Tag: Investing

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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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Homesteading Politics Preparedness Uncategorized

Day 783 and The Alliance

Yesterday was a bit of a busy day for me. A splashy wandering “state of culture in America” piece in a glossy cultural firmament like Vanity Fair is the ultimate validation of one’s thesis. I am taking a little bit of a bow on it. I’ve been on about this chaotic future and here are my receipts.

And it’s potentially a good thing that so many people are seeing the alignment that a muddy middle ground of chaos means “the rest of us” have to get on with building whatever the chaotic future looks like. We’ve got families, jobs, and health problems. Life goes on even during times of contested authority. Honestly it’s usually where fortunes are made.

Because it’s a surprisingly large cultural alliance. It has a key truly America things in common. That thing? It’s the most American a shared value as I can imagine. We believe the frontier can be tamed and that civilization is a good thing. Americans have always had a pragmatic streak to them thanks to our Protestant work ethic fetish.

“Preppers, techies, hippies, and yuppies are converging on the American West, the safest place to “exit” a society gone haywire.”

The Dissident Fringe

Because look, nobody asked for a million stupid cultural schisms and endless battles over basic human rights and who shares in the spoils of civilization. Just find a damn common ground. Because right now we’ve got problems to fix. Nobody is sharing in anything unless we build shit. Building shit is the beginning of shared prosperity.

If we cannot align on that fact, then yes of course we are going to continue fighting in the grey zone politics of civilizational values. Because you know what progressives have going for them? A shared legal framework on which to resolve disputes is always better than vigilance. Everyone should want that. Sorry accelerationists.

I don’t know what systems will evolve. But if we don’t start investing in them now we are in serious trouble. I’ve been investing in solutions that are venture scale for sometime. Ifyou want to join me on this journey, DM me on Twitter or join as an LP.

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Homesteading Politics Preparedness

Day 782 and Vanity Fair

I am extremely proud of being a subject in Jame’s Pogue’s new Vanity Fair piece. It is about managed decline, the death of state capacity, and whispers of a post state world. I’d say it’s a bombshell except I think there are some very sober people discussing how life in a chaotic world filled with distrust might work out. Spoiler alert, not great.

“Preppers, techies, hippies, and yuppies are converging on the American West, the safest place to “exit” a society gone haywire.”

The Dissident Fringe

I worry that the next frontier in American cultural battles will be figuring out how to stay out of our versions of “the troubles.” And I don’t like the sound of that.

I think you may find yourself agreeing with me. I don’t want a culture war and I certainly don’t want it to turn into a hot war. Apparently that makes anyone who agrees with the above premise a dissident fringe. Didn’t realize it was controversial to enjoy civilization. But I am in fact comfortable saying I don’t want any kind of war.

But I’m not sure everyone feels that way. So in a show of our seriousness we’ve decamped to the imagined demilitarized zone of the Rockies. I don’t want any chaos but I am literally betting the house on us having a bumpy ride maintaining course in America as we deal with long delayed issues from infrastructure, education, logistics and supply chains to capital markets and trade. I intend to capitalize on this uncertainty. You can do so with me if you’d like as an LP in chaotic capital.

If you are curious about how it might play out, in this nearly 9,000 word opus, every angle of how to survive in the American West in the near future is captured in empathetic detail by Pogue. It’s almost like reading William Gibson in how it shows a present that feels a bit off. Cyberpunk right before the Jackpot, but make it from a gonzo Hunter S Thompson type. I appreciate it on purely aesthetic grounds. You should read it.

But practically how do we all muddle through a greyzone war that has no agreed upon values, including whether the enlightenment & liberalism are worthwhile?

As we fight it out as a nation, most of us are just going to continue living our lives as crashing stare capacity and war over institutional norms gets in the way of raising a family and doing business. And it’s this scenario—a muddling, unhappy, middle course—that most people in this sphere tend to predict is coming. It’s not fun but it’s not the end of the world.

It is my personal belief that we are struggling to find any alignment because regardless of your personal politics, religion, or even overriding philosophy, your actual physical body is just fucking done with this bullshit. I mean it literally. We feel it in our bodies.

Endocrine systems get fried. There’s too much cortisol, you’ve been running on adrenaline, eventually you tap out. Everyone feels nuts right now,” she said, “because what on earth are we supposed to do with the fact that we’ve had this incredible rate of change for so long.”

Julie Fredrickson – Vanity Fair March 2023

We think we’re keeping up with it, but our bodies are like, ‘Oh, actually no. We have no idea what’s going on.’”

It’s too much stress on the system and something is going to have to change.

If you read the piece you will see just how much trust is lost amongst all parties that make up the American experiment. The cherry on top is that our nation state distrusts our foes & but they also distrust us the citizens and their desire for more freedom. It’s a messy battle for meaning and power.

And as Americans we’ve had the exorbitant burden of the dollar being the global currency. What happens when we no longer trust any actors on the global stage? Distrust our fellow citizens, distrust our currencies, distrust our institutions, distrust our enemies? It sure gets hard to run an economy without trust.

We need to build new systems we can trust or our bodies and minds will give out. Simple as.

I don’t know what systems will evolve. But if we don’t start investing in them now we are in serious trouble. I’ve been investing in solutions that are venture scale for sometime. Ifyou want to join me on this journey, DM me on Twitter or join as an LP.

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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.

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Emotional Work

Day 718 and Change

As I supposed is natural towards the end of a calendar year, I am thinking of the ways this year has changed me. I will surely look back on 2022 and think that was a year where a lot happened.

I expect a lot to keep happening in the future. If anything 2022 will feel slow by comparison. You can already feel the present speeding up can’t you? That sense of anxiety you feel all around you is a collective state of future shock. Our endocrine system has been pumping cortisol on overdrive as we desperately try to sensemake the chaos. And it’s only getting worse.

Yes I’ll remember that this is the year I moved to Montana. I’ll remember it as the year I really began to formalize my investing. I’ll remember it as the year I laid the groundwork for huge personal life changes. I’ll remember it as the beginning of a new chapter.

But I’ve really got no idea how fast this thing is going to go. We’ve got a recession and geopolitical power struggles and commodities concerns and climate chaos and who knows what’s next. But I think if you are nimble and can adjust fast you might just surf this wave. I’d be prepared to wipe out. But I think it’s going to be a good ride.

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Medical Startups

Day 696 and Edge

I’m enjoying a migraine this weekend that was both strong and as of yet unbeaten. Perhaps I overdid things on Thanksgiving and Black Friday. But I’ve been stuck in bed in a dark room for the last 48 hours or so.

While this sounds a bit miserable, I can assure you it is also part of my edge. When my physical works shrinks my cognitive capacity unfurls. I very much liken it to the traditional super hero dilemma of being gifted with something that makes living a normal life a challenge.

I may be stuck inside struggling with light, noise and smell but I can still do most of my core deep work. I can’t take calls or go to meetings but I can be on my phone and my Kindle. I can intake information and I can synthesize that information when I’m in darkness.

And that is 90% of my job. Be informed and make the best decision you can. Those decisions are generally done when you are calm and fast. And I get the benefit of being in rest and digest as often as possible as it’s what keeps me alive.

I’ve got a generalized theory related to finding one’s edge. It’s pretty simple. If other people perceive it as a weakness but you understand how to wield it as a strength then your got an edge. People dismiss you sure. But being underestimated is one hell of a way to get on the better end of a trade.

And so while I’m here looking like I might not be worthy because of some set of heuristics that’s have typically worked well for you I’m actually the one that has a leg up on you. You would do well to think about all the ways in which you can leverage talent and insights that trade below their value. You can make a lot of money betting off of truly underestimated viewpoints.

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Emotional Work

Day 693 and Thanksgiving

I’ve got so much to be thankful for this year. And it’s the first time since the pandemic began that I’ve felt optimistic about where I’m going with my life. Even if I’m a bit of a doomer, I remain a believer in the human capacity to figure shit out. The road to tomorrow is long and bumpy so best plan ahead.

I’ve had a certain worldview for a while. That we may have some hard years ahead of us to earn back the heights of our boom. Nothing in life is free. And we dined out on energy and resources that had hard costs.

But I prepared for the possibility that life might be harder. I got us to our homestead in Montana this year. To think before this year we’d never owned a piece of property before. It just wasn’t a possibility for so long and then we bounded up on the flush years and found a way to realize some gains.

So I’m grateful that on this cycle of the churn I’ve played it well and fair and I’ve set my family up to work and thrive during hard times. We didn’t get over our skis but neither did we fail to prosper. And for that I am grateful. I am thankful to have been able to play to higher standards but also not gotten eaten by the bigger beasts of capitalism.

I suppose it’s also no accident that I’ve also felt I’ve been thriving in my personal life. I’m so thankful to have made progress on becoming more myself this year. It will probably in hindsight be a demarcation between some of the compromises I made in my youth and some of the boundaries that have led to maturity now.

The more I let go of old copping mechanisms and become more myself, the better I do at achieving my goals. And I hope I can remember this lesson every day. If I can do that I will always have something to be grateful for in my life. And on this turn of the wheels I am offered another chance to defy the odds.

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Startups

Day 688 and Hardcore

My generation of founders came of age during the peak of hustle porn. We were young and dumb, and even without the use of stimulants and nootropics like our Gen Z younger siblings, we got a lot done. Probably because we were well young and dumb. And it’s easier to do things with brute force when you don’t have better tools. Being hardcore made sense for some of us.

Alas if you burn the candle at both ends you may find yourself with an astonishing array of healthcare issues in your thirties. Which is astonishingly common in my cohort. I’m just one of the rare examples that is public about the dangers of overworking yourself. Hustle porn’s legacy is mixed. We lost founders to workaholism and occasionally much worse. A generation learned that mental and emotional health are just as important as physical health.

Hustle culture coincided with a lot amazing companies getting built but it’s not entirely clear to me if being hardcore is the only factor at play. Tempting as it may be to look for simple mono-causal relationships in life, the math of success is never that simple. Life isn’t an engineering problem. And even if life was an engineering problem, applying more force doesn’t solve all problems. It might even make a few worse.

I don’t want to knock hard work obviously. Im a firm believer that the basics never go out of style. Hard work is a given. Most of the greats are working hard because once you discover you have a natural talent then maturity generally encourages you to hone it.

Success is built from many fathers even if it’s mother is hard work. Proper resourcing, adequate incentives, teamwork and an effective hierarchy of respect within it are all factors. And let us not forget just plain old good luck matter just as much as being hardcore.

So tempting as it may be to give in to Twitter discourse narratives don’t get fooled into thinking someone that is successful has it all figured out. You don’t know what it took to get there and who brought it together. Don’t overweight success on its own. Nothing is ever that simple. Expect that the team you want to be a part of will demand that you demonstrate all of the above virtues and along with the necessities of hard work. But if it all comes together it is worth the sacrifice.

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Finance Startups

Day 687 and Winter

It’s cold out there. And I don’t just mean metaphorically. Winter came early and hard to Montana just as the Farmer’s Almanac predicted it would. Driving back in from town last night after grocery shopping it was -3 degrees on the car’s temperature gauge just after sunset at 6pm.

It’s cold out there in the capital markets too. The federal reserve is raising rates to tamp down on inflation and the cost of capital is hitting the technology industry. Frankly I think we’ve all been waiting for an excuse to cut the fat and now we’ve got it.

But it’s going to have consequences for startups. Founders who have never had to live with the harsh realities of a down market are in for a surprise. Those juicy valuations in the private markets don’t work so well when the public markets can find safer returns in a Treasury finally paying out on a t-bill.

Let me play with a tortured metaphor to help you understand the situation. You think you understand how cold winter will be until you realize you haven’t had to work through a chill for over a decade. Sure maybe in your closet you’ve got a nice coat but when was the last time you wore it? If it was for a ski retreat with one of your venture partners then this metaphor is absolutely about to do double duty.

Surviving a bitter cold isn’t just about having a bulky down coat. Think of that as your cash runway. Without adequately rated cold weather gear to keep you alive you may find yourself tapping out. But it’s not just about the coat.

Keeping warm and staying productive requires some technique. Do you understand how to layer correctly? Do you have hats, gloves and scarves? I bet you walk around with ankle socks and Allbirds. That’s not going to go well in a foot of snow. Do you know how to eat for the cold? How about hydration?

Your team will need more than runway. They are going to need motivation to work with less fuel. You have to show them that the climb up the snowy mountain is worth it.

A winter startup team will need the skills and flexibility to work around problems that can’t be solved with money. Shit can and will go wrong on a long cold climb out of an economic winter. Creativity and belief must overlap with intuition if you want to make it.

And it’s important to remember lot of your team won’t have those intuitions. We’ve all been living in Miami and suddenly it’s -3 in Montana. And guess who gets to teach them how to adapt? You. You need to teach your team gently and with empathy what it will take. And they will makeup mistakes. Have you ever watched someone try to lace up boots for the first time? You might need to help them cinch.

I promise it is worth it though. If you are climbing the right mountain, and prepare adequately for your journey, the rarified air of a successful startup is invigorating. And the view from the top isn’t bad. If you need some help thinking all this through as a founder drop me a line Julie (at) chaotic dot capital and I’m happy offer some Sherpa advice. I lived though 2001 and 2007 (I even got laid off during RIP Good Times) so you can rely on me for some elder millennial wisdom. Stay warm!