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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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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.

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Internet Culture Startups

Day 404 and My Process

Being sick gave me an investing process. I have ankylosing spondylitis which is an inflammatory condition of the spine. It’s well controlled but still affects my day to day routines. It means I spend a lot of time in bed on my phone online. And this is how I generate alpha.

I spend my entire day on Twitter, in Discord, in DAO governance chats, in news RSS feeds and on Reddit. I’m extremely online. Terminally so. Like a LOT. I’m talking twelve hours a day. Which has turned out to be great for deal flow and diligence.

Being extremely online gives you some significant tactical advantages as an investor.

  • Persistent read of zeitgeist
  • Always online intaking discourse that will move market sentiments
  • Omnipresent availability to founders and ready to interact

Being online and intaking discourse gives me additional time and analysis with emerging trends, personalities and opportunities. By the time something has gained traction I’ve already made a move. I can move fast and confidently ahead of others because I’ve just had more time with the materials.

In somewhat bleaker terms I already live in the metaverse. Having a disability gave me early access to new ways of living online by forcing me to live a lot of my life virtually. If I wanted to socialize I had to do it in bed. I had experience with this before the pandemic. And I’m already been living where the rest of the world will be migrating now. You are gentrifying my neighborhood.

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Startups

Day 398 and Experienced

I spent a part of my day gossiping with a friend of mine who is from the same cofounder cohort as I am. We’ve got a lot of common interests beyond having both been founders at the same time and I won’t list them as I don’t want to give them any hassle. But the two of us have seen a lot of the same things. We are now experienced.

It’s funny what you notice when you are experienced. We were noticing little aspects of how founders we taught or mentored or invested in tended to repeat. How there are certain repetitive patterns you notice in first time founders or folks who are new to Silicon Valley culture. You notice idiosyncratic elements that all n00bs have.

Of course the where it becomes hard is how much time do you put into coaching them. Can you help them level up fast enough to avoid all the mistakes you made? Can they outrun all their faults and weaknesses by adding new strengths where it matters? It’s honest the best work in the world. You find yourself constantly optimistic that big things are possible. That the best version of someone is inevitable with work and love.

Of course founders with battle scars know it best. We know where the sharp turns on the road are. Because we wiped out there. When we yell out to you to watch out it’s because we know the road better than you.

I’d also bet that this is why venture capitalists will stay with founders who are floundering and fucking up and being failures. You’ve seen their bright spark. You know their brightest self and it’s aspirations. And sometimes it’s really hard to accept when someone just isn’t going to make it. Because belief is deeper than facts sometimes.

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Finance Internet Culture

Day 394 and Antiwork

There is a Reddit sub that is imploding at the moment called Antiwork. I didn’t really follow it before the extremely online moment where one of their mods demonstrated that internet people don’t generally have media training. But one of the amusing bits of antiwork culture got into my feed because someone had an awkwardly worded tweet about young people demanding at least two days off of work in a week.

Before I became a member of the capital class I wasn’t really much of a weekend person. Or even a time off person. I was in a constant battle to get over the line of survivable earnings in America.

But then the magic of Silicon Valley shined on me a few times and I’m suddenly no longer desperate about medical bills or having enough savings for an emergency. This has had the dramatic effect of completely reordering my priorities. Now I take restorative rest time seriously. Knowledge work and good judgement rely pretty heavily on be clear headed. There is no premium afforded for being exhausted. If anything it will lose you money.

So the antiwork folks might have a point. If so much of your life is spent in survival you never have a chance to really be human. And being human is oddly more lucrative. I stand a better chance of doing even better because I can orient my life around bigger outcomes. That attracts more people and more money and improved my chances. And yeah success compounds if you are lucky. If you can get out from under survival. Which is I suppose the hard part.

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Aesthetics Finance Startups

Day 390 and Pitches

So I think pitching is bullshit. My husband has a great analogy. He thinks an hour long pitch to an investor is like a white board coding interview. Have any of you ever done developer work that didn’t have access to StackOverflow and Google? Yeah didn’t think so. It’s a completely artificial environment. Real work is collaborative and input driven and not at all tied to your capacity to memorize and perform on the spot.

I think this is pretty revealing. We force intuitive input driven thinkers, our founders, into a situation where they have little to no feedback. They can’t get anything from us as investors for like twenty minutes. They lead an investor by the nose through a narrative but what if it’s a narrative the VC doesn’t care about. Then what you lose the deal? Fuck no.

You should anchor a conversation based on expressing interest and seeing together where the biggest vision might lay. I’ve legitimately talked to founders who can see their way into imploding corporate legal apparatus or building clean energy through on chain gaming. That is some science fiction level shit. But could they tell me that in a 12 page deck? Fuck no they would look insane. But I want to see you for who you are.

So if you want to pitch me just hop on over to a Telegram chat or my Twitter DMs. Let’s talk and learn and share and then I can really see your passion and vision and we can both avoid canned performative shit.

You want an investor that sees you for you. I want a founder that is building with such a keen passion it’s all I can do to stop from wiring the money that day. Our incentives can align from first contact. So pitch me however you like to communicate. Plus, don’t we all die inside a little every time someone sends a Calendly link?

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Startups

Day 378 and Greenhorn

I’ve been running around the mountain west as I’m looking to buy a homestead. I’ve got kind of an elaborate master plan involving mountain houses & ranches and finding a set of living circumstances that works with climate change and social uncertainty. It’s a lot.

This means I’m doing a lot of social signaling to show people that I’ll be a good neighbor. Every place has its own social mores and expectations. I’m trying to show folks that I’m a good daughter of the inter-mountain west. But I’m also someone with the means to acquire property and invest in their community. But I’m also someone who appreciates the ins and outs of rural living. And well the list goes on depending on who I need to impress and about what. Every niche has its hierarchy.

It reminds me a lot about the process a first time founder goes through when fundraising. You are frantically signaling to different constituencies that you will fit into their expectations and worldview. But you do this dance while being completely new and naive to what matters. Being a greenhorn is bad for business. Doesn’t matter of that business is ranching or raising a seed round of venture capital. Alas everyone starts somewhere. So first time founders are often distinguished by how fast they can figure out all the shit they don’t know and fix it.

I’ve got a first time founder I’m excited to be investing in that I’m coaching through a fundraise. He knows his field and business, but he is a total greenhorn when it comes to raising a round. Just charmingly naive to the ways a round comes together. Alex and I are both frantically trying to school him on manners and customs before you can accidentally fuck up something that can’t be unfucked. It’s hard work getting someone schooled up on all the little signals that can doom a deal. But it’s also our specialty.

The particularly challenging aspect of a first round founder is just how much social signaling can be life or death for your company. Maybe if I’m up in Montana scouting property I need to show a certain set of mannerisms but the worst that can happen is someone won’t do business with me. If you fuck up a crucial deal point for ignorance or send a social signal you don’t mean, in venture it can sink your deal and your reputation without you even knowing it.

In venture, someone not doing business with you probably means your company dies. Early stage angel and pre-seed venture investors teach their asses off with new founders to avoid this fate. We can’t afford you being a greenhorn because we know it means death for the business. So if it’s your first time as a founder and fundraising, do yourself a favor. Recognize you are a greenhorn. Find an angel investor or advisor who you can trust that will teach you the manners and social signals you need. Good ones love this work. And you can reward them with advisor shares and pro-rata on your cap table down the line. If you are looking for someone like that drop me a DM.

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Background

Day 363 and Best Of 21

One of the unexpected benefits of writing every single day has been the accumulation of reference material. I can send folks a synopsis rather than retyping a topic that I get asked about a lot. So if you want to know how I get healthy, or how I invest, or even how I think about aesthetics this page will serve as a reference for year 1.

Health & Wellness

Biohacking 101 Guide

Supplements for Beginners

Self Care & Pacing and Recovery Protocols

How To Communicate with Me

Why I Prefer Asynchronous Communication

Why I Dislike Phone Calls (Or DM Me First)

Getting To Know Me for Founders Seeking Investment

Investment Thesis Thoughts

Empathy Investing

Chaotic Labor Markets

Chaotic Families

Request for Founders

Psychological Safety

Mental Flexibility

Bias Towards Fuckaround

What Don’t I Know?

Why I Don’t Like to Invest In Retail Anymore

Aesthetics

Fashion Week Back in The Aughts

The Thursday Styles Problem

Swag (Or My Facebook Hoodie)

A General Theory of Shitposting

Cultural Hegemony and Internet Citizenship

A Short Guide to Becoming an Edgelord

Advice for Startups

Above All Else Fun

Inertia

Rooting For You

Stress, Luck & Startup Families

The Emotion of A Big Exit (or Stack Overflow Sold)

Show Me Anything

Just Make Stuff

Optimizing For The Right Outcome

How To Work With A Startup

Emotional Growth

3 People Inside You

Punishment

Forgiveness and Failure

Easy for You (Not For Everyone)

Superpowers

My Addiction to Work

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Startups

Day 360 and Have Fun

I’ve got a friend who is a world class talent in their field. I admire what they do. But their ability is fairly is specific to what they do at a startup and doesn’t transfer easily to different stages. They recently took a job at a different stage and I’m a little afraid for them. What if it breaks them? What if they get burnout? I am projecting a lot onto this friend at the moment as I am also a fairly specific kind of talent. I’m an early stage person.

The reason I’m so sensitive is I’ve been broken by being in the wrong roles or working on the wrong problems. I tried to change myself to fit something I was only a 7 at when I knew I could be working on something where I was a 10. I hurt myself to fit in.

The hardest part about startups is they are genuinely life altering. It’s hard to make something new. Every harder to nurture and grow and sustain it. Creativity is fucking hard. Every time I criticize a project I do it with a hitch in my heart. I know even the shitty failures were the honest best work of people who cared. And often when it’s a success it’s not because any of them were better than anyone else. We are all fighting our hardest battles. Sometimes by the grace of God our work gets lucky.

So in the meantime I think we should all be having fucking fun. I only commit to founders who so clearly want to solve the problems in front of them. That passion cannot be forged. Real interest and focus are such potent forces. You feel it in your bones. Doesn’t have to be a huge world changing problem either. You can just really love your little corner of the universe.

So don’t try to fit yourself into a role for money or status. Pick a startup because it’s going to be a blast with people you love. Make sure as much of the work will be your particular brand of fun. Maybe to someone else it would be hard work. But if you pick right it will be fun even if it takes all of you to do it to the standard of your passion. And if you are very lucky sometimes it works.

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Finance Internet Culture

Day 359 and SOS

A few days ago I wondered what project or cultural artifact was going to grab our mutual cultural attention during the Christmas vacation week? Something always does. One year it was fucking Quora if you can believe it. This year I’m ready to call it for $SOS at least if you are into Web3 and crypto economics.

On fucking Christmas Day these degenerates drop a contract to let anyone claim tokens who has ever purchased an NFT on the OpenSea marketplace. And people went ape shit. Suddenly someone had taken all the visible contributions from OpenSea and manifested them in a token and said this is ours. Fuck corporate dominance of profit your users hold the real value. I’ve never seen anything so ballsy. Last year when Wall Street Bets decided to taken on hedge funds I felt like we had entered a new era of community behavior.

An emergent community has swum up from the sea and eaten the lunch of a supposedly greedy centralized platform. Web3 just attacked what we didn’t even realize was Web2. A crypto darling turned parable for centralization in the space of a few years. $SOS seemed to say community owned this value all along. The airdrop showed us the balance of power in a web3 community if we all work together. I’m so impressed by the sheer cultural force of the statement. It could all go horribly awry but god damn if it isn’t utopian.

I’ve got not fucking clue if this is a legitimate contract or not. I’m not going to FUD. But from a first principles, we are building a new internet where the incentives of the users align with the technology statement, then this is quite a shot across the bow. Also I’m pretty sure this makes it harder for OpenSea to IPO if their user base is in open rebellion against who gets rewarded.

The thing is I believe Devin to be a well meaning and genuinely forward thinking guy. He’s a terrific communicator that set out with the utopian intentions that we all do. But we are moving so fast with breaking cultural norms and acceptable societal level rewards for contributions to an economy that I think we might have just spiraled up to some kind of cultural singularity. Crypto might just be moving that fast. Whatever happens this is one of the coolest things I’ve ever seen from a startup. Score one for the anonymous degens.