The following interview is a conversation we had with John Li, Co-Founder and CEO of Vimcal, on our podcast Category Visionaries. You can view the full episode here: $7 Million Raised to Build the Future of Calendar Productivity

Brett
Hey, everyone, and welcome back to category visionaries. Today we’re speaking with John Li, Co-Founder & CEO of Vimcal, a calendar productivity tool that’s raised 7 million in funding. John, what’s going on today?

John Li
Hey, Brett, good to be here.

Brett
Yeah, super excited to have you here. And I’d love to begin with just a quick summary of who you are and a bit more about your background.

John Li
Yeah, I’m the Co-Founder & CEO of Vimcal. Vimcal, I like to tell people, is like your calendar on steroids. So it’s designed for super busy people and their teams. Most of our users, if you look at their calendar, it’s basically like a giant block of color from morning to night. These are people that schedule a lot of meetings, both internal and external. And for them, they just need a more powerful calendar to get through their workday. And so we’ve been catering to really busy people like founders, VC’s business owners, and it’s spread throughout their organizations. And about a year ago, we launched a second product, which is called Vimcal EA. Vimcal EA is exactly what it sounds like. It’s Vimcal, but designed for executive assistants who we see as the Navy Seals of calendar users.

John Li
So we’re really designed for the more premium, more complex scheduling cases.

Brett
What’s the genesis of the story? Take us back to the early days.

John Li
Yeah, the early days. We did not start out as a calendar company. My co-founder, Mike and I, we actually started working on nights and weekends on an augmented reality company. And that was back in 2017 when we started, I want to say, and we did that for about nine months. We eventually got into YC and decided to pursue it full time, basically mid batch. We decided that we had to pivot because it was just way too early for augmented reality. And so we pivoted to a fitness company and graduated YC and did all of demo Day and fundraising with a fitness company. The genesis for the idea for Vimcal really came from that fundraising period I was talking to over a three month period, hundreds of investors, because after YC Demo Day is pretty crazy.

John Li
And I remember at one point, there was one week where I had 30 investor calls to schedule, and I just completely fumbled a bunch of meetings, and I was double booking meetings with investors. I was booking meetings in the middle of the night because one person was in Asia, and it was just always this, I guess, slight annoyance in the back of our minds that just scheduling investor meetings particularly, was very difficult. And so if you think about scheduling meetings, you really have one of two choices. You either do it yourself and do all the time zone conversions yourself. You send out and write out the times yourself, or you send something like a calendly link or a booking link.

John Li
Now, when you’re meeting with someone and asking them for hundreds of thousands of dollars, you don’t want to risk potentially offending someone by giving them a calendar link and saying, hey, schedule a time on my calendar. So I decided to do it manually. And, yeah, at the time, we didn’t think that this would become an actual company. We kept working on the fitness company for, I would say, almost a year after that, and then we pivoted a second time when that company wasn’t going anywhere. And that’s when we actually decided to build out a full calendar because of the pain point we felt a year prior.

Brett
I’ve experienced that pain myself, and I experience it anytime I go rogue and try to, like, schedule a meeting or book something without my assistant, somehow I get it wrong. Like, every time, like, I screw up the time zones or I forget to include someone. It’s so funny that something that on paper sounds so simple is so difficult. I talked about that with friends. Like, they all have that same problem too. It’s like founders are just, like, incapable of, like, doing what it takes to, like, book things and coordinate all these different time zones.
John Li
It seems it takes a surprising amount of concentration to get a meeting book correctly on your calendar. That’s correct. That’s insane.

Brett
At what point did you start to feel like there was solid traction?

John Li
Yeah, when we first launched, it was January of 2020. We actually only had a month and a half of Runway left. So I think we launched in January. We were about to hit zero in the bank by March. And I just remember when we first launched, we forced everyone to do a 30 minutes call with me to use the product. And that’s not because we wanted to. I mean, partially because we wanted to talk to our users, but also partially is because we ran out of time to talk to build out a payment flow inside the product. So I had to be the one collecting credit cards at the end of each onboarding call. And I just remember, even in the early calls, we launched in the founder community and the YC community. So it was a lot of YC founders.

John Li
And even in the early calls, there was a lot of positive sentiment, even though our app was buggy. But it was mainly because we had one feature that people really like. So that feature is called slots. It’s where you can drag times on your calendar, and we’ll type it out for you to copy and paste. And it’s very simple, very bare bones at the time. But that one thing was what kept people coming back to use Vincal and what caused people to want to pay for it. So even though the app was buggy, it was crashing left and right. People were willing to pay $15 a month just to use that one feature. And we really honed in on that aha moment. And I guess that was the first small signal of traction we had.

Brett
So what was that like? You’re almost running out of cash. You launched this new product, and then Covid hits.

John Li
What’s that like for you, bittersweets? Because at the time, were so stressed, we decided to pivot to vimcal seven months prior to that, and we thought we would get an MVP out in 30 days. But things always take longer than you think, and the counter is surprisingly difficult to build. I always say that building a good counter itself is a moat because it’s just very difficult. Even if you have a 30, 5100 person team, it’s not guaranteed that you’re going to build a good calendar. And so were really stressed, to be frank, leading up to the launch, and I remember we had an office hour with one of our YC partners, and were just telling, hey, we have this much money left in the bank. This is our idea. We’re going to launch and see how it goes.

John Li
Is there anything else we can do? Should we fundraise? I think all three of us just decided that you should just launch and see what happens. And worst case scenario, you go back to applying for jobs. And so we kind of launched with nothing to lose, and Covid hit, I think, like four or five weeks after that, if I’m doing the math correctly. And I say bittersweet, because it was tough at the time for us and the entire world, but also, out of nowhere, people started looking for remote work tools, and so we just caught a really good wave, like very lucky, right? That’s not because of what we did. And so we launched pretty quickly. Our waitlist just started filling up super quickly. And were also the only calendar startup that really came out in the last like five years at the time.

John Li
If you think of 2000 to now, the last few years, there’s been a ton of counter startups and scheduling startups come out and like, were really the first ones in that wave. And I think just that plus the remote tool need, I think we just caught a lucky timing.

Brett
What’s the approach to marketing look like?

John Li
Absolutely, we focused really hard on our icps, and early on that was the founder, the VC, the business owner, basically leaders within an earlier stage company, SMB, I would say. So a lot of our marketing was geared towards that. In the early days, like I mentioned, we onboarded every new user over a 30 minutes zoom. And we actually did that for two years. We were basically in beta for almost two years and were very strict about who we let off the waitlist. So we had tens of thousands of people on the waitlist. And the criteria was that you’re either a founder investor or I. You had a lot of external meetings and then a lot of our marketing early days was just trying to get champions and trying to get champions to spread the word about Vimcal via Twitter.

John Li
And since then we’ve done a lot more PlG because tool like Vimcal, that’s a scheduling tool, has the benefit of having booking links. So actually when your users schedule with other people, they’re advertising on your behalf.

Brett
Right.

John Li
You’ve seen that kind of growth with counties of the world.

Brett
Was the ICP obvious from the start then, that you were going to sell to founders initially, or founders and investors, or what was that process like to identify that ICP as the market you wanted to go after?

John Li
Yeah, I think the thing we did differently with Vimcal than with two other companies was that it was the only product that we built for ourselves. So I don’t know if we actually sat there and said, okay, we want to target founders, but that was basically the only audience had access to launch to. And were founders ourselves. So were building everything that we wanted in a calendar. And that made it a lot easier than building the fitness company or the augmented reality company because weren’t end users. And so early on we just started with the founders because it was us. And then we found out really quickly that on the other side of scheduling for founders is the investor who’s receiving it. And they also schedule a lot of the similar types of meetings.

John Li
And we told ourselves early on that our goal was to get basically everyone at YC Demo Day or one of the other incubator demo days for both sides of the fundraising process to be scheduling with each other using ViM count links. So basically imagine Vimcounx bouncing between founders and investors.

Brett
Makes sense. Why do you think the calendar space has been so sleepy? Why was there no innovation? Why were there no new startups coming out?

John Li
I think at the time, Microsoft and Google were just so dominant and I think we had just come off a wave where mobile apps were really popular. So a lot of founders were, for the decade before, were just really focused on mobile app. But something like a calendar, you can only get a partial experience on mobile, whereas the meat on the bone is really on the desktop experience. Right. If you think about your mobile calendar, it’s mostly a read only device and you’re basically looking at it to see what’s coming up or maybe to join a call really quickly. I think it’s that. Plus I think there’s just this sentiment that there is an upper bound to how big a calendar company can get. The prior largest acquisition was Sunrise calendar, which is the darling calendar of Web 1.0.

John Li
And because it was basically just that in calendly, I don’t think there seemed to be a lot of obvious opportunity for founders to start a counter company. And I think fast forward to now. It seems kind of obvious looking back, but at the time it’s been a drought for I would say like six years. And even Google calendar, when we started, we heard that there wasn’t a team actively developing on it. Like they just, the problem is solved and they’re just maintaining it for like three, four years without an active dev team.

Brett
Was sunrise the one that got acquired and they just shut it down? Because I think I was a user of that and I actually liked the product and then I can’t remember who bought them, but I remember, like, I think they closed it down immediately after that. Right?

John Li
Yeah, Microsoft bought them. I think they paid a lot to basically get their design team and they integrated parts of Sunrise counter into the outlook counter, is what I heard.

Brett
This show is brought to you by Front Lines Media podcast production studio that helps B2B founders launch, manage and grow their own podcast. Now if you’re a founder, you may be thinking, I don’t have time to host a podcast. I’ve got a company to build a.

Brett
Well, that’s exactly what we built our service to do.

Brett
You show up and host and we handle literally everything else. To set up a call. To discuss launching your own podcast, visit Front Lines IO slash podcast. Now back today’s episode.

Brett
Got it. Makes sense. So I’m a big suits fan. I’ve watched suits like probably how many times I’ve watched that show, but I’ve.

John Li
Watched it a lot. I love it.

Brett
I see you had some good marketing there with Donna from suits.

John Li
Talk to us about that. Oh, yeah. This is probably the most fun campaign we’ve run. So we just launched a campaign with Sarah Rafferty, who plays Donna on suits. We worked with her through cameo. She shot a video basically expressing her gratitude for all the eas around the world and the admins. And now that we have a product for executive assistants, we want to do a lot to lift eas and make them feel more appreciated. Eas are often underappreciated, overworked, underpaid, but they are total badasses. And so we ran a campaign this past week for admin appreciation day, or admin Professionals Day, which is April 24 this year. And we basically had, quote unquote, Donna send out a thank you note to all the EAS worldwide.

John Li
And also as a reminder to the executives, the HR teams, to plan something nice for their eas on April 24.

Brett
That’s so awesome. That’s such good marketing. Anyone who watches suits must have been so happy and excited.

John Li
Oh, yeah. And the funny thing is, it was three others on the team working on this campaign with me, and I’m the only one who’s seen suits and none of them washed suits. So they’re just like, all right, are you sure this is going to work? Because they didn’t understand like the cultural side guy stuff. Don. Alright. She is two years. She is like the epitome in Hollywood. Yeah, it’s just really fun. They’re all like skeptical, but we push it out. We’ve had hundreds of eas shared within the first 24 hours. So far it’s been really good.

Brett
Yeah, it’s such a smart idea. I love the campaign. Have you done any other campaigns like that?

John Li
Not so far for the EA side, just because, like I said, it’s pretty new. But we do have more fun campaigns coming out. We haven’t seen much marketing specifically for east, so we definitely want to change that and become one of the more, I would say, like, larger providers for EAs in the space.

Brett
Talk to us about that decision then, to launch a dedicated product for ease.

John Li
Yeah, everything cycles back to talking to your users. So early on when were trying to figure out our different icps, we had a few hypotheses, so the ones I mentioned earlier, and we also thought maybe salespeople, maybe recruiters, because they schedule a lot of meetings. And then one that were surprised by, but not so much in hindsight, was the executive assistant. Executive assistants live in their calendar. They spend 70% of their day in the calendar, yet there is nothing built just for them. There’s no EA tool. All the scheduling tools on the market are built for scheduling for yourself, for personal scheduling, not for delegated scheduling, which is a whole nother beast.

John Li
And so EA spends so much time just like manually copying and pasting zoom links and copying pasting just things in and out of the calendar, because again, everything that they use is geared towards their own account, even though they’re scheduling for three or five execs. And there was just so much friction, so much wasted time using these tools. And so we always knew in the back of our minds that we would build something specifically for executive assistants. It was just a matter of timing because were a small team. And so the EA product was actually in beta for over a year as we tested slowly. But we just weren’t ready yet to actually launch. And so we finally launched a year ago and we’re really building vertical SaaS for EAS and just going into a new category.

John Li
So a lot of our go to market this year is focused entirely on the EA market.

Brett
How do you even reach EAs? Unlike, you know, it’s like cyber security or if you’re targeting founders, like, it’s pretty easy to figure out what news they read, what podcasts they listen to for EA. Like is there an eanews.com dot? Like where do they get your information from? Like are there communities? All that?

John Li
Yeah, there are communities. The great thing is that there are a lot of great leaders in the EA space. So eas who’ve done amazing things and then gone off to have their own communities newsletters. But we do see that the EA market is kind of fragmented. And there isn’t one source of truth why c is to startups. There isn’t that in the east. And even within companies, eas are these Lone islands. A lot of their work can be pretty lonely because it’s them supporting multiple execs and they often do work with other eas, but every is supporting someone different. So the vast majority of the day they’re just on their own. So because of that, we want to do a lot to not only bring them together, but also build our own community, our own resources over time for years.

Brett
If you think about your 2024 priorities, what do those look like?

John Li
Absolutely two things. One is really flushing out the EA product, and at this point it’s basically been out for two years, if you count the one year of it being beta. So it’s already at maturity, but just reaching more eas and having more features that save them even more time, I would say that’s priority number one. And priority number two is building out more team features. Scheduling is a group activity, and the more people that are being scheduled for on a meeting, the more complex it gets, because now you’re dealing with more calendars and more calendars that those calendars touch. So as the number of people in a meeting grows linearly, the complexity of a meeting being scheduled grows exponentially.

John Li
And so team and multiplayer features, both for the vimcal product and the EA product, and then just having a more robust EA product in general as you.

Brett
Think ahead for 2024 or just what’s going on this year, like what’s keeping you up at night, what are you worried about?

John Li
That’s a great question. I think right now there aren’t many software solutions for EAS, but we’re seeing more pop up. And so having lived through a very competitive space in the counter space where after we launched, just a bunch of new startups with product that looked very similar to ours came out. I don’t want that to happen again. So I think we’re just kind of racing ourselves to be that de facto tool before someone else beats us to the punch.

Brett
As I mentioned there in the intro, you raised 7 million to date. What have you learned about fundraising throughout this journey?

John Li
Yeah, I fundraise our pre seed in 2020 slash 2021 when the market was much better. And then I fundraised again for our seed round in 2023, which was completely dried up, if you remember. I would say the main things that really helped in the pre seed was having a really good demo. So because I was doing the personal onboardings early on in 2020 and 2021, a lot of times I’ll get an investor on the call who wants to use Vimcal, whether it was a fundraising call or customer onboarding, I always started with the demo. I always show them the product, because once you show them the product and they like it’s a completely different fundraising conversation afterwards because they get it right. And so that’s my advice for pre seed, for seed rounds.

John Li
And I guess like beyond, I would say one know the main reasons that an investor will say no to you are and be very honest about them and have really good answers to mitigate that. So, for example, one reason we kept getting for rejections early on in the seed run was that a lot of investors thought a counter company couldnt become a unicorn because you have a Googles and the Microsofts of the world. And so I had to be very clear that in our minds and with our goals, Vimcal is not a counter company. But were a meetings company, we help you schedule meetings, well, help you manage meetings. So we’re more of a comparison with like the counties and the zooms of the world than the Google calendars or the output calendars.

John Li
I think halfway through fundraising, once I made that distinction, the meetings became very different, the sentiment was very different. And so I would say that’s my number one piece of advice. And then the number two piece of advice would be try to get a lot of traction and growth for the two or three months leading up to the fundraise. You want to fundraise off of momentum. You don’t want to say, oh, we’re going to grow in the next six months, right? You’re going to say, hey, look at our p and L, the numbers are up, so you better not miss out because someone else is going to want it.

John Li
And I would say, really focusing on the growth numbers leading up to fundraising and just mitigating the reasons you get rejected are the top two things that helped us get through eleven months of fundraising in 2023.

Brett
If you think ahead for your series A, what’s top of mind?

John Li
Yeah, well, as a company in general, we would like to become profitable within the next year, and I do think that’s possible. And I like to subscribe to the advice we got in YC, which is treat every round as your last. And I do think that with a PLG product like Vimcal, a viral product like Vimcal, you don’t necessarily need the type of funding that venture gives you to become a unicorn. I would say the series a is more like our plan B or plan C. We’re really focused on growing quickly, organically, and through the product to become profitable.

Brett
What else did you learn from YC? What were some of those other big takeaways?

John Li
I remember one talk that one of the, I think partners and the program coordinator at the time gave us was about founder relationships, and they were just telling us that most companies die by suicide, not by murder. Basically, like the founders split up is how most companies die. And they were mentioning that most founder arguments usually actually go this very specific way, which is one founder is more warm, one founder is more cold when you disagree on something. And so the one that’s more warm will kind of lean in and be like, hey, I need this from you, or I want to talk about this. Let’s get through it. And the one that’s like, more cold tends to lean away or they need some space. Right. And it’s more.

John Li
So the style of disagreement between the two, that causes a lot of the issues more so than the issue itself a lot of times. So once we identified that between Mike and I, it actually made disagreements a lot easier to go through. And that plus executive coaching, like, really helped us a lot. So I just remember when we started Vimcal, we shook hands and we’re like, no matter what happens to, we’re going to be friends at the end of this.

Brett
That’s awesome. Final question for you. Let’s zoom out. Three to five years into the future, what’s the big picture vision look like?

John Li
Yeah, I would say we’ve gotten really good traction in the early stage ecosystem. So again, startups, nvcs, and looking for three to five years, especially with our EA product, we really want to go big upmarket, so we’re building out a sales team now. The EA product is our wedge into large organizations. We want eas to first use East Fortune 500, government agencies, et cetera, to use Vimcal EA. And then because of the nature of group scheduling, it will propagate throughout the companies. So, yeah, in three years, I would love Vimcal to be at the majority of Fortune 500 companies.

Brett
Amazing. Love the vision. All right, John, we’re up on time. We’re going to have to wrap before we do, if there’s any founders listening in that either want to get in touch or want to follow along with your journey or want to test the product, where should they go?

John Li
Yeah, I’m pretty active on Twitter and LinkedIn so they can show me a DM.

Brett
Awesome. Thanks so much for taking the time.

John Li
Thank you so much, Brett. Had fun.

Brett
This episode of category Visionaries is brought to you by Front Lines Media, Silicon Valley’s leading podcast production studio. If you’re a B2B founder looking for help launching and growing your own podcast, visit Front Lines IO podcast. And for the latest episode, search for category visionaries on your podcast platform of choice. Thanks for listening, and we’ll catch you on the next episode.