Category: Startups

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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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Startups Travel

Day 1442 and EOY Yet

The pace of 2024 hit me like a ton of bricks today. I haven’t fully unpacked my suitcase since September and honestly I couldn’t even really tell you my full schedule without checking my calendar.

I’m pretty sure it was only New York, Miami, Los Angeles and San Francisco but it sure feels like more. It’s been a lot.

I am coming around to enjoying some aspects of travel again but I feel like the only way to get deep thinking done is when you are able to stay put for at least a month.

I’d rather pack in multiple weeks on the road and then hunker down and assimilate. Others seem to do well with breaking travel up more. They do a week on and off.

I find that I don’t adjust in and out of travel quickly enough for that. It feels like state of perma-travel to my mind and body. I like to have a lot of steady continuous routine. My workload is literally chaotic (aka our preseed venture fund) so I don’t actively seek stimulus.

I just have a few more things to get through over the next couple of weeks but I am getting glimmers of stability and quiet. Which I very much want and need. Just need to hold it together a little longer.

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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.