Tag: Silicon Valley

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Finance Startups

Day 149 and Optimizing for Outcome

I came across a thread today by Sahil Bloom on human goal setting and the mental models we manipulate. He introduced me to Goodhart’s Law

When a measure becomes a target, it ceases to be a good measure. If a measure of performance becomes a stated goal, humans tend to optimize for it, regardless of any associated consequences. The measure loses its value as a measure! Goodhart’s Law is states “Any observed statistical regularity will tend to collapse once pressure is placed upon it for control purposes.” But the concept was popularized by anthropologist Marilyn Strathern. She generalized the thinking and called it Goodhart’s Law. “When a measure becomes a target, it ceases to be a good measure.”

I am fascinated by this tendency humans have of fixating on the things we think symbolize progress instead of the actual outcome. Sahil names a number of instances in which this has led to bad business outcomes. CEOs managing to short-term stock goals has been one that has long frustrated me.

Startup land is immune from this tendency either. I’ve seen product teams fixate on OKRs such that they never miss a single metric but fail to launch their product on time. Or a venture capitalist will toss out something like an ARR goal for a Series A only to have a founder chase that number for a year and still not get funded when they hit it. We think these goals are the goals in and of themselves. But really launching the product on time and closing the series A are the only thing that matters. As long as we hit our goals who cares what metrics we used?

This is of course set against the classic “what gets measured get managed” which is an apocryphal quote from business theorist Peter Drucker. It may in fact be total bullshit. It may be that measurement actually hinders management. Said rather well by Simon Caulkin

Measures set up incentives that drive people’s behaviour. And woe to the organisation when that behaviour is at odds with its purpose.

Lest you worry this is just a business problem when I was single in my twenties I made a spreadsheet of the various gentlemen I was dating. I felt like I needed a way to make the process more efficient so I starting weighting categories of characteristics that was most important to me. I like intelligent men so I started listing their college degrees. I liked men who were into quantitative thinking so I started noting if they worked in banking or academics. And well you can imagine how this took a turn for the worst. Instead of meeting smart men that likes to look at the world through numbers I met a lot of bankers that went to Harvard. I was optimizing for the wrong outcome.

Next time someone tells you that some metrics or goal is the only thing that matters stop and question if it makes sense for the long term objectives. I’m not saying bankers from Harvard aren’t smart but I’m also not saying that all smart men are bankers from Harvard. And that turns out to be a pretty crucial difference.

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Finance Startups

Day 146 and Gossip

Gossip drive the world. The stories we tell about other people reflect a lot. Even if we claim we don’t care what others think what others think moves the world around us. And I would posit that this actually isn’t a bad thing. It can drive closer bonds and increased connection.

There is a concept in evolutionary psychology called indirect reciprocity. Natural selection favors strategies that base the decision to help on the reputation of the recipient. Social interactions in which one actor helps another and is then benefited by a third party are key to cooperative reputations.

This isn’t just a systemic population level issue either. People who are more helpful are more likely to receive help. It’s uneven obviously and people can obscure their reputation. Depending on if you are up or downstream of helping or being helped, you make different calculations. Some people help more but they feel it’s worth the cost. They are downstream. Others accept more help because they are upstream. We are all making trades based on our position and arguably they are fair market trades.

How we decide to cooperate and with whom is driven considerably by reputations and shared value beliefs. Relaying reputation signals to bolster your capacity to connect to others is actually a key part of empathy. We need to establish psychological safety to partner with each other. Gossip helps us find suitable relationships. This is especially true in disciplines which require creativity. Quoting myself on the topic of psychological safety in venture capital.

If entrepreneurs are solving entirely new problems with high chances of failure feeling like they can trust their financial partners should be a top priority. Yet the atmosphere of distrust is pervasive. Venture capitalist and entrepreneur are constantly managing the information flow between each other.

Managing the information flow is a key component of gossip. Showing you understand their context, their fears and their reputations concerns helps you. An act we denigrate in popular culture actually helps you to deepen the relationships as each signifier breaks down space between two people and builds trust. So don’t knock gossip. It has evolutionary, societal and individual benefit. Just remember the ultimate outcome is about bringing people closer.

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Startups

Day 144 and Scars

I have significant e-commerce, direct to consumer and retail business experience. I’ve managed multi-million dollar P&Ls, worked on iconic billion dollar brands and started my own direct to consumer cosmetics line. You’d think with that experience I would be deeply bullish on my ability to pick up and coming startups in the space. But I don’t particularly want to invest in digital brands or online retail. And I think it’s scar tissue.

I’m not saying flat out“no” I won’t ever invest in a DTC business or an e-commerce startup (I have and I will again) but a little bit of knowledge can make it hard to preserve creativity and imagination. Many founders can come out of a space where they have dedicated years of their lives and simply want space away from their expertise. They know too much. They’ve seen things. The scar tissue that forms to keep you working during the long dark soul of startup pain is still tender.

When I mentioned this lingering pain others pointed me to other areas they struggled to hear pitches or invest because of experience. Rental businesses and neobanks from Maia Bittner, certain e-commerce verticals from Lee Edwards, fitness from Jason Jacobs. It’s a common phenomenon among founders.

I’ve got lots of opinions why certain kinds of businesses won’t thrive or have business models that won’t make the kind of return my own personal investing thesis demands. But the truth is that I now have enough expertise to simply know more than is good for me. Ironically this means I should spend more time as an advisor or consultant on certain kinds of businesses but it takes a special founder to coax it out of me. Because I do have valuable insights and I want to share them.

But the last thing I want to do is pass on the trauma of my own experiences. Founders deserve to have their psychological safety preserved so they can build the company of their dreams. Some painful insights from a founder that came before them might help them avoid some pitfalls, but if they take our traumas too seriously they may never find their own path. And that kind of backward looking “it will never work” or “trust me kid I’ve been around the block” attitude can really bring creativity down. So I will always share my honest experience with anyone who asks but I’m hesitant to ever let anyone take my lessons to close to heart. You very well may be the one that breaks through where no one has before.

So when someone pitches me their new retail startup or DTC brand or cosmetics concept I try to be honest that I may nit be the best fit. I’ve got scar tissue. And if a founder insists that I can help I will try. But remember not all skepticism, fear, distrust or dislike is about you. Sometimes it’s all about the trauma of having lived it before. Asking someone to live it again is the ultimate act of trust. And maybe just maybe we get to firm new scar tissue together.

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Finance Internet Culture

Day 136 and The Ease of Centralization

We are a few days into a news cycle where Elon Musk’s corporate socialism interests and/or environmentalism has pushed the Bitcoin discourse to a fever pitch. I don’t begrudge Elon because it’s hard out there for someone who takes government subsidies and we’ve all got to lean into our economic interests. The renewable energy credit system is a policy choice and my neoliberal friends would argue it’s a good one. It’s also one that currently pay’s Tesla’s bills.

Tesla makes most of its $ from RECs, not cars. Last year, it made $1.58bn from sales of RECs to gas-powered auto companies (which must buy to offset their CO2 emissions). Tesla has never been profitable without REC sales to bolster its auto margins.

That’s about to change. Last week, @Stellantis (i.e. PSA Group + Fiat Chrysler) told @LePoint it’ll meet carbon emission rules this year. That means it won’t need to buy RECs from $TSLA anymore.
Fiat Chrysler accounts for $2.4bn of Tesla REC sales from 2019 to date and 55% of Tesla sales since 2008.

What I think is really interesting is that Elon DOES know a lot about money, in particular the benefits of a centralized trusted player. Which he himself points out since you know PayPal. Centralization has been pretty crucial to fast efficient financialization especially in modernity. Of course that has some downsides as institutional power tends to accrete. Good and bad amirite?

The exciting thing about cryptocurrencies is that they may offer us they same scale as global institutions but without the whole plutocrats and fossilized bureaucracy part. Not that I’m advocating for Ethereum or Consyns.us but they put it well in the below quote.

Whereas our traditional financial system runs on centralized infrastructure that is managed by central authorities, institutions, and intermediaries, decentralized finance is powered by code that is running on a decentralized infrastructure

We’ve got a couple decades of experience in computing on the challenges of decentralized infrastructure. It’s not easy and it has costs. The costs are both significant in time and money but the benefits are significant as well. I personally find the argument that systems which are not centralized are less fragile and it is worth diversification into systems that are less fragile. I often chose convenience and speed but I also put significant effort into having systems that can withstand crisis and disasters as well. Security has always been about trade offs. And cryptocurrencies, especially Bitcoin, is about making some trade offs in efficiency for the sake of hardening of financial system. I’m philosophically inclined towards this. If I’m trying to solve global warming and getting to Mars I might find this less compelling as I’d rather focus on efficiency. This is also why environmentalists make great villains as they decide on that choice for you. I’m not saying Elon explicitly going for Bond villain but it’s an aesthetic.

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Startups

Day 125 and Working With Startups

One of the most frustrating aspects of startup life is the vendor startup relationship. There are so many pitfalls and disasters that can befall each side. That naturally leads to a lot of dysfunctions as each optimizes for their own needs, a process that unwittingly leads to the disasters we sought to avoid in the first place by trying to prevent issues.

From a startup’s perspective there are two key issues. Established businesses tend to be slow moving. They are slow moving as they have process and documentation. Nothing is more frustrating to a startup than needing a nimble partner that can throw shit at the wall only to get a meticulous vendor that documents all the shit that didn’t work in exacting detail. This isn’t to say that one shouldn’t report (in a remote first culture documentation is even more crucial) but 40 page decks on what happened will send a founder running.

From a vendor perspective startups are frustrating because they never have any of the assets, documentation or processes in place that make your job possible. Anyone who has become embroiled in a mess of half functional SaaS operation software knows what I mean. How are you supposed to deliver on a contract when all the basics you need from a startup are impossible to locate and occasionally contradictory?

The tension between the two workflows is clear. Especially because startups eventually become more process driven and operationalized over time and vendors are always looking for ways to become more nimble and cost efficient. So you’ve got two parties who want to become more like the other, but as they do that risks upsetting the partner that chose them for the opposite virtues. If this were a romantic relationship it would be heading for a breakup. “You’ve changed man!”

My best advice to vendors is to be as flexible as possible with startup clients. The faster you provide an output the more likely it is that the founder will come to rely on you. Most successful startup vendors simply roll up their sleeves and start producing. They don’t scope in too much detail or negotiate contracts that lock them in, no, successful startup vendors know they give themselves security and contract stability simply by giving a founder what they need every day. As you find more needs you act on it. You stay flexible till suddenly you’ve become the crucial partner that gets budget every quarter. As a startup grows becoming the indispensable partner means that you grow along with it. Your goal should be to have your client succeed at the same pace that you are succeeding.

My best advice to founders is to allow your vendors best traits to rub off on you. Paying attention to their competencies allows you to build up teams that support that. That then enables your vendors to perform even better for you as the fluency on expertise develops. Great marketing teams don’t just produce great marketing in-house but rather they allow it to flourish in the entire ecosystem. There is a reason why CMOs have winning agencies and winning agencies have great brands. The truth is that you will always get the most out of your vendors if you respect what they excel at and spend your time and money prioritizing that support.

The danger if you don’t make productive vendor startup relationships is two fold. One startups will waste valuable capital with a partner that was never a good fit. Two vendors will waste billable hours and employee energy on accounts that have a high probability of imploding. It’s a waste of money for both sides. But when it works well lol it’s absolutely money.

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Chronic Disease Chronicle

Day 105 and Envy

I didn’t have hobbies for a long time. People would ask me what I did in my free time and I’d give them a confused look and try to come up with a plausible activity like reading. I was embarrassed. Everyone else constantly doing shit. In reality, I didn’t have the energy for anything but work and taking care of life basics (and for a few years spare energy was dedicated to sex and dating but that’s different post).

I’ve been an on and off entrepreneur my whole working life. And if I’m totally candid I’ve had health issues that impacted my energy since I was a child. So while I have had things in my life other people would consider hobbies, they were slowly stripped from me. I stopped horseback riding somewhere between 16-17 when I dropped out of school. I told people it was allergies (which was true) but much of it was exhaustion. I was fighting just to keep up with obligations to education like taking tests for college and to prove I had learned enough to be considered a “graduate” by my school.

In college I was blessed to go to a school that wasn’t cool to have have parties. That made it easy to hide being too tired to socialize. Other students were in clubs. I didn’t join anything. I was thrilled to make it to my job (as a research assistant to a medical ethicist) and get home to my roommate and boyfriend to watch tv at night. I didn’t realize this wasn’t normal at the time.

Once I started my first company all I did was work. I had to socialize professionally so I spent a lot of time at fashion parties. While this is fun it wasn’t a hobby. I partied because it’s how I made my living. For a while I thought this meant I had a hip social life. Which was a nice lie. I had a glamorous job.

It started dawning on me around 24 or 25 after I sold my first company and had to relocate to San Francisco for the acquisition that other people didn’t live like I did. In San Francisco people hiked, did yoga, took classes, and all the other “bullshit” I looked down on. I looked down on hobbies not because I think work is better but as a defense mechanism. I was jealous.

All these people had energy at the end of the day. They wanted to do things! That was unfathomable to me. I could barely do work. How the fuck was I supposed to do stand up paddle boarding on the bay? I was not kind to people that had hobbies. I told myself (and they could tell) I thought they weren’t as good as me. Of course, now I realize this was the trauma of illness manifesting it. I couldn’t do what they did. Rather than feel sad or angry or some other productive feeling I decided I was better. All to avoid letting myself feel how angry I was that I couldn’t have that life.

I’ve come to accept that I still live more than most people even with limitations like illness. I don’t have to prove a good life with status markers like hobbies. Though I’m still fighting to get to complete functionality and control with my autoimmune disease. But even if I do get to a place where I can live normally I might still skip the hobbies. I’ll go straight for the pleasures like work. I’ve only got so much time so I may as well enjoy each moment with what I actually like.

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Internet Culture Startups

Day 101 and Closed Ecosystems

The One of the most important novellas in the formation of my technical philosophy was actually written by a science fiction author Neal Stephenson. “In the Beginning there was the Command Line” should be taught in every history of computer science course. Go download it now for free and enjoy 70 pages of riffing on the utopian possibilities of open systems, the accessibility of closed systems and who is the ultimate winners of computing becoming a closed system (surprise it’s Disney).

The premise of the essay is simple. There are two core tensions in how computing has been distributed: open versus closed. The basic manifestations of which philosophy you pick have significant impact on what your users can build but also how accessible your machine or application will be to users. Stephenson focuses on the GUI or graphical user interface, perfected by the closed Apple computer universe, and how it has made computing infinitely more accessible to the masses while also taking away some of the power and flexibility of the original command line interface of prior generations.

In the battle for powerful and hard versus easy but more limited, Americans chose easy and the rise of the GUI began. Dicking around with your computer, let alone your phone, almost isn’t possible without graphical representations of computer programs. Even though said programs are ultimately manipulated several systems down on a command line (you know the “hello world” text interface you might have seen on some NCIS dad cop procedural hacker show) most of us have thoroughly bought into the desktop metaphor of the original Apple GUI. And yes this is old news. This problem of the GUI got won in the eighties. But the basic problem of open versus closed still rages on with us.

The current debate is most vivid on in the financial world with crypto, Bitcoin and decentralized finance as we all yammer on about DAOs and NFTs. But you see it in social media as creators become locked into closed platforms from which export of their content is almost not an option as without distribution and audience access their work means nothing. Creator economy businesses can make money from individual closed platforms but struggle to build businesses as they are too tied to one type of revenue stream. If they are big on say YouTube or TikTok but can’t take their audience elsewhere that’s an issue. Imagine a world where they could take their business with them not be locked into one revenue stream for a platform they cannot change.

What I’ve written here is more like an appetizer course for the philosophy debate and not an argument. I have an opinion in the debate which is that open ecosystems are better for more types of people but I’m also writing this on an iPhone. But I’m writing using WordPress on my own domain rather than choosing a closed platform like Substack. So it’s not exactly a simple binary outcome for anyone ever. Which is all the more reason to go read the novella now.

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Aesthetics Chronicle Startups

Day 99 and Swag

My favorite item of clothing in the pandemic has been a Facebook hoodie. It’s the perfect garment for long days indoors, not too heavy but not too light. It zips so it’s easy to get on and off. It has pockets for stowing my iPhone. It’s got a snuggly fuzzy inside but a smooth cool texture outside. I’m not sure I’ve been more dedicated to a piece of clothing.

Years of living in New York, where dragging dirt and debris in from the city was a real concern has made me a almost compulsive aficionado of “indoor clothes” which were not besmirched by the grime of subways and pavement. My Facebook hoodie remains my default “indoor clothing” top layer. At night I unzip it and place it carefully beside my bed. In the mornings if it is cold I put it back on before starting my day. The chances are good that if you’ve been on a Zoom call with me I’ve been wearing this hoodie. It’s just on screen and a strange affectation for someone that has literally never been a fan of the traditional Silicon Valley boy wonder aesthetic. The only item I have gotten more wear out of is a pair of Gucci boots I’ve owned for 12 years now.

To say that they are very different garments is an understatement. One is a thousand dollars worth of black Italian leather crafted into the Platonic ideal of day boots. They are feminine with tight knee high lines that maintain the slightly militaristic echo that typify the Italian school of fashion. The other is a baggy slouching genderless sack of blue with an embroidered white logo that splits with a zipper tight down the middle between Face and Book.

You would not imagine the owner of one garment was the owner of the other. Even when the tech plutocracy decided it wanted to play with high fashion status games (thanks Marissa) the two stylistic poles never really gained much common ground. Still tech has inspired a significant portion of modern fashion and fashion craves the semiotic power of Silicon Valley. I’m sure Willian Gibson could explain the common lineage but I doubt I have the chops. Nevertheless I do consider both pieces to be emblematic of my personal style. Something about utility I suspect. The two garments are not from entirely different worlds

Ironically I don’t use Facebook anymore (though I still have an account) and I don’t even support what the company has become. So you might think it’s odd I own a piece of swag from the company. I got the hoodie after I had already given up on the place. But I got it from a Facebook employee who I consider to be one of the best humans I have ever known. His name his Dan.

I didn’t ask him if I could write this little remembrance so I won’t give his full name. Thanks to the efforts of one of my investors he was an advisor and investor to one of my startups and was unfailingly the kindest person I had the privilege of working with. On a trip to visit him in Menlo Park he took me to lunch on the Facebook campus. We had tacos. Afterwards as we were walking we passed the swag store. I said that I thought it was a brilliant bit of marketing that they sold hoodies. Pop culture has long cemented the status of the hoodie with both the company and with founders in general. To have a specific Facebook hoodie seemed a powerful talisman filled with irony and hope. Without missing a beat Dan bought me one.

There was no way of knowing at the time, for either of us, that this garment would end up a significant figure in my daily routine. It remains an emotional link to Dan and the support he always showed for me. He never wavered in his belief in me. This is a trait he has demonstrated consistently with those in his life. One particular example is a dear friend of mine who worked at Facebook thanks to his efforts. She is also brilliant and kind and at the time Dan worked with her the victim of a deeply Silicon Valley crisis. The kind you might even associate with tech bros who wear hoodies with logos on them. An irony that is not lost on me. The tech industry truly contains emotional multitudes.

I’d encourage you to inspect the garment in your life that holds the kind of significance and emotional resonance that this hoodie does for me. Fashion exists in even the places we think are furthest from style. Like corporate swag. Like a Facebook hoodie. There is always a story and a reason behind what we wear. Indeed this was a topic I thought I’d make my life’s work when I first stumbled onto the internet. I kept a fashion blog on WordPress maybe starting in 2004 or so. I didn’t end up being a fashion critic. But I still get to blog about clothing if I feel like it.

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Finance Startups

Day 96 and Founders Who Don’t Want to Be CEO

My Twitter has been going viral with reply guy friendly topics like taxing high earners and public vaccine demand so I needed to get some niche startup content in today to clear my palette of the reply guys. So I’m going to think about founders, professional management teams and venture’s role in supporting founders. You know, a topic that won’t have strong feelings.

A non zero number of my founder. friends would probably pay to be extracted from certain stages of startup growth, especially later stage scaling, but somehow being founder friendly has come to mean keeping these founders in charge all the way through. Many excellent zero to one founders have to actively change their entire style, skill set and value proposition once they get a company past about employee 25. Obviously there are many inflection points in startup growth and many founders relish the opportunity for constant skill growth. But plenty of early stage founders hate stuff like Human Resources and operations. Shit a good chunk hate sales and marketing too.

Early stage work is a speciality. It’s a professional niche and hard to train folks for as it’s part personality and part dysfunction. I think we should value early stage founding for its disproportionate impact on value creation instead of forcing these early stage specialists to train to become generalists, great managers or scaling operators. Of course it’s more likely they will fail once you take them away from the stage where they are genius.

Recently a friend of mine who works in venture said of another investor “oh that VC is old school” and clarified it meant they like to bring in executive teams for their B rounds companies. Which honestly sounds like a dream to me. There has to be a middle ground between firing visionary but scattered founders once they’ve raised and trying to coach a mediocre manager into great growth CEO.

I think we should normalize founders being churned in on new ideas rapidly and churned out on scaling quickly. Let them get back to founding. Let them create more faster. Great scaling venture funds can provide more value by bringing in a scaling leadership team and easing the founder out to areas where they can focus on vision and direction. I say let the professionals run your team.

Obviously some founders dream of going from idea all the way to IPO but I don’t know if it’s the dominant path they desire. It could just be one of many. I have very little interest personally in shit like operations, process and scaling. I literally married a COO rather get good at it (insert joke about literally anything to avoid therapy). However it shakes out the “founder friendly” venture firm will remain. What it means to be founder friendly may need to be rethought.

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Chronicle Internet Culture Media Startups

Day 84 and The Thursday Styles Problem

The Thursdays Styles problem is about zeitgeist, wealth, perception and power. The New York Times publishes its “styles” section on Thursdays and Sundays. Generally speaking if you work in media, public relations or culture, you are aware of the general trends that will emerge on Thursday ahead of time. For the sake of argument let’s say I know directionally on Tuesday in private what will be featured on Thursday in public.

If you know “what everyone knows everyone else knows” ahead of time, there is a lot of money to be made as Tuesday person. For more on the second derivative issues in zeitgeist I highly recommend Epsilon Theory. If you can sense the zeitgeist ahead of time & move to take advantage of it you can be a Tuesday person.

Alas it’s not as lucrative as you may imagine to be a Tuesday person. A Thursday person who lives exactly on the zeitgeist can take advantage of “in the moment” culture moves. Good entrepreneurs do this well. Most consumer companies hit “right on time.”

This is why venture capitalists will ask “why now” as they may have invested in a Tuesday Person who hit the zeitgeist too early and couldn’t capitalize on it. It really pisses off the founder who knows “but I was first.”

As a Tuesday person, I hate when this happens. I loathe seeing people I perceive as less capable or intelligent than me hit a zeitgeist moment exactly on Thursday. The trouble is they are right. They won. They got the timing right. I didn’t.

And yes being a Thursday mover is good. But it’s crucial to understand who can win this game. The only way to win the Thursday Styles problem is to be in finance, media or culture work that can place a call option on the Thursday future on Tuesday. You have to be able to hold an opinion on the future zeitgeist long enough for Thursday to get published.

If you cannot hold your zeitgeist long enough for Tuesday to become Thursday when “everyone knows everyone knows” being right early serves no benefit. You need diamond hands. And yes, you will be wrong 9 times out of 10.

So you need to ask yourself if the New York Times cuts a piece and it takes another week to run can you hold out? If the markets don’t make a Tuesday idea hit, can you wait till it becomes common knowledge on that metaphorical Thursday? It’s a question for all long holds to ask themselves.

It requires patience to be a Tuesday person. And it takes resources. Knowing you will look wrong for a bit. Knowing that you will lose money when Tuesday knowledge takes longer to become Thursday Style’s common knowledge. If you can hold it’s the ultimate form of future leverage. That’s alpha.

And better yet, it’s “possible” to influence. Publicists make their clients on Tuesday shine on Thursday. And capture the upside. Folks who are extremely online spot how market makers make zeitgeist hit. Cathie Wood at ARK Innovations has been playing the media in exactly this way. The largest experiment in making Tuesday thinkers hit before Thursday is Margit Wennmachers at a16z.

Centralizing zeitgeist and monetizing it with future calls with narratives they tell on platforms they own stakes in has massive potential. The smart money is turning their Tuesday zeitgeist into Thursday Styles and taking it to the bank.