Categories
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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Startups

Day 406 and Like I’m 5

I welcome pitches through my social media channels. I’ve even gone so far as to put together an FAQ for how to pitch me. I hope I do a good job of welcoming founders at even the earliest stages into conversation. But just because I am happy to shoot the shit with you, doesn’t mean I’m capable of organizing your thoughts for you.

Want me to write a check? When you are getting started with me keep it simple. Ground me in the basics so you can take me into the details. Go from whole to parts.

Now I’m not asking you to dumb it down. I’m asking you to do the work to really clarify what you want to make. Maybe it doesn’t sound as impressive in a few sentences, but trust me you must anchor everything in the basics. If you cannot articulate the core product you need to build how in a few sentences, how do you think you will convince me to support your biggest craziest vision?

Now what I am asking you to do is actually quite hard. If you aren’t sure what I mean when I ask for a basic product description spend some time on the excellent Reddit sub “Explain Like I’m 5.” The premise is simple. If you have a complex technical topic that requires expertise you need a way to get it across to a layperson.

You will hire a lot of lay people in your career as a founder. I am just the first one. Educating me on what you are doing is hopefully the start of thousands of explanations you will give on what your company does. Because we both want you to build a big company right?

So while you are welcome to send me your standard 15 page deck, or in depth Notion documentation, or your favorite Substack blog posts, you know I have to explain it to the co-investors, new hires and LPs in a sentence right?

What I don’t want is to dig through dozens of documents and feel even less sure by the end of my diligence of what you are building than when I started. I want to hear a synopsis that excites me to dig in and then go on a journey with you where I learn just how much you’ve thought about it. But if you can’t keep it simple you probably aren’t ready to be fundraising.

Categories
Internet Culture

Day 403 and Hurt

It’s ok if someone hates me. It’s ok if someone thinks I’m bitchy, stupid, obnoxious and self serving. Hell I’m ok if people think I’m a lesser human being. Which judging by Twitter could be a multitude of reasons ranging from “I’m a woman” to “I’ve got bad taste in tv.”

I am alright with you not being alright with me. My existence is not threatened by your philosophy or personal preferences. My existence is only threatened if you literally threaten me. Call me evil if you like. I’m not offended. Until you take an action against me it’s alright that we disagree. Even if the disagreements are existential.

It’s quite possible this is wrong. I’m open to debate on what constitutes harm. In fact, my entire philosophy centers on that debate being fine. I can take it. I actually pay someone to cuss me out for being stupid and then I pay again to spend time in a group where we regularly tell each other how much the group members anger us. It’s called therapy.

So take that as context when I say I wasn’t particularly personally hurt by Brantly Milligan, aka Brantly.eth aka one of the ENS Foundation cofounders, suggesting women who use contraception are perverts. I’d probably be a lot more hurt if I was a gay trans woman who had an abortion though. But I figure that demo might be used to being called evil by Catholics at this point. Like maybe it’s more of an annoyance than existential threat if you are wealthy and privileged enough to be working in crypto. We aren’t really a population that is hurting

Brantley.eth “homosexual acts are evil. Transgenderism doesn’t exist. Abortion is murder. Contraception is a perversion. So is masturbation and porn.”

The Ethereum community is experiencing this speech with a lot of pain, hurt and anger. Brantley was voted out of his contract with True Names Limited the foundation that manages ENS Domains. But he remains one of the largest holders of tokens and will obviously have plenty of influence over the future of the platform. The debate has become one of cancel culture versus DAO governance working as intended. But the split on that is not clean and it’s not always clear where people will fall. An informal poll on my timeline is pretty evenly split.

Twitter poll asking if Brantley termination is governance working or cancel culture.

I’m tempted to assign him my tokens as a delegate to be honest. Though I won’t because I think he’s unprofessional. But I want to because I don’t love how any of it played out. Brantly doubled down on telling folks to fuck off compounding the feeling of being hurt. That’s unprofessional and not the kind of behavior I’d expect out of my management team. But I also don’t know that simply holding unpleasant or intolerant beliefs is enough. And it shouldn’t be in a decentralized system. I respect that the right voting and governance may have happened here but I’d argue we all want more control spread out over more people for exactly these scenarios.

I think Brantly basically Shrekli’d himself by doubling down on asshole antisocial shit and the DAO equivalent of the Feds coming for you happened. You can’t attract negative attention and be shocked when bad shit happens to you. But I don’t think being a retrograde weirdo is enough on it’s own to get you booted from an ecosystem.

The entire reason I’m walking you through this sensitive topic today is that I am committing my year to self love. And you might think how does self love and DAO governance overlap. But I really do feel empathy to everyone involved in ENS and the ethereum ecosystem right now. The pain of feeling like you are not seen and loved for who you are is primal shit. This is core human nature “do I belong” to my tribe stuff.

If you don’t love yourself than you are going to have a reactive stance to something that questions your morality and worth. And I’m guessing a lot of people are reactive judging by the uproar. But the thing about self love is that you just won’t be as hurt by assholes being assholes. Because you’ve taken care of yourself first. So whatever the right and just outcome of this ENS governance issue, I think it’s important we all check in on ourselves and why we reacted in the first place. Only then can we get on with the business of design the future and it’s technology.

Categories
Emotional Work Startups

Day 402 and The Most Me

I am coming slowly into 2022 in its fullness. Perhaps I am living in seasonal time this year. I am feeling the wholeness of what the moment brings and January is about becoming. So it wasn’t surprisingly that clarity of purpose has been sharpening for me. I am ready to commit to self acceptance as the theme of my year.

I felt somehow today that the only thing that really mattered for my success in the world was radically altering any perception I had of myself as negative. That I was here to love even the parts of myself that cause me shame and fear. The only thing that will take me where I want to go is loving myself. That self love was actually the key to all troubles personal and professional.

“You know, loving awareness—even if you haven’t heard the phrase before, you know what it is. Those moments of spacious, calm, thorough, tranquil connection with whatever portion of existence you’re currently exposed to, where nothing is being challenged or conceptualized, but rather is just allowed to appear, in radiant suchness, without resistance or fear.

How I Attained Persistent Self Love

I’ve discussed the emotional work I do on the blog at length. The Family Systems Therapy and it’s exploration of the inner child. The shadow work and integrating of the whole of oneself. But I do often reject the crucial step of feeling like I am fundamentally alright. I am ok. I am enough.

I’ve committed to “a bit” where I lavish myself with self improvement and luxuriate in needing to make every measurement better. I’m obsessed with finding metrics to improve. And so I give myself little problems to fix. Maybe I’ll eat poorly so I can feel bad about my body composition. When instead I could just eat what I like and accept that maybe I’ve made other priorities than my figure. I don’t need to agonize over trivial shit.

But equally I don’t need to agonize over big shit. So I’m not a perfectly credentialed super star. I’m more of an eccentric. I don’t live like other people so I see other things. My existence is the selling point. If what I bring to the table is what you want then I am the right partner for you. If am I not then well tautologically I’m not for you. Partnerships are accepting what everyone brings.

So through the end of this year I am going to bring self love and acceptance to my writing here. In letting myself be seen I can more fully bring myself to my partners. Being a startup investor that means I must be present for my founders, their teams, and my own LPs and stakeholders. I’m bringing the full depth of my being because that’s also going to bring the best returns. Because being ok. Accepting the moment and it’s inhabitants? That brings us the creative potential to solve whatever is in front of us without judgement.

Categories
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.

Categories
Startups

Day 392 and Deal Flow

I wrote about my general philosophy about the futility of the typical hour long deck based venture pitch two days ago. I explained that I’d rather have a conversation with founders.

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.

Well since then my Twitter DMs have been filled with amazing chats with founders of companies as diverse as consumer products, marketplaces and web3 games. The stuff people are cooking up in crypto is wild. Thought not enough SaaS tool pitches though so clearly I’ve got to get more mindshare there. Note to self to impress Jason Lemkin or something.

I’ve taken a dozen pitches now through direct messages and chats. It’s worked amazingly well. Maybe I owe a drink to Sam Lessin as he came out strongly against Calendly right after I wrote this post.

So pitch me however you like to communicate. Plus, don’t we all die inside a little every time someone sends a Calendly link?

So I’ve got to say I hope I became known as the slide into her DMs VC as this has been a lot more fun than trying to play calendar sync with dozens of people. That game sucks.

Categories
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?

Categories
Emotional Work Startups

Day 383 and Good at What I Am

Startups are a privilege. You meet people who are exceptional at what they do. Brilliant qualified people who are so capable you could spend your whole life working and only achieve 10% of their innate capacity by natural talent. But the real differentiator is never the talent. It’s the acceptance of who you are. You can’t just be good at what you do. You have to be good at being yourself.

Be good at what you do. Then be good at what you are. Startups require both.

I struggle with this and watch many others who struggle as well. I am brilliant at connecting and amplification but terrible at details and logistics. I used to hate this about myself. I’d beat myself up when I’d get performance reviews that said I wasn’t detail oriented. I thought it was a moral failing. But guess what? It’s just a regular failing. I doubt I’d be great at my actual natural talents if I also had to be good at my failures. Accepting your light means accepting what cast shadows equally.

It’s hard to do. Our coping mechanisms praise us for our good traits and claim full responsibility for achieving them on our own merits. Equally we disown and assume divine intervention or forces outside our control drive our vices. We cannot be responsible for our failures. We only like to take responsibility for our wins.

And I get it. Accepting your shadows is hard. Our parents and our social circles show us who we are supposed to be. Show us what to strive for in the good life. If we are loud we are told to shush. If we are shy we are urged to socialize. Acceptance oh who we are isn’t encouraged. And for good reason. We must push to grow. To become an adult requires effort and work. But we must always remember the ultimate goal in becoming an adult is to become who you are. If you never accept yourself you will never be truly great. And the road is long so start getting good at being who you are.

Categories
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.

Categories
Finance Internet Culture

Day 371 and Never Work A Day In Your Life

I had almost nothing on my calendar today I didn’t want to do. I had small administrative things that took up maybe two hours and that’s excessive by my standards. It’s rare I ever have more than half an hour of genuine obligations. Mostly I just go where I feel like on any given day. I lay in bed on my phone and I move the world with strangers on the internet.

I’m not sure how I optimized for this kind of idyllic work life. I certainly didn’t used to live this way. When I was a founder I was constantly at the mercy of meetings I didn’t want and obligations I wanted to shirk. I always felt put upon. I never felt more like hustle culture owned my life than during my founding years. I was constantly optimizing and I felt like I never had any relief.

Maybe it’s the pandemic. Once we stopped with offices and workdays and all their attendant events and activities, life got a lot better. Everyone kind of settled into routines that made space for what mattered most to them. We no longer had cocktail parties or conferences. Thought leadership stopped being keynote speeches and started being shitposts on Twitter.

I don’t know what the fuck I did it exactly to free myself from that over scheduled fate. I’m so much happier and more efficient. I get shit done and I am less stressed and working fewer unnecessary hours.

Maybe part of it is that I might be a better investor than I was a founder. I could spend the whole day skipping through direct messages and sharing insights in Telegram group chats or having product breaksdowns in Notion. I’m actually good at what I do now. I bring more value and I do it more quickly. Maybe this is what real optimized work is like. You are so good it’s easy.

I’m so fucking happy right now. Over the last hour I’ve done more to advance my deals, connect my community and dig into shit that I genuinely passionately love than I thought I could do in an week. It’s like winning the lottery. I cannot believe I make money doing this.

I basically gossip all day with super smart people and then trade a bunch of densely coded social signals. Those all translate into money. I plot elaborate stories with fellow degenerates with deep aesthetics and then we send it into media zeitgeist. It’s like I work in fashion but the pay is much much better. So I guess it is true what they say. Do what you love and you never work a day I’m your life.