Vimcal and John Li

Calendar software was not what John Li and his co-founder Mike Zhao set out to build when they left jobs to start a company in 2017. They originally set out to build a product in the augmented reality (AR) space. They were accepted into the Y Combinator (YC) accelerator program in 2018 with their AR idea. However, halfway through YC, their AR idea was not working and so they decided to throw everything out and start over with a fitness product. They graduated from YC, raised $200k and then limped along for another year. Close to running out of money they realized they needed to start with a fresh new idea. Another pivot.

As they brainstormed startup ideas, with a dwindling bank account, John remembered all of the challenges coordinating schedules with investors he’d had when fundraising in 2018. They decided that was a problem that needed to be solved and that no one was focused on it. 

After six months of building the first version, they launched their closed beta of Vimcal in January 2020. The pandemic accelerated remote work and their waitlist grew quickly. A little over a year ago, in October 2021, they publicly launched on Product Hunt to a great reception, earning the top spot of “Product of the Month”.

I connected with John last month while I was on parental leave. I had been playing around with Vimcal and thoroughly enjoying it for a few weeks. But I had been using Calendly to schedule calls for One Year Wiser. I switched to Vimcal because of its better design and more robust feature set. I especially like being able to easily share proposed time slots with people. I was excited to talk with John roughly a year after their public launch to hear how it’s been going.

In our conversation, John talks about:

• How they came up with the idea for Vimcal after pivoting their startup multiple times, including halfway through the Y Combinator accelerator
• How a $5k check from a prospective customer saved Vimcal
• The benefits of their closed beta approach in which he did thousands of 1:1 onboarding calls
• How their 50/75/100 method has improved his team’s design and engineering velocity
• The importance of disproving your product as quickly as possible and not letting your product become your identity

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My questions are in bold; this interview has been lightly edited for clarity.

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Let’s start with the origin story of Vimcal. If I read correctly, you were in Y Combinator focused on a different idea and ended up pivoting to Vimcal. How did Vimcal come about?

John Li: Yeah, I can start all the way at the beginning. My co-founder, Mike and I, have been working together since 2011, when we met in college at Berkeley. We had some computer science and electrical engineering classes together, and we got along so well that we ended up scheduling all of our classes every semester together so that we could be project partners. After college, we decided to hack on things on nights and weekends, and that led us to start our first company in 2017, which was in the augmented reality space.

We applied to Y Combinator and were accepted in 2018, but about halfway through the program we pivoted from augmented reality to fitness – completely different. A year later we pivoted again to Vimcal.

The idea for Vimcal came out of a problem I was encountering when I was raising money for the fitness company. After YC’s Demo Day founders typically do a bunch of investor calls, like 30 a week. When coordinating times with VCs there’s a kind of weird dynamic where you can't really send an investor that you don't know very well a link to find and schedule time on your calendar. It’s a power dynamic. It’s totally acceptable for them to send me a link to their calendar, but not the other way around. So, I had to tell investors over email a few individual time slots that I was available to meet with them.

As a result, I had to manually remember what times I offered to what people, and with 30 ongoing threads I would accidentally double book people or schedule calls in the middle of the night due to a timezone mixup. I made some pretty embarrassing scheduling errors while pitching investors when we really needed money. So that's when the seed of the idea started. 

Later in the year, when we needed to pivot our fitness startup we decided to focus on that calendar scheduling problem. At the time, there were a lot of cool email clients out there. Superhuman was pretty hot, but the calendar space was pretty much dead. We set out to build the next generation calendar for people who worked at a computer all day and needed to schedule calls.

After six months of building, we launched in January 2020. I hate to say this, but we got pretty lucky with the timing of the pandemic and the lockdown. When everyone had to work remotely, the calendar was now very important. Everyone started to look at scheduling apps and tools.

During the early days we manually onboarded every new customer through a 30 minute call. I did the first thousand calls and now our team has done probably over 10,000. There aren't many people who understand digital calendars and scheduling in a corporate environment better than my co-founder, our team, and me.

And that's what really excites us because we know thousands of our users from a 30 minute call like this, like we're having, and they really got to know the product intimately.

About a year ago, in October we launched on Product Hunt and opened up Vimcal to self service signups, so new customers weren’t required to do a 30 minute call with us. A few months ago, in November, we launched our iOS app, which is free.

Tell me more about your decision making behind doing a closed beta where you manually onboarded every new customer rather than the more traditional consumer playbook of self service signups. Did you have a specific time period, like six months, that you had planned to do the manual onboarding before opening it up? 

JL: I wish the answer was strategic, but because we had pivoted the initial product during YCombinator, we were only able to raise a small amount, about $200k in 2018. We were very frugal, barely paid ourselves, and that $200k lasted us from 2018 to 2020. But we were running out of money. We launched Vimcal with only a month and a half of runway. So it was a Hail Mary. 

We didn’t have time to build a proper onboarding flow. Also, normally you tweak an onboarding funnel over time as customers churn through it. We couldn’t afford to lose customers. Instead we thought it would be better and quicker if we have everyone who signed up a white glove service through a video call. Not only could we give them the best experience, but we could also learn what a self-serve onboarding flow would look like over time. 

So I started doing onboarding calls all day and my co-founder coded all day. Then on weekends and nights we’d code together. 

I literally had calls from 8 a.m. to 6 p.m. nonstop every day. My calendar was just blue and my lunch breaks and bathroom breaks would basically only happen when people rescheduled or canceled.

I think that these calls are one of the main reasons for the success of our public Product Hunt launch. I was just a fanatic about the product. But I also got to meet face to face with our customers. They got to know the person behind the product and that makes it a lot easier for them to support us.

Another thing about these calls, while it did limit our growth in that we could only onboard a limited number each week. People did convert at a much higher rate. For most of 2020 and 2021, 70% of the calls would convert into someone putting their credit card down at the end of the 30 minutes. 

Wow, having the onboarding calls all day every day must have been intense. Sounds like you learned a ton from customers on their workflows and problems. Since you were almost out of money and there was a lot of interest in Vimcal due to the pandemic and forced remote work, did you start fundraising again?

JL: So, we launched Vimcal in January 2020 and then I started fundraising in early March 2020. It was actually the day before the lockdown in California happened. But with the lockdown, all of the investors just got really panicky and all the funding dried up. So, I decided to just focus on the onboarding calls. Ironically, the onboarding calls were with a lot of founders, angel investors, and venture capitalists. At the end of some of the calls they would ask if we were taking checks because they loved the product so much! 

So the first check in our fundraising round was actually from someone who I did an onboarding call with and at the end they offered us a $5k investment. For us that was like two months of runway, it saved the company.

So of our fundraising round, a lot of it was from customers who loved the product so much and wanted to invest in us.  

That’s really cool. Perfect scenario that some of your ideal customers were also investors.

I heard from a founder who did a waitlist beta that they found that if someone was on the waitlist for to long, meaning the founder didn’t work through the waitlist fast enough, that the prospective customer would have lost a lot of interest. Did you notice anything like that if your waitlist backlog grew too long? 

JL: We qualified users when they signed up for the waitlist and we were pretty disciplined with ensuring only people that we thought should use the product were kept on the waitlist. It also helped us not only shape our product, but also get the word of mouth engine going. 

One more question about the onboarding calls. An important aspect of product management is staying focused and not getting distracted by too many miscellaneous customer requests. I imagine you’d encounter a lot of people saying: “if I only had X I would sign up.” Did that happen and if so how did you avoid adding every little feature that a prospective customer asked for?

JL: There are few ways to do this. One is when you talk to your users, I think a lot of people listen to the loudest voice rather than finding the commonalities across requests. Some customers are just very vocal or angry about certain things, but what you need to do is listen to the feedback you hear over and over again. You have to look at the common pieces of feedback you get from your target users rather than the sparse feedback or requests from a lot of different types of people.

For example, we wanted to cater to people that had a lot of external meetings. Some people have mostly internal recurring meetings and they have different needs and use cases. So if you are a founder or investor type, your feedback generally was more relevant to what we were building. 

Another way to filter the feedback you receive is that you, yourself, as the founder, need to have product intuition or taste. To achieve this you need to use he product a lot yourself. Luckily, calendars are very generic tools that everyone uses, so we understand calendars and we've used calendars a lot ourselves. That’s the one main difference between Vimcal and the other two companies we started. The other two companies were not built for our own use and that's why when things got tough, it was kind of a drag.

Let’s talk about the time since your public launch on Product Hunt in October 2021. How has your product evolved since then? You mentioned that you introduced self-service onboarding for that launch. How has your product strategy changed?

JL: When we launched, we only had a desktop app on Mac and PC. Our strategy is to be everywhere you manage your calendar. We've focused on adding an Outlook integration, we’ve released iPhone and iPad apps, and an Android app is on the roadmap. Some tools are good for certain devices, but for tools such as calendar and email, you have to be everywhere. 

In terms of user acquisition, we did introduce the self service onboarding, but we still try to nudge as many people as possible towards an intro call because nothing can replace a high touch 30 minute call. They still work really well for us. We’ve gotten to know our product so well and the common customer needs that we can do a great job demo’ing the benefits to prospective customers. 

You said that for calendars it’s important to be on every device, but you launched before an iOS or Android app. How did you decide that you were ready for the public launch?

JL: The main reason for the timing of the launch was the new learnings slowed down over time as we talked to thousands of users. We felt like we've iterated enough off feedback that it was time to launch to the public. The ROI was going down from talking to people one on one. Because of that, we decided it was time to open it up to more people.

In terms of devices, you can always have more things that delay your launch. Instead, we thought iOS could be another launch event and that’s what we did when we finished it in early 2022.

I see, yeah that makes sense. What's your customer acquisition? Do you have a referral program? Do you spend money on marketing?

JL: Because calendars and booking links are inherently viral, we get a lot of users through that. Referrals are a tactic too. A lot of people talk about us on Twitter, recommend us. Apart from that word of mouth we are experimenting with other types of growth, but still pretty early for that.

Something I’ve been thinking about the past couple of months is how to operate better. Have you implemented any systems or methods that have improved you or your team’s performance or improved your product development process?

JL: One thing that's helped us since we are a fully remote team is something we call 50, 75, 100. I'm borrowing this from my co-founder, Mike, who implemented this for how we check in on design and engineering work.

We check in with each other when it's 50% done, then 75% done, and finally at 100% done. We found that sometimes when you're fully remote, an engineer might start working on a ticket that has a good design spec, but when you get to the code review you realize that there was a mistake in the spec or maybe something was misinterpreted. This means the engineer might have spent like two days on something they didn’t even have to do.

We still want to have good specs, but the key is to have these checkpoints at the 50%, 75%, and 100% stages of the work. We’ve found this gives our engineers and our designer autonomy to work async. At the 50% done checkpoint we do a real quick check. It might not be a fully polished design or pixel perfect, but we can say, “Oh, let's focus on this and not that” and make adjustments to the spec for the future. That way no one goes down a path of perfecting something that they didn't have to do in the first place. We found that had been happening quite a bit.

Interesting. I really like that and I’m definitely going to start using that. Now, let’s go to the quick fire round. What are you most proud of from the past year since you publicly launched and opened up your waitlist?

JL: Our team. They have launched so much in the last three months. So apart from our Outlook integration, which required a complete rewrite of our code base because everything was kind of tailored towards the Google ecosystem, we also built our iOS app. We also launched a new product called Maestro, which is an even more powerful calendar designed for executive assistants, virtual assistants, people who schedule on behalf of an executive or a partner. We built this as a separate product because executive assistants’ use cases are pretty different. 

We launched all of those three things within a month of each other with just four engineers and one designer. So I'm really proud of our team for doing that. 

It’s always nice after you’ve been heads down for a while building to finally start shipping and getting your product into customer hands. 

What's been the most challenging part of the past year?

JL: The most challenging part, I would say, is shifting from a very strong product culture to one that focuses on growth. There's that saying that first time founders focus on product and that second time founders focus on distribution. For us, that's so true. For the first two and a half years, we were product, product, product. Always think about what to launch next. We honestly didn’t do anything for growth and we were lucky because we had a lot of word of mouth. Now it's more competitive and we want to scale to the next level and get the next order of magnitude of users. To do that we have to be more disciplined about growth. So I would say that mentality shift and the internal discussions we're having, just putting more meetings on people's calendars about growth instead of product, that's been probably the most challenging thing. But it’s also going to pay off.

I’d definitely hard to push yourself out of your comfort zone.

What book do you recommend to people and why?

JL: I'll give you one fiction and one nonfiction. First is Animal Farm by George Orwell. It's a very short read. It's basically about an animal farm that's run by pigs. It's a metaphor on how bureaucracy and stuff can crawl into an organization that was once grassroots, doing the right thing. I see it as a metaphor for startups becoming dinosaurs. I think it's just very interesting to see through the lens of a bunch of animals. 

A book more relevant to business and startups that I recommend is The One Thing by Gary Keller. It's about prioritization and understanding what's the highest leverage thing you can be working on at any given time. Basically the concept is to ask yourself, what is the one thing I could be working on right now that will make everything else unnecessary or easier? What’s the first domino, or what will start turning the flywheel?

For me, working as a founder of a startup. It's stressful having to do a million things at once, but shifting to always doing the most important thing first thing in the morning just de-stresses me so much. Once you get something big or nerve wracking done by 11 a.m. the rest of the day you feel so productive and stress free no matter what you do. 

What do you know now that you wish you'd known a year ago?

JL: I feel like I wish we had learned to be more disciplined with growth. One piece of advice we got from YC was track attribution and metrics as early as you can on your product, even when you think you are too early. They were saying this over and over. That’s one of the only pieces of advice we didn't really listen to. I think everything else we did by the book, but with tracking and attribution we were busy and just never got around to it.

Since we've begun to track attribution and analytics of our product we’ve discovered so much low hanging fruit to optimize. So I wish we had listened to YC and understood the importance of tracking your product analytics as early as possible. It doesn’t take long to implement.

My last question, what's your advice to founders who are considering starting a company in 2023?

JL: We've pivoted quite a few times, so I feel like I have quite a bit of experience choosing ideas and brainstorming under very high stress. The clock's ticking, we are running out of money and we need a new idea.

So, for a new founder that is thinking about startup ideas my advice is to really consider if the idea is a business on its own or just a feature of a larger product. Sometimes what seems like a good idea for a company is actually just a feature that will come later as part of another company. For example, a lot of people do travel planning apps, but those tend to fail as standalone companies. But if Airbnb did travel planning, it would make a lot of sense. So it’s important to think of the order and maybe focus on the bigger thing first. We made that mistake too and focused a year or two trying to push something that wasn’t going to work as a standalone product.

Another piece of advice I’d give is try to disprove your product as quickly as possible. For first time founders their first product is your identity and your darling, you're known as the person who does “this” type of company. After your first pivot, you’ll shift your focus on getting traction and building something people want, not just clinging on to making that one idea work.

That’s great advice. Thanks for taking the time to speak with me today, John!

JL: You’re welcome! It was great chatting. 

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I hope you enjoyed my interview with John and learned a few things. If you did, forward it to a friend. This helps more people discover my newsletter  😊   -Tyler