Category: Finance

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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!

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Finance

Day 684 and Newcomb’s Paradox

I like mathematics. I’ve got very little talent for arithmetic but formal proofs were something I could feel my way through. I only learned this by failing regular calculus so badly and getting rescued by my roommate who is the scion of a very important family in algebraic topology. Bet you didn’t know that was a thing did you? He showed me that mathematics isn’t about numbers at all but about the logic of the universe. Also he kept me from flunking out. Thanks Tom!

I know the above sounds silly, but in academic circles math is one of those “purest” of institutions where cognitive processing power matters a lot and absolutely nothing else. They are some of the most deeply impractical and removed from reality types of humans you will ever meet.

I’m autistic enough that I found the company of this type of human deeply comforting as they comforted me though my shame based need desire to be normal. Literally no one will make you feel more normal than someone that works in formal logic and it’s adjacent philosophy of decision theory. I bet a lot lot of pretty girls with daddy issues have found this to be true if the LessWrong community is to be believed.

Because of how close I was to my roommate (and still an even though we don’t see each other enough) I got to spend time with a lot of utterly bizarre math people. And it really runs the gamut from those who are functionally pirates who can barely feed themselves to the founders of Renaissance Capital. They are a good time generally speaking. Extremely chaotic people who drink thousand dollar bottles of champagne from solo cups while discussing science fiction are my definition of a good hang.

But they are not what you’d call standard issue humans. If you’d like to know exactly how, ask them to explain how being three standard deviations from the mean has affected them and don’t interrupt them for thirty minutes. I am an outlier in many ways. But I don’t hold a candle to some of the folks I got to meet.

The reason I titled this post Newcomb’s Paradox is because it is thanks to early exposure to mathematics that I got to explore the complete irrationality of rationalism. Newcomb’s Paradox in its simplest format tells us that in an irrational system it is not rational to behave rationally. It is a paradox because this is both true and not true.

If you have some common sense you are not immediately knocked on your ass by this revelation but it turns out to be so unnerving. Unfortunately for some folks at the edge, which is most folks who are mathematicians, it might also break their brain. Effective altruism is now being blamed for its adjacency to the entire Sam Bankman Fried committed fraud at FTX scandal because they took the paradox entirely too literally and not at all seriously.

And given the dangers that can come from extremes perhaps more of us should be spending time with mathematicians. Math pirates when combined with high finance and potent philosophies might need tempering by those of us only two standard deviations out.

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Emotional Work Finance

Day 683 and Goverance

I’m not a big fan of early stage venture investors meddling too much in the day to day of their portfolio companies. Asking for too much reporting and too frequent board meetings can be a huge source of momentum friction.

But I am a big fan of corporate governance. Even right from the very start. You should have agreed upon avenues for settling issues and disputes from the moment you have assets bigger than an Ikea couch let alone a 32 billion dollar valuation company. A lack of governance structures can lead to deeply destructive behavior even if you aren’t a sociopathic rich kid bent on committing fraud.

As much as it may seem irritating to set up formalities like a full board and agreed upon voting rights structures, you will regret not having it if something goes wrong. And something will go wrong. I’d go so far as to say Murphy’s law is an immutable law of the universe. What can go wrong will go wrong.

The intense pressure of a startup is what turns the lump of coal that is your vision into the diamond that will be worth something in the open market. And pressure is often destructive. People who otherwise respect and trust each other can slowly find themselves deeply at odds.

Just think of your worst breakup and imagine that intensity playing out in ways that impact everything you’ve worked to build. If you’ve ever gone through a divorce I’m sure you understand. Let me tell you a little story about one of my breakups to illustrate why you should set up governance right form the start.

My easiest personal breakup was also one of my worst. We’d moved in together and devised an elaborate set of budgets and savings protocols. We’d combined belongings. We even set up a shared bank account. He was a corporate governance lawyer at a very aggressive firm. I was working a lucrative corporate job but preparing to go back to startups.

While he wasn’t a contract lawyer, he did have enough common sense to suggest we write up a relationship contract complete with dissolution protocols. I thought this was absolutely brilliant which I’m sure tells you a lot about how I operate. Absolutely all of our friends thought we were nuts. Including a colleague and friend who would go on to be one of my board members down the road.

I was in Colorado for my mother’s wedding. I’d expected my boyfriend to join me. But we’d been discovering that all our good faith attempts to arrange the perfect relationship structure was nothing in the face of widely disparate personalities and risk tolerance. No amount of mitigating structure could overcome those differences.

When I came home he’d triggered our breakup clauses and moved out. Everything was done by the governance protocols we’d set out. If I’m absolutely honest I was relieved. My biggest annoyance was losing the Vitamix blender that was his property. As furious and heartbroken as I was at the time, I didn’t have any avenue to engage in my worst most defensive reactionary emotions. Neither did he. Which was extremely valuable as I hadn’t at age 26 gone through the therapy that helps me productively channel negative emotions now.

My ex-boyfriend and I are still friends to this day. Sure it took a few years for us to come around but we’d avoided a scorched earth situation despite the significant risks we’d engaged in by moving in and combining our lives and fortunes after a relatively a brief period. The damage was mitigated by a shared understanding of how we’d manage downside protection and whose rules we’d consider binding.

While I’m sure this sounds a bit weird, I do think it’s a helpful illustration of why even the most optimistic scenarios benefit from guardrails and mutually agreed upon avenues for pursuing a dissolution or change in status.

No matter how calm and rational you think you are, there will be scenarios that trigger deep emotional patterns. If you vomit up those childhood coping mechanism emotions, you need to clean it up even if it feels shameful and embarrassing.

I’d also say it probably tells you a lot that I’m telling you a deeply personal story about a breakup in a personal relationship and not my actual board experiences. There are some secrets you take to the grave and how you failed your business partners tends to be one of them. How they failed you is another. I’ve had reason to be grateful for corporate governance guardrails at all of my companies. Because that is human nature.

So no matter how early it is in your startup journey you should be considering how you’d handle tough times. Set up a board to help you work through and arbitrate disputes. I know you cannot imagine it now but you won’t regret it.

No one is ever fully immune from disagreement (or even disaster) and you owe it to yourself and your partners to set up fair resolution issues from the start. Plus if you happen to have partnered with a sociopath you will appreciate the modicum of protection offered by binding contract law or consensus mechanism contract execution. And if you really want a Vitamix make sure you put that in the contract.

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Emotional Work Finance

Day 680 and History Repeating

I found myself crying my eyes out to my therapist this morning. Just full on sobbing. Nothing bad actually even happened to me during this week’s chaos. In fact, I’ve spent the last year or so preparing Alex and I for a downturn. I wouldn’t be much of a doomer if I didn’t swing into this downturn prepared.

It just all felt too familiar. It felt like the worst days of fear and insecurities from my childhood playing out all over again. My family went bankrupt during the great Web 1 unraveling. And I’ve never forgotten it’s lessons.

I remember feeling like I was in a secure situation and then learning in dramatic fashion that it was all gone. That all the hopes, dreams and aspirations that my father had done so much to prepare me to reach for (including a lot of very expensive colleges) would likely be out of reach. We’d be starting from scratch again. I hadn’t really had a lot of time to enjoy being a poor little rich girl. It was over too fast.

My father is a truly entrepreneurial man. When I was born the family lore is that he was pitching a edtech company. We were a startup family. We lived in Fremont which is (was) the shitty poor town. I suspect it was a lot harder than I even remember.

But dad found a way to realize his Silicon Valley dreams. He brought software to millions of people. He really did do the thing. And for a few years during the boom times it felt like we might be wealthy forever.

But finance is tricky. Lock ups can fuck you up. So can leverage. We had both. And then of course regular old fraud happens too. Yay.

But it wasn’t in vain. I learned those lessons well. I swing big and I bet on the future like my dad. I believe in people and in genius. But I also keep a balanced portfolio and back up plans.

I believe in exponential growth. But I also believe in the cost of capital. Sometimes money is cheap. Too cheap. And you need to prepare for when capital is expensive again. Because the laws of physics tell us that energy cannot be created or destroyed. And until someone smarter than me proves the laws of thermodynamics wrong, I will operate based on them.

And I am ready for the dark days. Both because it is literally November but also because I believe we’ve got chaos ahead. And if I’ve learned one thing from my childhood it is that you can survive it. It just takes a little bit of preparation. Which I’ve done. Everything else is just a case of history repeating.

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Finance Internet Culture

Day 678 and Winging It

I went for a haircut today. I’d been riding a haircut since May so it was a little embarrassing. I’d let it go from princess to dirty hippie.

Joking with the hairstylist a bit about being a bit weird we ended up commiserating over how much we enjoyed Twitter. She agreed that Twitter always felt like it was more real. Like people let it all hang out. And recently we all collectively realized that everyone is just winging it.

Nevertheless it can still be kind of a shock when it goes from “oh anyone can become one someone with hard work” to “oh fuck everyone is a fraud.”

I am I’ll admit a little shook about Sam Bankman Fried. I’ve got minimal exposure but I have interests that have been funded by funds that do. And that is really distressing to me. It always feels like at the center of the bullshit in this industry lurks some traditional finance fuckers not doing their math. And I do admit that chaps my ass. Sets us all back.

I do think plenty of the world is just winging it with a good faith and open heart. But for the sliver of sociopaths who know enough about governance and fiduciary duty and still decides that nah I’ll mix up some assets and ownership. Fuck you that’s regular old fraud and it sucks.

And what’s worse is you bring this on to our house. The people who do want to build a Plan B and who sincerely believe that a fairer more open accessible financial system is a global good. The people with shitty passports and communist governments actually need access but go ahead and you do some light self dealing. This isn’t important enough to you. Cool. Whatever. Nothing was riding on this.

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Finance Internet Culture

Day 654 and Inappropriate Language

As much as I love to joke about getting cancelled on Twitter, I’ve never actually worried about getting dinged. I resisted getting a Blue Check and otherwise pursuing the trappings of being a power user as I was confident that my real world connections would overcome any algorithmic nonsense.

Digital power still resides on a firmament of real world power. I figured I know the right people in real life at Twitter, so short of me encouraging a coup while also being the President of the United States of America, I was pretty safe in maintaining control of my account. This was perhaps a bit naive and I knew it.

The algorithms do in fact come for us all. I got an unprompted warning today that a user on my account (I’m the only user but whatever) had been deemed to be using inappropriate language.

A Twitter warning saying my account AlmostMedia has inappropriate language so is ineligible to run advertisements

At some point I had the power to run promoted posts, otherwise known as advertisements, but because I have angered the language police at Twitter I am now no longer allowed to pay to promote my own speech. I guess I overrode the “are you sure you want to tweet this most users don’t use this speech” warning one too many times.

I swear more than average for a woman but probably a lot less than average for someone in finance. My account is notably a shitposter account. I remain fascinated by social status and access of all kinds, and shitposting remains of the higher status activities in social media culture as it demonstrates you need not be censored by social mores or common decency. Except apparently I can be.

You can get worked up about whether this infringes on my speech as I can say anything I like but now I’m no longer able to pursue any paid reach. This is the popular theory that everyone is entitled to free speech but not free reach. Or I guess in my case paid reach.

To be honest I had no intention of buying any paid reach advertising on Twitter. The folks I care about generally seem to get my Tweets and I’ve got no sense I’ve been shadow banned. Well, ok now I am worried but I wasn’t before this goofy warning.

To me this feels like a reminder that Twitter just doesn’t give a fuck about its power users. I am a well networked and well liked (or well hated) account with powerful followers in the core demographics that matter on Twitter.

I sit inside a nexus of media, finance and Silicon Valley personalities that care a lot about the platform even as the platform mostly doesn’t give a shit about us. Which is arguably why we’ve all spent six months giving a shit about Elon Musk buying Twitter. When a power user gets banned from advertising producers it’s not really a problem for the user, it’s a problem for the ad products team who is fucking up making money. You know, their job.

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Finance Internet Culture

Day 651 and Best Guess

I’ve loved the discourse of indignation that has surrounded rich men doing deals via text messages. There was lot of hand waving about the death of genius and the meaning of it all. Isn’t it such a scandal our best and brightest are just saying shit on Twitter DM?

I suppose if you never worked in startups or finance it might come as a genuine shock that rich techie people are no better or smarter than anyone else. Why the fuck do these dorks control all the money and resources then? I’d say it is because they are willing to make their best guesses.

One of my favorite scenes in Star Trek is Spock struggling through a series of calculations and informing Captain Kirk that he may need to make a guess. Kirk’s response? That’s extraordinary! Spock is naturally confused. Dr McCoy or Bones has to do some translating.


Bones: He means that he feels safer about your guesses than most other people’s facts.
Spock: Then you’re saying… it is a compliment?
Bones: It is.
Spock: Ah. Then I will try to make the best guess I can.

Star Trek IV The Voyage Home (The Whale Movie)

Everyone is just muddling through and making their best guesses. Even the best and brightest among us are struggling to make it all work. I’m not suggesting the folks making the Twitter deal are as good as Spock but they are just making their best guesses too.

And for whatever reason they are willing to put a lot of money, time and reputation on the line to see where their best guess might go. That’s pretty courageous in its own right.

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Finance Startups

Day 649 and Build in Public

People love building in public. The universe loves a specific ask. Today for my 39th birthday, I am doing both.

I would like to raise $5m for chaotic.capital’s rolling fund before I turn 40 next year. #5Before40 has a nice ring as a hashtag right?

Chaotic is the first check into founders and companies that adapt humanity to complexity. Personal flexibility, organizational agility, and societal sustainability.

Our founders capitalize on chaos.

You may have noticed I’m a bit of a doomer. I keep close tabs on the opportunities presented by an increasingly unstable world.

Climate change, distrust of institutions, geopolitical unrest, resource scarcity, rising tides of populism. There are founders who can help us address and survive these pressing issues.

My goal is to raise $500K per quarter via a rolling fund. There is 155K per quarter committed from folk like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company.

With a base like that, I want to do the rest in public here on the blog and Twitter. You can read the fund overview here. Building in public has generally been my preference and it has felt weird doing any of this fund work quietly behind the scenes.

You can 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.

I’ve got big ambitions for accelerating into maturity as I have no intention of letting entropy win.

Humanity deserves progress, and I demand growth for myself. I’d like to make us both money with that. 

______________________

FAQ TIMES

Haven’t you been investing through chaotic before? 

Yes but just with personal capital and an SPV. I want to scale it up as we believe our performance warrants it.

Go check out some of our best investments here. https://chaotic.capital/fund-overview

______________________

Why didn’t you raise more during good times? Why the fuck are you raising a rolling fund at the end of the world?

Did you miss the part where I am a Doomer? We are a bad times fund. This moment is where our thesis matters.

Good times return and you’ll appreciate having written a hedge check or two into weird companies that are designed for the power laws of institutional chaos.

Or if the fear of the moment feels overwhelming you can sit back and die the slow death of uncertainty. Trust me I’ve considered it as well.

But personally, I’d write me $10,000 check and come along for the climb back. Entropy only wins if we don’t fight back.

Categories
Finance Preparedness

Day 608 and What Timeline

I’ve been obsessed with a movie called Margin Call this summer. If you haven’t seen it, well it’s on Netflix, and it’s an exceptional piece of cinema with a top notch cast reflecting on why finance is so prone to boom and busts. It’s a great office drama even if you have no interest in banking. And it’s only an hour and forty odd minutes w two key Pete Davidson SNL skit criteria. It is both Tucci Gang and a Short Ass Movie.

One of the clincher scenes is Jeremy Irons explaining his job as the bank’s CEO to Zachary Quinto the young rocket scientist turned risk analyst.

I’m here for one reason and one reason alone. I’m here to guess what the music might do a week, a month, a year from now. That’s it. Nothing more. And standing here tonight, I’m afraid that I don’t hear; a; thing. Just — silence

Margin Call

I found this particular scene rather riveting as it reflects both the seeming ease and intense dangers of being in charge. Your entire job boils down to making a few big calls exactly right over a time horizon your average working stiff doesn’t even have the luxury to consider.

I’ve been considering my own preferred time frame on which to make decisions. I’m no Jeremy Irons. I don’t make exceptional calls on what will happen in a few months. I do however have quite a nose for what will unfold over much longer time horizons. I’d trust myself to make the right call over a decade. I scan the horizons.

Which if you are following along with some of my life choices should be modestly unsettling. I moved to Montana to a rural homestead. I invest in early stage startups that fit my chaotic thesis. I am comfortable being labeled a doomer and a prepper because catastrophic emergencies are in inevitability in complex systems.

And it’s hard to imagine a time when complex systems like climate change, geopolitics and macroeconomic trading pressure held more sway than now. Like Jeremy Iron’s character I am listening for the music. And my ear is trained on the silence coming down the pike.

Categories
Finance

Day 590 and Demography

User acquisition is my little niche in the startup world. While all founders are generalists my super power has always been getting the attention of customers. So I often enjoy little illustrative moments where basic principles of finding and speaking to your audience go awry.

I have tweeted extensively about my concern in the rising cost of core agriculture commodities in the face of shitstorm in the fertilizer markets. This isn’t that novel if you work in finance but it’s probably not a large group of people that are actively discussing fertilizer costs. I do not however buy fertilizer personally. I don’t finance it.

In the face of rising interest rates, partnering with Nutrien Financial™ can help you prepare for the future with confidence. Our latest blog post explores why financing your input purchases may be beneficial to your operation:🔗 nutrienagsolutions.com/blog/5-Reasons… #AgFinancing

I was served a tweet for Nutrien Financial. They would like me to consider financing my crop inputs. In fairness to this promoted tweet the final demographic detail Twitter may know about me is that I live on rural land with agricultural use zoning. I see how I got targeted. And I am delighted to be served this piece of thought leadership from them. But I’m not in anyway their customers base even though I mimic a lot that matches them.

Let’s compare this to another group of advertisements that targeted me this week. I got several pieces of direct mail in my physical USPS post. These folks knew that I had recently purchased a forwarding service from the USPS to make sure old post from my former Colorado address would reach my new one in Montana. Let’s take a look at what they advertised to me based on that piece of information.

A spread of several catalogs and promotional mailers for home furniture, blinds and window treatments and rural road paving services.

It looks likes advertisers who want to reach married couples that have recently forwarded their mail to a new address might be in the market for furniture, window treatments and also I guess rural road paving services. That one might be a rural Montana thing so slightly more niche.

Advertisers argue a lot about high intent audiences. That basically means someone who is likely to buy your product or service. Lots of people can fall into the typical demographic of what you sell but judging if if they are likely to be persuaded to make a purchase can save you a lot of money. Don’t sell to someone who isn’t buying.

Sure you can convince someone they want something with aspirations and glamour but you have to be able to be convinced. It’s a lot easier to do that for a lipstick than a couch. Significantly harder to do for rural road paving I imagine (though I’ve never done it so I can’t be sure). The hardest has got to be financial products for large scale industrial agriculture purchases. Finding people with high intent to buy fertilizer seems pretty specific.

Marketers can and do try to gussy up these facts with fancy languages but getting attention and selling to people that want to pay attention are basic. I’m not the tactics aren’t complex and the work can’t get extremely technical but at least we know we are working with human desires. And I think it’s important to think through that when planning a campaign. Don’t want to overspend on convincing someone who isn’t even in the market to be convinced.