Categories
Finance Startups

Day 649 and Build in Public

People love building in public. The universe loves a specific ask. Today for my 39th birthday, I am doing both.

I would like to raise $5m for chaotic.capital’s rolling fund before I turn 40 next year. #5Before40 has a nice ring as a hashtag right?

Chaotic is the first check into founders and companies that adapt humanity to complexity. Personal flexibility, organizational agility, and societal sustainability.

Our founders capitalize on chaos.

You may have noticed I’m a bit of a doomer. I keep close tabs on the opportunities presented by an increasingly unstable world.

Climate change, distrust of institutions, geopolitical unrest, resource scarcity, rising tides of populism. There are founders who can help us address and survive these pressing issues.

My goal is to raise $500K per quarter via a rolling fund. There is 155K per quarter committed from folk like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company.

With a base like that, I want to do the rest in public here on the blog and Twitter. You can read the fund overview here. Building in public has generally been my preference and it has felt weird doing any of this fund work quietly behind the scenes.

You can sign up on Angellist through the above link or get on a call with me and we can discuss the fund, our portfolio construction and my thesis.

I’ve got big ambitions for accelerating into maturity as I have no intention of letting entropy win.

Humanity deserves progress, and I demand growth for myself. I’d like to make us both money with that. 

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FAQ TIMES

Haven’t you been investing through chaotic before? 

Yes but just with personal capital and an SPV. I want to scale it up as we believe our performance warrants it.

Go check out some of our best investments here. https://chaotic.capital/fund-overview

______________________

Why didn’t you raise more during good times? Why the fuck are you raising a rolling fund at the end of the world?

Did you miss the part where I am a Doomer? We are a bad times fund. This moment is where our thesis matters.

Good times return and you’ll appreciate having written a hedge check or two into weird companies that are designed for the power laws of institutional chaos.

Or if the fear of the moment feels overwhelming you can sit back and die the slow death of uncertainty. Trust me I’ve considered it as well.

But personally, I’d write me $10,000 check and come along for the climb back. Entropy only wins if we don’t fight back.

Categories
Emotional Work

Day 648 and Open

I share a lot of myself online. For an introvert with more than a hint of Autism you’d think I’d find it mortifying to be as open as I am online. My therapist would probably say it’s because I like the distance provided by sharing online and it’s hard to disagree. But I like being open to the world. I want to be a little beacon in the storm so that you might find me if you are looking.

But while I am so open to the public online, I am protective of my personal space for a number of reasons. I guard my health and my body as I manage a chronic disease. I prefer to operate from a place of non-reactivity as I like my central nervous system to maintain eustress. And I am not generally energized by spending time with others. I am energized by alone time.

But like any other human I do want to be seen. And I want others to feel like I am seeing them. I prize empathy and openness. Showing my vulnerability and weaknesses with the world is part of how I try to be seen and also let others know I see them.

My efforts to be healthy and my struggles with pain and fat are human problems. Maybe other aspects of my life are less relatable, but being worried about my weight and struggling with physical discomfort is the stuff of being an average woman.

I am perhaps overly sensitive to what I perceive as failures and short comings. I project confidence but it isn’t always natural. But I also recognize that, even if flaws terrify the part of me that is still emotionally a child, these supposed failings are the human condition. Everyone has elements of their bodies, their emotions and their intellect that they occasionally feel shame about. We are all working to let go of that shame.

I want the people I work with, especially the founders who are pouring their lives into their companies, to know that they are psychologically safe with me. Doing new things is hard. Creation is hard. Building is hard. Startups are hard. Shouldn’t your investors and advisors be a safe harbor to share those challenges with?

If you are feeling scared or ashamed or angry about yourself, I want you to know you are not alone. It’s ok to be open about your power and your accomplishments and your unique genius. And it’s also ok to be open about all the things you struggle with as well. You contain multitudes.

So if you see me putting out huge asks online or sharing incredibly embarrassing details, I want you to know it is because I see you and I trust you to see me too.

And if we are meant to be in each others lives then it will because we are capable of seeing the multitudes in each other. And if that is not for you that’s ok too. We all deserve to be loved as we are. I trust you. And I hope you might trust me too.

Categories
Emotional Work

Day 647 and Socializing

I thought I was being quite careful this weekend about not over socializing. Last weekend I was hitting up pancake breakfasts and running errands and I thought I was going to pass out come Monday. So I was much more conscious of needing to rest and privacy this weekend.

But no matter how much I dial it back it seems like any amount of interaction is just too much. I backed it down to two hours on Thursday, Friday and Sunday with a recovery day on Saturday. But here I am on Sunday afternoon fighting off a migraine from overstimulation.

Folks bitch and moan about Zoom and how it takes away from the human element of interaction but fuck me if that isn’t the entire appeal of it to me. I myself prefer asynchronous communication to buffer myself even further from the onslaught of audio, visual and emotional inputs. But I’ll take a day full of Zooms as it’s still so much less input.

Perhaps the downside of having the hair trigger central nervous system of an autist is I am simply absorbing more from the inputs than the average person. Every noise, every visual cue, every smell is hitting me. Others may need all those cues but I absolutely do not.

I wish there were a way to articulate this to friends and family that didn’t make people feel rejected. But socializing in person is simply so taxing for me that I need much less of it. And it’s not because I don’t like you. It is just because I’m absorbing way more of you than you think!

Categories
Aesthetics

Day 646 and Birthday Shopping

My birthday is next Tuesday and I’ve been using it as an excuse to browse my favorite cosmetic and clothing websites. I should treat myself right? No gift is better than what you select for yourself. Plus, I love a free gift with purchase. A birthday is often the anchor of any decent loyalty program so I’m justifying this as an exploration of current merchandising trends.

Sephora in particular has dedicated itself to a Birthday Gift franchise that women obsess over all year. If you are part of their loyalty program called Beauty Insider or Very Important Beauty (VIB if you spend $350) you get to chose a gift during your birthday month. There are a lot of other perks in the program but the birthday gift doesn’t require spending any of your hard earned rewards points and it’s free to join.

Sephora’s Loyalty Program Birthday Gift Options for 2022 for VIB & VIB Rouge included Laura Mercier, Tatcha, Amika, NEST & Olaplex

It’s a big deal for the brands to be selected as one of the gifts for the year by Sephora as it’s a great way to get sampling and visibility for twelve straight months. Plus Sephora kicks in on some of the hard costs. It’s one of the better gauges in the cosmetics industry of who is up and coming and desirable, but also has enough cachet that it drives desire around the program.

They generally offer one color cosmetic, one skincare brand, one haircare brand and a fragrance but it can be a bit mix and match depending on what trends are in the industry overall. And they offer up slightly fancier rewards for the $350 and $1000 spending tiers.

This year haircare brand Olaplex was so popular as a VIB gift that only January birthdays got the gifts causing some angst. That slicked back clean girl aesthetic bun TikTok wave and the brand’s IPO last year might have been too much demand for it to be a part of a loyalty program that is intensely scrutinized.

I have actually never used Olaplex as I’ve got low maintenance princess hair. I would have loved to try it in a sample gift just to see but the merchandising gods said sorry girl you ain’t a Pisces.

I’ll admit I was pretty bummed as it was advertised all year but I only realized it was sold out when I was able to begin my own birthday gift selection process. Guess I should have kept closer tabs on the beauty influencers.

Charlotte Tilbury Sephora Birthday Set with Pillow Talk mini Matte Lipstick and Mascara

Because I am VIB I had access to a gift that wasn’t initially pictured in the Birthday section. My theory is it got added in after the Olaplex debacle but this is just me putting on a tinfoil hat. I ended up selecting the Charlotte Tilbury gift. When I was the CEO of Stowaway Cosmetics we duped their best selling shade Pillow Talk many years ago.

I’d never actually purchased the original one from Tilbury as I simply had access to the original source contract manufacturer. I never tried it in matte as Stowaway’s original formula was a satin, so I thought “let’s select this” as my gift for the year. I thought it was a nice throwback to remember a time when I wasn’t a civilian but had access to all the cosmetics I wanted straight from the factory. And yes I miss it but not necessarily enough to go back. But I’ll let you know if I like the lipstick!

Categories
Startups

Day 645 and Progress

I was recounting a few pieces of work that have been ongoing to some family last night. Both items were the result of choices and trends I’d been following and cultivating for well over two years. One of the items was even set to debut next week. I had some demonstrable proof points that I was right and right long before anyone else took any notice.

I was extremely pleased to recount the long arc of work that had gone into these trend lines and how they were manifesting in successful investments and media attention now.

Usually when someone asks me what I do I have a tendency to stumble around a few more or less goofy bits. I am retired from working in propaganda. I am a house wife that manages the family budget (this works only with stay at home mom or high net work wealth managers). If I’m feeling chatty I explain the Thursday Styles Problem. If I’m not feeling chatty I’ll just say I’m an investor. Occasionally I will make an attempt to explain the founder to angel investor to venture capitalist career arc.

It’s not actually that easy explaining work that involves years of waiting. If you work for an established name brand venture capital firm it’s probably easier than being an angel investor with a small syndicate or seed fund. But even if you are Sequoia it still takes a decade on average to prove out your bets.

I’m thrilled to have concrete examples to point with any of my investment thesis points. I’m lucky that I have exposure to media so I occasionally get the chance to share what I work on online and in print. Not everyone has the skills to be as visible as I am. But it sure felt great to make some progress. And yes I promise I’ll share publicly when I can.

Categories
Culture Politics

Day 644 and Status Equivalence and DAO Leadership

Capitalism has largely been a triumph of hierarchy as an organizing mechanism. As we evolved from mercantilism into corporatism, appointing and holding accountable a single point of failure in a chief executive officer has become an effective shortcut for managing complexity when deploying capital. Leadership is responsible for the outcome.

The aphorism “failure is an orphan but success has many fathers” abuts against the reality that while we love to lavish praise upon executives, monarchs and other singular nexuses of responsibility it’s often not reflected in reality. Our bias in the post-industrial revolution has been towards leadership via individual even as post Enlightenment values valorize democracy and community participation. It’s been a tension for since the Industrial Revolution. America exemplifies this as the country most committed to both participatory federalism and corporate capitalism.

I am particularly interested in this tension as I believe we may be on the crux of larger organizational needs and are seeing them begin to coalesce in crypto. As decentralized autonomous organizations, or DAOs, make an attempt to become the new corporate governance structure in Web3, it seems worth studying the question of whether leadership is a singular or collective exercise for humans.

What does the historical and anthropological record have to say about how we organize? What are we evolved to prefer and are we capable of evolving further?

The bias we operate with now is great man theory. But what if that is not just wrong but not even the predominant form of human organization through history? Critics of cooperation might do well to explore this in particular.

I came across a Rob Henderson blog post which is an extended overview of a piece of sociology Hierarchy in the Forest: The Evolution of Egalitarian Behavior by the UCLA anthropologist Christopher Boehm. According to Rob’s post, the main question of this work is whether humans are by nature hierarchical or egalitarian. And it turns out our hunter gatherer forefathers were mostly egalitarian. The bulk of our history is egalitarian.

The anthropological record along with research on extant modern hunter-gatherers suggests that for most of human history we have been egalitarian, defined as “status equivalency among the decision-makers of a group.”

Rob Henderson reviews Hierarchy in the Forest

If you extrapolate this into a modern corporate context, the C-Suite or executive team, or perhaps even the founding team, are roughly the status equivalent decision makers. Maybe there is a first among equals in the CEO or founder but they can, in theory, be replaced by a board. But what if instead of a C-corporation you are managing a cooperative like a DAO? What then?

Apparently we humans are rather good at maintaining status equivalence. Richard Wrangham’s Goodness Paradox discusses how humans have self domesticated to avoid too much resource and power aggregation.

Over time, early humans eliminated those who were overtly aggressive. They killed or ostracized upstarts hungry for power; men with aggressive political ambitions. Other men would quietly organize to commit collective murder of troublesome male

Rob Henderson on Goodness Paradox

Moral communities evolve and punish those who deviate from acceptable standards. If you are too ambitious as an individual we swoop in as a species. It seems a bit miraculous in that light that we live in an era of kleptocracy and power consolidation given our tendency to murder upstarts. Great man theory isn’t all that sustainable. Or is it? Perhaps it’s that we asset influence obliquely. I’d wager any woman would agree.

Oftentimes, headmen display “self-effacing” behavior. Headmen and informal leaders usually obtained their roles through talent in hunting or warfare, storytelling ability, or congeniality. They rarely assert direct authority.

Rob Henderson on Boehm

If indirect authority is a sustainable organizational preference in the anthropological record, perhaps corporations are more amenable to reconstruction as DAOs (decentralized autonomous organizations) through the principle of status equivalence.

The autonomous part seems the trickiest, but decentralized authority inside tribal organizations are at least recognizably human. If as a group we disliked a status or resource hungry “great man” we leaned on the leadership preferences of status equivalent equals and forced you out.

I see no reason we can’t write in similar parameters into a smart contract as an experiment. At the first hint of a rug pull let the burning begin! We are already seeing political battles for resource allocation inside bigger organizations like MakerDAO. Crypto may be a worthy space for experienced leadership to show that figureheads like CEOs or founders are not the crucial lynchpin for progress and stability we believe.

Which would be quite a balm to me personally as I’m deeply skeptical of authoritarianism as a solution for our technical and social problems. I’d much rather we explore the wisdom of past tribal knowledge to guide us than look to a mythical great man to save me.

Categories
Emotional Work

Day 643 and Courage

My courage is uneven at the moment. I have a specific professional project that I am struggling to push myself on. I tell myself that it is something I want, but if the truism “having is evidence of wanting” is any indication, I am struggling to convince myself I really want it. Except I am fairly sure I do want it and I’m just scared.

I used to love it when people said no to me. I was the kind of “chip on my shoulder” young person that used a no to fuel myself. “I’ll show them” was somewhere between a mantra and a battle cry.

But now I find myself anxious to publicly go out and see just how many people will say no. I don’t know if I find it as motivating as I used to. I tell myself I don’t mind but perhaps some other unexamined element of reaction makes me afraid.

This could all be an elaborate ego protection ruse on my part. Maybe I still love the motivation that comes from no. Maybe I hate it. But I have not really done enough fucking around to find out yet to know one way or other.

My gut instinct is to simply declare in public my goals and a timeline to force myself into it. But then I’ve been working through my tendency to rely on willpower and force to motivate myself. Perhaps a big forcing function will simply send me back into my old coping mechanisms of addictive overwork.

I’ve always punished myself by doing things. If I am anxious I almost always find ways to kick a hornet’s nest to force an action rather than gentle build momentum.

Whatever I do I would prefer I do it with as much gentleness and respect for my inner child as possible. I am prone to abusing my inner child’s feelings by disregarding her fear or her desire to keep distance from the rest of the world. I deserve better than forcing misery onto my inner child.

Categories
Biohacking

Day 642 and Feast

WARNING: I am discussing food and my relationship to food for anyone that has any triggers around food, eating disorders, or disordered eating.

I accidentally didn’t eat anything of substance today. I had some coffee and a banana so just enough to break my fast but not quite so much that I had a meal. The weekend was packed with meals in huge portions due to slightly more socializing and being out of the house than was wise. I really felt it yesterday as we had two very hearty meals planned and I managed to eat maybe a quarter of it.

I have always been a bit of a feast or famine type. Some of this is probably related to some childhood incidents. I’d much rather eat as much as I’d like and then fast for a day or so. I like the feeling of choice and control.

Some of worst parts of having to combat an autoimmune disorder is sometimes being put on medications that need to be taken with food. I hate when any outside force interferes with my body. Even medication.

I also happen to buy into the research that fasting is a a generally positive force for good health. The intuitive notion that we evolved for feast or famine is slowly being proven out. Every major world religion incorporating fast as a component also reassures. Nothing is more lindy than fasting.

But as I come to the end of my day it is probably time to eat a proper meal. My stomach is rumbling. I can feel my focus faltering. I don’t have much of an appetite but I will need to find the middle ground between feast and famine today.

Categories
Emotional Work

Day 641 and Recovery

This might sound a little shocking but I sleep at least 9 hours a night. Sleep is one of the obsessions of the biohacker. If I’m lucky I might be able to get to ten. It’s always a sign of me doing poorly if I am not sleeping a TON.

It’s usually the first sign I am not adequately reserving time to bring down my central nervous system into rest and digest. I’ll stay up till 11pm and then it’s a hop skip and a jump to only sleeping seven hours.

The best combination of effort and exertion for me is only adding in specific necessary stressors during the day and give ample time to recovery. Much of my work requires focus and information processing and synthesis. And that isn’t improved by overwork and exhaustion.

Nevertheless I am still carting around a lot of lessons from my childhood about the value of hard work. More is better. More hours is best. And this is a fine and noble thing if you do work intelligently with your goals in mind. Simple exertion is sometimes the best option. But not always.

Categories
Aesthetics

Day 640 and Weekend

Maybe it’s a function of having never owned a home before we bought the Montana homestead, but I was never much of a weekend errands person.

Now my weekends are all about errands. It started with doing a weekly grocery run. Now that groceries aren’t just being delivered to us demand by Whole Foods (the closest one is probably a thousand miles away) we’ve got a standing Sunday drive into town to the food coop. We do actual meal planning now.

And if you give a mouse a cookie he’s going to want some milk. If you give a yuppie a drive into town…We just keep tacking errands onto the drive into town. To do list and errands are the milk to the cookie of the drive into town.

We are still in the process of settling in to our house, so naturally Home Depot is heavy in our errands rotation. Today it was floor lamps and scones for the guest rooms. Last week it was a new pump for our hydroponic system. We basically always have something that requires a Home Depot Run.

We also needed a few other sundry items for our elaborate hospitality driven guest room project. We want our friends and family to feel comfortable coming to stay with us so we have dedicated quite a bit of time and resources into designing and planning for turning our upstairs into a hotel. This is going to be ongoing for sometime as furniture is a pain in the ass these days.

To check off design and toiletry items we hit up World Market and then Ulta. We came away remembering that shopping used to be a fun browsable experience and also a little poorer as we picked up an entire screen printed photo canvas we didn’t intend on buying but kind of love. We also got a very nice set up of brushes, anti-frizz hair turbans, and makeup remover towels for the guest bath.

A bathroom cabinet with hair towels, hair dryer, a round brush and a flat brush.