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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.

Categories
Community Emotional Work

Day 1428 and Thanksgiving

It’s nice to have a record of multiple years of thanks to look back upon. In 2023 I was thankful for the serenity of acceptance. In 2022 I was grateful for regaining optimism. In 2021 I was grateful for the small measure of health I’d gained.

In 2024 I’m still optimistic (albeit cautiously) as I have the similar amounts of health and acceptance keeping me above the waterline of our chaotic reality.

I am thankful the incredible amount of progress I’ve made in my work this year. We’ve done so well with our first fund at chaotic I have little fear that we will continue building it even as the markets remain a challenge.

I’m thankful for our founders who made it possible for me to make a go of investing in weirdos.

I’m thankful for my marriage. Alex and I have made it to our second decade together. I highly recommend marriage if you get the chance.

I’m grateful for so much this year that listing it out seems a bit overwhelming at 8pm at the end of the day.

But if you have the chance to be grateful in writing it’s worth doing. Looking backwards on your gratitude enables you to look forward with optimism.

Categories
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

Categories
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

Categories
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.

Categories
Aesthetics Culture

Day 1418 and Winter Wonderland

I’m in a terrific mood. Maybe it is just the hormones cycling up. Maybe the red lights we installed in the bedroom are actually improving my sleep quality. Maybe it’s getting a foot of powdery snow over the weekend.

So much of life seems to boil down to manage my own circadian rhythms even as I plug myself into the hiveminds of my favorite corners of the internet dutifully everyday. And my body likes short days, long nights and the bitter cold.

Certainly success is contributing to my buoyant mode. All of my founders are soaring (which seems statistically rather unlikely given the choppy markets) and the vibes are good. My chaotic.capital clique is thriving.

It’s getting to the point where I think we should host a portfolio dinner or something. Though that would be challenging as we are a distributed group. Alex realized recently that we only met one of our portfolio founders in person before we invested. Can you even imagine that in a pre-pandemic world? Our deal flow comes from the virtual worlds I live in daily.

Being snugly ensconced inside several areas of with macroeconomic tailwinds doesn’t hurt but most of those choices were made two or three years ago so I’m simply directionally correct, well connected, and unafraid to commit once I’ve satisfied my own process. Everyone has a long way to go but it feels wonderful to enjoy their success.

Walking in a winter wonderland.

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
Emotional Work

Day 1380 and Another Turn Around The Sun

Life has been on a wonderful trajectory for me over the last four years. The pandemic marked breaks in everyone’s lives and the chances we were afforded to shape our lives was a privilege in a disruptive and challenging time.

Others took similar leaps of faith into new ways of living. So as I celebrate my birthday today I feel such gratitude. I couldn’t ask for a better turn around the sun.

We had a life changing exit and a series of investments go our way, I made my way into inception & pre-seed investing with our pre-seed fund chaotic.capital, and we moved to Montana. It’s all amazing especially as it’s had its struggles with my health.

I am being offered a season of life where I feel like I can really contribute my skills in professional ways that could be impactful. Everything I’ve built towards and all of my interests and hobbies are tying together in amazing and exciting directions. A happy birthday to me for sure.

If you are in New York City I’ll be flying in this weekend for a week in the city. I’d love to meet founders, other investors, and startup folks in general. Also if any weird Dimes Square reactionaries want to meet up I offer parlay.

Categories
Aesthetics Startups

Day 1363 and Landfill Apps

Building good software is a topic on which many of my friends and colleagues have extremely strong opinions.

Anything built by humans can become a craft with skilled artisans and building software doesn’t escape this. While there are 27 million software developers in the world and 4.4 million of them are in American, if you pressed the startup community most would agree the number of good software developers is much lower.

I came of age in the blogging era, where we got writing like Joel on Software. I learned to build thanks to other builders sharing their craft and discussing it on forums & personal sites. I had access to the insights of builders like DHH and Alex Payne. Their commitment to publishing accessibility helped onboard millions of normies like me.

In some ways, startups and the software giants of FAANG are a victim of our own success. We onboarded the world to our efficiency.

And now with AI coding software (incidentally trained by Stack Overflow data & GitHub repositories built by my community) we are experiencing a Cambrian explosion level of coding access.

And it’s not Zapier hacks or snide remarks about Rust anymore. Anyone who can think critically about a product feature can build it with clear thinking and natural language.

I recommendIn The Beginning There Was The Command Line” by Neal Stephenson so often because every time we have an abstraction leap that allows more access we move further away from the power of craft.

And that is an unmitigated good in many ways as more people get the benefits of these tools.

But we are also going to get a slot of shit churned out because of that. Soychotic called them landfill apps when Marques Brownlee or MKBDH launched a $12 a month app for phone wallpapers. The app enraged Twitter.

If history is any indication the growth curve in app building is just getting started. Much awful nonsense will be built and sold, but imagine how it enables those with taste and opinions to make new solutions to our problems.

Ironic a critic of software like MKNDH should play such a role in reminding us of just how hard it is to make something good. Making money though can have a much lower bar.