Henn Ruukel spent a number of years working for messenger giant Skype. However, the irony was that he was frustrated with not being able to communicate on a group chat outside of Skype or his PC, other than via email. So he approached his colleague Asko Oja with the idea of starting their own messenger system that would allow people to communicate and share files over multiple devices and across organisations, and so Fleep was born. We spoke to him to get the full story.

What is Fleep?

Simply put, Fleep is a messenger for teams and projects.

And where are you based? 

Our team is primarily based in Estonia, with offices in Tallinn and Tartu.

How long have you been working on the Fleep concept and what stage has it reached to date?

We started building Fleep in December 2012. We’ve always had a very iterative approach to building the product, and we’ve always launched newer versions as early and often as possible and improved the product based on users’ feedback. I think Fleep has met its product market fit and we are currently in growth stage.

Tell us how the idea came about – was there something you experienced or encountered that made you determined to create this to solve a particular problem?

Yes, the idea to build a new messenger grew out of frustration. Whilst working at Skype we used Skype messenger for our work and it had several flaws – it didn’t work over multiple devices, didn’t work on mobile, was not able to share files, didn’t had search functionality – thus I went to my colleague Asko Oja (my Co-founder & CTO), and asked him, “Why not leave and build a better messenger for teams and projects?”


As we know that instant messaging is a very competitive market. Who do you see as your ideal target audience?

Fleep is best suited for people who work in multiple project teams across organisations or over organisations. For example, projects in marketing, IT, building & construction, and education. Although the messenger market is competitive it is still in the very early days and email dominates the business world. While the rest of the competition is optimising for team internal use, we have the advantage of being able to be used in multiple teams over organisational borders as well as internally.

And do you think Fleep is unique in its own way? If so, what do you think is the biggest ‘unique selling point’ comparing to other competitors in the marketplace?

Our biggest advantage is being open network. Open in the context of all Fleep users being able to message with each other (whilst competition allows messaging only within team) and in addition to Fleep-to-Fleep messaging we support adding email participants into conversation which brings the entry barrier to almost zero.

What do you think about the competition with Slack, which grew massively over the last 2 years?

Slack has done a great job in launching a new messenger onto existing market niche of team internal messaging, previously dominated by HipChat and Lync. This market niche is big enough specially if they grow (and I think they will) to enterprise.

Fleep is different from them in that it’s an open network like email – it works across teams and businesses. For example we are conducting this very interview over Fleep, while even if we were both on Slack we couldn’t use this for this interview but instead we would fall back to email.

As currently it’s free to use, how do you plan to monetise the product?

We will roll out paid subscription later this year and it will include administrative and control features giving businesses control over their user accounts, messages and files. Many businesses have asked for the ability to own user accounts and they are willing to pay for it. The free version will continue to include all the current features.


The Fleep team

How about funding the project? Did you get to raise investment from Angels and/or VCs?

We have been very lucky with funding. Since the beginning we have had strong support from Skype founder Jaan Tallinn and other angel investors who are still with us, helping us not only with financial support but with advice and networking. We have not raised any VC money yet.

Is this your first start-up venture or did you start other businesses before this?

Fleep is my first venture. I have never built a company before, but I’m loving it, and I hope I can continue building it for times to come!

Let’s chat about yourself a bit more. Tell us about your family and academic background. Any entrepreneurial family member or partners who inspired you?

I’m not sure how my family has inspired me – probably through support and creating self-confidence. I think a bigger role to play leading into the Fleep story was being part of Skype in the early days of growth and success – I think mostly this gave me the courage to start building Fleep.

I have a BA in IT management. Prior to Fleep I worked for 7 years at Skype where I built and lead the Skype Site Operations team. I joined at the time when Skype was acquired by Ebay (in 2005) and I left in 2012 after the Microsoft acquisition.

When I joined we were less than 100 people but by the time I left there were over 1000 people! So I had the unique opportunity to see the growth of a successful startup to corporate. Before Skype I worked in Estonian local Telecom where I led network operations teams.

Do you have any hobbies that you are passionate about that add balance to your work life?

Outdoor sports are my passion – in summertime it’s orienteering and mountain biking and in winter cross-country skiing and snowboarding.

Do you have a role model who inspired you to take on this journey?

It’s a cliché – but Steve Jobs – I love his definition of a “product person”. I didn’t know him personally, but based on what I’ve read, while I cannot accept his approach to people and team around him, I do like his passion for building awesome end user products.

Do you have a business partner? Any interesting stories here?

I have a strong partnership with Asko, as we worked together at Skype. As soon he was willing to join me to build Fleep I knew that I didn’t need to worry about the technology side of things. Asko is very passionate about what he does.

Henn and co-founder/CTO, Asko

Henn and co-founder/CTO, Asko

What about a life partner? What role does he or she play?

My partner is very supportive of me and Fleep – she has seen start-up life herself and I think this helps her to better understand the challenges we have.

Have you been through any tough moments since starting the project? If so, how did you get through this?

Fundraising has been tough – we have had few rounds where it has felt that we are unable to close and as these periods of high uncertainty usually last for several weeks they are very challenging, but you have to keep going and keep the team moving forward as well. At times of high uncertainty it helps to simplify the situation to the actionable tasks and keep working on them and then you see gradually things turning towards certainty and eventually things get solved.

Have you made any memorable “bad” decision or mistakes along the way?

Sure and probably even more than I’m aware of! 

One mistake for us was focusing too little on growth and traction and too much on building the product. But all that matters is how much I’m able to change this going forward.

I think building a start-up is a venture where we do something ambitious and for the first time, thus making mistakes is a natural part of the process.  We shouldn’t try avoiding them but should rather learn from them and move forward.

What is your ambition with Fleep? What are your future goals?

Our long term vision has always been to build a messenger that potentially could become a ‘verb’, and offer people alternative to email communication. In the next 3 years our single goal is to prove ourselves in the market and get out of the survival mode!

Finally, what would be the one bit of advice that you would offer to a fellow start-up?

My advice is easy to say and hard to follow. It would be:

  • Start, continue and don’t give up. It will be hard – there are no easy answers or solutions.
  • Be honest. To yourself, to your team, to your partners and to your investors. Truth is often hard, but it gives you good sleep and the world is small. Lies only grow and eventually catch you.
  • It’s not a sprint, it’s a marathon – choose a tempo that you can sustain for many years.


photos credit: Andres Haabu