After a recent $30M in Series A funding on top of angel investor support, Whimsical has solidified its place as an exceptionally successful and rapidly growing startup. While Whimsical was initially founded in the US, its co-founder and CEO Kaspars Dancis has recently returned to Latvia — where he has already made waves by supporting the local innovation ecosystem. Let’s explore the decade long journey that led Kaspars and Whimsical to where they are now!

First startup steps

The story of Whimsical starts long before its inception — when Kaspars founded Cobook. He already had some startup scene experience, mostly on the technical side of software development, but Cobook was his first independent project — an address book app for Apple products.

“I did not have a specific reason to start a new company, but I wanted to try — to see what it would be like to run my own business. I like trying new things in life and to figure out solutions to problems on my own,” says Kaspars.

He emphasizes that when you work for someone else, you always need to give in to some extent. But when you start your own business — you can define your own rules and follow your own vision.
After about 3 years, Cobook was acquired by FullContact — a US-based tech company. Despite it being celebrated locally as a successful Latvian startup exit, Kaspars considers Cobook a failure: “We managed to sell the company as a soft-landing, but we were forced to do it. It was not something we consciously planned and decided to do.”

Lessons learned

Either way, Cobook was a valuable learning experience for Kaspars — which contributed significantly to how he approached starting Whimsical. The main takeaway was to figure out an idea he could be passionate about up-front. Something that would be compelling to work on no matter how much money it was bringing in or how easy or hard it was going: “I wanted to make sure I have this intrinsic motivation that would not change no matter how much time passed.”
The experience Kaspars gained also helped him become more confident about making decisions and trusting his own judgement. Before Cobook, Kaspars was a skilled software developer but had very little experience with the management side of business. He made the mistake of compensating for that by blindly following advice from people with more experience.
That lead to a number of failures, including what Kaspars calls the biggest reason Cobook failed — the fact that it did not have a solid business model. It was a product that people liked with good traction in the industry, but the team only started considering the business model when it was too late. The advice they had gotten at the time — to just focus on growth and get as many users as possible. Even if, in retrospect, Kaspars remembers it feeling wrong, at the time following advice seemed like the sensible thing to do. Having learned from that experience, Kaspars tried to think about the business model as one of the first principles when building Whimsical.

“There are a lot of smart people with plenty of experience and strong opinions about startups, but none if it is universal truth and there is always important context,” Kaspars emphasizes. “Every company, every business, every market is different in nuanced ways. Sometimes you have to do things the hard way and try to distil the problems to their smallest parts — and use your own reasoning to make a decision.”

Inception of Whimsical

After Cobook was acquired by FullContact, Kaspars continued to work there in different roles for more than 3 years. Towards the end, he was managing an engineering team of about 40 people, who were distributed all around the world. A big part of his was about figuring out how to make this team work together more effectively. Different physical locations and time zones created many obstacles and called for different types of software tools.
Kaspars did not feel that the tools were well optimized for the needs of the modern knowledge worker. Many of them were created in the era of software where everything was still very tied to the physical world. Once you had created something, you printed it out. As these tools moved to the web, collaboration functionality was simply added on top, the tools themselves did not fundamentally change. As a result — there is a lot of baggage that only gets in the way when working solely in the digital space.
Creating beautiful documents is irrelevant when all you need is to write some text and draw a simple diagram to share with someone on the other side of the world. You don’t need fancy customization that might be useful when showing the result externally, but frivolous when trying to clearly convey information to your team.

“These kinds of factors were the catalysts behind Whimsical — a goal to build a new generation collaboration platform that is optimized for purely digital and internal team use,” says Kaspars.

Co-founding and launch

Kaspars worked on Whimsical alone for about 6 months, but throughout this period he kept in touch with Steve Schoeffel, a previous co-worker at FullContact. They had developed a good rapport, and saw a lot of things in a similar way — often bouncing ideas off each other. Steve eventually decided to commit to Whimsical fully and joined the startup as a co-founder. For another 6 months they worked as a duo — with Kaspars focusing more on the technical side and Steve being the designer. And of course, as with any early-stage startup — they both had to split wearing all the other hats that are necessary for success, from management to marketing.

“We were focusing on what we want Whimsical to look like, based on our previous experiences in tech startups. Build something of value that is optimized for the kind of job we were used to,” says Kaspars.

Together, they kept iterating quickly until they had a product they were not embarrassed to release — validating it only against their own needs and by showing the prototype to a couple of friends. And after adding a business model, Whimsical was properly launched. It quickly resonated with some initial clients and started organically growing from there on. A big benefit of a product meant for collaboration is that it is intrinsically spread by the users.

“Steve and I have different personalities,” Kaspars adds. “I think it played an important role for us. I can be impulsive, while Steve is more level-headed. When I have rapid ideas that change every day, he can be there to push back when spontaneity goes out of control.”

Purely remote

Whimsical team is part of the new generation of startups that do not identify with any single location. Technically they were founded in the US — Kaspars was living there at the time and Steve is a US citizen. But it was clear to them from day-one that Whimsical is going to be a location-agnostic company. Fully remote, fully distributed. Hiring people from anywhere in the world, based purely on their capabilities and skills.
That said, early on in the life of a startup, the easiest and safest way to hire people is through your connections. Because of that, most of the veteran employees of Whimsical are from the US and Latvia. But by now, around a third of Whimsical team is from other countries.

“All of our work is remote. It’s more than just the way we work, it’s one of the things I believed even before starting Whimsical — it’s inevitable that most knowledge workers in the future will be working remotely,” Kaspars says confidently. “It’s also part of the reason why Whimsical has so much focus on remote collaboration.”

Kaspars believes that as much remote work as possible is a good goal for society. If certain jobs can be done from anywhere in the world and companies are open to that, then it will level up the standards of living for people everywhere and contribute toward levelling out the global economy. Otherwise, if rich countries are only hiring locally, it’s difficult for poorer countries to catch up.
At the same time, remote work is not a panacea without any problems. It’s harder to have productive relationships when you can’t meet in person. Kaspars mentions that losing the social aspect is a challenge and workers can start to feel more alone. It’s important to figure out ways to compensate for that. Whimsical team tries to meet face to face a couple of times per year — which has been very difficult since the start of the pandemic. Another option is to do random video chats about non-work-related topics.
Kaspars emphasizes that it is crucial to properly switch to remote work. You can’t simply copy the same work patterns you are used to from time spent in office culture — that way you will get the worst of both worlds. You need to rethink how work will get done — more asynchronous, more trust that each team member will do their job. The latter is one of the hardest things for many people — overcoming the discomfort of having to believe that everything will work out.

Future of Whimsical

The team at Whimsical is currently working on new features that will bring the software to the next level. Not only that, but they have expanded the management and sales teams — that were somewhat lacking during a period where the focus was much more on building the core product.
The overall vision for Whimsical is fairly broad — Kaspars hopes to build a complete end-to-end collaboration platform for modern knowledge work. There is still a lot that needs to be done, but he is confident that every step will provide even more value to the customers, making them more effective and happier at work.

“We get closer to that vision every day. But I find it much more helpful to think about the journey, not the destination. If you truly appreciate what you are doing now, you can be happy today rather than work toward happiness in the future,” Kaspars says. “People you spend time with at work, helping your customers — these things matter much more than financial outcome or status. There are now more than 20 people who have believed in Whimsical and joined our team. Almost every day I can’t believe how lucky I am to work with and learn from this amazing group.”

Back in Latvia

Having returned to Latvia, Kaspars and Whimsical have jumped into supporting the local innovation ecosystem, including Startin.lv. When asked about what stands out about innovation and startups in Latvia, Kaspars explains an interesting observation about different cultures.
Not just Latvia, but in most Eastern European countries, the millennial generation is almost universally better off than their parents. Kaspars emphasizes that we don’t realize and appreciate how important that is and how that gives us the ability to be more optimistic. After living in the US for almost 7 years, he has observed almost the opposite situation — most people feel a decline and that their generation is worse off, with no fault of their own. As a result — a lot of the tech scene where the US is so dominant is actually represented by immigrants, not people who have grown up locally.
If you tend to be more negative, you can become too focused on why something wouldn’t work, rather than figuring out how it could work. It’s easier to do something tough when you have a positive outlook and motivation.

“Ultimately, starting your own business and building it up is very difficult and I am impressed by anyone who is doing it. It can feel lonely, but know that you are not alone,” Kaspars inspires other entrepreneurs.

Originally published at https://medium.com/@startinLV