A few months ago I was chatting with John Borthwick, who had just returned from a trip to San Francisco. I asked him how the city was doing as if he were a traveler who had visited someplace exotic — “How is it over there?” (As an investor he probably sees the crazier side of the city, since part of his job is looking at hundreds of companies, the vast majority of which will fail, and trying to pick a few winners.)

Despite getting near-daily meeting requests, I don’t currently have any plans to visit San Francisco. I was there in June for a few days for Foo Camp and for drinks with the artist Tom Marioni. I returned for WordCamp San Francisco in October, and again a few weeks ago for Scoble’s 50th birthday party and a board meeting. But the couple-times-a-year rhythm seems to be enough for me. I’m enjoying the distance a bit, in fact.

There has been plenty written about the bubble culture in SF right now, including on the antitech movement that never really took off. It’s a topic I already blogged about in 2013. But I was curious to unpack my own thoughts about being away from it all.

What I don’t miss:

• Too many meetings — every possible company is there, and everyone wants to meet.
• High prices for everything, from groceries to cocktails. Not even going to talk about the real estate market and rentals.
• It takes forever to get across the city, even though it’s only 7 miles.
• The public transit, while workable, pales in comparison to other places like NYC.
• The weather isn’t bad, until you drive to Palo Alto or Marin and notice how much nicer it is there. (Or take a one-hour flight to Los Angeles or San Diego.)
• This is anecdotal, but I feel like cell phone service is terrible, especially for making calls. Calls are unintelligible and drop frequently. I think this is why everyone texts.

I don’t have any problem with the social scene; SF might be tech-heavy, but it’s fairly easy to get out of the tech bubble. Many forget that San Francisco is home to a ton of people working for non-profits, in fashion, finance, bio-tech, art, and music.

What I miss, deeply: the people. Some of my favorite people, professionally and personally, are in the Bay Area, and that’s the thing that will draw me back someday. I’m lucky that I can catch up with folks when they travel, like Jane or Tony in New York or Om in Italy. Of course the Automattic headquarters is there, along with some great colleagues, but I can also catch up with them at meetups.

I miss how much technology permeates the culture there, from billboards to services like Uber or Postmates (or Munchery or Spoonrocket) that today seem like conveniences, but will be the basis of something very meaningful down the line. You can feel like you’re living in the future there. Internet speeds seem to be getting better, too —  local ISPs like Webpass and Monkeybrains are leading the way, but even my Comcast account there delivers 120mbps.

I miss being able to run along the water, and the close proximity to lots of beautiful nature areas (granted I didn’t take much advantage of those when I was still around). The quality of light is really nice — when you can see it. Restaurants, though tending toward pricey, offer great ingredients and quality.

Finally, you can’t deny it’s a city of hustlers. This tweet has since been deleted, but you get the idea:

https://twitter.com/closetclicks/status/500345852352008193

One of the toughest things in business is when you get well-meaning advice from advisors, investors, or friends of the company who are valuable but might hold some ideas or ways of approaching problems that just aren’t applicable to your particular company or situation. They might be right most of the time, and it might have worked for them in the past to build a huge success, but it doesn’t mean it’s right for you, right now.

This is especially a struggle for Automattic because so much of what we do is deliberately different from companies that have come before us. The below is a sensitive-info-scrubbed version of a comment I made on an internal P2 in response to someone who had met with a close friend of the company who had said we should “hire more business people, and more people like so-and-so, who have a background in and passion for data analysis and structure. He also shared his ideas about what the additional business hires could be responsible for, such as P&L responsibilities for specific products.” The person he had talked to was asking why we weren’t following that advice.

The first part was easy, because so-and-so was actually leading hiring for a position around data and the early results were going well. The rest I ended up writing more about, which follows. It was only meant for internal consumption, so read it as such, but I got enough requests to share the comment publicly that I wanted to clean it up and release it for y’all.

On the “more biz people + P&L” side, it’s an area we disagree.

We’ve had more “business people” in the past, and found it just didn’t move the needle in the same way that investing on the support, engineering, and design side did. They also tended to generate more meetings and work for other people than was commensurate for their contributions.

We’ve also experimented with giving leads P&L responsibility for products and groups, but ultimately it was awkward because we don’t really want leads or teams focused on the loss or costs of what they’re doing — we just want to grow our core metrics and revenue in a healthy and accelerating way, and let Ops and myself worry about overall profit or loss for the company, costs of people and services, capital requirements, etc. We’re still at a stage where our primary goals are investing in growth and product excellence, I wouldn’t want a P&L concern to be a distraction from that, and that also takes us into the territory of different teams having “headcounts” of people they can hire for the year, or budgets set ahead of time and that they’ll lose if they don’t use, zero-sum accounting between teams and more balkanization you often see in larger organizations. When anyone thinks about P&L at Automattic, I want it to be holistically and with a long-term view, not for a single team or product.

It gets backs to the fallacy we talked about and agreed to avoid at the [WordPress.com leads] meetup, which is the business equivalent of Great Man Theory: the idea that a deficiency in the business or product will be solved by hiring someone senior to be in charge of that thing. Example: Automattic is bad at marketing, we should hire a CMO. (99% of the time when this is suggested it means an external person, because if anyone internal was good the problem wouldn’t exist.) It’s an easy thing for anyone to fall into, you can see it in [a recent internal thread].

This must work sometimes, because it seems to be a near-universal affliction of VCs on startup boards. It also is a little bit of a bikeshed, because while it can be difficult to understand or feel like you can have an influence on something fundamental to the product, like say the signup flow, most VCs have large professional networks and can have long and vigorous discussions talking about potential people who are executives in a given area and their first or second degree connections to them. Of course, like many of us, VCs are consumers of tech media which tends to ascribe all the success of an organization to a single person (like Sheryl Sandberg for Facebook not falling apart, or Adam Bain for revenue at Twitter). However often the problem has root causes more fundamental than a single person could shift.

I subscribe to a more environment-driven approach, that if you break down a problem into its component parts you can address them individually, often with relatively simple next steps, and build things from the ground up, rather than the top down. If you can’t do that, then it’s best to be candid that the area is not a priority and make sure that’s in line with what you’re focusing on instead. In this process leaders will emerge or if the effort matures to a point where one joins as a new hire he or she will have the resources, groundwork, and environment to succeed.

So in summary: always go back to first principles of decisions. Hires are seldom panaceas. Someone being successful in a role at another company doesn’t mean they actually did the work, or were the cause of the success. If there’s an area you’re weak, try to figure out the root causes of why you’re weak, and where possible try to improve the environment that creates the problem before pinning the turnaround on a “Jesus hire.” When you improve the environment it makes it much more likely a new external hire will do well. The majority of success or failure is a result of the environment, at least as much as the individuals involved.