Category: Startups

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Finance Startups

Day 820 and Ripped Off

I like doing favors because I don’t care for being overly transactional. I’d rather cultivate something over time to build trust than put a firm price and set of boundaries on what I’ll deliver up front.

And I’d prefer a similar stance from you. Intangibles are hard to price and I’d usually prefer a little time before I settle on them. It’s a trust thing. Everyone gets a fairer deal that way and I only do business if I think it’s win-win.

But once I trust you I generally assume that you won’t fuck me over because I’ve shown that I won’t fuck you over. I’ll value your resources as my own. And I expect you to value my resources similarly.

It sounds a bit old school but I believe we should respect people’s unique styles and contributions. Doing so requires trust and delicacy. We must believe others use us well and we shall use them well.

I find this trust necessary because if I do business with you I’ll use my social capital. Because spending social capital is what gets things done. You make think it’s money, but I can assure you fiat is just a convenience.

Capitalism’s wheels are greased by social capital. If there is too much tension in the system you will never achieve the necessary momentum with only one type of capital. The money is just a stand in for trust. It’s one reason some parties yearn for trustless systems. Because everyone is setting different prices for different currencies and no one likes getting scalped on a forex favor trade. It’s a dick move to undercut social capital.

I’ve found crypto people are some of the worst at understanding this basic social rule as they are the ones most desperate to make all markets legible. The indignation you see across much of technical cultures in general is dismissal of forms of capital that are harder to make legible.

I recently felt ripped off by a transaction I thought I’d priced appropriately to an incentive alignment. It turned out the other side of the deal didn’t have the same understanding of the intangibles. It made me feel like they don’t value my time and work. They’d asked for something, I trusted someone, and then another actor they had vetted spent it in such a careless way I was briefly incensed.

Now you can argue it’s my problem. I priced it wrong. And I had pricing signals coming in negatively from everywhere. I told my counter part this and they took it in stride. And then they went and demonstrated to me exactly why I was getting negative signaling. So I know it’s a risky use of social capital.

Now I’m not sure if it’s a bad trade yet. Maybe I have the tolerance for the volatility. But I’d be remiss if I didn’t look at what the numbers were telling me. Someone ripped me off. Reality says it’s probably just as much me as it was them. Which is, I believe, what you call a lose lose. And that means I’ve got to change the odds if I want to run the trade. But it’s hard to justify it to yourself after you feel like you got ripped off.

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Startups

Day 817 and RIP SVB

I hadn’t expected to grieve the death of a bank. It sounds so preposterous. Who the fuck feels sad about a bank failing? But I am genuinely sad that the Silicon Valley Bank name doesn’t appear be living on with its new owner First Citizens Bank.

I guess I look forward to banking with First Citizen. They seem like nice enough folks. And maybe a bank is just a bank. But as I look back on the firsts that Silicon Valley Bank gave me I realize I will miss it. I’m sad they are gone.

The first check I saw with more than one comma was from Silicon Valley Bank. My very first company was acquired by a startup that banked with them. Ironically, right before the 2008 crisis was beginning to come onto the scene. I had a small window of fleeting security where I enjoyed a steady paycheck every two weeks with payroll done by Silicon Valley Bank. I remember thinking I was so rich. Even though I was super pissed my cofounder had a better salary than me as Silicon Valley culture dictated at the time that engineers make more.

If you are a fan of history then you will enjoy knowing that yes I did get fired during the infamous RIP good times affair. Thanks Sequoia! They were our main investors. Still I appreciated the opportunities as I was so young I wasn’t very good yet. I’ll forever have loyalty to my CEO for having treated me much better than I thought I deserved.

I also I also really loved the steady paychecks from Silicon Valley Bank. Now I think to myself why didn’t I take any pictures of it? Why don’t I have that moment recorded anywhere but my memory? Why am I now recounting this fifteen years later.

I’ll never get another check from Silicon Valley Bank again. I just didn’t have the expectations in life that I’d be the sort of person with a bank account with more than a million dollars. Let alone that I’d be in control of one and entrusted to do something responsible with it. Which has now happened multiple times at Silicon Valley bank over the years for me. Guess no one wants to have more than $250,000 in a bank right now though huh?

So goodbye Silicon Valley Bank. I’m so sad I’ve got nothing to remember you but. I didn’t take a screen shot of the bank app on the day Stowaway’s first round closed but I should have. I spent a lot of time in their banking application over the years running my cosmetics startups P&L. I remember being so proud to be the sort of person that even needed to deal with the bank. And I trusted Silicon Valley Bank with my employees because I’d seen it treat me well when I was an employee.

It seems so silly to mourn not taking a picture of a check or a screen shot of a mobile banking app but I don’t really know how to mourn a bank that failed. We failed them. They failed us. And it’s dead and I’ll never ever get a chance to do it all over again, and even if they are a villain, I remember when they were the hero in my life.

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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 Preparedness Startups

Day 799 and Black Friday

I suppose it’s now quite clear why I felt like I was driving through a snowblind yesterday. For someone who spent the year telling everyone to watch Margin Call you’d think I’d be pretty prepared for the inevitability of pricing affecting risk.

I am, of course, discussing the collapse of Silicon Valley Bank. We’d discussed in our household scenario planning around what would happen if we saw banks forced to compete on better interest rates. Perhaps the same old story of mis-pricing your risk would play out. Discussions of contingency planning and multiple accounts and insurance policies both personal and professional. I really didn’t expect for any of the emergency use cases to manifest as to even contemplate it is simply too horrifying.

But horrible things happen every day and I am skeptical of my capacity to judge my own need for a comfort in a situation in which there is none to be found. I do however believe that in the wake of the Great Recession we’ve come to believe that money always gets bailed out. And why would Janet Yellen (of all people) hang out the singular shining star industry that keeps the lights on in the hollowed out shell of post-industrial American capitalism.

That said humans have been known to do spitefully stupid things that hurt themselves so long as it also hurts someone they dislike. Cut off your nose to spite your face. I don’t know if the drive for vengeance is strong enough for some populist reactionary spill over. I’d want to at least offer up a scapegoat and I’ll be curious to see who has this fate.

This seems like the crumbles to me. The logic of the Jankening is that we cannot always predict the downstream effects because this is a complex system. All I know is that to let a large chunk of the wider technology ecosystem fail would be catastrophic.

However, we have now effectively put in the minds of a new generation that banks do stupidly silly things occasionally (Lmao) and you have to be careful who you trust with risk. Everyone is running to the big banks and that will have its own consequences. I am curious to see what the downstream consequences will be.

Be careful who you trust, use some common sense and don’t be overly sure of the value of powerful people telling you want to think. They might not have your best interest at heart.

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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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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.