a vehicle to fundraise. The thing a lot of people dunno is that we launched Vinal a month and a half before Covid lockdown.

So if you remember at that time, the first few months, no one was giving out money. So it was also like the scariest time to be launching something. But because I was showing everyone one by one how to use the product, I was, you know, I think the desperation showed also the passion for the product.

A lot of investors did write checks at the time, and it did save our company.

[00:08:46] Omer: Yeah, I mean, that, that's, that's a great story and kind of shows you that, you know, the, the power of persistence and, and not giving up where, where are you today in terms of revenue? And what's the size of the business?

[00:09:02] John: Our team is only nine people. We're spread out all over the US and in South America, and our goal is to get to 1.5 million ARR in the next 12 months. And at that point we'll also be profitable. So we're really excited. We raised a very small precede a few years ago and yeah, we've been a since the beginning. So whatever we raised, we make sure that it lasts us for a long time.

[00:09:25] Omer: So in, in total, how much have you raised so far?

[00:09:27] John: I would say in total about 2.4.

[00:09:29] Omer: 2.4 million. Okay. Cool. All right, great. So you, you've, you've last minute kind of effort for this third idea. You, you're kind of going through and, and doing these Zoom calls, it turns into kind of this fundraising opportunity.

What. What did you do next? So you guys have got a little bit more breathing space, but you can't take your foot off the pedal. There's still a lot of pressure here. Where were you finding these people to get on the Zoom call in the first place?

[00:09:59] John: We were weightless only for a long time. And looking back now, that is one of the best growth strategies you can have as an early company to be, you know, early access, beta only, weightless only, whatever you wanna call it, but basically getting off gating off access to select users.

So there are a few advantages to that. One is you can be very selective about who your users are. So we had tens of thousands of people on our wait list you know, just in the first few months. But I think we only let in 20 something percent in the early days. And we made sure that they fit our profile of our ICP, which again is people with a lot of internal and external meetings.

It's a lot of founders VCs. And we would also ask one question, which is, what other apps do you use? And we found that. That was one of the best tellers of who would be a good vemal user. It's a very good qualifying question. So if they used Calendly, Google Calendar and Superhuman, it was actually pretty likely that they would be a good fit for Vimcal.

So in the early days actually, we were able to convert I think 70% of users at the end of the call, if we ask them, Hey, can you put down your credit card? 70% will say yes and pay on the spot. And I think if they fit one of the. Calendly and Superhuman. It was like a 90 something percent conversion. Wow. So that was, that was one of the tactics that we use. And it worked beautifully.

[00:11:23] Omer: Yeah. I mean there's, there's a lot of similarities I see between what, what you're doing here in the calendar space and, and what Rahul and his team are doing at Superhuman. This idea of this waitlist, a lot of people may just have like a very simple thing where people just put in their email address for a waitlist.

The trouble is, It's, it's a very low bar, so you get lots of email addresses potentially, but there's no way to qualify them. And if you've got a list of like 5,000 people, you don't wanna get on a Zoom call for 30 minutes for each one of those people, cuz it's gonna be a huge waste of your time. But you, you were doing it a little bit differently, like you were asking people to fill out kind of a, a form a answer some questions.

So you, you, you kind of mentioned like asking them what apps they were using, what other questions were on there. Like basically if, if someone's kind of not, not doing the wait listing the right way, what are some ideas they could steal from the questions that you were asking?

[00:12:19] John: So we made our type form intentionally kind of long as a point of friction. If you filled it out, that's a signal that you might be actually interested in this. But to help with that, the first question we asked was one that. It didn't really matter to us, but it kind of spoke to the user. So if they see that question, they're more likely to answer the first one. And if they answer the first one, they're much more likely to fill out the rest.

So the first question was, do you feel overwhelmed by the amount of meetings you have? And I think last time I checked it was like 92% or 91% said yes, which is like, okay, you're probably a Google Calendar user because we want really busy people. So that was one of 'em that's just kind of to ease, ease the user in.

And we asked a mix of qualifying questions and just qualitative questions for us to learn. So the qual, the qualifying questions included the one I just mentioned, which was what other apps you use. It was, what role are you and which of the following is true? I have a lot of external meetings. I have a lot of meetings, I have a lot of recurrent meetings, all the above.

And we catered more in the early days. Still a little bit now, but especially in the early days to people have a lot of external meetings. So if you mentioned that, oh, I only have recurring meetings like I'm an engineer, or I only have internal meetings like I'm a manager or pm we would actually not let you go through till much later in our process when we had more features for those types of users.

And then there were the ones that were obviously like, oh, if you don't answer this one way, we just can't work with you. Like you use Google Outlook. We didn't have Outlook until six months ago, so if you answered Outlook, you just, sorry, we can't get to you right now, but we'll reach out to you when we have it.

[00:14:02] Omer: So the, the goal here was basically to do two things. You, you said, talk about cr creating some friction in terms of kind of a, a validation sign. How much do people actually care about this, filling out a longer form? Takes more effort than just an email address. And then secondly, asking enough of these qualifying questions.

So when you do open up or you get somebody on a Zoom call, You are getting more of the right people and your conversion rate or close rate to sales is higher, which is kind of exactly where you were. What did you say the percentage was that you were closing on these Zoom calls?

[00:14:41] John: 70% for people, all people we let in, and then if they used the qualified apps, then it was like 90, 90 something. I don't, I don't remember anymore now.

[00:14:51] Omer: That's awesome. Okay, great. So just like with. Superhuman. The, the biggest, it, it, it's like, you know, one of the things that Rahul talked about when he was on the show was this idea of how they, they continue to figure out their ICP and hone that target person to the point where, you know, they were only really focusing on people who would be like very disappointed if they weren't able to use Superhuman. Right?

And, The vast majority of people who use email would never pay $30 a month to use Superhuman. But there's a small percentage, and that's gonna be a significant number of people who see that as an absolute, you know, worthwhile investment. Right. And I was one of those people, right? For like years I resisted superhuman.

I was like, there's no way I'm paying $30 a month. And, and now I'm kind of like, I don't know if. I wanna stop using Superhuman anymore. Right. It's like, I'm kind of, but I think it's because I, I fit into that icp. Right. It's just, so, I think it's similar with you. Like the majority of people out there are gonna be, I use Google Calendar and I use, you know, whatever, and it's free.

So why would I pay $15 a month for a calendar app? So I'm sure you, you, you kind of faced that issue and it's like, what were some of the challenges that you, you faced? Trying to sell, sell that for $15 a month?

[00:16:24] John: Yeah, that's a very good question. Like you mentioned, there are a lot of free options out there, and I will say Google Calendar for the record is a fantastic app.

We've studied a lot. I think it's one of the better-built apps out there, even though a lot of people like to dunk on them when they come to Vimcal. I actually say, Nope, I love Google Calendar. And like you mentioned, it really depends on who you're building it for. I like to call calendar and email the pillow apps.

Wait, if you think about the first apps you open in the morning when you're in bed, or the last ones you close you know, when you're in bed at night, it's usually probably email. Calendar, TikTok, you know, iMessage or WhatsApp. So there are these five or six apps that are prime real estate that everyone uses.

White collar, blue collar, jobless, employed, doesn't matter, right? And so, first of all, it's a huge market. Second of all, if you build the best experience for any of these apps, you definitely have a huge market. And so, People think that sometimes, oh, if I carve out this ICP or that it's gonna be a small market.

But we've actually seen that. We are constantly surprised by how many people have these problems. So going back to your question, which is all these free options, like how, how do we deal with that? There are a lot of people who are not satisfied with. An app that is built for a billion people, which is like Google Calendar or Outlook.

There are a lot of people with very specific needs and it actually messes with their day-to-day work. A lot of people have to schedule meetings in other time zones with three, four people whose calendars they have to check conflicts for, and so all these different. Very intricate use cases come up and proms come up and there is just nothing really that exists for that.

And a lot of user, a lot of people like will piece together apps here and there and duct tape together a solution and then end up with the wrong meeting like I did before I created Al with my co-founder. So, We are always surprised by just how many people that we can surface. And the numbers growing every day.

We don't plan on stopping anytime soon. And the cool thing is the ICP also changes as your product grows and as you add more features, you can actually target more ICPs. So in the early days, very early days, those founders VCs and then it be our ICP became. People with very busy calendars. And as of a year ago, we improved our multi-calendar experience, introduced Outlook on top of Google integration, and now our newest ICP, or one of our newest ICPs is people who have like four or five calendars.

So there are a lot of consultants out there with four or five gigs, and they're connected to four or five companies, Google or Outlook accounts, and they just need to see it all in one, one place. And this is constantly evolving. Today before recording this, we just launched our second product, which is Vimal Maestro, which is the first calendar for executive assistants, chiefs of staff, VAs, any admin that schedules on behalf of someone else. So this evolves as you keep building, as you keep pushing.

[00:19:39] Omer: I, I, I wanna come back to Maestro in a second. Can you, can you gimme one or two examples of features in Vimcal that don't exist in Google Calendar that really are kind of like some of the favorite things that you know, your, your customers love about the product?

[00:19:57] John: Absolutely. There are, there are two main ones, and you can use 'em together. So when we launched Vimcal, we came up with this new interaction, which we call slots, which is you just look at your calendar and if you want to send me sometimes, for example, to meet next week. You just use your mouse and you drag those times on your calendar and we will type out, Hey, are you free Tuesday, 4:00 PM Friday, 5:00 PM whatnot.

And you never have to type that text out before. Anymore before you had to look at your calendar, find a few times, go to your email type, Hey, are you free? Monday through to four, go back, check the next slot, go back. And we actually measured it and sending an availability to someone over email, used to take 77 clicks or keystrokes.

And with Vimcal it takes eight and it's actually ridiculous. And I think we got it down from. Three and a half minutes per meeting to about 10 seconds to schedule a meeting. Wow. It's actually pretty nuts because that function also prevents going back and forth over email to do it again and again and again. Because the times you mentioned are now taken.

[00:21:04] Omer: And then you said there was two, two features.

[00:21:06] John: Yeah. And the second one that we launched was time travel. Time travel is this text box. You can type in any city in the world and we'll pull up that time zone next to yours. And so when you send these times, when you create meetings, you can actually send those times while respecting both time zones.

So let's say you're in Paris, I'm in New York, and I wanna send times in your time zone instead of. Going to my calendar, writing out all the times, going to time world or whatever those websites are, converting everything by the five or six hours, and then rewriting that and pacing it. All I do is go on Vimal, click the time travel button and just type Paris.

Everything gets converted. I copy and paste. I'm done.

[00:21:53] Omer: Are, are you guys also big on keyboard shortcuts as as kind of like another kind of factor for speed?

[00:21:59] John: Yeah. My co-founder Mike, is a fanatic for hot Keys. He said when we were pivoting, that is one of the conditions if we're gonna do this, is that everything can be done using my keyboard.

He does not touch his mouth. So absolutely. Yeah, everything can be done with your keyboard.

[00:22:16] Omer: Great. So we've established like some of the ways that it's different to Google Calendar that. Justifies the, the $15 a month. And again, it's a certain ICP that it's gonna appeal to and not, not to everybody. So the, the one question I had for you was about the, the availability.

So if somebody is using Calendly today and they switch to Vimcal, does that mean they don't need Calendly anymore?

[00:22:44] John: We have actually three availability features. So the first one is the one I discussed earlier called slots where you can just drag and copy. The second one is called personal links, which is more or less like a county link.

Pretty much every calendar or scheduling app today has this concept of a calendar link or a booking link. Well, I call it what I call a general link. And the third feature we have for sending availabilities is what we call group vote, which some people call poll. It's a doodle basically. So when you join Vimal, our goal is to let you cancel four to five other subscriptions or websites you go to to schedule a meeting.

You'll be surprised that a lot of people just to put one meeting on the calendar will use like, Again, the time roll buddy, a Calendly or a Doodle. And then they will actually use some other little widget to put a Zoom meeting on someone's calendar. And I think the average user probably saves 20 to $30 a month by using Vimcal.

And Vimcal is $15 a month.

[00:23:47] Omer: Got it. Okay. Let, let's talk about when you start to get traction with Vimcal or, or kind of, at least I would say, recognition. I know you, you got some early success. There was a lot of buzz around the, the product and then things kind of didn't quite go to plan. And we'll talk about that in a second, but, Just tell me about like what kind of buzz were you getting?

What, you know, press coverage? What was it like, how, how did, how was the word getting out about Vimcal?

[00:24:20] John: We were getting a lot of buzz on Twitter, which is kind of the red-hot core of our ICP. So at the time, again, we were targeting founders, VCs, basically decision makers in the tech space, in the startup role.

And a lot of people that we respected were retweeting us, were trying out Vimcal, a lot of the founders that we looked up to, and a lot of them were asking us to invest and did end up coming onto our cap table. So for I would say about a year, year and a half, we had a lot of buzz on Twitter. And one thing that I wish we would've done is to try to.

Extract that and get buzz elsewhere. So you mentioned pr. We didn't have as much PR coverage at the time, but that is definitely something I should have jumped on, for example, looking back.

[00:25:07] Omer: So you, you get this kind of, this buzz vimal is kind of this hot thing and I think that was kind of, you know, for, for a couple of years. And then what happened?

[00:25:18] John: And then we open up the app to everyone. Everyone can join no wait list. And surprisingly, when we thought that would actually make us scale faster, that is when demand started to grow more slowly. And it never really flatlined, but it was just a lot slower than before. We, we just weren't used to it.

Right? Because we came off the gate and there was just always more demand than we could handle. There were always more people on the wait list than we could onboard. And when we Yeah, came out with the self-serve, that that changed. At the time, more calendar startups came out as well, so we were no longer just the only player in the field.

While that didn't affect us too much, I think the combination of everything and us not, not extracting our buzz and leveraging it in on other platforms like press or you know, outside of Twitter that made. A six to eight-month period last year, pretty difficult where we were just adjusting to not being the, that the new, new kid on campus.

Right. The, the really exciting one, and we had to do a lot to really overcome that. One thing we did well looking back was we shipped really fast. We would just ship left and right. We said every two weeks something needs to come out. We would also ship both small things and big things. So we shipped our iOS app, our Outlook integration, all I think in one day we got some press coverage.

We learned the lesson, got a TechCrunch feature. And then at the same time I also started writing more online, just sharing our story, sharing all the hard parts, the fun parts of doing Vimal, both on Twitter and LinkedIn. Again, going to another platform just so we're not, you know, eggs all in one basket.

And. I would say that as of now, we have gone back to a place where we're more familiar with, which is more buzz, more excitement, and I do not ever want to lose that. I wanna make sure that we always have at least a few growth experiments going at all times. And getting to that point, you know, the riding, the shipping fast wasn't the only thing we tried.

We tried like four other things, they failed. We shut 'em down. It's okay. We learned from them. I think the most important thing, or one of the most important things for a founder and a CEO to do is to build momentum and keep that train going nonstop.

[00:27:45] Omer: So you, you said it was pretty difficult in those eight months when demand was slowing down.

Gi gimme an example of, you know, how difficult. We weren't there. What was going through your head? What? What were you struggling with?

[00:27:59] John: I remember on my 30th birthday, which was about a year ago, I spent my entire 30th birthday talking to Mike, my co-founder, and we were talking about contingency planning.

You know, we weren't in trouble financially, we weren't like getting close to death, but we were like, oh, what if this keeps going? And you know, Should we look to maybe sell, go do another job? Should we pivot? We didn't really consider pivoting cuz Vimcal is doing, you know, great and we have real users. But every now and then, because we came close to death, so many times we will do contingency planning even if it's not serious.

But I just remember that was supposed to be a very lighthearted happy day cuz it was my 30th birthday and it was just brutal. I just remember like the room was dark. We were on slack huddle and I was just laying there looking out, like talking to him. And sometimes we'd just be quiet for like 20 minutes and, and then talk about another thing we could do.

And yeah, I mean those are the days. Sometimes it looks like you're crushing it outside and then. Behind the scenes, you know, it's, it's pretty tough. But funny enough, the hard, that was the beginning of that really hard stretch of six to eight months, and I would say probably last fall is one thing, started getting better.

But yeah, you, you just gotta push through. It's, it's never, it's never easy.

[00:29:19] Omer: Yeah, totally. So what was the lesson here? Because it happened around the time you went from waitlist to opening it up to everybody and going self-serve. It sounded like a great idea because now the floodgates are open.

Everybody can come in and you know, it's gonna be all goodness. Didn't quite work out like that. What was the lesson, cuz I mean, you, you, you are now self-serve again. There's no waitlist anymore to, to try Vimcal. What, what was the, the lesson there? What do you think you could have done differently? Or if someone's kind of going through that now, like what's, what's the lesson here that kind of, to avoid that painful period or you know, that situation that you guys ended up in?

[00:30:04] John: Yeah. This is very specific to us, but we did two things on the same day. We launched that day, so the launch was successful. We got number one product of the month on product Hunt. It was great. We got a lot of installs. But we not only opened up self-serve, we opened up access at the same time. So that, that's two separate things.

So before we were forcing you on a waitlist, and once you're off that waitlist, we were forcing you to do a 30-minute call. Every single person, no exceptions, whether you're our friend or my mom or dad, doesn't matter. And after that, not only did we let you not have to wait on a waitlist, but you could just sign up and start using the product yourself without a 30-minute call.

What I would've done differently in our own situation is either still enforce the 30-minute calls or just let anyone sign up, which you know, is probably not a great option cuz you just get a, a lot of no shows and back calls, or you keep the waitlist. But the people that join can now do it without a 30-minute call.

And looking back, we should have done that so that at least we could taper up the open access instead of all at once. Everyone can join anytime without ever having to talk to us. And so that was really painful, but we felt the pain probably like three months later. But one thing we did was that we added points in the onboarding flow to ask you to book a 30-minute call.

We are really good at those calls if you get on a call with us. Our team can probably win you over and you'll be a Vimcal lifer. But the problem was right after we launched, we just said, okay, let's maybe not do as many calls anymore. So nowhere in the onboarding could you book a 30 minute call. And that just, I would say, sucked the oxygen out of the room for us.

[00:31:53] Omer: Yeah. Yeah. That's good. Listen, I mean, because like the 30-minute call is like a big overhead. It's not like, You know, you are, you are closing a, a customer that's gonna pay you five, $10,000 a year. Right? It's like $15 a month. And, and so doing that is hard. But the, the danger with it, if you, if you don't do it and the, the self-serve or the, you haven't got the, the product led growth kind of pieces totally figured out.

On the onboarding there is that someone who might get on a Zoom call with you within 30 minutes, understand how to use the product properly and start getting value from it immediately may go through on this different path where they spend a lot less time trying to figure out the product. Don't totally get it.

And then lose interest or say, ah, this is not for me. Right? And so that's, that's the thing you have to deal with, right?

[00:32:52] John: No, that, that's exactly it. Once they get on a call, they're there for 30 minutes. No one's just gonna get on it. Ah, actually I don't wanna do this anymore. Right? That's never happened. But if they just log into your app and for some reason you don't cash your attention within two seconds, they're gone.

They might not have, you know, even given it a fair shot, but that doesn't matter. That's up to you to capture their attention. And so we actually design everything in Vimcal. Whether it's our onboarding calls or our self-serve onboarding around one magic moment. We call it the magic moment or the aha moment.

And this is something we did from day one and our magic moment is when a user uses slots for the first time, where they just drag at the times, copy paste into their email and once that happens, anything you tell 'em after is amazing, like just something flipped in their brain. So, In our self-serve onboarding.

We also try to have that as early as possible on our website. You'll see a jiff of that on our Twitter pin at the top is that gif. So one thing I like to talk to other founders about when you know we share notes is find your magic moment, capture it and bring it as early as possible into the process.

So a lot of people find out about what makes Vimcal before they ever even go to our website if they're just on Twitter.

[00:34:15] Omer: Yeah. Yeah. Great point. Because I think I. Sometimes what I see is somebody does a demo and they, they show you all the kind of fundamental stuff first. The, the, I guess the thinking being, well, you gotta understand the, the basics first before you can get onto the advanced stuff.

But the danger is the longer you do that, people do tune out because it's like, you know, you are thinking, you're educating me to kind of get to a baseline and I'm thinking the. This sounds like every other product I've used, this is not for me. This is not for me. Right. And so this idea of like bringing in something like that as early as possible, kind of completely, like it flips the switch.

People are like, ah, I'm paying attention now. This is something different. This is something better. This is something relevant.

[00:34:59] John: Yeah, exactly. We have four step framework actually to building the perfect onboarding call. So a little caveat to what I said earlier about having as early as possible within the call, there's actually a first step before you get to the AHA moment, which is, we call it kinda like teaser.

We'll show you a few things here and there are maybe 30 seconds here, 30 seconds there to just get you excited, amp you up, and so we can think of getting the momentum level up. And then we hit you with the magic moment. And then it's just top future number 1, 2, 3 after that. And. Their minds are just being blown left and right.

We show 'em slots with time travel. We show you how you can just type all the details with natural language to create an event. And then we show 'em a few other things and by minute 20 of 30 of the call, again, like I said, anything you show them is like magic. And at that point, Part three. We show 'em a few things to kind of wind down and then lead to part four, which is the close.

And we always make sure that we close on the call. And it, when we followed that framework we were able to again, convert 70% of all our calls to pay users.

[00:36:06] Omer: So you said they were four steps to the onboarding. What, can you just summarize what they are?

[00:36:10] John: It's the teaser. So that's usually we show 'em a few cool keyboard shortcuts.

People really like that. Number two is the aha moment. And then number three is we call it milking the aha moment. So it's the second and third best feature usually. And then number four is the close. It's a subscription, whatever your CTA is, whatever you want them to do.

[00:36:32] Omer: So I know there's this built-in virality into the product that also helps you acquire like a, a big number of your customers are coming in through that, that virality.

Is that through the, the scheduling piece when people are kind of sharing availability or whatever.

[00:36:49] John: It, it's, it's a few pieces. So one of the major pieces is through the booking links. The advantage of having a calendar is that the calendar is inherently social and inherently viral. If you think about a calendar invite, you have people from multiple companies in one place online with one link.

It's kind of like the lobby to a conference room, right? That's what the counter invite is. And so when you send out a booking link, when a Vimcal user sends out a booking link, they're doing marketing on our behalf basically by asking someone else to book with a Vimcal booking link. And there's another way where we also get a lot of users organically, and that's through referrals.

We have a pretty, I would say, active referral system because of our onboarding calls. Early on, we kind of built a referral system. According to that. So one thing we learned is, you know, once people get to the end of the call, they're super ecstatic. There's actually a half-life of excitement after that about your product.

So for the first day, you can ask them, Hey, do you mind sharing this with a couple friends? Or do you mind tweeting about Vimcal? If you really like it, you know, if you're okay with it. And they'll be, yeah, of course. I love this owner. Show everyone I, you know, it's, it's crazy. And then three days after that, you know, they're still really excited.

Maybe they'll send out emails saying, Hey my friend wants to use it. Or Here, here's a referral, or here's a piece of feedback. And then by day seven, it's a little less than that by day 14. And then after a while it evens out and. If you can capture them early on and get 'em really excited, there will be a point where they plateau and they're still in love with the product, but you know, they're back to their day-to-day lives.

And so our goal is to get 'em to refer as early as possible after the first time they used Vimcal.

[00:38:36] Omer: Hiring. So what did you say the size of the team was?

[00:38:39] John: Nine people.

[00:38:40] Omer: Tell. Tell me about your experience with hiring friends. That was an interesting thing you told me earlier. You get mixed advice on whether you should hire friends.

[00:38:48] John: I think the key differentiator, which I screwed up royally, is only hire friends without, you know, a full interview process and all if you've actually worked with them before. We made the mistake of hiring some friends, some family friends without a due interview process because we knew they were smart, we knew they were capable.

They've worked at startups. We should have done our due diligence of whether they would work well in our startup. And that was a very painful process with multiple friends that you know it, it didn't work out for one reason or another. And it kind of affected our relationships for a while. But now, now we're okay, but looking back, yeah.

Hire your friends quickly if you've worked with them before and you know that you work well together. And then if you know they're smart, but you have not worked together in close capacity, full interview, regardless of how close you're with them.

[00:39:49] Omer: Well gimme an example of the kind of problems you had to deal with?

[00:39:52] John: Yeah. So one one family friend had a really good pedigree but it just turned out that their tempo. Wasn't really the same as ours we're a startup. We're very fast moving. There's not, there were, there was very little, you know, documentation or processes very early on, and they had come from a more big company experience.

With some startup experience, so I thought, oh, it was okay. But I think their temple was more tied to their big company experience, which I did not realize. Just cuz you've worked at a startup does not mean that is your default speed and timeline.

[00:40:27] Omer: Yeah, I mean, hiring is a whole, we could do a whole episode on that in terms of, you know, hiring.

There's a certain type of person you wanna hire every stage. Ideally, in an ideal world, you want people who can continue to grow and evolve with you as the company grows. But yeah, don't hire family friends without interviewing them. Big takeaway. So we're gonna get into the lightning round but before we do that, just one quick question about, you talked about the second app maestro for, for eaas and, and Chief of staffs and stuff like that.

Do, does the person who. I'm an EA and I'm, I wanna use Mystro. Does the person that I work for have to be using Vimcal as well?

[00:41:07] John: Nope. Yeah, that was a very explicit decision, something we debated a lot internally. But we figured that busy executives actually don't really use their calendar. They only re use it as a read only.

Like, oh, when is my next meeting? So because of that, we don't want the added friction of also having them on Maestro, if their EA uses it.

[00:41:27] Omer: So that sounds great. But it also sounds like more of a headache for you because you've now got two products, two ICPs, two potential messages in terms of your marketing.

Do you guys have a plan there?

[00:41:39] John: Yes. This is actually a lot more of a synergy than it looks from the outside. We have had founders who. Use Vimal when they're like a two, three-person team and then their company grows and grows over the years and now they're Series C, D, CEO and they have an ea. So overnight they go from scheduling all their emails and you know, being a power counter user to basically not using the calendar anymore other than to join meetings and seeing the rest of their day.

So we wanted to have a continuation for these types of users. We also saw early on when we were doing the onboarding calls that EAs were direly in need of a calendar solution, but no one was building for them. EAs don't get any love, just like Outlook. Users don't get any love from software developers.

It's always GSuite first, or like people built for engineers and other people. Right. So you've never heard of an app for an ea? So there's just this gap in the market. But the funny thing is, from the calls, we talked to so many EA and the Vimal product was actually only three or four features away from being a full-fledged EA product.

We just did not have time to prioritize it, so we just put in the backlog for two years. But the great thing about my show is anything we build for regular m L users, it's also useful for EA and vice versa. If we can build something for the most intense use case, which calendar use case, which is the ea.

Scheduling for multiple executives, then we can easily build something for like product manager or an engineer, right? So we are actually taking on like a harder challenge, and if we can do the hard thing, then the rest is a lot easier. So the messaging, the feature work is actually almost one-to-one between the two, and they share 90% of the same code base.

[00:43:38] Omer: All right, so let's go into the lightning round. I've got seven quick-fire questions for you. Just try to answer them as quickly as you can.

What's one of the best pieces of business advice you've received?

[00:43:47] John: When we were going through YC, I remember a talk by Michael Sebel and Amy, who was the program director, and they were talking about co-founder problems, and they said, Usually with two co-founders, you have this interesting dynamic when you disagree and when you argue is that one person is kind of warmer, one person's colder, and one person will lean towards the other and try to reach out when things are going wrong, and the other will kind of shy away.

And I remember while listening to that, sitting next to my co-founder, we were arguing a lot at the time. We just looked at each other. We were still mad at each other. We just looked at each other and like just started laughing because I just spoke so truly to us, he was the warmer one. He was the one that if things you know, went wrong, he wanted to like approach and talk about.

And I was the one that was kind of like cold and would just like go off into my own space. So, This is advice you get all the time, but the founder relationship is the most important thing. Nothing else matters if you two aren't okay.

[00:44:43] Omer: What book would you recommend to our audience and why?

[00:44:46] John: Animal Farm?

It's a short read and it's one of my favorite books and shows how an organization can deteriorate over time.

[00:44:52] Omer: I don't think I've ever had that 350 plus episodes. That's a great book. What's one attributal characteristic in your mind of a successful founder?

[00:45:01] John: One attribute that I think is more and more important today, and I'm just starting to feel the benefit of it now, is being able to write well and communicate well in the written word.

[00:45:10] Omer: What's your favorite personal productivity tool or habit?

[00:45:14] John: Favorite habit is the one thing by Gary Keller, which is do the one thing that makes everything else either easier or obsolete.

[00:45:21] Omer: What's a new or crazy business idea you'd love to pursue if you had the extra time?

[00:45:24] John: This is a great idea my friend is pursuing, it's audio enabled resumes and audio enabled ats. A lot of recruiters have to do a lot of phone screens that just end up being really bad because they see a good resume, get on the call, they're not happy. So having candidates just fill out, tell me about yourself. Why do you wanna work at a company? And these very generic phone screening questions with audio allows 'em to basically sift better through resumes.

[00:45:51] Omer: What's an interesting or fun fact about you that most people don't know?

[00:45:55] John: My first language is French and my third language is English.

[00:45:58] Omer: Wow. And finally, what's one of your most important passions outside of your work?

[00:46:02] John: I try to learn one thing really well every year. Last year it was Spanish. I got to onversational and this year is chess. I'm just playing like two, three hours a day, which I need to calm down from it a little bit, but I love it.

[00:46:16] Omer: Awesome. Cool. Well, thanks for joining me, man. It's been a pleasure chatting and, and kind of unpacking the story of Vimcal and, and what you guys have been doing over the the last few years.

If people want to check out Vimcal themselves, they can go to And if folks wanna get in touch with you, what's the best way for them to do that?

[00:46:35] John: Yeah, they can find me on Twitter. My handle is jaylbird11 and JohnLi611 at LinkedIn.

[00:46:45] Omer: Okay. We'll include links in the show notes to, to those.

Great. Thanks John. It's been a pleasure and I wish you and the team the best of success.

[00:46:54] John: Awesome. Thanks for having me. Take care.

[00:46:56] Omer: My pleasure. Cheers.

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