Tag: Culture

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Finance Startups

Day 348 and Empathic Investing

The best investor I know is Cyan Banister. When I was coming up in the web2 world I got to watch how Cyan handled early stage relationships. She brought total empathy to every interaction I witnessed. The kind of candor, kindness and willingness help her founders eventually set the template for how I wanted to work. I wanted to invest with my whole self like Cyan.

While I doubt it was the primary motivation or even expected outcome, Cyan’s angel investments are some of the best returning of the generation. If you subscribe to Alex Danco’s theory of social capital and angel investing this kind of investing is playing an infinite game. It clicked for me then that the real edge you can bring to the earliest stages of startups is an open heart. An open heart gives you an open mind. And everything else is a matter of tactics from there.

Creativity comes from seeing something in a completely new light. A change in metaphor can lead to tangible physical discoveries and complete cultural revolutions. Science fiction gave us the tricoder and the internet. Imagination literally helps forge the future. So it’s important if you want to spot the catalyzing “this changed everything” moments that you be open to seeing the world in an entirely new light.

While I obviously have an investment thesis on the macro level events shaping market demands, it’s not practically nearly as helpful in the day to day of investing as just being human. Creation is volatility. It’s not usual for a founder to bounce between terror and euphoria on the same day. Imagine how exhausting that can be when your entire life is always fight or flight and fear or famine.

My only job is to show up for a founder in that moment and accept them for who they are. They need to trust me enough to tell me if they are scared. Trust me enough to share their biggest wildest dreams. It’s a delicate and intimate thing to be there for someone no matter what. But I firmly believe that is what it takes to build something worthwhile. It’s never ever clear from the outset if it will succeed. The only thing we can truly have confidence in is our ability to solve the problems along the way. Chances we’ve seen the tactical playbook and can help you solve those more easily. Many of us come with baked-in operator skills like acquisition or operations. We can teach you that.

While this may all sound utopian, or if you are a bit cynical, even maudlin I assure you this is the most competitive way you can approach investing. If capital is simply a commodity you must infuse your work with real value to compete. If you have a lot of assets under management maybe you can add a lot of services. Large prestige funds with billions in AUM can offer that. But now you have to have bigger deals and surer outcomes so that impacts what you can invest in. Scale impacts outcome in all kinds of practical ways.

If it’s all about the capital then you can be beaten not just by a better term sheet (which just makes everything you do more expensive) but also by someone who brings intangibles to their place on the cap table. You know whose pro-rata doesn’t get cut? The person who showed up day in and day out before the round got competitive and every is kissing ass to get in. The founder remembers. And so does the empathetic capital. We win twice over because our deals are cheaper and we stay in them longer.

So founders and fellow investors ask yourself who you want in your corner from the start. You may find the smartest capital is actually the nicest capital as well.

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Politics Preparedness

Day 346 and Pandemic Inequalities

The last two years have been pretty good for the wealthy and pretty shitty for everyone else. Mostly because when governments slash interest rates and pour in stimulus, it’s the wealthy who can flood into equities and secure loans that make money functionally free. Everyone else has to rely on salaries that are paid in a currency that is being inflated.

I don’t think we are coming back from this widening division. It started before this anyway. The Great Recession and the Global Financial Crisis decoupled a lot. And you can probably blame the rest on Reagan. Hell go back to Nixon and the gold standard. Doesn’t matter. Compound interest and power laws have pretty clear math. The rich get richer.

But I’m somewhat more offended by the cultural chasm that is emerging. The labor class that lives under restrictions and fear while the elite with good passports and wealth move into Dubai apparently.

In a very fine demonstration of the power of public relations, The UAE appears to have placed glowing article in the Wall Street Journal about how Dubai is the new Covid free home of the monied. It’s a fascinating piece of propaganda about freedom to live life and do business. As long as you can afford it. It’s expensive to move to Dubai but once you are there apparently life is back to normal.

Sky high vaccinations and low taxes make Dubai a pandemic boomtown. Open borders and low infections are drawing the wealthy, businesses and tourists.

If you aren’t wealthy enough to pick up and start life over, you are stuck with whatever restrictions your nation places on you. Or conversely, you accept the risks of local transmission, vaccine uptake & political disposition of wherever you live. If you want to travel good luck with things like visas and the expense of quarantines.

I don’t know why this offends me. It’s been clear from the start that some people have had very different pandemics. The middle class has had the benefits of work from home. It’s been the working class that has had to live with all the risk and restrictions. But I do find it a bit upsetting that we are accepting new tiers of global citizenship based simply on your ability to pay to be without Covid cases. Since we can’t end this together I guess we are doomed to escape it on our own with our own abilities.

Categories
Aesthetics

Day 342 and Cosmetics

I’ve barely worn any makeup since the pandemic started. If you knew me in my former life as a cosmetics CEO this might surprise you. But I found that I had mostly worn makeup (also fashion) for other people. I found it fun and enjoyable for social signaling purposes but otherwise didn’t engage in it for personal pleasure.

But today I found myself wanting to wear some eyeshadow. Not a tasteful nude from a basics palette of pressed powder. No I wanted to put on some velvety cream with some shine to it. Maybe even a bit of sparkle.

Initially the desire came over me because I haven’t been able to get a Christmas tree or set up decorations yet as I’ve been immobilized to heal a ligament injury. I thought a little bit of shine would make me feel a bit of the season spirit. I wasn’t going to be able to trim the tree for a bit but I could trim myself in something tinsel colored.

This desire to do something for fun and for myself isn’t something I’m used to. I have a bit of paranoia about using too much energy on something frivolous. Like I’ll regret having had some fun if later I felt too tired for routine obligations like working out or cleaning up. I’ve even been known to put off activities if I know I need to wash my hair and do a big bout of grooming. Laugh all you like,but with chronic pain in my spine bending over to clip and file nails takes it out of me!

So I take it as a good sign that I found the idea of doing something unnecessary and energy intensive like putting on some eyeshadow sounded like fun.

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Emotional Work

Day 340 and Unconscious

I have reached the stage of my recovery process over my ankle injury that I am wondering what unconscious desire did I have to put myself in a position where I’d be reliant on others again. I’d only recently felt fully independent and healthy within the last few months. I had come to consider myself recovered. And yet here I was laid up back in bed.

A lot of folks don’t appreciate the therapeutic process of plumbing one’s unconscious desires. It has an uncomfortable hint of victim blaming to it. If something happened to you, well you must have wanted it somewhere deep inside. That sort of misses the point though. The freedom to become responsible for ourselves is hard work. It is actually much easier to allow ourselves to be a victim of our past patterns and behaviors.

We have to regularly inspect our deeply held emotions and their origins in order to live up to being an adult. Sure we all have wild inner children with deeply felt but entirely irrational reactions. Sometimes those unconscious pieces of ourselves runs the entire show. We might even fear it is the source of our unique genius. But it doesn’t have to be that way. We can appreciate the benefits of our joyful creative wild sides while still being a responsible adult that manages our inner child’s emotions.

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Aesthetics Preparedness

Day 339 and Doomer Optimism

I write a mini-festo for the Doomer Optimism community. I am sharing it here today as well as gosh darn it I wrote it so it counts.

I come from hippie utopian stock. My parents, both working class union types, moved us to the promised land of Silicon Valley right before I was born. The family lore concludes that my father had no job on the day I came into the world as he was pitching a startup. My parents believed in the promise of computing, and eventually, the internet, to connect free thinking humans in a culture of collaboration and self-sufficiency. The do-it-yourself ethos of Stewart Brand’s Whole Earth Catalog combined with a heady blend of technical opportunity and growth that is well chronicled in What The Dormouse Said. This gives you a sense of cultural milieu in which I was raised. The sixties had long given way to the Reagan revolution and the rise of Clinton’s neoliberalism when I came on the scene, but I never forgot my roots. I invest in startups to continue that legacy of autonomy and freedom at my own fund chaotic.capital.

“Remember what the dormouse said: feed your head.”

For me doomer optimism is the continued braiding of those cultural strands. Each one of us is capable of connecting to each other and enabling ourselves, individually and collectively, to lead the life of flourishing and growth we seek. We want tools and information that feed our head but also crucially our heart. The key insight that these very different culture strains, hippie and technology, have shown us, is that individual empowerment is what ultimately connects us to our tribes. 

How does it work? Well, natural law is pretty simple. The laws of thermodynamics are clear.  “If you do not fuck around, you never find out.” As we cede autonomy to others, we cede our capacity to fuck around. The inexorable logic of that, means we also cede our capacity to find out. Without the natural chaos of energetic entropy pushing man against nature, we get stuck. We stagnate in the local maxima. 

And we long to find out. We want to find our communities, our families, our capacities, and our passions. That is how we build. That is how we invent. That is how we solve our problems. Humans are capable of huge creative leaps. Massive shifts in capacity have risen in a blink of an eye. We can solve our problems, and indeed have been doing so, for millennia. But the only way we do is if we fuck around. Otherwise we will never find out what we are capable of overcoming. No matter how dire our problems we can rely on the deep laws of energy. So don’t be afraid, go and fuck around. We are counting on you to find out.

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Emotional Work

Day 338 and Effort

The real world rewards talent. It largely doesn’t give a fuck about effort. Sure, we like it when someone with talent works hard at honing their gifts. But if you just work hard it is largely ignored. The end result still matters most. Talent more easily gets the desired outcome.

This is a sort of hard truth that isn’t particularly hard to grasp. Every bit of evidence you have from a young age indicates that we reward outcome. Even if you are in a school system without grades, like I was, we still know what a quality outcome looks like. But we spend all this time and effort lying to kids with this separate system of effort that suggests that working hard and putting in a lot of effort are the thing “good” kids do.

I’m not wild about praising effort and hard work on its own. Sure it matters, hard work honing your skills, even when you suck, has its own value. But not when it comes to what the world expects of us. We inculcate habits and emotional expectations that are basically cargo cults. No wonder kids, after being praised and rewarded for effort for a decade or two, are confused when they get their first job. I’d be fucking pissed if I were that kid. I’d slowly shaped my behavior around one set of expectations only to find it had no bearing on reality.

Why do we spend so much time cultivating the myth that effort matters as much as talent? Why do we praise effort so consistently among our youth when we know that at a job being told “well you work hard but…” is probably a prelude to being let go. You have to work hard and achieve the desire outcome. It’s enough to drive people nuts. It is literally crazy making to contradict reality with all these lessons on effort. We are gaslighting our youth.

Categories
Media Politics

Day 331 and No Going Back

We were never getting rid of the downstream effects of the pandemic. All the joking about the “before times” was just our collective psyche exhibiting normalcy bias. There is no going back. Inequality is rising and people are struggling and attitudes have ossified. Not because of some bizarre conspiracy but because you can’t put toothpaste back in the tube.

Every restriction and panic is just another day where the world gets more unfair and the prepared and the wealthy have more moves than those at the bottom. And so more people suffer and the gyre widens.

The thing about being privileged is that it compounds over time. Every instance of success and every lucky break build on each other. The math is an inexorable process that leads to one conclusion. The rich get richer.

The reverse is true too. Every barrier, every bill, every setback, every issue compounds too. An object in motion stays in motion.

If this all seems very unfair, I regret to say there is absolutely nothing any individual can do about the physics of success. The best you can do is try to bring others up with you. Educate them on the logic of success and arm them so they can begin to compound their own.

You can’t do it at mass scale. Individual outliers will distort every set of rules and every game within a handful of moves and the accretion of influence begins anew. There is no such thing as revolution. There is only hoping you can enable enough people to change the direction for good. That enough people chose collectively to make better choices for each other.

Anyone who preaches anything other than individuals aiding each other in freedom will have to acknowledge that all systems are prone to corruption and self serving. There is no level playing field.

Some of us just have enough ego to think if it is our people and our tribe or our political party in charge we’d do it better. That’s a lovely lie and history is riddled with the graves of societies that fell to egos of Caesars and strong men. Humans wouldn’t be interesting without our sins. We have to chose to overcome them and accept responsibility for their consequences rather than put our problems at the feet of elites.

And this unfortunate logic can lead one of two ways for America. We can either accept the personal freedom and self responsibility of each other. Or we can get smaller as a nation. What’s more likely to happen is the inequality widens. The rich and productive will write their own destiny. They will take advantage of the sifting sands. New fortunes will be built on pandemic logic and technology.

And the insecurity of the chaos will erode the positions of most fragile members of society and they will fall further as we climb higher. We will force rules on them we don’t abide by. Masks, testing, vaccines, restrictions of movement become for thee but not for me. We will restrict their capacity because it doesn’t affect our lives. It’s corrosive and unequal and cruel. It’s entirely without empathy. And we are accepting that because our stars are rising. The money is being made off this societal transition. It’s already in motion.

Categories
Aesthetics Chronicle

Day 332 and Advent

I don’t talk about it much but I am a Christian. Not the American evangelical type but more of the original reformation Calvinist type. I happened to be taking set theory at the same time as I was reading Calvin’s Institutes of the Christian Religion. God is the set of all sets. Which cannot exist. You probably follow my logic from there. Math and divinity school are a weird mix.

I like routine and rhythm and even seasons. I particularly like holidays and the way we set our calendars by them. The holy nights between Christmas and epiphany are some of the most sacred in my own calendar as I use them for rest and reflection. It’s the space between the in breath and out breath of the year.

Tonight is the first night of advent. It’s the 4th Sunday before Christmas. Advent, from the Latin adventus and the Greek parousia, means arrival or coming. I guess strictly speaking it’s the liturgical calendar’s preparation for the nativity of Christ but also maybe the second coming. Apparently no one knows exactly when Christians decided to celebrate advent (maybe the Council of Tours?), but it seems to involve fasting.

I have an advent wreath and candles. I am ready to celebrate the changing seasons. I like the idea that the end of the year is the beginning of the new one. Beginnings and endings now being so wrapped up in the Christian calendar that we don’t even remember what pagan light festival they replaced. Winter solstice is just a part of the season now. The first Sunday of Advent are coinciding with the first not of Chanukah this year. Festival of lights are aligning this year. I’ll be lighting a lot of candles to see myself into the end of this year.

Categories
Chronic Disease Emotional Work

Day 330 and Vitamin Not Pill

I was reading a fellow investor’s thesis page and noticed one lens they use for investing is whether a product is a “vitamin or a pill” with the insinuation that pills are inherently better investments than vitamins, as one is a nice to have for a business and the other is a must have. Now I can’t speak to this as an investment thesis, though I largely agree, but I do disagree on a wellness basis.

Preventative medicine is just as necessary as interventional medicine. In some cases more so, as getting ahead of a disease’s inflection point should be the humane way we handle our medical needs. We are just often too focused on short term impacts to see the value of solutions that build over time. Think of it as the quarterly reports of healthcare. Why build for the future when the market judges by each 10K?

The nature of panic may make us inclined to spend heavily on something that has become acute. But that does not make it inherently more effective or worthwhile. It’s just the immediately necessary. It just means we need higher minimum effective doses to see a result.

What we often ignore is compounding effects of wellness interventions are far superior to the mitigation of a pharmaceutical over time. Most of us would prefer to not require the costly (both biologically and financially) medicines that keep us together. This is not to say that I am not deeply grateful for all the drugs I take. But rather that I have seen incredible value in what we deem “lifestyle interventions” and other “nice to have” vitamin style supplements and protocols.

And while it takes much longer to see their effects, the compounding positive effects often wildly outperform anything that might be dubbed a pill. The trouble probably boils down to switching costs and time to pay off. Which is why an investor would prefer a pill to a vitamin. But just because something has a longer lifecycle doesn’t make it inherently less sticky. Or less effective. Or crucially any less profitable. The only way we ever see the deeply positive effects of habitual practice and dedication is to do the work. That work is boring, repetitive and low payoff. Until, most times years in the making, you see how putting your future self over your present self is what is giving you the future you always dreamed would be yours.

Categories
Emotional Work

Day 329 and Thanksgiving

I have so much to be thankful for this year. I don’t have a lot of poetic thoughts on it, though I have written extensively about my feelings on some of the bigger moments of the year. So click those if you want essays as this is going to be mostly a list.

I’m grateful to have recovered my health in 2021. I’m equally grateful I had the money, support and willpower to achieve it.

I’m grateful I have a husband who understands me and gives me the love, support and freedom to be me.

I’m grateful for having a space to share my thoughts daily, and rather than be punished for speaking my mind, I am rewarded for it. That includes WordPress, Twitter and all the people who made the internet possible.

I’m grateful I can live in Colorado and still do the same work I previously thought I would only do in New York or San Francisco.

I’m grateful my mother sent me to Waldorf school. I’m grateful I have a father who supported my development as a full human being.

I’m grateful I can afford to buy whatever dumb shit I like for my hobbies which range from expensive skincare to preparedness.

I’m grateful I can consider buying a home that will have the capacity to provide safety even as the world around me has risks.

I’m grateful to have business partners who share my vision for investing and founders and entrepreneurs who allow me to help them.

I’m grateful I never have to worry if there is enough money in the bank to buy a book.

I’m grateful that the supply chains have held so that I have an apple pie that I ordered online the day before the biggest holiday of the year which I picked up in my car that I was able to buy even as global trade was strained and our currency was inflated.

I’m grateful for the time to pursue emotional capacity and the money to pay for it.

I’m grateful for chemistry and the wide variety of pharmaceuticals and supplements that I take every day.

I’m grateful for my iPhone, it’s applications and games I use daily on it that have connected me to a world of people virtually that I love as truly as the people I interact with physically.

I’m grateful for shitposting.

I’m grateful William Gibson still writes. And I’m grateful that Twitter has let me interact with my favorite writers.

I’m grateful for West End BBQ and Spruce Confections.

I’m grateful for my raw milk dairy cooperative and it’s farmer Daphne.

I’m grateful for sunscreen and for apple cider vinegar.

I’m grateful for Costco.

I’m grateful for my parents making good decisions when I was younger that have compounded into incredible luck and prosperity for me.

I’m grateful to be American and I’d like that to remain a thing for which I am grateful.

I’m grateful for democracy, the enlightenment, free elections, a free press and liberalism.