⚡️ Founder Diaries Vol 1 Ch 1: John Li, Founder of Vimcal - Raising $3.5M After Pivoting 180°…Twice

We celebrate the unfiltered BTS stories of today’s founders - from their highest highs to the lowest lows and how they powered through it all… or didn’t.

😊 Welcome to Volume 1 Chapter 1 of Founder Diaries. Now, Why Founder Diaries?

In an era where founders’ lives are glamorized and their stories are romanticized narratives of seemingly endless success, the behind-the-scenes reality of the highs and lows of being a founder often don’t come to light.

Alongside the startup with a high valuation is the string of risky decisions, maxed-out credit cards, and grueling late-night chats.

Alongside each polished story, there are real challenges, unsung heroes, and unique highs & lows that make every second of the founder's journey worth it. Or maybe not? We will let you decide.

These are the true, unfiltered short stories behind the founders of today. Enjoy :)

👋 Introducing John Li, Founder of Vimcal: Raising $3.5M After Pivoting 180°…Twice

Vimcal is the world’s fastest calendar, beautifully designed for people who work remotely and live in their calendars. It comes fully featured with timezone conversion, booking links, keyboard shortcuts, and everything else a modern calendar app should have.

After stints at different startups, my co-founder Mike and I both landed cushy big tech jobs at Microsoft and Twitter. Though it was still challenging, the change of pace led us to want to build new skills outside of work.

We started hacking on VR projects on weekends for fun. What started as a weekend fun project, changed the minute ARKit launched.

We were hooked - we pivoted our VR weekends to AR and built an AR developer platform idea.

We applied to YC and got rejected the first time. On the second try, we got an interview, but it felt like it went terribly. They found the weak point in our pitch and just drilled down on it for what seemed like an eternity. We went home defeated.

A few days later, we got a call from Adora, our YC partner, telling us "Congratulations!" My voice was shaking, and we immediately started celebrating - hugging, dancing around, yelling with excitement.

Getting into YC was one of the highest highs early on.

But on day one of YC, Adora pulled us aside and said, "We like you guys, but we don't think your idea will work. You should pivot."

We were crushed. How could this be happening at the peak of our celebration? But we were stubborn and we stuck with our AR idea until we ultimately got to a point when we had to face reality. 6 weeks away from Demo Day, we were finally like, “Okay, this is going nowhere. And no one's using AR as much as we like our idea.”

So we did 2 really painful weeks of pivoting, asking everyone, “What's a pain point in your life, what problem can I solve?” and eventually we ended up on a fitness idea, a platform to show live-streamed fitness classes. We gained a reputation for shipping fast - in just 4 weeks we pulled together a slick fitness demo out of thin air but no real product, no traction, and we were barely able to raise during demo day off that.

For the next year after YC, we grinded away on this fitness app idea but barely gained any traction.

Our initial $200k in funding dwindled fast. That was the lowest of the low.

I remember feeling terrified during an office hours session with our YC partners. They told us, “Hey, you know, you got one chance to do the startup thing. Most people think they have more than one chance, but you only have one chance usually from what we’ve seen and then they go back to a normal life.” So we decided alright, we’re just going to fight until the end.

We had 7 months of runway left and it was our second time pivoting. This time we were very surgical about it.

We decided to create an improved version of the calendar specifically for founders fundraising.

We thought we were going to launch it in a month but it ended up being 6 months so we had a month and a half of runway left when we did launch it.

It was a Hail Mary.

After the Vimcal launch, I personally onboarded the first thousand users. One user offered to invest instead of paying our $15 monthly fee. That was one of the highest highs for us. He didn’t know it at the time but that small $5k check doubled our runway from 2 months to 4 months. A few months later, we got a $150k check, and then it just kept coming.

People started loving the product and people shared it on Twitter. That one $5k check was the difference between us going back to searching for jobs and where we are today. At the time we were already emailing our lawyers asking how much it would cost to shut down the company. So we were mentally prepared.

The highest financial high for us was recently a couple of months ago.

We closed our seed round and I remember looking down at the notification for the $3.5 million wire that hit my Apple Watch and I couldn’t believe it was real.

I had immigrant parents so money wasn’t exactly free flowing. After 11 grueling months of fundraising, the lifeline had come. We could finally stop worrying about survival and focus on the product.

This extreme journey of highs and lows has taught me that you can go fast without feeling rushed all the time. As founders, we often scramble to try new things instead of focusing on what already works. When we finally found something successful like our Vimcal Slots feature, we should have tripled down instead of moving on to build other features. I know now that when you find something that clicks with users, milk that channel relentlessly before looking for the next breakthrough.

There were so many terrifying low points where I thought we were doomed. But I've kept the perspective that even in failure, I will have tried my hardest at something impactful. I feel honored and privileged to be able to take this startup journey.

Now with a newly raised round, we are heads down building Vimcal into a company that lasts.

-John Li

Learn more about John Li and Vimcal below:

John Li: LinkedIn | X

Vimcal: Website | LinkedIn | X

If you know someone with a unique founder story who would like to share their BTS journey of founder life - the highest highs and the lowest lows - please feel free to refer them at diariesfounder@gmail.com.

— Michelle Kwok & Christine Lu Hong (The Founder Diaries Team)