Category: Startups

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Internet Culture Startups

Day 1434 and Density

There is always a debate in startup life as to how the density of a given ecosystem impacts outcomes. A tight network of well connected communities and individuals helps founders, investors and talent connect.

Before the pandemic it was considered fairly normal to be within a major hub as the common knowledge was that “density” matters. You wanted to be in the action of a scene.

There are great startup cities. New York has an incredible scene. My hometown of Boulder has a great technical core. But as much as cities and companies compete over status the one with longevity is Silicon Valley. Heck it was a debate when that even encompassed San Francisco until Twitter moved in.

Then everyone spread to the four winds during the pandemic. I like to think of this as the era in which Silicon Valley got back to its digital roots. Being extremely online became a behavior that worked well for anyone if you communicated well with words. Being on the right coast was about being in the right online communities. The network state is online.

I’d say that was as pure a return to source culture as there ever was. Different people value signal across different networks and the open web of words has been home to software and hardware developers for generations.

The world that builds companies lives virtually as much as it does in the real world. We like to meet up but we also know it’s the tools that connects us that make the difference.

Every subculture that has emerged with a breakout hit did it through the digital commons we built together. I’ll always appreciate coming to the source culture to replenish but I know the density of the network is at its swiftest when our extremely online communities communicate.

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Politics Startups

Day 1430 and Realignment

American politics has become center of gravity for culture. I’m not thrilled about this as I have utopian high mindedness in my bones and that never pairs well with the real politic of a nation.

I felt being open to change was a part of my cultural upbringing as an American. Reagan Revolution babies enjoyed Clinton neoliberal growth. Optimism meant being interested in technology.

I have never been satisfied with reality because “we can do better” was both the regional culture of frontier Western civilization but America in particular.

We can imagine better which means we can do better. Somewhere between the neoconservatives forever wars, liberalism’s tolerance of intolerance and the growth of an expensive permanent state bureaucracy we lost some shine.

Losing our can-do spirit to fear and zero sum thinking led to strange institutional outcomes. Watching fear spread over years of pandemic and institutional failures did not help.

I’m not a novel voice in this discourse but most of the startup world and technologists in general had sincere affiliations with American institutional liberalism and even in particular the flavor of Democratic neoliberalism you might have associated with Bloomberg. The Obama administration certainly acted as if we were part of the coalition. The sincerity of that alliance is a question of course.

I don’t know where the realignment lands as we go forward but I hope as many people as possible sincerely embrace wanting more optimism.

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Startups Travel

Day 1424 and California Dreaming

We’ve just had a beautiful snowfall in Bozeman. If you are back up on the mountains at the edge of the valley you are enjoying a mystical winter wonderland.

Alas I am not long for cosplaying Frozen (blessed) as I am headed west. No, I am heading not to Seattle the most important city of the 90s. I am headed to Joan Dideon land. I’ll be in California.

I’ll be in Los Angeles for the week or so if you happen to be on the west side. I’ll then be headed up to San Francisco.

It will be a little whirlwind of family, friends and hopefully some useful business. I’ll be visiting start ups. Going to YC Demo day which I have not done in person. Meeting up with anyone who might want to be a node in our network.

I am game to meet up with folks working on weird shit and are looking to build it. I am also looking for LPs in our next fund so we can keep funding the weirdos who build things.

The virtuous cycle of techno capital starts long before an opportunity is clear. If you have something chaotic in your heart send me a DM

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Internet Culture Startups

Day 1421 and Culture Clashes

I sit in between half a dozen different community nodes thanks to my interests in open source software, decentralization, crypto, and autonomous systems technology.

This set of interest covers a lot of ground from ecosystem level collaboration in financial organizations like DAOs and to player versus AI agents coordination to peripheral control of drones and machinery.

Many different demographics are attracted to these frontiers for different reasons. Hackers have a very different mentality than mercenary technologists looking for maximum margin.

Open source has traditionally struggled more from a lack of financialization than from an obsession with it. Which seems less true in the crypto era than in previous more academic and defense oriented eras.

There are classic open source business models and anyone with age and experience in startups has some opinions which I leave as an exercise to the reader. They occasionally fail and an open core loses more than they’d like to professional services. I am writing on WordPress.

One strange aspect of what drives these frontier spaces to interact is that depending on how much leverage you find in building a network you may have different incentives than other builders and users. Expanding out to scaled use may drive a lot more value than the resources required. How the surplus gets divided is always contentious.

For some, the most crucial cultural goals is expanding access to automation and ripping away as many of the services and middle men as is feasible.

Decentralized systems make it harder for middle men to maintain monopolies. Thats its own goal for true believers. For others the goal massive financialization that drives network connectivity is the benefit. Self interest driving common goals is perfectly acceptable.

As I watch the current season of hyper self interested memecoin cryptomania engage with the academic utopian open source artificial intelligence community, I am reminded of so many of the classic issues we have in financing and sharing in the spoils of common infrastructure. Who benefits is a question we should all be asking more regularly

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Preparedness Startups

Day 1419 and Know A Guy

Running a startup, for all its supposed glamour, is mostly an exercise in learning how little you know.

Sure there are playbooks for some of what you will do. As the technology industry has grown and startups have become an appealing career choice we’ve filled out how-to guides for everything from fundraising to operations.

Alas all advice is specific to the giver’s experience and untangling biases to make advice relevant to your specific needs is quite hard. That’s where it helps to have more experienced operators on hand to call bullshit.

At chaotic.capital we pride ourselves on being investors who “have a guy” for even the most esoteric possible requests. Playbooks can only you so far when you need an expert.

Just in the last two days we’ve worked through how one hires a chief of staff, what to do when letting go of counsel who made a mistake, installing appropriate security procedures for digital footprints, and the resale brokers for a rare commodity.

We like to problem solve and the weirder the problem the more fun it can be. Removing obstacles and clearing bottlenecks is satisfying work. And knowing guy who knows a guy is a heck of a fun game of social geography.

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Politics Startups

Day 1413 and Much to Consider

It’s a nice number for today’s post. A strange countdown inside one day. A little spooky. Maybe also some good luck. Fourteen. Thirteen.

I am tabulating much more than my days of writing in a row or any particular numerical significance that this position of numerals might show. I’m adding up our position and deciding how to play our hand.

There is simply so much to consider. I feel it in my joints. Maybe that is evidence of acceleration. All I see and hear is speeding up. Are you accelerating anon? Maybe that’s the pressure in my joints and it’s arthritis at all.

I have felt a bit sick to my stomach and I’d prefer to blame it on delicate lady things. It could also be nausea from the spin cycle of all that “much to consider” of the moment.

I’m glad I’m ensconced in my winter farmhouse. The numbers go up. The game’s whirlwind spins. There is much to consider.

It really ruins your appetite this whirling. The ride up the rollercoaster. No wonder Alice in Wonderland commercialized into whirling teacups at Disneyland. Can’t have it be the symbolism of opinion and fuzzy opinions.

So there is much to consider as we whirl like dervishes into the next moment.

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Emotional Work Startups

Day 1398 and Overstimulated Nerds

Introverts don’t do well with social overstimulation. Any time I attend a gathering where the majority demographic is nerdy, weird, and autistic I find myself feeling the collective vibes of the overstimulated. And it’s not always good vibes for many of them.

I am doing everything I can to take care of myself, be kind to others and still be gently socializing. But it’s not easy.

I’m exhausted from the effort, even with my attempts to practice productive habits like nervous system exercises and getting adequate sleep. No amount of supplements can fend off a collective sense of fear.

I always notice what a rude demographic we introverts can be in these circumstances. Everyone is doing their best to be present and do delicate dances of parasociality where you know each other from the internet but do not wish to intrude or interrupt someone doing business.

In the cases where you are socializing with friends in real life and the rest of a group “knows of” but doesn’t know actually someone you find yourself surrounded by defensive social postures. Plus-ones with little contribute make it even worse.

And I’m not even going to touch the social dynamics of status. Insecurity seems to run rampant in all human groups, but nerds who have known social precariousness are the worst offenders in these situations.

Fear over one’s place within a group that has a wide variance in status can be intense. I don’t like seeing anyone feel left out. I like to be welcoming to everyone I encounter. Even when I’m an overstimulated introvert.

It’s especially important to me to be nice when it’s a group where the capital that provides status (social, literal) rises to celebrity or billionaire.

It can feel paralyzing to interact with anyone who has some degree of status if you don’t want to make someone uncomfortable. The awareness of social graces isn’t always enough.

It’s just as likely that someone will put on airs and over estimate their status as they are to offend the actually important guests.

I dislike watching people police their own social status but it’s even worse when someone polices the status of their friends. It creates cliques and ostracism in the best cases. Cutting off access can help when someone is just an overstimulated introvert but in practice makes the entire environment more fearful.

These social fears can really gum up the works when it’s nerds concerned over their own place within an event let alone in society.

I feel pity in the most awkward of cases but it’s really born of sadness. Cool is a bit like grace. We do little to deserve its bounty, grasping at it only shows our hubris and it doesn’t work in any case. I wonder if that’s a heretical opinion.

Categories
Internet Culture Startups

Day 1394 and Wiped

I’ve had a great year. I’m having a great month. I had a great week. I’m absolutely obsessed with my portfolio and the founders in it. Every new opportunity makes me feel better about the future.

And I’m so tired from processing all of that that it’s little wonder my body is grinding out hours of REM sleep a night.

I’m in the middle of a tight circle of artificial intelligence memetics thinkers which has been enthralling. Machine minds needing machine money has been such a pat truism that when a genuine breakthrough shows up it’s easy to focus on the wrong thing. It’s not about memecoins. I almost feel as if I’ve been preparing for this moment my entire life.

In the middle of this virtual drama I am trying to remain focused on human concerns. Repairing boots. Doing chores. Preparing for a gathering in Miami next week.

Somewhere in the middle of this work gets done, an election is will be decided and I’m just wiped.

Categories
Media Startups

Day 1381 and Radical Responsibility

I thought the discourse around “founder mode” had died down but Kim Scott the author of the best selling book Radical Candor decided to link the meme to what she considers a so-called rise of “neo-authoritarianism” in Silicon Valley culture in an op-ed in the New York Times. Naturally it’s about Trump too.

My read on her thesis is that she has decided to use a technique she disavows in her own work; the frame of the piece is manipulative insincerity. It’s an unclear criticism being used for political gain.

She works to convince the reader that actually the most libertarian and individualistic demographic, who regularly decries state power (especially its use of coercion to drive censorship, limit transactions and restrict compute), are in fact, actually vouching for totalitarianism.

Gift Link to New York Times “How Founder Mode Explains the Rise of Trump in Silicon Valley

Even the graphic hints at the supposed appreciation of neo-monarchy as a nod to nRX intellectual Curtis Yarvin.

I fear she firmly missed the point of founder mode for her insincere political framing. Despite her clear understanding of our values.

In that original recipe, venture capitalists invested in founders rebelling against established hierarchy and building great products. And when those rebels themselves became too hierarchical, venture capitalists turned to new founders aspiring to overtake the old order.

She is right about we prefer to work as an industry and how we see our efforts. “Many of Silicon Valley’s greatest products were originally intended to liberate, not to control people.”

And yet missed she missed that founder mode is about liberating our founding teams from the suffocation of professional management. It’s got nothing at all to do with justifying tyrannical founders.

Rather founder mode is about limiting the tyranny of managers who can stymie progress despite having little personal responsibility for the success of the firm. In another world, she might have written a sequel called Radical Responsibility about fixing this problem.

Larger firms have a pantheon of corporate departments to ensure smooth governance from legal, to HR, to corporate communications in order to comply with state expectations.

As regulations have ballooned so too have the specialties required by the middle managers. We must be in compliance. We must take everything and every view into account. We must do things by the book.

Founder mode isn’t about running ripshod over your people. It’s certainly not about Trumpian declarations of what must be done. She’s absolutely correct that “emotional dysregulation, bullying and bloviating are not leadership attributes”

I find her criticism to be manipulative insincerity. She’s deliberately missed the point of the original Paul Graham essay, inserted her own political insinuations about how Silicon Valley is hiding their true preferences for authoritarians while herself advocating for a pass the buck culture. It’s not fit for Radical Candor and I’d expect better from someone of her stature.

Categories
Finance Startups

Day 1376 and Q3 2024 Investor Update & Market Analysis for Chaotic Capital

Welcome to the Q3 2024 update for chaotic.capital LPs. I’m choosing to post a selection of our reporting publicly so prospective founders and LPs can see our thinking.

You may be invested in chaotic.capital because we invest in ideas that adapt humanity to our new chaotic era.

Enabling resilience in the face of unexpected & rapid change is our lodestar. It’s a simple heuristic that yields a complex thesis: that technology is a tool for increasing leverage. 

In addition to these investor letters, you can always visit jfredrickson.com, where I write every single day about whatever I’m thinking about. You are also welcome to DM me on Twitter @AlmostMedia or text me on Signal any time.

Q3 was another strong quarter for chaotic.capital. Our ability to identify and back founders early remains core to our success and we’re seeing it both with the inbound flow from founders (as seen in the two new deals we did this quarter) as well as the progress from our existing portfolio, with four new markups this quarter and substantial business progress on those and others.

The markets are increasingly focused on power and compute. What was once a contrarian focus on energy, infrastructure, crypto, and artificial intelligence has now become a core narrative among informed investors.

We believe the future of compute—particularly in relation to crypto and AI—will increasingly be viewed as a basic right, not a privilege, as these technologies scale to mass adoption. 

As governments grow more cautious about debt and monetary risk, individuals and organizations will turn to trustless systems to ensure secure transactions and autonomy.

This is why we focus our investments in the space on foundational layers that will power the next generation of applications.

With portfolio companies like Squads providing on-chain economy tooling, Kuzco reducing reliance on intermediaries while creating an open market, SFCompute pricing compute and creating spot markets, and Chroma becoming the go-to choice for open source vector databases, we see the intersection of crypto and AI creating secure, scalable systems for individuals and organizations alike.

Access to compute is quickly becoming synonymous with freedom of speech and, ultimately, the freedom to transact. 

These open trustless systems enable efficient transactions and verification, a crucial development as geopolitical multipolarity continues to rise, and more people need to ensure their interactions are secure without reliance on the state.

While Americans might not yet fully appreciate this, we’re seeing growing demand for these alternative systems and open models from those who are navigating increasing regulatory pressures and instability.

Europeans, whose governments are deploying strict limits on AI models are beginning to understand, those from countries facing geopolitical uncertainty (e.g., Israel, Ukraine), live it already, and those in countries with unreliable currencies and legal systems have been navigating anarcho-tyranny for decades.

But it can be precarious in the US as well, in California it was only the intervention of a veto from Gavin Newsom that prevented SB-1047 from restricting compute and hobbling the development of open source models.

Looking forward, this ability to access compute at scale may well parallel the right to transact. As nations confront their own risks, network state behaviors will become more prevalent, driven by the need for secure, decentralized systems that ensure autonomy in an increasingly unpredictable world.

We’re excited about the future of chaotic.capital and the opportunities ahead. As always, I’d love to talk about any of this with your discussions with you, so feel free to reach out. We’re just getting started, and there’s much more to come.