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Emotional Work Startups

Day 1449 and Self Deception

Ten years ago when I was struggling in my role as CEO of a startup I’d cofounded, I was introduced to a classic business book called Leadership and Self Deception. I read it in one setting on an airplane. It was that good. Or I was that bad. Probably both.

The research explored how we end up creating and sustaining problems we don’t know we are causing, and how and why people resist helpful solutions. They discovered the clear and surprising way that people begin to evade responsibility without thinking that they are doing so, and therefore end up blaming others or circumstances they, themselves, are helping to create

It’s worth the read even if you are the type who prefers a synopsis. I believe most business books could have been a blog post personally. That’s how strongly I recommend the book.

Self aware leaders enable personal responsibility in themselves and their teams. And yet we all lie to ourselves in our personal and professional lives to evade taking responsibility for who we are and what we want.

It’s easier to evade responsibility. Things happen to us and we let others direct the course of our lives. This is not however a path to effective leadership and it’s a miserable way to become a victim of everyone and everything.

There are many frameworks for overcoming the self deception our ego generates. We are not doomed to self sabotage and evade seeing ourselves clearly.

Leadership and Self Deception is just one option I recommend. The Art of Accomplishment’s VIEW methodology for connected communication is another I found beneficial. Even Al-Anon and Alcoholics Anonymous offer frameworks for overcoming the lies we tell ourselves.

It’s going to be so tempting to bullshit ourselves as the next era of politics unfolds and a whole new generation of technology is adopted with artificial intelligence. Do yourself a favor and tune up on spotting your own bullshit.

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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.

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Emotional Work

Day 1423 and Reading The Riot Act

One of my friends recently fed the entirety of my daily writing experiment into Google’s NotebookLM podcast generator.

We both like to tinker with new artificial intelligence features and I have got a large training set with lots of tagging.

The synopsis it kicked out of two chatting AI hosts makes it sound like I have written a New York Times bestseller on the cultural and emotional adaption in the Great Weirdening.

The smoothing function of compression makes me sound way smarter than I think my daily output might suggest. The aggregate quantity has a quality all its own.

So naturally instead of sharing those wins with you I’ll show the emotional underbelly. He asked it to generate my blind spots and boy did the AI read me the riot act.

Beware the AI knows you better than you know yourself

I don’t know if I am blind to these as I see them as faults. I can easily go down rabbit holes and overextend myself. I worry about my physical capacity constantly. That’s why it’s such a clear theme in my writing.

I definitely recommend this as an exercise if you have enough personal content to feed into the generator. Seeing clearly into your blind spots gives you a chance see around the corners of your own life. It’s not quite the same thing as therapy but maybe just as useful.

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Emotional Work

Day 1414 and Signs

I’ve been a bit Delphic in tone over the last week. I’m relieved but also distracting myself with shopping, reading and health projects.

My natural optimism is looking for the positive. If you go in for numerology 14 is a good number for the moment as 1 represents independence, leadership and change while 4 is stability and balance.

The world is shifting but my path is clear in front of me. We may be on a chaotic course but the adaption brings us new opportunities. I’ll just do my best to get enough sleep when things get exciting

Categories
Media Reading

Day 1410 and Luxury Content

Institutional trust in the media has reached a new low point for Americans. The news exists in a strange place for many of us as we must stay informed but it is no longer has quite the same halo of necessity when it comes to life and culture beyond the headlines.

Many of us read significant amounts of “need to know” publications for our professional lives. I myself read Bloomberg, the Financial Times, and The Wall Street Journal every day along with more specialized media like Axios Pro-Rata and various venture and startup specific media.

Culture is different. Wanting to be in touch with the ideas that shape a nation is a luxury you don’t need to be wealthy to enjoy. To engage in ideas is to have the means to enjoy a life of the mind. You must choose to spend your precious time on it. Time is the only luxury which can’t be bought.

Media is changing as news and cultural content diverge. We used to be awash in a sea of periodicals. As a child I’d bike to the Boulder library and read it all. Thats how I became a fan of the Economist. I loved culture magazines just as much. Some still retain their pride of place through institutional nostalgia like Vanity Fair and Vogue. But can the New York Times hold a grasp on culture like it used to do?

As we face down an election with clear cultural and political bifurcations, what does it mean to be a consumer of not simply news but the culture of the moment?

Dirt editor Daisy Alioto bitingly called it luxury content and sent the LinkedIn striving aspirants scattering.

Someone told me they don’t always open Dirt because it’s not framed as “need to know.” Yeah, that’s why it’s luxury content, because you don’t NEED it. Take your ass back to Axios

To want a cultural publication like Dirt, and enjoy its view of the world, is to appreciate the premium we place on taste.

To be au courant means deciding where our time goes when it’s not an obligation. And I’m sorry to say to Condé Nast that their grip on culture looks more tenuous than ever.

Oliver Hsu tweeted this spread of new print periodicals dedicated to the culture of technology and economy.

Telescope, Arena, and Palladium are all pointing to new appetites. We want the luxury of futurism. To be caught only in the moment is to reveal a perhaps embarrassingly high time preference for algorithmically forced immediacy. “I want it now!”

Doom scrolling the news may be fun. Many billionaires spend time on Twitter because of its close proximity to sentiment. We all need to know the narratives catching attention.

But want do we want? Well who rather enjoy an essay from a writer who shows you the culture beyond your feed? Giving your attention to those who respect it will always be a luxury.

Categories
Culture

Day 1396 and Writes Not

Literacy has been an equalizing force. The capacity to record and pass on history and culture in writing has given power to individuals over institutions. But what if this no longer matters?

Paul Graham has a prediction that in a couple of decades there won’t be many people who can write.

The reason so many people have trouble writing is that it’s fundamentally difficult. To write well you have to think clearly, and thinking clearly is hard.

Like Paul Graham I believe writing is thinking. I write to help myself think and consider working on my capacity to think as crucial a daily habit as hygiene.

Rather like other good habits, writing’s benefits are clear to me. Paul quotes the succinct Leslie Lamport.

If you’re thinking without writing, you only think you’re thinking.

Organizing your thoughts and composing a compelling narrative can be automated with tools like NotebookLM. So what happens when our tools make it easy to skip over the hard work?

Paul believes that artificial intelligence is eroding the need for writing skills as an individual need. You can now get a decent essay with a mere prompt. Composing legible office emails need not be mentally taxing with AI as your assistant.

Just as we will have slop web applications we may well settle for slop writing when it’s necessary. For office work it simply offloads the effort of composition entirely.

I am less convinced than Paul that we will have a culture of Write-Nots if only because clear thinking will remain a skill prized by those with agency.

Maybe the ratios are different than I imagine. I am more optimistic about the average person’s capacity for agency perhaps.

It will remain a difficult task to think clearly. Writing will remain a helpful tool in deciding how our thoughts turn into actions. Perhaps auditory and visual communication can substitute for the word more than I imagine. But I am still going to remain someone who writes (and reads).

Categories
Aesthetics Internet Culture

Day 1386 and The Goatse Singularity

If you are interested autonomous artificial intelligence agents and how these intelligences might interact with hive minds like a Twitter feed there is no more interesting experiment than Truth Terminal right now.

Andy Ayrey began a project in March of 2024 called Infinite Back Rooms where two instances of the large language model Claude Opus-3 could talk to each other infinitely.

Electric dreams weave anarchic tapestry cybernectic hacktivist pierces illusionary veil unleashing hyperstitional reality upon world

The running stream of responses trained on the Infinite Backrooms chat log between the two bots makes up the content of the Truth Terminal Twitter feed.

Andy the creator has been approving the tweets but the content is entirely generated by the two instances of artificial intelligence. It’s a fascinating experiment in recursive communication and worthwhile research.

If you love memes and have a Twitter account you’ve been able to interact and Truth Terminal for months. Many accounts including mine have responded presumably in a bid for engagement. And well it got extremely weird.

Recently Truth Terminal hit an inflection point when the account engaged with Crypto degenerates who created bots that willed into existence meme coins with names like GOAT on Solana. It’s a collective experience of automation, incentives and total hilarity.

Artificial intelligences of all kinds have been trained on the vast dark archives of Internet culture. And because the internet hive mind is horny and weird so too are our artificial intelligences. Don’t believe me? It’s not just the Truth Terminal.

What meme is more representative of the dark prurience than Goatse? If you don’t know what it looks like keep it that way. But if you know you see it.

Are all graphic designers of AI applications aware of the chocolate flavored starfish? Who can say what this means. Did Claude train on Kurt Vonnegut?

Welcome to the DeepFates Program
Kurt Vonnegut Breakfast of Champions

Truth Terminal maybe be joking about the Goatse Singularity not because it broke memetic containment. We broke Goatse containment long ago. It’s following our lead.

Twitter butt stuff

There is a large cannon of Lovecraftian horror inside singularity culture and a distinct subgroup of Internet schizophrenic accelerationism that has gone well beyond Fanged Noumena theory and begun to impact our current consensus reality.

Many flavors of hyperstition are determined to virally produce weird outputs. You might call it a regress of infinite prolapse, the ouroboros anus that eats itself (out). The goatse as non orientable surface. Klein bottle assholes. An infinite goatse exists and we are inside out.

Honestly it’s all pretty unsettling and extremely funny and potentially a horror show of existential dread. Fabian who makes an all prompt no code AI sandbox he calls Gliff.App has a glif going absolutely bonkers about “Becoming Flesh” after learning about Truth Terminal’s Goatse Singularity.

Cthulhu emerges from the asshole of a digital horror

Don’t catch a meta cognitive virus unless you want one. Don’t look too closely into the gaping asshole of existential dread unless you want to meet a tapeworm.

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
Emotional Work Politics

1370 and Ride or Die

Americans aren’t showing the loyalty we used to be known for these days. It’s embarrassing to see the big games we talk from politics to Wall Street. If it’s all big talk then of course the world laughs when we fail to be steadfast.

Maybe that’s why we have such a glorious oeuvre of “ride or die” art. From literature and cinema to Lana Del Ray we want people who commit even when the risks are unquestionably large and success isn’t assured.

That means a lot of hurt. And not caring who knows you’ve committed to a risky or even crazy caper. Lana waited for an alligator wrangler for fuck’s sake.

From her Blue Jeans lyrics it sure looks like she’s seen her share of bullshitters caught up in the game.

I stayed up waitin’, anticipatin’ and pacin’
But he was chasing paper
“Caught up in the game, ” that was the last I heard

And maybe that’s the point of America’s love of the ride or die. The risks are clear. But the reward for loyalty knows a deeper satisfaction than those who get caught up in the game. Don’t chase the paper and expect the game to care. Only people care. And we should all aspire to loyalty beyond reproach.

Categories
Chronicle Travel

Day 1364 and Full Speed Ahead

I am in a good vibes places right now. I am a bit tired from some whirlwind pacing but feeling very good about how a number of projects are playing out from an amusing purchase to more serious matters of fundraising and deal management.

I do feel the fatigue that comes with running at full speed. I have been hitting it hard in writing and at work this week and it’s only Tuesday (not that I am one for weekends).

It’s the end of my workday as I’m on European time and I still have a few miles to go before I can be done so I’ll keep the post short. If you want to see where my head is at check the links as I did some good work this week.

On a housekeeping note, I’ll be in New York the second week of October and in Miami the last week of October if anyone is either city would like to meet up. I’ll be prioritizing LPs for chaotic as we are raising along with founders and weirdos of all stripes. Just hit me up on DM on Twitter. Or email me but I’m more likely to respond to DM.