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
Finance

Day 684 and Newcomb’s Paradox

I like mathematics. I’ve got very little talent for arithmetic but formal proofs were something I could feel my way through. I only learned this by failing regular calculus so badly and getting rescued by my roommate who is the scion of a very important family in algebraic topology. Bet you didn’t know that was a thing did you? He showed me that mathematics isn’t about numbers at all but about the logic of the universe. Also he kept me from flunking out. Thanks Tom!

I know the above sounds silly, but in academic circles math is one of those “purest” of institutions where cognitive processing power matters a lot and absolutely nothing else. They are some of the most deeply impractical and removed from reality types of humans you will ever meet.

I’m autistic enough that I found the company of this type of human deeply comforting as they comforted me though my shame based need desire to be normal. Literally no one will make you feel more normal than someone that works in formal logic and it’s adjacent philosophy of decision theory. I bet a lot lot of pretty girls with daddy issues have found this to be true if the LessWrong community is to be believed.

Because of how close I was to my roommate (and still an even though we don’t see each other enough) I got to spend time with a lot of utterly bizarre math people. And it really runs the gamut from those who are functionally pirates who can barely feed themselves to the founders of Renaissance Capital. They are a good time generally speaking. Extremely chaotic people who drink thousand dollar bottles of champagne from solo cups while discussing science fiction are my definition of a good hang.

But they are not what you’d call standard issue humans. If you’d like to know exactly how, ask them to explain how being three standard deviations from the mean has affected them and don’t interrupt them for thirty minutes. I am an outlier in many ways. But I don’t hold a candle to some of the folks I got to meet.

The reason I titled this post Newcomb’s Paradox is because it is thanks to early exposure to mathematics that I got to explore the complete irrationality of rationalism. Newcomb’s Paradox in its simplest format tells us that in an irrational system it is not rational to behave rationally. It is a paradox because this is both true and not true.

If you have some common sense you are not immediately knocked on your ass by this revelation but it turns out to be so unnerving. Unfortunately for some folks at the edge, which is most folks who are mathematicians, it might also break their brain. Effective altruism is now being blamed for its adjacency to the entire Sam Bankman Fried committed fraud at FTX scandal because they took the paradox entirely too literally and not at all seriously.

And given the dangers that can come from extremes perhaps more of us should be spending time with mathematicians. Math pirates when combined with high finance and potent philosophies might need tempering by those of us only two standard deviations out.

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 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.

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.

Categories
Finance Internet Culture

Day 651 and Best Guess

I’ve loved the discourse of indignation that has surrounded rich men doing deals via text messages. There was lot of hand waving about the death of genius and the meaning of it all. Isn’t it such a scandal our best and brightest are just saying shit on Twitter DM?

I suppose if you never worked in startups or finance it might come as a genuine shock that rich techie people are no better or smarter than anyone else. Why the fuck do these dorks control all the money and resources then? I’d say it is because they are willing to make their best guesses.

One of my favorite scenes in Star Trek is Spock struggling through a series of calculations and informing Captain Kirk that he may need to make a guess. Kirk’s response? That’s extraordinary! Spock is naturally confused. Dr McCoy or Bones has to do some translating.


Bones: He means that he feels safer about your guesses than most other people’s facts.
Spock: Then you’re saying… it is a compliment?
Bones: It is.
Spock: Ah. Then I will try to make the best guess I can.

Star Trek IV The Voyage Home (The Whale Movie)

Everyone is just muddling through and making their best guesses. Even the best and brightest among us are struggling to make it all work. I’m not suggesting the folks making the Twitter deal are as good as Spock but they are just making their best guesses too.

And for whatever reason they are willing to put a lot of money, time and reputation on the line to see where their best guess might go. That’s pretty courageous in its own right.

Categories
Aesthetics Community

Day 650 and Reaching

Yesterday was quite a day. I decided to commit to doing a fundraise for chaotic my fund in public as it was my 39th Birthday

I would like to raise $5m for chaotic.capital’s rolling fund before I turn 40 next year. #5Before40 has a nice ring as a hashtag right?

If you would like to be a part of the fund grab a spot on my calendar and let’s discuss!

But lest you think I only thought about venture funds on my birthday I promise I did some celebrating with my family and friends. One of my favorite girlfriends came up to visit. She went straight from the airport to the food cooperative and stocked our half empty fridge with a full harvest of food.

A well stocked fridge

She then proceeded to cook a gorgeous dinner with grilled chicken and roasted cauliflower along with kale chips and a big mixed green salad with a shallot and fresh fig dressing.

Gorgeous, health and nourishing.

And lest you think the most important part of a birthday was forgot here is a picture of the most impossibly beautiful chocolate cake I’ve ever seen.

A chocolate birthday cake

I had a wonderful day filled with love and support. It’s only taken a couple decades but I am finally feeling like I’ve built a life where I feel secure, loved and cared for by those I’ve chosen to be in my life.

Categories
Finance Startups

Day 649 and Build in Public

People love building in public. The universe loves a specific ask. Today for my 39th birthday, I am doing both.

I would like to raise $5m for chaotic.capital’s rolling fund before I turn 40 next year. #5Before40 has a nice ring as a hashtag right?

Chaotic is the first check into founders and companies that adapt humanity to complexity. Personal flexibility, organizational agility, and societal sustainability.

Our founders capitalize on chaos.

You may have noticed I’m a bit of a doomer. I keep close tabs on the opportunities presented by an increasingly unstable world.

Climate change, distrust of institutions, geopolitical unrest, resource scarcity, rising tides of populism. There are founders who can help us address and survive these pressing issues.

My goal is to raise $500K per quarter via a rolling fund. There is 155K per quarter committed from folk like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company.

With a base like that, I want to do the rest in public here on the blog and Twitter. You can read the fund overview here. Building in public has generally been my preference and it has felt weird doing any of this fund work quietly behind the scenes.

You can 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.

I’ve got big ambitions for accelerating into maturity as I have no intention of letting entropy win.

Humanity deserves progress, and I demand growth for myself. I’d like to make us both money with that. 

______________________

FAQ TIMES

Haven’t you been investing through chaotic before? 

Yes but just with personal capital and an SPV. I want to scale it up as we believe our performance warrants it.

Go check out some of our best investments here. https://chaotic.capital/fund-overview

______________________

Why didn’t you raise more during good times? Why the fuck are you raising a rolling fund at the end of the world?

Did you miss the part where I am a Doomer? We are a bad times fund. This moment is where our thesis matters.

Good times return and you’ll appreciate having written a hedge check or two into weird companies that are designed for the power laws of institutional chaos.

Or if the fear of the moment feels overwhelming you can sit back and die the slow death of uncertainty. Trust me I’ve considered it as well.

But personally, I’d write me $10,000 check and come along for the climb back. Entropy only wins if we don’t fight back.

Categories
Startups

Day 645 and Progress

I was recounting a few pieces of work that have been ongoing to some family last night. Both items were the result of choices and trends I’d been following and cultivating for well over two years. One of the items was even set to debut next week. I had some demonstrable proof points that I was right and right long before anyone else took any notice.

I was extremely pleased to recount the long arc of work that had gone into these trend lines and how they were manifesting in successful investments and media attention now.

Usually when someone asks me what I do I have a tendency to stumble around a few more or less goofy bits. I am retired from working in propaganda. I am a house wife that manages the family budget (this works only with stay at home mom or high net work wealth managers). If I’m feeling chatty I explain the Thursday Styles Problem. If I’m not feeling chatty I’ll just say I’m an investor. Occasionally I will make an attempt to explain the founder to angel investor to venture capitalist career arc.

It’s not actually that easy explaining work that involves years of waiting. If you work for an established name brand venture capital firm it’s probably easier than being an angel investor with a small syndicate or seed fund. But even if you are Sequoia it still takes a decade on average to prove out your bets.

I’m thrilled to have concrete examples to point with any of my investment thesis points. I’m lucky that I have exposure to media so I occasionally get the chance to share what I work on online and in print. Not everyone has the skills to be as visible as I am. But it sure felt great to make some progress. And yes I promise I’ll share publicly when I can.