If you are a media junkie today was chaotic as fuck. Last Friday I was talking to a fellow preparedness enthusiast Josh Centers. We’d been discussing the situation in the Ukraine and how it might affect daily life in America. He’d been considering launching a Substack to help folks approach the topic of preparedness during our increasingly unstable times. I am obviously a keen observer of this space as I do firmly believe the word is getting weirder that I named my venture fund Chaotic.capital.
I’m glad he took the leap and launched Unprepared.life today as his analysis has set my mind at ease even as it looks ever clearer a conflict involving Russia is inevitable. Josh is a crisp clear writer that has a knack for communicating vital information in a crisis without alarmism. I very much recommend you subscribe. I believe in him so much I’ve personally invested.
Much as it pains me I do believe the topic of preparedness is becoming more relevant by the day. The Wall Street Journal recently analyzed America’s power grid and its increasing unreliability. And that’s just one example of how life is getting a little bit harder and a little bit more expensive and a whole lot more unpredictable. But just because there is chaos in the world doesn’t mean your responsibilities are any less. Your family still needs to eat even if supply chains are unreliable. Your work still expects you to deliver even if there is a power outage. The bank doesn’t care if inflation is making your mortgage more expensive. Life goes on even during crisis.
I don’t think of myself as disabled or requiring special accommodations, though I have a well controlled medical condition that swells my spinal cord called ankylosing spondylitis. But for the first time since my diagnosis I really felt like I was handicapped. And I am feeling so much sadness over the idea that I might genuinely be disabled.
I’m attending ETHDenver and it’s wildly over capacity. No consideration has been given to any kind of basic accessibility. I didn’t think it would effect me though till I got here. I can walk without a mobility aid and if you met me you’d never know I have an issue. But I can’t stand in line on cold concrete for two hours. It turns out I would need a wheelchair for that kind of activity. And even if I had a wheelchair the first two days were in the cold and snow so I couldn’t have wheeled over or around the slush and water.
So I have only attended private parties and small events and group outings. This is great for me as I’m a well networked established member of the startup ecosystem. I’ve got a popular Twitter handle and can easily reach out to people. But I’m noticing just how much a bit of inaccessibility will gatekeep the crypto and web3 community. If you don’t have my heaps of privilege there is no way you could navigate this conference.
And we really need web3 to be welcoming and accessible. To build a better future with infrastructure and economies we all collectively own and benefit from we need an order of magnitude more people participating. But if no one can get in and experience things first hand than web3 will just be a repeat of the oligarchy of web2. It’s honestly my worst fear for crypto. We will accidentally exclude the people who will benefit the most from our innovations.
Being at a crypto convention in 2022 is something else. It’s full jubilee at the end of the world shit. You are surrounded by millennials and gen-zers who know in their gut that their future has been stolen from them. And instead of being pissed they decided to build. And they decided to gamble. And it’s not clear which one is which sometimes.
You’d be forgiven being a nihilist right now. Capitalism looks like an excuse for the oligarchs to consolidate state and private power to enrich themselves. Everyone is soaking in student debt and working shitty interchangeable jobs for corporations owned by private equity. No one can afford a house. No one is stable enough for a marriage and children. Our fucking parents won’t retire and won’t listen to reason when we say their neighborhood needs more housing density.
But if you are in crypto the future looks pretty rosy. You are discussing real estate for your second home and the tax advantages of different jurisdictions. Swapping stories about your friend who accidentally didn’t set up estate planning and his company had a big exit and now he’s got to pay full rate to some expensive Democratic run city and state. If you are at the nice cocktail parties you are building the future and the venture capital is flowing and it’s possible that this is the next big wave of innovation. It’s time to fuck around and find out.
But not everyone in crypto is part of the smart money. Not everyone has institutional backing and the professionalization of long time startup operators coming to build real value. Right right below that success is a teeming horde of brutalized and completely marginalized people who are praying they hit it big on some new coin or hot new NFT project. They saw Bitcoin and then Ethereum go to the moon. So now they are praying to the full moon and hoping they ape into the next big thing.
But what’s scarier is that the prevailing attitude is who cares if it’s risky because no one believes they are going to have a future anyway so you might as well gamble. They might get lucky and build the next Google if they join the right DAO and buidl. Yes I typed buidl. I’m a degen too. I’m a doomer that isn’t convinced the empire is going to hold for much longer. And if I’m going to watch it all crash down I want to be a part of building something better for all of us. Maybe we get lucky and innovative faster than the apocalypse. To be fair, humanity always has in the past.
My early twenties were heavily influenced by streetwear and sneakerhead culture. I lived in the Lower East side and hung out with all the kids who would go on to dominate what is now a multi-billion dollar industry.
It feels weird listing out my bonafides as it’s pretty name drop-y but at the time it was like yeah my friends at Alife or High Snobiety or even god forbid Supreme meant basically nothing. I was in the absolute epicenter of hypebeast mania.
So I’ve got a gut sense of what a genuine upswell of obsession looks like. The kind of irrational social capital driven cool mania of the sneakerhead world has a specific vibe to it. Almost illegible to anyone outside. But to the in group? It’s powerful chaos magic binding geas shit.
That’s what EthDenver felt like today. A kind of disorganized overflow of true believers converging into a space about a quarter of the size required. It’s like if TechCrunch disrupt accidentally got overrun by the entire readership of HypeBeast. Honestly it kinda sucks.
You’ve got a number of accomplished teams and founders and investors all trying to figure out how to navigate long lines and complete chaos with no clear programming goal or event schedule. And then you’ve got thousands and thousands of NFT weirdos just shilling and excited and ebullient about stuff they freely admit they don’t technically understand. It’s going to be a wild ride for crypto.
I’m quite fond of Valentine’s Day. I like flowers and chocolates and cards. I like wearing bright pink. I like all the hyper feminine consumerism around the entire Hallmark holiday.
I’ve got my own rituals and routines for the day. I used to go to White Castle for their white tablecloth service with my friends. Yes that’s a real thing they do. It’s an absolute blast to get table service when the food is sliders. It’s a wholesome experience that somehow no one does ironically. They once let me take home all the balloons when I had the last reservation of the night.
But I am particularly enjoying Valentine’s Day this year because I’ve made a commitment to self love this year. I came into the day with a spirit of accepting myself in whatever condition I arrive in. It’s a glass half full approach in a time where it’s easy to look for downsides and depression.
I hope if you are considering committing to more love in your life that you start with yourself. That on Valentine’s Day you focus on giving yourself the love you’ve always wanted. Maybe it sounds as silly to you as having sliders with table service at White Castle. But I promise both experiences are far more than a critical ego will allow. Go ahead, open yourself up. To love and little hamburgers. Happy Valentine’s Day!
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.
It’s ok if someone hates me. It’s ok if someone thinks I’m bitchy, stupid, obnoxious and self serving. Hell I’m ok if people think I’m a lesser human being. Which judging by Twitter could be a multitude of reasons ranging from “I’m a woman” to “I’ve got bad taste in tv.”
I am alright with you not being alright with me. My existence is not threatened by your philosophy or personal preferences. My existence is only threatened if you literally threaten me. Call me evil if you like. I’m not offended. Until you take an action against me it’s alright that we disagree. Even if the disagreements are existential.
It’s quite possible this is wrong. I’m open to debate on what constitutes harm. In fact, my entire philosophy centers on that debate being fine. I can take it. I actually pay someone to cuss me out for being stupid and then I pay again to spend time in a group where we regularly tell each other how much the group members anger us. It’s called therapy.
So take that as context when I say I wasn’t particularly personally hurt by Brantly Milligan, aka Brantly.eth aka one of the ENS Foundation cofounders, suggesting women who use contraception are perverts. I’d probably be a lot more hurt if I was a gay trans woman who had an abortion though. But I figure that demo might be used to being called evil by Catholics at this point. Like maybe it’s more of an annoyance than existential threat if you are wealthy and privileged enough to be working in crypto. We aren’t really a population that is hurting
Brantley.eth “homosexual acts are evil. Transgenderism doesn’t exist. Abortion is murder. Contraception is a perversion. So is masturbation and porn.”
The Ethereum community is experiencing this speech with a lot of pain, hurt and anger. Brantley was voted out of his contract with True Names Limited the foundation that manages ENS Domains. But he remains one of the largest holders of tokens and will obviously have plenty of influence over the future of the platform. The debate has become one of cancel culture versus DAO governance working as intended. But the split on that is not clean and it’s not always clear where people will fall. An informal poll on my timeline is pretty evenly split.
Twitter poll asking if Brantley termination is governance working or cancel culture.
I’m tempted to assign him my tokens as a delegate to be honest. Though I won’t because I think he’s unprofessional. But I want to because I don’t love how any of it played out. Brantly doubled down on telling folks to fuck off compounding the feeling of being hurt. That’s unprofessional and not the kind of behavior I’d expect out of my management team. But I also don’t know that simply holding unpleasant or intolerant beliefs is enough. And it shouldn’t be in a decentralized system. I respect that the right voting and governance may have happened here but I’d argue we all want more control spread out over more people for exactly these scenarios.
I think Brantly basically Shrekli’d himself by doubling down on asshole antisocial shit and the DAO equivalent of the Feds coming for you happened. You can’t attract negative attention and be shocked when bad shit happens to you. But I don’t think being a retrograde weirdo is enough on it’s own to get you booted from an ecosystem.
The entire reason I’m walking you through this sensitive topic today is that I am committing my year to self love. And you might think how does self love and DAO governance overlap. But I really do feel empathy to everyone involved in ENS and the ethereum ecosystem right now. The pain of feeling like you are not seen and loved for who you are is primal shit. This is core human nature “do I belong” to my tribe stuff.
If you don’t love yourself than you are going to have a reactive stance to something that questions your morality and worth. And I’m guessing a lot of people are reactive judging by the uproar. But the thing about self love is that you just won’t be as hurt by assholes being assholes. Because you’ve taken care of yourself first. So whatever the right and just outcome of this ENS governance issue, I think it’s important we all check in on ourselves and why we reacted in the first place. Only then can we get on with the business of design the future and it’s technology.
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.
