Category: Finance

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Finance Startups

Day 180 and Thesis

As I see more pitches and work with more entrepreneurs I am finding it helpful to have my thoughts codified on paper. That way if you are interested in working with me you have a chance to vet me. Knowing what I want to see in a deal and what just isn’t a fit saves entrepreneurs time. So I’m going to doodle a bit on what I do and don’t like.

Chaotic.Capital has 4 key investment areas. But they are really just different levels of working with an uncertain future: at the individual level, the organization level, the systems level and the planetary level.

  • Personal Flexibility is critical when it’s harder to make long term lifestyle decisions (housing, health, children) – how do we allow people to make those decisions without anchoring themselves to place or time horizons that limit optionality. Businesses like marketplaces, preparedness, personal safety, service & product exchanges, health tech, longevity, and alternative credentials.
  • Organizational Agility is a differentiator for businesses in rapidly changing landscapes, so we invest in software and tooling that provides leverage for small teams to have a bigger impact or bigger teams to act more discretely and independently. Businesses like software as a service, cloud infrastructure, collaboration & coordination software, DAOS (decentralized autonomous organizations), automation software, and memetic and organizational aids.
  • Systemic Arbitrage opportunities are even greater in chaos. Working through systems level chaos helps individual and organizations protect against cascade and systemic collapse risk, mitigate political chaos, regulatory uncertainty, memetic crowd and mob behaviors, or medical chaos, just to name a few. Businesses like intelligence, decentralized finance tooling and exchanges, cryptocurrencies, bots & analytics.
  • Climate or planetary risk is an existential risk that is already fucking with our world – we like companies mitigate the chaos of climate change while profiting on the risk. Businesses like mobility, insurance, green tech.

What I don’t like to hear are pitches for things that are tangentially related or a forced connection. Sometimes folks will try to get us excited about a problem they’ve already solved and are scaling but we are looking for longer time horizons. There are plenty of amazing startups that have great returns but aren’t a fit for us. We really do want the crazy weird stuff that is going to take a while.

We don’t need you to know where you are going. We want to see ten or twenty year out timelines. What would life look like without school? How about a world where we didn’t pay taxes based on our geographic location. How about a world where we automate how our attention is allocated. Or a world where our financial power isn’t rooted through centralized trusted powers. We want 1000x leverage on change.

I’ll write more later this week about the types of companies I don’t want to invest in. Not because I don’t like them but because they just don’t match what this fund is meant to do.

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Finance

Day 163 and Favors

Some professional arenas are driven by the favor trading of social capital.

I’ve got a gut sense that this is true on the two poles of commodity products and services. The middle ground has a lot more nuance and is thus less susceptible to favor trading, as it’s clear what drives price and value of service. With complete commodities (identical replacement value) and the non-fungible (not interchangeable or replaceable) there are not simple price or value anchors. This makes it more likely your purchase or choice will be driven by the perception of social capital. We will do favors for those with higher status or by the recommendation of those we trust.

Interchangeable commodity products trade on price, which means favors from across the ecosystem act as the grease in otherwise equivalent deals. Think suppliers of everything from lumber to textiles. If the price is the same maybe you buy from someone you like who took you out to dinner. Or you buy because that person has a good reputation in the community so you use the person your neighbor recommended. This seems intuitively true of commodity services like accounting, plumbing or roofing. Within certain bounds of quality, a 2×4 or a roofing bid should fall into the same bucket so it’s ok to pick whoever feels best. That’s why it’s susceptible to favors and social capital exchange.

On the other end, extremely differentiated non commodity products are equally prone to being tipped by favors. Think professional services like public relations that are very hard to compare. A publicist with favors to trade gets their clients the best coverage. A reporter who has a lot of sources can trade them in to get a quote for a story. Venture capital is one of the least commodified types of capital, a founder will pick one firm over another not just based on the price of a term sheet but whether others recommend them. Reputation matters a lot. Social capital is what gets a deal done, a nudge to consider someone will push you into a cap table.

Not convinced? Think about a product that exists in the middle like clothing from a brand you know but isn’t connected to you in any other way. This is the least susceptible to favor trading or the pressures of social capital.

We can intuit a dress made from quality fabrics and a recognizable brand has a set cost because the brand of the designer is not interchangeable (maybe with others in their category but Prada isn’t the same as Old Navy) and the cost of the fabric is transparent. A silk blouse can’t ever get too cheap on a one off basis. Both the brand and the fabrics set the bounds of the prices.

I didn’t really have a point in writing this other than being curious about what impacts how we pick what to purchase and what sets the bounds of our pricing. We are in a narrative cycle around inflation and work shortages which is having an impact on how willingness to to spend or hire.

So be careful if something seems too expensive but comes highly recommended. Be equally wary if something is particularly cheap even if a friend likes it. Look for the sweet spot of pricing and reputation that is based on market price beyond your in-group.

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Finance

Day 160 and Starting with Money

The best articulation of why anyone gives a shit about currencies in crypto (as opposed to just focusing on bigger structural problems of macroeconomics) is that you need foundational layers to build a new economy. You need a currency before you can have an economy. Ryan Sean Adams at Bankless gave me an aha moment with this quote. You need money.

The bankless model is simple: you hold the majority of your crypto wealth in crypto money. Specifically crypto commodity money. Today that means ETH and BTC.

Wealth is different than money. And crypto wealth should be in crypto money. Like yes, we get it, assets get tokenized. Crypto folks are wild for tokens. But that’s more of a DeFi problem. Financialization has allowed us to buy so many cool kinds of financial products that we forget that shit like derivatives were invented by normal dudes who traded soybeans for a living in the 70s.

But we needed soybeans to be traded first. There is an order of operations to setting up an economy. That means a system where folks grow soybeans and sell them, or turn them into another product like oil, or sell their labor as an accountant to the oil company that buys the soybeans. Because we don’t trade soybeans for steak. We trade it for dollars and then we buy a steak to enjoy at home with our spouse and kids. Circle of life! Circle of trade.

So first things first (I’m the realist) we to understand that understand that currency is crucial to the functioning of but also the first step in an economy expanding. We need to read up a bit on the history of money. PBS has a NOVA series that is pretty comprehensive. If you like stories Thomas Levenson’s Money for Nothing is a not-actually-tall tale about how the scientific revolution lead to a financial revolution (plus it has boats). Or learn how Kublai Khan invented paper money which seemed even crazier than a digital currency at the time.

If we start with a digital currency who knows what we can build from there. Balaji believes (and I agree) that it’s the first step in forming a digital country. But money comes first.

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Finance Startups

Day 152 and Running The Play

I’m going to put $5,000 into liquidity mining and yield farming to fuck around and, hopefully, find out.

If the last year has been about laying out the primitives of decentralized finance, this summer is going to be the Layer 2 land grab and I need to learn how to stake some claims. I don’t have a clue if it is going to work but I need to start learning how to play the game by tossing the ball around. I doubt I’m going to be whatever the equivalent of a professional player but I want to learn some muscle memory. You can’t very well buy an NFL team without having ever handled a football can you? Yes I am torturing a metaphor.

On a personal psychological note, I wanted to start with a $1,000 but then I realized the difference between losing $1,000 and $5,000 isn’t material to me (which blows my mind but such is the compounded benefit of my various privileges). However, the difference between 10xing $1,000 to $10,000 and 10xing $5,000 to $50,000 is extremely material to me. $50,000 is a a material seed stage check for a company that I may want to place a long bet on.

That is roughly the cost of my medical care for an entire year (not including drugs which roughly doubles it). That is a down payment on a parcel of land to develop over the coming decades. This is a moment to learn and leverage for the benefit of my future self and family if shit goes well. And if it doesn’t no big deal. The real money is better managed than me deciding I want to toss around a ball

My Chaos thesis says it’s time to run the play on the future more generally. It’s hard to argue that I can make good puts on a chaotic future without fully experiencing some of it myself in visceral fashion. I fully expect to lose all of it trying to liquidity mine and yield farm on my own but if I don’t well then I’ve proved something to myself about the future of capital.

I need to remind myself that this isn’t representative of how I allocate capital in a diversified portfolio to preserve my future security nor is it how I’d allocate capital even in a seed stage private venture stage portfolio. But it is a worthwhile amount to put on a 100% risk basis to learn how the fuck the future of capital allocation might work.

Honestly $5,000 is a pretty cheap tuition for a fancy credentialed college class so this seems like a good deal. I will write my way through the learnings and call it an independent study.

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Finance Internet Culture Startups

Day 151 and The New Capital Networks

A lack of network has generally meant capital constraints if you were an entrepreneur. Being hooked up with capital allocators was crucial to being a good operator. Access tended to compound over time like interest. Which is why we make “funny because it’s true” jokes about how successful founders usually had a head start in a few areas. I’m not saying that is going away, but decentralized finance is fucking with some of the consensus knowledge around how capital gets raised and deployed.

And what convinced me we are moving towards an inflection point, over the next decade, where capital allocators and operators decouple, wasn’t my tony Silicon Valley network. No, I’ve had access to the minds of those players for years. What clicked my mind into a position to take action? I spent an hour and a half getting a tutorial from one of my anon reply crypto friends on yield farming and liquidity mining. I don’t want to blow up their spot but Alpha Ketchum dropped a lot of knowledge on me today. And it shifted my energy from belief into understanding. From there action will be seen in my investments.

I’m still chewing through a lot of the details but I’m going to make a bet that scaling DeFi is going to require significant institutional capital and the support of experienced operators to realize its full potential. Thats why I’m invested in folks like Cambrian and Martin Green and would love to get my dollars into Arca and David Nage. That’s why, of my four thesis areas I’m pursuing in my own fund Chaotic Capital, two are explicitly dedicated to both organizational and systemic flexibility and how it plays out across new business opportunities.

We’ve seen capital decoupling from traditional centralized authority systems and trust based networks. The perpetual fundraising machine of tokens, coins and market making techniques like yield farming, are funding everything from esoteric art projects and to the next generation of insurance. Thing about that, the innovative companies that drive growth won’t have their capital needs met just on Wall Street or Sand Hill Road. If you don’t believe me look at what has already been built

Exchanges → SushiSwap, Uniswap, Bancor, 

Insurance → NexusMutual, Cover

Derivatives → Perp Protocol, Opyn,

Credit Markets → Aave, Compound, Maker

Middleware → Chainlink, Grt, 

Asset Management → Enzyme, Yearn Finance

Aggregators → 1inch and Matcha 

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Aesthetics Finance Internet Culture

Day 150 and Hypersigils

In the beginning there was the word……or the command line. Naming a thing used to be the literal path to power. Now we are pretty meh about the whole thing. Ritual magic is kind of a satanic panic middle brow thing in America even though we have a history of throwing in with prosperity theology. We’ve got entire evangelical communities dedicated to naming and belief with the expectation it will generate wealth and manifest prosperity. The meme magic folks who wished Trump into office were really just regurgitating Norman Vincent Peale prayers. Plenty of folks like to blame this kind of magic on like Max Weber with his Protestant Work Ethic but I’m mixed on it as I don’t think he envisioned Pentecostals when he said hard work was a moral good.

A friend of mine who knows my interest in both capitalism and its underlying energy in culture suggested I watch an old talk from illustrator and comic book author Grant Morrison.

Honestly you should pop it out and watch the whole thing if you have any interest in creation. But especially if you are interested in chaos. He discusses a term he coined called a Hyper Sigil. He is building on contemporary chaos magic which isn’t too far off from manifestation theology. He contends that bodies of art but really any form of creative work can be turned into collective signs of meaning with willpower and force. He literally means they are magic and if this interests you go read Ray Sherwin and Peter J Carroll. If that doesn’t no biggie the following point still stands. We have sigils in America that are pretty literally manifestations of power.

Corporate sigils are super-breeders. They attack unbranded imaginative space. They invade Red Square, they infest the cranky streets of Tibet, they etch themselves into hairstyles. They breed across clothing, turning people into advertising hoardings… The logo or brand, like any sigil, is a condensation, a compressed, symbolic summoning up of the world of desire which the corporation intends to represent… Walt Disney died long ago but his sigil, that familiar, cartoonish signature, persists, carrying its own vast weight of meanings, associations, nostalgia and significance.

I’ve completely fallen down a Grant Morrison hole as this kind of thinking is crucial to work in attention economy trades like communications, public relations and marketing. But I’m frankly a lot more interested in the practical aspects of how he conceives of himself as a chaos magician and how he we can all affect the reality around us. I’ve purchased his Invisibles comic. When he says imagination is the fifth dimension he literally means it. Multiversity is rad.

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Finance Startups

Day 149 and Optimizing for Outcome

I came across a thread today by Sahil Bloom on human goal setting and the mental models we manipulate. He introduced me to Goodhart’s Law

When a measure becomes a target, it ceases to be a good measure. If a measure of performance becomes a stated goal, humans tend to optimize for it, regardless of any associated consequences. The measure loses its value as a measure! Goodhart’s Law is states “Any observed statistical regularity will tend to collapse once pressure is placed upon it for control purposes.” But the concept was popularized by anthropologist Marilyn Strathern. She generalized the thinking and called it Goodhart’s Law. “When a measure becomes a target, it ceases to be a good measure.”

I am fascinated by this tendency humans have of fixating on the things we think symbolize progress instead of the actual outcome. Sahil names a number of instances in which this has led to bad business outcomes. CEOs managing to short-term stock goals has been one that has long frustrated me.

Startup land is immune from this tendency either. I’ve seen product teams fixate on OKRs such that they never miss a single metric but fail to launch their product on time. Or a venture capitalist will toss out something like an ARR goal for a Series A only to have a founder chase that number for a year and still not get funded when they hit it. We think these goals are the goals in and of themselves. But really launching the product on time and closing the series A are the only thing that matters. As long as we hit our goals who cares what metrics we used?

This is of course set against the classic “what gets measured get managed” which is an apocryphal quote from business theorist Peter Drucker. It may in fact be total bullshit. It may be that measurement actually hinders management. Said rather well by Simon Caulkin

Measures set up incentives that drive people’s behaviour. And woe to the organisation when that behaviour is at odds with its purpose.

Lest you worry this is just a business problem when I was single in my twenties I made a spreadsheet of the various gentlemen I was dating. I felt like I needed a way to make the process more efficient so I starting weighting categories of characteristics that was most important to me. I like intelligent men so I started listing their college degrees. I liked men who were into quantitative thinking so I started noting if they worked in banking or academics. And well you can imagine how this took a turn for the worst. Instead of meeting smart men that likes to look at the world through numbers I met a lot of bankers that went to Harvard. I was optimizing for the wrong outcome.

Next time someone tells you that some metrics or goal is the only thing that matters stop and question if it makes sense for the long term objectives. I’m not saying bankers from Harvard aren’t smart but I’m also not saying that all smart men are bankers from Harvard. And that turns out to be a pretty crucial difference.

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Finance Startups

Day 146 and Gossip

Gossip drive the world. The stories we tell about other people reflect a lot. Even if we claim we don’t care what others think what others think moves the world around us. And I would posit that this actually isn’t a bad thing. It can drive closer bonds and increased connection.

There is a concept in evolutionary psychology called indirect reciprocity. Natural selection favors strategies that base the decision to help on the reputation of the recipient. Social interactions in which one actor helps another and is then benefited by a third party are key to cooperative reputations.

This isn’t just a systemic population level issue either. People who are more helpful are more likely to receive help. It’s uneven obviously and people can obscure their reputation. Depending on if you are up or downstream of helping or being helped, you make different calculations. Some people help more but they feel it’s worth the cost. They are downstream. Others accept more help because they are upstream. We are all making trades based on our position and arguably they are fair market trades.

How we decide to cooperate and with whom is driven considerably by reputations and shared value beliefs. Relaying reputation signals to bolster your capacity to connect to others is actually a key part of empathy. We need to establish psychological safety to partner with each other. Gossip helps us find suitable relationships. This is especially true in disciplines which require creativity. Quoting myself on the topic of psychological safety in venture capital.

If entrepreneurs are solving entirely new problems with high chances of failure feeling like they can trust their financial partners should be a top priority. Yet the atmosphere of distrust is pervasive. Venture capitalist and entrepreneur are constantly managing the information flow between each other.

Managing the information flow is a key component of gossip. Showing you understand their context, their fears and their reputations concerns helps you. An act we denigrate in popular culture actually helps you to deepen the relationships as each signifier breaks down space between two people and builds trust. So don’t knock gossip. It has evolutionary, societal and individual benefit. Just remember the ultimate outcome is about bringing people closer.

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Finance

Day 145 and HODL

If I like something I want to commit. I don’t get folks who get panicked at bumps in the road. Hype cycles for cryptocurrency trading have been unappealing to me. I’ve never been one to watch things like FOREX trades so why would I want to do it but with Bitcoin? Like I have fantasies about being a trader but I am absolutely not. If I believe in an opportunity I am not a short term thinker or investor. I want to see where it goes.

The real excitement to me in crypto is the potential to impact larger more broad based systems. Changes that occur over time and with significant collaboration are more interesting than any narrative blip. A libertarian monetary policy implications was obviously particularly exciting. As business person the potential to change the middle man fee structure that makes financialization and banking a scourge was equally appealing. As a technologist the possibility of building applications on an entire new protocol is enticing.

The bigger picture is the only thing that matters. Go in the right direction over time and ignore the noise. That’s why we’ve slowly moved up our allocation into Bitcoin over the years. And that’s why I’m excited for my husband Alex to be working as the new COO for Hiro.

Any angle you take on the big picture implications for building new systems is an opportunity for innovation and wealth creation. That’s why I’m HODL. HODL is a mindset. Sure it came out of a misspelling of “hold” when someone was drunk but who can’t relate to the desire to really commit to a bigger vision? Participation in the creation of something bigger is the ultimate HODL value. Hold on for dear life or just hold on. Either way you are in for the long haul.

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Finance Politics

Day 141 and Double Indignity

I’ve always been interested macroeconomics. Even as a child I got very excited about trading and markets eating up movies & books with political themes. Precocious snot that I was I quoted the Economist in my high school year book. So was primed to be interested in Bitcoin from the start. I even had a physical copy of the ur-conspiracy theory of monetary policy “Creature from Jekyll Island” in college. Yes it’s embarrassing. Point being if you are a fiat freak you probably have some opinions about the Fed, a few of which sound utterly wild.

I’d been exposed to questions about money and what drives people to build and create. I was skeptical that we could continue printing currency because I was introduced to economics through the basics. I also had an intuition that this system was making bigger winners of the already advantaged and short term interests, while taking away from long term interests who need their time & money maintain its value on the horizon. Basically I think inflammation sucks for the young. And if you are young and poor it’s a double indignity.

This is why I find Bitcoin so appealing philosophically. The idea that those already in power can inflate their interests over those who come after them offends me. Dynastic societies become ossified. I found Steven Ross’s Stone Ridge investor letter to be a particularly compelling argument for why Bitcoin is a moral good for equity.

Money is, and has always been, technology. Specifically, money is technology for making our wealth today available for consumption tomorrow. Modern Americans with a ‘What’s water?’ mindset about money – virtually all of us – assume there is a sharp line of distinction between what is money and what is not. That’s false. Instead, throughout history, various monies (note: plural) have always existed1 – simultaneously – along a continuum of soundness, subject to competitive monetary network effects. Sound money – along with language – were the first, and have forever been the most important, human networks responsible for human flourishing. Imagine life without them.

I think Americans especially the monied elite interests are simply becoming too entrenched to the detriment of freedom here but most critically around the works. We have no incentive to let the rest of the world compete so we are rigging the game in our favor. I don’t like it morally even if it benefits me personally (though arguably not as much as it does Boomers and the old). I’d rather Earth compete as one as this drives our progress. Anything less is serving a double indignity to the least privileged among us.