Category: Finance

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Finance Startups

Day 270 and The Circle of Capital

Capital has evolved a lot in my life. The dynamics have changed so much in the 30 years I’ve been ambiently around venture it’s barely the same business. And yes I mean since I was a kid. The apocryphal family history is that I was born on the poor side of Silicon Valley while my unemployed father was working on pitch deck for education software. Yeah it’s a shitty origin story but it’s mine.

Back then you sold your entire life to some dudes for half a million bucks and gave up a lot of control. It wasn’t really collaborative but it was worth it to create the future. Back then your VCs controlled a lot more than they do now for capital they deployed. Flexibility and collaboration wasn’t really considered necessary. Your VCs actually controlled when you got fired (another childhood memory was a “take your daughter to work day” where a CEO got fired), when you could raise again, if and when you could sell your company, and honestly I wouldn’t be shocked if they had some Rumplestiltskin provisions too. That’s just where the market was at the time.

As it has become clear that non-linear returns come from creative founders and new markets, the structures of capital deployment have changed a lot. Capital cares about helping operators create because creation simply has more value than it did in the past. Venture capital isn’t old dudes optimizing for control and margin anymore (even if sometimes that might be a good idea) because that’s just not what makes money anymore.

Heck it has changed a lot in just half a decade. The last time I raised venture for my own startup, we actually priced the round (no uncapped SAFEs), we had a board from day one, and we were allowed to overshoot our valuation and capital goals by a whopping 300K. I was sure we’d reached the height of founder leverage at the time. Heck I felt certain we’d raised a small fortune on favorable & flexible terms. Six years later that would be considered a charmingly small pre-seed round with very onerous terms. Time marches on! And rightly so. Markets adapt to the needs of the participants and the returns they deliver. If it wasn’t profitable it wouldn’t be so.

This is all a long winded way of saying that I am continuing the circle of life. I’ve got my own venture fund Chaotic Capital with Alex Miller and Jacob Brody. It doesn’t look anything like the funds of my childhood or even the seed stage funds of the last decade. Probably because we as founders and operators lived through the hard lessons of venture in multiple cycles and took a lot of lessons with us. Capital isn’t about control. It’s about collaboration now. Capital starts early. Capital is flexible to generate returns But we also aren’t n00bs.

Rather than spend a year raising in silence and announcing it once it’s all said and done we are building a rolling fund. That structure works for us and my general affinity for building in public. It signals founders we are building like them (even as our other constituents see it as being responsive to the demands of the market). The rolling fund is a kind of flexibility to build at the speed of the market while also understanding that the give and take of responsible deployment must also work at the pace of founders.

While we work on forming our proper fund, we’ve created an AngelList Syndicate for chaotic where we’ll be creating SPVs for our current deals (we already have our first two which feels crazy to me) as well as follow-on deals once the fund is created. If you’re an accredited investor and interested in joining our deals, head on over. Isn’t it cool how these structures morph and change over time? I guess having a couple decades of being an operator has some benefits. You’ve seen what works and hopefully have some capacity to change what needs to be changed.

Our LPs and co-investors are mostly our friends and former colleagues who have spent years working with us at companies as varied and diverse as Stack Overflow, Trello, Easypost, Triplelift, Goop, PopSugar and over 40 different angel investments. Alex Miller, Jacob Brody and I have invested over 4m over the years which seems sort of astonishing.

While we work on forming our proper fund, we’ve created an AngelList Syndicate for chaotic where we’ll be creating SPVs for our current deals (we already have our first two!) as well as follow-on deals once the fund is created. If you’re an accredited investor and interested in joining our deals, head on over.

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Finance Startups

Day 255 and Bias Towards Fuckround

There is a tendency to believe that startups have a bias against older people. While ageism is alive and well, I’d argue what appears to be a bias against older teams is actually a bias against teams with experience. No one wants to invest in a team who don’t fuck around. We want teams that will find out.

One of the reasons I work with early stage startups is because their trajectory is not yet set. Every conversation has a hint of “fuck around and find out” because your vision is far away. You need to experiment, test, throw spaghetti against the wall. Pick your metaphor. The bias towards action and the bias for momentum exist in investor minds because the alternative is death.

This has the second order effect of selecting against teams with experience. It isn’t ageism. It is a bias against a certain kind of professional that knows too much. It’s not that anyone thinks experience is bad. It’s harder to fund teams with no exposure to the industry they are working in. It means that some types of experience will function as negative signaling. We think you know too much to solve the big problems. We are afraid you aren’t flexible enough to do the work of throwing out all existing assumptions.

While being an expert in a field means you have a better sense of how you will get from point A to B, it also means you have a less flexible mindset. You have seen what hasn’t worked. You have opinions about can or cannot be done. Even worse, you have an idea of how things must be done. Simply put a certain kind of battle tested, “expert in their field” persona isn’t trusted to fuck around enough.

If you are one of these founders, you have to fight against this signaling issue. Show investors your commitment to fucking around and finding out. Telegraph that all your experience and knowledge from your past work could very well be bullshit. Show us you will be committed to testing even more rigorously every hypothesis of how your roadmap will unfold. Then your experience becomes an asset.

We will trust that you have more opportunities to fuck around and find out than a less experienced founder because you plan to test what you think you know. Which is a lot! Show that no truism of your space will be held sacred. While a neophyte team will need to discover all the truths of a space to even begin to test. you will be ahead of them running test after test. Jujitsu that shit. Use the energy of your experience to show that you will bring the maximum amount of flexibility to finding new outcomes. The unbiased but experienced mind has the best chance at achieving momentum.

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Finance Startups

238 and DAO Ethics

Are smart contracts freeing us from the tyranny of the legal class just to toss us into the maws of the developer class? Sure we think of lawyers as being inherently worse because they are bourgeois and protected by credentialism and regulatory capture.

But as crypto gets more complex and smart contracts involve more intricate provisioning ,will it become just as exclusionary as the ecosystem of white shoe magic circle legalese? It’s getting to be mighty hard to afford Solidity developers!

Sure we tend to think of developers as friendly self trained indie types. Anyone can learn to code! Let us not lean on heavily on the benefits of decentralization as a panacea for human nature. Power aggregates and money likes influence.

When describing the benefits of how DAOs will outflank traditional corporate governance structures we need to look out for how we avoid the self interest of a protected class of Mandarins forming. We need to think ahead on how to keep smart contracts legible. I don’t have any of the answers here. Governance is just barely coalescing in crypto but it’s never to soon to think ahead.

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Emotional Work Finance

Day 233 and 927 Hours of Therapy

I’m motivated by media. If I’m in a bad headspace I can take time to read a book or watch a tv and shake myself out of it with a few hours. I’m a voracious consumer of all forms of narrative, it’s how I synthesize.

You’d have to be a professional to keep track of more stories than I do just by sheer numbers alone. Maybe journalists, authors or publicists read more than me, but even then I’d bet real money I’m still top decile. I never lose a “Wait Wait Don’t Tell Me” news quiz.

I’m working though some emotions on risk, punishment, hurt, and fear this week. So I’ve been watching a favorite show on all those emotions: Billions. It’s a show about a hedge fund manager feuding with the US Attorney for the Southern District. It’s a terrific portrayal of finance culture and elite consumption. But it’s real strength is it’s portrayal of therapy. Emotional capacity is the key to coming out ahead in Billions.

While I don’t want to give any spoilers, the second season gives us a character named Taylor who is a prodigy. Not only are they intellectually brilliant but they understand who they are. I’m rewatching the show so I’m noticing details I didn’t process the first go around. Taylor says they have had 927 hours of therapy.

The impression I had on the show was that Taylor was in their twenties as they frame the introduction of the character around an internship and graduate school. I wish I had started on therapy in my twenties. Imagine having over three years of intensive emotional work before you’ve started your career. Honestly I’m envious. When I was in my early twenties I didn’t understand jack shit about my emotions.

Maybe by the time I get 927 hours of therapy I’ll recognize my own traumas and motivations as well as Taylor. I’m getting up there in hours and I am admittedly sinking a lot more into understanding what motivates me now than I ever did when younger. It’s not exactly linear progress. Feelings aren’t facts. That makes it a lot harder to lock down what will or won’t work for you. But I’d rather be finding out who I am now. Some people never do. But still I wish I’d had the good sense to invest 927 hours into therapy when I was Taylor’s age.

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Finance

Day 225 & Explaining DAOs to Moms

My mother is a sharp woman. She’s interested in economics but if you asked her to explain securities law she’d probably shrug. Not her expertise. She did survive our family bankruptcy during the tech IPO implosion she’s got a slight intuition of securities law in the context of consumer protection but that’s about it.

So I was impressed that she was able to sum up the recent infrastructure bill’s attempt to make crypto foot the bill very neatly.

“So they are trying to convince us that people who program computers to run math problems are actually bankers?”

That’s…actually not too far off. She seemed to grok that this was a misunderstanding of the basic technology, who builds it and it’s purpose. She was glad the amendment didn’t pass. Clearly people who build computer applications are not the same as the guy at Charles Schwab who looks after her retirement account.

We were discussing it, as I was trying to explaining PR DAO and why I wanted to help organize an activist group of folks whose purpose was execute public relations campaigns to tell stories about crypto. I explained to her that rather than having a bunch of executives who make decisions we would write a set of rules that automatically determine how we make decisions. Those rules would let all members of the organization vote on how we wanted to deploy our assets and pursue our agenda. She liked the tag line “rules not rulers” a lot. She’s pretty into freedom. A smart contract was pretty intuitive to my mom.

Where she got confused was the governance tokens. Not how they worked. Again it was intuitive to her that depending on what you contributed and how invested you were in the organization that you would a different say in what got done. Maybe each token represents one vote. Maybe some people have more votes because they are more invested. Presumably we figure that out in our smart contract. What she didn’t get was why the government thinks a voting mechanism is a security.

“So the government treats the way your group organizes decision making as if those little voting symbols were stock in IBM? That’s fucking stupid”

Now granted my mother probably can’t explain what a security is (she’s got the basic idea that they are like a type of money and Boomers like to own stocks). She gets why they are regulated the way they are in a general sense. She’s lost money on badly governed companies. So sure it’s fine that the government has some rules for that sort of thing.

But even to a lay person like my mom it seems pretty clear that something meant to represent ownership in a money making enterprise and something meant to help organize voting and decision making are separate ideas. She seemed to think maybe they ought to distinguish between the two ideas. Because you know the last time we came up with clever ideas like the corporation the whole world changed. Evolving them again to be autonomous could make for the same level of change. If my mom got that in a half an hour phone call seems like maybe the professionals at the SEC could work it out too.

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Finance Internet Culture

Day 220 and Crypto’s Publicist Part 2

Yesterday I wrote about my proposal to create an activist DAO to engage in public relations for crypto. The goal of the organization would be to create a groundswell of support for the space, it’s values, and opportunities as well as engaging in support for a more positive regulatory environment.

If you would like to hear more about why I think it is time for the wider decentralized crypto community to engage in a public relations and media campaign please see my post yesterday. Today I am putting down further notes on what I think our values and priorities might be. As always, this blog is a work in progress so consider this my thoughts as of now that are open to being edited and changed.

What kind of values are crucial in a PR or communication DAO or interest group?

  • Open
  • Participatory
  • Trustless

It’s important that whatever we do on behalf of crypt it must be done in the spirit of the space and why so many disparate types of people believe in its values. While there may be structures like executive teams, core teams, board members and studios and contractors to execute on our mission we want to use the tools and transparency of crypto.

But to what purpose are we organizing? We will create content and engage in conversations to shape media narratives and public sentiment aimed at promoting the positive elements, potential, and impact of crypto.

How will we do this? We will hire publicists to promote our stories in mainstream media along with commissioning content meme-ers and creators to share opinions. We will engage with spokespersons to share talking points created from the priorities of the community. We will place our content, from memes to editorials, on our own properties as well as in supporting communities and member publications.

I expect I’ll be doing quite a bit more note taking and research. If you want to be a part of this effort I’ve started a shared Google doc for collaboration. Email me Julie @ chaotic dot capital or DM me @ AlmostMedia. This won’t be built in a day but together we can push it forward.

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Finance Internet Culture Media Politics

Day 219 and Crypto’s Publicist

Most industries have interest groups. Publicists, lobbyists, and spokespeople weave together stories, talking points and preferred legislative agendas. Anyone or any group is free to discuss why their preferred business or issue is worthwhile and convince others of their view. We have a marketplace of ideas. Sure, not all interests are good but anyone is free to promote what they believe in. So why aren’t we doing anything for our cause in the crypto community? I say it’s time crypto had a publicist.

Not every country allows for this. The crypto community has an obligation to recognize that when we fight for our own interests it isn’t just we who benefit. The entire world benefits from open, decentralized and permission-less systems. What we do benefits everyone who wants to live in a freer world. It’s time crypto had our own activist DAO to protect and promote our values.

I am proposing the formation of an activist DAO promoting the use of crypto. Our goal is to advocate for positive popular culture narratives about crypto. We vote on our issues, stories and key initiatives through the DAO’s native governance tokens. The DAO will hire publicists and communication professionals to promote our stories in mainstream media along with commissioning content meme-ers and creators to share opinions. Policy is crucial but public perception is faster and pushes the right policy down the right.

As place holder I’ve purchased CryptoCommsCoalition.org. The Crypto Communication Coalition. I am working on a shared collaboration doc in Google Sheets to collect input, feedback, and priorities. Anyone who is interested can participate in our effort. Email me Julie @ crypto comms coalition dot org or DM me on Twitter.

We need DAO creation specialists, legal experts, memers, streamers, Reddidters, governance folks, publicists, lobbyists, fundraisers and a thousand other specialists I haven’t thought of yet. This won’t be easy but it’s an eating our own dog food moment for crypto. We can use our own tools to advocate in a participatory, transparent and open way for our own interests. If banking and big oil can can afford publicists then so can we. gmi.

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Finance Startups

Day 216 and Annihilation

My parents were hippies. Thanks in particular to my mother’s great interest in the spiritual world, I spent time in ashrams, communes and retreats as a kid. One was a great big sprawling former summer camp in the Catskills. I adored spending time there.

There is something amusing about being in a Christian family who has decided to study Kashmir Shivaism in an old Borscht Belt resort. But it was thanks to these adventures in expanding our minds and spiritual horizons that I learned about Shiva the Destroyer. And Shiva has had a profound impact on how I think about startups.

I won’t get into the full theology of Shiva but he creates, protects and transforms the universe. His power is set against the goddess Shakti (sorry Parvati can’t get into your whole deal) for a kind of death and creation in one balanced whole. To this day, I chant Shiva’s mantra “Om Namah Shivaya” when I mediate. It more broadly has a meaning of the “universal consciousness is one” which I tend to interpret as ego death. Shiva is the destroyer of my ego for which I am grateful.

The idea that creation and destruction were interlinked, and indeed matched, spoke to me as a child. Some kind of pre-rational understanding of the first law of thermodynamics. Energy is neither created nor destroyed. Maybe Shiva and Shakti are just godhead metaphors for the eternal spiral of creation and destruction that we’ve come to dimly understand thanks to the study of physics. I’m neither a theologian nor a physicist.

But I am a business person. Shiva lead me to appreciate the economist Joseph Schumpeter. You see, metaphysics aside, I took the lesson that destruction wasn’t inherently bad quite to my heart. That sometimes, for new things to be formed in the world, old manifestations needed to be destroyed or transformed. Schumpeter’s gale or, more commonly, creative destruction, held my imagination.

I thought to myself “dismal science my ass!” Economics has dedicated an entire discipline to the study of apocalypses and the utopia’s that are created in their wake and we call it good business management. Wealth by way of eschatology. Obviously I was hooked.

According to Schumpeter, the “gale of creative destruction” describes the “process of industrial mutation that continuously revolutionizes the economic structure from within, incessantly destroying the old one, incessantly creating a new one”

Startups are known for their creative destruction. Small changes and innovations slowly, and then all at once, implode and destroy old ways of doing business. if we are lucky more wealth is created in the process. Sometimes enough to change entire cultures and people for the better. And sometimes not. But if there was ever going to be a god of startups I think it would be Shiva.

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Finance Startups

Day 202 and Show Me Anything

I’m lucky to see work from founders at the very earliest stages. If you have a problem you are solving for chaotic world I’m generally interested in seeing it even if it’s just in the idea phase. But you have to show me you’ve got a plan to build a product. Any product is fine. Just show me something! Show me how you have the capacity to build even if you suck at it.

Bobby Goodlatte captured some of the sentiment I feel on the subject well with this exasperated Tweet.

What’s a “builder”? Show me something. Anything. Just show me one pixel you’ve created. That’s what a builder is. That’s why PM’s don’t qualify.

Sometimes it can feel hard to build something, anything, when you are very experienced. This is a problem I’ve seen across all kinds of impressive people. Academics, government folks and higher end finance folks, former c-suite executives. They know what good looks like so anything they can physically make with their own two hands will all look like crap.

I’d even go so far as to suggest there is an inverse relationship between how much you obfuscate your lack of existing product and your credentials. There are other corollaries on that basic theme. How comprehensible your product is right now is inversely related to how extensive your service layer is at the moment.

I see a lot of brilliant, extremely credentialed people solving big problems, but because making money is important they will pitch what amount to service companies without an existing product. But they will use extensive jargon and hand waving visionary opportunities to hide the fact that there isn’t any product layer yet. Which is weird because like eventually I’ll find out right? You wouldn’t want to trick your investors on the state of play.

I’d encourage you to stop trying to hide that fact. Don’t be embarrassed that you can’t make things to your standards. None of us can. New things always look like shit. Just own up to that reality and you will find more help from folks who will want to help make it better. Stop showing me CAGR and TAM and possibilities as a way of hiding that you haven’t built a product yet. It’s ok. You don’t need to have built something great yet.

Admit it. Show me some wireframes and a roadmap. I’ll take that way more seriously. In fact, I’ll probably overweight you showing me exactly what you do have and how you plan to use funds to improve it. That’s how much startup people value just building the damn thing.

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Finance Startups

Day 181 and Thesis Trends

As I was putting down scratch notes for Chaotic.Capital’s thesis yesterday on the types of businesses we like I thought I’d do a bit more stream of consciousness writing to discuss some of the mega-trends that I see driving returns over the next decade.

Embedded Functionality

We think more and more businesses will be born of the embedded functionality inside protocol layers or data sets. Many protocols have functionality embedded across different layers of utility and functionality. For instance, the new consumer bank is an API at heart. The protocol layer is the API and the embedded functionality is the financial services layers enabled through the protocol or application layer. Need another example. Retail sales data and demand trends give rise to fashion retailers. Think of StitchFix, the clothing brand is the embedded functionality of its aggregate trend, recommendation and demand data set.


Unbundling Trust

Trust based networks rule businesses like insurance, retail banking, law and financing. But what if trust was unbundled from institutional nexuses of power. What if we built trust from value creation instead of value extraction. DeFi wants to build permission-less trust based on a protocol. Its entirely possible we bundle trust back into the wisdom of crowds and markets. Wall Street Bets is an aggregate source of unbundled trust. Figuring out what layers can be stripped away for more efficiency and what layers we need for safety and peace of mind are unsolved problems.


Data Ingestion Is Value Creation. The more capacity we have for data collection the more demand we will have for data ingestion and processing. While we can say sure businesses rely on the protocol and data and that unbundles trust, that’s not the full picture. We will need people who make sense of the chaos for the muggles. Ordered systems give the impression of serendipity for their users (an introduction on a social network, a recommendation for a loan, an outfit customized for you) but the work required to intake and order the data to create value for users is a big hairy problem. And there is a lot money to be made in those. Centralization may come at this layer especially in user experience.

Flexible Asset Weighting.

We are also interested in businesses that know where they stand with capital needs for their business. If you are executional business you need a thin layer of assets to succeed. To quote Roy Bahat “hot swap” startups are executional businesses. A slim horizontal physical layer to take advantage of low financing costs means return on equity is greater for these asset light businesses. If it’s deep innovation then you can be asset heavy. We like those just fine too. But knowing where you stand and anchoring your business case on your asset weighting can give you an edge. That lets you be capabilities based and find opportunities, particularly as debt as is in a commoditization cycle.


All of this is to say we are thinking across a number of system level problems to unearth startups that will give flexibility to individuals, organizations, industries and hopefully the entire economy. Incumbents won’t see who is coming to beat them because they won’t recognize the new predators. They prioritize value systems that at won’t remain true as systemic chaos erodes inefficient businesses and institutions.