Three March Things

Three things I’m bummed about:

DONALD: Prior to his victory, I darkly speculated that the silver lining of a President Trump would be the “it’s always darkest before the dawn” idea. That no amount of abstract discussion of topics would bridge our divide, that it needed to take human form and we needed to see the bad w/our own eyes before we could unite against it. It needed to get worse before it got better. History has proven this axiom over time, it’s just unpleasant. So I wait. It’s unpleasant. The divide feels larger than it’s ever been, and on some days, overwhelming. I tell myself that this is exactly what it’ll feel like until the tide turns. You don’t see it coming.

DEBT. Long a bugaboo of mine, America’s debt is just horrific. Every single person who said any variation of “but Obama and debt” and blah blah, has a lot of explaining to do. Countless Republicans used “Obama’s spending” to skewer him and as cover (take from that what you will) for hating on him. Well, the deficit (and therefore the debt) is looking pretty damn bad right now. We all have our mindsets and a key framework of mine is a dislike of leverage and debt. I prefer stability and piece of mind over luxury. America has chosen leverage. This won’t end well. America (and our enablers) will likely pay a high price as this eventually approaches the end game.

DEPTH. The recent coverage of Facebook’s casually sloppy/stupid privacy mis-steps was just another reminder of how little depth there is to our discussions and understanding. One of the most frequent notions was that FB “sold” user information. This is, of course, stupid. They are guilty of a number of sloppy, stupid, and bad oversights here — but selling user information isn’t one of them. They created policies that they didn’t enforce (and maybe had no idea how to even do so) and have been much to casual with the really sophisticated tools that they’ve built. But the public understanding seems largely superficial and, often, mistaken. This is true for lots of things. From Trump to the details of policy, actually going deep and understanding building blocks and the heart of matter seems to not be en vogue.

Three things I’m psyched about:

TECHNOLOGY. It’s exciting that I get to make my living at the nexus at this. Whether it’s a startup that I’m working on or an investment — emerging technologies and their commercial applications continue to energize me. Genomics, battery, general software, blockchain, mobile devices, AR, the list goes on and on. So much cool stuff here. I can’t escape the idea that so much great stuff is on the horizon, we just need to not mess up the world too much so we can enjoy it. I dunno.

CONTENT. TV, movies, books, long magazine articles, podcasts, oh my. There’s so much great content out there and I just love it. Even with loads of time on my hands, I don’t have enough. The Three Body Problem trilogy is the latest book that’s just swallowed me up whole. Atlanta and The Americans is back on TV. My MoviePass card is not getting used enough, etc, etc. It’s enjoyable, a pleasant escape, but the best stuff is also creative fodder for the rest of my thinking.

HEALTH. With so much macro stuff (world news!) that I can’t control, I’ve made a turn inward as I’ve been thinking more about my health. This means focusing more on what I eat (a gradual evolution!) and on how I take care of my body. The latter is something that I’ve done in fits and starts, but usually with some external goal (almost always to gain weight). Now it’s just to have more energy, feel good every day, and to create a foundation for longer-term well being. This means eating better, flexibility/core strength, and cardio activity to get my heart going.

Life reading

Byron Wien

The Life Report: Byron R. Wien

What a fantastic read! He’s an incredible market commentator and is featured in Barron’s this week. Loved the writing and his insights. Selections/reactions:

“Eventually I developed the necessary skills and became a partner of the firm. The lesson here is that you shouldn’t try to decide what you want to do for the rest of your life when you are a teenager.  Pursue your passion in college and the rest of your life will take care of itself.”

This is both common advice and also somewhat controversial. I’ve heard it argued that this only works if your passion is in something w/obvious commercial value. I don’t agree. In today’s world — with so much rapidly being automated and everything rote eventually to be absorbed by the borg — original thought, creative expression, and innovative thinking will be what earns value. I find it hard to see how one stumbles into these things without deeply caring, and dedicating oneself to an area. Working in an area well, without passion, without deep interest, seems like a fool’s errand. His advice is more valuable today than ever.

When giving career advice to young people, I tell them there is a perfect job out there for everyone, but most people never find it.  Keep looking.

Yes. I so agree with this. Now that I can afford to be selective with what I do, I spend the most time thinking about fit. Of late, it has certainly served me well. I only wish I grokked this earlier. I don’t see how this isn’t universally applicable.

In my job I’m expected to understand what is happening in the world and to identify secular change.  It seems clear that the United States and Europe are mature, overleveraged economies with dysfunctional governments.  Since growth will be slow, unemployment will be high and the standard of living for many people will decline.  Opportunities for young people will be fewer than the ones I could take advantage of.  There will be more social unrest.  I was born in the Depression and lived through the glorious years for America after World War II.  The future for these born now is not so bright.

I agree w/his general thrust on the nature of Western economies. But I disagree w/his final conclusion. I would amend as: The future for those being born, in a future projected forward as it looks today, is not bright. If one were to just project forward, I agree with him. But major advances in health, travel, energy, etc — could, of course, radically restructure our mode of living and economic system. In such a world, who’s to say creative freedom and the ability to find meaningful work won’t be greater?

Not having children is one regret, as I said.  Another is that I am estranged from my older brother to whom I loaned a large amount of money when my financial circumstances were marginal.  He never paid it back and lied to me throughout the process.  We talk only on our birthdays.

This struck a nerve. A question I’ve asked myself a lot of late: Can you see a regret coming and still do nothing to change it?

Fantastic read. Super interesting man.



Have you ever kept a journal?

I’ve got 15ish years with various incarnations. My first was a LiveJournal created in the dying light of the 90’s. It birthed a few friendships/pen-pals and lasted a few years before I nuked it. I don’t remember what I posted, but I’m confident it was properly self-absorbed, poorly written, and vapid.

I concluded that the public nature of LiveJournal was a problem and decided to kick it Doogie Howser style. Using the “.LOG” function in Microsoft Notepad, for four+ years I memorialized my histrionic thoughts. Buried at the bottom of a box at my parents, in the rubble of all my x-country moves, is a CD-R w/the files. It’s been 7ish years since I’ve seen them and I’m incredibly curious of what I’ve written. One thing I know is in there: weeks and weeks of entries about the first girl to break my heart (umm…kind of mortified to read those). Next week when I head back for Christmas, I’ll poke around and see if I can find those files. Because, after all, there’s nothing like reading something, only to find the author utterly foolish, petulant, and unsympathetic.

I have terrible handwriting. Still, I was carried away by the romantic idea of journaling in a moleskin. Over the course of a decade I’ve nearly finished filling two editions. Some weeks feature multiple entries, while other periods have gaps of multiple seasons or even just a single entry for a year. Some of my most painful memories are in those books. The writing so visceral, it feels like blood on a page. When I’m nostalgic and foolish enough to look back, I might only get to read a sentence or two before I have to put it away.

Since June I’ve been using a journal for the Mac & iPhone called DayOne. I adore it and have been writing almost daily. This has been my most regular period of journaling since summer of ’02.

My journaling has totally been worth it. It’s how I make sense of the jumbles of feelings in my mess of a head. It’s how I call bullshit on my self. I like to think that I’ve evolved so much. That, over the years, I’m so much more sophisticated, smarter, and world-ready. Yet wading back into the journals always dispels this idea. So much repeats: tone, sentiment, struggles, joys. I don’t like to think of myself as predictable, but the truth is on the page. Often in really shitty handwriting.

Note: This was the first note I sent out to my email list in 2014. Subscribe here.

Life Personal reading

creativity, inc

Great passage from our latest company book club selection, Creativity, Inc:

Hindsight is not 20-20. Not even close. Our view of the past, in fact, is hardly clearer than our view of the future. While we know more about a past event than a future one, our understanding of the factors that shaped it is severely limited. Not only that, because we think we see what happened clearly— hindsight being 20-20 and all— we often aren’t open to knowing more. “We should be careful to get out of an experience only the wisdom that is in it— and stop there,” as Mark Twain once said, “lest we be like the cat that sits down on a hot stove-lid. She will never sit down on a hot stove-lid again— and that is well; but also she will never sit down on a cold one anymore.” The cat’s hindsight, in other words, distorts her view. The past should be our teacher, not our master.

Life Personal Technology

stimulus withdrawal.

A few days ago I decided that I’d start 2014 with a pretty simple change: To seek less stimulus. I wrote a blog post and a status update sharing my impending Facebook absence. I sent an email at work to no longer expect immediate email responses. The changes ended up being:

  • No more Facebook.
  • Conditions allowing, moving to limited windows of checking & responding to emails.
  • Limiting  Twitter + daily consumption of news, RSS, etc  to a couple of slugs a day.

Why? Listed in order from most tangible to the most abstracted:

1) Productivity – I’ve chosen to give up these things so that I can be more productive. I feel like I can use time better, specifically towards more directed tasks and projects. I’ve ended every year not accomplishing as much as I had hoped and with a vague notion that I’d left “opportunity on the table.”

2) Stillness – Reducing noise. Constantly checking email, twitter, facebook, espn, techcrunch, et al, did satisfy my curiosity and staved off boredom. But I was never allowing my mind to sit still. Instead I was constantly feeding it stimuli, which caused to to feel constantly “on the go.” At one point I might have considered that a feature. Today that’s very much a bug.

3) Substance – Finally, as explained in my previous post, I did this because I have a number of doubts as to the “realness” of my virtual relationships. Going further, I wonder if rather than being accretive to my life, if they actually hinder the progress I’m trying to make in being a better, happier human.

Since the new year, I’ve read a few blog posts from others trying something similar. Clearly these feelings go beyond me. I don’t think I’m doing anything complicated. I’m just trying to increase the signal-to-noise ratio of my everyday using the most basic of concepts: focus. I’m trying to stay focused on being present in the moment. It’s an ancient and probably overused phrase. My only resolution was to focus more on whatever I chose to experience that day. That partially manifests itself in that above list.

Making this change obviously comes with a cost. After all, nothing’s free. I’ll see many less news stories, pieces of market data, internet memes, and all the rest, making me less well-informed. I’ve always thought my consumption of all this information was a key strength. That my creativity was fueled by connecting the frameworks of all these disparate topics. Yet I think this is tradeoff is worth it. What I’ll gain from thinking more deeply on fewer projects, by being more present in each of my daily experiences, and having more whitespace, will result in its own kind of knowledge, creativity, and happiness. I guess we’ll see.

Life movies Technology

The past is just a story we tell ourselves.

Prodded by the overwhelmingly good reviews, I saw Her last night. The most positive reviews called it was the best movie of 2013. The concept of a human falling in love with a smarter version of Siri sounded kind of ridiculous. But since writer-director Spike Jonze is uber-talented and the trailer looked good, I went.

It’s actually not a movie about the future or technology. It’s a classic story about being human: Relationships, connection, loneliness, struggling with life, and, most obviously, love. It’s funny, beautifully shot, features terrific acting + pacing, and works off a great screenplay. Loved it.

There’s a particular line in the movie that I was really struck by:

The past is just a story we tell ourselves.

(after some googling, I’ve discovered that Chuck Palahniuk, among others have served up some variation of this insight for years).

Like all things, there’s great variation here. Some people are better than others at not being pre-occupied by their past and letting their today and tomorrow become derailed by it. I am not one of the better people. Anyway, I loved this line because it distilled the truth that the past isn’t merely a set of facts or past events that is black and white. We imbue the past with the weight of story. Like a wound in our mouth, we then incessantly tongue that story  – feeling its texture, its shape, its pain, wondering if it’s still there…if it’s still the same. We don’t realize it’s a story. We accept the past as fact — it already happened…it had implications…of course it is what it was — when the past is actually a concoction of fact and emotion. The past is merely facts, like you and I are merely atoms and molecules.

It felt so welcoming. To hear the line, was to ease into a warm, freeing embrace. I walked out of the theater mesmerized by it.

I’m looking forward to more people seeing it so I can discuss.

Life Technology


I gave up Facebook for the first few months of 2012. Cold-turkey stopped reading my feed + posting. In the lead-up to my summer of traveling, I got back on the Facebook-train and probably posted too frequently. Since then I’ve settled into a steady routine of trying my best to “like” pictures of friends’ children , important events, etc. I basically stopped posting, though. I found it hard to untangle my motivations.

I feel like I have reached a point of being paralyzed by self-consciousness: Why am I posting this? Who am I trying to impress? Why do I want/need people to “like” it?

I’ve loved and hated Facebook. I’ve hated the distraction of it. I’ve loved the quick hit of seeing a familiar face. I’ve hated that twinge of jealousy that might strike from a random post. I’ve loved feeling a bit more connected to distant family + friends.

Tonight at 11:59 PM, I’ll start 2014 on another open-ended Facebook break. I will miss the cute photos of my friends’ kids and such. I will definitely miss those “in-between” moments and stories.

I wonder, though, if this might be a healthy thing for me. Maybe Facebook is like aspartame or saccharine. It feels sort of like a connection to the people I care about. Sort of like Diet Coke tastes sweet-ish. But without being lulled into this (false?) sense of connection, might I be more likely to try and create real connection? To send an actual substantive email? To make a phone call? To physically be present with the person? Is Facebook like the empty calories that just make me feel like I’ve eaten something filling and nutritious?

Like everyone else, I have hopes for 2014. I’ll use this arbitrary point as a reset for all the little ways I’d like my life to be different and that I think can be a better human. No big changes or promises for me. Instead, a handful of little tweaks, dropping Facebook among them.

Goodbye for now, Facebook friends.


RIP Alex Calderwood

About 18 months ago I was in the “green room” for the Charlie Rose show. I was in NYC working on a friend’s book launch. While he was out there taping with Charlie, I was backstage with the famous folks who were about to be interviewed, including James Fallows.

After a few minutes of excitedly chatting with James, I noticed a guy sitting alone, off to the side. He had a mop of curly hair and a quiet, unassuming presence.  I went over and introduced myself.

Turned out that unassuming guy, Alex Calderwood, had started the world-famous ACE hotel chain. He had been at a party w/Charlie and had mentioned it’d be cool to see the show being taped/sit in the green room. Charlie Rose, apparently, being great, made it reality.

We talked for a good 3o minutes. About how he started Rudy’s, the ACE, other projects. We talked about my run for Congress, working in tech, being on The Apprentice, and other randomness. It was a great easy, natural conversation. We exchanged cards.

I just searched my gMail and saw that we had seven emails chains since. He was looking at some potential deals in San Francisco, I was in town, and so we were able to get together for a drink (I had a drink. He apparently had given up alcohol some years earlier). Afterwards, he introduced me to someone who was doing cool things in education reform, so I could help, etc. We met up a second time, when he had me join a business dinner with a wealthy Asian investor, just because. Both times he was a positive, inquisitive, and awesome presence.

In the course of our few conversations, my love of tea and interest in possibly turning that passion into a business came up. This past summer, I got a ping from Alex because he remembered that and wanted to see if I was interested in working together on a tea store in a location he had, etc. My heart wasn’t in it then — I wanted to go back into tech — and so nothing came of it.

I sent Alex a quick note in July when I was in NYC interviewing for my current job. It was my first note to him that I didn’t get a response on. We obviously didn’t connect. As I’ve passed by or been at the ACE since, I kept meaning to drop Alex a quick note letting him know I was here, so we could catch up.

30m ago, while feeding my Twitter addiction, I saw the tweet pop up “Sad news: Alex Calderwood, the founder/owner of the Ace Hotel has passed away at the age of 45 according to the Ace Hotel blog.”

I’m not exactly in shock – I mean, I barely knew him – but I am sad and really, really thrown. I’ve been lucky enough to not have to deal with a lot of death (yet). Less than a handful of times in my life. That hangs over me a bit: it’s coming. Death visits us all. Death is the reminder of the impermanence of all things, most notably, our lives.

I might not get tomorrow. Next week. You  might not either. Act accordingly.

Live your life. Treat others as you will wish, in retrospect, that you had. Act accordingly.

To Alex, wherever you are: I’m really glad I got to meet you. I hope you’re in a better place, at peace.

Life Personal

september 11th

Today is a day of grace.

It’s my opportunity to give thanks for the life I’ve been given, the love I receive, the beauty I see everyday, the suffering I’ve endured & survived, and the bounty of waking up each morning  to a day of wondrous possibilities.

September 11th is my yearly reminder of how precarious this beautiful thing that is my life is, and a reminder to not take it for granted nor waste it.

Life Personal

never waste your suffering.

“Never waste your suffering. … Suffering just happens, constantly and randomly, and if you don’t make anything out of it, then it happened to you for no reason. But suffering can also be the greatest possible invitation to transform — but only if you accept that invitation, and only if you go through a complete catharsis, and only if you actually change yourself because of what you’ve experienced. But that part is up to you. Only you can execute a catharsis in your own life. Suffering without catharsis is nothing but wasted pain. And you should never waste your pain, never waste your suffering. It’s powerful stuff, the most powerful stuff there is. Use it. Transform from it. Learn. Grow. Be better.”

Elizabeth Gilbert (eat pray love!) references the quote from Jim Maclaren, a man whose story is so incredible that it can hardly be believed.

I’ve long struggled to live in the moment. Still do. A perverse form of being present in the moment is to wallow in lows (or, I guess, to over-indulge in the highs). The trap of the lows is that it’s all to easy to feel like that is is all there is. The darkness, the misfortune, the cruelness, the pain, the suffering seeps into ever crevice and wraps itself firmly around every cell. It’s all-consuming. But, as Jim points out, it happens: constantly, and randomly. The choice is whether to examine it, to look at it, weigh it, and almost coldly have catharsis. Sometimes it’s to purge ourselves of the hate we’re feeling in that moment to get to forgiveness…to let go of self-pity to recognize the power we wield to change everything. Anyway: don’t waste your suffering. Don’t waste the doubt. Don’t waste your humiliation. Don’t waste your inadequacy. Don’t waste your fear. In a really perverse way, in a way that I barely understand, I think there’s as much beauty in it as any of the ‘good’ stuff.