Tag: Finance

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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. 

______________________

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.

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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.

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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
Preparedness Startups

Day 632 and The Yips

I think I might have a case of the yips. If you aren’t familiar with the term, it’s most commonly referred to as type of performance anxiety associated with experienced athletes. They suddenly find themselves unable follow through on techniques they otherwise know well.

Though as it turns out it’s not actually a form of anxiety at all, but rather a failure to consistently execute on muscle memory in experienced professionals which manifests as a loss of fine motor skills or a struggle to follow through on common chains of decision making, especially ones that are subconscious.

You might also associate it with analysis paralysis, a phenomenon in which someone has access to all relevant information but gets lost in decision making rather than simply acting on their reasonable informed instinct. One’s ability to simply execute what is in front of them is diminished not through lack of knowledge of experience but rather inaction.

I am an experienced startup operator. I am also a competent angel and early stage investor in private markets with a speciality in technology driven businesses. At this point, I’m not only well into my career with a number of concrete successes (I’ve built and sold companies) but I’ve also got generational memory from being the daughter of a startup operator. And yet I’m still nervous about swimming into the deep end of my investing career. I’ve got the the yips.

I hadn’t noticed that I had the yips till I came back from a wilderness medical incident technician certification course. I was doing a hands on course meant for front line first responders in rural and back country scenarios. It was heavy on scene and scenario execution so you could build muscle memory and quick response times.

In medical emergencies, especially in a wilderness context, you have limited resources and personnel. Acting swiftly with the knowledge and materials at hand is crucial. If you don’t take action, someone will die. Startups are famously resource constrained environments. Paul Graham of Y Combinator has an entire framework that assume you are default dead unless you take action to assure survival. This is as as applicable mindset for wilderness survival as it is for startups.

I had some sort of instinctual foresight that this wilderness medicine course would be useful not only practically in day to day life as someone who lives in Montana, but also as a mindset for my investing work on the chaotic thesis that the world is getting more complex. And that complexity has consequences for all of us.

The more chaotic the world, the harder it is to act with confidence as complexity builds.

Only by getting outside of my own skill set and professional world did I finally see how much I’m holding myself back from acting. Whether it is out of fear or analysis paralysis I do not know. But I do know that if one does not act the consequences can be dire. We are all default dead unless we make decisions to remain alive. There is no safety or progress to be found by staring at your problems and becoming overwhelmed by the challenge. If there is a cure for the yips it is to simply keep playing no matter how hard the game becomes.

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Finance Preparedness

Day 608 and What Timeline

I’ve been obsessed with a movie called Margin Call this summer. If you haven’t seen it, well it’s on Netflix, and it’s an exceptional piece of cinema with a top notch cast reflecting on why finance is so prone to boom and busts. It’s a great office drama even if you have no interest in banking. And it’s only an hour and forty odd minutes w two key Pete Davidson SNL skit criteria. It is both Tucci Gang and a Short Ass Movie.

One of the clincher scenes is Jeremy Irons explaining his job as the bank’s CEO to Zachary Quinto the young rocket scientist turned risk analyst.

I’m here for one reason and one reason alone. I’m here to guess what the music might do a week, a month, a year from now. That’s it. Nothing more. And standing here tonight, I’m afraid that I don’t hear; a; thing. Just — silence

Margin Call

I found this particular scene rather riveting as it reflects both the seeming ease and intense dangers of being in charge. Your entire job boils down to making a few big calls exactly right over a time horizon your average working stiff doesn’t even have the luxury to consider.

I’ve been considering my own preferred time frame on which to make decisions. I’m no Jeremy Irons. I don’t make exceptional calls on what will happen in a few months. I do however have quite a nose for what will unfold over much longer time horizons. I’d trust myself to make the right call over a decade. I scan the horizons.

Which if you are following along with some of my life choices should be modestly unsettling. I moved to Montana to a rural homestead. I invest in early stage startups that fit my chaotic thesis. I am comfortable being labeled a doomer and a prepper because catastrophic emergencies are in inevitability in complex systems.

And it’s hard to imagine a time when complex systems like climate change, geopolitics and macroeconomic trading pressure held more sway than now. Like Jeremy Iron’s character I am listening for the music. And my ear is trained on the silence coming down the pike.

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Finance

Day 590 and Demography

User acquisition is my little niche in the startup world. While all founders are generalists my super power has always been getting the attention of customers. So I often enjoy little illustrative moments where basic principles of finding and speaking to your audience go awry.

I have tweeted extensively about my concern in the rising cost of core agriculture commodities in the face of shitstorm in the fertilizer markets. This isn’t that novel if you work in finance but it’s probably not a large group of people that are actively discussing fertilizer costs. I do not however buy fertilizer personally. I don’t finance it.

In the face of rising interest rates, partnering with Nutrien Financial™ can help you prepare for the future with confidence. Our latest blog post explores why financing your input purchases may be beneficial to your operation:🔗 nutrienagsolutions.com/blog/5-Reasons… #AgFinancing

I was served a tweet for Nutrien Financial. They would like me to consider financing my crop inputs. In fairness to this promoted tweet the final demographic detail Twitter may know about me is that I live on rural land with agricultural use zoning. I see how I got targeted. And I am delighted to be served this piece of thought leadership from them. But I’m not in anyway their customers base even though I mimic a lot that matches them.

Let’s compare this to another group of advertisements that targeted me this week. I got several pieces of direct mail in my physical USPS post. These folks knew that I had recently purchased a forwarding service from the USPS to make sure old post from my former Colorado address would reach my new one in Montana. Let’s take a look at what they advertised to me based on that piece of information.

A spread of several catalogs and promotional mailers for home furniture, blinds and window treatments and rural road paving services.

It looks likes advertisers who want to reach married couples that have recently forwarded their mail to a new address might be in the market for furniture, window treatments and also I guess rural road paving services. That one might be a rural Montana thing so slightly more niche.

Advertisers argue a lot about high intent audiences. That basically means someone who is likely to buy your product or service. Lots of people can fall into the typical demographic of what you sell but judging if if they are likely to be persuaded to make a purchase can save you a lot of money. Don’t sell to someone who isn’t buying.

Sure you can convince someone they want something with aspirations and glamour but you have to be able to be convinced. It’s a lot easier to do that for a lipstick than a couch. Significantly harder to do for rural road paving I imagine (though I’ve never done it so I can’t be sure). The hardest has got to be financial products for large scale industrial agriculture purchases. Finding people with high intent to buy fertilizer seems pretty specific.

Marketers can and do try to gussy up these facts with fancy languages but getting attention and selling to people that want to pay attention are basic. I’m not the tactics aren’t complex and the work can’t get extremely technical but at least we know we are working with human desires. And I think it’s important to think through that when planning a campaign. Don’t want to overspend on convincing someone who isn’t even in the market to be convinced.

Categories
Aesthetics Finance

Day 584 and Fraudsters

I hadn’t bothered watching any of the numerous Netflix documentaries on how Americans love a beautiful fraud until this weekend when I made an attempt to watch Inventing Anna. I can’t tell if I regret the decision. I’ve avoided any glamorizing of the various grifters that we love to hate.

I don’t love stories about hustles gone bad because I fundamentally believe the difference between success and failure is a lot thinner than than the average person knows. “Fake it to you make it” is part of the great Pentecostal American prosperity gospel. You can come from nothing and become someone in America. We worship the idea of social mobility even if we don’t always like how people gained their fortunes. It’s an entire aesthetic in America.

This is particularly true because sometimes we actually do let the fraudsters win. Especially if we admire their hustle. And let’s be frank it’s a lot harder to tell who is a fraud these days because decades of publicly being a fraud doesn’t stop you from sitting in the Oval Office anymore.

Is it any wonder we aren’t quite sure how to feel about wealth and privilege and the black magic required to obtain it? We act like fraud is a temporarily embarrassing discovery on the way to respectability. Because it often fucking is.

Being in startups has given me a front row seat to just how much talent and capability matter. Except when they absolutely don’t. It’s genuinely hard to reconcile how little effort and outcome can be correlated occasionally.

And this absolutely lends itself to people being willing to take shortcuts. Mistaking that some hard doesn’t pay will kill you if you aren’t able to stay one step ahead. If you get caught, well that is clearly bad but who is to say you couldn’t have kept it up? It’s not like Americans trust cops or prosecutors (except for the line blue line fetishists). Maybe you were just too much of a loud mouth.

I will say the Inventing Anna series has shown me Americans are genuinely confused on how the rich stay rich. In so far as I can tell it boils down to gambling on who might be the real deal and simply writing off the frauds.

Cost of doing business. It happens to everyone. And the worse your boundaries are, well, the worse off your percentages. If your bullshit radar is bad that’s how generational wealth disappears unless you can figure out a way to rig the system (which is always an option).

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Preparedness

Day 506 and Walking The Talk

I had a spectacular two weeks of writing from the deepest places in my soul. We made significant and long lasting decisions for the family and the direction we want to take our lives and our investments. And yes I do mean that my husband and I are moving to Montana. One day I’ll be so proud to have captured that moment in our lives on paper.

So of course this past week I’ve done nothing but worry and fret and write about that worry as my physical body decided it was safe to be a bit sick now that we’ve done that hard work on making a big life decision. Even that mess of feverish writing ended up delivering some amusing written insights.

I’ve had to remind myself basically hourly that I’m alright. That all the uncertainty of the world is something I can live with. Indeed, it’s something I’ve planned for over the course of years. When I jokingly insisted we should name our family office chaotic.capital it seemed like an amusing and edgy piece of branding. Now I’m caught up in the reality of just how fast the thesis is playing out.

Frankly I am scared. I am scared because I can see just how hard things will be. Some days I feel like I’m beyond excited to actually be right. But then I remember the chaotic thesis sucks to live through even with the best resources and preparation. And all I can really do is walk the talk. Nothing is as terrifying as being prepared for hard times and then simply having to live all the shit you said would happen.

Because of course all of the macro big picture things that I’m planning to invest against are things that make my life harder too. I’m disabled with a chronic health condition that is annoying to manage in good times. My personal wealth is subject to the same market forces as yours. I have had to deal with the overheated housing market as a non-homeowner. I still have to act in the same face of the fears as everyone else. Am I modestly protected and buffered by privilege? Yes I’ve been sprinting to acquire it for year to get it. But here we all are and now is the time when a steady hand with a prepared mind can thrive.

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Internet Culture

Day 469 and the Discourse

On the one hand, the discourse today is horrible. Elon Musk threatening to buy Twitter is breaking people’s fucking minds. On the other hand, it’s the height of culture to be so singularly obsessed with a topic of such little consequence. The zeitgeist is full on psychotic.

This isn’t about free speech. Fuck that. No one gives that much of a shit about corporate governance that they’d super impose a civilizational problem like free speech onto securities law. This isn’t an episode of Billions. In except that both make me want to scream “that’s not how this works, not how any of it works” into the void.

This is all an elaborate publicity stunt to feed the narcissism driven logic of markets obsessed with celebrity and personality. Because everyone knows what everyone knows, pricing discovery is a function of lurching forward a narrative for the vox popli. Except everyone is convinced they are uniquely brilliant so they can’t possibly also be manipulated by the transparent agitprop. Yeah yeah sure I’m a galaxy brain too. We’re all playing 4D chess. Everyone is winning and the markets only go up.

Categories
Internet Culture Preparedness Travel

Day 464 and Miami

Miami is a real American city. You know those criticisms lobbed by conservatives against New York, San Francisco and Los Angeles? It’s not a real American city. It’s bullshit in plenty of ways as our urban populations define America as much as rural, but it’s also true. Places like Miami maintain an essence, a kind of “here-ness” that reveals a thriving ecosystem of all classes, backgrounds and beliefs living in the same place.

It’s a thriving cosmopolitan city with an extremely wealth ruling class. It has welcomed it’s new leadership in the form of startup expats from “fake cities” moving in. The irony is that those are fake places and no one lives there. It’s transient wealth moving in and out for opportunities. Which is exactly what they are doing to Miami. The churn comes for us all. Before it was tech it was drug money and mortgages. It’s a free enterprise kind of place.

But it’s a relief to see mix of people. To see the shitty neighborhoods and the anxiety about crime, reminds you we have to do better for each other. To see the luxury houses and the amenity industry pop up to service everyone rich from yuppie to billionaire. It’s a vibrancy of hustle that isn’t everywhere. It’s a positive thing. For me it smells like America. A belief in the future where things could be better. A sense that capitalism is working.

As I write this my Uber driver is complaining about the local cops. How unfair their targeting is of everyone going too fast. A real class solidarity moment against the fuzz. Lambo owners and ride share drivers. I feel like that doesn’t happen in striated societies where the top use the police to torture their plebeian neighbors.

I didn’t really enjoy my time here. It’s way too hot. It’s facing intense pressures from climate change so I’d like to come more often before it’s too late. It it’s already too late maybe.

There really are issues related to inequality and the challenges it manifests via societal issues. It’s got crime and infrastructure issues and intense political culture war currents.

If I’m honest I’d rather be in a colder less populated state where some of the existential risks of the future are better mitigated. But I admire the optimism of people who do. They are the optimistic people we need for a better future.