Tag: Investing

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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.

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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
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
Finance Internet Culture

Day 394 and Antiwork

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.

Categories
Startups

Day 392 and Deal Flow

I wrote about my general philosophy about the futility of the typical hour long deck based venture pitch two days ago. I explained that I’d rather have a conversation with founders.

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.

Categories
Aesthetics Internet Culture

Day 391 and Breath

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.

Categories
Aesthetics Finance Startups

Day 390 and Pitches

So I think pitching is bullshit. My husband has a great analogy. He thinks an hour long pitch to an investor is like a white board coding interview. Have any of you ever done developer work that didn’t have access to StackOverflow and Google? Yeah didn’t think so. It’s a completely artificial environment. Real work is collaborative and input driven and not at all tied to your capacity to memorize and perform on the spot.

I think this is pretty revealing. We force intuitive input driven thinkers, our founders, into a situation where they have little to no feedback. They can’t get anything from us as investors for like twenty minutes. They lead an investor by the nose through a narrative but what if it’s a narrative the VC doesn’t care about. Then what you lose the deal? Fuck no.

You should anchor a conversation based on expressing interest and seeing together where the biggest vision might lay. I’ve legitimately talked to founders who can see their way into imploding corporate legal apparatus or building clean energy through on chain gaming. That is some science fiction level shit. But could they tell me that in a 12 page deck? Fuck no they would look insane. But I want to see you for who you are.

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.

You want an investor that sees you for you. I want a founder that is building with such a keen passion it’s all I can do to stop from wiring the money that day. Our incentives can align from first contact. So pitch me however you like to communicate. Plus, don’t we all die inside a little every time someone sends a Calendly link?

Categories
Finance

Day 389 and Bear Down for Midterms

I used to be something of a perma-bear. I was always somewhat convinced that bad shit was just around the corner. I guess you can see that in my persistent interest in doomer culture. But as the world continues to experience “the crumbles” I’ve softened my general stance on everything is awful.

Crypto is arguably responsible for much of my stance. For all the bitching about Web3’s lack of decentralization and heady “takes” on how this has all been done before, I actaully do this think is the next wave. Do I think we are due for a lot of crashing and failures and unrealized promise? Also yes.

So when the market decided to do a January bubble bursting I was surprised at how sanguine I was. I kind of didn’t believe it was going to turn into a full blown recession rout. Now this is not to say I don’t think stuff is frothy, as I clearly do. But I think the weirding has so confused markets that who knows when contagion bubble popping is going to hit for real. I don’t think we are there yet.

And indeed I started this post in the morning and by market close stuff kinda bounced. Maybe a dead cat bounce. But who even knows is my point. I don’t think we will see a genuine correction till a real market leader like Facebook or Microsoft pulls a Worldcom or an Enron. I wouldn’t be shocked if it was Tesla but I ain’t playing that short. I think it’s more likely that “Meta” fucks itself in the transition to the metaverse or whatever and then we get a real systemic crash. Right now no one gives a single fuck if all of crypto goes to zero. We need much bigger game to drive a recession. Systemic Lehman brother shit.

Which is long way of me making an elaborate Community joke. That TV show with the Talk Soup guy. They had a plot where someone misspoke or made a bad joke and the theme at their community college dance was “Bear Down for Midterms” and no it isn’t a real phrase. My basic feeling on a recession is that the Fed will toss us a couple rate hikes to deal with inflation. But half of America is convinced the pandemic isn’t over. Congress could be talked into more stimulus since the midterms are bearing down on us and well the Democrats are going to lose. The exponential age, the end of American empire and global weirding means no one knows what is going on. The next real marker on our calendar is the midterms. So bear down for midterms. I’ll be wash trading to get some actual cost basis losses till then.

Categories
Emotional Work Preparedness

Day 380 and Decisive

I’ve felt decisive recently. I’ve been confronting significant and life changing decisions the last few weeks and sailing through them. I’ve never felt more at ease making commitments in my life.

It’s not that I’m particularly prone to paralysis by analysis. Generally I’ve been able to move quickly and without undue agony over my choices. But I think within the last two months I’ve simply got my limit with taking the safe course. Maybe it’s a Covid thing and now that I’ve both been vaccinated and had an infection I no longer feel like I can continue with the same safety practices that the early pandemic did. With the election over and the existential threats of insurrections and instability now existing as a permanent worry, I just put off major decisions. I can’t wait for better times or more information. I need to live adaptability now.

So I bought a house. I committed to the process of buying land in another state for a long term resilience based homestead. I’ve planned trips travel. And not nearby regions like travel. I’m going international. I’m meeting people I haven’t seen for years. In some cases I’m meeting people I’ve only ever known online because socializing has been entirely remote for going on three years. That’s an inhumane way to live for extended periods. Even the most introverted person still needs connections. I’ve started making decisions to live my life. I need to live like a future exists or I will never ever escape. As soon as I made the decision to believe in a future again decisions flowed easily.

Categories
Politics

Day 379 and Red vs Blue Poverty

I’ve been scouting for homesteads so I have been making forays further from the city enclaves and blue liberal towns that are my normal haunts and out into rural America. Poverty in the context of blue cities has generally meant homelessness and panhandling. But poverty in rural america looks different.

NIMBY (not in our neighborhood) cities won’t let you just pull up a double wide on the outskirts of town. That brings down property values. I mean theoretically so does tent cities, but that’s an argument for another day. But I haven’t really seen a lot of RVs or mobile homes simply because I’ve lived in yuppie Boomer cities. NIMBY land has “standards” and if you can’t meet them we’d rather you be unhoused than accommodate uglier but more humane options.

As I’ve driven through industrial western cities I’ve seen a fuck ton more rural poverty than I expected. Which is naive and stupid of me. I’m aware of median American incomes. Not everyone can afford suburban townhouses and most developers aren’t interested in building that kind of housing outside of well gentrified places.

As I’ve gone further afield to towns that rely on commodity products like oil or minerals or cattle, I’ve noticed a reliance on temporary or low cost housing. You see a lot of decent well maintained working trucks. But a lot of the housing is as bare bones as you can imagine. And it’s ugly as sin to the NIMBY eye but at least it’s fucking housing. I’ve seen a lot of trailers in various states of decay but I’ve got to imagine it’s better than a tent.

I don’t have a real point here other than to say that America is hurting. No one can afford inflation and if we’ve got stagnating opportunities it’s going to blow up in our faces. Blue cities should be embarrassed as fuck by allowing massive unhoused populations when we’ve got prefabricated options. But the American crumbling is bad in any form.