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Emotional Work Startups

Day 785 and Not Overwhelmed

Life feels pretty nonstop for me at the moment. I’ve got three deals I’m working on that are about to go out for fundraising, I’ve got my own fundraising to do, and I’ve got eyes on me from press. Normally this would be a full plate for me but I am taking a trip to celebrate my father’s 80th Birthday this week.

Normally I’d be panicking about packing. And I did have a few little moments of anxiety about getting everything done today. But I’m actually looking forward to the trip even as I have all this professional excitement.

My father loves startups. He just lives for everything about technology. He never missed a Comdex when I was a kid. He still goes to CES even now just to see what might be out there. His enthusiasm for this world is clearly where I got it.

So I think I might be looking forward to bringing all of the energy around chaotic.capital to his birthday. My father wasn’t a particularly demonstrative father but I know he’s really proud of the career I’ve pursued. So it seems fitting that for a celebration of his life and this major milestone that I get to bring some of the world he loves so much with me.

Categories
Startups

Day 761 and Calls

Yesterday ended up being a big day for me. A couple projects that have been in the works for months for final confirmations. That meant I spent a lot of time on phone calls yesterday.

I hadn’t planned for Monday to be so busy. I have therapy in the late afternoons so I tend to back my mornings but I still leave enough breaks to come down from the energy and excitement of a big call. I find synchronized communications to be a little overstimulating so I like to meditate and do Wim Hoff breathing to break down my cortisol levels.

But I couldn’t make it happen yesterday. It was too much back to back. I went from an hour long fact checking media call right into my two hour group therapy session. I’d had a few other smaller calls before it as well.

My earbuds were the first to note the issue. With about fifteen minutes left in my two hour Zoom I got the 10% battery left warning from my AirPods. My technology realized it was time to recharge before I did.

And boy was the decay quick. The AirPods went bwoooop and went dead. I could feel myself getting a little dazed myself. As soon as I was off the call I checked my HRV using Welltory and found all my systems were drained. Too many calls has called on too few resources.

Categories
Background Chronicle

Day 729 and My 22 Round Up

I scrambled a bit to do round up of this year’s posts. I went through through each day individually and attempted to sort posts that grabbed me into succinct categories. I don’t want to call it a “best of” list so much as a set of themes and experiences that made up my 2022. It was quite a year.

The most popular post I wrote this year was my viral hit about dickriders by a huge margin. The tweet got several million views and the blog post got upwards of 50,000 readers. Nothing else even compares. I think my some of my most honest writing came through two days in May when Alex and I decided to buy our house in Montana. Day 499 and 500 respectively. But I cover a huge breadth of topics over the year so without further ado here is the list. In no particular order.

Twitter Shit

Dick Riders or Don’t Outsource Your Credibility

Excession, Nerd Wounds & Needing to Be Liked

Gender Politics.

Mommy Issues, Girlbossing, & Chivalry for Women After Feminism

The Cuckservatives

The Fuck Boys

The Thot Leaders

Startup Content

My #5Before40 Project to Build Chaotic Capital in Public

Managing Founders or The Rule of 3 Asks

How To Do Cold Outreach

Managing Winter As A Metaphor For Downturns

The Importance of Corporate Governance for Startups

Glass Cannons, Gaming & Going Critical In Startup Life

Accidentally Ahead Of The Fraud Trend

Shoot The Puck or Letterkenny as a Metaphor for Startups

Vibe Shifts, Web3 and End Times at EthDenver

High Agency People

How I Sensemake My Investments

Emotional Work

FTX, Crashes, And History Repeating

A Love Letter To My Husband About Chores

Being A Daddy’s Girl

Halfway There or 500 Days

Vinegar or Why Boundaries Are Good

The Emotions of Buying Your First House

The Emotional Security of Owning A Home

A Painting Without Shadows is Flat

A Deep Sense of Okayness

Watching Others Drown

Montana

Bozeman, Boulder and the Uncanny Valley of Progress in The American Mountain West

Hospitality, Guest Rooms & Welcoming

Leaping into Action or How A Wilderness EMT Course Helped Me Work in Chaos.

We’re Not In Colorado Anymore & Our Digital Barn Raising Move

Health & Biohacking

The Personal Politics of America’s Drug War

Aesthetics, Religion and Botox

The Poetry of Migraines & Stretched Time

A Meditation On Heat, Social Mores, Pain, and Texas

Tracker Jacker or When Your Health is Outside The Mean

Politics

Preparedness, Consumer Culture & Distrust

Margin Call & Collapse

Women & Bodily Autonomy, Young Male Reactionaries and Groypers

The Humiliation of America’s Broken Immigration System

Categories
Emotional Work Startups

Day 719 and Step By Step

I was discussing my goals for 2023 with a friend today. They wanted to know if I was planning on making any New Year’s resolutions. I told them that I wasn’t in the habit of using a new calendar year for making big changes.

Generally speaking if I want to do a thing I just start. I honestly feel like it’s far too intimidating to declare yourself to be some kind of fundamentally new person that will, as of a certain arbitrary day, make huge life changes. It’s too much pressure. One of my rules for biohacking is to only change one variable at a time. And I don’t make big changes to it either. 10% a week is good enough for most goals. Anyone familiar with the magic of compounding knows that small changes add up to big numbers.

Which isn’t to say that I haven’t started big life changing projects on January first. If you count back from 719 you will notice I first began writing on January 1st 2021. I did indeed resolve to write every day. But I hadn’t intended it as something I’d keep up for a specific amount of time. I’d hoped I’d practice my writing for thirty days and I allowed myself a little fantasy about how amazing it would be to write for a thousand days.

A thousand days seemed like an impossibility at the time which is why I allowed the fantasizing. My pragmatic side said just get started and see if you can keep going. And I did. I put one foot in front of the proverbial other for two years. Now I’m relatively confident that if I want to do so I’ll make it to a thousand days.

I approach most goals like this. I had a fantasy that I could make it as an investor. I was a founder so I thought let’s wire some small angel checks. We were already committed as a family to being startup operators so why not combine our skin in the game with a little more capital risk with our network.

I never envisioned myself raising a fund and making some big announcement about how I had a venture fund. I just started learning by doing. I cut checks. I ran some special purpose vehicles. And this year I decided to one-step-at-a-time go about raising a rolling fund. I am just doing the thing one day at a time. And it’s going well. Amazing people are coming on board. I am confident I’ll reach my goals just by putting one step in front of the other.

If you’d like to join me my goal is to raise $500K per quarter. I’ve got folks like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company. You can read the fund overview here. Yoican sign up on Angellist through the above link or get on a call with me and we can discuss the fund, our portfolio construction and my thesis. Because I intend to work through the holidays because it remains one day at a time.

Categories
Internet Culture

Day 717 and Walled Garden

The walled garden debate is back in Silicon Valley. What is a walled garden you ask? It’s a closed ecosystem in which your entry, exit and experience in the garden are controlled by a central entity. While modern social media has very centralized ownership structures, we’ve basically aligned on allowing sharing of content and interactions across and between platforms. We’ve homestead the modern social internet by tilling our profiles and tending our communities.

But people are straining at the compromises we’ve made over the years. Elon Musk is attempting a rather heavy handed walled garden strategy on Twitter by banning linking and promotion of competing websites.

It’s unclear if it will last at the moment as within hours Elon apologized for making a massive change without a vote. Whatever that means. It’s been six hours of chaos as people reactively extremely negative to being told you cannot link to your Instagram or Facebook accounts. A few dickriders attempted to defend it by saying it was freeloading but it isn’t really tragedy of the commons that Twitter can’t make money off my hard work.

I’m old enough to remember the sheer indignation of Linux dorks had for the all encompassing closed systems that is Apple. Jailbreaking was a pastime for a whole generation of nerds. Sure the money folks kept trying to contain their ecosystems giving us nonsense like America Online, but information wanted to be free right? Well Stewart Brand fans know that isn’t the whole quote

Information Wants To Be Free. Information also wants to be expensive. Information wants to be free because it has become so cheap to distribute, copy, and recombine—too cheap to meter. It wants to be expensive because it can be immeasurably valuable to the recipient. That tension will not go away. It leads to endless wrenching debate about price, copyright, ‘intellectual property’, the moral rightness of casual distribution, because each round of new devices makes the tension worse, not better.

Stewart Brand Whole Earth Catalog

Whatever is going on inside Twitter and Elon Musk’s mind is unclear. But the basic tension of the internet has not changed. We built tools to network together whole worlds and that has been fucking with ideas of ownership and who gets paid since day one. Capitalism usually finds a way to ride on top of these issues of ownership and value but the technological progress came out space old norms quite quickly.

And we are in a moment where skepticism of these norms is being challenged. Why shouldn’t we get to chose how we engage with our own property online? Maybe we don’t own the land but we definitely homestead our little plots of internet land.

Because the nature of the internet is wild and untamed. It takes work to make it usable. And most of us don’t mind paying a fee to keep the grass trimmed. A few of us might even prefer a country club experience. But the trouble with any commons starts when enclosure starts.

And Elon seems to be going for something that’s more heavy handed HOA than parcel of land outside of county lines. And like your average president of the homeowners association, he seems to be taking concerns and criticisms quite personally.

Categories
Internet Culture

Day 716 and Slightly Embarrassed

I spent my entire day on Twitter. I’m not embarrassed by that to be clear. It felt like a vacation day. And even though I live in a majestic mountain paradise, I will spend my time off inside looking at my phone.

Yes it was absolutely gorgeous day in Montana. I marveled at the playful pinks of the sunrise over the mountains in our backyard while drinking coffee. And then I got back in bed and on my phone. And you better believe I fucking doomacrolled.

I just gorged myself on cheap attention calories. Gimme that dopamine drip. I did not even try to modulate my consumption pattern or prevent myself from going into fight or flight. It was goblin mode. I’m still not embarrassed.

But Twitter is a fucking mess. Watching people go tribal on Elon Musk is worse than people going tribal on the president somehow. Maybe because it feels more personal to me? Don’t get me wrong Trump felt existential, but Elon Musk is personal.

And it’s fucking embarrassing watching people react to him and his decision making. Here it is my industry’s moment in the spotlight. The technology industry showing itself as a keeper of common goods and open discourse right? Absolutely fucking not. We’ve shat the bed. Old management was incompetent sure. But new management is not an improvement.

I went into Twitter being purchased by Elon Musk modestly optimistic. He’s our guy right? He’s one of us. He likes startups and capital and technology. He reads the same science fiction as me. We’ve got friends in common. This is what it’s like to be a fan of the home team right?

Well fuck me sideways it has been going poorly. The site is pretty broken but I’m over that. It’s just the constant mayhem. Dave Kellog termed it adhocracy. Some random bullshit happens and the whole website has to lurch around conspiracy theories and rationalization.

It has frankly not been a fine showing for techno-libertarians. Not sure about showing up for a monarch executive now that you’ve seen your civil rights up for terms-of-service revisions by fiat huh? I’ve always thought the neo-monarchists to be dickriders but that’s a sentence that’s only comprehensible to the terminally online. And yes I should go outside and touch snow. I’ll do that now.

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Aesthetics Startups

Day 714 and Cosmetic Organization

I used to be the CEO of a cosmetics company called Stowaway. We were a direct to consumer brand that manufactured and retailed our own line of travel sized makeup. Alas I got too sick to work and we sold the company to a private equity holding firm who shuttered it during the pandemic. I’m “shocked” that travel sized red lipstick wasn’t popular during two years of masking and lockdown.

I don’t particularly want to work in cosmetics again, even though I have arguably priceless experience that could be put to good use helping other brands. Startups are are traumatic and it’s not unusual for founders to find it challenging to work in spaces they know well. You don’t want to undermine the enthusiasm of founders. Also you’ve probably taken enough risks for a lifetime in a given space to never want to touch it again even if you made money.

But I do still enjoy being a consumer of cosmetics. I’ve got what might be the most comprehensive library of travel sized makeup in existence. I moved all of it up to Montana this year where it lives in a modestly organized vanity. For some reason I decided do a little reorganization of it today.

A very messy cosmetics vanity littered with makeup bags, travel sized packaging and a Sephora advent calendar.

Instead of finding a new schema for where I plan to keep all my products, I made it much worse. I let myself get a little bit of tunnel vision and instead of playing around for half an hour I spent an ungodly amount of time making it much worse. I’ve got drawers that are bursting with tiny mascaras, tiny lipsticks, tiny eye shadow palettes and thousands of other items.

I was surprised to find myself enjoying it. I did some comparisons of packaging and formulations and found that I was still quite pleased with what we had built. Many new brands have emerged since then but the promise of a minimalist purse friendly brand remains elusive. I see all the ways I failed but I also saw all the ways in which our team succeeded. And it was nice to feel like perhaps I’d learned something. But now I’ve got to clean it all up before my husband steps on an eyeliner.

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Aesthetics

Day 705 and Impressed

I haven’t bought a new handbag for nearly a decade. While I like fashion I have never been a hardcore accessories person. One generally been of the mind that those are anchor pieces that you keep for years and years. I didn’t see much point in acquiring trends as it just seemed so expensive. I buy more for longevity.

The last handbag I bought was a camel Masur Gavriel bag. I think it was sometime in 2013 but it may have been earlier. I found a photograph dating it no later than 2014 but I can’t be sure. I’d seen a small piece of press about it as it being a kind of super minimalist brand by these two bicoastal pretty girls. I loved the clean look of the tote with a long full leather panel and a bright yellow sunny interior. I found a boutique that stocked it in Los Angeles. I think I paid less than $300 for it.

I’d talked it up to a girlfriend in finance and she bought one. She then talked it up to her friend who happened to be Lauren Santo Domingo and then next thing I knew the nag was absolutely everywhere. It subsequently raided a large private equity round. It’s brand book became so popular a fast casual yuppie food brand called Digg Inn ripped them off. The brand was a genuine hit.

Being ahead on a handbag like that is the fashion equivalent of being in the best series A round in Silicon Valley as the new angel investor. It means a lot but only after it’s been proven out to the IPO. I haven’t felt that kind of kinship with a brand in a while. And certainly not with a handbag. The high conviction I had with Mansur Gavriel should have made me pursue the two designers as I just knew in my gut this bag was fucking it. Really the one that got away for me.

So I am excited that I got a new handbag today. The first one I have purchased since my Mansur camel tote. I’ve literally not purchased a single handbag in that entire time though I did buy a backpack and a suitcase.

I saw this across it across a bunch of fashion blogs over the year. It has hit a lot of mainstream fashion news. So fashionistas are definitely well and truly ahead of me. I am not a market editor or an influencer being sold by fifteen different publicity firms. Though I’d absolutely like to be. There was absolutely a time when I was very much in the scene but let’s be real now I’m an eccentric investor in Montana. I’m cool just in a different way.

Polène Numero Uno Mini in Black Lizard with dust bag.

The bag is called Numero Uno Mini from a French label called Polène. It’s a clean bag. But it’s got a little personality in it’s shape. There were smooth calfskin options but I’d been searching for a modestly dressier bag that would be a bit of a statement for day but also formal enough it could accompany a cocktail dress or make due at a wedding. It works up until you need a clutch because it’s a gala or an awards ceremony.

Polène Numero Uno Mini in Black Lizard with dust bag.

I feel like it’s a bit louder than the bag it’s replacing which was a black calfskin envelope clutch with a gold chain that is bought from Barney’s. I’d got it on sale for like $150 bucks as well it was a house brand I guess. But it was just so damn versatile I used the fuck out of it. I haven’t seen it since we moved to Montana and I’m a bit concerned it’s gone for good. So perhaps this new Mini will find a home in my routine.

I’m very impressed by its quality. The stitching is tight and lean. The hardware is bright and sturdy. The logo is very discretely etched into corners of the hardware and on the feet of the bag. Which is just a nice touch at a $350 price point. Recently it’s felt like everything is a bit shittier and more expensive. So it’s a joy to get something that feels like a great value and genuinely nice. I hadn’t made some dirty compromises with a direct to consumer business. So yeah I’m impressed with a handbag.

Categories
Culture

Day 700 and Focus

I’m noticing a latent fear in the startup management classes. How do we know if people are focused? Maybe it started with work from home skepticism. But now it’s become an all encompassing yet amorphous fear that nobody is focused anymore. And I have a theory.

It’s all projection. The fear is coming from inside the house. The world is so chaotic everyone is struggling to stay focused. This includes your manager. This includes your manager’s manager. Even your CEO is struggling to shake off the clinging entropy that emerges from constant crisis. And because shit rolls downhill everyone is now flailing around attempting to show they are doing their jobs even as they know they are failing. Even though it remains unsaid because it’s impolite to tell your boss he can’t focus.

The constant chaos that is tugging on our collective capacity to focus is quickly eroding our entire social contract. Not because no one does their jobs anymore. But because we want to be set up to succeed. Because “doing your job” is a point of pride for most people. We like to reliable even if we know there are limits to what we can deliver. So collectively we are hyper vigilant for fraud even as we lack all accountability to each other because we’ve got to protect ourselves first. Self care right?

I don’t see how we get out of this state of fight or flight without a significant changes to culture. Surveillance capitalism isn’t very effective at driving value. It is very good at exacting any drops of it from people attempting to maintain their own dignity. See for instance the railroad workers who have no flexibility in their scheduling. Now with added Congressional oversight!

Categories
Culture

Day 697 and Chivalry for Women

I was having a conversation with one of my girlfriends today about power. We are both exploring the new ways in which we’ve become more aware of our inherent power. Not that we were not powerful when we were younger but rather we have a new consciousness about it’s responsibilities. And it’s relationship to our gender is complicated.

One of the most dehumanizing aspects of Girlboss culture was how it forced female founders into rigid standards of acceptable behavior and emotions. We were surprisingly heavily policed even though we were allowed to use femininity to allure and entice. Girlbosses were empowered. Except occasionally we were only empowered with sex appeal.

Girlbosses looked good on magazine covers and in lifestyle content. It was honestly suffocating even as it was a massive tactical advantage. Imagine being given a cheat code or a level up. Of course you are going to play it but sometimes it takes the joy out of the game.

I am less adverse to the wiles of the feminine as I get older. Now I am able to wield the benefits of mutual viewpoints and seeking common ground. Women are trained to persuade from a young age. We are trained to be accommodating and without hostility or anger. It makes it easier for us to seek out where we might come together.

But those powers of persuasion can also feel manipulative and narcissistic. Men who have felt failed by their mothers can feel particularly hostile towards feminine power. Negative family orientations towards women from siblings to parents can sit in completely irrational and reactionary places for men. I say this because men occupy a similar place for me. Mommy and Daddy Issues can often materialize in stabilizing coping mechanisms. But ultimately it’s not a healthy exchange of power if it’s not consensual.

I dislike having power that I only wield because of my gender. I would prefer to have a less charged environment to pursue my fortunes. But I am also not adverse to playing my hand. You’ve got to play it as it lays. Different women have resolved these power discrepancies in wildly disparate ways. But we are not absolved of the ways in which we hurt men just because we have been hurt by them.

One of the great oversights of the feminist movements may be our lack of a developed gentlemanly style code for women. A theory of chivalry for not playing fair in the gender wars. We certainly expected it of men. If you wield power you must do it responsibly. Peter Parker principle applies to anyone with gifts that can be used for good or evil.