One of the most striking shifts in entrepreneurship when I started Automattic seven years ago was the rise of the Founder Friendly VCs. The standard operating procedure at the time for VC-backed companies consisted of bringing in “adult supervision,” founders often taking largely-ceremonial roles like “chief architect” after the business had scaled to a certain point, aggressive financial terms around liquidation preferences, and a control structure that more often than not left founders with a minority say in the future of the company, especially if it went through rough patches. Folks like True Ventures (who Automattic has always been intertwined with) appeared as iconoclasts because they came out saying that founders were the best ones to grow a company long-term and structuring their entire practice and way of investing around that idea. It seems non-controversial now, but it was like Dylan going electric. Still in spite of their philosophical innovations, many of these funds were structured in similar ways to the ones of old, with 7-10 year fund lifetimes, for example.

Fast-forward to 2013 and there’s an even more founder-friendly class of investors rising, at least for companies that have made it past a certain exit velocity of growth and revenue. Most visibly pioneered by Yuri Milner and Facebook in 2009 there’s a breed of later-stage investors from largely financial backgrounds that come in with the ability to write checks larger than the entire size of most VC funds and a desire to align with founders so strong that they embrace things that even VCs from the founder-friendly cohort would balk at: forgoing board seats, assigning voting proxies to founders, taking very long term approaches to growth, and investing in (and seeking out!) companies outside of the California/New York bubble, from South Africa to Russia to Brazil. The most interesting thing to me about this new generation is how behind the scenes they are: forget about a blog or Twitter, most of these guys don’t even have websites for their firms. These are some of the smartest and most successful people you’ll ever meet and you’ll never hear about them… they like it that way. Asymmetric information is their core competitive advantage.

Anyway, wanted to get in front of the news that will inevitably come out in the next week or two: there has been a large secondary transaction in Automattic stock, about $50M worth. “Secondary” means that it’s existing stockholders, like the earliest investors or employees, selling stock to another investor versus money going into the company (“primary”). It was led by Lee Fixel at Tiger Global, one of the behind-the-scenes quiet geniuses that has previously invested in SurveyMonkey, Facebook, LinkedIn, Palantir, Square, Warby Parker… Automattic is healthy, generating cash, and already growing as fast as it can so there’s no need for the company to raise money directly — we’re not capital constrained. The minority of stockholders that elected to participate are holding on to the vast majority of their shares. We’re building an independent company that’s going to be a growing part of the fabric of the web for many years to come, so allowing early investors to lock in some returns releases any short-term pressure there might be on the company for a liquidity event and allows us to focus fully on the long road ahead.

As sometimes happens in with regulated financial things, I can’t answer every question about this, but will leave comments open. I hope to see some of you on Monday the 27th when I’ll be celebrating the 10th anniversary of WordPress alongside community members in over 500 cities. Also check out Toni’s post about all of the above. If you’re interested in living anywhere and working hard alongside people passionate about the same, Automattic is always hiring.