Tag: Capitalism

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Emotional Work Startups

Day 153 and Startup Families

I’ve worked my entire career in startups. I love it. But the work barely compares to being a member of a startup family. My entire life has been lived, literally from the day I was born, in the ecosystem of families that make startups come to life.

I was “in it” from conception and all my success and traumas are in some way tied back to that luck. And I became a startup founder and eventually a startup wife. This post is about what it’s like to live in perpetual uncertainty of creation with the occasional bout of life changing money.

For everyone that has a payday that changed their lives forever, chances are they have spent decades in the shadow of that system of building, scaling, and selling companies. The paydays are sporadic, completely dependent on luck and often extremely unfair. Most of the time the early team sees nothing. I’ve personally had an exit where I got nothing. I’ve had an exit where I couldn’t afford to exercise my options so when the company that bought mine exited I didn’t see a dime. So I know how fundamentally random startup life can be. How unfair it can feel. Because today it is our turn to be the beneficiary of the unwarranted success.

My husband Alex’s long time home Stack Overflow, sold for 1.8B dollars today. And yes we are one of the 61 families that will see more than a million dollars from it. But it’s not all joyful excitement in our house. Because it’s not about not just about money. It never has been. In my family it’s always been about belief. And it’s really hard to reconcile the many competing emotions that come with a liquidity event. It’s the culmination of much work and time from everyone.

My father proudly reminds me that when I was born, he didn’t have a job as he was pitching an education startup. What a blessing to have the energy of one’s life be aligned with risk from the start. And also what a curse. My family had incredible boom years where money wasn’t a concern coupled with devastating financial and emotional ruin as companies went to zero and markets crashed. My father sacrificed so much for his dreams. He saw the value of software and took his wife and children to the promised land of Silicon Valley. And oh it was glorious. And oh how it hurt.

I have fond memories of Comdex, elaborate company cruises and board meetings during “take your daughter to work day.” I also remember my father not being there for birthdays, for dinner, for milestones because he was busy building the future. I don’t remember my parents getting divorced, because I suppressed the memories. Family trauma can be like that. The good and the bad exist at the same time. When my father went bankrupt in the Web 1 crash, I was so angry at him for not being more careful, I didn’t speak to him for years. And then I made the choice to become a founder myself. Despite my fury and sadness and hurt I too decided to live my father’s path. And then I married a man who walks it too. I guess the Bojack Horseman joke got it right.

You inherit your parents’ trauma but will never fully understand it. Haha the cop is a cat.

The day you get news you made life changing money is bittersweet because all the trauma of being a startup family member catch’s you to you. You remember the sacrifice of your whole family going back years. The long nights and missed time together. The choices to prioritize the company over your family. In our case 10 years but of course for me it’s been my entire life.

The entirety of my marriage with Alex and my entire relationship with him before was spent at Stack Overflow. I’ve seen the hard work and the pride. I’ve also seen the exhaustion and the agony when something went badly wrong. The hurt when teammates left and the fear of leaving yourself eventually. People grow up together at startups. Other more practical logistics show that not everyone wins. The hard decisions you make when it’s time to leave and you cannot afford to exercise your options are a unique pain. We just three weeks ago sold something in secondaries to afford the taxes to exercise ours. That’s timing and dumb luck. Almost absurdly so. We could easily not be in the position we are. Exits are the end goal and yet not everyone gets to make it despite equal sacrifices. It’s all random and no one deserves any of it. But it changes your life if it does happen.

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Finance Startups

Day 152 and Running The Play

I’m going to put $5,000 into liquidity mining and yield farming to fuck around and, hopefully, find out.

If the last year has been about laying out the primitives of decentralized finance, this summer is going to be the Layer 2 land grab and I need to learn how to stake some claims. I don’t have a clue if it is going to work but I need to start learning how to play the game by tossing the ball around. I doubt I’m going to be whatever the equivalent of a professional player but I want to learn some muscle memory. You can’t very well buy an NFL team without having ever handled a football can you? Yes I am torturing a metaphor.

On a personal psychological note, I wanted to start with a $1,000 but then I realized the difference between losing $1,000 and $5,000 isn’t material to me (which blows my mind but such is the compounded benefit of my various privileges). However, the difference between 10xing $1,000 to $10,000 and 10xing $5,000 to $50,000 is extremely material to me. $50,000 is a a material seed stage check for a company that I may want to place a long bet on.

That is roughly the cost of my medical care for an entire year (not including drugs which roughly doubles it). That is a down payment on a parcel of land to develop over the coming decades. This is a moment to learn and leverage for the benefit of my future self and family if shit goes well. And if it doesn’t no big deal. The real money is better managed than me deciding I want to toss around a ball

My Chaos thesis says it’s time to run the play on the future more generally. It’s hard to argue that I can make good puts on a chaotic future without fully experiencing some of it myself in visceral fashion. I fully expect to lose all of it trying to liquidity mine and yield farm on my own but if I don’t well then I’ve proved something to myself about the future of capital.

I need to remind myself that this isn’t representative of how I allocate capital in a diversified portfolio to preserve my future security nor is it how I’d allocate capital even in a seed stage private venture stage portfolio. But it is a worthwhile amount to put on a 100% risk basis to learn how the fuck the future of capital allocation might work.

Honestly $5,000 is a pretty cheap tuition for a fancy credentialed college class so this seems like a good deal. I will write my way through the learnings and call it an independent study.

Categories
Finance Internet Culture Startups

Day 151 and The New Capital Networks

A lack of network has generally meant capital constraints if you were an entrepreneur. Being hooked up with capital allocators was crucial to being a good operator. Access tended to compound over time like interest. Which is why we make “funny because it’s true” jokes about how successful founders usually had a head start in a few areas. I’m not saying that is going away, but decentralized finance is fucking with some of the consensus knowledge around how capital gets raised and deployed.

And what convinced me we are moving towards an inflection point, over the next decade, where capital allocators and operators decouple, wasn’t my tony Silicon Valley network. No, I’ve had access to the minds of those players for years. What clicked my mind into a position to take action? I spent an hour and a half getting a tutorial from one of my anon reply crypto friends on yield farming and liquidity mining. I don’t want to blow up their spot but Alpha Ketchum dropped a lot of knowledge on me today. And it shifted my energy from belief into understanding. From there action will be seen in my investments.

I’m still chewing through a lot of the details but I’m going to make a bet that scaling DeFi is going to require significant institutional capital and the support of experienced operators to realize its full potential. Thats why I’m invested in folks like Cambrian and Martin Green and would love to get my dollars into Arca and David Nage. That’s why, of my four thesis areas I’m pursuing in my own fund Chaotic Capital, two are explicitly dedicated to both organizational and systemic flexibility and how it plays out across new business opportunities.

We’ve seen capital decoupling from traditional centralized authority systems and trust based networks. The perpetual fundraising machine of tokens, coins and market making techniques like yield farming, are funding everything from esoteric art projects and to the next generation of insurance. Thing about that, the innovative companies that drive growth won’t have their capital needs met just on Wall Street or Sand Hill Road. If you don’t believe me look at what has already been built

Exchanges → SushiSwap, Uniswap, Bancor, 

Insurance → NexusMutual, Cover

Derivatives → Perp Protocol, Opyn,

Credit Markets → Aave, Compound, Maker

Middleware → Chainlink, Grt, 

Asset Management → Enzyme, Yearn Finance

Aggregators → 1inch and Matcha 

Categories
Finance Startups

Day 149 and Optimizing for Outcome

I came across a thread today by Sahil Bloom on human goal setting and the mental models we manipulate. He introduced me to Goodhart’s Law

When a measure becomes a target, it ceases to be a good measure. If a measure of performance becomes a stated goal, humans tend to optimize for it, regardless of any associated consequences. The measure loses its value as a measure! Goodhart’s Law is states “Any observed statistical regularity will tend to collapse once pressure is placed upon it for control purposes.” But the concept was popularized by anthropologist Marilyn Strathern. She generalized the thinking and called it Goodhart’s Law. “When a measure becomes a target, it ceases to be a good measure.”

I am fascinated by this tendency humans have of fixating on the things we think symbolize progress instead of the actual outcome. Sahil names a number of instances in which this has led to bad business outcomes. CEOs managing to short-term stock goals has been one that has long frustrated me.

Startup land is immune from this tendency either. I’ve seen product teams fixate on OKRs such that they never miss a single metric but fail to launch their product on time. Or a venture capitalist will toss out something like an ARR goal for a Series A only to have a founder chase that number for a year and still not get funded when they hit it. We think these goals are the goals in and of themselves. But really launching the product on time and closing the series A are the only thing that matters. As long as we hit our goals who cares what metrics we used?

This is of course set against the classic “what gets measured get managed” which is an apocryphal quote from business theorist Peter Drucker. It may in fact be total bullshit. It may be that measurement actually hinders management. Said rather well by Simon Caulkin

Measures set up incentives that drive people’s behaviour. And woe to the organisation when that behaviour is at odds with its purpose.

Lest you worry this is just a business problem when I was single in my twenties I made a spreadsheet of the various gentlemen I was dating. I felt like I needed a way to make the process more efficient so I starting weighting categories of characteristics that was most important to me. I like intelligent men so I started listing their college degrees. I liked men who were into quantitative thinking so I started noting if they worked in banking or academics. And well you can imagine how this took a turn for the worst. Instead of meeting smart men that likes to look at the world through numbers I met a lot of bankers that went to Harvard. I was optimizing for the wrong outcome.

Next time someone tells you that some metrics or goal is the only thing that matters stop and question if it makes sense for the long term objectives. I’m not saying bankers from Harvard aren’t smart but I’m also not saying that all smart men are bankers from Harvard. And that turns out to be a pretty crucial difference.

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Categories
Finance

Day 145 and HODL

If I like something I want to commit. I don’t get folks who get panicked at bumps in the road. Hype cycles for cryptocurrency trading have been unappealing to me. I’ve never been one to watch things like FOREX trades so why would I want to do it but with Bitcoin? Like I have fantasies about being a trader but I am absolutely not. If I believe in an opportunity I am not a short term thinker or investor. I want to see where it goes.

The real excitement to me in crypto is the potential to impact larger more broad based systems. Changes that occur over time and with significant collaboration are more interesting than any narrative blip. A libertarian monetary policy implications was obviously particularly exciting. As business person the potential to change the middle man fee structure that makes financialization and banking a scourge was equally appealing. As a technologist the possibility of building applications on an entire new protocol is enticing.

The bigger picture is the only thing that matters. Go in the right direction over time and ignore the noise. That’s why we’ve slowly moved up our allocation into Bitcoin over the years. And that’s why I’m excited for my husband Alex to be working as the new COO for Hiro.

Any angle you take on the big picture implications for building new systems is an opportunity for innovation and wealth creation. That’s why I’m HODL. HODL is a mindset. Sure it came out of a misspelling of “hold” when someone was drunk but who can’t relate to the desire to really commit to a bigger vision? Participation in the creation of something bigger is the ultimate HODL value. Hold on for dear life or just hold on. Either way you are in for the long haul.

Categories
Chronic Disease Politics

Day 142 and Optimism

The pandemic has done more to improve my life than to it has hurt it. I have a little survivors guilt as I am not far from family and friends that have suffered but I was lucky. Part of my luck has been tied to my privileged place in society. I was able to enjoy housing flexibility and leave behind an expensive city apartment for a townhouse in my hometown. I was always able to work from home with little fear my income would be impacted by disease or even negative secondary effects. Nevertheless I haven’t felt much optimism until recently.

Part of my lack of optimism has been tied to my health challenges. It’s been two years of working to get a diagnosis, stabilize my spine, and get the secondary symptoms controlled. There were low points when drug regimens didn’t work. Or when it seemed like the fatigue or pain would keep my life away even when primary concerns were improving. I was genuinely terrified going into the pandemic as it did cut off my access to typical doctors visits and more hospital setting delivered care.

But I’ve found significant improvement over the past six months thanks to excellent remote care I was able to receive from functional medicine doctors. It’s almost as if with the operational and physical logistics of care removed the actual outcome of my care improved. I was able to get to the heart of a diagnosis and hone in on effective treatment protocols more quickly. Thanks to this improvement I’ve come to find my optimism again.

Not that I think the world is getting better. If anything I’m far more worried about the many axis of American failure. Our politics has become authoritarian. Our economy increasingly serves only the entrenched and already wealthy. Our interest in mitigating climate change remains low. It’s so bad the best we can do is chuckle at why millennials don’t have kids. It’s because they are selfish right? Nothing to do with how hard it is to trust that the system will ever work for you so why bother investing in the future?

But I am intrigued by the opportunities afforded by the chaos. There is money to be made adjusting us to new realities. Maybe by dint of accidental or unexpected changes we find innovations that change our world. Maybe those will be for the better. And maybe I can help nudge along the better outcomes. And for the first time in a while o believe my body will be up for the challenge. It’s nice to be optimistic.

Categories
Finance Politics

Day 141 and Double Indignity

I’ve always been interested macroeconomics. Even as a child I got very excited about trading and markets eating up movies & books with political themes. Precocious snot that I was I quoted the Economist in my high school year book. So was primed to be interested in Bitcoin from the start. I even had a physical copy of the ur-conspiracy theory of monetary policy “Creature from Jekyll Island” in college. Yes it’s embarrassing. Point being if you are a fiat freak you probably have some opinions about the Fed, a few of which sound utterly wild.

I’d been exposed to questions about money and what drives people to build and create. I was skeptical that we could continue printing currency because I was introduced to economics through the basics. I also had an intuition that this system was making bigger winners of the already advantaged and short term interests, while taking away from long term interests who need their time & money maintain its value on the horizon. Basically I think inflammation sucks for the young. And if you are young and poor it’s a double indignity.

This is why I find Bitcoin so appealing philosophically. The idea that those already in power can inflate their interests over those who come after them offends me. Dynastic societies become ossified. I found Steven Ross’s Stone Ridge investor letter to be a particularly compelling argument for why Bitcoin is a moral good for equity.

Money is, and has always been, technology. Specifically, money is technology for making our wealth today available for consumption tomorrow. Modern Americans with a ‘What’s water?’ mindset about money – virtually all of us – assume there is a sharp line of distinction between what is money and what is not. That’s false. Instead, throughout history, various monies (note: plural) have always existed1 – simultaneously – along a continuum of soundness, subject to competitive monetary network effects. Sound money – along with language – were the first, and have forever been the most important, human networks responsible for human flourishing. Imagine life without them.

I think Americans especially the monied elite interests are simply becoming too entrenched to the detriment of freedom here but most critically around the works. We have no incentive to let the rest of the world compete so we are rigging the game in our favor. I don’t like it morally even if it benefits me personally (though arguably not as much as it does Boomers and the old). I’d rather Earth compete as one as this drives our progress. Anything less is serving a double indignity to the least privileged among us.

Categories
Finance

Day 140 and Gaming The System

I’m extremely envious of people who enjoy explicit rule based games. People who find points structures exciting have a tactical advantage in our current moment. In America financialization, the trend of financial services generating wealth instead of making goods or selling services, dominates our economy. Gamers make the best traders and bankers in post industrial capitalism because they love gaming the rules.

I’ve never been the sort to scour rules looking for exploits in individual levels. I’m a gut player that wraps their head around the basic directions of a system and moves to be aligned for final bosses or big game or infinite play. I’ve never been particularly excited about quirks, loopholes or exploits. As long as I think I have a decent overview I’ll just throw myself into gameplay with an intuition of what looks like enjoyable continuous play. I don’t need to be rewarded with discrete wins I am happy to just play and build.

I’ve got friends who relish the day to day optimization stuff. They run the gamut from professional mathematicians to gamblers and full time gamers. The thing they all have in common is a love for the individual wins. They solve problems. They will rack up wins in short games but are less motivated by building towards dominance in any given system or game over time. They respond positively to the kinds of short loops that makes level play so much fun.

I’m more of a long loop than a distinct arc player. I like mental maps and models that don’t always give an immediate or measurable reward sets but rather engaging me in nested, dependent loops that yield unexpected dynamics. While I love games that have economies that have immediate yields I’m so much more turned on by ones that have distinctive world level macroeconomic game play. Nothing gets me more invested than causality you can’t see or map immediately.

But I’m envious of people that are good gamers because they have the skills and intuition for financial games. I want to be a winner at stuff like like yield farming that mimic the kind of play to win whale games. I can defend all the kinds of games I am good and how they are worth a lot too but for the moment I’ll just let my envy sit and admire the player of games.

Categories
Finance Internet Culture

Day 136 and The Ease of Centralization

We are a few days into a news cycle where Elon Musk’s corporate socialism interests and/or environmentalism has pushed the Bitcoin discourse to a fever pitch. I don’t begrudge Elon because it’s hard out there for someone who takes government subsidies and we’ve all got to lean into our economic interests. The renewable energy credit system is a policy choice and my neoliberal friends would argue it’s a good one. It’s also one that currently pay’s Tesla’s bills.

Tesla makes most of its $ from RECs, not cars. Last year, it made $1.58bn from sales of RECs to gas-powered auto companies (which must buy to offset their CO2 emissions). Tesla has never been profitable without REC sales to bolster its auto margins.

That’s about to change. Last week, @Stellantis (i.e. PSA Group + Fiat Chrysler) told @LePoint it’ll meet carbon emission rules this year. That means it won’t need to buy RECs from $TSLA anymore.
Fiat Chrysler accounts for $2.4bn of Tesla REC sales from 2019 to date and 55% of Tesla sales since 2008.

What I think is really interesting is that Elon DOES know a lot about money, in particular the benefits of a centralized trusted player. Which he himself points out since you know PayPal. Centralization has been pretty crucial to fast efficient financialization especially in modernity. Of course that has some downsides as institutional power tends to accrete. Good and bad amirite?

The exciting thing about cryptocurrencies is that they may offer us they same scale as global institutions but without the whole plutocrats and fossilized bureaucracy part. Not that I’m advocating for Ethereum or Consyns.us but they put it well in the below quote.

Whereas our traditional financial system runs on centralized infrastructure that is managed by central authorities, institutions, and intermediaries, decentralized finance is powered by code that is running on a decentralized infrastructure

We’ve got a couple decades of experience in computing on the challenges of decentralized infrastructure. It’s not easy and it has costs. The costs are both significant in time and money but the benefits are significant as well. I personally find the argument that systems which are not centralized are less fragile and it is worth diversification into systems that are less fragile. I often chose convenience and speed but I also put significant effort into having systems that can withstand crisis and disasters as well. Security has always been about trade offs. And cryptocurrencies, especially Bitcoin, is about making some trade offs in efficiency for the sake of hardening of financial system. I’m philosophically inclined towards this. If I’m trying to solve global warming and getting to Mars I might find this less compelling as I’d rather focus on efficiency. This is also why environmentalists make great villains as they decide on that choice for you. I’m not saying Elon explicitly going for Bond villain but it’s an aesthetic.

Categories
Aesthetics Finance Internet Culture

Day 128 and Financial Aesthetics

Humans have imbued money with so much significance over the centuries that financial spaces (merchants, traders, banks, trading floors, brokers, hedge funds) show us the style of their times better than almost anywhere else. Even when power centers have shunned money directly (democracies), and sometimes even because of it, money has dictated the soft powers of perception and relevance.

This makes investigating the styles of finance particularly fun as their signifiers tend to hum with unsaid anger, greed and resentment. Sexy stuff generally as we fixate on ever finer granular details to indicate that our taste shows us to be worthy of holding power (and hopefully money).

There is a reason popular culture loves the Hollywood treatment of Wall Street. Even if some of the most iconic touchstones like American Psycho were meant as dark comedies we didn’t perceive them at way. We were supposed to laugh at the business card scene not get turned on. When Gordon Gecko bellowed “Greed is Good” we were supposed to know he was the villain. We didn’t. We don’t particularly like watching these heros get their comeuppance. Giovanni Ribisi in Boiler Room ratting out the pump and dump scheme doesn’t leave a very satisfied audience but oh how we loved the second act when the gambling prodigy finds a way to go “legitimate” and become a millionaire. Just ignore the crash at the end.

Americans in particular love to fetishize our villains. Our media is littered with anti-heroes that over time become our actual heroes. We throw jealous narratives at the preppy alpha males but love it when their power is subsumed by someone who plays their games better than them. We are riveted when a protagonist emerges that knows how to best the alphas at their own game and emerges victorious. Just be careful you don’t overplay your hand and remain a villain (sorry Martin Shkreli you deserved better) as we need you to be seen as the good guy. It’s a delicate tension.

Think poor savant Bobby Axelrod in Billions becoming the titan of industry. Sure you know he didn’t start out as a classic alpha male (that hard knock upbringing) but I doubt you could tell at the end as he styles himself in the cashmere of his former enemies. Sure now it’s a hoodie but that’s a small inversion of the original sweater. The WSJ has an extensive shoppable feature on the style of the show. Now that’s cultural relevance. Turns out we do want cosplay Carl Icahn or Bill Ackman.

I’m particularly excited about the aesthetics of the next phase of financial heroes emerging from the financialization of cryptocurrency. Scrappy upstarts that want to make a more just and free financial system free of cronyism and accessible to the entire world is a beautiful narrative arc. The chaos of outsiders making the system their own has an ending we all know. You might start out in a tee-shirt and hoodie like Axe but beware the creeping encroachment of luxury goods looking to ride on your newfound wealth.

Turning doge gains into jokey NFT art is just a hop skip and a jump away from getting subsumed into the Art Basel scene. Lest you one day turn up and wake up in a new Bugatti. And while right now it may seem funny to buy a Lamborghini remember the narrative the world wants. You may just claim the mantle of a new kind of power. Or the Feds will come for you. Have fun out there!