Categories
Emotional Work Startups

Day 719 and Step By Step

I was discussing my goals for 2023 with a friend today. They wanted to know if I was planning on making any New Year’s resolutions. I told them that I wasn’t in the habit of using a new calendar year for making big changes.

Generally speaking if I want to do a thing I just start. I honestly feel like it’s far too intimidating to declare yourself to be some kind of fundamentally new person that will, as of a certain arbitrary day, make huge life changes. It’s too much pressure. One of my rules for biohacking is to only change one variable at a time. And I don’t make big changes to it either. 10% a week is good enough for most goals. Anyone familiar with the magic of compounding knows that small changes add up to big numbers.

Which isn’t to say that I haven’t started big life changing projects on January first. If you count back from 719 you will notice I first began writing on January 1st 2021. I did indeed resolve to write every day. But I hadn’t intended it as something I’d keep up for a specific amount of time. I’d hoped I’d practice my writing for thirty days and I allowed myself a little fantasy about how amazing it would be to write for a thousand days.

A thousand days seemed like an impossibility at the time which is why I allowed the fantasizing. My pragmatic side said just get started and see if you can keep going. And I did. I put one foot in front of the proverbial other for two years. Now I’m relatively confident that if I want to do so I’ll make it to a thousand days.

I approach most goals like this. I had a fantasy that I could make it as an investor. I was a founder so I thought let’s wire some small angel checks. We were already committed as a family to being startup operators so why not combine our skin in the game with a little more capital risk with our network.

I never envisioned myself raising a fund and making some big announcement about how I had a venture fund. I just started learning by doing. I cut checks. I ran some special purpose vehicles. And this year I decided to one-step-at-a-time go about raising a rolling fund. I am just doing the thing one day at a time. And it’s going well. Amazing people are coming on board. I am confident I’ll reach my goals just by putting one step in front of the other.

If you’d like to join me my goal is to raise $500K per quarter. I’ve got folks like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company. You can read the fund overview here. Yoican sign up on Angellist through the above link or get on a call with me and we can discuss the fund, our portfolio construction and my thesis. Because I intend to work through the holidays because it remains one day at a time.

Categories
Emotional Work Internet Culture

Day 711 and Excession

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.

Never meet your heroes. Everyone is just people. Now I’m worried I’ll die here on Earth filled with grief like Captain Kirk. There are no dicks left to ride once you realize we are all just humans.

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 Ukraine
Here 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.

Categories
Aesthetics

Day 705 and Impressed

I haven’t bought a new handbag for nearly a decade. While I like fashion I have never been a hardcore accessories person. One generally been of the mind that those are anchor pieces that you keep for years and years. I didn’t see much point in acquiring trends as it just seemed so expensive. I buy more for longevity.

The last handbag I bought was a camel Masur Gavriel bag. I think it was sometime in 2013 but it may have been earlier. I found a photograph dating it no later than 2014 but I can’t be sure. I’d seen a small piece of press about it as it being a kind of super minimalist brand by these two bicoastal pretty girls. I loved the clean look of the tote with a long full leather panel and a bright yellow sunny interior. I found a boutique that stocked it in Los Angeles. I think I paid less than $300 for it.

I’d talked it up to a girlfriend in finance and she bought one. She then talked it up to her friend who happened to be Lauren Santo Domingo and then next thing I knew the nag was absolutely everywhere. It subsequently raided a large private equity round. It’s brand book became so popular a fast casual yuppie food brand called Digg Inn ripped them off. The brand was a genuine hit.

Being ahead on a handbag like that is the fashion equivalent of being in the best series A round in Silicon Valley as the new angel investor. It means a lot but only after it’s been proven out to the IPO. I haven’t felt that kind of kinship with a brand in a while. And certainly not with a handbag. The high conviction I had with Mansur Gavriel should have made me pursue the two designers as I just knew in my gut this bag was fucking it. Really the one that got away for me.

So I am excited that I got a new handbag today. The first one I have purchased since my Mansur camel tote. I’ve literally not purchased a single handbag in that entire time though I did buy a backpack and a suitcase.

I saw this across it across a bunch of fashion blogs over the year. It has hit a lot of mainstream fashion news. So fashionistas are definitely well and truly ahead of me. I am not a market editor or an influencer being sold by fifteen different publicity firms. Though I’d absolutely like to be. There was absolutely a time when I was very much in the scene but let’s be real now I’m an eccentric investor in Montana. I’m cool just in a different way.

Polène Numero Uno Mini in Black Lizard with dust bag.

The bag is called Numero Uno Mini from a French label called Polène. It’s a clean bag. But it’s got a little personality in it’s shape. There were smooth calfskin options but I’d been searching for a modestly dressier bag that would be a bit of a statement for day but also formal enough it could accompany a cocktail dress or make due at a wedding. It works up until you need a clutch because it’s a gala or an awards ceremony.

Polène Numero Uno Mini in Black Lizard with dust bag.

I feel like it’s a bit louder than the bag it’s replacing which was a black calfskin envelope clutch with a gold chain that is bought from Barney’s. I’d got it on sale for like $150 bucks as well it was a house brand I guess. But it was just so damn versatile I used the fuck out of it. I haven’t seen it since we moved to Montana and I’m a bit concerned it’s gone for good. So perhaps this new Mini will find a home in my routine.

I’m very impressed by its quality. The stitching is tight and lean. The hardware is bright and sturdy. The logo is very discretely etched into corners of the hardware and on the feet of the bag. Which is just a nice touch at a $350 price point. Recently it’s felt like everything is a bit shittier and more expensive. So it’s a joy to get something that feels like a great value and genuinely nice. I hadn’t made some dirty compromises with a direct to consumer business. So yeah I’m impressed with a handbag.

Categories
Culture

Day 697 and Chivalry for Women

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.

Categories
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!

Categories
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.

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
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.