Categories
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!

Categories
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.

Categories
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.

Categories
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.

Categories
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!

Categories
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.

Categories
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.

Categories
Aesthetics Preparedness

Day 674 and Small Delights

I had a fantastic Friday. My husband was home after a week away. I drove to the airport to pick him up and we decided to make a low key date night of it.

I am focusing so much on little pleasures recently. I’m a teetoler for my health but there was a winter ale on Nitro and I just said fuck it I’d like to experience it. It was creamy perfection. The frothy texture giving way to a smooth dark ale.

We came home to a clean house and fresh sheets. Sinking into our recently improved linens was a perfect moment. Who doesn’t enjoy being extremely pleasant with smooth long fiber cotton? The texture of it alone.

It has been these little pleasures that remind my endocrine system that there is still a life to be lived. It reminds me to be present because if I give myself up the apocalyptic hum I am already living it. The Jackpot has already started. So I am giving myself these absorbing moments of presence.

Without them I’m not sure how I’d be without mindful recognizing the delights I still have. I feel like I’ve been ahead of doomer beat for a while and yet it’s all unfolding within the expected models. Sometimes a little bit worse. You see the scenarios and wonder which will unfold. Which careening variable sets off the Jackpot to a narrowing of humanity we can barely fathom.

I’m keeping my limbic system in check. I am working on not setting off my central nervous system into a sympathetic fight or flight pattern. I’d much prefer to be in rest and digest. I see so much energy being dedicated to fruitless ends. And I will not be lending those ends my energy or focus. Neither should you. Your mind is your own.

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.