Tag: Startups

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Aesthetics Internet Culture Media

Day 251 or NYFW SS08

Today is Star Trek day. The original series debuted 55 years ago. I was searching for a photo of myself as a child wearing a captain’s uniform to commemorate it and instead stumbled upon a file containing my old WordPress blog. So rather than find an adorable picture of me in a red jumpsuit I found this picture from September 10th 2007 waiting for the Marc Jacob’s fashion show.

Several invitations to Marc Jacob’s fashion show for his spring 2008 collection seen from above. A blackberry, an iPhone & a recorder are scattered between wine glasses, a carton of cigarettes and two arms.

I used to be a fashion blogger you see. I have a few dubious CV distinctions, one of which is being the first person to live blog fashion week (at least according to Women’s Wear Daily). In the late aughts just before the Great Recession, it was a hell of a time to work in fashion and I wanted in. Being utterly unqualified I did what any kid would do and started a new media company. It went pretty well, we turned it into an ad tech company, sold it, and survived “RIP good times” but before all of that I partied professionally. A lot of business in fashion used to get done over drinks in fancy hotel lobbies while we all clutched our Blackberries.

This particular photo represents a time when Condé Nast still mattered. I was at the Mercer Hotel with my friend Lauren Goldstein Crowe (also apparently economic writer Felix Solomon). My friend Lauren was the newly installed fashion columnist for the new glossy magazine about money called Portfolio Magazine. We were killing time in the then trendy Soho hotel before the always reliably two hours late Marc Jacob’s show.

I don’t actually remember if I legitimately had an invitation or if I snuck in with Lauren that season. Back in 2007, if you can believe it, social media was considered very uncouth and no one has begun writing “bloggers are taking over the front row” thought pieces yet. Could have gone either way.

Portfolio was the last hurrah of the print behemoths, a glossy magazine dedicated to the culture of finance, so naturally I was appreciative that I could tag along with my much better financed friend. Condé Nast reported spent 100m on the magazine and I appreciate that some small portion of that went to drinks before the fashion of the season. Lauren is an especially erudite editor, of the sort who writes deeply studied long form work, so the fact that Condé Nast was paying to send her to fashion week was pretty decadent. She wasn’t a mid tier market editor who needed to see the clothes. She covers culture so the entire milieu was her domain. The gossip before the shows absolutely counted.

Of course, the business of media couldn’t support that sort of thing forever with changing advertising models and Condé Nast didn’t really keep up with the times. It’s a real loss. People like me ended up winning and it’s been perhaps a net loss for some things that were valuable cultural artifacts.

I spent no more than a couple grand getting our rinky dink operation up and running. We still managed to publish faster than anyone else. I had several meltdowns in service of that effort. In hindsight it was probably a waste but it felt so very new and urgent to be publishing things at the very second a look went down the runway. Now fashion week is an exercise in instant publishing and live-streaming everything from a million perspectives. But the actual studied writers don’t get expense accounts and drivers and corporate Blackberries anymore. If they are lucky maybe they have a blog with a subscription. Lauren knew it even then. She and I slowly occupied the same basic space in the ecosystem. She was just 15 years ahead of seeing it.

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
Startups

Day 243 and Delegation

One of the funniest aspects of hustle culture was its insistence on always being “on!” This maxim fought mightily against that other successful management truism; a successful CEO delegates. But how can you always be working if you have also successfully delegated your workload to a top notch team? Which one is it guys?!?!

I guess the logic was that you should always be working on whatever new horizon you has discovered in your perch as visionary founder but also be continually recruiting the best possible people to take on work as you should never be doing that work yourself. But those two directions are in obvious tension.

I think this tension ended up creating founders who exercise control of their anxiety through constantly searching for new ways to show off they were hard at work. We got addicted to busywork. Or at least the appearance of always being hard at work finding a new problem and then hiring talent to own it.

You’d always be finding new blockers at every turn, justifying it as growth and then you’d balloon your team hiring people for the work that you’d just found. I honestly wouldn’t be shocked if this was the driving force behind the trend of showing off your headcount growth.

“Oh we hired 50 people this quarter!” Sure but like were you actually blitzscaling or were you caught in the hustle/delegate hamster wheel? How many of those people actually materially moved your roadmap forward? I would bet at least some of them were just there to give you the emotional safety of claiming to yourself that you’d satisfied both hustle and delegation culture.

Categories
Finance Startups

238 and DAO Ethics

Are smart contracts freeing us from the tyranny of the legal class just to toss us into the maws of the developer class? Sure we think of lawyers as being inherently worse because they are bourgeois and protected by credentialism and regulatory capture.

But as crypto gets more complex and smart contracts involve more intricate provisioning ,will it become just as exclusionary as the ecosystem of white shoe magic circle legalese? It’s getting to be mighty hard to afford Solidity developers!

Sure we tend to think of developers as friendly self trained indie types. Anyone can learn to code! Let us not lean on heavily on the benefits of decentralization as a panacea for human nature. Power aggregates and money likes influence.

When describing the benefits of how DAOs will outflank traditional corporate governance structures we need to look out for how we avoid the self interest of a protected class of Mandarins forming. We need to think ahead on how to keep smart contracts legible. I don’t have any of the answers here. Governance is just barely coalescing in crypto but it’s never to soon to think ahead.

Categories
Internet Culture Startups

Day 236 and Founders Who Write

A heuristic I’m playing with for assessing founders is how good they are at writing.

And while this approach to vetting a founder is a practical method (everyone writes) it’s obviously limited. But I think it is nevertheless sufficient for reaching an approximation of founder capacity in a swift and asynchronous way. I like to see examples of founder writing whether it is Tweets, blog posts, technical documentation or a Notion document.

It’s my belief that we’ve overweighted salesmanship, pitching & synchronic communication methods (remember reality distortion fields) which has led to prioritizing messianic style founders. A rousing keynote speech used to be the gold standard. But this may be less relevant as teams go fully remote and more work is done asynchronously. Your capacity to document and communicate meaning at scale is crucial as a founder.

The canonical example of a founder who telegraphed competence and meaning through writing was Joel Spolsky. The Joel on Software blog established him as ur technical writer and gave us documentation culture which blossomed in Stack Overflow.

A more recent example for me is Devin Finzer who I discovered through his technical writing. Long before OpenSea was a clear winner in the NFT space, Devin’s writing caught my attention as his crisp clear articulation on the basics non-fungible tokens was legible to everyone.

My guess is this heuristic of focusing on writing instead of showmanship will improve overall diversity of founders & companies in a portfolio as less bias creeps into asynchronous documentation whereas mirroring & social cues easily tilt pitching in favor of certain classes of people

I’m also keen on folks who like messaging culture. Being able to hop in and out of conversations is crucial to team building & scaling. Those that are happy to DM & chat to build rapport in distributed fashion more easily will succeed at building relationships in a remote first world.

Categories
Internet Culture Politics Startups

Day 232 and Human Being & Citizen

There is a famous line from Plato’s Apology that sums up the central dilemma of human organization. It’s also the title of my favorite college course at UChicago.

Who is a knower of such excellence, that of human being and citizen

Socrates asks us to consider how an individual’s highest calling conflicts with the group. We actually haven’t made a ton of progress on resolving the issue since antiquity.

I’ve been watching crypto struggling with the Human Being and Citizen Problem as governance in decentralized systems because a pressing issue. Much of crypto doesn’t really have philosopher kings, despite startup land’s affection for the willpower driven CEO, because a lot still happens in the commons. Open source and all.

I’ll be curious how we proceed and resolve these issues of individual versus group intensives as DAOs get explored. The corporation with its board and executive structure is being pushed back. But we haven’t figured out how to coordinate yet.

Vitalik has been exploring moving beyond coin voting for decentralized projects in recent posts. The incentives for public goods has generally been economic in the crypto space. We coordinate on commons by being driven by selfish incentives.

Gitcoin is working through shared governance structures beyond itself with a DAO of DAO concept emerging out of Kevin Owoki’s Egregore metaphor. Though I’d personally avoid using occult old Enochian terminology (egregore is a shared manifestation come from the minds of multiple people) as no one wants to accidentally manifest an elder god

Speaking of elder gods, we are all fighting Moloch the god of coordination failure. In popular imagination Moloch is usually defeated by a world historical great man. We love the great man theory of history. One visionary dude leader slays Moloch. Humanity gets coordinated! Hooray! Historians generally agree that great man theory is too simplistic. So however these problems get solved it’s probably not going to be one great savior.

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
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.

Categories
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.