Month: February 2022

Categories
Finance Internet Culture Startups

Day 414 and Empire’s End

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.

Categories
Internet Culture Startups

Day 413 and Don’t Believe the Hypebeast

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.

Categories
Startups

Day 412 and Status Anxiety

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.

Categories
Background

Day 411 and Good Day

I’m flat on my back in bed waiting for my Advil to kick in. I’m the kind of satisfied tired that only comes from a good day. But I’m also in pain as I did so much today that eking out this blog post is a bit intimidating. As with all good things they become bad when you over do it.

I am that stage of tired where I can’t even work myself up to go wash my face. I’m in bed texting and scrolling Twitter and hoping I’ll get a surge of energy to do what needs to be done. Alas it’s been an hour so I think I’ll need to go with sheer force of will.

I packed a lot in today as I’m headed for my first in person event since the pandemic started. I’ll be at Ethereum Denver through Saturday. And in March I’ll be in Europe for the whole month which is another whole thing. Having travel plans means more errands and more preparations than I’m used to incorporating. Which is just such a foreign feeling. Remember when we all traveled a ton?

Categories
Aesthetics Emotional Work

Day 410 and My Own Valentine

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!

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
Medical

Day 408 and Getting Ahead

My first piece of international travel since the pandemic began is coming up. I’ve not been on an airplane in over two years which is wild. But I needed to get a booster shot for my travel papers.

I was a bit nervous about how I’d react. I didn’t have the easiest time getting vaccinated. But I had a mild case of Omicon in December which made me slightly more optimistic about it.

I got caught in a snowstorm getting the booster yesterday. Which is so far the only inconvenience. I slept fine last night. I didn’t appear to spike a fever. I had no aches or pains other than the ones I live with normally. I’m so far enjoying having little to no reaction.

I did however take very good care of myself. I felt a migraine coming on mid-morning and I rushed in with all the good drugs. I wasn’t going to let myself suffer at all. And I am suspecting that keeping any and all stresses away has in fact been excellent for my body. Just another reminder that drugs are in fact good. Loving yourself can often mean mean treating yourself kindly. Removing the option for suffering and maybe all recovery can be this easy.

Categories
Preparedness

Day 407 and Snow Blind

We’d scheduled booster shots for this afternoon. Even though we’ve both recently had Covid, I’ve got travel coming up so I needed to get a booster to get into Europe. I probably have never had better immunity to the disease than I do right now so I’m feeling optimistic about being around people again.

But I didn’t realize it was going to snow today. The forecast said it would lightly snow for an hour or two. So I thought it’s fine to schedule vaccines now. I wanted them right before the weekend so I had maximum time to rest and recover.

But clearly the forecasts were we wrong as we headed into a significant storm to get our shots. An hour later as we wrapped it up we were in driving snow with very little visibility. The roads were accumulating snowfall fast. The normally fifteen minute drive hour stretched into triple time.

Thankfully we made it home safely. And we’ve been shot up for the sake of paperwork. I only feel marginally worse for wear.

Categories
Startups

Day 406 and Like I’m 5

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.

Categories
Emotional Work

Day 405 and Okayness

I wasn’t in my “okayness” this morning. My focus on self love hit a snag on hormones. I woke up with a migraine and menstruation and I wanted to treat myself as an attack surface. So I asked my Twitter feed to tell me how they got to okayness. And it was beautiful.

I am often struck by how if you share your vulnerability with people they will open up with their own. The joy I get from connecting with you in the fullness of being ourselves gives my entire life meaning.

What seems even wilder to me is that this kind of connection happens on Twitter. It’s crazy that out in some virtual world, the metaverse if you will, the most human needs are met. We can see each other on a phone application. It’s enough to take your breathe away.

I’d encourage you to browse the thread as it’s filled with insight. People take long Lindy walks and do their nails. They lower their standards and raise their spirits. They integrate shadow elements into their identity. They take little risks and embarrass themselves. They imagine the tweet they would send at the end of the day with their accomplishments. But most of all people make things. That even when being a human being seems like an impossible challenge our capacity to build gives solace.