August 1st marked the end of my 8+ year journey with Skype, after returning from an academic break at Stanford. As expected, the top incoming question following my departure tweet has been “what’s next” – so let me share a bit more.
First, a quick glance back
It is just unbelievable to think how far Skype has come from when I first walked into the scrappy offices in the back wing of a soviet-era research institute building in the suburbs of Tallinn, Estonia. The little piece of free software released to the world felt like a rocket ship already. It already had its first millions of users, but was still a long way from the casual household name it is today.
War stories of this European internet juggernaut will one day be sufficient for both business history and fiction books. As a founding engineer at Skype, Toivo Annus used to say, “our modus operandi is change.” Yet I don’t think even he could have predicted the amount of change that was ahead. The role I started in oversaw the growth of our original R&D site in Estonia from Series A startup stage through eBay buying us and then selling again, the Silverlake-led private equity era, the IPO filings and then eventual acquisition by Microsoft. During the most turbulent times I reported to three different CEOs in the span of a mere four months.
Yet, we managed to nurture and evolve one of the most passionate company cultures the tech industry has seen and attract the cream of the crop in talent to join the mission. To tiny Estonia, Skype has been a source of national pride and the #1 desired place to work for technologists in the region.
Such crazy growth of a product and company also gives ample opportunity for personal and professional growth. Getting stuff done across 10 offices and 16 timezones we had spread our employees around before we even grew our headcount to a few hundred. Finding novel ways to glue teams together when no two colleagues share the same passport or work in the same office with you. Bridging cultural gaps across geographies, business and engineering, and oldtimers and newcomers.
Of the quite few global teams I had the privilege to lead, I’ll most fondly look back at two product groups: the sometimes insane experiments to invent non-telecom revenue streams for Skype (remember SkypePrime, SkypeFind, Skypecasts, anyone?) and the highly controversial design revamp of our flagship Windows and Mac clients in 2008. The latter created borderline civil unrest among loyal users, yet took the measurable user engagement metrics and share of video calling minutes through the roof. Disruption — of even itself — has been at Skype’s core since it was born.
I’ll leave it to others to judge if and what I personally contributed to the Skype story. What I know for sure is that Skype and the people behind it gave me more than a fair share back. I am thankful to all of them, especially Taavet, Toivo and Niklas for inviting me along in the first place. I wish all the best to colleagues still working on Skype.
And now, forward
Simply put, my plan is to find the next big problem software can help humans solve. This is why I am joining one of the most admired firms in modern venture capital world, Andreessen Horowitz (aka a16z) as an Entrepreneur In Residence.
While at Skype, I had the luck to work with our then board member Ben Horowitz to hire some key positions in Silicon Valley. Through him, I got a glimpse into how a16z thinks and works with their portfolio companies to lend a supporting hand in the harsh struggle for creating something great from nothing. We’ve since kept in touch and I have been a fan of the crisp and down to earth leadership writings on Ben’s blog. When he extended the EIR invitation, I didn’t have to think long.
If you’ve read the “foundational script” of a16z, Why Software is Eating the World by Marc Andreessen, you see how much my approach to business aligns with this firm. Curiously, I founded my first startup in 1996 on the wave of the commercial internet, which was kicked off by the first graphical web browsers, Mosaic (co-authored by Marc) and Netscape (by Marc, Ben and others now at a16z). I’m just honoured to get to work so closely with them and everyone else at a16z this time around.
While I do intend to keep growing and supporting the fantastic startups in my angel portfolio, I’ve decided not to become a full time investor (yet?). Instead, I have my sights set on another operational role, either by starting a new venture or joining an inspiring early stage team to help them scale their business and products.
While I remain irrationally patriotic for Estonia and Europe in general, for now we have decided with my family to extend our stay in Palo Alto.
Life is an upward spiral.