San Francisco feels like a small town sometimes

I like it here. I haven’t written much about my transition to the Bay Area, mostly because it’s been quite a year of ups and downs. But I do enjoy it and am happy with the decision, mostly because of the people. 

I’ve had more interesting and fun conversations here with random strangers than I’ve had in any other city. People get jokes. They are ready to engage. They seem to be having fun. I like it. 

I’ve also started to recognize people; not just the nice people who make me coffee and sandwiches, but people I see on the street. In the last year I have taken pictures of at least five people who I’ve seen again. I don’t mean people in my neighborhood or near my office, I mean random folks I saw on BART or on the street.

The impetus for this post came from a woman standing next to me on the train – right now – whose photo I took months ago. I took it because her green travel mug matched her green jacket and it looked kind of cool and commutery and my intention is to take photos and decide later what to do with them, rather than hem and haw and miss the picture.

I think I took two, and in the second she is giving me a definite “why are you creeping me?” hairy eyeball. I should post the picture here but that would require a lot of scrolling and it wasn’t in focus.

Is she reading this over my shoulder? I would if I were her. I totally look at people’s screens on BART. A few months ago I watched a guy post comment spam with embedded… scripts… or something. 

Also you’d be amazed how many people on the train are reading porn novels on their devices.

San Francisco is one of the world’s great cities, but only 837,000 people live here, nowhere near the size of the mellifluously-named Raleigh-Durham-Chapel Hill Combined Statistical Area “CSA”, with its estimated population of two million plus.

I don’t know how to end this post and we’re almost at my stop so I’ll just say there’s a Japanese transsexual dressed like a schoolgirl standing near the train door, posing and checking herself out in the reflection of the window and a guy dressed in, you know, men’s clothes trying really hard to figure her out. 

I should probably take a picture. 

I’ve always been fascinated by radical transparency as a corporate communications philosophy

I’ve had a lot of roles in my almost 35 years of working. I’m still using lessons I learned as a fry cook at Golden Corral at the age of 15. But I don’t have an MBA and have never really studied business, just gotten “on-the-job training.”

Wait. On-the-job training.

A lot of what I’ve learned about managing people, for instance, came from making mistakes and missing really obvious things.

For instance, you can never communicate too much. No matter how clear you think you’ve made something, some smart, dedicated, valued member of your team has the wrong end of the stick. And as the manager, that’s your fault. 

I’m thinking about this because I started listening to “StartUp” last week, a podcast about the genesis and early days of Gimlet Media, a company that makes podcasts, including “StartUp.”

All fun meta stuff aside, it’s the fully-documented, evolving story of a new business trying to get off the ground, grow and scale. I’m learning a lot, and it’s fascinating to hear their conversations, analysis, self-doubts and fears and all the stuff that usually goes unsaid. 

Moreover, you can see the benefit that the podcast itself has had for the business itself. Talking openly about getting funding helped them get funding, despite the fact that they were very open about the challenges they were facing and their doubts and fears. 

Or did it help them get funding because they were open about their challenges and doubts and fears? I think so. Although I’m not an investor, I certainly trust them more after hearing them address their issues realistically, without hype or bluster, and work through them. 

I’ve always been fascinated by radical transparency as a corporate communications philosophy. I’ve been lucky to mostly work for companies that made genuinely good products. Most of our marketing struggles have been how to capture the value of what we did in terms that could make a good headline or fit on a postcard.

That’s hard, but it’s a separate challenge from building a great product. Great products have been brought down by bad marketing, and the obverse is even more common. 

I’m thinking about this now because at my new job, at a startup, I’m trying to find the best way to encapsulate the vision, passion, knowledge and commitment of our founder/CTO and our CEO, as well as our product’s genuine excellence.

When the two of them sit down with customers or analysts, they tell a fascinating, compelling story. But it’s hard to turn it into a strap line and three circles on a slide. “Maybe they’re just better at what they do than I am.”

What I really want to do is put a camera on them whenever they get talking and show the process and the debate. Am I putting too much trust in the marketplace, to hope transparency and honesty would trump a clever slogan, a made-up word with a trademark symbol and a big ad budget?

What do you want to be when you die?

I’ve always envied people who were driven in their careers. Not just the people who knew they wanted to be a doctor or a pilot at the age of 10 and made it happen, but the people who seem completely focused “or “laser focused” as we said at my last company”.

I envied them because I’ve always had to work to stay focused, to keep on with the project plan after the excitement of the brainstorming and planning was over. I’ve learned how to do it; after all I did manage to co-write a book and build successful social media and content marketing programs in four different organizations so far. “My best best practice is to make sure I always have a detail-oriented, focused, Type A planner on my team.”

As I get farther along in my career, I understand things I didn’t understand before. I have a better idea of how I work and what I need to do to succeed. I also have a better idea of where I provide value and where I’m happiest. I need to be in amongst the action, and also part of the strategy process. That seems to be easier to accomplish in a smaller company.

I also know I’m not willing to make the sacrifices some people make to advance. I’ve seen first hand what it takes “and what it takes out of you” to be a senior executive at a large company. I used to think I wanted to rise to that level. Now I know I don’t, and probably won’t, regardless.

This has been a difficult and reflective year, filled with personal loss and grief, as well as professional. So many things are different in my life than they were a year ago. But going through all this has helped me get a better understanding of what I want and what’s important to me.

My father’s funeral was filled with people who loved and respected him. He touched a lot of people with his generosity of spirit. That message came through loud and clear, especially in contrast to the people I’ve encountered in my career who seem so willing to put their essential humanity on hold for greater success at work.

I hope you don’t do that. If you do, ask yourself why. If you have a good answer, and it really does sustain you to work like that, okay. But I’ll worry about you.

There’s the “apt” cliché that says no one ever wished on their deathbed that they’d spent more time at the office. True. But I wonder how many people on their deathbed, or worse, in the many years between retirement and death, wish they hadn’t been such an asshole.

We’re entering a very strange era of supranational power.

I just saw the headline, “Coca-Cola Calls for FIFA’s Sepp Blatter to Step Down Immediately.” The article mentions that Visa, InBev, McDonald’s and other huge, multifaceted, multinational organizations have joined the call for his ouster. “Love that word.”

Depending on how you look at it, FIFA is as big and powerful as a country. So are those corporations. Blatter’s power rivals that of many elected leaders of smaller countries, even if he doesn’t have an actual army under his control.

The older I get, the less I like dystopian visions. But at the same time, I also see more and more parallels to, for instance, the fiction of William Gibson and others who got started in the cyberpunk genre. One of them “can’t remember who” imagined a future where we are automatically sued for traffic infractions by connected bots built into passenger cars. The suits are settled by both sides’ computers, for a few dollars. In this novel it happens so often and quickly that it’s hardly more than an annoyance. Doesn’t sound too farfetched anymore, does it?

Neither does the idea that the leader of a global sports “read that “commerce”” conglomerate could behave like a tinpot dictator, only to be taken down by an alliance of corporate sponsors flexing their economic muscle to prevent the devaluation of the brand they’ve invested in with their advertising dollars. It’s just gonna get weirder.

Tech companies are basically paying prospects to listen to their pitches.

I’m no economist, but I’m not too worried about all the current “bubble” talk. Yes, valuations are high and there’s a lot of money around, but I also see a lot of companies — including a lot of the supposed “unicorns” “private companies with valuations over $1 billion” — that are building products that really do something.

Yes, there are a lot of dopey apps that do dumb stuff no one really needs, but as far as I can tell they aren’t dealing in big money. They come and go without too much impact other than on their employees.

Whether or not Uber is worth $50 billion is another story, and by that I mean, to use a high-finance term, WTF?

But regardless of whether or not the current crop of tech companies can provide lasting value to customers, employees and shareholders, VC money is causing some weird stuff. Real companies providing serious software to meet real business needs are getting big chunks of money to build and grow. Nothing wrong with that, but it also means companies are spending money in ways that previously only established companies would have tried. These days you can grow and scale and market yourself like a big shot on somebody else’s dime. And there are a lot of dimes around.

For instance…

One of my colleagues got a postcard before Dreamforce promising him an Apple Watch if he came to another tech company’s booth for a demo. Not a chance to win an Apple Watch. An actual watch, just for him, just for watching a demo. He went, he watched the demo, he got an Apple Watch. He didn’t misrepresent himself, his interest in their product or his role in the decision-making process.

I’ve also heard of another company at Dreamforce who made “wanted posters” with the names and photos of CMOs they wanted to meet. They handed them out at the CMOs’ company booths and promised the booth staff 50 bucks if they brought their CMO by, essentially offering a bounty. If the CMO came by of her own volition, they handed her a hundo.

I now work for a VC-funded tech startup, so I’m not pointing fingers or decrying, you know, anything. But I also work with seasoned business people. We seem to be keeping an eye on our money, which I appreciate. The big-money shenanigans seem strange and unreal to me, and they make me uncomfortable.

Bottom line, I’m just bitter I didn’t get an Apple Watch.