Categories
Emotional Work

Day 329 and Thanksgiving

I have so much to be thankful for this year. I don’t have a lot of poetic thoughts on it, though I have written extensively about my feelings on some of the bigger moments of the year. So click those if you want essays as this is going to be mostly a list.

I’m grateful to have recovered my health in 2021. I’m equally grateful I had the money, support and willpower to achieve it.

I’m grateful I have a husband who understands me and gives me the love, support and freedom to be me.

I’m grateful for having a space to share my thoughts daily, and rather than be punished for speaking my mind, I am rewarded for it. That includes WordPress, Twitter and all the people who made the internet possible.

I’m grateful I can live in Colorado and still do the same work I previously thought I would only do in New York or San Francisco.

I’m grateful my mother sent me to Waldorf school. I’m grateful I have a father who supported my development as a full human being.

I’m grateful I can afford to buy whatever dumb shit I like for my hobbies which range from expensive skincare to preparedness.

I’m grateful I can consider buying a home that will have the capacity to provide safety even as the world around me has risks.

I’m grateful to have business partners who share my vision for investing and founders and entrepreneurs who allow me to help them.

I’m grateful I never have to worry if there is enough money in the bank to buy a book.

I’m grateful that the supply chains have held so that I have an apple pie that I ordered online the day before the biggest holiday of the year which I picked up in my car that I was able to buy even as global trade was strained and our currency was inflated.

I’m grateful for the time to pursue emotional capacity and the money to pay for it.

I’m grateful for chemistry and the wide variety of pharmaceuticals and supplements that I take every day.

I’m grateful for my iPhone, it’s applications and games I use daily on it that have connected me to a world of people virtually that I love as truly as the people I interact with physically.

I’m grateful for shitposting.

I’m grateful William Gibson still writes. And I’m grateful that Twitter has let me interact with my favorite writers.

I’m grateful for West End BBQ and Spruce Confections.

I’m grateful for my raw milk dairy cooperative and it’s farmer Daphne.

I’m grateful for sunscreen and for apple cider vinegar.

I’m grateful for Costco.

I’m grateful for my parents making good decisions when I was younger that have compounded into incredible luck and prosperity for me.

I’m grateful to be American and I’d like that to remain a thing for which I am grateful.

I’m grateful for democracy, the enlightenment, free elections, a free press and liberalism.

Categories
Preparedness

Day 324 and Seneca

I was once asked by someone how I can act so quickly on major life decisions when they needed to mull a change over for months. I found the question confusing as I don’t think of myself as being particularly fast or even impulsive.

Well, that’s a lie, I’m impulsive about lots of shit but never anything of consequences. When it’s a major life decision I gather information for years so if the opportunity presents itself I’m prepared to act immediately. I take the bias towards action seriously.

But I only make a move when I believe I’ve crossed a threshold of information where the benefits of action clearly outweigh the benefits of inaction. I’ll make a move when I think I’ve got a better chance of winning than losing. Or when it’s clear that if I don’t act at all I’ll have a losing hand. But I generally only needs the odds to be tilted to a plurality of probability. Especially if it’s an action I can undo later. It’s not always easy to know if you can win. Sometimes the best you can do is recognize that inaction is weakening your position.

Part of my comfort in my process for taking action is I am a researcher by nature. If I’m interested in a topic I’ll begin with exposure right away. I’ll do the light skimming research the internet has enabled through articles and videos. I’ll dive deeper and purchase books. I’ll find experts in the field and begin following them. If I have questions I’ve got a habit of emailing the source. And then I’ll start doing what I can to implement my research with small scale experiments.

Chances are if you see me making a major move it’s because I’ve been considering the possibility of action for years. I like to be prepared to act immediately if an opportunity presents itself. If a situation presents itself I want to be ready. That way I’m positioned for luck. Seneca had it right. Luck is when preparation meets opportunity. But you can only have luck if you are willing to do the work of preparing and be ready to take action if opportunities present themselves.

Categories
Emotional Work Politics Reading

Day 306 and Shortcuts

I never really thought of myself as a perfectionist. But I have impossibly high standards for myself that may be unproductive.

While I’m sure some of it innate, some of it is nurture. I went to a school system called Waldorf Schools that didn’t have grades. Every child was evaluated against their individual performance and each class was deliberately taught to the best student in the class not to some perceived middle. That’s left me with a habit of always believing I can improve and also the expectation that our average performance must be comparable to the best.

Of course this is unrealistic if one continues to climb up social, economic, intellectual and cultural ladders. I kept looking for my limit and then finding a new mountain to climb. Know I know there will always be mountains. And that perhaps it’s ok to take some shortcuts on your journey.

I really struggle with shortcuts. So am forcing myself into taking some so I can let go of some of my impossible standards.

I don’t scan books. I read them. So I bought a really bad prepper novel and am forcing myself to take shortcuts in pacing and focus. It’s so bad I don’t have a choice. I have to skip a lot or else I just wouldn’t finish.

I had to go to an appointment today. Normally I’d be sure to shower and wash my hair if I need to be in polite company. I showered yesterday but I just didn’t feel like going to the trouble two days in a row. So I put dry shampoo in my hair and opened up weight wipes for my nether regions. I doubt anyone would have noticed but a shortcut in my grooming routine was pretty liberating.

Today is also Election Day. My hometown has a bunch of local ordnance changes and some important bond related measures. It’s also city council elections. I’ve been following all the ballot issues but I just couldn’t find any city council people I liked. I read all the local papers and they all suck. None of them remotely come into my preference wet. So I took a shortcut. I voted on all the ballot issues and left the city council blank. I just wasn’t going to spend any more time picking lesser evil candidates.

These may seem like pretty different issues and maybe I’m also not fully committed to my civic duty (I’d argue as a democracy it’s a right to abstain from a vote if your conscience cannot condone it). But the point is that instead of getting bogged down in every unrealistic expectation I had of myself I could just take a shortcut.

Categories
Startups

Day 305 and Request for Founder

I was having an emotional conversation with a friend. They were giving me a piece of feedback that was truthful but hurt me. Because I feel psychologically safe with them, I was able to take the feedback in a receptive and open manner. I could incorporate it into my mental framework immediately because I trusted my friend. And I knew that their feedback was important and accurate.

One of the traits that I feel is most central to success in founding a company is the ability to process feedback effectively. Founders are constantly getting feedback. An average day might include angry customers with product complaints, a venture capitalist with heartfelt but partially useless advice, an unproductive strategy meeting where no one can seem to align, and a bunch of smart ass shitposters on social media with job advice for you.

A startup CEO gets a lot of feedback. Every day is a deluge of the stuff. And founders have to be gracious about it. Even when a lot of the feedback is useless, or even occasionally downright bad. You as a founder have to decide what to take and what to ignore. Because learning how to synthesize and integrate feedback; positive, negative or even profoundly unhelpful, is in fact your job. Being good at it matters. It’s the closest thing I have to a litmus test as an investor.

This is a trait I prioritize highly in founders. If you yourself are a founder that is working on improving your capacity for feedback processing, I want to hear from you. That mental flexibility is one of the core criteria I look for when I decide on an investment. Do I think you will be able to intake enough information about their market to get to product market fit? Will you be able to adjust your mindset and mental models quickly enough to outrun inertia? How emotionally strong are they that there can hear constant negative input and still hold their positive vision? But equally can you adjust that positive vision when negative feedback that actually matters presents itself.

These are the questions you need to have answers to for yourself. If you can drop me a line on Twitter DM. I’ve got an entire primer on now I like to get to know founders.

Categories
Emotional Work

Day 291 and Self Control

Self control is a form of self abuse for me. Early in life I learned that I could control others by controlling my emotions. Instead of showing my feelings, I’d distort my emotions into whatever got me attention from adults. That’s pretty clever for a child, but is the road to misery once you’ve grown up.

Alas I’ve kept up the habit of self control. It might not look like it from social media or press narratives, but I self censor a lot. I’m often conscious of what others will like or dislike and I will edit my feelings if I feel it isn’t to my benefit. What can I say, I am still hurting from feeling like I wasn’t loved as a child by my father. Same old story that everyone has in their lives (well maybe for you it was your mother but same idea).

But it hurts to keep your emotions inside. Eventually it will turn into pain or sickness. Not that I’m saying all pain or illness is caused by emotions (that’s some bullshit) but the mind body connection is real. The point is it’s only hurting myself to exert so much control over my emotions.

I need to get more comfortable with being uncomfortable with other people and how they feel about me. The control I have is largely a fantasy. It’s not that it’s not possible to change how others perceive you. Hell I’ve picked professions where that’s practically the main skill set. I love the perception game. Public relations, fashion, even venture capital are all games you win by building a good reputation.

Having a good reputation doesn’t mean turning off honesty. If anything reputations are built on being trustworthy. And that generally means saying what you mean and meaning what you say. So I’ve got to stop abusing myself by choking off emotions I don’t think others will like. Maybe it’s a gender thing. I learned pretty quickly no one likes an angry woman. But sometimes I get angry. Whatever excuse I’m using for hiding unpleasant emotions has got to go.

Categories
Finance Startups

Day 275 and Manifesting

I had a really terrific September. Everything just started going my way. Projects that I’d been pushing on had significant breakthroughs. My deals got hot. My focus and health improved. Even when I had setbacks and failures I was able to execute on quick recoveries. But mostly I didn’t give in to past bad habits. And all of that happened without any additional effort on my part.

I’ve been making a really conscious effort to stop pushing myself to always be doing more. Either I am able to find elegant solutions or I ask myself to take a step back till I can. Rather than brute forcing everything I am finding ways get where I am going without sacrificing myself to costly bad trades on my time and energy.

I asked for something really significant from one of my investments (an additional allocation for an special purpose vehicle). The second I asked for it I started to panic. I didn’t have an immediate or simple path to deliver on what I asked for from this founder. Even though I was confident I had the money for the deal it out I panicked that maybe I had bitten off more than I could chew. Immediately it started going through my head about how bad I’d feel if failed this founder. I relived the guilt, shame and punishment I had felt in previous failures to deliver for people that trusted me. I hated feeling like I’d failed people.

And I just decided stopped the cycle of worry then. Like turning off a switch. I told myself I could do it, I knew I could do it or I wouldn’t have asked, and that there was simply no way I was going to let down this founder. But this is where I felt the frown Instead of going into overdrive, I stuck by my schedule. I didn’t change anything. I didn’t push myself to a frenzy by adding in calls, pitches & emails. I just put down all the steps I could and would take to make the deal available to the right people and I began.

In the past I would have let that fear drive me. I would have gone into overwork and adding in additional tactics that I didn’t even need to insure I would reach my goal. But here I trusted myself to get the outcome. I didn’t exhaust myself. I took care of myself. And the allocation got filled quickly. I checked the commitments this morning and I’ve only got 15% of the deal left.

Categories
Emotional Work Internet Culture

Day 263 and I’m Baby

One of my friends got me an embroidered “I’m baby” patch with a Moomintroll holding a knife in place of the original Kirby. It’s an elaborate play on the “I’m Baby” meme and was a truly excellent Christmas gift. I’m a fan of the Finnish children’s author Tove Janson who created the Moomin series and also emotionally baby and my friend knows it.

Original “I’m Baby” Kirby meme vs a photo of my Moonin “I’m Baby” embroidered patch

The “I’m baby” meme is generally a play on why someone should be allowed to continue with their behavior or emotions without consequence. It’s a kind of elaborate joke about wishing to dodge responsibility if only for a few minutes. Obviously it’s very popular with Gen Z but it’s really more about wishing to live in a world where it’s even possible to be a baby when life feels overwhelming.

The original meme came out of an emergency but it’s come to be a kind of wishful demand and hope that one can just well be a baby for a bit and have someone else handle it.

Moomintroll is an excellent stand in for Kirby in the meme because in the Finnish cartoons he never has to live without Moomin Mama. Moomintroll is an archetypal baby. The Moomin universe has constant catastrophe (no seriously there are floods and asteroids) but Moomintroll can always count on Moomin Mama. It’s a soothing set of books for children obviously but it’s also just nice that there are parental figures to which one can turn. That’s a fantasy we all have at some point. Especially when shit looks bad.

But being baby also means someone else has to be the adult. The willful insistence on being baby is about giving your power to someone else. Unless you are literally baby (in which case how are you reading this blog) you’ve chosen to put someone else in the position of power. Which is an important lesson for adulthood. You always have the power. Even if you chose to be baby. Especially if you are baby.

So be careful when you say “I’m baby” and act helpless. You gave up your power. And that’s alright. Being helpless can be a totally cool sex thing and it’s great to chose your kink when. But you’ve got to have consent for that shit. Bringing someone else into your fantasy of being baby might be non-consensual. When my friend jokes that I’m baby it’s because he knows I like to give up my power. But alas it’s a fantasy and I can’t go back to being Moomintroll for real. But it’s a nice patch right?

Categories
Internet Culture

Day 261 and Game Drama

I have been playing a mobile massively multiplayer online game for a couple of years. It’s a pay-to-play game that mashes together every mechanic and trope into one stupidly expensive pile of unoriginal comfort. I absolutely love playing it. It’s called Lords Mobile. It is entirely worth playing if you appreciate the craftsmanship and conversion marketing. It doesn’t gave any unique creativity but that isn’t the point. It’s just perfectly executed to be an engaging game. I cannot recommend this game enough if you want a soothing “everything and the kitchen sink” social game.

Because it asks so little of the gamer intellectually, the appeal of the game is in the community of people. You work in teams of 100 called a guild. This can be a very low key camaraderie situation or the kind of bond where people spend tens of thousands of dollars to compete together in their chosen hobby. Needless to say if you are in the group that really spends real money and time you get to see human nature nakedly on display. It gets wild.

Ive seen guilds explode because a guy was cheating on his girlfriend with another player. That mistress then destroyed 30,00 worth of gear and destroyed the guild. I’ve seen people steal maxed out gaming accounts worth over $100,000 with no recourse. Just poof you trusted someone with your keys. Ooops!

And today I saw three dudes try to convince their guild that the leader of the group was stealing from the guild because she’d allegedly been in sexual relationships with all of them. It doesn’t sound like she stole anything from anyone but they resented that they had spent money on gifts for her account. The guild didn’t believe the dudes. It’s their problem if they want to buy gifts was the general consensus.

The level of human drama is probably even more enthralling than the game. And the game is designed to be very engaging. I don’t watch reality television but I have to imagine it has a similar “oh no she didn’t” spirit. If you enjoy watching the depths of sorrow and the purity of genuine human connection it’s worth a try. Just be warned that you may become emotionally attached. I definitely have. I’ve met some dear friends in these guilds. But I’d recommend you not give anyone your credit card. Or if you do don’t go whining about it to me.

Categories
Emotional Work

Day 256 and Helplessness

When I was a child I hated being helped. I was a “Mary quite contrary” type except I wasn’t yet in a profession where that was considered a sign of intelligence. I’d ignore the advice, aid and help of teachers. I preferred to figure things out on my own.

A story that I’m sure will eventually turn apocryphal as I get older involved a horse trainer and needing to be left alone. I was was having trouble with a jump in a group less. My horse kept throwing me and ducking the obstacle. My trainer did his best to give me advice on how to keep my posture and encourage my horse. He kept piling on advice and kept his focus on me. And I kept not making it over the jump.

I probably fucked it up over a dozen times. Eventually my trainer gave up and went to help another pupil. Without the glare of a professional, I finally gathered myself up, held the horse firmly in hand and soared over the jump on the first try.

Holy shit was my trainer pissed. “Julie didn’t need my help at all! The second I turned my head she just handled it herself.” From then on my trainer learned that I’d happily internalize his training but if he kept too close of an eye on my I’d develop a kind of learned helplessness. I’d get worse and not better.

I sometimes wonder if this tendency remains a part of me. I like attention so I’ll accept help if someone is willing to give it to me. The upside to this is I am always learning and questioning. But if I’m not careful I’ll just keep enjoying the benefits of helplessness. But I can’t linger there. Because I know moment I’m left to my own devices I’ll gather up the knowledge and willpower and make it over the jump. But it can be temping to wallow in helplessness.

Categories
Startups

Day 250 and Getting to Know You

I don’t really like musical theater (it’s the people sorry) but I’ve been humming a tune from The King and I called “Getting to Know You” as I codify my process for meeting founders and startups. It turns out Julie Andrews through Rogers and Hammerstein lyrics may be a viable strategy for finding out if someone is a fit for Chaotic.Capital. The actual play is racist, colonial nonsense but you know take art for art’s sake.

Getting to know you

Getting to feel free and easy

When I am with you

Getting to know what to say

Haven’t you noticed

Suddenly I’m bright and breezy?

Because of all the beautiful and new

Things I’m learning about you

Day by day

She’s talking about being a teacher and getting to know her pupils but it’s also maybe about falling in love, but I like the sentiment that learning “beautiful and new” things “day by day” feels bright, breezy, free and easy. That’s a good template for relationships of all kinds.

Pitching is none of those things. It’s practiced, formal, and exhausting. It may be a necessary evil for founders as you need concise and clear communications about what you are doing and why it requires capital. But I don’t think it’s the best way to get to know people. Getting to know someone should feel easy.

I like to get to know someone over the course of conversations. My preference is through asynchronous communication mediums like chat, direct message or email. There is something about the volleying back and forth of information that helps me more. I like a back and forth that is informed by revealing thought process but also context and background. I’ll chat with virtually anyone and keep my direct messages open on Twitter because I value conversation so much.

I generally don’t feel that phone or video calls are that helpful to me in getting to know someone initially. I don’t mind short 10 minute bursts. What I do dislike is the planned hour long call for an initial conversation. Rarely am I able to be emotionally and physically present for something like that if I am not already interested or invested in story.

But if we’ve had conversations through Twitter, direct message or email where I have more context and connection then it’s possible I can be present for you. But I wouldn’t recommend asking for an hour synchronous medium as your first interaction with me. I’ll do it as a favor to someone now and again but I almost always resent it.

I’d rather get to know you over time before I’m trapped in a room for an hour to put it bluntly. I promise this is for both of our benefit. You wouldn’t take someone on a two week vacation for a second date so why would you hinge your chance to work or get investment from someone by insistence on spending an hour together right off the bat. Let it simmer a bit. Give me an appetite for wanting to help you. Then you won’t be able to get me off the phone or Signal. I will be your most available investor if you take the time to show me who you are.

So go ahead. Message me. Message a bunch. Send an email. If you don’t hear from me message some more. If I’m being evasive tell me straight me. But the end goal should be that getting to know you is free and easy. And you will be able to tell if I’m excited. Don’t give up. Just keep the conversation flowing like Julie Andrew’s did.