Running a startup, for all its supposed glamour, is mostly an exercise in learning how little you know.
Sure there are playbooks for some of what you will do. As the technology industry has grown and startups have become an appealing career choice we’ve filled out how-to guides for everything from fundraising to operations.
Alas all advice is specific to the giver’s experience and untangling biases to make advice relevant to your specific needs is quite hard. That’s where it helps to have more experienced operators on hand to call bullshit.
At chaotic.capital we pride ourselves on being investors who “have a guy” for even the most esoteric possible requests. Playbooks can only you so far when you need an expert.
Just in the last two days we’ve worked through how one hires a chief of staff, what to do when letting go of counsel who made a mistake, installing appropriate security procedures for digital footprints, and the resale brokers for a rare commodity.
We like to problem solve and the weirder the problem the more fun it can be. Removing obstacles and clearing bottlenecks is satisfying work. And knowing guy who knows a guy is a heck of a fun game of social geography.
I’m in a terrific mood. Maybe it is just the hormones cycling up. Maybe the red lights we installed in the bedroom are actually improving my sleep quality. Maybe it’s getting a foot of powdery snow over the weekend.
So much of life seems to boil down to manage my own circadian rhythms even as I plug myself into the hiveminds of my favorite corners of the internet dutifully everyday. And my body likes short days, long nights and the bitter cold.
Certainly success is contributing to my buoyant mode. All of my founders are soaring (which seems statistically rather unlikely given the choppy markets) and the vibes are good. My chaotic.capital clique is thriving.
It’s getting to the point where I think we should host a portfolio dinner or something. Though that would be challenging as we are a distributed group. Alex realized recently that we only met one of our portfolio founders in person before we invested. Can you even imagine that in a pre-pandemic world? Our deal flow comes from the virtual worlds I live in daily.
Being snugly ensconced inside several areas of with macroeconomic tailwinds doesn’t hurt but most of those choices were made two or three years ago so I’m simply directionally correct, well connected, and unafraid to commit once I’ve satisfied my own process. Everyone has a long way to go but it feels wonderful to enjoy their success.
An offensive “joke” I learned from my favorite trainer when I was a powerlifter contains a simple truth.
You should only ask a former fatty for exercise and nutrition advice.
The reasoning is simple. The naturally slim and athletic never had to work for it and as such don’t understand the struggles of the average person.
As someone who has metabolic challenges I feel reasonably strongly this is correct. Struggle that leads to success has useful lessons that ease and natural talents doesn’t always pass along
It’s with this in mind that I sometimes hesitate to give cosmetic advice despite my professional experience. I had some teenage acne and an enormous struggle with eczema on my body. But everything from the neck up has been a breeze.
My face has been clean, clear and even at 40 largely wrinkle free. My hair grows down my back like a hippie. I can get past an optimal place with relatively little work.
I say this not to gas myself up, just that I don’t fully understand the struggle of problem skin or hair. So if you really struggle I’m not your girl.
And yet I get asked a lot about cosmetics as people presume I got my results from hard work. Thats only partly true. Some of it is just good genetics. I’ve got plenty of other genetic dings so I’ll take the good luck.
I do however maintain a very consistent routine and understand the inputs that lead to my desired outputs.
Getting yourself to a Pareto optimal place doesn’t require anything terribly elaborate or even expensive. Women’s magazines and Sephora may make it look impossible but heed the words of Elle Woods in Legally Blonde.
The rules of haircare are simple and finite. Any Cosmo girl would have known
There are basic rules for skin and haircare that you can follow diligently and at relatively low cost. If you give some basic inputs about your skin (is it dry or oily) and give me a budget I can get you 80% of the way there if you simply follow some basic steps everyday.
Marcia Kilgore of Bliss and Beautypie fame has a terrific memetic device I repeat to everyone.
ABC + SPF.
Vitamin A (retinol) plus Niacinamide (Vitamin B) and Vitamin C is all you need along with a sunscreen. The optimal order is a retinol moisturizer at night with a day moisturizer that contains B & C vitamins along with a SPF.
Now you can gussy that up a lot with dosing, adding in more acids if you have oily skin or ceramides and peptides (which I do as I have dry skin). I myself take a collagen and biotin supplement for some additional help. My expensive piss post offers some additional supplement options that are worth it if your nutrition isn’t perfect. Obviously you need to sleep and drink water.
Beyond a night cream with retinol and a day cream with SPF you can get more elaborate. There are manual processes for microdermabrasion, red light devices, Botox (I just started at 40 with about 15 units while the average is more like 70) as well massaging techniques and needling techniques. I think it’s overkill mostly especially if you don’t have good habits in the first place. Check your foundation before doing renovations.
If you just do the basics morning and night consistently (which can be fit in one or two products) you don’t shouldn’t to go hard until nailing the basics.
Unless looking good is a professional obligation it’s wasted time and money. Just do the basics. If you need product recommendations I can do that at any price point from drugstore to the luxury houses. It’s obviously a lot of fun if you are into it and I am so just hit me up.
It’s a nice number for today’s post. A strange countdown inside one day. A little spooky. Maybe also some good luck. Fourteen. Thirteen.
I am tabulating much more than my days of writing in a row or any particular numerical significance that this position of numerals might show. I’m adding up our position and deciding how to play our hand.
There is simply so much to consider. I feel it in my joints. Maybe that is evidence of acceleration. All I see and hear is speeding up. Are you accelerating anon? Maybe that’s the pressure in my joints and it’s arthritis at all.
I have felt a bit sick to my stomach and I’d prefer to blame it on delicate lady things. It could also be nausea from the spin cycle of all that “much to consider” of the moment.
I’m glad I’m ensconced in my winter farmhouse. The numbers go up. The game’s whirlwind spins. There is much to consider.
It really ruins your appetite this whirling. The ride up the rollercoaster. No wonder Alice in Wonderland commercialized into whirling teacups at Disneyland. Can’t have it be the symbolism of opinion and fuzzy opinions.
So there is much to consider as we whirl like dervishes into the next moment.
I am just enjoying our first frost here in Montana and yet I’ll be pulled down too soon from our wonderful fall. All to enjoy hot takes and hot climates. I don’t like hot climates so I guess I’m going for the takes. Founders and LPs (and those with opinions on LPs) are priorities.
If you will be in Miami attending the conference I am hinting at please do look me up. The weirder the better. I’ll also be accompanied by my better half Alex Miller. Come for the tractor discussions and stay for the semiotics discourse.
Apparently there will be a costume party but one can simply choose black tie. One thing I like about it Miami is how it celebrates dressing up. I can wear a billowing pink gown or a dolman sleeve full length velet fishtailed dress and not be out of place. It’s just very tropical.
I think I’ll enjoy packing simply because it’s nice to have an excuse to wear white sneakers and floral robes. I can even get excited by doing some fun makeup. You have to live joyfully when the theme is the apocalypse.
She works to convince the reader that actually the most libertarian and individualistic demographic, who regularly decries state power (especially its use of coercion to drive censorship, limit transactions and restrict compute), are in fact, actually vouching for totalitarianism.
Even the graphic hints at the supposed appreciation of neo-monarchy as a nod to nRX intellectual Curtis Yarvin.
I fear she firmly missed the point of founder mode for her insincere political framing. Despite her clear understanding of our values.
In that original recipe, venture capitalists invested in founders rebelling against established hierarchy and building great products. And when those rebels themselves became too hierarchical, venture capitalists turned to new founders aspiring to overtake the old order.
She is right about we prefer to work as an industry and how we see our efforts. “Many of Silicon Valley’s greatest products were originally intended to liberate, not to control people.”
And yet missed she missed that founder mode is about liberating our founding teams from the suffocation of professional management. It’s got nothing at all to do with justifying tyrannical founders.
Larger firms have a pantheon of corporate departments to ensure smooth governance from legal, to HR, to corporate communications in order to comply with state expectations.
As regulations have ballooned so too have the specialties required by the middle managers. We must be in compliance. We must take everything and every view into account. We must do things by the book.
Founder mode isn’t about running ripshod over your people. It’s certainly not about Trumpian declarations of what must be done. She’s absolutely correct that “emotional dysregulation, bullying and bloviating are not leadership attributes”
I find her criticism to be manipulative insincerity. She’s deliberately missed the point of the original Paul Graham essay, inserted her own political insinuations about how Silicon Valley is hiding their true preferences for authoritarians while herself advocating for a pass the buck culture. It’s not fit for Radical Candor and I’d expect better from someone of her stature.
Life has been on a wonderful trajectory for me over the last four years. The pandemic marked breaks in everyone’s lives and the chances we were afforded to shape our lives was a privilege in a disruptive and challenging time.
Others took similar leaps of faith into new ways of living. So as I celebrate my birthday today I feel such gratitude. I couldn’t ask for a better turn around the sun.
We had a life changing exit and a series of investments go our way, I made my way into inception & pre-seed investing with our pre-seed fund chaotic.capital, and we moved to Montana. It’s all amazing especially as it’s had its struggles with my health.
I am being offered a season of life where I feel like I can really contribute my skills in professional ways that could be impactful. Everything I’ve built towards and all of my interests and hobbies are tying together in amazing and exciting directions. A happy birthday to me for sure.
If you are in New York City I’ll be flying in this weekend for a week in the city. I’d love to meet founders, other investors, and startup folks in general. Also if any weird Dimes Square reactionaries want to meet up I offer parlay.
There is a beloved meme in communities like YIMBYism (a movement advocating for building more housing with the slogan “yes in my neighborhood”) in which the protagonist agonizes over subsidizing demand as the cyclical pattern of rising demand giving rise to rising cost carries on.
“I just need to subsidize demand”
America is a strange place where we espouse a lot of free market policies but we tend to favor subsidies as a solution. Which isn’t always a bad thing. Sometimes there are good reasons for providing support for things that aren’t as commercially viable immediately like pure science or education or other public goods.
It is however not the only policy tool available to people. A fun fact about how I have a good time, my participation in civic life was as an appointee on the New York City Community Boards. I was part of a group who approve licenses and permits for things like liquor and parades and the like. I also served on quality of life and transportation boards. I also did monthly meetings for land use.
I was easily the youngest person who volunteered time and I learned a lot about how damn many rules we have at every level from neighborhood to city and state on everything from ventilation and to environmental review. And some of those rules are pretty good things!
But it would be preposterous to say that all rules are good and that every part of the process of starting a business (large or small) is easy. Some problems you can’t through money at and fix. Or if you can it creates a whole unintended set of other problems. Like paying for lawyers and consultants.
Because Twitter is the land of any old idiot getting a say (just like a community board meeting) I’ve got every flavor of opposition and missing the point on this tweet.
We do a lot well in America. It’s relatively much easier to start an LLC and get a license to do business. Complying with everything from the liquor board to FinCEN will take a little more. Anyone who has run a business can tell you about their corner of the universe and the paperwork involved. Just ask my husband who spends most of his time as a businessman keeping up with paperwork.
I think it’s perfectly fine to be skeptical that throwing more money at a problem like how challenging it is as a business owner to contend with government bureaucracy. Demand subsidies can only fix so mich. It’s just a lot more complicated than that. Be smart and don’t let your head spin like our meme gentleman.
I do pay attention to politics alas as I am involved in a number of issues (#FreedomToCompute, regulatory reform, and housing) so it’s easy to over do it with being extremely online. My nervous system doesn’t need any additional stimulation.
I was relieved to be back on my feet today as it felt good to be heads down at work. I’m excited about how my seed investing has been going over the past few years and I’m taking the next steps to evolve the fund. I’m so optimistic about what can be achieved. Founders are particularly motivated to build. Ingenuity sparks when things are darkest.
I’ve begun booking some of my fall travel. Much as living the good life in Montana is pretty much paradise, one is obliged to make pilgrimage to the main cities in which business is done.
Some juggling of priorities will be involved as Asia and Europe compete against home turf cities like San Francisco and New York. Plus we have conferences in some pretty weird places from rural Wyoming to South Beach Miami.
I am resting today and enjoying running the logistics of the fall season through my little packing and organizing rituals. I enjoy thinking through the logistics of grooming and dressing more than I do working through the health and medical routine.
It’s nice to daydream about the cold fall. I put on a cashmere sweater and pulled out my bags as I thought about the return of the cold and the return of work. I can’t wait. I better catch up on sleep while I can.
