Tag: Commitment

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Background

Day 721 and 40 Questions

I came across a list of 40 questions that Stephen Ango answers every year on Twitter today. It looked like a fun exercise so I thought I’d participate.

What did you do this year that you’d never done before? Bought a house & got my very first mortgage, moved to Montana, lived in Germany for a month, spent time on the Ionian and Adriatic Seas, and experienced -45 degree temperatures.

Did you keep your new year’s resolutions? I don’t make them but I did intend to write every single day (for the second year in a row) and I have so far accomplished it.

Did anyone close to you give birth? No

Did anyone close to you die? No

What cities/states/countries did you visit? Colorado, Montana, and Wyoming, Florida and Texas for states. United Kingdom, Germany, Albania and Greece for countries.

What would you like to have next year that you lacked this year? All the money for my venture fund and visas for freedom of movement for my friends and family.

What date(s) from this year will remain etched upon your memory, and why? June 18th was the date we closed on our homestead in Montana. August 1st was the day we moved in.

What was your biggest achievement of the year? Getting my family safely to a Montana homestead that is the first home we’ve ever owned.

What was your biggest failure? I don’t think it’s a failure, but I wish I got more done particularly when it comes to fundraising and deploying capital, but objectively I did as much as I could. I try to remind myself that the self is not an attack vector so this question is an opportunity to remind myself that failure is just opportunity.

What other hardships did you face? I got a very bad flu in the middle of purchasing the house in Montana. I watched the markets repeat elements of the crashes of 2001 and 2008 which allowed me to see how far I’ve come since my childhood trauma of my family’s bankruptcy on 2001.

Did you suffer illness or injury? The flu in May was awful, I’ve had a number of random infections and I live with chronic ankylosis spondylitis but I’m the healthiest I’ve been in years.

What was the best thing you bought? A house in Montana. But smaller things I’ve loved include a Lunya robe, Ariat boots, Skimms cotton tank bras, and my first go at Botox.

Whose behavior merited celebration? My husband has been an absolute superstar rolling with my crazy plans and I’ll be forever grateful he trusts me to see things that he hasn’t yet seen. I’ve written many a love letter this year to him and my appreciation for the ways big and small he makes my life better.

Whose behavior made you appalled? Not appalled necessarily but the dick riders are really a bummer. We are all sinners and ain’t none of us are saints.

Where did most of your money go? We bought a very nice piece of land with a gorgeous farmhouse on it. The second biggest expense after buying a house was medical bills. It’s fun to be sick in America. Third on that list is food both because my husband is a gourmet cook and because inflation on food was quite high.

What did you get really, really, really excited about? Being a homeowner has been exciting as hell. Everything about buying a house and making it our own has been amazing. I also spent a lot of time excited about DAOs and corporate governance, my founders, and spending a month next to the European Central Bank in Frankfurt.

What song will always remind you of this year? I don’t listen to much music so I don’t have an answer.

Compared to this time last year, are you: happier or sadder? Thinner or fatter? Richer or poorer? I am happier, poorer, and thinner than I was last year.

What do you wish you’d done more of? I have a lot of things I want to beat myself up about for not doing more, but I actually feel like I didn’t my time well this year. I don’t always need to be improving things. So I guess I wish I was comfortable doing less.

What do you wish you’d done less of? Beating myself up for not doing more.

How are you spending the holidays? I am in bed with my husband watching disaster porn movies while it is 45 degrees below Fahrenheit.

Did you fall in love this year? I am deeper in love than I was last year which is one of the benefits of always working on yourself and having a partner that also works on themselves.

Do you hate anyone now that you didn’t hate this time last year? I wouldn’t say I hate them but I’ve been disappointed with everyone involved in Elon Musk’s Twitter takeover.

What was your favorite show? The Peripheral. It is the adaption on Amazon of William Gibson’s most recent novels and it is stunningly good science fiction. I’ve enjoyed a lot of television this year though.

What was the best book you read? Hands down Peter Watt’s Blindsight which I cannot believe I didn’t read till this year. If you are autistic I in particular recommend it.

What was your greatest musical discovery of the year? Again I don’t really do music.

What was your favorite film? I’m not a big film person so I didn’t watch a ton of movies this year. I’m a TV person. But probably the Weird Al parody biopic. Extremely funny and very sweet. Worth taking the trouble to find on Roku.

What was your favorite meal? I’ve had so many amazing meals this year. Perfect Montana steaks is probably at the top but schnitzel in Frankfurt, branzino in the Mediterranean, BBQ in Austin, and stone crabs in Miami round out the list. I traveled a lot this year and that means I had a lot of great meals.

What did you want and get? A homestead in Montana.

What did you want and not get? A visa for a family friend. American immigration is extremely broken. I’m hoping I get the visa granted next year for them.

What did you do on your birthday? I discussed my “fundraise in public” for chaotic capital and spent it with Elle Morrill and my husband. Elle cooked for me and it was absolutely epic.

What one thing would have made your year immeasurably more satisfying? The American immigration system working. But that’s like asking for world peace. I spent a lot of time and social capital trying to get a visa that still hasn’t been granted.

How would you describe your personal fashion this year? Black. I mostly wear cotton black sweats and a long sleeve cotton tee-shirt. My biggest upgrade to that look was adding in a Lunya robe. But I also bought a bunch of chore clothing for working on the homestead. I also got to enjoy my “heat” wardrobe which is mostly Grecian gowns made by Norma Kamali.

What kept you sane? My therapist Dagmar and writing every single day.

Which celebrity/public figure did you admire the most? Folks hate this answer but I love Kim Kardashian. She works her ample ass off for her family business, spends her time working against the carceral state, makes a great bra and she started a private equity firm.

What political issue stirred you the most? The government’s interest in deciding what I do with my own body. I’m a libertarian because the very foundation of sovereignty rests on your right to control your own body. Though this issue is very closely followed by our inability to grant visas and bring immigrants to America in terms of animating my energy this year.

Who did you miss? I miss my grandmother Nanamai. She’s my mother’s mother. She’d be so proud of what I’ve done with my life. I wish she’d be been alive to wear one of my lipsticks. I wish she were alive to see the family life I’ve built. She passed on more than a decade ago and I’m still consumed by grief if I think about it too hard.

Who was the best new person you met? There are almost too many to chose from. Meeting in person my internet friends who got me through the pandemic is the correct answer. You know who you are. And I can’t wait to meet more of them. Internet friends are real friends.

What valuable life lesson did you learn this year? I learned a lot watching hero worshippers, I mean dickriders, beg their chosen figurehead to save them. But alas the only person who can save you is you.

What is a quote that sums up your year? “Fuck around and find out.” But in all seriousness just doing the thing and trying shit out is actually crucial in life and business.

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Emotional Work Startups

Day 719 and Step By Step

I was discussing my goals for 2023 with a friend today. They wanted to know if I was planning on making any New Year’s resolutions. I told them that I wasn’t in the habit of using a new calendar year for making big changes.

Generally speaking if I want to do a thing I just start. I honestly feel like it’s far too intimidating to declare yourself to be some kind of fundamentally new person that will, as of a certain arbitrary day, make huge life changes. It’s too much pressure. One of my rules for biohacking is to only change one variable at a time. And I don’t make big changes to it either. 10% a week is good enough for most goals. Anyone familiar with the magic of compounding knows that small changes add up to big numbers.

Which isn’t to say that I haven’t started big life changing projects on January first. If you count back from 719 you will notice I first began writing on January 1st 2021. I did indeed resolve to write every day. But I hadn’t intended it as something I’d keep up for a specific amount of time. I’d hoped I’d practice my writing for thirty days and I allowed myself a little fantasy about how amazing it would be to write for a thousand days.

A thousand days seemed like an impossibility at the time which is why I allowed the fantasizing. My pragmatic side said just get started and see if you can keep going. And I did. I put one foot in front of the proverbial other for two years. Now I’m relatively confident that if I want to do so I’ll make it to a thousand days.

I approach most goals like this. I had a fantasy that I could make it as an investor. I was a founder so I thought let’s wire some small angel checks. We were already committed as a family to being startup operators so why not combine our skin in the game with a little more capital risk with our network.

I never envisioned myself raising a fund and making some big announcement about how I had a venture fund. I just started learning by doing. I cut checks. I ran some special purpose vehicles. And this year I decided to one-step-at-a-time go about raising a rolling fund. I am just doing the thing one day at a time. And it’s going well. Amazing people are coming on board. I am confident I’ll reach my goals just by putting one step in front of the other.

If you’d like to join me my goal is to raise $500K per quarter. I’ve got folks like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company. You can read the fund overview here. Yoican sign up on Angellist through the above link or get on a call with me and we can discuss the fund, our portfolio construction and my thesis. Because I intend to work through the holidays because it remains one day at a time.

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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 695 and Pareto Focus

Perhaps one of the odder aspects of millennial culture is our enthusiasm for embracing middle age. The excitement of passing into one’s middle and late thirties is palpable on Twitter in particular.

Our Boomer parents still think of themselves as “young at heart”, while millennials are grasping at any semblance of stability that comes our way. Buying a house, watching your children grow up, and acquiring items like minivans are luxury life events.

As culture and civilizational mores careen towards ever more swift changes, millennials are caught between a desire for the stability of previous types of adulthood while also being forced to constantly adapt to new expectations. You are being buffeted by changes that are swift and unrelenting. It is chaotic. You wish fervently to get out of constant fight or flight to the safety of being middle aged, even as the firmaments of past social stability are going down around you.

I believe this is contributing to a serious tension in our work lives. I’m tentatively calling it Pareto Focus to synthesize two concepts. The first being that 80% of the output is from 20% of the work (more commonly known as the 80/20 rule). “Focus” because we have little incentive to grind out focus on the remaining twenty percent of refinement if the rules of the world are changing too fast for expertise to ever be rewarded.

I see this in myself to some extent. I’ve done the work to become a competent working expert in several overlapping fields. I’ve worked in the desire trades including luxury, fashion, and cosmetics.

But I’ve not seen any point in pursuing them to the logical extension of specialization because the chances that the world shifts has always felt too great. Better to understand his desire and attention drive the larger market and refine those skills so even if the winds shifts I will still find work.

This has had a lot of positive effects. I focus on inverting as it allows me to apply the vast array of Pareto knowledge I’ve acquired. And it lets me continue working to intake the 20% of the new so I can I’d enjoy the fruits of the 80% of results.

Obviously I’m simplifying this a great deal. I am genuinely expert in many areas and hold myself to high standards because I’ve met the specialists who have done the long hard road to refinement. And I know where their paths have diverged from mine. Some of it is simply personality driven. Generalists and specialists are needed in any system.

But I do think Pareto Focus might be a phenomenon that’s driving labor allocation and focus in a wider generational way. If change continues to accelerate, you cannot blame people for doing the math on what it takes to survive.

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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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Startups

Day 688 and Hardcore

My generation of founders came of age during the peak of hustle porn. We were young and dumb, and even without the use of stimulants and nootropics like our Gen Z younger siblings, we got a lot done. Probably because we were well young and dumb. And it’s easier to do things with brute force when you don’t have better tools. Being hardcore made sense for some of us.

Alas if you burn the candle at both ends you may find yourself with an astonishing array of healthcare issues in your thirties. Which is astonishingly common in my cohort. I’m just one of the rare examples that is public about the dangers of overworking yourself. Hustle porn’s legacy is mixed. We lost founders to workaholism and occasionally much worse. A generation learned that mental and emotional health are just as important as physical health.

Hustle culture coincided with a lot amazing companies getting built but it’s not entirely clear to me if being hardcore is the only factor at play. Tempting as it may be to look for simple mono-causal relationships in life, the math of success is never that simple. Life isn’t an engineering problem. And even if life was an engineering problem, applying more force doesn’t solve all problems. It might even make a few worse.

I don’t want to knock hard work obviously. Im a firm believer that the basics never go out of style. Hard work is a given. Most of the greats are working hard because once you discover you have a natural talent then maturity generally encourages you to hone it.

Success is built from many fathers even if it’s mother is hard work. Proper resourcing, adequate incentives, teamwork and an effective hierarchy of respect within it are all factors. And let us not forget just plain old good luck matter just as much as being hardcore.

So tempting as it may be to give in to Twitter discourse narratives don’t get fooled into thinking someone that is successful has it all figured out. You don’t know what it took to get there and who brought it together. Don’t overweight success on its own. Nothing is ever that simple. Expect that the team you want to be a part of will demand that you demonstrate all of the above virtues and along with the necessities of hard work. But if it all comes together it is worth the sacrifice.

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Finance Startups

Day 687 and Winter

It’s cold out there. And I don’t just mean metaphorically. Winter came early and hard to Montana just as the Farmer’s Almanac predicted it would. Driving back in from town last night after grocery shopping it was -3 degrees on the car’s temperature gauge just after sunset at 6pm.

It’s cold out there in the capital markets too. The federal reserve is raising rates to tamp down on inflation and the cost of capital is hitting the technology industry. Frankly I think we’ve all been waiting for an excuse to cut the fat and now we’ve got it.

But it’s going to have consequences for startups. Founders who have never had to live with the harsh realities of a down market are in for a surprise. Those juicy valuations in the private markets don’t work so well when the public markets can find safer returns in a Treasury finally paying out on a t-bill.

Let me play with a tortured metaphor to help you understand the situation. You think you understand how cold winter will be until you realize you haven’t had to work through a chill for over a decade. Sure maybe in your closet you’ve got a nice coat but when was the last time you wore it? If it was for a ski retreat with one of your venture partners then this metaphor is absolutely about to do double duty.

Surviving a bitter cold isn’t just about having a bulky down coat. Think of that as your cash runway. Without adequately rated cold weather gear to keep you alive you may find yourself tapping out. But it’s not just about the coat.

Keeping warm and staying productive requires some technique. Do you understand how to layer correctly? Do you have hats, gloves and scarves? I bet you walk around with ankle socks and Allbirds. That’s not going to go well in a foot of snow. Do you know how to eat for the cold? How about hydration?

Your team will need more than runway. They are going to need motivation to work with less fuel. You have to show them that the climb up the snowy mountain is worth it.

A winter startup team will need the skills and flexibility to work around problems that can’t be solved with money. Shit can and will go wrong on a long cold climb out of an economic winter. Creativity and belief must overlap with intuition if you want to make it.

And it’s important to remember lot of your team won’t have those intuitions. We’ve all been living in Miami and suddenly it’s -3 in Montana. And guess who gets to teach them how to adapt? You. You need to teach your team gently and with empathy what it will take. And they will makeup mistakes. Have you ever watched someone try to lace up boots for the first time? You might need to help them cinch.

I promise it is worth it though. If you are climbing the right mountain, and prepare adequately for your journey, the rarified air of a successful startup is invigorating. And the view from the top isn’t bad. If you need some help thinking all this through as a founder drop me a line Julie (at) chaotic dot capital and I’m happy offer some Sherpa advice. I lived though 2001 and 2007 (I even got laid off during RIP Good Times) so you can rely on me for some elder millennial wisdom. Stay warm!

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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.

Categories
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.