I’m attending Ethereum Denver through the weekend. If you aren’t familiar it’s a fairly substantial crypto conference with wide appeal and good credibility across the entire ecosystem. I don’t have any special hookups nor do I have a careful plan of attack. It’s my first time attending a large industry event as an investor.
Truthfully I’m incredibly nervous. I’ve never been on this side of the table before. I’ve always attended events as a founder. Which is an entirely different mix of status and social positioning from a venture capitalist. Founders are the cool ones. The top of the social hierarchy. It’s the hardest job in the business and in exchange we revere them as a kind of messianic class. We all place our belief in the people who start building from nothing. Even if you haven’t yet had a big success it’s the act of beginning that has the potency. Anyone who has the guts and steel to try to make something new is part of that rarified class.
So while I ostensibly have more power than I’ve ever had in my entire career, I also feel a slight sense of social anxiety. This is the first time I’ve not been in the anointed. So in a very real sense I’m walking in without any of the power that I’ve had before. And I’m a little scared.
Will people think I’m cool? Will I get invited to go to the right parties? Will the right people want to talk to me? Will I look good enough? Will I be able to hold my own such that I can capture the attention of other peers?
I’m used to needing to network hard to find the money. I’d roll into events with my team squashed into one room and we’d plan out every single minute to maximize our budget. Now I’m the one teams will be searching for pitch.
It’s this strange blend of gaining new status but missing the old place and position in a culture that has me a little nervous. So if you find me at the conference know that if you are scared to strike up a conversation you are not alone. We are all looking to find each other and connect.
I’m one of those “life optimization” types. I spend a lot of time on various wellness applications. My health stack is deep. Over the years I have attempted to integrate more productivity applications into my life. But beyond a basic “to do” list I’ve found myself failing to maintain anything more complicated than ToDoist task list.
I think my failure is related to the challenge inherent in optimizing deep work. A lot of what passes for work in regular jobs isn’t a big part of my work. I don’t have a ton of alignment meetings because I am accountable to my LPs and my founders but not horizontal stakeholders. I don’t have tons of reporting as again the buy-in is pretty contained.
Ultimately I am only responsible for outcomes. And my outcomes will take years to materialize. I’ve got to get conviction on a decision largely on my own. I am responsible for my own success. And yes it’s a little bit scary to realize I’m in control.
This means I can’t fixate on signifiers of work. Which is largely what productivity apps track. The representation of the work is usually what gets tracked and measured. Arguably I can have my own OKRs (objectives and key results) but I’ve not encountered any personal productivity apps that work well for that framework. It basically boils down to the harsh truth that most of my work is deep work and it’s harder to measure. Deep work is the stuff of slow integration and accumulating knowledge up until it turns into catalysts, breakthroughs and ambush predation.
A gamer friend called me a glass cannon. I’d never heard the term before. It basically boils down to a character that has impressive offensive work but little stamina or defensive work. When they hit crit they go off. Boom! When facing a glass cannon you’d better hope you kill them before they rock your world as if they cycle back for another hit you are fucked. Glass cannons are hard to kill despite the appearance of weakness.
I spend my time preparing for action. Integrating knowledge. Widening my horizons. Intaking potential opportunities. None of which is easy to measure and moderate in traditional work culture. But when I go off you know I’ve made a move. It’s clear. Decisive. But the intervening time between? I’m preparing to go critical. You don’t know when or how but then it’s all in. A glass cannon may be the ideal archetype for venture investors.
I welcome pitches through my social media channels. I’ve even gone so far as to put together an FAQ for how to pitch me. I hope I do a good job of welcoming founders at even the earliest stages into conversation. But just because I am happy to shoot the shit with you, doesn’t mean I’m capable of organizing your thoughts for you.
Want me to write a check? When you are getting started with me keep it simple. Ground me in the basics so you can take me into the details. Go from whole to parts.
Now I’m not asking you to dumb it down. I’m asking you to do the work to really clarify what you want to make. Maybe it doesn’t sound as impressive in a few sentences, but trust me you must anchor everything in the basics. If you cannot articulate the core product you need to build how in a few sentences, how do you think you will convince me to support your biggest craziest vision?
Now what I am asking you to do is actually quite hard. If you aren’t sure what I mean when I ask for a basic product description spend some time on the excellent Reddit sub “Explain Like I’m 5.” The premise is simple. If you have a complex technical topic that requires expertise you need a way to get it across to a layperson.
You will hire a lot of lay people in your career as a founder. I am just the first one. Educating me on what you are doing is hopefully the start of thousands of explanations you will give on what your company does. Because we both want you to build a big company right?
So while you are welcome to send me your standard 15 page deck, or in depth Notion documentation, or your favorite Substack blog posts, you know I have to explain it to the co-investors, new hires and LPs in a sentence right?
What I don’t want is to dig through dozens of documents and feel even less sure by the end of my diligence of what you are building than when I started. I want to hear a synopsis that excites me to dig in and then go on a journey with you where I learn just how much you’ve thought about it. But if you can’t keep it simple you probably aren’t ready to be fundraising.
Being sick gave me an investing process. I have ankylosing spondylitis which is an inflammatory condition of the spine. It’s well controlled but still affects my day to day routines. It means I spend a lot of time in bed on my phone online. And this is how I generate alpha.
I spend my entire day on Twitter, in Discord, in DAO governance chats, in news RSS feeds and on Reddit. I’m extremely online. Terminally so. Like a LOT. I’m talking twelve hours a day. Which has turned out to be great for deal flow and diligence.
Being extremely online gives you some significant tactical advantages as an investor.
Persistent read of zeitgeist
Always online intaking discourse that will move market sentiments
Omnipresent availability to founders and ready to interact
Being online and intaking discourse gives me additional time and analysis with emerging trends, personalities and opportunities. By the time something has gained traction I’ve already made a move. I can move fast and confidently ahead of others because I’ve just had more time with the materials.
In somewhat bleaker terms I already live in the metaverse. Having a disability gave me early access to new ways of living online by forcing me to live a lot of my life virtually. If I wanted to socialize I had to do it in bed. I had experience with this before the pandemic. And I’m already been living where the rest of the world will be migrating now. You are gentrifying my neighborhood.
I am coming slowly into 2022 in its fullness. Perhaps I am living in seasonal time this year. I am feeling the wholeness of what the moment brings and January is about becoming. So it wasn’t surprisingly that clarity of purpose has been sharpening for me. I am ready to commit to self acceptance as the theme of my year.
I felt somehow today that the only thing that really mattered for my success in the world was radically altering any perception I had of myself as negative. That I was here to love even the parts of myself that cause me shame and fear. The only thing that will take me where I want to go is loving myself. That self love was actually the key to all troubles personal and professional.
“You know, loving awareness—even if you haven’t heard the phrase before, you know what it is. Those moments of spacious, calm, thorough, tranquil connection with whatever portion of existence you’re currently exposed to, where nothing is being challenged or conceptualized, but rather is just allowed to appear, in radiant suchness, without resistance or fear.”
I’ve discussed the emotional work I do on the blog at length. The Family Systems Therapy and it’s exploration of the inner child. The shadow work and integrating of the whole of oneself. But I do often reject the crucial step of feeling like I am fundamentally alright. I am ok. I am enough.
I’ve committed to “a bit” where I lavish myself with self improvement and luxuriate in needing to make every measurement better. I’m obsessed with finding metrics to improve. And so I give myself little problems to fix. Maybe I’ll eat poorly so I can feel bad about my body composition. When instead I could just eat what I like and accept that maybe I’ve made other priorities than my figure. I don’t need to agonize over trivial shit.
But equally I don’t need to agonize over big shit. So I’m not a perfectly credentialed super star. I’m more of an eccentric. I don’t live like other people so I see other things. My existence is the selling point. If what I bring to the table is what you want then I am the right partner for you. If am I not then well tautologically I’m not for you. Partnerships are accepting what everyone brings.
So through the end of this year I am going to bring self love and acceptance to my writing here. In letting myself be seen I can more fully bring myself to my partners. Being a startup investor that means I must be present for my founders, their teams, and my own LPs and stakeholders. I’m bringing the full depth of my being because that’s also going to bring the best returns. Because being ok. Accepting the moment and it’s inhabitants? That brings us the creative potential to solve whatever is in front of us without judgement.
I spent a part of my day gossiping with a friend of mine who is from the same cofounder cohort as I am. We’ve got a lot of common interests beyond having both been founders at the same time and I won’t list them as I don’t want to give them any hassle. But the two of us have seen a lot of the same things. We are now experienced.
It’s funny what you notice when you are experienced. We were noticing little aspects of how founders we taught or mentored or invested in tended to repeat. How there are certain repetitive patterns you notice in first time founders or folks who are new to Silicon Valley culture. You notice idiosyncratic elements that all n00bs have.
Of course the where it becomes hard is how much time do you put into coaching them. Can you help them level up fast enough to avoid all the mistakes you made? Can they outrun all their faults and weaknesses by adding new strengths where it matters? It’s honest the best work in the world. You find yourself constantly optimistic that big things are possible. That the best version of someone is inevitable with work and love.
Of course founders with battle scars know it best. We know where the sharp turns on the road are. Because we wiped out there. When we yell out to you to watch out it’s because we know the road better than you.
I’d also bet that this is why venture capitalists will stay with founders who are floundering and fucking up and being failures. You’ve seen their bright spark. You know their brightest self and it’s aspirations. And sometimes it’s really hard to accept when someone just isn’t going to make it. Because belief is deeper than facts sometimes.
There is a Reddit sub that is imploding at the moment called Antiwork. I didn’t really follow it before the extremely online moment where one of their mods demonstrated that internet people don’t generally have media training. But one of the amusing bits of antiwork culture got into my feed because someone had an awkwardly worded tweet about young people demanding at least two days off of work in a week.
Before I became a member of the capital class I wasn’t really much of a weekend person. Or even a time off person. I was in a constant battle to get over the line of survivable earnings in America.
But then the magic of Silicon Valley shined on me a few times and I’m suddenly no longer desperate about medical bills or having enough savings for an emergency. This has had the dramatic effect of completely reordering my priorities. Now I take restorative rest time seriously. Knowledge work and good judgement rely pretty heavily on be clear headed. There is no premium afforded for being exhausted. If anything it will lose you money.
So the antiwork folks might have a point. If so much of your life is spent in survival you never have a chance to really be human. And being human is oddly more lucrative. I stand a better chance of doing even better because I can orient my life around bigger outcomes. That attracts more people and more money and improved my chances. And yeah success compounds if you are lucky. If you can get out from under survival. Which is I suppose the hard part.
Maybe three years ago William Gibson was promoting his new book. It was the last event I attended in a pre-pandemic world so it stands out to me. He gave an interview where he mentioned reading a novel by Hari Kunzru called “Red Pilled” and that he found the plot as a plausible near future.
I immediately bought a copy as I’m heavily influenced by the prescient near future work of @GreatDismal. The book was about a member of the blue check media class slowly going stark raving mad because of an elaborate right wing alt-reich troll farming operation. It was uncomfortably clear on the kind of elaborate cultural war tactics that goes into pilling normies. Dank memes and slowly you are accepting the aesthetics and touchstones of former Reich minutiae or Nordic runes or pick your mythical volk white mythology. Memes are dangerous gateway ideology kids.
I didn’t really think anything of it at the time. Then I lived through the pandemic becoming an elaborate death cult ritual with totemic significance for both warring sides. I realized we are in the middle of a massive meme war for the soul of internet culture and most of us don’t know we are victims yet.
Walk down one wrong hobby hole on Reddit and suddenly you have become friends with folks with more than passing fascinations with authoritarian culture. Honestly it’s freaky as shit and I’m absolutely socially friendly with people who don’t think I’m a fully autonomous sovereign individual. And yes I mean both socialist Soviet apologist Tankies and TradCath beach fascists.
The latest example of mass hyper object cultural murmurations might be the Bored Ape Yacht Club. And not in the way you think! It was brought to my attention by Venkatesh Rao and he clicked together some signs I’d registered but not processed. It’s entirely possible someone pulled a QAnon semiotic culture jacking with everyone’s favorite NFT project and made it so we all consumed a bunch of Nazis culture.
If even a fraction of the wild associative leaps are premeditated it would be a kind of aesthetic scandal on par with the country electing a reality show host. A couple nRX message-board fascists cosplaying as Zombie Nazis grift 4 billion dollars in market place from venture capitalists and gullible celebrities. What a collective failure to repudiate literal Nazis! Lol. Maybe this means our unconscious might think some of this is right? Oh god maybe we did read a human biodiversity essay that made a convincing point. We seem to be a lot closer to black pilled. Fuck. Is this psychological warfare?
Honestly I hate this fantasy so much I hope it ends up being the largest milkshake ducking in history. Except at the end a whole bunch of us end up simping for the technical value of a bunch of Hitler memes. Fuck I’d die if this is how we all got pilled on antique fascist aesthetics. I’d love it even more if Peter Thiel were involved so the left wing conspiracy types could build their own QAnon metaverse. Already we’ve been warned about meme magic and the spiritual traditionalism that is animating a global new right. And I’ve got to be honest some of the threads going around have some elaborate research and narrative work. It’s propaganda level and designed to be compelling and confusing.
BAYC is of the most intricate hidden trolling campaigns in history created by very intelligent 4chan-related trolls who have hidden lots of nazi and alt-right innuendoes across the collection I’ve gathered enough proof to confirm it.
I honestly have no idea who is playing who in this saga. I’m think @vgr is probably right that even the terminally online struggle to make sensible or legible this level of signaling. So we brush it off. But it’s going to be an inception vector. So be careful when you react to an event. You might be primed to respond to their propaganda and not even know it.
So if you want to pitch me just hop on over to a Telegram chat or my Twitter DMs. Let’s talk and learn and share and then I can really see your passion and vision and we can both avoid canned performative shit.
Well since then my Twitter DMs have been filled with amazing chats with founders of companies as diverse as consumer products, marketplaces and web3 games. The stuff people are cooking up in crypto is wild. Thought not enough SaaS tool pitches though so clearly I’ve got to get more mindshare there. Note to self to impress Jason Lemkin or something.
I’ve taken a dozen pitches now through direct messages and chats. It’s worked amazingly well. Maybe I owe a drink to Sam Lessin as he came out strongly against Calendly right after I wrote this post.
So pitch me however you like to communicate. Plus, don’t we all die inside a little every time someone sends a Calendly link?
So I’ve got to say I hope I became known as the slide into her DMs VC as this has been a lot more fun than trying to play calendar sync with dozens of people. That game sucks.
Daily overstimulation is starting to rub the pressure sores of America’s downer induced depression into a full blown mental health crisis. Like, even more than usual. War with Russia in the imagination, inflation and market volatility coaxing a recession, culture war skirmishes over every basic fact in the pandemic, along with generalized anxiety are fucking us up focus wise. And every propaganda outlet and publicist on the planet is having a field day.
I’m listing to The Prodigy’s Breath and mumbling lyrics like pyschosomatic insane. So I guess, come play my game?
I try not to listen too much music as it overstimulates my nervous system to be honest so its kind of rare for me to have Spotify playing. I’ve got a finely tuned propaganda radar that benefits from sensing subtle shifts in tone and extremely online discourse. I can’t do that if I’m too worked up from the rough stimulus that comes from pop music. I mostly use it to run my portfolio and investing but sometimes I think I should really be used in the service of some autocrat or multi-national. I’m the doubt factory
I guess it is nice I can make a buck during the end of the empire. I’m one of those post structuralism, post-capitalism babies. A regular Bane “born to the darkness” of hyper objects like markets and climate change. So I guess I’d better be molded to being the kind of villain that survives a world of agitprop and meme warfare. Thanks Adbusters!
Frankly I’m having a fucking blast. Sure I’m scared I don’t have my homestead property all shored up for civilization hiccups, but I’m of the mind that the crumbles is going to take a while so might as well enjoy the gains that come from a massive upheaval. I guess its true venture capitalists are ghouls. I mean at least we aren’t private equity carrion birds but it is wild that the system rewards a class of people that invest in creative destruction.
But even as I want to paint myself as bad, I do stereotypically think what venture capital does is often good. We can’t predict second order effects. Chaos theory doesn’t let us see all the future paths. But stochastic as shit power laws are just math so we’ve got a shot at accidentally making things better. So while the agitprop tries to sway your opinions might I recommend you just Breath? That is my professional advice.
