And I got to about May and realized I didn’t feel like I needed to put more into the organization. I had 4 medical procedures involving surgery. My father died. My best startups all raised rounds to scale. You can find your own way from there. It’s been a hard year despite the wins.
Much as it amazes me, I have written a public post every single day without fail for five straight years. I’ve not missed a single day.
I’ve written so many posts and essays, it honestly astonishes me. I didn’t expect to have this kind of longevity when I began but the world changed a lot in this past half decade. I am a woman of habits & routines, this blog helps me manage the chaos and instability that surrounds us. And hopefully I’ve become a better thinker (and writer) for this habit.
So now it’s time to think about year five of the experiment. 2025 was a hard year for me even as it contained incredible wins. Going into it, I wondered how could year five top the past four years chronicled here? It both does and it doesn’t. Life, and the time we spend living it down, isn’t getting any easier. Life is barely human at all anymore. I feel the struggle in myself as I am still very much human.
It’s easy to feel as if I’ve not accomplished as much as my own written records show I did. If you ever feel like you get less done than you’d like, I encourage you to keep a log or journal as it helps show how much can do and how much does get done. Plus if you publish it online you’ll contribute to a wider humanistic understanding as our digital life becomes more mechanistic.
Another facet of this writing experiment has been fighting a chronic disease in my personal life that has no cure. Managing disabilities during with the pandemic years as it overlaid civilization shaking political and technological changes has been hard. I want to work and live as if I am healthy and it isn’t likely to ever be true. I work smarter because I can’t work harder.
I don’t always write about my investments in these posts, but I see how my thesis of chaos has forced us all into requiring more decentralization, compute and power. My once weird ideas are now common knowledge. Now everyone agrees with me.
The end of the neoliberal consensus and the beginning of the artificial intelligence buildout would have been hard on anyone. I’m proud that I was able to turn this change to my advantage.
I realize I’ve written quite a bit about the experience of these years where I wrote daily without showing off the last year of posts.
Since I’ve got one more day before 2025 officially ends, perhaps I’ll put the round up of posts tomorrow as I’ve given an overview of the experience of half a decade of daily essays today. What’s one more day among thousands right?
I get out of America with as much frequency as I can manage. I juggle this with an intense patriotism not only for America but for my home biome in Rocky Mountain west. I am proud to say I am from Montana when I am abroad.
My interest in being regularly abroad began as an effort to source deals and understand different technical ecosystems, but has ended up being my barometer of what reality is being played for what channels. Deals get done where the founders are and it will remain so.
Yet if I didn’t see other economies and live outside of the news ecosystems of America I’d have an understanding of reality that was incomplete.
The projections of your interests as an American are in constant tension with the ex monica and cultural attacks on it from its adversaries. America has quite a few and it is extremely dangerous now to be blind to their impacts.
I don’t think our world will be as open in the future and this saddens me. When I visit a young formerly communist city in Europe I mostly see enterprising young people who see an. American and have positive associations.
The vibes Zoomer Eassyerj Europeans have towards a middle aged American from Montana is surprisingly positive. I am feel lucky that is their emotional connection to America.
And we shouldn’t take that good will for granted. We want America to be a good friend to them. Capitalist Zoomers who experienced totalitarianism and socialism are good friends to Americans.
The Christmas story is almost too layered to with truth to hold any but universal mythic truths this far from its historical origin.
We hear parables of the unexpected guest who arrives late at night seeking shelter. We are taught about the faith we must have in our families even when they ask us to believe in the impossible.
The Gospel of Luke (2:1) says Caesar Augustus issued a decree that “all the world” should be registered, so “everyone went to their own town to register.”
Imagine putting a pregnant woman on a donkey just to be sure you’ve got the proper tax regime in place. Empire is as Empire does.
In America the census comes to you. In Rome the census journey was the means by which Jesus’ birth occurs in Bethlehem, aligning the birth story with messianic expectations.
Why am I thinking about systems of record keeping on this holy day? Well I suppose it’s because on religious holidays days I have the space to consider what our future systems of record may be and how we will weave together the miracles that may show us the future of who we are to be as humans and as Christians.
Accounting and record keeping are relatively new inventions in the grand scheme of human development. Tribal knowledge assumed we could keep track. Empires needed a bit more structure and a lot more systems of record keeping.
What will we need as the nation state change and reform and the empires of this century are formed more by context graphs and nodal pathways than census takers and taxmen?
We are reinventing the living records of decisions we once traced through men of power and means but are now stitched through corporate entities, personal trusts, accounting norms and our attempts to find sources of ground truth we can all agree upon.
Trust and power dictated that in the past but now we need new ways. We must explain not only what happened but how it happened and verify it across decentralized systems in open systems even when much of our knowledge is tied in closed systems and protocols whose rules we’ve never fully articulated expect to a few high priests how they run run.
Technical documentation becomes precedent as Jay Gupta of Foundation Capital said in a thread. I bet he didn’t expect that to end up in a Christmas story either. Funny how life and history works isn’t it? Merry Christmas to us all. And may the day bring you tidings of great joy. Or at least a protocol handshake that is a bit easier than heading to Judea by donkey.
I’ve been using WordPress for a long time. Like rounding the corner to twenty years (in actuality going on 17) of time in the open source content management system.
Blogging was the new hot thing when I was in college. Blogging platforms emerged out of the strange tendency millennials and Gen Xers had for publicly sharing their own self reflection. I presume we got this from the Me Generation who raised us.
“I learned it from you Mom and Dad!”
Those early generations of social media all had flavors of being oriented towards writing with some multimedia mixed into mediums that were immersive and hyperlinked m but also narratives shared in reverse chronological order because the norm.
We went from Geocities to Livejournal to blogger, Typepad (RIP), and WordPress over the course of a few booms and busts. If you were blogging before 2005, you probably could have made a career out of it.
I don’t just mean writing, though lots of bloggers because professional writers, but whole online communities turned into careers from fashion and beauty to legal and financial.
Alas, the type of person who might once have made a wonderful career out of being a writer was caught out by the gutting of print media. America lost especially the kinds of middle class aspirant jobs that local news and independent publishers once provided for all kinds of creatives.
I’ve watched many platforms attempt to replace media jobs. Tumblr once hired a stable of writers. So did Medium. Neither ended well for anyone. Watching the comings and go of platforms and networks instilled a kind of paranoia in me about owning your own space.
I prefer posting under my own name on my own domain on an open source maintained piece of software as a back. I don’t pretend like I own my distribution on any social media channels. I’m sure Twitter will always be around wink wink.
So I am inclined to distrust Substack though I am reading more and more on the platform and I’ve enjoyed writing my own beauty blog there in the last few months. Thus far they managed to thread the needle on making money and making a social network and I don’t feel fearful that it will suddenly disappear like I once did.
Which is really a shame as it’s designed almost completely for the Gen C and Millenial set who really wished they had media jobs. The most successful did have media jobs and realized they could make more as an independent niche like the venture beat or by pandering to a very specific demographic or market that the giant media platforms don’t like.
These professionals class writers have a preference set for how they do content management and writing that just doesn’t remotely overlap with how I like to write. They want easy peasy hit publish. I want mobile. I want cross platform writing. It’s funny to finally have a content management system solve for monetizing and it’s just not made for me. But distribution and payment matters so I’m not booting up anything on my own without handling that first.
Tis the season of “unwrapped” data round ups as technology companies owe remind us that they have very capable data teams without unnecessarily freaking out users.
The marketers get all the glory, as everyone figures it’s a few MySQL queries gussied up with a creative hook but I always wonder what happened to the great data and behavioral science fad of the early teens. We’ve moved beyond IFTT and Zapier into natural language vibe coding. It’s a time of incredible change in understanding the data we’ve lived inside for years.
I got my fifth year of Whoop end of year marketing when I woke up today. Which was a little annoying as I wanted to see my sleep from last night but who wants to rush through the end of year review right? Finding it again can be tricky.
I keep wondering what more can we get from the hardware that knows us best. I’ve given half a decade to Whoop and mostly what I’ve learned is Covid really took 20 points of my heart rate variability.
I’ve been frustrated of Whoop’s progress in the integration of a chat AI as it seemed like any commercial LLM could analyze screen shots of the Whoop as well as their own chat did with the data it already. But tenure counts for a lot and it’s still the tool we have all relied on for half a decade now. Or at least 2% of us have worn it everyday for that long.
Clearly the data l could be used in many more way more than the management team ever seems to enable their data teams to do regularly. And I’d like to get more out of my Whoop. So being reminded of the length of use makes me wish they would deliver on that future before another year goes by.
There has been quite a bit of discussion in alignment theory with artificial intelligence that considers how legibility and openness might work at cross purposes when coordinating across different intelligences with different goals. Politics exist everywhere it would seem.
If you are transparent, but seek to change an agent’s behavior, you might reasonably be interpreted as adversarial by the agent. So it follows you must consider that their actions are no longer collaborative and open towards you but potentially adversarial and opaque depending on how it judges you.
The information habits and “winner’s optimism” that some American elder millennial display in public digital spaces are telling. In particular, we have skewed heavily towards legible openness as our internet was often friendly and our geopolitical positions was dominant.
These conditions are no longer true. And so we are now experiencing the Dark Forest Theory of Yancy Strickland (based on Liu Cixin’s stellar science fiction series the three body problem). American millenials are on a very different internet than we grew up on.
I’ll admit I have a bone to pick with Yancy as it felt more like he was defecting from the open web in 2019 because it was scary and filled with fascists. I didn’t think he believed it was because it was actually dangerous. His return makes me question his original declared intentions and his goals now.
The Dark Forest disappearing man has come back to the open web now. Things have changed and we all need our own private Idaho. Which you can find through his offerings.
I’ll note he needs the distribution channels of large adversarial networks like Twitter and that means gaining power in the dark forest. As we consider how open and legible to be in this very difficult moment I thought this was an instructional revealed preference.
The center does not hold. It is not holding. We are just not adapting to the changes in reality quickly enough.
If you get too close of a look at the basics of what’s necessary to survive a world where the trust is breaking down it’s hard to look at.
It doesn’t feel like we are going quickly enough adapting to a world where the state can’t perform its old functions and smaller entities like businesses and families need to maintain a heightened awareness of the larger context.
The joke has always been “don’t invent the torment nexus” but we seem to always invent the torment nexus if it will have a good return on capital. And we need to take this outcome quite seriously.
I’m starting to think the more optimistic you are about the future, the more cooked you think we are. I didn’t expect this.
The Doomers have a coherent worldview. It’s simple to imagine involving losing your humanity to machines. This is at least legible and a call to our common humanity. Change is scary and bad and we don’t know how any of this is going to go. So why not be cautious?
The optimists are all excited about different things though. And that opens us to a lot of attack paths. And yes I’m calling myself an optimist though I have a lot of downside scenarios on my radar.
Some of the outcomes that you might find dystopian are the utopian outcomes for someone else. Think Caliphates or Communist surveillance states.
The complexity of our reality is so far beyond the grasp of your average person it seems cruel. And we sympathize with the struggle to adapt because it appeals to our common humanity.
It’s no wonder America has had so many revivalist movements. We have changed so much in our 250 year history, we are always rediscovering the value of faith. What else do you have when the future is uncertain? If we are cooked anyways we may as well all take Pascal’s Wager?
I often wonder how it is that venture capital remains so male-dominated when most of the work is the same skill set as a fashion editor or a style writer.
Sure, you occasionally see a man with good taste, and the twinks and gays are obviously the best of breed in both venture and fashion. But the game is basically the same. And yet fashion is dominated by women and venture as an esoteric sub-asset of private equity is very much not.
Let’s compare. Venture is a small, tight-knit group of people, who run on backchannels and gossip, and absolutely everything is determined by being the first person to land the next hot thing.
Now there is an avant garde who sets trends which then get validated with market success. In venture these are the earliest angel investors. In fashion, it’s the indie publishers who slog through the upstarts and pick who to champion.
The angel investor hopes their deal will go to later stage investors just as the trendsetting editor hopes their designer pick makes it to Vogue. Picking the next “it” thing and riding the wave to fortune is the goal for editor and designer, just as it is for investor and founder.
I personally think my skills are validated just as much being the person to get Mansur Gavriel added to the right boutiques as I am being the first check into Valar Atomics.
I took my bag to a breakfast at a boutique investment bank (you know the one with the summer camp) and happened to be meeting with an investor who loved the bag so much that the founder of their luxury ecommerce investment picked up the bag to stock immediately. Well over a decade later, I still carry that bag almost everyday and so do millions of other women.
Now ask yourself if this next story sounds pretty similar. I sent a direct message on Twitter to a young founder who seemed interesting. He had a quickness to his thought I respected as well as humility that set him apart.
Alas I didn’t like the company he was working on at the time and I didn’t like that he wasn’t its CEO. Sounds like “the food was bad & the portions are so small” sort complaint right? Well, I just thought he was so good he should be the lead in whatever he did next.
The young man had partnered with an experienced elder (which was probably wise for that industry) but the founder was clearly the dynamo in that situation. I told the founder that straight up. He had earned complete candor from me.
We began talking about what he really wanted to build. His intensity was awe inspiring. And his vision was just so crazy that I knew I had to back him. Many phone calls and strategy sessions later I wrote a check. It would take less time than I’d dared dream for others to see what I saw first.
To see him now as the jewel in the crowns of many much larger funds and backed by much more impressive and capable people than me feels amazing. I’ll always have the satisfaction of being the first to know he was going to be the next big thing.
And that’s not so very different from helping select the hottest hand bag of the last decade. Like Jeremy Irons’ character in finance classic Margin Call, I know the value of being first.
There are three ways to make a living in this business: be first, be smarter, or cheat.
Now, I don’t cheat. And although I like to think we have some pretty smart people in this building, it sure is a hell of a lot easier to just be first.”
If Isaiah’s work is successful, it will be an awful lot bigger than the hottest handbag. It will materially change the conditions of fueling our lives.
And while I am pretty smart, I knew enough to act first. Because it was a hell of a lot easier to just be first. And if I’m lucky, I’ll carry my bag and own equity in Valar for a long time to come. Read the full story in Bloomberg with a gift link.
