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.
I used to be the CEO of a cosmetics company called Stowaway. We were a direct to consumer brand that manufactured and retailed our own line of travel sized makeup. Alas I got too sick to work and we sold the company to a private equity holding firm who shuttered it during the pandemic. I’m “shocked” that travel sized red lipstick wasn’t popular during two years of masking and lockdown.
I don’t particularly want to work in cosmetics again, even though I have arguably priceless experience that could be put to good use helping other brands. Startups are are traumatic and it’s not unusual for founders to find it challenging to work in spaces they know well. You don’t want to undermine the enthusiasm of founders. Also you’ve probably taken enough risks for a lifetime in a given space to never want to touch it again even if you made money.
But I do still enjoy being a consumer of cosmetics. I’ve got what might be the most comprehensive library of travel sized makeup in existence. I moved all of it up to Montana this year where it lives in a modestly organized vanity. For some reason I decided do a little reorganization of it today.
A very messy cosmetics vanity littered with makeup bags, travel sized packaging and a Sephora advent calendar.
Instead of finding a new schema for where I plan to keep all my products, I made it much worse. I let myself get a little bit of tunnel vision and instead of playing around for half an hour I spent an ungodly amount of time making it much worse. I’ve got drawers that are bursting with tiny mascaras, tiny lipsticks, tiny eye shadow palettes and thousands of other items.
I was surprised to find myself enjoying it. I did some comparisons of packaging and formulations and found that I was still quite pleased with what we had built. Many new brands have emerged since then but the promise of a minimalist purse friendly brand remains elusive. I see all the ways I failed but I also saw all the ways in which our team succeeded. And it was nice to feel like perhaps I’d learned something. But now I’ve got to clean it all up before my husband steps on an eyeliner.
So Elon, this isn’t likely to actually make it to you, but this is my blog, I write every day for myself, so why not, I can give it a try and pretend. If it turns out this is any good I’ll ask a mutual friend to send it to you.
tldr: I feel a (parasocial) connection with you & I want more from you (and maybe also for you). I know it feels cool and edgy to wink at taboos but you’re getting rekt by fuck bois, sycophants and opportunists.
I know we are all Galileo in our own mind shouting “and yet it moves” to narrow minded Papists but you realize being a martyr requires your death right? I don’t want you to die.
You certainly don’t remember this, but we met a number of times in the mid-teens. Times like when a friend of mine hosted a blow out birthday party in New York. We sat next to each other in some awful club and discussed chess with a small group. The same friend had a big wedding. I remember goofy dancing. Your sons made snow angels in the confetti. It was nice.
You seemed as uncomfortable as the rest of us nerds. Your autism didn’t seem any worse than mine though. I remember finding that comforting at the time. It has curdled into alienation over time as your fame far outstripped your origins. And I’m sad to have lost the feeling of love I had for you.
Before we “met” I had slight case of hero worship. I remember thinking here is someone just like me. He likes the same science fiction. He dreams about the singularity. He’s neurodivergent. And he wants to get us off this damn rock. And he’s got more money and power than I do so maybe he is worth admiring. I was young and stupid and hadn’t yet gone to real therapy.
I would tell my friends I wanted to die outside the earth’s gravity well. I thought perhaps you might be the man that got us there. Had I not had a chance to see how much you were just like me, perhaps I’d still be a stan.
What I see now from you isn’t power and happiness, it’s isolation and sadness. But I want you to know it doesn’t have to be this way. You don’t have to listen to the flattering dick riders. They want shit from you. They want their agendas and they see your money and power as a way to achieve it. I know you know this.
It makes me angry to see you coddle the parasites. I’m shocked your mother hasn’t told you to knock it off. She seems like a cold bitch who gets shit done. I’m sure she’s told you that you are better than them. The nerds and autists did not inherit this Earth just to squander it for the roar of the crowd. If it is all bread and circus, remember you are a king and not a clown.
Maybe you think their slavish slobbering attention is a fair trade for some of your magic, I used to be emotionally slutty like that too.
Being an attention whore isn’t unusual for someone with distant parents. Shitposters gotta post right? Once again, I feel a kinship to you on the compulsion to post and roast. I’m addicted to Twitter too. We are all filling up the holes leftover from our childhood. I’ve got daddy issues so I’m sure you get it.
And yes, I am projecting my own insecurities. But maybe I can tell you a story that will comfort you in the big wide universe. Maybe it will comfort someone else. Maybe it’s just to comfort myself.
I read you named your family office Excession. I’m also a fan of Ian M. Banks. Since 2008 or so, I carry around a paperback of Excession with me whenever I vacation. Which isn’t a lot. I normally use a Kindle to read but this paperback has become a kind of totem. It signals to my hindbrain that I am in a sympathetic state of rest and digest. I reread it over and over in 20-30 page chunks. It bounces me out of fight or flight now after much repetition, it’s my comfort book.
A picture from September 2014 in Miami. We seem to have come full circle on UkraineHere is a picture of you with the same copy in 2015 while in Sun Valley.
Your love for Ian M. Banks all felt very relatable to me as I’ve been dreaming of a post-scarcity world where my AI space ship friends shuttle me around as they pursue their inscrutable intentions. I want to sublime. Maybe not for a few thousand more years though. But I want to make it through the singularity to the other side, or at very least avoid dying in William Gibson’s jackpot. I feel like you get what apocalypses preoccupied my mind.
Most of my fantasies and fears have been touched by my love for science fiction. I saw in you someone who saw the same possibilities as me. You were very much one of us.
I also see someone being used for their dreams. They are harnessing you and your power to drive the rest of us to focus on their nightmares. Don’t let them steer you.
But your posting is reaching people. It’s annoying to some, but it hits. Maybe it hits too hard. But the isolation I imagine you feel isn’t necessary. Power laws can separate just as effectively as they bring us together. You don’t have to be surrounded by reply guys. There is a path to connection even for the most singular among us.
Now of course, I want something from you too. I want you to get us off this rock before it’s too late. I know it’s a big ask.
My best is advice is to go reread Excession and get yourself out of this persistent “fight or flight” cortisol pump. Get focused back on the shit that matters. Maybe find yourself a nice autistic sociopath who will love you for you. Maybe she can protect you from some of the pain. I’m sure you will figure it out.
I want you go to therapy. Mine is pretty good if you’d like an introduction. She’s an aristocratic 80 something Swedish woman, so you might like her. She’s perfect for working through attachment issues. She’s quite good at dealing with poor little rich kids with mommy and daddy issues. Her neighbors are all billionaires so she won’t be impressed by your bullshit. She has a sub-specialty in sex so she can probably help with that dick riding problem too.
And most importantly, she’ll be the only person who doesn’t want anything from you. And you need that more than anything.
Working on a Wednesday is expected. Working on a Sunday is a transgression. And like all modern transgressions, working when you aren’t supposed to be working is now a desirable thing. When work becomes a rebellion, strange things happen to your life. I think magic happens.
I’ve excited for the dead time that the end of the year brings for work. Because it’s secretly one of the best times to get shit done. I am never more productive than when I’m expected to be at rest.
In America, there is an expectation that we take some of the time off between Christmas and New Year. But the time off grows and suddenly no one is expected to get anything done for two whole weeks. And then it’s just a mess of resentment where we are at work but not getting much out the door. It’s such a waste. But as soon as people are actually off the clock. That’s when the entire energy of the situation changed.
When everyone is out of the office, is the best times of the year to sprint ahead. Maybe it’s that when people are off work officially they are more receptive to new ideas. They are less on the clock and can take more chances. It seems fun to check your email after too many hours with family where no one shares your interests.
But trust me people are looking for an excuse to do deals when it’s taboo to be working. It’s as tantalizing as getting a message from someone you want to bone. Look at you doing this thing that is a little bit naughty. What a secret you have getting work done when social convention demands we be with family.
So if you get an email from me during the holiday season know it’s because I’m having a blast. You might enjoy responding. Who knows what kind of cool deals we get done when no one else is hustling.
I think I might be living and participating in corporate and cultural warfare. Which is the most cyperpunk dystopian thing I can imagine. Which automatically makes it a little bit cool. But I really do think we are being drafted as a stan army of useful idiots in the culture war that has hijacked the meme space in Elon Musk’s brain.
Our most brilliant entrepreneur and erstwhile scientist reaching for the stars is now fighting a battle against attention whores. And I guess that’s how we fund things in late stage capitalism. It is honestly very cool even if it is very scary.
I know we have all read Ian M Banks. We love the Culture. Bring on AGI! Fun fact, Elon Musk’s family trust is called Excession. That’s the book I read on vacation every year. Clearly I have a lot of the same interests as the guy. So I get it. We want Elon to win.
But our boy is fighting some fights he might not even be aware he is in. He being used. He’s been recruited for a host of interest groups to launder some of the weirder corners of Reddit.
One narrative that outlines this agitprop civilian targeted skirmish is that Musk is freeing us from the tyranny of wokes. He represents the the real Americans populists who like goodness, dynamism and slightly dehumanizing working conditions.
And also somehow it involves grooming and pedophilia. Meaning that QAnon has come for Silicon Valley. So I’d be going to ground if I were a target, as you don’t want to be found by the crazies at the end of the internet. What Elon Musk just did to Yoel is at best naive and lacking impulse control, but at worst, puts a former employee at direct and extreme personal risk.
Silicon Valley used to be its own culture war. We fought for free information and open source software. We wanted cryptocurrencies and privacy. And now we have instead differing factions fighting for their own inscrutable means. Except maybe getting us to the singularity. I think he’s been clear on that. But beware fringe political movements flattering your ego. They just want your power.
I was having a conversation with one of my girlfriends today about power. We are both exploring the new ways in which we’ve become more aware of our inherent power. Not that we were not powerful when we were younger but rather we have a new consciousness about it’s responsibilities. And it’s relationship to our gender is complicated.
One of the most dehumanizing aspects of Girlboss culture was how it forced female founders into rigid standards of acceptable behavior and emotions. We were surprisingly heavily policed even though we were allowed to use femininity to allure and entice. Girlbosses were empowered. Except occasionally we were only empowered with sex appeal.
Girlbosses looked good on magazine covers and in lifestyle content. It was honestly suffocating even as it was a massive tactical advantage. Imagine being given a cheat code or a level up. Of course you are going to play it but sometimes it takes the joy out of the game.
I am less adverse to the wiles of the feminine as I get older. Now I am able to wield the benefits of mutual viewpoints and seeking common ground. Women are trained to persuade from a young age. We are trained to be accommodating and without hostility or anger. It makes it easier for us to seek out where we might come together.
But those powers of persuasion can also feel manipulative and narcissistic. Men who have felt failed by their mothers can feel particularly hostile towards feminine power. Negative family orientations towards women from siblings to parents can sit in completely irrational and reactionary places for men. I say this because men occupy a similar place for me. Mommy and Daddy Issues can often materialize in stabilizing coping mechanisms. But ultimately it’s not a healthy exchange of power if it’s not consensual.
I dislike having power that I only wield because of my gender. I would prefer to have a less charged environment to pursue my fortunes. But I am also not adverse to playing my hand. You’ve got to play it as it lays. Different women have resolved these power discrepancies in wildly disparate ways. But we are not absolved of the ways in which we hurt men just because we have been hurt by them.
One of the great oversights of the feminist movements may be our lack of a developed gentlemanly style code for women. A theory of chivalry for not playing fair in the gender wars. We certainly expected it of men. If you wield power you must do it responsibly. Peter Parker principle applies to anyone with gifts that can be used for good or evil.
I spent the first decade and a half of my career as a founder. I am very good at certain parts of the job like creating momentum and getting attention. I am less competent at operations and logistics management. Fortunately I’ve always had incredible teams who managed me.
That’s right, I said teams who managed me. One of the dirtiest secrets my husband kept from me is exactly how experienced operators like him manage high octane founders like me.
“ We don’t take an action until the third time an ask is made.”
Alex Miller
Alex has had to manage some of the quirkiest personalities in startup land so he didn’t just develop this strategy with me. He has been using this three asks technique for a while.
Initially I was extremely insulted when he revealed this was standard operating procedure for dealing with founders. How dare he not do what I request. I did a little ego protection. But then I realized he was right. Founders have to be managed carefully.
Momentum machines without any friction can quickly spiral out. Knowing exactly how and when to apply friction is the real trick. Too much and nothing will get built, but too little and your team can’t get a grasp on where to focus.
Many founders are extremely charismatic people. Their entire job is to get you excited about doing the impossible. And because sometimes we discover that the impossible is indeed possible we often wrongly assume if someone tells us “no” we’ve absolutely got to prove them wrong. We are always trying to generate momentum towards what excites us most.
Alex wisely doesn’t ever tell founders no. He actually encourages you to figure out if you really want what you asked for through his three asks technique. He gathers information. He asks what you are really trying to accomplish. He asks about specifics and technicalities and details. He gently coaxes out the underlying reason for an ask. He gathers information better than anyone I’ve ever known.
And what really drives me nuts is that this system works. If through the process of information gathering the founder continues to insist that something should be done Alex will organize all the details he has gathered in diligence. He will present the information and wait for the founder to ask a third time. If that third asks comes, only then with all the information will he organize the executive team together decides to proceed and make sure the founder is ready to accept the plan.
The genius in this method is that founders have an excellent gut sense for direction and momentum. But because it isn’t our jobs to actually make it happen we can often be total idiots about the resources required and the hidden land mines. By managing both the founders desire for an outcome with the realistic needs of the business, you almost always avoid pursuing the bad ideas.
If you work at a startup, especially directly with a founder, I’d strongly advise implementing the three asks method. You won’t go on nearly as many wild goose chases but so long as it’s done with empathy and tact you will still benefit from your founder’s natural momentum.
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.
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!
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.
