Categories
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.

Categories
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.

Categories
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.

Categories
Preparedness

Day 677 and Bad Moon Rising

I got woken up at around 430am this morning by my husband. Now he typically wakes up earlier than me but rarely does he rise before 5am. He got out of bed and I heard one of our doors opening. A few minutes later he was back in bed and I drifted back to sleep.

It turns out he was getting up to see if the lunar eclipse was visible. Much of Southwest Montana got blanketed in a significant snowstorm, so alas cloud cover prevented him from glimpsing the eclipse with the naked eye. The blood moon was hidden behind a white out.

The eclipse was soon forgotten in the excitement of the storm. The snow was so powder fine we immediately suited up to do the adult version of playing outside. We had our first opportunity to hook up the snow blower attachment to our tractor to plow out our very long drive away. I took dozens of videos and Alex absolutely wrecked me by blowing a bunch of snow at me. We captured the comedy on the security camera and it made for a good laugh.

But the day unraveled almost immediately. The blood moon began to feel a bit like a bad moon rising. News of crypto exchange FTX getting “acquired” by Binance after 48 hours of sniping between CZ and Sam Bankman Fried. It’s a complicated story but it basically amounts to a bank run. Crypto was having a JP Morgan moment that appeared to have been manifested as some kind of grudge match on Twitter. The financial markets largely seemed like they didn’t care.

But crypto isn’t even the big story of the day. It’s Election Day in America where the midterms have been hyped up into an existential crisis. Which seems like a stupid thing to do when you are bound to lose just based on past election history (the party is in power tends to lose the midterms) but whatever everything in American life is existential now.

I’ve been on a doomer beat for sometime. Not that I think everything is necessarily getting worse but rather a series of macro level trends are headed in the wrong direction. I’d like to continue to live a nice life. I see the bad moon rising. And I made a set of life choices to get my family to Montana. I’ve got a serious of predictions about what it might take to thrive in harder times. And I’d be lying if I said I didn’t feel a little bit smug about having beat the rush. So stay strapped out there my friends.

Categories
Internet Culture

Day 671 and Greatest Show on Earth

I cannot tell if I’m absolutely utterly sick of watching Elon Musk take over Twitter or if I’m having fun watching it all.

Like Musk I am a Twitter addict. I’ve been a power user for the last several years as it was the hottest ticket in town as the media circus around America’s partisan emotional meltdown fomented in the wake of Trump’s presidency. If you were interested in news then Twitter was the place to be from about 2016 onwards.

The funny it is that I’ve had access to Twitter since basically day one but was never a consistent user. A friend was an early employee (so early he went to work for the podcast company) while I got to watch it all play out from the start it didn’t really capture my personal usage for sometime.

I absolutely wasn’t a power user in the early years. I was much more interested in blogging at the time. I ran an advertising network for bloggers and was absolutely obsessed with media. Media was much more interested in WordPress and subsequently Tumblr than it was in Twitter. And I wanted to be where media spent it’s time. Media took a while to really cotton into Twitter.

I was so disinterested in Twitter I didn’t even keep my original handle. I went for years without really being an active participant on the platform as a user. Which was ironic as I did quite a bit of advertising on Twitter.

When I sold my advertising network Coutorture, I decided I needed a corporate job to level up my skills. I ended doing advertising buys and heavy integrations with Twitter as I first went to an agency and then eventually brand side as an advertiser. I was no joke the first brand to live tweet the Super Bowl.

I was a director at an agency that ran digital for Pepsi and I ended up as the voice of Sobe. I was embarrassingly Lee the Lizard during the Super Bowl. At the same time I was also running a second Twitter account for Pepsi based on an SNL skit called PepSuber. We thought it needed to be live tweeted for maximum effect. No joke I was on a conference call with Lorne Michaels at 2am the night before the Super Bowl. The absolute coolest thing I did on Twitter though was probably the first Twitter aggregator. Through my friend I got access to the Twitter API and built a dashboard called Tweefreshing for Pepsi. It was Pepsi integrating all the best tweets of the day for you. It lasted like a day before it got abused. I know simpler times right?

Twitter has gone through a lot of ups and downs as an advertising destination and as a nexus for power and users. It’s always been a circus. It’s never really managed to grow up as a destination for advertisers. I don’t know where it’s going and this is clearly a nostalgia post for me. But over time it won me over. I went from a bystander to an advertiser to a power user. And I remain hopeful it will find a way to remain the greatest show on earth.

Categories
Politics

Day 664 and Political Disabilty

I did not watch the Pennsylvania senatorial candidate debate between Democratic Lt. Governor John Fetterman and Republican tv personality Dr. Mehmet Oz because I live in Montana. Why the fuck would I do that? But I have caught the discourse surrounding it and I do not like it.

If you are not following this saga, Fetterman had a stroke a few days before the primary in May. He is recovering but but is still having trouble with speech. People who are not familiar with neurological recovery processes (otherwise known as 99% of normal humans including me) are freaking the fuck out about what it means that his speech is impaired. It looks particularly egregious when compared to Dr Oz who is professionally competent at communicating clearly on television because that is his job.

Naturally we are seeing the absolute worst possible response to Fetterman’s current disability from just about everyone. Supporters of Fetterman are insisting that there is no evidence of mental degeneration or acuity issues. Which might be true but I don’t know. But the general sense I get from supporters is one cannot even suggest that there might be processing issues because doing so would you an awful ableist human being. Neat!

On the flip side, Republicans and other opponents are insisting Fetterman isn’t fit to hold office as he is not capable of speaking clearly. The Republican position seems to be that a speech impediment is a clear sign of mental decay and electing him is maybe a diverity and inclusion policy so wrong it should insult us all. Also extremely neat!

I’d say naturally both positions are ridiculous but I’m not sure this is natural to anyone. Ableism, or discrimination against the disabled, is an exciting new front in the culture wars. Being being disabled is a hot new identity marker despite the fact that a quarter of Americans have some form of disability. It’s not that unique or cool to be disabled. But modern medicine is a miracle so we can’t rely on Darwin anymore to keep us damned cripples out of sight anymore making light eugenics kind of a popular position. I don’t love it.

I am someone with a modest disability. I have a spinal condition called ankylosing spondylitis which is basically arthritis in my spine. So I don’t find any of the commentary surrounding Fetterman’s disability status encouraging. I don’t love that the basic assumption is being less than abled bodied is disqualifying for work. It depends! This shouldn’t be a whole fucking thing.

A disability doesn’t mean you can’t work like a “normal” person but it does mean you have some limitations to work around. This doesn’t make you better or worse as a person. Being disabled has no moral valence. Alas we tend to valorize suffering and demonize perceived weakness. Neat!

My position is most disabilities are sort of a modest inconvenience that on balance forces you to hone other abilities to be competitive. This is my super hero theory of disability and might be a contributing factor to the side that valorizes disability. How cool is it to be an X-Men? Extremely! But I don’t overweight this position as I largely think a market economy fixes by forcing us to all to compete and find our niche.

If this is scandalous to you, I’d say everyone has something that is a struggle to overcome even if most people’s thing is just being kind of an idiot. Half of us are by definition below average. But imagine if I thought you being stupider than me was disqualifying for holding political office.

My whole point in this long ramble is that the Democrats are being ridiculous in insisting we cannot look at the strengths and weaknesses that come with bodies being sick. We are on year three of the pandemic so that ship has sailed. The Republicans are being ridiculous insisting that speech impediments are disqualifying. Tump didn’t even have the benefit of a stroke to blame for his speech patterns.

It isn’t ridiculous to ask someone to be transparent about recovery and abilities. I’ve got no idea if Fetterman has slower thinking after the strike or if it’s just slower speaking. I don’t really care to be honest. Not my senator.

But if we all keep insisting on physical and mental perfection from our elected officials we might not have any politicians left. Which actually on second thought might be ok.

Categories
Culture Politics

Day 662 and Immobility & Gender

Americans are incapable of getting things done. Such is the popular sentiment of the moment. We are immobilized in some form of national endocrine collapse brought about by too many years of chaos and accelerating change. Our problems aren’t getting fixed and we are all too demoralized to do anything seems to be a popular consensus.

Some folks blame democracy. Some blame the degradation of the balance of power as our executive branch overtakes the legislative. Much ink and chatter is being dedicated to the upwelling of populism and it’s charismatic authoritarians as the solution to our stagnation and immobility globally. Or maybe it’s because we cannot imagine a better future.

I’m chewing on a new theory. What if it’s got nothing to do with democracy or a return to monarchy, or even lie inability to cope with chaos at all? What if history isn’t repeating but rather history has come to a crossroads and women are smack in the middle.

What if we can’t get anything done, because we’ve not come to terms with what power and authority women wield? What if this is mostly a reactionary period about what to do with women? What if the crisis of men is actually a crisis about women? What if all of the insecurities about modernity boil down to we changed gender dynamics quite a bit in the last century?

Populists and neo-monarchists are fucking themselves because they aren’t quite sure how to deal with the middle ground in which they find women. Women are neither fully in charge of the home, hearth and children (single earner households having become unaffordable) nor are they treated as equal actors in the public stage. The answer the throwbacks give is we should return to traditional gender roles. Except that’s not actually an option even if it would help.

Powerful women are at best mediocre ciphers (Liz Truss comes to mind) or one in a million talents (Indra Noyi for instance) such that gender is far beside the point. The middle ground of most American women is a mess of confusion about demographic collapse, loneliness, and the good life.

The Dominionists, Christian Nationalists and various flavors of neo-patriarchal traditionalists believe the solution is simple. Bring women back into the home and to the elbow of their menfolk. Men are obligated to the public sphere unlike their women for whom it shouldn’t be a concern at all. Which seems like a strange approach to problem solving. Return to only half the planet having authority.

This is a bit like putting the genie back in the bottle as we’ve got a full century of women’s suffrage under our belt and two generations of women working outside the home. Capitalism in particular loves women workers.

Combine that with the degradation of men in modernity and you start to see some of the challenges. All of our status markers suggest it is better to be unmarried as a woman than married to a loser. That didn’t used to be true but birth control and third wave feminism probably made it so. And in late stage capitalism most men are being framed as losers, lacking the soft skills to navigate corporate politics and higher education.

I frankly haven’t the slightest idea what anyone is supposed to do about this. Accordingly to the viral Female Delusion Calculator (funny how there isn’t a reverse option) my husband doesn’t exist at all demographically. But then neither do I.

So one can’t really be looking to some globalist asshole white Americans to solve this problem. We are the problem according to a large swathe of people. Unless we are the ones capable of overcoming immobility as we’ve got the spare capacity. But I think rich folks running the show been the default state for most of history so fuck if I know. But I do think I’m onto something with gender being at the center of a lot of our issues.

Categories
Aesthetics Startups

Day 659 and E-commerce Returns

It’s been a minute since I posted about the mild annoyances of shopping to outfit a new house. Because we have upgraded the amount of space we live in by two or three times and we are hoping to use some of the space for hospitality we’ve bought a lot of shit recently.

I have shopped a large assortment of direct to consumer retail brands. Included in the list is Brooklinen, Havenly, Italic and Merit in the last month or so. And the varied state of quality and service in the venture funded retail space is such a mixed bag. The most pleasant experiences have been from older brands and retailers like Carharrt, Ariat and Sephora.

I would entirely recommend Havenly as an intermediary service for both design and furniture shopping as the returns are relatively simple and they consolidate a ton of retailers into the interface. But they are so good at their jobs you mostly don’t need to return stuff. We bought a cheap fake antler chandelier to see if it could be pulled off (against the advice of the designer) and were promptly told by everyone to return it. Which lets be honest was good advice all around. We did have to dismantle it which I’m told was quite the IKEA style effort.

A fake antler chandelier acquired from Wayfare. It was still $500 so we returned it.

I cannot say I have the same praise for direct to consumer brands that are still attempting to make margins happen in the middle market. I’ve had some amusing fails on that front and it again reminds me of the danger consumers are beginning to feel when they shop brands with less social awareness. This is a real issue for direct to consumer brands as they fight it out with less venture dollars compared to the past. It’s going to hurt their lifetime customer values.

Merit is a much covered cosmetics brand which has some star products I liked (their foundation is terrific) but some really low rent packaging. So I wanted to return a couple items. Merit made returns so challenging I might just eat the cost of half the products that I don’t want to use. Merit’s customer care team literally wanted me to write reviews of each product I wanted to return to begin the process. Damn girl but ain’t nobody has time for that.

An assortment of Merit Cosmetics including foundation, blush, mascara and a brush. I wanted to return about half of them for being a poor value.

Ironically I had already done that on their Yotpo product review prompts a week earlier but didn’t save them (why would I) so when it came time for returns I just said fuck it as I didn’t want to retype my 500 word a piece reviews again just to return the items. It’s been sitting in my inbox for so long I’m afraid they won’t accept it. A huge and amusing fail to integrate basic customer retention tactics and your order options. I expect it will hit their lifetime customer value and require a fix soon. I literally haven’t overcome the inertia just to get my $70 back and perhaps they know that. Which is a dick move.

By far the most clever return mechanic I’ve seen is from Italic. I’ve loved their cashmere and their sheets but some of their other odds and ends were just bad fits. And it turns out they know it. They offered a 50% store credit on an item if I just gave it to a friend. Alas it is a dress that doesn’t work if you have breasts. Which is clearly a challenge to hand off to anyone.

Text messages between Alex and I about returning a dress from Italic that does not fit my upper body

The other irritant that Italic had though is that it shipped in four separate orders and insisted that we ship it back in four separate orders which is wildly wasteful even by e-commerce standards. And it has the unexpected effect of me accidentally returning a pair of cashmere pants I didn’t even try on as I forgot I bought two different cuts and ended up returning both as they came in separate orders over the space of a week. Oops! That’s $150 they won’t get from me. I frantically texted my Alex asking if he had them still but nope I might try to rebuy them but now I don’t trust I’ll be able to even figure it out.

Shopping is going to get extremely weird over this holiday season as brands have significant depths to overcome come past supply chain issues. But as the economy struggles with inflation I’d expect to see more tricks like Merit on the negative end and clever loyalty gambits like Italic on the positive. So keep that in mind as Black Friday approaches.

Categories
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.

Categories
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.