Tag: Silicon Valley

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Internet Culture

Day 671 and Greatest Show on Earth

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

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

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

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

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

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

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

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

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Finance Internet Culture

Day 654 and Inappropriate Language

As much as I love to joke about getting cancelled on Twitter, I’ve never actually worried about getting dinged. I resisted getting a Blue Check and otherwise pursuing the trappings of being a power user as I was confident that my real world connections would overcome any algorithmic nonsense.

Digital power still resides on a firmament of real world power. I figured I know the right people in real life at Twitter, so short of me encouraging a coup while also being the President of the United States of America, I was pretty safe in maintaining control of my account. This was perhaps a bit naive and I knew it.

The algorithms do in fact come for us all. I got an unprompted warning today that a user on my account (I’m the only user but whatever) had been deemed to be using inappropriate language.

A Twitter warning saying my account AlmostMedia has inappropriate language so is ineligible to run advertisements

At some point I had the power to run promoted posts, otherwise known as advertisements, but because I have angered the language police at Twitter I am now no longer allowed to pay to promote my own speech. I guess I overrode the “are you sure you want to tweet this most users don’t use this speech” warning one too many times.

I swear more than average for a woman but probably a lot less than average for someone in finance. My account is notably a shitposter account. I remain fascinated by social status and access of all kinds, and shitposting remains of the higher status activities in social media culture as it demonstrates you need not be censored by social mores or common decency. Except apparently I can be.

You can get worked up about whether this infringes on my speech as I can say anything I like but now I’m no longer able to pursue any paid reach. This is the popular theory that everyone is entitled to free speech but not free reach. Or I guess in my case paid reach.

To be honest I had no intention of buying any paid reach advertising on Twitter. The folks I care about generally seem to get my Tweets and I’ve got no sense I’ve been shadow banned. Well, ok now I am worried but I wasn’t before this goofy warning.

To me this feels like a reminder that Twitter just doesn’t give a fuck about its power users. I am a well networked and well liked (or well hated) account with powerful followers in the core demographics that matter on Twitter.

I sit inside a nexus of media, finance and Silicon Valley personalities that care a lot about the platform even as the platform mostly doesn’t give a shit about us. Which is arguably why we’ve all spent six months giving a shit about Elon Musk buying Twitter. When a power user gets banned from advertising producers it’s not really a problem for the user, it’s a problem for the ad products team who is fucking up making money. You know, their job.

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Finance Internet Culture

Day 651 and Best Guess

I’ve loved the discourse of indignation that has surrounded rich men doing deals via text messages. There was lot of hand waving about the death of genius and the meaning of it all. Isn’t it such a scandal our best and brightest are just saying shit on Twitter DM?

I suppose if you never worked in startups or finance it might come as a genuine shock that rich techie people are no better or smarter than anyone else. Why the fuck do these dorks control all the money and resources then? I’d say it is because they are willing to make their best guesses.

One of my favorite scenes in Star Trek is Spock struggling through a series of calculations and informing Captain Kirk that he may need to make a guess. Kirk’s response? That’s extraordinary! Spock is naturally confused. Dr McCoy or Bones has to do some translating.


Bones: He means that he feels safer about your guesses than most other people’s facts.
Spock: Then you’re saying… it is a compliment?
Bones: It is.
Spock: Ah. Then I will try to make the best guess I can.

Star Trek IV The Voyage Home (The Whale Movie)

Everyone is just muddling through and making their best guesses. Even the best and brightest among us are struggling to make it all work. I’m not suggesting the folks making the Twitter deal are as good as Spock but they are just making their best guesses too.

And for whatever reason they are willing to put a lot of money, time and reputation on the line to see where their best guess might go. That’s pretty courageous in its own right.

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Finance Startups

Day 649 and Build in Public

People love building in public. The universe loves a specific ask. Today for my 39th birthday, I am doing both.

I would like to raise $5m for chaotic.capital’s rolling fund before I turn 40 next year. #5Before40 has a nice ring as a hashtag right?

Chaotic is the first check into founders and companies that adapt humanity to complexity. Personal flexibility, organizational agility, and societal sustainability.

Our founders capitalize on chaos.

You may have noticed I’m a bit of a doomer. I keep close tabs on the opportunities presented by an increasingly unstable world.

Climate change, distrust of institutions, geopolitical unrest, resource scarcity, rising tides of populism. There are founders who can help us address and survive these pressing issues.

My goal is to raise $500K per quarter via a rolling fund. There is 155K per quarter committed from folk like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company.

With a base like that, I want to do the rest in public here on the blog and Twitter. You can read the fund overview here. Building in public has generally been my preference and it has felt weird doing any of this fund work quietly behind the scenes.

You can sign up on Angellist through the above link or get on a call with me and we can discuss the fund, our portfolio construction and my thesis.

I’ve got big ambitions for accelerating into maturity as I have no intention of letting entropy win.

Humanity deserves progress, and I demand growth for myself. I’d like to make us both money with that. 

______________________

FAQ TIMES

Haven’t you been investing through chaotic before? 

Yes but just with personal capital and an SPV. I want to scale it up as we believe our performance warrants it.

Go check out some of our best investments here. https://chaotic.capital/fund-overview

______________________

Why didn’t you raise more during good times? Why the fuck are you raising a rolling fund at the end of the world?

Did you miss the part where I am a Doomer? We are a bad times fund. This moment is where our thesis matters.

Good times return and you’ll appreciate having written a hedge check or two into weird companies that are designed for the power laws of institutional chaos.

Or if the fear of the moment feels overwhelming you can sit back and die the slow death of uncertainty. Trust me I’ve considered it as well.

But personally, I’d write me $10,000 check and come along for the climb back. Entropy only wins if we don’t fight back.

Categories
Startups

Day 501 and Do It Live

There must be some kind of residual high from making big decisions, as I’m feel powerful as hell coming out of Montana. I’ve committed to a life path and I am ready to do some thriving. Yes I’m referencing the meme.

unbothered. moisturized. happy. in my lane. focused. flourishing

I’ve got a deal I want to shop around even though it’s ice cold out there in venture land. I believe in the team and I believe in the market sector. It’s a bit of an unusual bet but I have total confidence in the problem space such that I am ready to spend some social capital. So hit me up if you want to get in on the deal. I feel like it’s a deal that’s absolutely in my lane and even if it’s a hard time to circle anyone to anything I may as well enjoy the thrive vibe. Let’s do some magic together yeah?

In another famous meme Fox News host Bill O’Reilly exclaims that “fuck it I’ll do it live!” And I have to say that is my current energy. None of us have a fucking clue about how things are going to go. But did we do our homework? Yes. I did the work. I ran my numbers. I’m good at what I do. I’ve got experience. I’ve got as good a shot as anyone.

So I’m going to say fuck it to a lot more. I’m confident. Because like Bill I’ve got the talent and why not fuck around and find out? This isn’t specifically about the deal I want to do (though I am excited) or the fact that I’m moving to Montana but rather that it’s time to express more confidence in general. I shouldn’t undermine myself. I’m good. Some people like me. And that’s enough to have some confidence to try some stuff and experiment. If you want to come and play with me feel free to say hi.

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Politics Travel

Day 491 and Uncanny Valley

If you’ve been following along this week you might have noticed I’m in Bozeman Montana with some friends. I’m hoping to find a homestead. My father loves to call Montana the last best place. He moved up to Whitefish a few years ago for retirement from Boulder Colorado. Our boomers know the score. He knows the last best places are dwindling as the frontier turns into subdivisions.

Growing up in Colorado was about as close to paradise as it gets. We had clean air, plenty of open space and a laid back uncrowded atmosphere. My brother was born there but my parents made a brief detour to Silicon Valley where I was born in the eighties. But Chief Niwot’s curse must have called to my family as we moved back to Colorado when I was still young. My dad thought Boulder was a better place to live than San Francisco or Palo Alto. No one who has been to Boulder escapes the curse.

“People seeing the beauty of this valley will want to stay, and their staying will be the undoing of the beauty.”

What is Chief Niwot’s curse?

I call myself a Boulder native even if it’s not technically true. If you count the sojourn in the Bay Area, I’m one of those Californians that ruined Colorado even if my family had arrived long before I did. But we certainly didn’t arrive before the Arapaho. Perhaps I wasn’t in the wave of Californians that turned Colorado, and Boulder Valley in particular, into a boom town in the aughts and teens, but I’m still part of the undoing of the beauty of this valley. Anyone who is descended from immigrants has contributed to the curse.

The reason I chuckle at my father calling Montana the last best place is because the state is following the path that Colorado took. Bozeman feels exactly like Boulder did during my childhood. It’s no surprise to me Colorado folks are moving here to recapture what we’ve lost. If you came of age in the mountain west before urban sprawl and yuppie gentrification you yearn for a return. Boulder Valley has been undone by those that loved it’s beauty. And so we seek new frontiers.

In twenty or thirty years will the Gallatin valley and Bozeman face a similar fate? Almost assuredly. If anything, it makes me confident in putting down roots here. Maybe then my kids can call themselves Bozeman natives the way I do with Boulder. Maybe they can complain about the high housing prices and the arrival of tech workers and tell tales about how their family got here in the roaring twenties before all the Coloradans ruined the place.

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Startups

Day 490 and Startup People

One of the more transformative experiences of my young life was attending a founders only conference in 2010. I’d never been around that many other people who did the same thing as me before. I felt so seen.

The most unexpected thing was how relaxing it was to be among other people who understand the context of my life and my work. All of the weird and idiosyncratic elements of being the CEO of an early stage company are hard to translate to someone who has never had to live it. Startups are lonely work and being the CEO is the loneliest job in the company.

Obviously the last twelve years of bull market have greatly expanded the pool of people who have worked in startups. It’s gone from a niche to the driving force of American industry. Everyone grew up. Some of us made money. We’ve professionalized. We’ve developed best practices. What was once a scrappy singular experience is now a repeatable innovation.

And like that conference it is transformative to be seen. don’t feel so alone anymore. There are more people who can share in the context and specifics. I’m in Montana this week with friends who have a similar life path to myself and my husband. Our friends completely understand the context of our lives and we understand their context. We are all founders and executive team members and angel investors and LPs. And yes it’s relaxing. I highly recommend it.

Categories
Internet Culture Media Politics

Day 482 and Vibe Shift

A month or so ago a piece written by a New York marketing executive titled Vibe Shift went viral among the chattering classes. The premise is that we are on the precipice of a cultural change that is upending everything from politics to fashion. And depending on your perspective, this shift might include crumbling dystopian decay or vibrant fuck it optimism. Or in the case of web3 absolutely both.

I think the Vanity Fair piece on the New Right is chronicling one of the first emergent vibe camps to emerge from the vibe shift. The article is a look at the art, intellectual environment and personalities of the “not quite conservative” new right. And it’s a largely positive even glowing send up.

If you believe the Citadel is a corrupt institution and moral moral crisis then the Vanity Fair piece should have been negative. It’s a surprise that it wasn’t. Not long ago we were subjected to intense narratives about the dangers of nRX neo-reactionaries and it’s infiltration of Silicon Valley. It was a real and urgent issue that the center of so much money and power might doesn’t align with the cultural values of media or academia. If you don’t speak this language the Citadel is code for the left leaning creative and cultural institutions like Hollywood, academia and media.

So why isn’t it a crisis any more that there is a new breed of influential “not quite” conservatives? If anything the right in America has shown itself to be capable of so much more than just boat parades and goofy hats. Some of these fuckers were expanding the Overton window on peaceful transitions of democratic power on January. It might actually be getting worse.

Except now the left fucking sucks too. Now I’m not justifying fascists. These Christian Nationalists are trying to roll back modernity and pluralism. Fuck them. They fuckers don’t even have a demographic majority. So it pains when I say the vibe shift is showing the left as the worst version of themselves while the right is showing a new cultural ascension.

To a lot of normal moderate people the left looks controlling, scolding, frigid, and conformist. Everything from mask politics to gender relations has started to make the left look insane. It’s entirely rational people would be seeking a vibe shift for something more welcoming.

My theory is we are about to see a massive resurgence of affection for all kinds of conservative hobby horses. Especially of vibes that used to be the province of the traditional left. Everyone is sick of being shamed while they go about living their lives. And whoever wins that vibe war will win America.

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Internet Culture Startups

Day 479 and High Agency

A corner of startup Twitter was discussing the relative ease of getting connected to power brokers in different industries today. The debate? Does good talent eventually finds its way to resources? The contention from Roon, otherwise known as Mr. Wordcel vs Shape Rotator, is that networking is less crucial in technology than in any other industry because it’s easier to find a way in.

While one can quibble with how true this is for all populations, it is truer than it’s ever been. A large swath of the startup ecosystem is readily available to anyone on social media. We are less constrained by geography and credentialism than we’ve ever been. This is partially because much of the wealth in the current generation came from building social networks or software that benefits from openness. An excellent overview of this is why good angel investing ecosystems prioritize welcoming newcomers by Alex Danco. Most investors want to be available.

But it’s still a challenge to find high agency and high talent people and there are far fewer of them than you’d imagine. And proving you are high agency and high talent isn’t always an intuitive process. Being able to assess if someone has the capacity to build is one of the hardest job a capital allocator will ever have. Judging markets and products and roadmaps is much easier than discerning if someone has the capacity to execute on their dream.

I personally use follow up as my first heuristic. This is partially because I maintain open DMs so literally anyone can and does reach out to me. If someone is able to regularly show up and engage with me and show progress they are better than 90% of people. Honestly go ahead and try! I really am here to help.

You’d be shocked at how often someone pitches me and then I never ever hear from them again. And it’s not because I missed the boat (this happened once to me this year). It’s generally because people are waiting for someone else to act. And this is where people fail. The first rule of startups is figuring out how to create momentum. If you are waiting for me to cut a check you’ve already lost.

I’d like to do a whole post on this topic but I’ve been struggling to get the bulk of it on paper as I’ve got a migraine coming on. But rather than put the post off, I organized an introduction of the subject and put down my first heuristic. Which is ironically exactly what I look for in founders and builders. Did you make some visible amount of progress no matter how bad? Did you put it out into the world? That’s better than most people!

Categories
Startups

Day 470 and Social Skills

Startups are just as much about social hacking as they are hacking something technical. We worship the archetypal “coding nerd” who is brilliant but awkward, but in reality building shit requires an awful lot of social finesse.

I meet with a pretty wide range of founders. A lot of them are clever but relatively normal people. But many founders are fucking beyond weird. I see a lot of neurodivergence. But it’s not all towards the awkwardly autistic. Plenty of founders, especially in web3, are almost supernaturally charismatic. No literally it’s magic.

And that magic is good for making something new. The ability to empathize and listen is hugely prized in leadership. Being present and able to socialize in any social context is key to bring diverse groups together. We are much more willing to throw in our resources behind a founder who can rally us together. And this is just objectively good for the startup. Of course investors want to back that kind of person.

I think some people are offended by this reality. We see endless pop culture depictions of narcissistic sociopaths raising shit tons of money and then destroying their companies. I’m honestly a little sick of it. It’s no secret that Silicon Valley, but capitalism on the whole, occasionally rewards charlatans. I don’t think it’s particularly indicative of anything but human nature. Like Fox Mulder I too want to believe.