Tag: Startups

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Emotional Work Startups

Day 230 and Punishment

I wish I understood why we feel the need to punish ourselves sometimes. What is it about human nature that makes us abuse ourselves? Oh we deserve it. It apparently has a social purpose as well according to Psychology Today

Self-punishment tends to serve a dual purpose as it not only relieves internal feelings of guilt but impacts how others perceive us as well.

I’ve been feeling guilty. This month is the two year anniversary of me selling my last company Stowaway to a private equity firm and pursuing a medical leave to diagnose and treat my spinal condition ankylosing spondylitis. It was a happy ending, at least mostly, with the company being put into better hands than mine. But I still felt guilty.

I felt bad I didn’t live up the expectations of our biggest dreams. I felt guilty I didn’t 100x the capital for my venture investors. I felt guilty that my colleagues had dedicated so much to me and I had failed to deliver on the outcome we had dreamed of in our early days.

So punishing myself seemed like the right thing to do. I deserved to be sick. I deserve to be in pain. I deserved for the whole world to read about my experience and my failures. I deserved to be shown in public as a weak sick woman. It sounds so abusive when I write it out. Like I thought I deserved to be tortured. But maybe that’s exactly what I felt.

I am trying to unearth why I have the self limiting belief that punishment is what I deserve. As it’s more than just the circumstance of selling a startup and not seeing the results I wanted. It’s got to be deeper than the rationalizations I’ve given.

I’ve practice family systems therapy. The basic premise is that our childhood informs how we react as adults. And by healing the rough patch’s or even traumas of those times we can live the life we choose. For me I felt abandoned as a child. I wanted my father in particular to be emotionally available. But it just wasn’t to be. But I held on to the idea that I must have deserved to be abandoned. But of course it had nothing to do with what I did or did not deserve. It wasn’t about me at all.

Now I remember that I am a capable, brilliant and above all reliable person who needs to accept what I can be and not be bound by what I learned in failure. Finding that and turning it into your superpower is where the real success comes from.

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Finance Internet Culture Media Politics

Day 219 and Crypto’s Publicist

Most industries have interest groups. Publicists, lobbyists, and spokespeople weave together stories, talking points and preferred legislative agendas. Anyone or any group is free to discuss why their preferred business or issue is worthwhile and convince others of their view. We have a marketplace of ideas. Sure, not all interests are good but anyone is free to promote what they believe in. So why aren’t we doing anything for our cause in the crypto community? I say it’s time crypto had a publicist.

Not every country allows for this. The crypto community has an obligation to recognize that when we fight for our own interests it isn’t just we who benefit. The entire world benefits from open, decentralized and permission-less systems. What we do benefits everyone who wants to live in a freer world. It’s time crypto had our own activist DAO to protect and promote our values.

I am proposing the formation of an activist DAO promoting the use of crypto. Our goal is to advocate for positive popular culture narratives about crypto. We vote on our issues, stories and key initiatives through the DAO’s native governance tokens. The DAO will hire publicists and communication professionals to promote our stories in mainstream media along with commissioning content meme-ers and creators to share opinions. Policy is crucial but public perception is faster and pushes the right policy down the right.

As place holder I’ve purchased CryptoCommsCoalition.org. The Crypto Communication Coalition. I am working on a shared collaboration doc in Google Sheets to collect input, feedback, and priorities. Anyone who is interested can participate in our effort. Email me Julie @ crypto comms coalition dot org or DM me on Twitter.

We need DAO creation specialists, legal experts, memers, streamers, Reddidters, governance folks, publicists, lobbyists, fundraisers and a thousand other specialists I haven’t thought of yet. This won’t be easy but it’s an eating our own dog food moment for crypto. We can use our own tools to advocate in a participatory, transparent and open way for our own interests. If banking and big oil can can afford publicists then so can we. gmi.

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Biohacking Emotional Work

Day 215 and Leisure

I’ve got a bad relationship with work. Since I was a teenager I’ve been compulsive about the idea of hard work. I don’t know how I got to have a problem with the Protestant Work Ethic but it seems likely I developed it long before I read Max Weber and found it’s comforting rationalizations about work’s inherent morality.

I’m fascinated by things like commodity aesthetics, the history of consumption, and theories of leisure & status. Partially because I got a kick out of supposing I was a better person than those wretched lazy types. I wasn’t so sophisticated to sneer “rentier” class as kid but I was well on my way to veneration of hard work and productive capital. An economics degree finished the job.

This was compounded by growing up in a family that worshipped the culture of Silicon Valley. The innovation of computers and the people that worked all hours to bring their creativity to the world were the most important people on the planet. They hadn’t quite crossed the cultural rubicon of power that the tech industry has now, but the power of making the future was hard work and heady stuff even before it captured the mainstream. I wanted to change the world like the people my father admired

There was a time when computing and automation raised questions of a new era of leisure. If we could move all of the work we’d previously done manually to automated systems perhaps humans could ascend to The Culture of Ian M Bank’s novels. In a distant future of abundance, sentient AIs run industry and production, so humanity can do, well, whatever it likes.

But we haven’t achieved a post scarcity world. If anything accumulating resources and showing you’ve done it by the rules of the meritocracy makes hard work even more crucial. You’ve got to play and win two games. You’ve got to make the money and show you’ve demonstrated the proper status while doing it. It seems like leisure is losing the battle quite soundly.

I’ve been pushing all year to get back to hard work. I’ve worked hard at my health. I’ve committed myself to biohacking. But really what if the obsession with working myself to the bone is killing me? I’ve been completely relaxed as I prepared for a medical procedure this week. I’ve never felt better. Which forced me to ask myself if maybe I better come to live leisure like the way I have loved work. It might be a much better life for me. The future sentient AIs might approve as well.

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Startups

Day 203 and Living Rent Free in Our Heads

There are two kinds of startup teams. The ones that forgive each other, and the ones that don’t. If you are very lucky, everyone forgives each other in time. But for the ones that can’t forgive each other, the pain of the experience is a curse. Your failures and weaknesses live in each others’ heads rent free. And that sucks.

I understand how the curse of the unforgivable startup sins get cast. I understand the pain of having people in your life that you cannot imagine forgiving because their sins against you feel too big. Startups are exactly the kind of place where forgiving seems impossible. Why? Building something new is painful.

New life, new business, new art. It hurts to birth something from nothing. Those laws of thermodynamics seem to indicate that energy doesn’t get made or lost, so sure, getting an idea to come into reality has to have an energy cost that comes from somewhere. I’d argue with startups it comes from our will. Maybe our soul. If you aren’t into that then money and time. It has a cost is what I’m saying and we pay it. And when we feel we’ve paid those costs unfairly it’s hard to forgive those whom we blame.

When you’ve given so much of yourself to make a new reality, the pain of it not succeeding is real. It hurts to realize we’ve failed. To come headfirst at the possibility that your sacrifice was for nothing is existential. That the energy you took to build something was for nothing.

With existential problems you’ve got two choices. Face who you are and your part in it or blame it on someone else. It is a lot harder to own existential yourself. If we are feeling like a victim there are people who we can blame. We hired wrong. We had cofounder issues. We couldn’t collaborate well. We had cultural mismatches.

There are endless reasons our failures are shared. And it’s true. Failure never has a single point. It wasn’t just you. But it’s not your cofounder or your teammates fault either. You have to forgive them. They have to forgive you. If you don’t they will live in your head rent free forever. And no one wants that. Find a way to forgive. Find a way to own your own existential failures. It’s not worth losing people over.

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Finance Startups

Day 202 and Show Me Anything

I’m lucky to see work from founders at the very earliest stages. If you have a problem you are solving for chaotic world I’m generally interested in seeing it even if it’s just in the idea phase. But you have to show me you’ve got a plan to build a product. Any product is fine. Just show me something! Show me how you have the capacity to build even if you suck at it.

Bobby Goodlatte captured some of the sentiment I feel on the subject well with this exasperated Tweet.

What’s a “builder”? Show me something. Anything. Just show me one pixel you’ve created. That’s what a builder is. That’s why PM’s don’t qualify.

Sometimes it can feel hard to build something, anything, when you are very experienced. This is a problem I’ve seen across all kinds of impressive people. Academics, government folks and higher end finance folks, former c-suite executives. They know what good looks like so anything they can physically make with their own two hands will all look like crap.

I’d even go so far as to suggest there is an inverse relationship between how much you obfuscate your lack of existing product and your credentials. There are other corollaries on that basic theme. How comprehensible your product is right now is inversely related to how extensive your service layer is at the moment.

I see a lot of brilliant, extremely credentialed people solving big problems, but because making money is important they will pitch what amount to service companies without an existing product. But they will use extensive jargon and hand waving visionary opportunities to hide the fact that there isn’t any product layer yet. Which is weird because like eventually I’ll find out right? You wouldn’t want to trick your investors on the state of play.

I’d encourage you to stop trying to hide that fact. Don’t be embarrassed that you can’t make things to your standards. None of us can. New things always look like shit. Just own up to that reality and you will find more help from folks who will want to help make it better. Stop showing me CAGR and TAM and possibilities as a way of hiding that you haven’t built a product yet. It’s ok. You don’t need to have built something great yet.

Admit it. Show me some wireframes and a roadmap. I’ll take that way more seriously. In fact, I’ll probably overweight you showing me exactly what you do have and how you plan to use funds to improve it. That’s how much startup people value just building the damn thing.

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Chronicle

Day 200 and Accomplished

When I set out to be more creative in 2021, I set a goal of writing “something” every single day. At first it was hard. I couldn’t figure out what to write, I second guessed myself a lot, and my style varied wildly depending on my focus, energy and attention. But two hundred days of consistent daily writing has yielded significant improvements.

Even within the first month I began to see signs this experiment was making me a better writer and thinker. From Day 31:

The biggest change I’m noticing is a smoother less disjointed focus in my mental processes. This mental fluidity (which requires non judgement) is slowly improving the quality of my thoughts

I’ve covered a lot of ground in 200 straight days of writing. Which isn’t surprising. Every single day I open up the WordPress mobile app and I just start. I’ve become comfortable with not having a topic or even feeling terribly inspired. I just keep writing it out and see what comes of it.

My favorite part of having two hundred different essays is how much it has cut down on me needing to repeat myself. I’ve worked up pieces on so many topics I can almost always find one that is relevant. An extremely handy trick if you have reply guys.

I thought I’d want to do a “best of” round up but I think I’m happier noticing the occasion and being pleased with the achievement. After all, if I do anything but please myself then this becomes a blog with an audience and I’m quite happy enjoying this for its own sake. So good job me!

I hope if you are considering taking on some project or fast that will take hundreds of days to see results that I can provide a little encouragement. I wasn’t even sure I’d make it a month but I just kept at it. If I can do it so can you!

Categories
Startups

Day 190 and Neutrality

One of the more influential pieces of art on my worldview is the science fiction comedy Men in Black. Yes you read that right. My philosophy is underpinned by a speech by Tommy Lee Jones.

1500 years ago everybody knew the Earth was the center of the Universe. 500 years ago everybody knew the Earth was flat and 15 minutes ago you knew people were alone on this planet. Imagine what you’ll know tomorrow

I don’t really know shit. I know enough to know I don’t know shit. My mother had a favorite bumper sticker “ask your teenager while they still know everything” which at the time as a teen I found a bit insulting and now as an adult think was quite astute. The more I know the less I know for sure.

Because I’ve slowly come to realize that knowing can be a crap shoot I keep odd company. Arguably bad company. I follow some truly outrageous people on Twitter. I follow hard right partisans and tankie left wing socialists. I follow folks with deep convictions on the irredeemable evils of technology and the most ebullient techno-optimists. It’s hard to talk me into not keeping an eye on all view points. Sure I think some folks are dead wrong but how do I know I’m not one of them?

Not knowing things for certain as saved my life. Medicine has a tendency to interpret data as absolute. Biometric markers and test results can for some doctors have as much authority as a papal decree. Anyone who has been told “well your test results are normal” while still feeling like absolute shit will know how frustrating this can be. Plenty of data points look absolutely normal before a system cascades into failure.

We don’t know as much as we need to believe we know. Our craving for certainty as humans is a significant weakness. The venture capitalist who insists that some metric will determine a crucial outcome is a favorite trope of mine. As if favorable CAC/LTV ratio functions as a warding spell or an attractive margin structure offers protection against a changing consumer preferences. Knowledge isn’t magic. Superstition can just as easily apply to P&Ls as poltergeists.

I find it best to remind myself to take a neutral when approaching entrepreneurs. Maybe I don’t know. Maybe everything I’ve ever known was particular to my circumstances, bias, education quirks or just plain randomness. Maybe one small insight will shift the grounds underneath me and reveal entirely new frameworks for interpreting reality. The unknown unknowns have a habit of springing themselves when you least expect.

It’s often tempting to throw opposing viewpoints into buckets that are easy to dismiss. Venture investors are notorious for this. We dismiss folks for any error we spot. We deride their data. We applaud ourselves for spotting cracks in their plans. Resist this tendency. We must always retain the neutrality of perspective that allows us to change our mental models. What we know to be true might be a lie. We may lack a key piece of context that would unlock a cascade of understanding that changes our entire perspective.

This is why the adage “strong beliefs weakly held” can be so key to success. Changing our minds is a strength. It’s hard to admit to ourselves we’ve gotten something wrong especially if we sunk a lot of time, money and reputation into it. But would you rather be right or successful? Feeling superior can be a delight but not if it gets in the way of what we want in life.

Categories
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.

Categories
Finance Startups

Day 181 and Thesis Trends

As I was putting down scratch notes for Chaotic.Capital’s thesis yesterday on the types of businesses we like I thought I’d do a bit more stream of consciousness writing to discuss some of the mega-trends that I see driving returns over the next decade.

Embedded Functionality

We think more and more businesses will be born of the embedded functionality inside protocol layers or data sets. Many protocols have functionality embedded across different layers of utility and functionality. For instance, the new consumer bank is an API at heart. The protocol layer is the API and the embedded functionality is the financial services layers enabled through the protocol or application layer. Need another example. Retail sales data and demand trends give rise to fashion retailers. Think of StitchFix, the clothing brand is the embedded functionality of its aggregate trend, recommendation and demand data set.


Unbundling Trust

Trust based networks rule businesses like insurance, retail banking, law and financing. But what if trust was unbundled from institutional nexuses of power. What if we built trust from value creation instead of value extraction. DeFi wants to build permission-less trust based on a protocol. Its entirely possible we bundle trust back into the wisdom of crowds and markets. Wall Street Bets is an aggregate source of unbundled trust. Figuring out what layers can be stripped away for more efficiency and what layers we need for safety and peace of mind are unsolved problems.


Data Ingestion Is Value Creation. The more capacity we have for data collection the more demand we will have for data ingestion and processing. While we can say sure businesses rely on the protocol and data and that unbundles trust, that’s not the full picture. We will need people who make sense of the chaos for the muggles. Ordered systems give the impression of serendipity for their users (an introduction on a social network, a recommendation for a loan, an outfit customized for you) but the work required to intake and order the data to create value for users is a big hairy problem. And there is a lot money to be made in those. Centralization may come at this layer especially in user experience.

Flexible Asset Weighting.

We are also interested in businesses that know where they stand with capital needs for their business. If you are executional business you need a thin layer of assets to succeed. To quote Roy Bahat “hot swap” startups are executional businesses. A slim horizontal physical layer to take advantage of low financing costs means return on equity is greater for these asset light businesses. If it’s deep innovation then you can be asset heavy. We like those just fine too. But knowing where you stand and anchoring your business case on your asset weighting can give you an edge. That lets you be capabilities based and find opportunities, particularly as debt as is in a commoditization cycle.


All of this is to say we are thinking across a number of system level problems to unearth startups that will give flexibility to individuals, organizations, industries and hopefully the entire economy. Incumbents won’t see who is coming to beat them because they won’t recognize the new predators. They prioritize value systems that at won’t remain true as systemic chaos erodes inefficient businesses and institutions.

Categories
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.