Categories
Startups

Day 468 and Small Moves

One of my favorite movies as a kid was Carl Sagan’s Contact. It’s not a great movie but it’s heart is in the right place. It’s a beautiful story about human curiosity and the long timeline of history. In one of the closing sequences the protagonist is told by alien intelligence as embodied by a representation of her dead father that all next steps are “small moves Ellie.”

I never feel like I’m moving fast enough. Every day presses against me. I long to slog through them with speed and alacrity. It’s almost embarrassing how inadequate I find my progress. But then I remember that I move fast. I live ahead of the mainstream. I get to sit in the future that William Gibson said was not evenly distributed. Even if I don’t think I’m particularly good it’s hard to deny just how much of my life is lived in a tiny sliver of humanity.

Someone recently asked me how I moved so fast when I’m dealing with a chronic illness. I found it to be such a shocking question. I feel like I’m glacial compared to the reach of my desires and imagination. But then I’m reminded that even in shorter hours I’m forced to hone my crafts. I can’t afford to waste energy or focus so I simply do not. I imagine this focusing out of need is similar to what parents of young children operate in. The subtle art of not giving a fuck.

And so what if I am slow on a day to day basis. Rome wasn’t built in a day. I’m not a market trader. I invest in ten year cycles. Everything in venture is actually small moves. But as time adds up so do the aggregate of the moves. Compounding interest is up there with gravity as a force. So even when I yearn for more and for it to arrive faster I have to trust the numbers.

Categories
Emotional Work

Day 438 and That’s Enough

I attended a schooling system developed by an Austrian man called Rudolf Steiner. It’s commonly known as Waldorf schools. One of its hallmarks is a lack of comparative grades.

Steiner believed that grades forced teachers and students into a curriculum that taught to the middle of the class. The tyranny of the median student meant slower students felt stupid and frustrated and smarter students felt bored and disengaged. Only the average child did well in a graded system. And no one is ever truly average. A graded system fails us all.

Waldorf schools teach a pedagogy that is holistic and geared to meeting each individual child at their unique level. It uses a variety of techniques like having children make their own textbooks (called main lesson books) so they are never conforming to some idealized medium standard. At it’s highest ideal it means being compared only to your past performance. You don’t compare yourself to other students. There is no ideal grade at which a student will think “I am the best” as that is fruitless. How will the best student ever bother to improve if they always get a perfect score? Grades hamper the cultivation of genius.

This sounds idyllic right? Always improving yourself without external markers that say you are good or bad or even average. That’s the dream. A perfect schooling system. And if I am being honest it absolutely was what provided me with the curiosity and desire to always be learning. It sustains my career now.

But every shining light casts a shadow. A system without grades. A system without comparisons or averages also means you never ever get to win. I never got a gold star as child. I never got an A. I never got a trophy. I missed out on millennial laziness cultural tropes. I would have killed for a participation trophy as a kid.

Because nothing was ever good enough. Because I always knew I could do more. I could always improve. There was no resting on your laurels. I never got a chance to say I was the best in my class. I never got to win. Because I internalized there was no winning. There was only ever improving. I was always improving. I felt like Sisyphus. Except the bolder never rolled down the hill. The hill just kept on going. The mountain had no summit. It was only improving. I never felt like I could rest. I never felt like something was good enough. Because tautologically it couldn’t be.

The consequence of this system for me as an adult is that I never feel like I’ve done well such that I can ever rest. Even if I’m objectively the best compared to others, I remember the ethos of school. The school that said next time you can do better. Next time you can push harder. Next time you can improve even more. If you’ve ever seen the movie Gattaca it’s the scene where the hero wins because he never ever saves anything for the swim back.

I’ve yet to balance the shadow cast by the light of Waldorf school. I desperately want to feel like I’ve won. Not because I need to feel better than anyone else. But because I struggle to stop. I yearn for rest. To have a finish line. To have some mile marker or trophy or award that says I’ve done enough. One day I’d like to give myself that. Maybe I should find a trophy or ribbon store and buy myself something that says “That’s Enough.”

Categories
Emotional Work Startups

Day 409 and Glass Cannon

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.

Categories
Internet Culture Startups

Day 404 and My Process

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.

Categories
Chronic Disease Uncategorized

Day 372 and Pace Yourself

I was in an incredible groove yesterday. I’ve been letting go of the awful December I experienced and enjoying the new January energy. If you look at yesterday’s post I was absolutely in the zone. So I pushed myself thinking I can handle full capacity day. Mistakes were made in my enthusiasm. And well I’m probably in need of a rest. I over did it.

I often struggle with pacing and moderation. It’s important for me to remember that I’ve got a history as a workaholic. But I don’t want to feel as if I can’t push myself either. It’s the middle path I must walk. But it is hard to stay on it. I feel like every day I am sliding off the middle path right into the ditch. I’m getting better at getting myself back.

I used to be happy mailing elaborate detours. I’d take every exit on this metaphorical path in the past. But tonight I’m going to remind myself I’ve got a destination. And that is being responsible for keeping myself happy and healthy. So I’m going to get in bed and watch some TV and shitpost on Twitter

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Background

Day 363 and Best Of 21

One of the unexpected benefits of writing every single day has been the accumulation of reference material. I can send folks a synopsis rather than retyping a topic that I get asked about a lot. So if you want to know how I get healthy, or how I invest, or even how I think about aesthetics this page will serve as a reference for year 1.

Health & Wellness

Biohacking 101 Guide

Supplements for Beginners

Self Care & Pacing and Recovery Protocols

How To Communicate with Me

Why I Prefer Asynchronous Communication

Why I Dislike Phone Calls (Or DM Me First)

Getting To Know Me for Founders Seeking Investment

Investment Thesis Thoughts

Empathy Investing

Chaotic Labor Markets

Chaotic Families

Request for Founders

Psychological Safety

Mental Flexibility

Bias Towards Fuckaround

What Don’t I Know?

Why I Don’t Like to Invest In Retail Anymore

Aesthetics

Fashion Week Back in The Aughts

The Thursday Styles Problem

Swag (Or My Facebook Hoodie)

A General Theory of Shitposting

Cultural Hegemony and Internet Citizenship

A Short Guide to Becoming an Edgelord

Advice for Startups

Above All Else Fun

Inertia

Rooting For You

Stress, Luck & Startup Families

The Emotion of A Big Exit (or Stack Overflow Sold)

Show Me Anything

Just Make Stuff

Optimizing For The Right Outcome

How To Work With A Startup

Emotional Growth

3 People Inside You

Punishment

Forgiveness and Failure

Easy for You (Not For Everyone)

Superpowers

My Addiction to Work

Categories
Medical

Day 355 and Not That Bad

I made one of the rookie mistakes in coping with illness today. Yesterday I came back positive for Covid. It was pretty mild. So I didn’t cancel any of my appointments. I went to therapy. I still had an on and off work day with a few obligations. And now I feel like shit

Basically I ignored my own advice. I wrote a post about how to effectively beat back an illness in a post I called “How to be sick.” And just a few days later I forgot everything I said. I feel very on my own bullshit.

My experience of Omicron has been quite mild. It feels much more like an inflammatory condition than a respiratory one for me. My whole body aches. I ran a slight fever. I’m exhausted. And I have awful brain fog. Like my normal speed of thinking has slowed ten fold. I can still recall the topics or even general contours of what I want to say. But then I can’t quite get the specifics to form in my mind. It really is like living through a fog.

So I need to wrap this post up and go to bed. I am sick. It’s mild but it doesn’t mean it’s not there. So I need to treat myself gentle and make sure I help myself get well. If you get sick don’t push yourself. It will only extend the experience.

Categories
Emotional Work

Day 347 and Self Acceptance

Because a huge chunk of this writing exercise has been tagged under “emotional work” I’ve had the good fortune of chronicling much of my emotional growth this year. A huge theme? Learning to love myself. I know, it’s pretty core stuff. You are probably working on the same thing as me. Just because it’s fundamental doesn’t mean it’s easy!

My favorite coping mechanism is working harder. Didn’t get what I wanted? It’s my fault. Maybe if I’d put in make work I would have! I’ve got a whole circle of abuse I pour on myself. It’s always my responsibility if something didn’t work out. Not happy? Time for self improvement. It’s rarely occurs to me that I should simply accept myself and that sometimes things simply don’t go my way. I don’t seek out self improvement for the joy of it. I do it to punish myself.

I’m terrified of letting go of my coping mechanisms. If I was good enough I would have felt loved as a child. This is a horrible inner child logic that I’m applying to myself. As if an infant deserves love because of its efforts. We love our children just for existing. And yet I struggle to express love for my own inner child.

If I stop using hard work as a coping mechanism I am afraid I’ll never be accepted again. If I let it loop even further I am afraid I will die. Because I fear I only overcame my health issues because I throw so much effort into recovery. I am afraid it is only through effort, punishment and improvement that I deserve to be in this world. Any wonder I find Calvinism appealing as a faith?

I tell myself these are rational coping mechanisms. The world does reward me for hard work and continual efforts towards improvement. I pay my bills through hard work. And sure if I don’t pursue basic healthy habits and fitness then yes I probably won’t feel as well. But these arguments are just an excuse to keep myself from accepting that I’m worthy as a human independent of my work or my health. And because I have a hard time hearing this for myself I want you to know you are worthy just for being you too. Our humanity is enough.

Categories
Emotional Work

Day 345 and Trust

I’ve not always been accepting of my own weaknesses. Instead of focusing on how well I can hone my super powers, I’ve occasionally fixated on where I lack innate talent. I’m not particularly adapt at operations or logistics but I feel bad about it. I am however genuinely top tier when it comes to narrative & attention. Somehow I don’t feel equally good about this.

I’ve tried to work in teams where my talents & weaknesses are balanced out by others. I like teamwork now in a way I didn’t fully appreciate when I was younger. I’ve learned to trust my own value. And I am able to emotionally trust the people around me.

The psychological safety that comes from trusting yourself and others is a lifelong process. Even a few years ago I’d struggle to not compulsively overwork to overcome my weaknesses. When I should have been honing my unique talents.

I’ve got an opportunity over the next few days to really trust one of my teams. We’ve got a deliverable that isn’t in my area but I’d crucial to success. I could spend my extra energy worrying over it and making an attempt to contribute just so I felt useful. Or I can emotionally let go and appreciate the trust I have in others.

Categories
Emotional Work

Day 338 and Effort

The real world rewards talent. It largely doesn’t give a fuck about effort. Sure, we like it when someone with talent works hard at honing their gifts. But if you just work hard it is largely ignored. The end result still matters most. Talent more easily gets the desired outcome.

This is a sort of hard truth that isn’t particularly hard to grasp. Every bit of evidence you have from a young age indicates that we reward outcome. Even if you are in a school system without grades, like I was, we still know what a quality outcome looks like. But we spend all this time and effort lying to kids with this separate system of effort that suggests that working hard and putting in a lot of effort are the thing “good” kids do.

I’m not wild about praising effort and hard work on its own. Sure it matters, hard work honing your skills, even when you suck, has its own value. But not when it comes to what the world expects of us. We inculcate habits and emotional expectations that are basically cargo cults. No wonder kids, after being praised and rewarded for effort for a decade or two, are confused when they get their first job. I’d be fucking pissed if I were that kid. I’d slowly shaped my behavior around one set of expectations only to find it had no bearing on reality.

Why do we spend so much time cultivating the myth that effort matters as much as talent? Why do we praise effort so consistently among our youth when we know that at a job being told “well you work hard but…” is probably a prelude to being let go. You have to work hard and achieve the desire outcome. It’s enough to drive people nuts. It is literally crazy making to contradict reality with all these lessons on effort. We are gaslighting our youth.