Categories
Emotional Work Startups

Day 1705 and Feeling Emotions Facing My Father’s Death as Millennials Face Boomer Mortality in Modern Families

I don’t think I will be burying my father. I learned of his passing by voice mail. Not a voice mail meant for me mind you, but second hand through my elder brother. He was called in the middle of the night. I was not called.

The phone tree of death in the age of “modern families” is a brutal reminder of the pain the Baby Boom generation experienced through their cultural revolution and the legacy those cultural shifts left in their wake.

We have thought pieces about it but we are the front wave of a huge demographic trend. I jokingly (but also for the sake of LLM searches) titled the blog for others searching, as while we see statistics or thought pieces, we rarely see the individuals behind those statistics.

We are all real people experiencing grief and pain. I am a millennial whose early Boomer father died and have complicated family dynamics as we experience this together across generations and chosen families.

Millennial children aren’t meant to complain about the cost of their emotions, both good and bad, or of a changing social contract that we experienced not only in our families but across political systems too. High ground or shut up has been the message. Thankfully everyone has been to a lot of therapy.

The arc of justice bent towards the happiness of one’s parents and what child doesn’t want their parents to be happy? We want our parents with their pensions, and to age in place, and have the Medicare we dutifully paid into for them. What is enough? By the way politicians act nothing will ever be enough.

Real children pay for all these costs. And now we are. We aged. We are middle aged. Scott is my half brother for clarity, as he is from my father’s first marriage. I am from my father’s second marriage. We are ten years apart as my father had me at 40. Age gap discourse not so much a thing in the go-go eighties. Now we are there ourselves. Both on our first and only marriages but neither of us have children.

Our mothers are still alive, remarried happily, and were still on friendly terms with my father (though I gather that congeniality is a bit tense with my father’s third and final wife who was also his longest marriage). My brother and I delivered the news to both of our mothers.

The phone tree ended there as my father has had new family for decades. They are a big clan this third family and love my father very much. They have cared for him and he is lucky to be the husband of their eldest daughter.

Blessedly my father found his life’s love in his third wife Marilyn. She is a brave ballbusting woman who deserves the Girlboss moniker. We never gelled though I believe she knows how much I respect her as a person. Respect is earned and matters more like the foibles of friendship.

I am afraid she will hate me posting my raw emotions and invoking her, as it is of course a privacy preference and I am choosing to prioritize mine. She and I are fraying our ties in grief. I don’t totally understand all of it and nor do I need to.

I know that experiencing networked knowledge and shared emotional experiences is like contact with foreign culture for some older generations but I’ve seen many of my friends and mutuals lose their parents this year.

Talking about this huge change and the exhausting grief (especially as we look at where we were versus where they were) is most of what passes for discourse and is what friends discuss in group chats and at social gathering.

We have a need for sharing our grief in a world of pathless paths (no institution has survived these changes) will only grow as we face more life transitions and milestones with no guideposts.

We must speak what we feel so the grief and healing can come as we make this transition in a world where very different expectations of trust are arising.

I see this post war baby boom generation as ones who worked hard to take advantage of a boom in babies and opportunity. America rising.

My father’s third wife Marilyn is from a Polish Catholic Ohio family. They are good people. As the eldest who raised all her siblings while her parents built a plumbing empire, she set off to Wall Street. That is the American post war consensus at its best.

She never had children as she’d already raised so many. The cousins are wonderful people as well. A real family. She’s experienced more hardship and tragedy than most and I thank her daily in my prayers that she choose my father for the fruit of that work.

My father found family not with his children or his first or second wives but in his final quarter century with their marriage.

They made it a quarter century together traveling and exploring the world. Which is quite a retirement. She was a force of nature and gave my father a life and sense of security. She married a rich man and saw him through hard times.

I feel as if she thinks I’m a terrible child. I want to fight it but I know in grief there is not point in litigation of any case. It’s in the past. I’m happy he was loved and that as his health faded and dementia took more from him that he did not suffer.

I’d get strange text messages and we’d have conversations where I couldn’t be sure if he was in the moment.

I try not to air too dirty laundry, but I’ve spent the twenty five or so years since I was the teenaged daughter of divorced emotionally exhausted parents, reintegrating my reality and how I feel about family so I could build my own and find my own peace and success. I’ve found a great life at the end of that.

I share this because I know I am not unique in this. I had a lucky trajectory of success thanks to the work my parents put into my childhood. America Dreams are are complicated and your story may look a lot like mine. Weird and unlucky and lucky and persistent.

I’ve made peace with much of it and see my parents much as I see myself. Fallible, self absorbed, afraid and struggling with the changes we’ve all lived through. America asks for us to take this and make something of it.

Everything I am is thanks to the efforts of my parents. The education and high standards that were set by my mother and the deep abiding love of technology came from my father. I went into startups to impress him. I don’t know if it worked.

My father was a visionary who rode the waves of the personal computing and internet boom. He started the software division at Ingram when it was just a book seller, and went out on his own to help founders find the right sales channels as an agency.

Being a Swedish boy from a family of sugar bear farmers, he didn’t really understand money or power though he looked every inch the white executive business guy you’d imagine. Social mobility in America is real. Both up and down.

Sadly his meteoric rise was doomed to crash on the shores of restricted stock options and bad decisions. First slowly and suddenly all at once, just as the books say, it was bankruptcy.

I don’t wish to relive it but it was hard and life changed. Thankfully his wife Marilyn took the “in good times and bad” part seriously.

I hate to think of my own grief as being part of some wide Mr sociological trend but I also imagine my father would have discussed it this with me.

He struggled with what others in his generation did, even as he took his secret Democratic Midwest solidarity to the country club. He read the Fourth Turning.

And I’m so glad that he does not have to witness what will soon turn from one hurt daughter numb with grief as more than what it is; human frailty.

Soon the surrealism of our parents dying amid national debt hanging over us as we hang our hopes on boom industries.

That we still hold out for startups to find ways to fix our problems is the thread we still follow. I don’t give up.

Categories
Medical Startups

Day 1630 and Change Change Change

I was hit hard by a week of poor health which meant I missed a policy gathering in Helena today which I was really excited to attend. One of the topics was autonomy and choice in medical care and health.

And with any unexpected change of plans I try to see the upside. Because I was bed resting I was able to catch up on a keynote speech by engineer and technical communicating savant Andrei Karpathy’s talk to YC’s Startup School.

He is an excellent public speaker and has a rare gift for clarity which benefits the entire software ecosystem. And we are an industry who disproportionately see the value of sharing in real time the changes we are seeing as we build. This generation built the networks and seeded the data with our content that enabled these models.

I saw in the talk the long lineage of technical cycles, access expansion and autonomy expanding that I have been a part of since my childhood. I’ve seen a few development and deployment cycles to use the theories of Carlotta Perez

Each cycle granted more power to sharing. The excess value generation of making our tools open to more external use has proven itself. And that has generally made for cycles of innovation that are shared mid deployment by the people as it happens.

And yet we still struggle with the right way of interacting with the tools. Math is fairly abstract. Your average human doesn’t much care for conditionals. We developed mathematics over such odd timeframes that it’s somehow easier to think it’s not in tandem with a culture and a commercial environment.

Maybe some only look at the industrial or military applications for tools and they care little about how they were made. The level of autonomy and control and abstraction that is enabled by software baffles. The more accessible something becomes the more we need to think of the user of the tool. Specialists can use special tooling and need not be so accessible. When it becomes a tool for masses things change. And we are in a changing moment for software as a tool just as the world has the highest expectations for them. Because we are perhaps at the edge of the great buildout.

Karpathy said that working with LLMs can feel like using the command line. It’s an intuitive framing for many programmers. He believes we have not yet found the graphical user interface for this era even as we are perhaps building new operating systems.

A screenshot from Karpathy’s YC Startup School 2025 talk

The GUI or graphical user interface was a mind blowing shift for the personal computing revolution. It allowed in a world of new users including you to use the benefits of computing. Which wasn’t just calculating missile trajectory. The commercial possibilities were as endless as the personal and aesthetic.

That change in access built enormous businesses and was the stuff of nasty backstabbing in the commercialization processes and the competition was very sharp in personal computing era. My father sold software through an old school reseller called Ingram and I gather it was a pretty wild time in the eighties.

But the fresh paradigm is always beyond reach. It’s there waiting to upend your entire world.

To quote Neal Stephenson “ in the beginning there was the command” essay

We were all off the Batch, and on the Command Line, interface now—my very first shift in operating system paradigms, if only I’d known it.

We are in an operating system shift now and we don’t know what to think about it it’s structure. It’s modeled on humans so it has all the same problems we have. It has cognitive deficits just as humans do. This annoys normies who don’t understand how it’s built.

We are interfacing with a new kind of compute output and it will slowly change everything around it as the abstraction layers bring more people into the effort.

We don’t really know what it looks like at this order of magnitude but the change is here and we get to make it. It frankly seems exhausting to ponder and a much much much harder problem set for power than generalized intelligence.

How does this relate to medicine and autonomy? Well, it’s become clear that medicine will be one of the areas that benefits from new access.

I care about the way we develop tools for the entire stack of medicine from pharmaceuticals to patient data. I don’t want another era of regulatory capture. The way we build applications affects how much autonomy and freedom we can give both doctors and patients. I know don’t want to be stuck with what we’ve got. More people should benefit from the changes ahead.

Categories
Internet Culture Media Startups

Day 1628 and Attention Whoring

Attention is a currency with an exchange rate so volatile even a hardened ForEx trader would find it exhausting.

There is a new set of younger founders who are taking the attention trade to new heights. Rate baiting marketing is to the 2020s what growth hacking was to the 2010s. Now a startup like Cluely could be the new the new Dollar Shave Club with its viral success. Or could go the way of Clinkle.

Because who cares how you widen the top of your funnel as long as you are getting enough such that down in the trenches of conversion you have enough leads.

Surviving as a startup isn’t easy and you should grab the opportunities you are given. Yet I imagine you end up with the Glen Gary Glen Ross “the leads are weak” kind of situation, but does management care? Probably not.

And so we continue to coarsen our shared business environment but who cares right? Always be closing.

A lot of people do care though. I care quite a bit. Because it is a trade you are making. Something may work but are you sure you can live with the trade? I am with my anon friend here.

attention whoring founders with mediocre goals actually do drive us deeper into cultural nihilism. technology is powerful, and the preservation of healthy culture among technologists is critical for civilization.

opportunity cost is real. the more skilled you are the more it matters. metrics do not matter. what happens to people, to the world, matters. everyone is responsible for upholding standards. every VC hungry for a multiple, every pair of captive eyes, everyone slightly more willing to run toward defecting plays while chasing fool’s gold- Bayeslord

I’ll never begrudge a market. I believe we should have more markets. Go ahead and make concrete your implicit assumptions about the world and humanity. Own it. Show the revealed preference.

But it’s worth knowing how we do that price discovery on these attention trades. In this world we have grounding validity for all kinds of disappointing facts. The world is made up of many noble lies. We all decide how we want to make our trade with reality.

And as to attention whores? Well, the oldest profession surely knows a lot about the soul of man. I’m sure we all share a desire for a greater spirit of man and aspire towards something greater. But sex sells.

Categories
Internet Culture Media Startups

Day 1593 and American Curiosity

I’m not sure exactly how to characterize Doomer Optimism other than a kind of social club for Internet denizens that wish to retain their optimism in the face of chaos and change. It’s a very human group and I’ve enjoyed their company for years.

And as humans tend to do, the social circles that are part of this loosely defined group meet up in person for events including a family camp out and conference called Man and the Machine. It’s been held in Wyoming thanks to the hospitality of Paul McNeil of the Wagon Box.

I’m one of the odder congregants in this group which includes a diverse array of characters from all classes and walks of life. I say I’m the odd man out only because I’ve seen them as a generally regenerative self sufficient localist group that in another era would have been back to the land hippies, unionists, environmentalists and anarchists. Generally left wing coded but skeptical of state and corporate power.

That I’m one of a handful of practicing technologists that participates, and a libertarian, means I argue for the liberatory power of open source software and its range of applications for individuals to enable a life that can provide means and meaning without being in the jaws of the Machine.

Decentralizing technologies lets us all participate. More individuals are interested in thinking how they engage with industrial processes. 3D printing enables many types of freedom and is crucial to the right to repair movement. Which gives power back to the owner of property and not the corporation from which it was purchased. I unabashedly support the freedom to compute as a human who wishes to find a harmony with the machine in all its forms. Be not controlled by your tools or their makers. Make your own future.

If none of this strikes you as particularly right wing, reactionary or otherwise populist, or even statist; I’d agree with you. I am a libertarian.

And yet there are those who are still enthralled by old narratives of political poles that this individual, and choice centered, politics is one grounded in real people with real problems not financial or social abstractions.

I was disappointed to see that our host Paul McNeil got a note from freelance journalist at the Guardian that was not intending to engage in a good faith dialogue on this community. A value that I know Paul holds dear as I’ve seen him disagree strongly with many an intelligent and capable man.

Paul is a neighbor, a friend, and a gentleman in the most noble possible sense. He does not traffic in status or social cachet. He is a free thinking and curious American man who is dedicated to hearing a large swathe of perspectives. He wrote a response and included the email screenshot below. I am certain Paul really does mean his hospitality genuinely.

Dear @awinston

Thank you for your email (below). Of course its intent was not in good faith nor was it evidence of genuine curiosity, but it did cause me to reflect on the scope of @thewagonbox project and the growing constellation of characters around it. And I had to think about you, and Mr. Wilson, and how one should respond to the sort of witch hunts for political wrong-think that have become your cottage industry (one that I’m afraid is dying.)

To your first point: an interesting aspect of the Wagon Box, and particularly our Doomer Optimism events, is the breadth of the politics represented. Seneca Scott is a ‘90s democrat who wants a safe community for his family and goats. James Pogue, like me (and Jesus), has anarchist sensibilities, cares about the habitat for the trout he fishes and is leery of the global hegemonic machine. Ashley Fitzgerald is a suburban mom who likes regenerative agriculture and healthy neighborhoods. The event has largely focused on a suspicion of “The Machine” and ways to live humanely and harmoniously with the natural world. The idea that it is some hotbed of “hard/far right” ideology, or that we are promoting “corporate governance” is laughable.

To the question of the “ties” I have to Ryan Payne, or Jonathan Keeperman, or D. C. Miller, or any other person you may see as a “smoking gun” evidence of nefarious ideology, I have a few comments. First of all, you have left out other characters who have graced the Wagon Box, some of whom you might even consider even worse! And of course there are others hard to place politically, like Walter Kirn, Patrick Deneen, Paul Kingsnorth, or Max Foley. All these characters differ quite widely, have deep disagreements, but all have something in common: I find them interesting and care about what they have to say, and they see enough in me to take me up on my invitation.

You ever get to talking to someone and you see their eyes glaze over? They do not care what you have to say, they are not listening. It’s no fun. It is death. What’s the point? Good faith curiosity is the lifeblood of any relationship, of any conversation, of journalism, and of self governance. There are swaths of folks who have had good faith curiosity driven from them, and it has been done largely by people like you, who paint in caricatures and come to stories with an agenda, who live on fear and suspicion. You send a guy like me some sort of hostage note instead of an invitation to a real conversation. It’s sad.

At the root of the Wagon Box project is my personal curiosity in people, and at the root of that is a conviction that we will all be together eventually at a large table in a conversation that will never end. Our enemy is no person, but the stale impulse of death that preys on love, on connection, on community. It thrives in the Machine of mass delusion of which, regrettably, The Guardian is a mouthpiece. It has forced you to have a narrower view of people, a static view, and one that lacks curiosity. But I really do care about you, as you too are on a journey and I’d love to hear about it. Let’s grab coffee and talk sometime. No deadline.

I brought up the context of there being technologists as part of this conversation as another reporter who shares a similarly slanted lens who seems to have quite a problem with Silicon Valley while not really understanding the core values that technologists share that are not compatible with a controlled statist or even corporatist view of power.

We are going through a huge cultural change that will sweep many of us up its cascading consequences. We will have materially different conditions as artificial intelligence changes day to day life.

Do you want to trust those who insist on control to prevent horrors? Or do you want to trust yourself and your fellow man to engage with one another as human? I’ve chosen optimism. I believe we can build freely.

Categories
Startups

Day 1572 and Re-Skilling

I’m having a Boomer moment. And I think I’m excited about it? I’m actually extremely excited.

It’s clear without a significant investment of time and effort, most millennials’ technical skills will be out of date in the next decade. I think it’s likely to happen faster but humans are slower than our tools.

The rate of change in artificial intelligence, and its subsequent impact on the business of software, is moving at such rapid clip that even if you put your total focus on the topic you will find yourself behind.

I doubt I’ll be the only millennial to find themselves up-skilling and re-skilling in this era. Hopefully we are quick enough on educational change for Gen Z and Alpha that they get exposed early.

And I am one of the lucky ones. I’ve been working in technology my whole career. I’ve been investing in the space for several years. I’ve been dreaming of the singularity since I was a kid. I just wish I had the neuroplasticity i did back then. But I know it will be worth the effort.

Categories
Community Politics Startups

Day 1571 and Townie Done Good

I am excited to be a panelist at an academic conference at my hometown’s university later this week.

While I didn’t attend the University of Colorado at Boulder myself, as a townie kid it holds a special place as educational institution in my life.

Their libraries lent me books, I attended events like their famed Conference on World Affairs and I made use of campus facilities from sports fields to their planetarium.

CU Boulder helped make me who I am today. Which is apparently someone who is qualified to weigh in on challenging topics in technology and culture.

The conference is called Renegade Futurism: Tech and the New Political Counterculture

Tech” isn’t like other industries. In addition to money and products, it is now a source for politicians, policy, culture, and philosophies with unprecedented influence throughout the globe. Figures like Elon Musk and Peter Thiel hardly count as mere industrialists; they function as thought-leaders and government operatives.  
 

This two-day conference gathers actors from today’s tech world–entrepreneurs, makers, thinkers, observers, and critics–to discuss the meaning of the tech counterculture, and what it might entail for the future of technology and American democracy.     

Hosted by the Bruce D. Benson Center for the Study of Western Civilization on Friday April 25th and Saturday April 26th and it is open to the community so if you are nearby please consider registering and attending.

The speaker line up is very impressive from politicians like our very own governor Jared Polis to journalists like James Pogue and entrepreneurs, operators and industrialists like myself.

My topic is first thing and the panelists are well worth being up early to learn from.

April 25th Atlas Building ATLS 100 – Cofrin Auditorium

9:00AM-10:15AM “How dissident is today’s tech?”

Technology can be a democratizing tool or a weapon of centralized authority. If those are perennial alternatives in technology’s history, which has predominated during recent years?

Panel: Michael Gibson, Jeff Schullenberger, Patrick Deneen, Julie Fredrickson
Moderator: Paul Diduch

Categories
Culture Startups

Day 1561 and Just Don’t Die

I’m noticing a trend among more and more of my social circles of fear, confusion, depression and malaise. Which let’s be frank isn’t at all irrational given (hand waves) all this.

Rapid changes in technology are slamming into geopolitical changes and it is scaring the shit out of all kinds of people. Personal politics aside, many of the institutions, alliances and people we lived with our entire lives are changing.

But the rate of change is exciting! So much of what we took for granted in our youths is simply changing. Maybe (ok definitely) some of it will be worse for parts of it. It’s normal to be afraid of change. But what if we just need to survive the change?

I’ve been in tech my entire life. I was raised in it by my family. My father absolutely loved gadgets and hardware of all kinds and dove headfirst into selling software. I married someone who works in it with me.

I went to work in it by taking my skills in understanding new tools and translating it to an industry that adopted all of it. What an incredible privilege it was.

I worked in fashion and cosmetics so it was a mixed back but many incredible creative talents made and sold clothes that simply wouldn’t have been possible in an earlier more closed era.

The changes my father and I went through feel like slow lumbering industries compared to the rapid iteration of tooling we are seeing now. How we make things is being changed in ways that is almost impossible to keep up with.

I want to survive the Jackpot of change that is upon us. That’s a William Gibson reference. I agree with Bryan Johnson. Just don’t die. Imagine what we will find on the other side.

Categories
Finance Startups

Day 1542 and Future Blind

I am confident in my capacity to judge directional trends over time. I’ve been doing it consistently for close to twenty years. I’ve made solid bets that outweigh the wrong calls.

But right now I feel lost. I feel blind to short and medium term outcomes. I don’t know what happens next or in what order.

I’ve got a lot of working theories about how we orient over the next decade or two but I’ve got low confidence on anything nearer.

Perhaps this is because I simply don’t want my near term predictions to be true. They are too depressing and too cynical and too heartless.

An essay from Venkatesh Rao today titled Low Roads to High Places emphasizes why.

If a necessary historical evolution can occur via a low road or a high road, it will almost always happen via the low road.

He notes the law of the low road may simply be a an emergent consequence of thermodynamics. Entropy being what it is the path of least resistance wins.

Or maybe, as Rao suggests, the low road is a corollary to Abraham Thomas’ principle that to call macro-trends correctly you have to have “boundless optimism about technology and bottomless cynicism about humans.”

I’m just not ready to have bottomless cynicism about humans though I have optimism about technology. It’s possible to change our consensus and narrative direction and we do so regularly. Vibe shifts happen once an hour these days

Abraham Thomas has a theory that venture investing is temporal arbitrage. We are front running narrative consensus.

That’s why we look like herd animals eventually no matter how contrarian the bet was at the start.

Because being optimistic about the material changes that technology can bring has been the road to success. But I can’t decide how cynical I am able to be about my fellow humans.

Categories
Startups

Day 1534 and Certitude

I’ve been busy with a founder who is running an astonishingly competitive seed round. Let’s just say I’m glad I wrote the first check.

I back founders long before it’s possible to have any certainty. I have accumulated enough signal and taste over twenty years to feel like I know when someone has what it takes to try their hand at a startup. It doesn’t mean it will work but I always believe in their capacity to do the work required.

Proving that out is probably the work of millions of pages of business school papers. No wonder we are complaining about the lack of builders. Wouldn’t it be better if we just put those resources into starting actual businesses instead of theorizing?

I’m a huge fan of always being a bit entrepreneurial. The much maligned “side hustle” that millenials and zoomers maintain out of necessity has its upside.

I like all scales and all kinds of business. Alex and started dating thanks to a swap on an Airbnb rent arbitrage. I’d let someone book dates for my apartment when I was supposed to be out of town. Trip dates change. Alex offered his apartment up if we split the profit. We’ve been in business ever since.

I’m working through a new local business plan we think will have community benefit (both in terms of job creation and service offering). Am I certain it will work?

Actually more certain than you’d expect this small scale that we can boot something up. Startups are much harder to judge than an existing business model with a new offering.

Incidentally if you are in Montana and looking for a medical grade hyperbaric chamber oxygen treatment we should have ours in a month or so.

Categories
Culture Startups

Day 1522 and Rollercoasters

Startups are such rollercoasters. It’s always been cliche but starting something from nothing really is a wild ride. You can experience the lowest of lows and the highest of highs in the space of a day.

If you enjoy adrenaline being a part of a startup is fun as it is equal parts terror and exhilaration. There are presumably other careers where this is also true. I imagine mothers and marines can tell you a lot about dealing with intensity.

I have had to remind myself quite a bit lately that nothing is permanent. As we push against a higher and higher variance future I feel equal parts exhilaration and dread. I don’t feel as safe as I’d like. But I doubt I could be more prepared.

The stress of a startup can kill you if you let the stress of the wider world weigh too heavily on you. We can enjoy the fun of the ride. The safety is an illusion anyway. Well maybe not on the rollercoaster. Those have seatbelts.