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Day 411 and Good Day

I’m flat on my back in bed waiting for my Advil to kick in. I’m the kind of satisfied tired that only comes from a good day. But I’m also in pain as I did so much today that eking out this blog post is a bit intimidating. As with all good things they become bad when you over do it.

I am that stage of tired where I can’t even work myself up to go wash my face. I’m in bed texting and scrolling Twitter and hoping I’ll get a surge of energy to do what needs to be done. Alas it’s been an hour so I think I’ll need to go with sheer force of will.

I packed a lot in today as I’m headed for my first in person event since the pandemic started. I’ll be at Ethereum Denver through Saturday. And in March I’ll be in Europe for the whole month which is another whole thing. Having travel plans means more errands and more preparations than I’m used to incorporating. Which is just such a foreign feeling. Remember when we all traveled a ton?

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Aesthetics Emotional Work

Day 410 and My Own Valentine

I’m quite fond of Valentine’s Day. I like flowers and chocolates and cards. I like wearing bright pink. I like all the hyper feminine consumerism around the entire Hallmark holiday.

I’ve got my own rituals and routines for the day. I used to go to White Castle for their white tablecloth service with my friends. Yes that’s a real thing they do. It’s an absolute blast to get table service when the food is sliders. It’s a wholesome experience that somehow no one does ironically. They once let me take home all the balloons when I had the last reservation of the night.

But I am particularly enjoying Valentine’s Day this year because I’ve made a commitment to self love this year. I came into the day with a spirit of accepting myself in whatever condition I arrive in. It’s a glass half full approach in a time where it’s easy to look for downsides and depression.

I hope if you are considering committing to more love in your life that you start with yourself. That on Valentine’s Day you focus on giving yourself the love you’ve always wanted. Maybe it sounds as silly to you as having sliders with table service at White Castle. But I promise both experiences are far more than a critical ego will allow. Go ahead, open yourself up. To love and little hamburgers. Happy Valentine’s Day!

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Emotional Work Startups

Day 409 and Glass Cannon

I’m one of those “life optimization” types. I spend a lot of time on various wellness applications. My health stack is deep. Over the years I have attempted to integrate more productivity applications into my life. But beyond a basic “to do” list I’ve found myself failing to maintain anything more complicated than ToDoist task list.

I think my failure is related to the challenge inherent in optimizing deep work. A lot of what passes for work in regular jobs isn’t a big part of my work. I don’t have a ton of alignment meetings because I am accountable to my LPs and my founders but not horizontal stakeholders. I don’t have tons of reporting as again the buy-in is pretty contained.

Ultimately I am only responsible for outcomes. And my outcomes will take years to materialize. I’ve got to get conviction on a decision largely on my own. I am responsible for my own success. And yes it’s a little bit scary to realize I’m in control.

This means I can’t fixate on signifiers of work. Which is largely what productivity apps track. The representation of the work is usually what gets tracked and measured. Arguably I can have my own OKRs (objectives and key results) but I’ve not encountered any personal productivity apps that work well for that framework. It basically boils down to the harsh truth that most of my work is deep work and it’s harder to measure. Deep work is the stuff of slow integration and accumulating knowledge up until it turns into catalysts, breakthroughs and ambush predation.

A gamer friend called me a glass cannon. I’d never heard the term before. It basically boils down to a character that has impressive offensive work but little stamina or defensive work. When they hit crit they go off. Boom! When facing a glass cannon you’d better hope you kill them before they rock your world as if they cycle back for another hit you are fucked. Glass cannons are hard to kill despite the appearance of weakness.

I spend my time preparing for action. Integrating knowledge. Widening my horizons. Intaking potential opportunities. None of which is easy to measure and moderate in traditional work culture. But when I go off you know I’ve made a move. It’s clear. Decisive. But the intervening time between? I’m preparing to go critical. You don’t know when or how but then it’s all in. A glass cannon may be the ideal archetype for venture investors.

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Medical

Day 408 and Getting Ahead

My first piece of international travel since the pandemic began is coming up. I’ve not been on an airplane in over two years which is wild. But I needed to get a booster shot for my travel papers.

I was a bit nervous about how I’d react. I didn’t have the easiest time getting vaccinated. But I had a mild case of Omicon in December which made me slightly more optimistic about it.

I got caught in a snowstorm getting the booster yesterday. Which is so far the only inconvenience. I slept fine last night. I didn’t appear to spike a fever. I had no aches or pains other than the ones I live with normally. I’m so far enjoying having little to no reaction.

I did however take very good care of myself. I felt a migraine coming on mid-morning and I rushed in with all the good drugs. I wasn’t going to let myself suffer at all. And I am suspecting that keeping any and all stresses away has in fact been excellent for my body. Just another reminder that drugs are in fact good. Loving yourself can often mean mean treating yourself kindly. Removing the option for suffering and maybe all recovery can be this easy.

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Preparedness

Day 407 and Snow Blind

We’d scheduled booster shots for this afternoon. Even though we’ve both recently had Covid, I’ve got travel coming up so I needed to get a booster to get into Europe. I probably have never had better immunity to the disease than I do right now so I’m feeling optimistic about being around people again.

But I didn’t realize it was going to snow today. The forecast said it would lightly snow for an hour or two. So I thought it’s fine to schedule vaccines now. I wanted them right before the weekend so I had maximum time to rest and recover.

But clearly the forecasts were we wrong as we headed into a significant storm to get our shots. An hour later as we wrapped it up we were in driving snow with very little visibility. The roads were accumulating snowfall fast. The normally fifteen minute drive hour stretched into triple time.

Thankfully we made it home safely. And we’ve been shot up for the sake of paperwork. I only feel marginally worse for wear.

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Emotional Work

Day 405 and Okayness

I wasn’t in my “okayness” this morning. My focus on self love hit a snag on hormones. I woke up with a migraine and menstruation and I wanted to treat myself as an attack surface. So I asked my Twitter feed to tell me how they got to okayness. And it was beautiful.

I am often struck by how if you share your vulnerability with people they will open up with their own. The joy I get from connecting with you in the fullness of being ourselves gives my entire life meaning.

What seems even wilder to me is that this kind of connection happens on Twitter. It’s crazy that out in some virtual world, the metaverse if you will, the most human needs are met. We can see each other on a phone application. It’s enough to take your breathe away.

I’d encourage you to browse the thread as it’s filled with insight. People take long Lindy walks and do their nails. They lower their standards and raise their spirits. They integrate shadow elements into their identity. They take little risks and embarrass themselves. They imagine the tweet they would send at the end of the day with their accomplishments. But most of all people make things. That even when being a human being seems like an impossible challenge our capacity to build gives solace.

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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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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.

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Preparedness

Day 399 and Life Finds A Way

Postlapsarian literature is arguably the first type of story in the human mind. A fall takes place. What comes after? Paradise Lost is an entire genre of folklore. I’ve been watching the new Station Eleven television show having made that mistake of reading the book early in the pandemic. I say mistake because it’s an emotional book.

Maybe it’s America’s obsession with second acts that gives me optimism. We will have a fall. A shuffling towards Bethlehem style shambles perhaps. But we will rise. Our national bird has never been the bald eagle. It’s been the phoenix.

Maybe this is why we tolerate horrible work conditions and miserable days fighting our fellow man for a scrap of security. Because as the saying goes, each of us is only a temporarily embarrassed billionaire. Don’t worry we will be back. The show must go on.

And so we concoct elaborate fantasies about how this too will pass. One day our chronic poor health will get better. Just you wait. We believe in science here you see. Science means an Epcot better tomorrow just hang in there.

Our Hollywood fantasies are riddled with “life finds a way” punchlines because well the struggle for survival in an inhospitable world is a universal struggle for our species. There is no lost cause.

But also there is no enjoying the moment or savoring the little things in life if we are always watering for our heroic moment in “the after” and holding back in the now. But don’t worry. Life finds a way. And so will you. Just remember that the end of the world is mostly a change in circumstances.

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Emotional Work

Day 396 and Drowning

I’m a big fan of the show Bojack Horseman. It’s got all the emotional depth of Ted Lasso but with all the trauma of remembering your never felt loved by your father. Yeah it’s not really a comedy.

For whatever reason it’s a show I typically watch after therapy. I’ll watch an episode or two when integrating all the feelings from paying attention to my inner child for an hour and a half. I know it’s kind of a weird choice but it’s a really straight shot of feelings.

When the star goes on an epic bender, his ex-girlfriend recounts a story about being a life guard.

The first rule of being a lifeguard is knowing when you cannot save someone. Some people they will splash and thrash. And try to take you down with them.”

I’ve got someone in my life that is drowning. I know it. I knew it before they did. My instincts were like the lifeguard trainee. I wanted to help. But they are splashing and thrashing and all that would happen if I tried to help is that I will drown along with them. I know this to be true. But I am so willing to be cruel to myself and ignore it. I’d let myself drown. And what good would that do anyone?