Tag: Work

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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.

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Emotional Work Startups

Day 402 and The Most Me

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.”

How I Attained Persistent Self Love

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.

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Emotional Work

Day 401 and Clarity

Life is a pretty indecisive process. You go through with, at best, some genetic heuristics for truth and a couple half verified data sets. So when the feeling of clarity hits you it’s hard not to notice. The clarion call of seeing reality (which sounds like me mixing two sense based metaphors) is edifying.

When you know you know. Popular culture loves this phenomenon. You get it. Knowing is head to toes and taint to tip stuff. You just get what’s happening in your gut. Somewhere in the shared brain space of your conscious reality and the microbiology of your intestinal fauna there exists clarity.

Surely there is a reason we describe knowing as a process that isn’t strictly data driven. Sure we can have facts and methods and process. But somewhere along the line we can only know if our biology agrees. Your gut knows what I mean.

I had a bit of that feeling earlier today. I got some feedback from someone I like and trust. It wasn’t positive feedback. Me and mine had fucked up something in our approach. But then I had clarity. I knew what we needed to do to fix it. I saw the path that would lead to our success together. And I just knew it. In every part of me. And the best part is when I share it with my partner they will get it too. In their mind and body. That’s clarity.

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Preparedness

Day 399 and Life Finds A Way

Postlapsarian literature is arguably the first type of story in the human mind. A fall takes place. What comes after? Paradise Lost is an entire genre of folklore. I’ve been watching the new Station Eleven television show having made that mistake of reading the book early in the pandemic. I say mistake because it’s an emotional book.

Maybe it’s America’s obsession with second acts that gives me optimism. We will have a fall. A shuffling towards Bethlehem style shambles perhaps. But we will rise. Our national bird has never been the bald eagle. It’s been the phoenix.

Maybe this is why we tolerate horrible work conditions and miserable days fighting our fellow man for a scrap of security. Because as the saying goes, each of us is only a temporarily embarrassed billionaire. Don’t worry we will be back. The show must go on.

And so we concoct elaborate fantasies about how this too will pass. One day our chronic poor health will get better. Just you wait. We believe in science here you see. Science means an Epcot better tomorrow just hang in there.

Our Hollywood fantasies are riddled with “life finds a way” punchlines because well the struggle for survival in an inhospitable world is a universal struggle for our species. There is no lost cause.

But also there is no enjoying the moment or savoring the little things in life if we are always watering for our heroic moment in “the after” and holding back in the now. But don’t worry. Life finds a way. And so will you. Just remember that the end of the world is mostly a change in circumstances.

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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.

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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.

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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.