Tag: Silicon Valley

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Startups

Day 182 and Operating Capital

Popular culture portrays Silicon Valley and the startup space as one where capital is king. But it’s not the kind of capital you might be envisioning. Money (literal capital) is less of a driver of success than your social capital. And a specific type of social capital is overlooked.

The people with the most social capital aren’t necessarily founders or venture capitalists. It’s the career startup operator that has a good reputation that matters. They have a type of social capital I call operating capital.

There is a reason the team slide matters in a pitch. Who you know and how much they like, respect and trust you has a lot more to do with what deals get done. Part of this is related to luck and timing. The most talented people aren’t always the ones that have big hits. In fact, we correlate failure more strongly to overall credibility.

This makes spotting who has the most status in startups tricky. In industries like finance, money keeps the score. In consumer packaged goods, it’s what brand team you were on. In startups, the score is tricky to quantify value. We’ve developed an elaborate system of social capital signaling that determines who is considered valuable. But within that social capital status in-group you will find that the executive team layer has some of the most pull as founders and board members build working trust with them over years.

Because we value operators as high social status individuals we build our social status signifiers around your proven capacity to problem solve. How you solve problems can make or break a startup.

And we need all kinds of thinking. We need system thinking, (ops), a knack for keeping talent motivated HR), an ability to drive excitement and warp reality (marketing and PR) and obviously you have to be able to make shit (product and engineering). The people with these capabilities are the ones that accrue the most operating capital. Find those high status people and you will never be far from a startup that may have a shot at the big time.

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Finance Startups

Day 180 and Thesis

As I see more pitches and work with more entrepreneurs I am finding it helpful to have my thoughts codified on paper. That way if you are interested in working with me you have a chance to vet me. Knowing what I want to see in a deal and what just isn’t a fit saves entrepreneurs time. So I’m going to doodle a bit on what I do and don’t like.

Chaotic.Capital has 4 key investment areas. But they are really just different levels of working with an uncertain future: at the individual level, the organization level, the systems level and the planetary level.

  • Personal Flexibility is critical when it’s harder to make long term lifestyle decisions (housing, health, children) – how do we allow people to make those decisions without anchoring themselves to place or time horizons that limit optionality. Businesses like marketplaces, preparedness, personal safety, service & product exchanges, health tech, longevity, and alternative credentials.
  • Organizational Agility is a differentiator for businesses in rapidly changing landscapes, so we invest in software and tooling that provides leverage for small teams to have a bigger impact or bigger teams to act more discretely and independently. Businesses like software as a service, cloud infrastructure, collaboration & coordination software, DAOS (decentralized autonomous organizations), automation software, and memetic and organizational aids.
  • Systemic Arbitrage opportunities are even greater in chaos. Working through systems level chaos helps individual and organizations protect against cascade and systemic collapse risk, mitigate political chaos, regulatory uncertainty, memetic crowd and mob behaviors, or medical chaos, just to name a few. Businesses like intelligence, decentralized finance tooling and exchanges, cryptocurrencies, bots & analytics.
  • Climate or planetary risk is an existential risk that is already fucking with our world – we like companies mitigate the chaos of climate change while profiting on the risk. Businesses like mobility, insurance, green tech.

What I don’t like to hear are pitches for things that are tangentially related or a forced connection. Sometimes folks will try to get us excited about a problem they’ve already solved and are scaling but we are looking for longer time horizons. There are plenty of amazing startups that have great returns but aren’t a fit for us. We really do want the crazy weird stuff that is going to take a while.

We don’t need you to know where you are going. We want to see ten or twenty year out timelines. What would life look like without school? How about a world where we didn’t pay taxes based on our geographic location. How about a world where we automate how our attention is allocated. Or a world where our financial power isn’t rooted through centralized trusted powers. We want 1000x leverage on change.

I’ll write more later this week about the types of companies I don’t want to invest in. Not because I don’t like them but because they just don’t match what this fund is meant to do.

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Emotional Work Startups

Day 166 and Safe Advice

Mistakes are expensive in the moment but priceless long term. This is why failed founders are so respected and sought after in the startup ecosystem. Their advice is the best money cannot buy. Money literally cannot buy the experience that comes from having utterly fucked yourself.

Sure maybe you lost a couple million bucks but you will never make the same mistake again. And because it hurts so god damn bad you will go out of your way to help others to avoid your fate. I’ve found that founders with failures are generous. They have seen the ways even the best laid plans can implode and want to help you from doing the same.

This is why it’s all the more frustrating for these operators watch a startup struggle to take advice. Speaking as a founder with failures, I know when someone else is about to make the mistakes I’ve made. I feel it in my bones. But it’s not always easy to help people help themselves.

Getting someone to an emotional place where they can hear that they too are about to fuck up their professional life takes love. Psychological safety is crucial to hearing someone else.

I have a theory that it feels safer to hear a hard piece of advice when it comes from someone you know is delivering it without ego. Someone who never seems to have struggled a day in their life tends to evoke our own feelings of inadequacy. Their advice could never work for us because we aren’t as smart, rich, connected or sexy as they are. But someone with scars? Sure maybe they get why this is so hard for us.

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Startups

Day 155 and Momentum

Startups don’t really operate on logic, plans or “objectives and key results” to name and shame. Founders and executive teams get really good at planning and strategies only to have it all blow up in their faces. Generating momentum in spite of startups being incredibly resistant to planning is part of the trick.

I’ve been thinking a lot about the emotions that go into that “no plan survives contact with the enemy” reality of startup life. The past two days Alex and I have been enjoying a victory lap after the 1.8B acquisition of his former startup Stack Overflow. It’s a process of mixed emotions and shared experiences with other families that lived it with us.

But one central theme is that nothing changed in our skills, planning, insight or capabilities after we got the market validation. We didn’t suddenly get better and got rewarded overnight. Our plans got exploded like everyone else in startup land, over and over and over again. Till one day it was worth a bunch of money. Now everyone involved looks like a genius. But the reality is that the momentum of startups live a life and logic unto themselves. No one set an OKR for “billions” nor did they plan out a straight line from day 1 on acquiring customers consistently. No one planned out a ten year roadmap for creating enough value or revenue for a substantial exit. No one micromanaged shit for a decade. The momentum just worked itself out eventually.

And yes I’m using the Royal We here but mostly to make a point. Startups and their teams and the entire ecosystem around them are team efforts. Together we turn nebulously ideas into sketchy plans and eventually great things. Don’t get so wrapped up into the need to manage everything so closely.

A graph showing a bell curve distribution. The two outlier “make stuff”

The momentum of making stuff can and should eventually pull you into your goals. So don’t kid yourself all your numbers or plans do shit. Be the Jedi.

Categories
Internet Culture Startups

Day 154 and Mixed Feelings

I’ve been in a hazy “did that happen place” emotionally after the news that Stack Overflow, where my husband spent 8.5 years, sold for $1.8B. Obviously it’s a lot of money to just appear into our lives. It’s not the first exit for Alex Miller or me. I’ve had 2 acquisitions for companies I have founded & he’s had an IPO for a company he was early to join. I also lived through multiple exits, financings IPOs & bankruptcies as a kid as I’m the child of a startup family. So why does this hit different?

I think part of it is that our other wins tended to come from “faster” companies. My first acquisition came within 2 years of founding. It wasn’t a lot of money but let me pay off student debt & get more stable. Alex was with Yext for a comparably shorter period and when it IPO’d he’d long ago left for Stack Overflow. And that was only a win because he was lucky enough to be able to borrow money to exercise his Yext options or it would have meant nothing. That happens a lot to early stage employees. They cannot afford to exercise and get nothing when a big exit happens. It happened to me when the company that bought mine exited to someone even bigger. I couldn’t afford to exercise. I never had the heart to calculate how much I would have made.

We’ve had secondaries over the years. Sometimes equity gets taken off the table in later stages financings and it benefits early employees. Those changed our calculus a lot when it happened to us. We put together a financial plan and a future as a family with our startup earnings. We made decisions based on whose turn it was to risk & who to run downside. Being a startup spouse means a constantly balancing act of supporting years of low salaries, long hours and stress. And while it’s not easy to be the wife of an early stage employee it’s probably even harder to be the husband of a founder. Startup families live through a lot together.

Stack Overflow was “the” company in many ways for Alex where he spent the better part of a decade and the majority of our marriage working to build the company up. He was employee 32 when he joined as chief of staff. When he left it was over 300 employees and he was the GM of the SaaS business.

When he left Stack we didn’t expect a payday beyond what salary he had earned and perhaps a bit of secondaries. He’d done good work and built amazing things but when you leave you don’t want have the emotional capacity to think about things like big acquisitions or IPOs. When Alex left Stack it was a deeply emotional process for us. A lot of therapy for both of us. Because startups aren’t just the person it is their family that consents as well to these long journeys. Remember that every executive team member or founder has a family that will live through this startup experience too.

After 8 years I knew Alex needed a change. He had given Stack his all. His absolute best. But leaving was hard. In order to leave a company where you invested your whole self (and your family’s) you have to come to terms with how you feel. We cried. We worried. But Alex made the choice. And we didn’t look back. It’s too painful in some ways. You love your startup

You keep in touch with everyone. Alex remains friends with the entire team. We share hobbies & interests and a million group texts with topics as varied as hydroponic tomatoes m, our crypto portfolios and hunting season. We stay at each other’s homes. The bond is deep in startup teams.

Given that bond it’s almost funny how when you leave your imagination on big outcomes can stop. The thing you dedicated yourself to for years is now growing and thriving without you. It never leaves you even if you need some distance.

When we got the call the number was overwhelming. The distance we had created suddenly evaporated. Alex burst into my room where I was meditating and told me the strike pierce. We did some calculations. We checked them. It couldn’t be? It was. The startup had finally delivered the check. We’d done it. Another startup made it.

I want people to know that this kind of largess is mostly random. Everyone works hard in Silicon Valley. Startups are a choice & a state of mind and those of us that chose to do it willingly go into ideas doomed to failure. Or meant for the stars. And it can feel like a crap shoot. Idiots get enormous paydays and brilliant innovators barely make enough to scrape by. The meritocracy isn’t as real as we think. This isn’t to suggest that the Stack Overflow team doesn’t deserve every penny. They do. We earned the payout. The bad years were hard. Miserable. But everyone believed in the community & the power of software developers. But also no one earns these big paydays. It’s a gift. And we are grateful for it.

Categories
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.

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 Startups

Day 146 and Gossip

Gossip drive the world. The stories we tell about other people reflect a lot. Even if we claim we don’t care what others think what others think moves the world around us. And I would posit that this actually isn’t a bad thing. It can drive closer bonds and increased connection.

There is a concept in evolutionary psychology called indirect reciprocity. Natural selection favors strategies that base the decision to help on the reputation of the recipient. Social interactions in which one actor helps another and is then benefited by a third party are key to cooperative reputations.

This isn’t just a systemic population level issue either. People who are more helpful are more likely to receive help. It’s uneven obviously and people can obscure their reputation. Depending on if you are up or downstream of helping or being helped, you make different calculations. Some people help more but they feel it’s worth the cost. They are downstream. Others accept more help because they are upstream. We are all making trades based on our position and arguably they are fair market trades.

How we decide to cooperate and with whom is driven considerably by reputations and shared value beliefs. Relaying reputation signals to bolster your capacity to connect to others is actually a key part of empathy. We need to establish psychological safety to partner with each other. Gossip helps us find suitable relationships. This is especially true in disciplines which require creativity. Quoting myself on the topic of psychological safety in venture capital.

If entrepreneurs are solving entirely new problems with high chances of failure feeling like they can trust their financial partners should be a top priority. Yet the atmosphere of distrust is pervasive. Venture capitalist and entrepreneur are constantly managing the information flow between each other.

Managing the information flow is a key component of gossip. Showing you understand their context, their fears and their reputations concerns helps you. An act we denigrate in popular culture actually helps you to deepen the relationships as each signifier breaks down space between two people and builds trust. So don’t knock gossip. It has evolutionary, societal and individual benefit. Just remember the ultimate outcome is about bringing people closer.

Categories
Startups

Day 144 and Scars

I have significant e-commerce, direct to consumer and retail business experience. I’ve managed multi-million dollar P&Ls, worked on iconic billion dollar brands and started my own direct to consumer cosmetics line. You’d think with that experience I would be deeply bullish on my ability to pick up and coming startups in the space. But I don’t particularly want to invest in digital brands or online retail. And I think it’s scar tissue.

I’m not saying flat out“no” I won’t ever invest in a DTC business or an e-commerce startup (I have and I will again) but a little bit of knowledge can make it hard to preserve creativity and imagination. Many founders can come out of a space where they have dedicated years of their lives and simply want space away from their expertise. They know too much. They’ve seen things. The scar tissue that forms to keep you working during the long dark soul of startup pain is still tender.

When I mentioned this lingering pain others pointed me to other areas they struggled to hear pitches or invest because of experience. Rental businesses and neobanks from Maia Bittner, certain e-commerce verticals from Lee Edwards, fitness from Jason Jacobs. It’s a common phenomenon among founders.

I’ve got lots of opinions why certain kinds of businesses won’t thrive or have business models that won’t make the kind of return my own personal investing thesis demands. But the truth is that I now have enough expertise to simply know more than is good for me. Ironically this means I should spend more time as an advisor or consultant on certain kinds of businesses but it takes a special founder to coax it out of me. Because I do have valuable insights and I want to share them.

But the last thing I want to do is pass on the trauma of my own experiences. Founders deserve to have their psychological safety preserved so they can build the company of their dreams. Some painful insights from a founder that came before them might help them avoid some pitfalls, but if they take our traumas too seriously they may never find their own path. And that kind of backward looking “it will never work” or “trust me kid I’ve been around the block” attitude can really bring creativity down. So I will always share my honest experience with anyone who asks but I’m hesitant to ever let anyone take my lessons to close to heart. You very well may be the one that breaks through where no one has before.

So when someone pitches me their new retail startup or DTC brand or cosmetics concept I try to be honest that I may nit be the best fit. I’ve got scar tissue. And if a founder insists that I can help I will try. But remember not all skepticism, fear, distrust or dislike is about you. Sometimes it’s all about the trauma of having lived it before. Asking someone to live it again is the ultimate act of trust. And maybe just maybe we get to firm new scar tissue together.

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.