The satellite town of Bucha, on the outskirts Kyiv, has become infamous during Russia's two-month-long full-scale invasion of Ukraine for all the wrong reasons. But for Sass, who met his wife, Vitaliia, in the commuter several years ago, and whose mother-in-law lived there until late last year, the city also holds special memories.

So does the rest of Ukraine. The entrepreneur opened the second branch of startup accelerator Lift99 in the capital in 2017 and has invested in startups across the country, in other cities which have unfortunately fallen from the lips of the world's TV anchors in recent weeks: Lviv, Kharkiv, Dnipro and Odesa.

"I have never in my life seen something which is so cruel and so black and white," he told ERR News earlier this month, speaking about the war which Russia started on February 24. "There is no way I could see or feel this any differently."

Asked how he and his wife are coping with the news from Bucha, he says: "We have trained ourselves [not to look]... You can go crazy if you look. It is very, very difficult for every Ukrainian but half of the country is still working."

On February 25, Sass sent €20,000 to the Ukrainian Army but quickly realized he wanted to do more. As with many Estonians, Russia's actions have yanked stories from the past back to the present.

"I remember stories from my granny when I was a small child, but I never focused on them and now I am like... this was all true... Russian soldiers have not changed in 81 years. And this is horrible. When the war started, I was in shock," he says.

By the time he speaks to ERR News on April 19, the founder of Pipedrive has sent four convoys of vehicles, approximately 50, stuffed with humanitarian aid to Ukraine and a fifth one is being prepared as we speak. His vehicles have helped 28 army units so far across Ukraine.

Sass' interest in humanitarian aid was sparked in 2008 when he participated in an aid mission to Georgia following Russia's invasion so he knew it was possible to help now.

Colleagues on the ground in Ukraine said that while humanitarian aid is important, the military needs vehicles to operate.  

"We started to look into it more deeply and realized these are extremely motivated people but they are lacking almost everything. This is how we started the first [convoy] and this week convoy number four leaves [for Ukraine]," he says. 

While some cars are donated, most are purchased. They are given a checkup first, then fixed or repainted and filled with aid such as medicine, warm clothes, food, even gasoline has been sent in the past, and drones that are "super needed." When aid is delivered photos are sent back to the organizers in Estonia to prove the help reached those in need.

Inspired by the news of convoys of vehicles being driven to Ukraine from Lithuania, each of the vehicles in the first convoy were driven to the Polish border but now, as things have progressed, cars are put on a vehicle carrier.

"It was pretty crazy," he said, recalling the first trip. "[I drank] Fourteen Red Bulls in 19 hours."

Speaking about the future and how Sass and the Estonian startup community will continue to help, he says this is up in the air at the moment.

"No one knows how long the war will last," he says, adding a fifth convoy will certainly be sent soon. "But we are talking already about how we can build the country up again /.../ In the future, we can discuss if cars are the most crucial thing or if there is something else we can do."

The small and close-knit startup community has already been asking itself how it can help and is trying to hire Ukrainians when possible, but it discovered early on that most people had no intention of leaving the country.

Sass isn't pulling his investments out either. He firmly believes the trends which were seen in Kyiv before the war will return. Lift99 has temporarily relocated to Lviv in western Ukraine, it is twice the size of Tallinn's office and was full before the war. "We saw that so many people wanted to visit Ukraine, to invest in Ukraine," he says.

He also speaks proudly about his own investments, including a company that teaches people to code in six months which is "life-changing." But in the future help may spread out in different sectors.

"That our aim should be to help even beyond startups now, just any company that wants to export beyond Ukraine and sell their products globally. This is something which we have discussed," he says.

He says Estonia and Ukraine have a lot of ground in common, including history, which makes working together easy: "We believe that our experience in Estonia is relative for them /.../ But at the same time we have so many more unicorns [a startup valued at over US$1 billion] — so something is off."

Estonia has been advising Ukraine on its e-governance for years and looking at the way the country has taken the lead in some areas, Sass believes the pupil can now show the teacher the way forward.

He mentions Ukraine leapfrogging Estonia by developing government services on mobile phones and legalizing cryptocurrencies:

"We are not there!" he says exasperatedly, "So Ukraine can lead us."

Brave decisions are needed, the e-tiger is older now

Moving away from the war in Ukraine, back to Estonia, ERR News asks what else can be done to attract talent to the country and whether the previous government's anti-immigration rhetoric had a long-term effect?

Sass believes it didn't and that people have become used to politics going "up and down." As for attracting newcomers, he said there is no "one thing, no silver bullet" which will make everything better.

"There are many things we can do better, like if someone relocates here how easy is it for their family to move here, to put kids in schools, how is the medical system," he says.

Another issue is making sure Estonia stays ahead of the pack which, Sass says, is one of the "biggest challenges."

"Braver choices and speed would be helpful because our tiger is a little bit older now, and so many countries are trying to copy what we have done," he adds.

"We have to push harder or the world will be talking about another country soon," he adds.

One area where Sass sees room for growth is in Web-3.0, the World Wide Web based on blockchain technology, but more understanding from the Estonian legal side is needed, he says.

Sass is a serial investor, having made investments in approximately 50 companies throughout his career but says his attitude has started to change in recent years.

"My first question, more and more, is how does it help to make the planet better? If it doesn't, why should I spend time on this? My sense about this has been growing stronger and stronger", he says.

"Now I'm investing for impact, for my values," he tells ERR News. "I am [becoming] more and more picky."

The result of this has been a turn towards investing in "cleantech" companies, such as Estonian company Single Earth.

He also wants to invest more in markets that traditionally see less interest, saying he stays away from the U.S., UK and Germany as they already have "great people" there.

This is partly to do with Estonia's own history and how difficult it was to attract investment 30 years ago but it's also about impact and being able to share relevant experience, Sass says. This is why Ukraine has been a particularly important country for him.

Some of these markets seeding fewer investments include Venezuela, Mexico and Georgia but he adds: "I would love to look beyond Ukraine, to Uzbekistan, Latin America..."

But could cleantech, which aims to reduce negative environmental impacts, and startups also help closer to home?

ERR News asks if these developments can help with transforming Estonia's most heavily industrialized area Ida-Viru County, which is a center for shale oil mining and must undergo a "green transition" in the coming years.

Sass, who knows the region well, believes it could. He points to Jõhvi Coding School which opened last year and aims to upskill the region's population and bring more investment. The initiative, backed by the government and IT sector, also aims to reduce the country's skills shortage and has attracted pupils from around the world. He believes similar initiatives should open across Estonia.

"But it's about doing ten different things, not just one," he says.  

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