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Our co-founder and President Mena Trott has been sharing her stories on her personal blog Dollarshort since 2001.

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Barak at Six Apart

On April 20th of this year, The Mercury News ran an article about the how Jonathan Abrams (Friendster) and Sean Parker (Plaxo) were each handling changes of management and their departures as CEOs at their perspective companies. Apparently, they were handling it in different ways and Parker had seemingly been "dismissed, almost without a trace."

Ross Mayfield wrote a thoughtful post on this article and I considered writing my own post on how I, as a CEO, handle transitions in Six Apart and in our team.

I decided against it because I wasn't ready to create a stir of speculation. Tonight, on the eve of a change of position, I write about Barak Berkowitz who will be taking over my role of CEO.

It's a long post, but is incredibly thorough and frank and I hope visitors to this page will read through it in its entirety.

Pre-Funding

The first time we met Barak was at the first Supernova conference in Santa Clara. We had agreed to meet with Joi for lunch since he and his Neoteny team had been involved in the localization of Movable Type. We went to lunch with absolutely no intention to accept funding; we figured we'd have lunch, talk about Movable Type and TypePad and then part ways.

Barak was introduced to us and I sat through the lunch thinking his name was "Brock." Now, Barak is, physically, a big guy and can be quite intimidating -- I immediately said to Ben, "Who the F*#$ is this Brock guy? Joi's bodyguard or something?"

Apparently, Barak had worked with Joi at Infoseek Japan and was here sitting with us to see if Six Apart was a worthwhile investment (the presumption was that we wanted an investment). When we were asked what we wanted to do with Six Apart, we stated that we were working on a hosting service (TypePad) and that for it to be successful, we only need a couple hundred of subscribers. It'd be a niche service we figured, with prices starting in the $15-$20 range. Easy money, we figured.

As I said in my post about our acquisition of Ublog, I usually sit through meetings with a rather deadpan expression on my face. Most of the time people think I'm mad; the other time, they think I dislike them. Sometimes they're right. At this lunch, I had begun to already make up my mind about Barak.

When we had told Joi and Barak and Minami-San (a former Neoteny employee who joined us for lunch) about our plans, Joi still seemed genuinely excited to work with us and wanted to further discuss an investment. When Joi expressed this, Barak said something to the effect of "there really isn't an opportunity here. Have a good life."

So after this meeting, I revisited my original statement about Barak but added "what the hell was that a-hole's problem?" Apparently, Barak knew what buttons of ours to push -- Ben and I are extremely ambitious and to hear a lack of interest only spurs us on to fight. He was polite to us and told us about some cousin of his that runs a software company that supports his family and one or two other employees.

We didn't want just that -- we wanted to try to take on more.

So, a couple weeks after this lunch we made plans to go to Japan -- and Barak, since he lives in California -- was going to be our escort. Of course, before our flight I told Ben he'd have to sit next to Barak if it came down to it. Luckily, for us, Barak used his miles and upgraded while we sat in coach.

But surprisingly we quickly began to warm up to Barak and during the course of the trip we began to let our guard down. I can't remember if I started to make jokes at Barak's expense during this trip -- but now, I can't imagine a day when I didn't.

One of my favorite anecdotes about Barak has to do with the car he drives -- a BMW convertible. He's always on his cell phone and has a head-set in his car. Ben and I have the habit of mocking middle-aged men that drive expensive sports cars by saying things like "no matter how fast you drive, you're not going back in time and get those years back!" One day, we saw one of these sort of guys and Ben made that type of joke. That's when I got really serious and said "don't say that Ben -- that might be someone's Barak!"

(I write this all knowing that I'm going to have to see him at work tomorrow in our shared office and give him the sort of look that says "it wasn't that mean").

So we got back from Japan and began working on the term sheet. For almost four months we met once a week in a coffee shop in the Outer Richmond neighborhood of San Francisco (where we live). This was the sort of coffee shop that's perpetually empty but is filled with signs that say "you must order something to use electricity," "no more than 4 to a table" and "minimum $5 purchase." Of course, this explains while the damn place was always empty.

So Barak, Ben and I sat in this coffee shop and went over the terms of our funding in great detail. Additionally, Barak continued to amuse us with the sort of stories that we'd respond to with a "oh, we weren't born yet." These jokes never get old.

Post-Funding

When our series A funding closed, Barak joined Six Apart as Neoteny's representative board member. He helped us find an office, work out infrastructure details and would answer any questions we had. Oddly, as I write this I try to think about any milestones during the months of July to October and draw a blank. The time spent finishing up the first version of TypePad was a completely all-consuming event.

So Barak became more an more involved because we became more and more comfortable with his guidance and actually enjoyed having him around. The one piece of guidance that we were resistant about what the speed to which we needed to scale.

Now, you'll hear anti-venture funding people say that VCs work hard to make you burn through your cash. We were at the point when we were not burning through our cash but were completely burning out emotionally. Ben and I were doing almost all the development work on TypePad while trying to run the company, while trying to figure out what to do during the next six months. I had never felt so much stress in my life -- the stress was due to (1) the responsibilities (2) the workload (3) our resistance to think of ourselves as a company and the money in the bank as anything but our savings.

The one thing that Barak kept on telling us was that we needed to start hiring. In hindsight, that has been one of our biggest setbacks. Too many people at Six Apart juggle too many roles and although I'm happy that, financially, we're doing well, I'd be happier if we were burning more and all working less.

An example of wearing one too many hats and Barak's personality: At our office, we had phone cables running up and down walls and doorframes and across the floor. This mess was around for months until one day Barak came to work with a T-shirt, some tool-belt type thing and some device to do phone wiring. During the course of the afternoon, Barak installed our phone lines and cleaned up the office.

Incidentally, while he was doing this, Maile, our administrative assistant came in for her first interview with us and saw Barak. A week or two later when we called her in for a second interview I asked that she speak with Barak so that he could interview her as well. After we hired Maile and explained who Barak was she laughed and said "Oh, I thought he was the handyman and that this company really liked to get everyone involved!"

The fact that Barak will do this sort of grunt work is why he fits in at Six Apart.

The turning point to my story comes in Japan, after a particularly grueling 10-hour negotiation session with a licensee (in Japanese, no less). As I watched Barak handle our side, I was struck with the realization that I wanted Six Apart to succeed and for that to happen, we needed to bring more experience up front and center.

Today

I'm a proud person, but not a foolish person. I'd rather be a part of a successful company that I co-founded and ran as CEO for a year than hold on to a title because of ego.

Young CEOs exist, but I doubt they exist without help from experienced elders (I just had to use that word). Sure, I could be a miserable twenty-six year old CEO, but I'd rather be a content and productive twenty-seven year old president.

In my last post, I wrote about how proud I am about what we've accomplished to this point. I believe that I have done my best. I also know that tomorrow, as Barak officially becomes CEO, I will doing almost the same sort of work, attending the same sort of meetings and making the same sort of jokes I have been making for almost a year and a half.

The difference is that now I can begin spending more time on the sort of stuff that really makes me happy -- envisioning the next versions of our products, writing more publicly about the space and our experiences, speaking more at events and generally being more involved in the weblogging space as a whole.

The company is growing but Ben and I continue to be committed to bringing in people that mesh and that we like. We like Barak. Barak has seen me passed out in a Roppongi Karaoke bar as well as accompanied me on my first flight without Ben in nine years. We share an office and fight, but we also work well together. Part of the reason I feel incredibly lucky for the past year and half is because of all the sort of things Barak has taught us (both personally and professionally). I'm actually a physically better person because of this company.

I fear that my sentimental shift will cause too much pleasure in a certain co-worker who also shares my office (more about him below).

We've all learned a lot in the past year and a half.

In an early meeting in that coffee shop in January or February, when we were talking about names for the TypePad service, Barak was insistent that "Blog" had to be somewhere in the name. I said that over my dead body I'd have that word in our service. Although he was persistent, Ben and I didn't budge. After all, "blog" was not only too much of a buzzword at this point in time, but it would become incredibly dated as the medium evolved.

As we bickered over the usage of blog or not, Ben and I questioned whether an "outsider" such as Barak would understand weblogs and the culture. We figured that it was this un-chartered territory that few understood.

What we didn't realize is that his perspective would be invaluable. He has grown to understand the nuances of weblogging and still challenges what we have to say. Most of the time, however, we're on the same page. It's hard to imagine that we'd come so far in such a short time.

The main purpose of my post is to introduce Barak to our community and share with you why we have put him in this role. Barak not only brings with him an incredible background in the technology industry but also has the ability to adapt and listen to our users (sometimes better than us since he is able to remove some of the emotion that fogs up our own perspectives).

In re-reading this post, I'm almost embarrassed by my sincerity. I feel strongly about this company and feel that the addition of Loic and his team, Andrew and Barak will only make us stronger. Sure, we'll make mistakes from time to time. And, we're bound to do things that sometimes our users will question. However, with the team that is in place (and the people who will be joining), we are certain that we are distributing our strengths to make our product stronger and our customers more loyal.

So, for all you out there who've read up to this point, I hope that I have proven that it's possible for a CEO to stop being CEO but still be content in a company. Additionally, I hope that this weblog influences others in my position to share their experiences.

P.S. We also hired Andrew Anker.

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