Tag: Investing

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Startups

Day 840 and Do You Believe in Magic?

The glory of writing every single day is you start to build m records of your own life. You notice how much your own personal cultural history is syncretic. I’ll always be a fan of blogging because it’s got chronology at its heart. Sometimes it’s good to see how we evolved over time.

Having a written record is hard and often dangerous. You own a lot of work in progress that doesn’t necessarily reflect where you landed. And internet opposition research is fantastic at catching you in a former evolution. We call it getting cancelled. But if you get it right you have the receipts.

But if you are an honest broker of your bets you will admit when you get better and more complete information. The real magic of startups is that markets are often excellent teachers of how we are just dead wrong. And if we listen to what we are told we can adjust. And as the old saying goes the market can be irrational longer than you can be solvent. The reverse is true too.

Consensus reality is a bit magical. I called our fund chaotic because the process of getting people to align is magical but it’s chaotic as fuck. It’s studied but experimental. It relies on rules and the temerity to break them. It’s chaos magic. I wanted people to see a bit of the woo woo in our fund name every day. Technology and magic are just separated by layers of abstraction. Go read Charles Stross.

So I was overcome with delight when I saw Geoff Lewis discuss how startups are magical. An all time delightful addition to the genre of how does venture capital and startup growth even work? Fred Wilson blogged so Geoff Lewis could vlog. And he did it with verve while discussing Dungeons and Dragons stats. Also he’s team maxed charisma like me so I am inclined to like him.

The fun part is that he and I don’t really overlap except on Twitter. We’ve never discussed any of this. But our syncretic workflows had overlapped. It felt like a small ecosystem knitting moment. An alignment of metaphors and aesthetics. It made me feel damned optimistic and yes I do believe in magic. And I hope you do too.

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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.

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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.

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Emotional Work Finance

Day 824 and Ego Loss Aversion

One of my favorite cognitive biases is loss aversion.

The pain of losing is psychologically twice as powerful as the pleasure of gaining. The loss felt from money, or any other valuable object, can feel worse than gaining that same thing.

The Decision Lab

Isn’t it wild how much we hate loss? The pain of losing $100 is worse than the joy of finding $100. In behavioral economics “loss aversion refers to a phenomenon where a real or potential loss is perceived by individuals as psychologically or emotionally more severe than an equivalent gain.” I guess we don’t like to win as much as we hate to lose.

But we have to train ourselves to tolerate losses. Otherwise you’d never play a sport of any kind. And you’d be an absolutely terrible investor of money. So it’s clearly possible for some of us in some situations to get over loss aversion as we have professional athletes and money making fund managers.

But what if we have to address loss aversion in our own ego? How much do we hate to lose a part of ourselves? What if we stand to gain something significant by letting go a part of ourselves. I don’t think we can always predict where in our own sense of identity our ego will fight against loss.

They say the therapeutic process is just mirrors. You have no real sense of what anyone sees except as a reflection. Everything else is just our faulty sensory equipment. And imagine what a colossal fuck up you could make by ignoring what the mirror says and only relying on the faulty sensory data from your ego.

Stew on that a little bit and decide how much you really want to win and get back to me. Could be you need to see how much you hate to lose before you can see what you stand to gain.

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Startups

Day 817 and RIP SVB

I hadn’t expected to grieve the death of a bank. It sounds so preposterous. Who the fuck feels sad about a bank failing? But I am genuinely sad that the Silicon Valley Bank name doesn’t appear be living on with its new owner First Citizens Bank.

I guess I look forward to banking with First Citizen. They seem like nice enough folks. And maybe a bank is just a bank. But as I look back on the firsts that Silicon Valley Bank gave me I realize I will miss it. I’m sad they are gone.

The first check I saw with more than one comma was from Silicon Valley Bank. My very first company was acquired by a startup that banked with them. Ironically, right before the 2008 crisis was beginning to come onto the scene. I had a small window of fleeting security where I enjoyed a steady paycheck every two weeks with payroll done by Silicon Valley Bank. I remember thinking I was so rich. Even though I was super pissed my cofounder had a better salary than me as Silicon Valley culture dictated at the time that engineers make more.

If you are a fan of history then you will enjoy knowing that yes I did get fired during the infamous RIP good times affair. Thanks Sequoia! They were our main investors. Still I appreciated the opportunities as I was so young I wasn’t very good yet. I’ll forever have loyalty to my CEO for having treated me much better than I thought I deserved.

I also I also really loved the steady paychecks from Silicon Valley Bank. Now I think to myself why didn’t I take any pictures of it? Why don’t I have that moment recorded anywhere but my memory? Why am I now recounting this fifteen years later.

I’ll never get another check from Silicon Valley Bank again. I just didn’t have the expectations in life that I’d be the sort of person with a bank account with more than a million dollars. Let alone that I’d be in control of one and entrusted to do something responsible with it. Which has now happened multiple times at Silicon Valley bank over the years for me. Guess no one wants to have more than $250,000 in a bank right now though huh?

So goodbye Silicon Valley Bank. I’m so sad I’ve got nothing to remember you but. I didn’t take a screen shot of the bank app on the day Stowaway’s first round closed but I should have. I spent a lot of time in their banking application over the years running my cosmetics startups P&L. I remember being so proud to be the sort of person that even needed to deal with the bank. And I trusted Silicon Valley Bank with my employees because I’d seen it treat me well when I was an employee.

It seems so silly to mourn not taking a picture of a check or a screen shot of a mobile banking app but I don’t really know how to mourn a bank that failed. We failed them. They failed us. And it’s dead and I’ll never ever get a chance to do it all over again, and even if they are a villain, I remember when they were the hero in my life.

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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?

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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.

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Chronic Disease Internet Culture Media Politics

Day 803 and Killing Strangers

I’ve been one of those types that absolutely has no problem taking a shot at the Christo-fascists dorks at CPAC mincing words about eradicating trans people from public life. Fuck you, you fucking fucks, you absolutely would be fine if state sanctioned violence eliminated trans people. It’s not you being metaphorical or cute or whatever justification you used. It’s killing strangers.

I wasn’t any more amused when folks decided it was alright to discuss a cost benefit analysis of keeping the disabled alive within the context of state benefits. No thanks I am not interested in a mercy killing because I’m expensive. Oh it’s a mercy killing for children? Yeah no still good thanks. Fuck you Canada. Medicare for all sounds good up until you decide to put me on palliative care via the metaphorical ice flow of opioid addiction.

So you might imagine I am equally sensitive about someone making jokes about euthanizing people who pays their bills by investing in early stage startups. Oh it was just a joke about how Keynes didn’t like the rentier class? Hilarious.

I am just rolling on the ground laughing at your erudition. Yes, benefits of a classical education. Har har. It’s so much smarter than the CPAC guy who wants to kill trans women. Definitely smarter than those segueing to mercy kill sick Canadian children. Oh wait, no it’s fucking not you sick fucks. Stop killing strangers in your rhetoric for shock value and clicks.

Perhaps I could interest the Jacobin audience members in a trip back to the Opium Wars, funded by Franklin Delano Roosevelt’s grandfather, just so we understand the gruesome reality that the New Dealers saw first hand in their own family trauma. Or if we are pluming the depths of the historical animosity towards finance and it’s intense hypocrisy, I’ll send you back with a copy of my favorite conspiracy text Creature from Jekyll Island. Then we can have a nice big chuckle about blood libel if you make it back.

I cannot believe that I am writing about any of this social media blood lust but perhaps we could all listen to Marilyn Manson’s Killing Strangers together and decide that there is no clever or enjoyable way to advocate for the killing of strangers. That it’s not cute to joke about killing people you don’t know just to further your political or economic aims. I’ll try to stop joking about how it’s ok to punch Nazis.

I am baffled that I keep ending up in groups that become the target of the genocide curious. I know being a hysterical disabled white bitch is a pretty commonplace “kill them all fetish” and smarter minds than me can untangle how all roads lead to disability. Witches and bitches.

But I’m getting unsettled seeing how it piles up and I keep getting lined up in other people’s sights. I’m married to a Jewish man. I’ve got queer family members. And yes I make a living investing capital (that I raised from weirdos) into other weirdos. Don’t worry my AUM is small enough I can’t live off management fees. Ironically because I’ve got medical bills because I’m disabled.

If you don’t know what that means and you still want to kill m perhaps it’s you that is the psychopath. Just a thought. Not that psychopaths are bad it’s just that I’m worried you will act on it. It’s not always clear if we are the baddies but advocating for blanket euthanasia is probably a helpful marker. Just like as a baseline for civilizational norms.

Either way, I’m not letting any of you kill my queer disabled Jewish rentier bourgeois family members. I don’t care if you a Jacobin or a CPAC member or a pissed off narco-trafficker running Fentyl out of Toronto. If you want to kill me because I’m a stranger and you don’t want to hurt the ones that you love. Ok. But I’ve got no intentions of making it easy for you.

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Finance Politics

Day 802 and Vengeance

You can’t stare into the abyss without letting it stare back at you. And I did a little too much abyssal observation over the course of the weekend. I feel overwhelmed with grief. I saw in the abyss a roiling cauldron of rage and hate and fear and despair. And I saw my own grief reflected back. The boiling blood that demands punishment flooded the news.

I feel grief for the inner child who lived through the turmoil of past market dislocations. I feel grief for my father who suffered through the bankruptcy of 2001. I feel grief for my mother whose teacher’s pension was decimated in 2008. I feel all the pain and sadness and anger and unfairness. I feel it all in my own family.

He piled upon the whale’s white hump the sum of all the general rage and hate felt by his whole race from Adam down; and then, as if his chest had been a mortar, he burst his hot heart’s shell upon it.

Moby Dick

I see the desire for vengeance. I feel it myself. I never saw any kind of justice for my father or my mother. My inner child will never know that peace. And I will have to be an adult and accept the disappointment of a world where far too many little children suffer for sins of their fathers. Many of us pick them up and carry them on. The churn is largely amoral and uncaring.

I see how satisfying it must be to give in to Ahab’s roiling anger. I saw many hot heart shells bursting on the time line over the weekend. A few were directed at me. I can’t be sure that my own didn’t explode on innocents. We are all culpable in ways big and small.

I am doing what I can to dust myself off and carry on because work must be done. We’ve not yet finished building a better future. We’ve barely even built the outlines for a tolerably decent present. I pray it’s too soon for us to find out how hot our hate burns.

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Finance Politics Preparedness

Day 800 and Small Potatoes

It’s nice when a round number crops up in my daily journey of writing every single day. It’s even better when it’s colliding with the wider narratives of humans. If you aren’t paying attention to the news, Silicon Valley bank had a run on Thursday and was taken over by FDIC on Friday. Now the powers that be decide our fates. On day 800 we wait to see if anything has changed about capitalism.

I’m small potatoes so I’m scrambling for survival as much as anyone. But I’ve got a reasonably good head on me and I’ve seen this movie before. Literally. I watched Margin Call a dozen times this year. My family also went bankrupt in the 2001 crash and I was working in startup land during the 2008 crash. So this isn’t exactly my first ride on the roller coaster. I still get sick to my stomach though.

I think we are all about to have a significant conversation in America about trust and who is looking out for whom. I have my theories on how it plays out and over what time horizon. Very few of those scenarios and involves actually letting the american economy implode. But some heads will need to roll it’s just going to depend on the fates.

I really don’t feel like writing through some of this as it’s both personally traumatic because I’m a human being but also because I don’t know where this lands any more than you do. A lot depends on who blinks and who we want to scapegoat and how much we want to tolerate the unpleasant realities of who matters most. Not to be dramatic but every empire rests on a pile of skulls. It’s the degree to which this is literally true that changes over the years.