Category: Startups

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Startups

Day 840 and Do You Believe in Magic?

The glory of writing every single day is you start to build m records of your own life. You notice how much your own personal cultural history is syncretic. I’ll always be a fan of blogging because it’s got chronology at its heart. Sometimes it’s good to see how we evolved over time.

Having a written record is hard and often dangerous. You own a lot of work in progress that doesn’t necessarily reflect where you landed. And internet opposition research is fantastic at catching you in a former evolution. We call it getting cancelled. But if you get it right you have the receipts.

But if you are an honest broker of your bets you will admit when you get better and more complete information. The real magic of startups is that markets are often excellent teachers of how we are just dead wrong. And if we listen to what we are told we can adjust. And as the old saying goes the market can be irrational longer than you can be solvent. The reverse is true too.

Consensus reality is a bit magical. I called our fund chaotic because the process of getting people to align is magical but it’s chaotic as fuck. It’s studied but experimental. It relies on rules and the temerity to break them. It’s chaos magic. I wanted people to see a bit of the woo woo in our fund name every day. Technology and magic are just separated by layers of abstraction. Go read Charles Stross.

So I was overcome with delight when I saw Geoff Lewis discuss how startups are magical. An all time delightful addition to the genre of how does venture capital and startup growth even work? Fred Wilson blogged so Geoff Lewis could vlog. And he did it with verve while discussing Dungeons and Dragons stats. Also he’s team maxed charisma like me so I am inclined to like him.

The fun part is that he and I don’t really overlap except on Twitter. We’ve never discussed any of this. But our syncretic workflows had overlapped. It felt like a small ecosystem knitting moment. An alignment of metaphors and aesthetics. It made me feel damned optimistic and yes I do believe in magic. And I hope you do too.

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Startups

Day 826 and Alignment

I think there is this persistent fantasy in startup life that people will always agree with your bets. We forget the discord of every hype cycle but it’s not always clear who is winning and what outcome is certain. Only hindsight is 20/20.

You do get occasional moments of vindication but it’s rare that they ever clearly overlap with a trend or a moment that everyone is paying attention. Media hype cycles and innovation hype cycles are not the same thing. Trust me I’m a pretty good publicist for a hobby.

Your deals aren’t always going to get attention though and a lot of founders want to keep things quiet so you can’t always talk your commitments.

This is a problem that investing has in common with fashion. I earned my stripes making shit cool for money. It’s actually hard. I call it the The Thursday Styles. The problem with tend forecasting is knowing what’s going to be trendy is a temporal bet as well as a cultural adoption one.

It’s a thing happening over time that is unevenly distributed. I learned that from William Gibson. Some of us live in the future but you can’t be too far out because then it’s just you speculating. You got to be right on the thing and on the timing to make any money.

It’s honestly way harder than it looks and anyone who is any good at taking a bet on what the future looks like has to take some variant of this bet. It’s probably why Dune is such a canonical text for nerds. He predicts the future dimly and is also a messiah time lord? Sign me up that sounds like venture capital to me. The sheer hubris of this comparison is honestly nauseating.

Like fuck all the way off you ain’t Maud’Dib. You’ve got to be very skeptical about the charismatic pull of a messiah my friends. That said I bet you’d believe me if I told you I was a Bene Geserit right? Anyways. My point is you don’t always get it right and you don’t usually get to take credit till the end. And mercenaries can co-opt anything. Your shit might hit the skids.

But sometimes one of your deals looks hot and everyone is paying attention and you get to feel like you were cool. You spotted the band. You saw the runway show. The media is hyped about it at the same time and your friends noticed on Twitter. It’s a nice feeling. And yes I invested in the Chroma seed round. I think Jeff and Anton are cool.

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Emotional Work Startups

Day 825 and Papered

A bunch of stuff that has been in the works for me for a while all got papered in the last couple of days. If you read any of my zen poasting (misspelled for internet reasons) you’ve probably gleaned that I’ve had a lot going on. Stuff got resolved on time horizons as long as lifetimes and as short as a narrative cycle.

I’d like to celebrate some of the papering (two deals I worked particularly hard for over a long time horizon) and I’m sure I will do so at some point but everything is going by fast and I’m just so drained from the dance. I suppose it’s how you really know if you are living. It’s a lot to live through everyone’s ego death drives and I’d be lying if I said it didn’t take a huge toll on me. I don’t yet know how to pay these costs in anyway but energy yet but I’m learning. If I put hard costs on it motherfuckers wouldn’t like the bill.

I’m modestly less sympathetic to everyone else’s bullshit as someone in my extended family passed away (not getting into it as it’s not my loss) and that invariably makes every other problem look inconsequential. Who care about your feelings and your ego and your petty obsessions in the face of death. But also maybe you should care about them even more? Not my call to be honest.

I’m not really able to mourn with them directly but I feel the energy of the loss reverberating for my loved one. And I wish I didn’t want to discuss it at all but I do. Somehow death is the lowest drama aspect of my week. Actual death.

So if everyone else can tone the energy down a little I’d appreciate it. I will absolutely make sure shit is inked, wired, soothed, smoothed and otherwise handled. It will all get papered. Whether it gets celebrated or mourned is a matter of personal discretion and I’m all out of fucks as to what you chose. Just gimme a beat or two to breath. This isn’t what you’d call a nine to five job.

Categories
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.