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Emotional Work

Day 707 and Self Discipline

In case it’s not readily apparent from the fact that I’ve written for seven hundred and seven straight days, I am very good at personal discipline. I can will myself to do almost anything. But this gift gets tangled up in negative emotions easily.

Part of this internal sense of discipline is the very clear set of norms I got as part of gendered expectations for good womanhood. You must exert ownership over yourself. Because without doing so, you will be unable to do the work that is expected of women.

You just discipline yourself to serve others. Because women must put other people’s priorities and schedules ahead of their own. Women must be accommodating. Women must be nice. It’s all a very careful training to insure you’d never consider stepping out of line. At it starts at self discipline.

Deviations like weight gain or chronic tardiness or looking unkempt in public were roundly censured in popular culture. I internalized all the ways in which I needed to be constantly improving, fixing, bettering and otherwise making sure I was showing up as others wanted me.

I am slowly unraveling the ways in which this has shown up negatively. Now as I try to unlearn my own obedience I find unproductive ways to rebel.

A small list of the ways this manifests. I hate external deadlines. If someone tells me I must deliver by a specific time I get anxious. If I have a morning appointment r my body wakes regularly through the night to check that I’ve not missed it. Calendars and schedules evoke feelings of despair that go back deep into my childhood. I’ve clearly been learning and unlearning this pattern for sometime.

I am deeply grateful for having discipline as a friend in my life. I have excellent habits in many areas because of it. But making it a true friend will take more time. It’s one of the hardest pieces of shadow work I’ve ever done.

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Culture

Day 700 and Focus

I’m noticing a latent fear in the startup management classes. How do we know if people are focused? Maybe it started with work from home skepticism. But now it’s become an all encompassing yet amorphous fear that nobody is focused anymore. And I have a theory.

It’s all projection. The fear is coming from inside the house. The world is so chaotic everyone is struggling to stay focused. This includes your manager. This includes your manager’s manager. Even your CEO is struggling to shake off the clinging entropy that emerges from constant crisis. And because shit rolls downhill everyone is now flailing around attempting to show they are doing their jobs even as they know they are failing. Even though it remains unsaid because it’s impolite to tell your boss he can’t focus.

The constant chaos that is tugging on our collective capacity to focus is quickly eroding our entire social contract. Not because no one does their jobs anymore. But because we want to be set up to succeed. Because “doing your job” is a point of pride for most people. We like to reliable even if we know there are limits to what we can deliver. So collectively we are hyper vigilant for fraud even as we lack all accountability to each other because we’ve got to protect ourselves first. Self care right?

I don’t see how we get out of this state of fight or flight without a significant changes to culture. Surveillance capitalism isn’t very effective at driving value. It is very good at exacting any drops of it from people attempting to maintain their own dignity. See for instance the railroad workers who have no flexibility in their scheduling. Now with added Congressional oversight!

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Culture

Day 686 and Code Switch

The social contract in America is breaking down but none of us have agreed on the new rules yet. Of course, some populations have never lived within the consensus social contract in America.

And yes there are a lot of Americans that don’t live inside our social contract. Being black or queer (or god forbid both) even in 2022 means speaking a foreign language in your own land. If you aren’t familiar with the term code switching I’d encourage you to look it up.

I’ve almost always lived within consensus norms. At least appearance wise. I pass as a nice white lady with a nice seems white husband. He’s Jewish so only the incredibly woke or the incredibly racist disagree. Though eventually even that protection may give way if we don’t have children.

Code switching isn’t cost free. You’ve got to think about your audience constantly. You adjust who you are based on the acceptable norms of discourse. And it’s an exhausting exercise if you’ve never had to do it.

One of the reasons Twitter has been such a combustible place is that people code switch all the time. If you get caught in a context collapse situation where what you said is fine in one community and heresy in a another you might find yourself getting canceled. Speech norms have always been context dependent.

I’ve recently become more aware of how much code switching I do because I’ve been trying to solve a problem that isn’t considered polite to have in rich stable white American society. If you follow me closely you know it’s related to immigration.

I really need to fix this problem so I’ve been asking around quietly and obliquely trying to sense my way around adjacent communities with rules that won’t turn me into a pariah. And it’s a ton of work. It requires the kind of sensitivity and social graces I’ve previously prided myself on only to discover it’s just the rules for the Western upper class whites. Everyone else knows justice isn’t for them.

As you might imagine plenty of people live with entirely different contexts and social graces than the Eurocentric worldview. And they are all fully and completely aware of the indignities of my problem and the varied ways in which one solves for it. And no one is judging me for it. But it’s been a bit shocking to me. I fully believed playing by the rules would eventually reward me. And of course that’s the real reasonable we code switch. Because different rules apply to different people.

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Emotional Work Finance

Day 683 and Goverance

I’m not a big fan of early stage venture investors meddling too much in the day to day of their portfolio companies. Asking for too much reporting and too frequent board meetings can be a huge source of momentum friction.

But I am a big fan of corporate governance. Even right from the very start. You should have agreed upon avenues for settling issues and disputes from the moment you have assets bigger than an Ikea couch let alone a 32 billion dollar valuation company. A lack of governance structures can lead to deeply destructive behavior even if you aren’t a sociopathic rich kid bent on committing fraud.

As much as it may seem irritating to set up formalities like a full board and agreed upon voting rights structures, you will regret not having it if something goes wrong. And something will go wrong. I’d go so far as to say Murphy’s law is an immutable law of the universe. What can go wrong will go wrong.

The intense pressure of a startup is what turns the lump of coal that is your vision into the diamond that will be worth something in the open market. And pressure is often destructive. People who otherwise respect and trust each other can slowly find themselves deeply at odds.

Just think of your worst breakup and imagine that intensity playing out in ways that impact everything you’ve worked to build. If you’ve ever gone through a divorce I’m sure you understand. Let me tell you a little story about one of my breakups to illustrate why you should set up governance right form the start.

My easiest personal breakup was also one of my worst. We’d moved in together and devised an elaborate set of budgets and savings protocols. We’d combined belongings. We even set up a shared bank account. He was a corporate governance lawyer at a very aggressive firm. I was working a lucrative corporate job but preparing to go back to startups.

While he wasn’t a contract lawyer, he did have enough common sense to suggest we write up a relationship contract complete with dissolution protocols. I thought this was absolutely brilliant which I’m sure tells you a lot about how I operate. Absolutely all of our friends thought we were nuts. Including a colleague and friend who would go on to be one of my board members down the road.

I was in Colorado for my mother’s wedding. I’d expected my boyfriend to join me. But we’d been discovering that all our good faith attempts to arrange the perfect relationship structure was nothing in the face of widely disparate personalities and risk tolerance. No amount of mitigating structure could overcome those differences.

When I came home he’d triggered our breakup clauses and moved out. Everything was done by the governance protocols we’d set out. If I’m absolutely honest I was relieved. My biggest annoyance was losing the Vitamix blender that was his property. As furious and heartbroken as I was at the time, I didn’t have any avenue to engage in my worst most defensive reactionary emotions. Neither did he. Which was extremely valuable as I hadn’t at age 26 gone through the therapy that helps me productively channel negative emotions now.

My ex-boyfriend and I are still friends to this day. Sure it took a few years for us to come around but we’d avoided a scorched earth situation despite the significant risks we’d engaged in by moving in and combining our lives and fortunes after a relatively a brief period. The damage was mitigated by a shared understanding of how we’d manage downside protection and whose rules we’d consider binding.

While I’m sure this sounds a bit weird, I do think it’s a helpful illustration of why even the most optimistic scenarios benefit from guardrails and mutually agreed upon avenues for pursuing a dissolution or change in status.

No matter how calm and rational you think you are, there will be scenarios that trigger deep emotional patterns. If you vomit up those childhood coping mechanism emotions, you need to clean it up even if it feels shameful and embarrassing.

I’d also say it probably tells you a lot that I’m telling you a deeply personal story about a breakup in a personal relationship and not my actual board experiences. There are some secrets you take to the grave and how you failed your business partners tends to be one of them. How they failed you is another. I’ve had reason to be grateful for corporate governance guardrails at all of my companies. Because that is human nature.

So no matter how early it is in your startup journey you should be considering how you’d handle tough times. Set up a board to help you work through and arbitrate disputes. I know you cannot imagine it now but you won’t regret it.

No one is ever fully immune from disagreement (or even disaster) and you owe it to yourself and your partners to set up fair resolution issues from the start. Plus if you happen to have partnered with a sociopath you will appreciate the modicum of protection offered by binding contract law or consensus mechanism contract execution. And if you really want a Vitamix make sure you put that in the contract.

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Aesthetics Emotional Work

Day 681 and Boob Tube

In a sign of how emotionally over this week this week I am, the first thing I thought when I woke up was “I’ve got so much good tv to watch!”

I wasn’t allowed to watch television as a child. So it’s a bit ironic that it is my personal view as an adult that television is America’s best developed art form. While one can’t deny that impact American film, music and fashion, it is our television that moves global culture. Only Bollywood and anime have even come close to its impact in the last several decades.

I truly love television as a cultural mirror. I don’t think you can work in any of the culture industries (including Silicon Valley) without being aware of the mythology of television. Our archetypes and tropes are reinvented and reimagined over and over as references become anchors. No art is so naturally effective at reinvention as television returns episode after episode and season after season. No story is ever finished.

I’m particularly pleased that so many stories are returning this weekend. I’ll be watching new seasons of Mythic Quest, the Crown, Yellowstone and the Good Fight. Which is quite a lot of television for one person even on a weekend where you want to do nothing but tune out to the boob tube.

I’m only adding two two show new to my rotation this season and one is the absolutely excellent William Gibson project on Amazon called Peripheral. No one has ever done the near future as well as Gibson and his take on the Jackpot is already playing out. My last public event before the pandemic hit was a reading of one of the books that this shoe is based on It absolutely deserves wider recognition.

The other is a show I just began is called Reboot. It is an is oddly not at all solipsistic look at making a sitcom from the vantage point of formerly estranged father daughter pair of show runners. As someone who also followed in the footsteps of her father and has complex feelings on abandonment and family legacy it has been quite a comfort over the last week. As I look at history repeating within the context of my own family and within the wider financial markets, I appreciated considering that perhaps we are capable of overcoming our traumas. And that maybe all our parents ever wanted was for us to learn from them.

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Emotional Work Finance

Day 680 and History Repeating

I found myself crying my eyes out to my therapist this morning. Just full on sobbing. Nothing bad actually even happened to me during this week’s chaos. In fact, I’ve spent the last year or so preparing Alex and I for a downturn. I wouldn’t be much of a doomer if I didn’t swing into this downturn prepared.

It just all felt too familiar. It felt like the worst days of fear and insecurities from my childhood playing out all over again. My family went bankrupt during the great Web 1 unraveling. And I’ve never forgotten it’s lessons.

I remember feeling like I was in a secure situation and then learning in dramatic fashion that it was all gone. That all the hopes, dreams and aspirations that my father had done so much to prepare me to reach for (including a lot of very expensive colleges) would likely be out of reach. We’d be starting from scratch again. I hadn’t really had a lot of time to enjoy being a poor little rich girl. It was over too fast.

My father is a truly entrepreneurial man. When I was born the family lore is that he was pitching a edtech company. We were a startup family. We lived in Fremont which is (was) the shitty poor town. I suspect it was a lot harder than I even remember.

But dad found a way to realize his Silicon Valley dreams. He brought software to millions of people. He really did do the thing. And for a few years during the boom times it felt like we might be wealthy forever.

But finance is tricky. Lock ups can fuck you up. So can leverage. We had both. And then of course regular old fraud happens too. Yay.

But it wasn’t in vain. I learned those lessons well. I swing big and I bet on the future like my dad. I believe in people and in genius. But I also keep a balanced portfolio and back up plans.

I believe in exponential growth. But I also believe in the cost of capital. Sometimes money is cheap. Too cheap. And you need to prepare for when capital is expensive again. Because the laws of physics tell us that energy cannot be created or destroyed. And until someone smarter than me proves the laws of thermodynamics wrong, I will operate based on them.

And I am ready for the dark days. Both because it is literally November but also because I believe we’ve got chaos ahead. And if I’ve learned one thing from my childhood it is that you can survive it. It just takes a little bit of preparation. Which I’ve done. Everything else is just a case of history repeating.

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Emotional Work

Day 672 and Self Confidence

My therapist yelled at me this week.

How are you so good at being objective about business but so bad at being objective about yourself?”

Dagmar

My therapist is not what you’d call the warm fuzzy type. She’s more of an old school “dig deep into your childhood trauma to overcome your self limiting beliefs” type. She’s also in her mid-eighties. They really don’t make them like they used to.

My inner child is still fighting the battles of pre-rationalism where everything is about core emotions. Do I feel love? Do I feel fear? Do I feel shame? And my adult needs to parent her with the comforting objective reality that she has nothing to fear and is deeply loved.

I did not feel loved as a child. Without getting into my parents particulars, there was a belief I absorbed that that the path to secure love was through improving myself. I wanted authority figures to see how hard I worked and how dedicated I was to fixing my flaws. It’s hard to imagine someone as brash as I am as a good girl archetype but I was a Daddy’s Girl.

Nevertheless it is true that I get caught in self improvement loops. I’ll fixate on my trackers and personal data and fuss and futz about how things could be better. And I have to consciously remind myself that outcomes are what matter not “trying really hard.” Ironically I have no problem with reaching challenging specific outcomes. I have problems rolling back my inputs to only what is necessary to achieve my outcomes.

Now my therapist is no slouch. She’s one of the smartest and best connected women I know. She is more than qualified to rate my mental acuity and processing power. And she’s now on a mission to remind me of the fact. She wants me to have self confidence in the objective reality that I can achieve my desired outcomes.

And she is correct. I am not being rational in my assessment of my own capacity and talents. I let my inner child’s fears well up and her illogical viewpoints do my adult no favor. In reality I’m competent, capable and absolutely good enough to compete in the arena.

I have an uncanny sixth sense for future market moves and social trends, a numerate mind with a literate education, and all of the skills necessary to source and invest in early stage startups thanks to years in the trenches as an operator and angel investor. If you’d like to invest with me I am objectively very good.

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Emotional Work Startups

Day 655 and Accountability

Being accountable to myself is much harder than being accountable to someone else. I suspect this is true for most people. We all wish for ideal childhoods with parents who provided for all our emotional needs. And so we look to bosses, spouses and authority figures as substitute parents.

Most of our adult lives are spent trying to find some ideal mommy or daddy to soften the trauma and lack of our childhoods. We remember these issues far too vividly as adults through the perceptions of our inner child. It is a huge challenge to recognize that feelings are not facts but these feelings nevertheless run our lives.

The unfortunate truth is that the only ideal parent that can ever exist for our inner child is ourselves. We must comfort, protect and nurture that part of ourselves that still feels lacking because no one else can give it to us. No one is coming to save us. We are the parent to our inner child.

Which brings me back to my challenge with being accountable to myself. I struggle to care for myself the way I need as I too often perceive myself as not being good enough. If I just worked harder or spent more time preparing or if I just did one more pass on my pitch deck. You get the idea. I’ll push myself right over the edge of success into inaction and self torture.

One way I’ve been able to overcome this need to push myself into a fantasy of accountability is simply by building in public. If I’ve said what I plan to do then I’m no longer just cultivating it inside myself but I’ve let the idea come forth into reality. Once it is outside of my own tortured bubble of personal accountability it can gain momentum.

I am raising money for a venture fund and now that I’ve put that in public it’s not just about me. It’s about the thesis, the LPs, the founders, and the market. And it’s much easier to be accountable to a shared reality with other people than some fantasy version of perfection inside my head. If you’d like to be a part of it and are an accredited investor here is a link to my calendar. If you’d like to read more about the fund I’d be thrilled.

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Emotional Work

Day 648 and Open

I share a lot of myself online. For an introvert with more than a hint of Autism you’d think I’d find it mortifying to be as open as I am online. My therapist would probably say it’s because I like the distance provided by sharing online and it’s hard to disagree. But I like being open to the world. I want to be a little beacon in the storm so that you might find me if you are looking.

But while I am so open to the public online, I am protective of my personal space for a number of reasons. I guard my health and my body as I manage a chronic disease. I prefer to operate from a place of non-reactivity as I like my central nervous system to maintain eustress. And I am not generally energized by spending time with others. I am energized by alone time.

But like any other human I do want to be seen. And I want others to feel like I am seeing them. I prize empathy and openness. Showing my vulnerability and weaknesses with the world is part of how I try to be seen and also let others know I see them.

My efforts to be healthy and my struggles with pain and fat are human problems. Maybe other aspects of my life are less relatable, but being worried about my weight and struggling with physical discomfort is the stuff of being an average woman.

I am perhaps overly sensitive to what I perceive as failures and short comings. I project confidence but it isn’t always natural. But I also recognize that, even if flaws terrify the part of me that is still emotionally a child, these supposed failings are the human condition. Everyone has elements of their bodies, their emotions and their intellect that they occasionally feel shame about. We are all working to let go of that shame.

I want the people I work with, especially the founders who are pouring their lives into their companies, to know that they are psychologically safe with me. Doing new things is hard. Creation is hard. Building is hard. Startups are hard. Shouldn’t your investors and advisors be a safe harbor to share those challenges with?

If you are feeling scared or ashamed or angry about yourself, I want you to know you are not alone. It’s ok to be open about your power and your accomplishments and your unique genius. And it’s also ok to be open about all the things you struggle with as well. You contain multitudes.

So if you see me putting out huge asks online or sharing incredibly embarrassing details, I want you to know it is because I see you and I trust you to see me too.

And if we are meant to be in each others lives then it will because we are capable of seeing the multitudes in each other. And if that is not for you that’s ok too. We all deserve to be loved as we are. I trust you. And I hope you might trust me too.

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Emotional Work

Day 647 and Socializing

I thought I was being quite careful this weekend about not over socializing. Last weekend I was hitting up pancake breakfasts and running errands and I thought I was going to pass out come Monday. So I was much more conscious of needing to rest and privacy this weekend.

But no matter how much I dial it back it seems like any amount of interaction is just too much. I backed it down to two hours on Thursday, Friday and Sunday with a recovery day on Saturday. But here I am on Sunday afternoon fighting off a migraine from overstimulation.

Folks bitch and moan about Zoom and how it takes away from the human element of interaction but fuck me if that isn’t the entire appeal of it to me. I myself prefer asynchronous communication to buffer myself even further from the onslaught of audio, visual and emotional inputs. But I’ll take a day full of Zooms as it’s still so much less input.

Perhaps the downside of having the hair trigger central nervous system of an autist is I am simply absorbing more from the inputs than the average person. Every noise, every visual cue, every smell is hitting me. Others may need all those cues but I absolutely do not.

I wish there were a way to articulate this to friends and family that didn’t make people feel rejected. But socializing in person is simply so taxing for me that I need much less of it. And it’s not because I don’t like you. It is just because I’m absorbing way more of you than you think!