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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.

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Startups

Day 468 and Small Moves

One of my favorite movies as a kid was Carl Sagan’s Contact. It’s not a great movie but it’s heart is in the right place. It’s a beautiful story about human curiosity and the long timeline of history. In one of the closing sequences the protagonist is told by alien intelligence as embodied by a representation of her dead father that all next steps are “small moves Ellie.”

I never feel like I’m moving fast enough. Every day presses against me. I long to slog through them with speed and alacrity. It’s almost embarrassing how inadequate I find my progress. But then I remember that I move fast. I live ahead of the mainstream. I get to sit in the future that William Gibson said was not evenly distributed. Even if I don’t think I’m particularly good it’s hard to deny just how much of my life is lived in a tiny sliver of humanity.

Someone recently asked me how I moved so fast when I’m dealing with a chronic illness. I found it to be such a shocking question. I feel like I’m glacial compared to the reach of my desires and imagination. But then I’m reminded that even in shorter hours I’m forced to hone my crafts. I can’t afford to waste energy or focus so I simply do not. I imagine this focusing out of need is similar to what parents of young children operate in. The subtle art of not giving a fuck.

And so what if I am slow on a day to day basis. Rome wasn’t built in a day. I’m not a market trader. I invest in ten year cycles. Everything in venture is actually small moves. But as time adds up so do the aggregate of the moves. Compounding interest is up there with gravity as a force. So even when I yearn for more and for it to arrive faster I have to trust the numbers.

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Emotional Work Startups

Day 466 and A Painting Without Shadows

I take therapy really seriously. I’d put being emotionally capable of managing myself at the very top of my life priorities. Honestly it should be number one and if it isn’t I need to stop and ask myself why. Being an adult requires an intimate understand of one’s emotions and the capacity to share them with others.

To further this goal I do a weekly session as well as group work. It’s meaningful to me and I recommend to all my founders that they find a way to get into coaching as well as therapy. Taking care of your own inner child is the only way you are going to be able to lead a team. If you want to build a billion dollar company and manage thousands of people you better be able to manage yourself first.

Where I think people can go wrong is treating this process as if it’s one of optimization. Do I think founders who have taken the time to understand themselves do better? Absolutely. It’s pretty rare that someone’s coping mechanisms help them reach the heights of their talents. A chip on your shoulder is great but eventually you learn to transcend it.

I think this is because if you don’t understand yourself you are a painting without shadows. It’s flat. Boring. Doesn’t read as true or trustworthy. Maybe you are really good at showing emotions to get your way. Lots of people are but if they just off enough from genuine then it reads as the uncanny valley of empathy. People just know when you are hiding something. And hiding your dark side means hiding your shadows. Without them you are a flat human.

A painting without shadows wouldn’t be any good. You without your shadows wouldn’t be who you are. The best of you exists because of the worst of you. I really do hope more people are able to see that truth and love themselves.

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Internet Culture Startups

Day 461 and Remora

I saw a headline about how Trump’s social media site is failing. I’ve got no idea if that’s true but the media likes the story. This is playing out in the context of Elon Musk using corporate governance as a public relations stunt with his new Twitter board seat. Everyone wants to be an attention grabbing technology company even former presidents and aerospace billionaires. Because even the stupid stunt stuff in tech can be world changing.

I’m at the big Bitcoin conference in Miami. It’s a lot but it’s not fundamentally any gaudier than any other industry event I’ve attended in twenty years being adjacent to startups. Before my current stint as an investor I worked in fashion and beauty so I’ve seen a lot of excess. M I was raised in a boom time Web1 startup family. But also my family went bankrupt. I’ve seen the dark sides. I still work in tech. Like Trump and Elon I too just want a piece of the action.

It’s because startups change the world. Even stupid weird dopey absolutely cult adjacent shit can and does change the world. All these prestige television takes on frauds and crashes and the cult of personality nonsense miss that sometimes those freaks actually do it. Sometimes they change the world. Ok most of the time they don’t. See the current unraveling of Fast. 99% of the time shit goes bad. But to have even a little bit of the action of the 1%. It’s fucking dazzling. It’s worth being adjacent to all the bullshit.

I hold in high esteem the folks who work at the flameouts. Anyone who takes a chance and has it go bad has my admiration. I’ve been one of them. I’ve failed a lot. I’m lucky I don’t get punished for it. At least not much. I’ll never know how much shit like my gender or my ridiculous social media personality factor into that shit. Because I am always allowed to get right back into the action and make shit. Making shit is our currency.

I think this is why even the most powerful people gravitate towards startups. You actually get to make shit. At the earliest stages you get to be personally responsible for so much. Your actions have meaning. You contribute. You know how rare that feeling of community and camaraderie is in peacetime?

It’s a commodity so precious we let ourselves be led by girl bosses and fast talking celebrity thought leader venture capitalists. We tolerate a lot of assholes and psychopaths so we can be in a community of people that make things. It’s the American dream and the most basic human need all rolled up into one.

That ought to give you a sense of the cultural power and vitality of startups. That’s loyalty on par with religion. That’s move history big dick energy. And I think some people hate it I find the hate inscrutable but I’m sure it’s probably legible to those who feel left outside.

So yes boom time early energy big money hanger on remoras are part of any thriving ecosystem. And as far as I can tell Bitcoin has the manna to go the distance. Because everyone wants a piece of the action.

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Startups

Day 452 and A Short Guide on Cold Outreach for N00bs

I have an open Twitter DM policy for founders. I encourage outreach to me via all forms of asynchronous communication. I think the hour long pitch, either zoom or IRL, is a bad way to get to know someone. But that doesn’t mean there aren’t rules and social graces involved in cold outreach. I’ve outlined an FAQ on how to get to know me and what I look for in founders but it seems like people would benefit from more tips on how to ask for help and investment on social media.

1. Give Me A Synopsis

If you are sliding into my DMs remember that I’m probably just glancing at an alert. You want to get across just enough context to encourage me to pop in and take a look. And remember you don’t need to convince me with one paragraph. I want to develop a relationship with you and learn how you think. That’s not possible in a few sentences so remember that synopsis is just the beginning.

2 Use A Social Account With Shared Context

I’m always surprised by people who slide into my DMs with 15 followers and a blank Twitter profile and expect an answer. Use the shared social graph to show your interests and tastes. Follow and be followed by people in common with me. You’d be surprised how much meaning I take from seeing you follow and interact with people I respect. The social graph is now we vouch to each other we’d enjoy spending the next ten years working together.

3. Tell Me Who You Are

Make sure you’ve got a link to a personal website so I can learn more about you. It doesn’t have to be elaborate. I think LinkedIn is lame but it’s easy and shows your skills and career path. Hate that? Link your TikTok or Tumblr or blog. Are you anonymous? That’s totally fine. I’ve funded anons. Give me the portions of your identity that are on chain or under your pseudonym so I can learn more from there.

4. Rome Wasn’t Built In A Day

You don’t need to ask me for an hour long pitch or even my email right away. I don’t need perfection from the start. Just say you are working on something and want to talk to me about it. Say you will send me a white paper or a blog post and ask me to read it. Then follow up in a few days to see. Don’t get social anxiety about it either. I probably just forgot or got busy and I love being reminded. Truly.

5. Only Ask for Favors After You’ve Demonstrated Rapport & Competence

I cannot tell you how many times I’ve been asked to for advice, help or investment in DTC, CPG or retail type businesses which I have explicitly said I do not do. But what’s even wilder is that the question right after I say no is almost always “well can you introduce me to other investors that do?” This isn’t an inherently bad thing to ask me. I want to help. If you’ve shown me a great product and I’m engaged and impressed with you as a founder and we’ve had a few interactions ONLY THEN do we have enough of a relationship where it’s ok to ask me to spend my social capital to help you. I can’t help you till I’m sure you can help yourself and that means demonstrating you won’t waste the time of my network as well. Favors are big asks and I only want to use them on people who will reflect well on themselves and on me to my network.

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Finance Startups

Day 432 and Send Me Dealflow

The markets are struggling with the chaos of the Russian invasion of Ukraine. Nickel prices doubled. Gas is skyrocketing. Central banks are due for rate decisions but it’s anyone’s guess as to whether hikes will manifest. But in my neck of the woods uncertainty is our business. Chaotic.capital was founded on the belief that an increasingly complex world would present opportunities. And I’ve never felt more confident in our thesis.

With chaotic.capital we’re identifying, investing in, and supporting companies that adapt our lives and systems to the opportunities that chaos brings. We like companies that are adaptable. We like companies that help others become more adaptable. If you are still building in the chaos and want an early stage pre-seed or seed stage investor I’d like you to drop me a line this week.

I believe it’s possible to find leverage in chaos. As scary as this moment feels, it’s possible to profit off of the many ways the world may change. Geopolitical instability isn’t going away. That’s got downstream effects. Think supply chains remaining strained and snarled. Commodity prices continuing to be wonky. People on the move from immigrants to refuges. All of these problems will be opportunities for businesses to improve lives and make money. Everything from logistics software to temporary housing falls under the chaotic remind.

We are not scared of weird bets. We like unsolved problems. If it’s easy to model your growth and the exact trajectory to success, we may not be your partner (though we’ve got friends who will love you). But if you have a point of view on how chaos will enable your success, we don’t need a perfect plan, just a possible future.

Just to give you you an idea of how serious I am about finding weird shit let me tell you the deals I’m excited about this week. I’ve seen an occult marketplace, a real time DeFi data platform, a marketplace for vegetable gardens, logistics and 3PL software for influencer boutiques, and AI assisted direct to consumer abortions. No problem is too weird for us. So come on and slide into my DMs.

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Internet Culture Medical Startups

Day 415 and Accessibility

I don’t think of myself as disabled or requiring special accommodations, though I have a well controlled medical condition that swells my spinal cord called ankylosing spondylitis. But for the first time since my diagnosis I really felt like I was handicapped. And I am feeling so much sadness over the idea that I might genuinely be disabled.

I’m attending ETHDenver and it’s wildly over capacity. No consideration has been given to any kind of basic accessibility. I didn’t think it would effect me though till I got here. I can walk without a mobility aid and if you met me you’d never know I have an issue. But I can’t stand in line on cold concrete for two hours. It turns out I would need a wheelchair for that kind of activity. And even if I had a wheelchair the first two days were in the cold and snow so I couldn’t have wheeled over or around the slush and water.

So I have only attended private parties and small events and group outings. This is great for me as I’m a well networked established member of the startup ecosystem. I’ve got a popular Twitter handle and can easily reach out to people. But I’m noticing just how much a bit of inaccessibility will gatekeep the crypto and web3 community. If you don’t have my heaps of privilege there is no way you could navigate this conference.

And we really need web3 to be welcoming and accessible. To build a better future with infrastructure and economies we all collectively own and benefit from we need an order of magnitude more people participating. But if no one can get in and experience things first hand than web3 will just be a repeat of the oligarchy of web2. It’s honestly my worst fear for crypto. We will accidentally exclude the people who will benefit the most from our innovations.

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Finance Internet Culture Startups

Day 414 and Empire’s End

Being at a crypto convention in 2022 is something else. It’s full jubilee at the end of the world shit. You are surrounded by millennials and gen-zers who know in their gut that their future has been stolen from them. And instead of being pissed they decided to build. And they decided to gamble. And it’s not clear which one is which sometimes.

You’d be forgiven being a nihilist right now. Capitalism looks like an excuse for the oligarchs to consolidate state and private power to enrich themselves. Everyone is soaking in student debt and working shitty interchangeable jobs for corporations owned by private equity. No one can afford a house. No one is stable enough for a marriage and children. Our fucking parents won’t retire and won’t listen to reason when we say their neighborhood needs more housing density.

But if you are in crypto the future looks pretty rosy. You are discussing real estate for your second home and the tax advantages of different jurisdictions. Swapping stories about your friend who accidentally didn’t set up estate planning and his company had a big exit and now he’s got to pay full rate to some expensive Democratic run city and state. If you are at the nice cocktail parties you are building the future and the venture capital is flowing and it’s possible that this is the next big wave of innovation. It’s time to fuck around and find out.

But not everyone in crypto is part of the smart money. Not everyone has institutional backing and the professionalization of long time startup operators coming to build real value. Right right below that success is a teeming horde of brutalized and completely marginalized people who are praying they hit it big on some new coin or hot new NFT project. They saw Bitcoin and then Ethereum go to the moon. So now they are praying to the full moon and hoping they ape into the next big thing.

But what’s scarier is that the prevailing attitude is who cares if it’s risky because no one believes they are going to have a future anyway so you might as well gamble. They might get lucky and build the next Google if they join the right DAO and buidl. Yes I typed buidl. I’m a degen too. I’m a doomer that isn’t convinced the empire is going to hold for much longer. And if I’m going to watch it all crash down I want to be a part of building something better for all of us. Maybe we get lucky and innovative faster than the apocalypse. To be fair, humanity always has in the past.

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Internet Culture Startups

Day 413 and Don’t Believe the Hypebeast

My early twenties were heavily influenced by streetwear and sneakerhead culture. I lived in the Lower East side and hung out with all the kids who would go on to dominate what is now a multi-billion dollar industry.

It feels weird listing out my bonafides as it’s pretty name drop-y but at the time it was like yeah my friends at Alife or High Snobiety or even god forbid Supreme meant basically nothing. I was in the absolute epicenter of hypebeast mania.

So I’ve got a gut sense of what a genuine upswell of obsession looks like. The kind of irrational social capital driven cool mania of the sneakerhead world has a specific vibe to it. Almost illegible to anyone outside. But to the in group? It’s powerful chaos magic binding geas shit.

That’s what EthDenver felt like today. A kind of disorganized overflow of true believers converging into a space about a quarter of the size required. It’s like if TechCrunch disrupt accidentally got overrun by the entire readership of HypeBeast. Honestly it kinda sucks.

You’ve got a number of accomplished teams and founders and investors all trying to figure out how to navigate long lines and complete chaos with no clear programming goal or event schedule. And then you’ve got thousands and thousands of NFT weirdos just shilling and excited and ebullient about stuff they freely admit they don’t technically understand. It’s going to be a wild ride for crypto.

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Startups

Day 412 and Status Anxiety

I’m attending Ethereum Denver through the weekend. If you aren’t familiar it’s a fairly substantial crypto conference with wide appeal and good credibility across the entire ecosystem. I don’t have any special hookups nor do I have a careful plan of attack. It’s my first time attending a large industry event as an investor.

Truthfully I’m incredibly nervous. I’ve never been on this side of the table before. I’ve always attended events as a founder. Which is an entirely different mix of status and social positioning from a venture capitalist. Founders are the cool ones. The top of the social hierarchy. It’s the hardest job in the business and in exchange we revere them as a kind of messianic class. We all place our belief in the people who start building from nothing. Even if you haven’t yet had a big success it’s the act of beginning that has the potency. Anyone who has the guts and steel to try to make something new is part of that rarified class.

So while I ostensibly have more power than I’ve ever had in my entire career, I also feel a slight sense of social anxiety. This is the first time I’ve not been in the anointed. So in a very real sense I’m walking in without any of the power that I’ve had before. And I’m a little scared.

Will people think I’m cool? Will I get invited to go to the right parties? Will the right people want to talk to me? Will I look good enough? Will I be able to hold my own such that I can capture the attention of other peers?

I’m used to needing to network hard to find the money. I’d roll into events with my team squashed into one room and we’d plan out every single minute to maximize our budget. Now I’m the one teams will be searching for pitch.

It’s this strange blend of gaining new status but missing the old place and position in a culture that has me a little nervous. So if you find me at the conference know that if you are scared to strike up a conversation you are not alone. We are all looking to find each other and connect.