Tag: Confidence

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Culture

Day 1551 and Jokes On Us

April Fool’s Day is just the worst. Practical jokes were much more enjoyable when telling the truth was still a widely accepted social norm. Our moment is one of a thousand falsehoods.

Our commitment to the truth and a shared sense of what separates truth from falsehoods has never felt shakier to me. It’s one strategic lie after another from all our institutions and leaders.

If you are living in our era of lies, half truths, and various flavors of misinformation & disinformation the idea of dedicated a day to falsehoods seems perverse. I don’t want to be on the Internet or a part of discourse on a day when deliberately lying gives you social capital.

Alas this is an ancient human custom in many places. The Indian festival of Holi, medieval Feast of Fools, and the Roman Hilaria are all early spring celebrations of pranks, jokes and foolishness. The prevailing theory dates to France and the change to the Gregorian calendar.

April Fools’ Day back to 16th-century France. In 1564, King Charles IX adopted the Gregorian calendar, moving New Year’s Day from late March (around the vernal equinox) to January 1. Those who continued celebrating the old New Year date on April 1 were mocked as “April fools” and became targets of pranks, such as receiving fake gifts or being sent on “fool’s errands.”

– Via Perplexity

I rather imagine that the religious traditions mentioned above all valued truth as a foundational virtue. To know the truth of the world and the truth of your soul are the twin ambitions of human life.

Perhaps I’m being too sensitive. Or too rigid. Humans are evolved primates and we play status games that involve deception in the entire primate family. But I’d still prefer that we communicate true information to each other as both a norm and as an aspiration. That’s not a joke.

Categories
Emotional Work

Day 1548 and Future Perfect

Back in my distant Williamsburg hipster past I lived in a loft above a furniture store called Future Perfect. I am lucky enough to have acquired a couch from them but that’s a different story.

I didn’t envision exactly the kind of Future Perfect that I and the aforementioned coach would come to inhabit. Both the couch and my current life would have seemed crazily out of reach to me in the middle aughts.

This isn’t to say that life turned out perfect but it feels closer than I might have imagined. Many aspects of the future I was hoping to live seem almost comically small in their scale compared to what’s actually possible.

I hope this remains true for the future perfects that are yet to come. I see the rapid change in technology and I feel hopeful. Then I remember human nature and I have more trepidation. Either way, all I can do is take good care of myself now.

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
Emotional Work

Day 1538 and Reason About the World

There is a pet theory that I ascribe to that precious few changes their minds without experiencing a failure in social consensus. Being pushed outside of culture lets you map it more accurately on the way back in.

There is nothing more valuable than your ability to reason about the world. We sense-make with all kinds of inconsistencies and have so little incentive to step out of what we think is true about our world. Go along to get along is how humans stay alive.

I have had a wildly inaccurate model of the world in the past and I’m confident I’ll say that same soon in the future.

But I’m comfortable falling out of social consensus if it clashes with the model of the world that I work within. I’m not saying I’m smarter than anyone but I do know that I regularly weigh my faulty priors even if it’s embarrassing. I’ll keep searching for people who can reason about the world. We can see better together.

Categories
Aesthetics Culture Politics

Day 1537 and Copy Cats

A friend of mine has managed a career as a tastemaker of the sort that hardly exists any longer. It’s hard to find a term that’s even appropriate without both identifying them and understating the power of their influence.

Influencing the direction of culture isn’t so much a job as a point of view with a paycheck. It used to be a bit simpler. We had a hierarchy of influence caped by physical realities.

Maybe your pastor or your employer influenced your daily culture. Even when I was younger it wasn’t much broader than your local news and what you could get at the library. Now we live in a mass market of influence.

Influencer, creator, journalist, editor, blogger, hell we even have Twitter accounts that move culture now. So it’s not surprising that it can be hard to keep track of who is truly influential and who is just popular.

Being heard out and being really listened to and considered are very different things. It’s a weird moment for taste. Especially culturally. We keep having vibe shifts. The people who are paid to make sense of it all are as clueless as the rest of us.

The only thing anyone can seem to agree on is that it’s all very chaotic. Which is a point of view with which I’m quite familiar. And naturally that unsettles me. Once everyone agrees on a cultural moment is exactly when the tastemakers look for something new and when the masses really come with the big bucks.

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 Politics

Day 1533 and the Long View

One of the oddities of America’s tax system is how much it comparatively penalizes those who make a high salary over those who earn by investment gains.

I’m sure some neoliberal could give a polished argument about about marginal tax brackets but we absolutely hose high W2 earners relative to capital.

Maybe Americans aren’t so sophisticated about what this means but it seems folks got the gist of it. Older generations owning the S&P and their home found that to be a better investment than just working for a living.

The message seems to be if you have a salary at least try to be a partner in the company yeah? Thats how bankers, lawyers, and other professionals did it.

This is a very boom boom when it works and gets very ugly when it doesn’t.

I find it odious that we tax high earning labor. It stifles social mobility by keeping wealth out of reach of the professional class. The government decides how their money is invested. That makes it much harder to take the long view. Clearly the generation above us didn’t always do 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.

Categories
Emotional Work Startups

Day 1515 and Hope in the Dark

Given the amount of illness that seems to be plaguing folks this winter I’m surprised we’ve not all decided to hide until Spring thaw.

Every event seems to be a super spreader. Our physical immune systems are shot and I doubt our emotional defenses are much better. Everyone is predicting informational dangers myself included.

It is hard out there and we all experience it in different ways. My medical improvement sprint is plagued with logistical issues, the mold situation in our basement is overwhelming, and yet I have hope that I’ll make it.

o many people are dedicated to building solutions to problems, big and small, that I can’t selfishly let my any of my problems stand in my way. We have to all pull forward together.

I spent a few hours with a portfolio founder working on their fundraise today and I felt my optimism. I enjoyed the flow of work even as the enormous task of raising capital is filled with risk.

I’d taken a risk on directional play earlier in the year. I believe in the founder. They are making their way through YC. I can see their path emerging with every step forward. And I see hope.

Categories
Emotional Work

Day 1513 and Forcing Function

I’ve not in one thousand five hundred and thirteen days of writing in a row set forth a m standard for how I might quit. Four years (or 216 weeks) is plenty of time to come up with a criteria for making a decision.

I have in that time embraced the haziness inherent in self trust. I’ll just know when it’s time. That’s obviously a rationalization. I assumed that circumstances would decide for me which meant I’d never need firm criteria for stopping. It would just happen.

Given my health and the general state of the world surely in this long timeframe some calamity, crisis or mishap would keep me from writing one day and that would simply be that. The chain would be broken.

It has not yet happened. No forcing function has stopped me from my writing practice. And I’ve not yet set worth anything firm about how I’ll know.

So far 2025 has tested me. There are many short posts. I have been hampered by health and home issues which sorely make me want to give up some days.

I’ve tried to included more sporadic “linking and thinking” to make my writing space more blog-like and less essay oriented. Backing away from narrative forms is a fine way of introducing flexibility into one’s writing.

I can’t help wondering if I should introduce a forcing function and create a set of criteria for when I’ll stop. But the truth is I’m scared to give myself a clear way out when I’m struggling. Perhaps it’s better to keep that trust that I’ll know.