Tag: Startups

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Startups

Day 816 and S Tier

I fancy myself as someone who enjoys playing games. I mostly play the great game but I enjoy a good stupid grinder. Pokémon Go, Duolingo, and Fitocracy all appeal to my sense of hard work mattering.

But, of course, games have exploits. Some of them are significant. Sometimes leveling up is just a matter of getting lucky. A side quest dropped you an s tier item and the game engine smiled on you. Yay!

Silicon Valley mistakes luck for skill pretty regularly. And we don’t take it that well when other people use the same exploits as us because damn it that’s just not fair!

So rules tend to get rewritten and the hacks get patched and the economy in grinder games reliably defaults back to rewarding repetitive work. It’s not that different from the real economy. Gamers want to know clever game play works but not as much as they want to keep the value of what they have earned. It’s a real tension those sunk costs! Even if starting over benefits you the tendency to cling is understandable.

You’ve got to know when to spot when an activity is worth more than the general perception. You used to have to do this sort of work on your own but thanks to the internet we’ve got cheat codes literally everywhere for everything.

Don’t confuse the fact that cheat codes work for the fact that grinding came be the right approach for the game you are playing. Sometimes putting in the work means being a team player is valuable. Sometimes you are the glass cannon. Sometimes your style of play will offend others. Don’t take it all so seriously that you cannot stomach making a move. What’s the worst thing that happens?

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Internet Culture Media Startups

Day 815 and Kayfabe

Here is a mindfuck for you. Pretending works. The mimicry of the thing occasionally, though not mostly, can lead to having the real thing. Fake it till you make it” works if you’ve got a long enough runway to allow for take off. If you’ve judged the resources correctly is more art than science but you should still be able to do the math.

There are, of course, laws of physics to account for in all of this but your reality is more fungible than you realize. I wouldn’t try manifesting a whole fantasy world, but if you are Brandon Sanderson you might have a shot. That guy rocks.

In discussing whether it is better to fire founders or product managers on Twitter today I got to see a lot of the cargo cult culture of Silicon Valley coming off a high. A lot of people can perform innovation and we’ve maybe even got it down to being well liked by financial markets. But sometimes you actually do have to go and do the thing. And you can’t fake it.

If you aren’t familiar with kayfabe, it’s a term used in wrestling. It means you don’t break character loosely. You keep the secret even if everyone is in on it. You can take things a bit too far and the blending of fiction and reality has now given us a reality tv president.

But what happens when you don’t make the jump? Does reality crash in? Will the market punish you for not delivering on a convincing enough value proposition? Do you have to keep your ambition within some scope that can exist in our agreed upon reality? Yes of course. Fuck you it’s called civilization. But every once in a while someone goes from vapor ware to the Revolution. Don’t be so sure you can spot the difference though. Kayfabe doesn’t just fool rubes.

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Startups

Day 814 and Odd Hours

I’m a little bit of a work fetishist. I’m into shit like routines and the Protestant work ethic and I avidly participated in hustle culture. But I regret to inform you that most of it is a lie.

So much of your professional life ends up getting wasted to slavish gestures to productivity porn. It’s just not how real life works. But it sure looks sexy when you lay it out like an Instagram reel.

But maybe it’s not always just for show. Maybe there is something you don’t understand about how things do or don’t work. So you accept some social norms to fit in with others and you find their advice on shit like sleep more and get high quality protein is sort of first principles.

You have the basics of being a responsible adult and learning from others while you do it. We have a grand shared culture and some of it is useful and some of it is superstition and sometimes it’s not clear which is which. But shared meaning is how humans organize. Maybe there is value to meetings.

Point my dear whacky zoomer autists is you need to be able to be a functioning member of civilization despite what Covid may have revealed. You have to accommodate other people’s lives even if you don’t like everything. Welcome to the herd.

And honestly you should have to learn to fit in a bit of life that overlaps with real humans. Even though we have total access to our most niche nerd fandoms online, we deal with normies in real life.

But I’ve also come to realize that performance is a game. And you can train yourself to go from zero to halfway decent if you just make an effort. But the real art of it all the tip and tricks and how-to guides comes down to just doing the work and figuring it out. The intangibles make you an expert. That’s the stuff you spend a life refining and it doesn’t ever take a break. It’s why all the super successful people are also kind of fuck ups.

Sometimes the weird is genuine as they have rethought a an assumption about the world and intend to make their vision known in the world. And that’s not done on bankers hours.

I work on Sunday when something happens and the momentum shifts and you know that adding your gravity to the matter could make a difference. And so you go the extra mile for someone else because it’s about us trusting each other to work with reality but also see each other as we are. And most of us are weird and it’s fine and you’ve got to work the way to makes your weird shine.

If you are good at your niche and you apply your knowledge and tell it straight then sometimes you do some magic and it moves your universe. So yeah sometimes you’ve got to keep weird hours to hold space for the possibility.

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Politics

Day 801 and Not Today

It’s been a rocky few days watching the crisis unfolding around Silicon Valley Bank and what would happen to its depositors. We’ve received our answer.

After receiving a recommendation from the boards of the FDIC and the Federal Reserve, and consulting with the President, Secretary Yellen approved actions enabling the FDIC to complete its resolution of Silicon Valley Bank, Santa Clara, California, in a manner that fully protects all depositors. Depositors will have access to all of their money starting Monday, March 13. No losses associated with the resolution of Silicon Valley Bank will be borne by the taxpayer.

So that’s been a wild and scary ride and I guess we are kicking the can down the road. But I wasn’t emotionally prepared for a contagion on Monday.

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Finance Politics Preparedness

Day 800 and Small Potatoes

It’s nice when a round number crops up in my daily journey of writing every single day. It’s even better when it’s colliding with the wider narratives of humans. If you aren’t paying attention to the news, Silicon Valley bank had a run on Thursday and was taken over by FDIC on Friday. Now the powers that be decide our fates. On day 800 we wait to see if anything has changed about capitalism.

I’m small potatoes so I’m scrambling for survival as much as anyone. But I’ve got a reasonably good head on me and I’ve seen this movie before. Literally. I watched Margin Call a dozen times this year. My family also went bankrupt in the 2001 crash and I was working in startup land during the 2008 crash. So this isn’t exactly my first ride on the roller coaster. I still get sick to my stomach though.

I think we are all about to have a significant conversation in America about trust and who is looking out for whom. I have my theories on how it plays out and over what time horizon. Very few of those scenarios and involves actually letting the american economy implode. But some heads will need to roll it’s just going to depend on the fates.

I really don’t feel like writing through some of this as it’s both personally traumatic because I’m a human being but also because I don’t know where this lands any more than you do. A lot depends on who blinks and who we want to scapegoat and how much we want to tolerate the unpleasant realities of who matters most. Not to be dramatic but every empire rests on a pile of skulls. It’s the degree to which this is literally true that changes over the years.

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Emotional Work Startups

Day 792 and Level Ups

I know I am courting a bit of a crash tomorrow because I can feel just how much energy this week took. But I am feeling emotionally like I leveled up. I looked at a few of my emotional patterns this week pretty head on and redrew some boundaries. And this always improves my work performance.

The upside of journaling your thoughts and emotions is you have a back catalog of your own thoughts to compare against your eventual conclusions. You can look back and spot patters in your thinking and tie them together. Writing everyday can be excruciating but I never regret having done it.

I have to always remind myself that it takes a fair amount of effort and a high tolerance for being wrong in public. You have to get used to people disliking you and finding you distasteful. People want to put their emotional response onto you and the hard work of being an adult is not accepting what isn’t yours.

If you can tie that kind of self reflection into your professional life you get all kinds of unexpected level ups. You tell people about your own responsibilities and they trust you with theirs. You get to build great things together by building on shares humanity. The best business relationships I have are the ones where we understand what value each of our personal lives brings to counteracting of own limitations and blind spots. I’ll always work with someone who leads with their humanity first. Big visions get worked out together by trusting each others talents.

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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.

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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.

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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.