Five people that I wish I had something more interesting to say to

One of the things I pride myself on is knowing a little about a lot of things.  I can generally strike up at least a brief conversation with anyone—which helps a lot when your job is basically to talk to strangers. 

I do, however, have a huge amount of respect for anyone who has deep expertise in an area—who has found something they want to focus on and done the deep dive.  I like listening to them and learning, but sometimes feel like I’m a little short on things to contribute.  It doesn’t bother me terribly, because I’ve decided I’d rather be able to connect to a lot more people and help them connect to each other, cross-pollinating ideas.  Still, every now and then I run into someone I wish I had more to say to, because I find them interesting, incredibly thoughtful, and would love to have the background to be able to do a deep dive with them.  Here are a few:

Equity Private/Finem Respice:  Having been in and around the private equity world for almost ten years now, I found this blogger’s takes on a middle market boutique banking firm to be spot on—and highly entertaining.  She occasionally, and then more frequently, mixed in incredibly thoughtful economic analysis, quickly becoming a must read.  The only issue was, I had no idea who she was—no one does.  She moved around a bit, posting as part of Zerohedge, and I’ve been lucky enough to get to jump on instant messenger with her on occasion.  A former DJ in her spare time, she even treated me to a lifestream mix right off her laptop, but still, no clue as to anything about her identity.  Either way, I was pretty overmatched in terms of being able to talk about financial economics.  These things just don’t hold a ton of relevance when you’re funding two hackers in a garage somewhere, and so it wasn’t a priority for me to keep up with.   Still, I think she’s incredibly brilliant, always enjoy reading wherever she pops up, and remain a fan.

Marco Arment: Marco is a driving force along with David Karp behind Tumblr.  He’s also the creator of one of the most elegantly designed iPhone/iPad apps out there—Instapaper, a thoughtful and simple approach to the habit of reading the random articles you encounter throughout the day.  He’s a big fan of Apple and also, perhaps infamously, doesn’t like comments:

“I’m fiercely independent, to a fault. I dislike relying on anyone for anything, and I’m not a very good “team player”. I don’t see my writing as a collaborative effort, and I don’t see my site as a community in which I need to enable internal discussion via comments.”

A lot of the reason why I don’t have a ton to say to him, other than the occasional and probably annoying “Hey, nice post, raising money for Instapaper yet?” e-mails, is because we either don’t necessarily agree on a lot, or feel as strongly about the same kinds of things.  (Hard to get into a deep product conversation about the iPad case when the lone Apple product you own was given to you by someone just to use for work.)  However, a read of his blog depicts well considered intentionality, and I respect that.  Every little feature on Instapaper is either there for a reason, or the best he can come up with until he has time for a better fix.  His relentless and unyielding devotion to a great consumer experience is Jobsian.  Being a PC, it’s fun for me to watch and learn.  It would undoubtedly be a great experience to be able to support what he’s producing in a deeper way, but until then, I’ll just remain a fan of his approach on the sideline.

danah boyd: If you want to cut through the superficial media soundbytes about what the kids are doing with their rock and roll and social networks, read danah.  She knows it through and through because she spends a ton of time with youth and studies their online behavior.  Her logic is complete and driven by a deep passion to shed light on and help get youth behaviors understood by those whose actions and policies affect them.  I always go out of my way to say hi to her at various conferences we run into each other at, and grab a hug, but never really have a lot to offer that would make her think I was particularly thoughtful. 

Hilary Mason: Hilary is a friend and I take every opportunity I have to through a shout out her way.  I was lucky enough to get to work with her for a year and a half at Path 101.  What I love about Hilary is that her passion is not specifically for science and data, but for sharing knowledge, making data make sense, making it usable and teaching others.  While my softball playing friends might think me a bit geeky, Hilary falls way on the end of that spectrum, in a good way.  Sometimes, I’ll joke about how Hilary might be the kind of person to write shell script that bakes cookies according to some kind of algorithm—only to learn that was actually a project she did with her students.  Usually, the extent of my engagement with her on a product like that is to just eat the cookies—so hopefully she doesn’t mind me around for my relative luddite comic amusement or as a deposit for baked goods. 

Joshua Schachter:  Joshua was one of the first entrepreneurs I ever got to meet at Union Square Ventures—and he wasn’t at all what I expected.  He’s a bit prickly in his demeanor—often telling you that a particular idea is stupid.  Most of the time it’s because the idea is, in fact, stupid.  You just don’t normally expect anyone to just come out and say it so matter-of-factly like that—but also without personal judgment.  He’s also very much like Marco in his attention to ideals of user experience, and I’ll never forget him saying that “Anyone can come up with good ideas—but few people are good at reduction—crossing off all the unnecessary features.  I’ll often run into him at conferences and after the usual pleasantries, fall into the trap of saying, “Yeah, a lot of these panels look interesting,” and get a response of, “Really?  I think most of them are crap.”  The truth is, I probably didn’t look at any of them yet—but that’s just something you say when you make idle conversation.  Joshua has no idle conversation setting.  He’s purposeful, thoughtful, and he’ll keep you on your toes.  He’s also a foodie, and is how I discovered the Shake Shack and Mizu while working in the Flatiron area.

So there you have it…   I’m not sure what the point of this post was.  It just popped into my head.  The common thread, from what I can tell, is my appreciation for thoughtfulness and purpose. 

Seems like a good opportunity to quote the Matrix:

“There's no escaping reason, no evading purpose, because we both know, that without purpose there is no reason to exist. It is purpose that created us, purpose that connects us, purpose that pulls us, that guides us, that drives us, that defines us, it is purpose that binds us.”

I may often be seemingly without specific purpose—but would argue that my own is to find others who have it.