Categories
Startups

Day 826 and Alignment

I think there is this persistent fantasy in startup life that people will always agree with your bets. We forget the discord of every hype cycle but it’s not always clear who is winning and what outcome is certain. Only hindsight is 20/20.

You do get occasional moments of vindication but it’s rare that they ever clearly overlap with a trend or a moment that everyone is paying attention. Media hype cycles and innovation hype cycles are not the same thing. Trust me I’m a pretty good publicist for a hobby.

Your deals aren’t always going to get attention though and a lot of founders want to keep things quiet so you can’t always talk your commitments.

This is a problem that investing has in common with fashion. I earned my stripes making shit cool for money. It’s actually hard. I call it the The Thursday Styles. The problem with tend forecasting is knowing what’s going to be trendy is a temporal bet as well as a cultural adoption one.

It’s a thing happening over time that is unevenly distributed. I learned that from William Gibson. Some of us live in the future but you can’t be too far out because then it’s just you speculating. You got to be right on the thing and on the timing to make any money.

It’s honestly way harder than it looks and anyone who is any good at taking a bet on what the future looks like has to take some variant of this bet. It’s probably why Dune is such a canonical text for nerds. He predicts the future dimly and is also a messiah time lord? Sign me up that sounds like venture capital to me. The sheer hubris of this comparison is honestly nauseating.

Like fuck all the way off you ain’t Maud’Dib. You’ve got to be very skeptical about the charismatic pull of a messiah my friends. That said I bet you’d believe me if I told you I was a Bene Geserit right? Anyways. My point is you don’t always get it right and you don’t usually get to take credit till the end. And mercenaries can co-opt anything. Your shit might hit the skids.

But sometimes one of your deals looks hot and everyone is paying attention and you get to feel like you were cool. You spotted the band. You saw the runway show. The media is hyped about it at the same time and your friends noticed on Twitter. It’s a nice feeling. And yes I invested in the Chroma seed round. I think Jeff and Anton are cool.

Categories
Emotional Work Startups

Day 825 and Papered

A bunch of stuff that has been in the works for me for a while all got papered in the last couple of days. If you read any of my zen poasting (misspelled for internet reasons) you’ve probably gleaned that I’ve had a lot going on. Stuff got resolved on time horizons as long as lifetimes and as short as a narrative cycle.

I’d like to celebrate some of the papering (two deals I worked particularly hard for over a long time horizon) and I’m sure I will do so at some point but everything is going by fast and I’m just so drained from the dance. I suppose it’s how you really know if you are living. It’s a lot to live through everyone’s ego death drives and I’d be lying if I said it didn’t take a huge toll on me. I don’t yet know how to pay these costs in anyway but energy yet but I’m learning. If I put hard costs on it motherfuckers wouldn’t like the bill.

I’m modestly less sympathetic to everyone else’s bullshit as someone in my extended family passed away (not getting into it as it’s not my loss) and that invariably makes every other problem look inconsequential. Who care about your feelings and your ego and your petty obsessions in the face of death. But also maybe you should care about them even more? Not my call to be honest.

I’m not really able to mourn with them directly but I feel the energy of the loss reverberating for my loved one. And I wish I didn’t want to discuss it at all but I do. Somehow death is the lowest drama aspect of my week. Actual death.

So if everyone else can tone the energy down a little I’d appreciate it. I will absolutely make sure shit is inked, wired, soothed, smoothed and otherwise handled. It will all get papered. Whether it gets celebrated or mourned is a matter of personal discretion and I’m all out of fucks as to what you chose. Just gimme a beat or two to breath. This isn’t what you’d call a nine to five job.

Categories
Startups

Day 816 and S Tier

I fancy myself as someone who enjoys playing games. I mostly play the great game but I enjoy a good stupid grinder. Pokémon Go, Duolingo, and Fitocracy all appeal to my sense of hard work mattering.

But, of course, games have exploits. Some of them are significant. Sometimes leveling up is just a matter of getting lucky. A side quest dropped you an s tier item and the game engine smiled on you. Yay!

Silicon Valley mistakes luck for skill pretty regularly. And we don’t take it that well when other people use the same exploits as us because damn it that’s just not fair!

So rules tend to get rewritten and the hacks get patched and the economy in grinder games reliably defaults back to rewarding repetitive work. It’s not that different from the real economy. Gamers want to know clever game play works but not as much as they want to keep the value of what they have earned. It’s a real tension those sunk costs! Even if starting over benefits you the tendency to cling is understandable.

You’ve got to know when to spot when an activity is worth more than the general perception. You used to have to do this sort of work on your own but thanks to the internet we’ve got cheat codes literally everywhere for everything.

Don’t confuse the fact that cheat codes work for the fact that grinding came be the right approach for the game you are playing. Sometimes putting in the work means being a team player is valuable. Sometimes you are the glass cannon. Sometimes your style of play will offend others. Don’t take it all so seriously that you cannot stomach making a move. What’s the worst thing that happens?

Categories
Internet Culture Media Startups

Day 815 and Kayfabe

Here is a mindfuck for you. Pretending works. The mimicry of the thing occasionally, though not mostly, can lead to having the real thing. Fake it till you make it” works if you’ve got a long enough runway to allow for take off. If you’ve judged the resources correctly is more art than science but you should still be able to do the math.

There are, of course, laws of physics to account for in all of this but your reality is more fungible than you realize. I wouldn’t try manifesting a whole fantasy world, but if you are Brandon Sanderson you might have a shot. That guy rocks.

In discussing whether it is better to fire founders or product managers on Twitter today I got to see a lot of the cargo cult culture of Silicon Valley coming off a high. A lot of people can perform innovation and we’ve maybe even got it down to being well liked by financial markets. But sometimes you actually do have to go and do the thing. And you can’t fake it.

If you aren’t familiar with kayfabe, it’s a term used in wrestling. It means you don’t break character loosely. You keep the secret even if everyone is in on it. You can take things a bit too far and the blending of fiction and reality has now given us a reality tv president.

But what happens when you don’t make the jump? Does reality crash in? Will the market punish you for not delivering on a convincing enough value proposition? Do you have to keep your ambition within some scope that can exist in our agreed upon reality? Yes of course. Fuck you it’s called civilization. But every once in a while someone goes from vapor ware to the Revolution. Don’t be so sure you can spot the difference though. Kayfabe doesn’t just fool rubes.

Categories
Internet Culture

Day 805 and Legibility

Being inscrutable is a tactical asset in our extremely online age. As more informational influence campaigns are waged, it becomes easier to invade your headspace if you are too predictable.

I’m not saying that being predictable isn’t worthwhile. If you have a firm foundation of philosophy or religion that dictates a stance sometimes you just have to own it. I’m a libertarian and I often walk the line of what I consider to be foundational beliefs in the value of other people’s freedom in relation to mine.

But I also live in reality where the grey of living in a civilization is a lot less clear. Anyone who doesn’t admit to this fundamental tension is untrustworthy as far as I’m concerned.

This of course makes me legible. It is one of the buzzwords in my favorite online spaces. It is the art of how we make ourselves legible to others such that we can see and be seen. I rather like this philosophy overall.

But I am also quite sure that if you give someone an opening to fuck with you they probably will. It’s definitely a risk to be seen. It makes you a target. But it’s also how you become a beacon. So it’s an over under decision on how much you care about other people attacking you is up to you. But if you open about experimenting with life and how little you know it almost always turns out alright.

There is a theory of public relations, much popularized by Steve Bannon and legal discovery, called flood the zone with shit. And sometimes not giving your enemies a sense of who you is because you are always in process of becoming more and bigger and inscrutable and then suddenly you are in the Heart of Darkness.

It was the stillness of an implacable force brooding over an inscrutable intention

Joseph Conrad Heart of Darkness

So everyone be optimistic and find your people but remember everyone is going to be playing the same game. So I’d definitely recommend you don’t cheat and play the long game.

Categories
Emotional Work Startups

Day 792 and Level Ups

I know I am courting a bit of a crash tomorrow because I can feel just how much energy this week took. But I am feeling emotionally like I leveled up. I looked at a few of my emotional patterns this week pretty head on and redrew some boundaries. And this always improves my work performance.

The upside of journaling your thoughts and emotions is you have a back catalog of your own thoughts to compare against your eventual conclusions. You can look back and spot patters in your thinking and tie them together. Writing everyday can be excruciating but I never regret having done it.

I have to always remind myself that it takes a fair amount of effort and a high tolerance for being wrong in public. You have to get used to people disliking you and finding you distasteful. People want to put their emotional response onto you and the hard work of being an adult is not accepting what isn’t yours.

If you can tie that kind of self reflection into your professional life you get all kinds of unexpected level ups. You tell people about your own responsibilities and they trust you with theirs. You get to build great things together by building on shares humanity. The best business relationships I have are the ones where we understand what value each of our personal lives brings to counteracting of own limitations and blind spots. I’ll always work with someone who leads with their humanity first. Big visions get worked out together by trusting each others talents.

Categories
Chronic Disease Travel

Day 791 and Bathing Suits I’ve Never Worn

I’m on maybe my third or fourth trip to a warmer climate where I’ve brought a Norma Kamali bathing suit. I bought it on sale from Net-Porter as I’d always wanted one of her classic one pieces. I’ve never worn it.

For the casual reader, I have a chronic autoimmune disease called ankylosing spondylitis. It’s an inflammation condition that affects my spine and is aggravated by heat & humidity. Any temperature above above room temperature, give or take 72 depending on the humidity, starts to swell my tissues.

It’s well controlled with drugs but environmental factors can quickly spin up a bevy of symptoms including pain so debilitating I can’t walk. It’s one of the reasons we moved to Montana. I can live a semi-normal life so long as it’s cold. I spend most of my days laying flat in bed or in a zero gravity chair. My disability has become one of the super powers I use to propel my investing alpha. Because what else do you do with your time if you can’t leave bed except monitor financial indicators and chat with founders?

But back to the bathing suit. The black halter swimsuit has turned out to be entirely an aspirational garment. It’s still got the sanitary sticker for the crotch on it that says remove before wearing. I left it in and it’s become the not so subtle reminder that I may never enjoy a beach vacation again. It’s simply beyond my grasp unless I want to pay an obscenely high cost in pain and immobility.

I dutifully pack the Norma Kamali suit on each trip with a warmer climate. I’ve taken it to Miami, Texas, the Mediterranean and Mexico now. For this trip to Puerto Vallarta I packed a second bathing suit. It’s a striped bikini.

I had a fantasy that maybe I’d need a second swim suit as the other would need to dry if I swam every day. Oh what self deception we humans are capable of when it involves something we cannot have but want. I’ve never put the second suit on either. It also has the sanitary sticker still on it. It’s beginning to feel like they taunt me. Isn’t it funny that Julie still yearns to participate in the simple pleasures of life. “That dumb cunt” I imagine them murmuring as I pack.

My father loves tropical vacations. An adults only resort on a beach is his idea of a good time. And for his birthday, my brother and I very much wanted to give him what he wanted. Part of this is self protection as he often forgets to ask after other people’s preferences even if they are for something serious like a disease or disability. Better to avoid disappointment than know for sure. But also if we can give him what he wants why not make the sacrifice? It’s expensive for me energetically but I wanted to spend.

But it’s become clear I can’t make the sacrifices desired for the perfect fantasy family vacation. The bathing suit gets tossed in the suitcase with the knowledge that I can only manage one event outside each day. It’s usually a dinner or a chat.

Then I must sleep it off and work to recover. There is no space for pleasant relaxation on the beach in my body. The compressed Lycra slowly battling the expansion of my tissues as they swell overlapping with stuck lymphatic liquids would be torture. There is no joy to be found and no extra capacity to be eked out that might make the experience mimic the pleasure in a healthy body.

The fantasy is just that. A delusion I have about a life a lost and unlikely to be regained. The after effects of fertility treatments, IVF and living hard to outrun the vicissitudes of capitalism. I’ve accepted it as my lot in life. But it’s much harder to get it across to the rest of the world. And my fear that I’ll be left out and forgotten, that if I don’t fit myself into someone else’s life I’ll be abandoned. And so I rationalize that I’d be abandoned if I don’t at least try to bring the bathing suit. Even though going to the beach is a fantasy.

I hope my friends and family are able to meet me half way but I remain afraid that they don’t know how, or are unable to imagine what it’s like to live in my body. And it would be nice to be met halfway.

Categories
Emotional Work

Day 788 and Duty

I wrote about six thousand words this morning at 5am about seeing your family for who they are and asking that they see you in return. I don’t think I can publish any of it even though it is a very raw piece of writing.

Today is my father’s 80th Birthday. He’s a rare early Boomer from the Silent Generation and he had me later in life with his second wife my mother.

I’ve got a lot of feelings about our relationship. I love my father. Like all of us, he has committed many sins, some of them against me. I have committed many sins against him. We are bound by an elaborate set piece of inter-generational trauma that has shaped us for good and ill.

I am bound by my familial duty to respect and honor the sacrifices he made. I am here to celebrate his life. But my feelings on it are more than I could articulate today and believe me I have tried.

It is my most solemn wish for his birthday that he finds forgiveness for himself as he did absolutely everything he could and I’ll forever be grateful that I was given these rare gifts.

Categories
Emotional Work

Day 781 and Accelerating

I am accelerating into the turn that is my extremely busy life. The global weirding is upon us, as I’ve been predicting for more than two years publicly on this blog and even further back in the press and on Twitter.

I was initially afraid that I wouldn’t be able to keep up with a faster life. One reason we moved to Montana was to keep the pace of our personal lives calm and level so professional obligations wouldn’t overwhelm us. And yet as more and more obligations and responsibilities became part of my daily reality, I wanted to shrink under the weight.

But I am not shrinking. I am standing tall. Sure I feel like I’m failing every day and I hate the feeling that I could disappoint folks who have placed capital and trust with me.

I am however sure that over the time horizon I have set I am doing things the right way. Everything else is luck and repeating the positive daily habits that have produced results in the past.

I feel happy with the acceleration if I stop giving the fear any oxygen. I’m starting to remember how I used to wield my talents. But this time I’ve got the benefits of five years of emotional maturing from intensive family systems therapy. I see my old coping mechanisms and bad habits withering as I bring the full maturity of my emotional journey to bear.

If life is going to keep getting faster and faster then I suppose my only choice is to enjoy the thrill of acceleration and trust that I’ve done the work to stay on the ride.

Categories
Emotional Work

Day 775 and In and Out

I am a bit overclocked. I’ve written about it before and the language is useful so I am quoting myself to remind myself what needs to be done.

It will just take some time to let all the cortisol spikes drain out and the other sundry overstimulation issues to get back to baseline.

I am thankfully not experiencing any of the typical anxiety I have felt in the past when overclocked. I just feel tired and shitty and like I need to had off some of inputs to my team.

I’m noting this all here and keeping it short as I need to get in and out so I can get back to the business of recovery as I have so much to take advantage of in my life right now. And the only way I can do that is continuing to maintain the routines and rhythms that got me to this good spot in the first place.