Tag: Venture Capital

Categories
Startups

Day 250 and Getting to Know You

I don’t really like musical theater (it’s the people sorry) but I’ve been humming a tune from The King and I called “Getting to Know You” as I codify my process for meeting founders and startups. It turns out Julie Andrews through Rogers and Hammerstein lyrics may be a viable strategy for finding out if someone is a fit for Chaotic.Capital. The actual play is racist, colonial nonsense but you know take art for art’s sake.

Getting to know you

Getting to feel free and easy

When I am with you

Getting to know what to say

Haven’t you noticed

Suddenly I’m bright and breezy?

Because of all the beautiful and new

Things I’m learning about you

Day by day

She’s talking about being a teacher and getting to know her pupils but it’s also maybe about falling in love, but I like the sentiment that learning “beautiful and new” things “day by day” feels bright, breezy, free and easy. That’s a good template for relationships of all kinds.

Pitching is none of those things. It’s practiced, formal, and exhausting. It may be a necessary evil for founders as you need concise and clear communications about what you are doing and why it requires capital. But I don’t think it’s the best way to get to know people. Getting to know someone should feel easy.

I like to get to know someone over the course of conversations. My preference is through asynchronous communication mediums like chat, direct message or email. There is something about the volleying back and forth of information that helps me more. I like a back and forth that is informed by revealing thought process but also context and background. I’ll chat with virtually anyone and keep my direct messages open on Twitter because I value conversation so much.

I generally don’t feel that phone or video calls are that helpful to me in getting to know someone initially. I don’t mind short 10 minute bursts. What I do dislike is the planned hour long call for an initial conversation. Rarely am I able to be emotionally and physically present for something like that if I am not already interested or invested in story.

But if we’ve had conversations through Twitter, direct message or email where I have more context and connection then it’s possible I can be present for you. But I wouldn’t recommend asking for an hour synchronous medium as your first interaction with me. I’ll do it as a favor to someone now and again but I almost always resent it.

I’d rather get to know you over time before I’m trapped in a room for an hour to put it bluntly. I promise this is for both of our benefit. You wouldn’t take someone on a two week vacation for a second date so why would you hinge your chance to work or get investment from someone by insistence on spending an hour together right off the bat. Let it simmer a bit. Give me an appetite for wanting to help you. Then you won’t be able to get me off the phone or Signal. I will be your most available investor if you take the time to show me who you are.

So go ahead. Message me. Message a bunch. Send an email. If you don’t hear from me message some more. If I’m being evasive tell me straight me. But the end goal should be that getting to know you is free and easy. And you will be able to tell if I’m excited. Don’t give up. Just keep the conversation flowing like Julie Andrew’s did.

Categories
Emotional Work Internet Culture

Day 247 and Rooting for You

I watched a viral video of a young white American kid who claims to have quit a 100K job in order to pitch YouTube star Logan Paul for a job. It’s really hard to watch because this poor young man just utterly shits the bed on asking his favorite social celebrity to take a chance on him. He can’t even tell Logan what he is best at. He doesn’t know himself and thus cannot capitalize on his moment in the sun to show his worth. Honestly it will break your heart.

The shitty sad part of watching this kid utterly fail at self advocacy is if you are in a position of power you genuinely want to help people if they are clear about how you can do so. No one wants to say no. We all want to get to yes.

Being asked “what are you good at?” is an empathy driven open ended “get me to yes” kind of question. Logan Paul, never a celebrity I’d have previously associated with emotionally empathic, actually encourages this young fan. Even in a short clip he encourages him.

It breaks my heart a little that this kid doesn’t have anything to say for himself. Even saying something small like “ I’m the best getting groceries quickly” would have given him a chance.

I think the reason this hits me hard is that everyone has emotionally been that young man. Asked someone to help and just utterly bombed. I know I’ve taken a swing and asked powerful connected intelligent people to help me and then subsequently failed to rise to the moment. I carry those emotional failures with me. I think we all do. It’s what drives us to be better. Those moments of defeat can remake us for success. They course correct us. But only if we don’t let don’t let those failures beat us for good. We have to see the patterns that brought it into our life, accept that it’s our failure, and let it improve us.

That’s why it’s so important when you are in a position of saying no to someone to do it with as much grace as Logan Paul. I know it’s a weird sentence to type. We owe it to ourselves to there to hear them at their lowest moment with the hope may eventually become the path to their better self. Because surely someone once did that for you. That’s wisdom.

It’s hard getting a concise answer to “why you” and finding and accepting the truth of what you are truly better than anyone else is at is a lifetime of work. Being able to do it when you are young is what makes for a life that will give you satisfaction instead of disappointment.

I genuinely believe we want to help others get there. I used to hate when someone who turned down one of my pitches would say they “were rooting for me.” I thought it was dismissive. Now I choose to understand that that most people want to help you succeed.

If someone accepts time to talk to you it’s probably because human to human they would like to get to yes. I now take “we’re rooting for you” as sincere. Maybe it’s not in some cases but why not default to good intent first?

Categories
Internet Culture Reading

Day 244 and Crypto Fiction

Science fiction has often been the proving ground for reality. Without Star Trek I doubt I’d be typing this out on my own personal tricorder (mine is called an iPhone). Imagination begets reality. Much of the internet was charted in the genre of cyberpunk long before the rest of us got online.

I think we are entering a new phase with crypto and I’d like to compile a list of foundational texts that have given us the imaginative framework for concepts like the metaverse, DAOs, and smart contracts. I believe this to be a distinct genre from cyberpunk even though classics like Snowcrash transcend both genres.

For instance I don’t think Neuromancer is a crypto novel even though it is an internet novel. I’ll have to work through my logic and categorization on that front but my instinct is that novels that explore networking and computing are not in and of themselves crypto novels. They have to include some aspect of decentralization to qualify. Further aspects like self executing logic for corporations, societal organization, peer to peer and permission-less code and other similar themes I think all fall under decentralization.

Snowcrash by Neal Stephenson – the original metaverse novel. Hiro Protagonist literally inspired Stack’s Hiro. Full disclosure my husband is the COO. Ironically he has not read the book.

Rainbow’s End by Vernor Vinge – what is basically boomer has to adjust to economic life that is organized around what are functionally DAOs with the help of his granddaughter. This grossly oversimplified plot shouldn’t be used to judge the book which is actually a singularity story.

Daemon & Freedom by Daniel Suarez – the predictive text finisher for Gmail takes over the planet by creating a smart contract. If you ever wondered what would happen if what if Grammarly becomes Putin this is for you. But I do think it is an excellent exploration of how DAO (decentralized autonomous organizations) could replace the corporation.

Attack Surface by Cory Doctorow – you could include any of the books in his Homeland universe but this one pushes home a bit harder how centralized services destroy privacy which is core to why we need peer to peer permission-less systems.

Analog by Elliot Pepper – While it is technically a thriller trilogy there is an augmented persistent metaverse that is run by an organization that transcends the corporation to be something much more. Plus it has lobbyists, self destructive energy billionaire and engineer heroes.

Acellerando by Charles Stross – it starts in the home of the corporation Amsterdam and pans out from there to include things that look like smart contracts that are in fact too smart, lobsters, shell corporations, and the eventual end logic and utility issues brought on by the logic of “always be growing.” Also snag Neptune’s Brood which deals with the monetary policy implications of faster than light travel in a galactic civilization that needs slow stores of value. Cold wallets!

Categories
Internet Culture Startups

237 and Crypto-Optimism

As much as Silicon Valley and startup culture claim a kind of techno-optimism, in the wake of the social media partisanship, science skepticism and climate concerns, it feels hard to really dream big. People say catch phrases like “it’s time to build” but we all understand there are limits to the problems we solve in capitalism’s current markets. And no one believes the government can solve anything.

Any possibility or big dream can be clouded by its politics or cultural baggage if you let it. We yell about cancel culture but it’s really a lack of imagination. A kind of giving in to the boundaries of what is acceptable has captured the moment.

But I’m noticing a genuine mood of possibilities in crypto. A levity that believes in wide open horizons. Instead of the long horizon, crypto sees a bright one.

Maybe it’s because crypto’s proponents genuinely believe it will be possible to toss out legacy systems. Crypto is still so new the disillusionment of compromise to human nature, design dependencies or aggregate power seem far away. The problems that plague ant endeavor haven’t become inevitable. No wonder the mood is ebullient. We are genuinely happy in crypto.

You can imagine a world in which the DAO destroys the corporation. You can imagine a world in which artists are paid directly by patrons in effectively priced markets which respect their ownership. You can imagine expensive and exclusive financial products being automated away so even a small independent entity can access the best without bleeding out through a dozen service fees. Everything could still be a utopia.

And while I know it won’t it feels really great to be optimistic about something.

Categories
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.

Categories
Aesthetics Internet Culture Startups

Day 213 and Kobayashi Maru

I don’t believe in the no-win scenario

Captain Kirk

If you cannot win by playing by the rules, then change the rules. If you are nice Iowa farmboy named James you will probably get away with it. Or a cartoon character named Calvin with a stuffed tiger named Hobbes. There is no cheating in Calvinball because the rules are constantly changing.

I’ve been thinking a lot about shitposting this past year as it becomes a kind of social sport in venture capital and startup Twitter. I’m a big fan of the shitpost as I think making elaborate “jokes but not quite jokes” can be an exercise in vulnerability and honesty.

But who gets to be honest and what rules will be broken if the wrong person says the true thing is quite telling. I have a medical procedure that is going to take a lot out of me this week so I’ve been resting at home in preparation. This has meant I’ve watched a lot of television. I’ve been binge watching Downton Abby the period drama about Edwardian Aristocrats coping with changing social standards as modernity bears down on them. It’s a drama about “manners” which please lots of agonizing over who and what is right and proper. The class structures are so codified they are literally written down. No seriously they kept books about peerages! Check out Burke’s. Fucking wild.

It all seems a bit ludicrous as an American but I’ve got to imagine social institutions I consider completely normal will look utterly baffling in a hundred years too. And much of the way those social mores change is when someone decides that playing by the rules is a no-win scenario. Sometimes the game is so codified that no one but people who have been trained and advantaged their entire life can be winners. When that happens the only way anyone else can win is to change the rules.

Or as Spock might have said to Kirk. “You cheated.” But is it cheating when it’s a no win-scenario? If by changing the parameters the game you open up entirely new possibilities maybe it’s a good thing. Sure, Star Trek does an excellent job of showing us the emotional and moral limits of never having to face failure and it’s consequences. But what if without rejecting the premise of the Kobayashi Maru you could have never known success or change?

I think shitposting might be a bit of social Calvinball or some social media variant of the the Star Fleet ethics test. People with some power use it to great effect. But a lot of people with some talent and an eye towards improving their social position leverage shitposting. They change the rules of what can be said. They make a game of truth telling and shift the rules of the game. This isn’t a finished theory by any means but as I’m determined to slowly think my way through a grand unified theory of shitposting you can expect a lot of notes and works in progress on the topic here.

Categories
Internet Culture

Day 212 and Notes for A Unified Theory of Shitposting

Yesterday I was fucking around on Twitter, as I am prone to doing. I made a barely sit-com worthy joke about divorced guy energy.

You ever notice how women thrive in the aftermath of divorce but men implode? Why is that?

My husband Alex replied with a searing burn “don’t worry, I’ll be fine” response and we were off to the races with all our mutuals dunking. I was howling with laughter. The two of us were trading zingers and watching the DMs roll in from friends.

Obviously the undercurrent of any thread on social media got dark very fast. So quickly I ended up putting out resources for men who were struggling in the replies. The amount of pain on display was enough to make you want to donate to the first domestic abuse charity I could find.

So why is it that I can shitpost about a topic and come away unscathed, indeed it was a fun and entertaining night for both myself and Alex, but others melted down? I think it might be about class and social signaling. It takes a lot of social capital to shitpost. And those that shitpost on the most socially contentious topics are demonstrating their social capacity to discuss whatever they want without consequences. I can shitpost because I’ve got enough social capital to do so.

One theory I’ve got is that shitposting is a backlash to Ted Talks, super serious reverential coverage in glossy business magazines, and the proliferation of HBS style “business” books. We’ve had an saturation in performative professionalism.

Once it became unclear that every self seriousness biography or magazine puff piece was placed by professionals to make their clients look like geniuses (visible effort undermines certain kinds of status) the savvy social seeker knew they needed a more authentic way to telegraph in-group power. The next logical step was demonstrating that you were so smart, so powerful and so connected you didn’t even need to demonstrate it. Hence the shitpost.

The weirdest part of “shitposting” being an actual status symbol in venture capital is that a couple of billionaires are going to see me and Alex making jokes about divorced guy energy and this will only increase our status. Which is ludicrous on its face ans yet absolutely true.

This isn’t even a flex on my part (though it obviously is a flex) as it is now accepted that having a following for saying whatever you like gives you a leg up in startups. A friend likened it to “dressing down” or the practice of wearing causal clothing even in formal settings. It shows you are so powerful and wealthy you don’t need to give a fuck about manners. Shitposting on Twitter is like wearing ripped jeans at the country club.

I want to explore this topic in more depth so this post is just some sketch notes. But I wanted to get it down and organized so I hope it’s alright to have some half baked ideas. It’s my blog so I figure it’s fine b

Categories
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.

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.