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Emotional Work

Day 693 and Thanksgiving

I’ve got so much to be thankful for this year. And it’s the first time since the pandemic began that I’ve felt optimistic about where I’m going with my life. Even if I’m a bit of a doomer, I remain a believer in the human capacity to figure shit out. The road to tomorrow is long and bumpy so best plan ahead.

I’ve had a certain worldview for a while. That we may have some hard years ahead of us to earn back the heights of our boom. Nothing in life is free. And we dined out on energy and resources that had hard costs.

But I prepared for the possibility that life might be harder. I got us to our homestead in Montana this year. To think before this year we’d never owned a piece of property before. It just wasn’t a possibility for so long and then we bounded up on the flush years and found a way to realize some gains.

So I’m grateful that on this cycle of the churn I’ve played it well and fair and I’ve set my family up to work and thrive during hard times. We didn’t get over our skis but neither did we fail to prosper. And for that I am grateful. I am thankful to have been able to play to higher standards but also not gotten eaten by the bigger beasts of capitalism.

I suppose it’s also no accident that I’ve also felt I’ve been thriving in my personal life. I’m so thankful to have made progress on becoming more myself this year. It will probably in hindsight be a demarcation between some of the compromises I made in my youth and some of the boundaries that have led to maturity now.

The more I let go of old copping mechanisms and become more myself, the better I do at achieving my goals. And I hope I can remember this lesson every day. If I can do that I will always have something to be grateful for in my life. And on this turn of the wheels I am offered another chance to defy the odds.

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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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Emotional Work

Day 682 and Almost

My original handle. The very first one I took into social media. Which today couldn’t function as a signifier in 2022 given the acute gender essentialism culture war. The handle was AlmostGirl.

I began writing in university (maybe 2005) about my deep deep deep ambivalence about adopting any culture or identity symbol of consensus success. How I continued to be offered entry into luxury spaces and class identifiers I couldn’t stay. I continued to fail at being part of the status quo. I could only ever be “almost” the thing. As you can tell I’ve been painfully earnest most of my time online.

When I was younger I regretted my inability to fully commit to what I was supposed to want. I’ve really always failed at attempts with adopting conventional status symbols. I always craved being at the norm of whatever was high status. But I just won’t commit to the bit.

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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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Biohacking Emotional Work

Day 676 and Fall Back

I was up and out of my bed like a shot at 6am. Fall back time chances were in full swing and I was excited to hit then the ground running. My trackers told me I was about 90 minutes short of my average sleep and warned me I would need a nap as I was only partially recovered.

But my overall recovery felt fine. I went about my business of making a cup of fancy coffee and filling out my to do list. I felt motivated and enthusiastic. I was excited for Monday energy.

I had one of those mornings where my focus was total. I knew my priorities and I was excited to feel like my goals were achievable. Maybe it was the change in schedules. But I was ready.

I plowed through my morning like I was young, healthy and full of joy. Which is a bit ironic as a number of my goals were explicitly designed to bolster any weaknesses in my physical body. I take supplements and remedies. I meditated. I did some movement and mobility work. I did the work in my body so my mind could be sharp and fast.

I had three full blocks of deep focus work where I didn’t even feel a moderate temptation to open my phone or check social media. My energy went into shaping my work to the desired outcome.

When I looked back over my to do list I realized I’d been working for six straight hours. It was time for lunch. I could feel hunger and a bit of fatigue come over me.

I was lucky enough to have my afternoon block cancel on me. I climbed back into bed seven hours after waking and promptly fell asleep. My joy and focus were rewarded with the kind of perfect deep sleep nap you wish were possible all the time.

Maybe I’m too sad to be on Twitter and I’m having to do more of my zeitgeist work by hand through each newspaper and blog. But falling back into a deep work slow pace actually speed me up.

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Emotional Work

Day 673 and Balance

A boyfriend who loves to game once called me a glass cannon. I didn’t know what he meant at first. A glass cannon is an archetype in gaming representing a character with high offensive status but little to no hit points or HP.

When a class cannon goes crit they go off. Boom! When facing a glass cannon you’d better hope you kill them before they rock your world. They hit so hard that if they cycle back for another hit you are fucked. Glass cannons are hard to kill despite the appearance of weakness.

Day 409 and Glass Cannon

I like to hit hard and I like to hit fast. And I’d really prefer to recover quietly by myself to bring back my stats.

There are, of course always, things you can do to recover your capacity. If you are in a game they will find little ways speed up your energy bar. Maybe it’s special armor or equipment you need to wear or training branch that improves your stats once you’ve researched it. But what about in real life?

When I have gone “crit” I like to sleep it off. But I also find that time with my therapist speeds up my process. Activities like meditation and mobility work like stretching and yoga also help. Watching trashy tv rests my mind. Taking a short walk outside near our mountains. Reading quietly in bed helps.

There are things that don’t recover me quickly. Having our with friends is only restorative if we share some of the same interests. I love to go down an autistic interest rabbit hole. Going to event like concerts or sporting activists is exhausting. Doing things is my nemesis.

I am being gentle and affirming with myself this week as I recognize that balancing my recovery is important. And I’m proud of myself for not giving in to the desire to go faster. I’m not criticizing myself for impossible standards. I am balanced between my intensity and my recovery. And wouldn’t you know it I’ve gotten a lot done.

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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

Day 670 and Vinegar

One of the nastiest tricks we play on women is teaching them to be nice. You catch more flies with honey than vinegar turns out to not even be true literally let alone as a metaphor. That explains why my fruit fly traps all contain apple cider vinegar. Attracting others is just as much about being firm, and even unkind, as it is about nice.

I got the “nice” beaten into me in the workforce in my twenties. I got lots of advice about being more nurturing. I was told you will only succeed if you are well liked. And I tried adapting myself to be more accommodating. I suppressed a lot of my natural personality, and not terribly well, in an attempt to conform to the strictures of being perceived as nice. Nobody bought it and it made me miserable.

I’ve spent the back half of my thirties learning to get it back. As it turns out being nice is mostly in the eye of the beholder and has little to do with if you are actually an asshole. I learned slowly that having firm boundaries is important in both life and business and if someone reads that as you being mean or unkind well that says more about them than you.

I’m doing more to take care of myself so that I can approach every situations with as much empathy as possible. That way if I have to tell a hard truth and be “mean” at least I can do it with as much emotional presence as possible. I don’t have to be liked or even cater to someone’s emotions. That was always a lie. Being too nice might just end up babying someone.

Now I take care of myself so that others can take care of themselves. There is no attracting with honey or vinegar. There is just taking care to be truthful about who you are and what you offer.

Categories
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.