Categories
Internet Culture Startups

Day 282 and Stop & Go

I wasn’t born until after stagflation so I can’t tell you what America or Britain felt like in the 70’s but the chattering classes seem to enjoy bringing up the comparison. But there does seem to be a bit of “stop & go” energy in the air. Everyone is raring to go but the energy cannot quite flow freely as we smack into obstacle after obstacle. Demand is pent up but the reality of supply is uglier.

Obviously this perspective of excitement and demand is colored by working in startups where the bias is always towards the excitement of building new things. Crypto is burning with the fire of millions of zealots, all of whom are confident we are building the infrastructure for a better future. Everyone feels like it’s worth investing and higher prices are a good sign. There is more go than stop here.

Of course, I am one of those zealots. I’ve got the optimism of someone who saw how fast previous waves of web1 and web2 changed my entire world. Wealth and creativity was unleashed twice over for the elder millennials who were lucky enough to witness the dot com boom as children and the social media era as their first jobs.

There were massive crashes and financial implosions too. Stop more than go. More of us got hurt than got wealthy. But we saw the possibility even as failure engulfed most of us. So we believe we might be the lucky ones this time. That we might be the ones to win the game. “Red light, green light” seems fun if you can make up ground when everyone is running. Just don’t get hurt too bad.

I feel this energy in my own body. I am excited to push into everything. My portfolio companies are all riding high. There is no way I can do it all in any given day. So when the go energy pushes me sometimes I find myself leaning into stop and simply taking a nap in the middle of the day. It makes me a little jittery to feel the push-me-pull-me of demand grind up against the limited supply of energy and focus. I’d like to feel fully unleashed but I know somehow there are moments where it’s best to stop before I go.

Categories
Media

Day 281 and Villains

This is a post that will have spoilers about the end of the second season of Ted Lasso. Do not read any further if you have not seen it. I’ll put an extra paragraph to keep it from your eyes and we can meet again tomorrow.

SPOILERS BELOW

The first season of Ted Lasso may be one of the most perfect seasons of television ever made. It’s like being inside the best session of therapy you’ve ever had. The kind where you have a breakthrough so profound that the hurt and agony of your worst childhood trauma suddenly feels not only bearable but also the reason to fully love yourself. It’s just that good on the emotional truth scale. The warmth and safety and growth is beautiful.

But season two leans into tropes and villainy where it used to rely on nuance and kindness. Rather than feeling the pride and hope of emotional truth that has been hard gotten (the truth will set you free but first it will piss you off), we are given the obvious end of Nate betraying Ted and Rebecca by going to coach for Rupert’s new team West Ham.

Nate makes a massive accusation that Ted abandoned Nate emotionally but we are given roughly thirty seconds to wrack our brains for these betrayals before it is revealed that Nate has chosen to abandon Ted. How do we feel about this? Wouldn’t we normally explore how both people contributed to the feeling? But nope it’s send Nate right into insecure narcissistic reactivity rather than mine for the potential nuance.

We could have been given a story where we see Nate and Ted equally participating in the traumas they each carry and how it affects their relationship. Ted with his fear of abandonment brought on by his father’s suicide very well may play out that pattern of abandonment on Nate. But that’s left largely unexplored. Perhaps it could have shown us how Nate intuitively sees that because of Ted’s unresolved pain with his father, Ted in fact isn’t fully there for Nate in his new role as a surrogate father figure coach.

The struggles of a young man coping with a new position and unexpected authority granted by father figure like Ted juxtaposed against Nate’s own issue with his father who doesn’t show him respect would have been an empathetic story in the hands of this show.

There was so much fertile ground for how each character could trigger emotions in the other and for how they could own and resolve these feelings. But instead it’s straight to villain don’t pass to don’t collect 200 dollars. By the end I wasn’t even sad about the loss. I’d resigned myself to the conclusion. But they could have done so much better by everyone. Even if Nate must experience his darker impulses we would have been wiling to see the full journey of how he arrived there and the pain other’s traumas has inadvertently wrecked on Nate.

I guess I’m not sad. I’m just disappointed. And that’s how you know it really mattered to me.

Categories
Aesthetics Internet Culture

Day 280 and Scooping

I first started blogging in college because a friend of mine pointed out that I needed to own my digital identity. I had written something about designer jeans in the lesser school newspaper and another student was dunking on me in her personal blog.

Unless I acted swiftly, Google results would be tainted forever he assured me. So I started blogging. Not because I necessarily felt like I was meant to be a writer but because I didn’t want this other girl to scoop my life story. I didn’t want to get “Bad Art Friended” by letting someone else tell my story.

I’m pretty grateful to both my friend James and the “mean girl” Phoebe for launching my social media habits. Every big break I’ve ever had has come from the connections I made on the Internet. If I hadn’t been petty enough to want to own my own digital identity I might have missed out.

Rather like the “Bad Art Friend” piece where one writer uses details from another’s life for her art, whoever is able to own the narrative is the default winner. It’s not terribly fair but it could have been someone else telling my story had I not chosen to write. If the victors write history then there is an incentive to be the one whose narrative wins. And the only way to win in our social media saturated works is to be sure you’ve got the scoop on your own life.

Categories
Preparedness

Day 279 and Takeout

I’m not entirely sure when or even how it happened, but I’ve been eating nothing but takeout. I think it’s some “emotional exhalation” around food. When the pandemic first hit I was in Manhattan. As wasn’t yet clear how Covid spread, we locked down in our apartment and cooked every single meal for three straight months. Probably a record in my life for going without ready made meals. But boy did I miss takeout by the end of it.

I’m sure both facts say something about the privilege I have. I can afford to have someone prepare all of my food in restaurants. And when disaster struck I had the time and ability to stay home and cook. Most folks chose their food based on budgets, literal and time.

As I’ve been concerned about the looming supply chain crunch I now think it might be time to flex the cooking at home muscles again. Letting fresh food linger in the fridge without a plan is wasteful. Whether or not I can afford the waste isn’t the point. It’s offensive to the energy and work of the many people who put their livelihood into feeding others.

I feel this especially acutely as my milk and produce come directly from local farmers. I feel like I’m letting down Daphne if our milk isn’t turned into yogurt or ricotta (or at very least put into my morning coffee). Although I will say I have no good plans for the sheer volume of peppers and chilis my farm share produced. In Colorado it is the chili that’s the crop that goes overboard in your CSA box not zucchini or some other squash. I genuinely have no clue what to do with some of more exotic peppers so send me recipes!

Categories
Emotional Work

Day 278 and Overshooting

I have been feeling terrific. That means I’ve been able to do a lot more. But it’s also one of my tendencies to overshoot my capacity. Workaholism, like any addiction, is something I’ll have for the rest of my life. Being in recovery for it means recognizing I could relapse.

I feel a bit of that overextended twitchy feeling at the moment. That jittery adrenaline fueled vibe that proceeds a crash isn’t something I’ve allowed myself to feel for several years as frankly I was worried I’d go on a bender. A bender for me is perceived as societally approved. Look at that work ethic!

So this is me recognizing that I feel like I could go over the edge and I’m not going to do it. The temptation I had to find something to prolong the adrenaline of my winning work streak is heavy. I have a number of topics I’d like to write about today. I’ve got to do lists with tempting targets. But I’m not going to overshoot. I’ve written my paragraphs. I’ll tag it. I’ll send it out into social media and then I’m going to watch some trashy tv. Hold

Categories
Aesthetics Internet Culture

Day 276 and Magical Thinking

I like to watch television to let my mind take a break. Because I spend so much of my time intaking and integrating new information for a living, I find it relaxing to have someone do that work for me. Plus I wasn’t allowed to watch TV as a kid so rebellion.

I’ve been getting served up a lot of tv shows about magic. Earlier in the year WandaVision was all about chaos magic. Then we had Loki. The algorithms then sent me to a Norwegian show about the Ragnarok. And now all I seen to find on Netflix has some kind of magic plot line. A secretly Ivy League university for magic? Check out the Magicians. Prefer Victorian era? I started with on The Irregulars. But only because I just finished Witcher as I thought I’d tried some medieval fantasy. Basically any setting you might like now has a show about magic. Outlander, Supernatural, The Order, The Umbrella Academy, Shadow and Bone are all popular right now and available to binge on Netflix.

I’m beginning to think that Harry Potter might have rotted too many brains in the millennial generation as now everyone needs stories about how they are secretly on the edges of society because of powers only a select few can ever wield. If reality is so disappointing then we need to have some other layer of existence revealed where we can thrive.

I remember being depressed when I was in 3rd grade when my mother explained to me that it was unlikely I’d ever be able to work on The Enterprise. The one TV show my parents approved of was Star Trek because I guess they wanted me to be into utopian science driven worlds. But once it was explained that this was so far in the future it’s not likely that I could be a science officer on a space ship I was sad.

Now granted I got over it and did the next best thing to living in a science fiction utopian and went to work in startups. I still feel like I get to help the future come about. But what about all these kids being raised on magic? There is no easy career alternative for the dismal prospect that you cannot manipulate physical reality with a wand or saying a spell in some elder god language.

Or maybe kids will figure out you can manifest stuff into reality. I guess the meme mobs have done weirder things like turn a washed up tv star into the president. Maybe chaos magic is real for someone. Or are least chaos is real.

Categories
Emotional Work

Day 274 and Amends

If you have ever had an addict in your life you may be familiar with 12 step work. You probably know that the first step is admitting you have a problem. As anyone in recovery can tell you, the steps don’t get any easier.

I have attended Al-Anon and ACA because I’ve had addicts affect my life and I come from a family that has suffered from the dysfunction. I’ve worked the program. It’s benefited me enormously and I recommend it anyone who has experienced the harms of addictions. Because of this experience working the program when I see others in recovery I try to remind myself that working the steps is for them. I don’t owe them anything. But I do believe in grace, forgiveness and redemption is possible.

I had a formerly very close friend reach out to me to work the 9th step recently. They wanted to make amends.

Make direct amends to such people wherever possible, except when to do so would injure them or others

The 9th step is arguably the most powerful culturally to emerge from 12 step programs. While we all know admitting you have a problem and giving yourself up to a higher power is crucial to begin your recovery, making amends is about taking responsibility for yourself. It’s a step people can rush or even avoid entirely. Amends is not about saying your sorry. Amends is about taking responsibility for what you have done so you can move forward in recovery. Only by owning your past actions with those you have harmed can you begin to forgive yourself and believe that you are worthy of sobriety. It’s not really a step about other people so much as it is showing to yourself that recovery is possible.

I was overcome with sadness when this former friend reached out to me. Their alcoholism made me feel deeply abandoned as I lost what has been a close and meaningful friendship. But I didn’t feel any anger. I didn’t particularly feel wronged. Just a deep aching sadness that my friend has been taken from me and there was nothing I could do.

There are people in my life that are in recovery that have never made amends to me. Or at least they have not formally asked to make amends as part of a program. They’ve simply slowly done the work to show me I can trust them in my life. And I’ve forgiven them. But the actual step of making amends is a meaningful one. There is a reason it’s so hard to do right.

I don’t know what the future holds for my former friend and I. The fantasy I have is that they remain sober work to rebuild the trust and friendship we once shared. I missed them terribly. I mourned their loss like a death. But this is my fantasy not reality. Reality will he more complex.

I’m sad that even having been lucky enough to receive amends from them, it doesn’t mean all is well. Our actions have consequences. That’s why the 9th step is make amends and not apologize. Amends is fundamentally about owning what you have done. So while they can now begin the process of forgiving themselves, and knowing that in good faith they did make amends to me, my journey towards regaining trust in them is just beginning.

Which means I need to be responsible for my own feelings. How will my actions to accept contact, make amends, and forgive affect me, my family and my friends? There are other people that were harmed by their alcoholism. I don’t actually know yet. The sadness is still so strong. But I do know that I will attend an Al-Anon meeting, and I will pray, and I will work the steps too. And I pray willingness will come.

Categories
Reading

Day 273 and The Newsstand

I used to travel a lot. It seems like another life, but before the pandemic airports were my most important liminal space. Even as a child this was true as my father loved taking us on trips. That emotional weight meant the airport have always had significance to me. This persistent exposure to airports lead to me to developing certain affinities and aversions in my routines around travel. But the one that I liked the most was buying something at the newsstand.

There was a period as a teenager where I thought carrying both the The Economist and Rolling Stone (neither of which I read anymore) was just the height of intellectual signaling. And no place was more crucial to signal than inside an airport. I could meet someone in passing that would change my life and they needed to see immediately that I was both smart and cultured. Yes it’s embarrassing now.

But this signaling was part of a wider ritual I felt was important to ground myself. Even if I felt the unsteadiness of traveling, I could bring routine and ritual into it. I knew no matter how much I anxiety or uncertainty I felt around a given trip I could always treat myself to buying something to read from the airport newsstand.

Generally I would pick up some kind of periodical. I’d leave myself time to browse the newsstands for at least ten minutes so I could adequately cover all the weird genres. Because I grew up in a small town and not a proper city, the only newsstand I ever encountered was at the airport. There was simply no place that held as many magazines covering as many topics.

And while I had the Internet very early in my life, the actual transition away from physical publishing wasn’t as far along. It’s not that I loved magazines so much as it was the only place I could find writing that wasn’t a novel was in newsstand. Now of course I read blogs, email newsletters, forums, Subreddits and my beloved Twitter. But the memories I have of finding new worlds came from newsstands. And while I may have literally been going someplace new, it was never quite as horizon broadening as picking out what I was going to read.

Categories
Internet Culture Reading

Day 271 and Correspondence

I love writing to others. I had some pen pals as a child but it wasn’t until as a teenager that the Internet gave me the chance to correspond with practically whomever I liked. And it’s been one of the great joys of my life to reach out to others for conversation.

I developed a habit of writing to journalists, authors and academics whose work I admired. Many of them maintained email addresses and personal websites even back before social media. If you are ever worried that someone will find it odd or unsettling to receive a note from you, don’t fret. I can share that if you are polite and sincere outreach is almost universally appreciated. Most people want to be seen. If you feel you’ve seen someone then you should share it with them. It’s a kindness to you both.

While I particularly like short form correspondence like Twitter, there is no substitute for a more in-depth and layered letter. I’m personally a fan of the threaded twenty response deep email chain. I think of it as like the letter writing of our forefathers. Maybe it’s a bit less satisfying to our heirs than discovering a box of letters but I’ve got a fantasy that the Ken Burns of the future will make excellent use of email and chat logs.

If you aren’t convinced of the benefits of reaching out through writing feel free to test it out on my before you write a letter to your favorite author or thinker. We just might become pen pals.

Categories
Finance Startups

Day 270 and The Circle of Capital

Capital has evolved a lot in my life. The dynamics have changed so much in the 30 years I’ve been ambiently around venture it’s barely the same business. And yes I mean since I was a kid. The apocryphal family history is that I was born on the poor side of Silicon Valley while my unemployed father was working on pitch deck for education software. Yeah it’s a shitty origin story but it’s mine.

Back then you sold your entire life to some dudes for half a million bucks and gave up a lot of control. It wasn’t really collaborative but it was worth it to create the future. Back then your VCs controlled a lot more than they do now for capital they deployed. Flexibility and collaboration wasn’t really considered necessary. Your VCs actually controlled when you got fired (another childhood memory was a “take your daughter to work day” where a CEO got fired), when you could raise again, if and when you could sell your company, and honestly I wouldn’t be shocked if they had some Rumplestiltskin provisions too. That’s just where the market was at the time.

As it has become clear that non-linear returns come from creative founders and new markets, the structures of capital deployment have changed a lot. Capital cares about helping operators create because creation simply has more value than it did in the past. Venture capital isn’t old dudes optimizing for control and margin anymore (even if sometimes that might be a good idea) because that’s just not what makes money anymore.

Heck it has changed a lot in just half a decade. The last time I raised venture for my own startup, we actually priced the round (no uncapped SAFEs), we had a board from day one, and we were allowed to overshoot our valuation and capital goals by a whopping 300K. I was sure we’d reached the height of founder leverage at the time. Heck I felt certain we’d raised a small fortune on favorable & flexible terms. Six years later that would be considered a charmingly small pre-seed round with very onerous terms. Time marches on! And rightly so. Markets adapt to the needs of the participants and the returns they deliver. If it wasn’t profitable it wouldn’t be so.

This is all a long winded way of saying that I am continuing the circle of life. I’ve got my own venture fund Chaotic Capital with Alex Miller and Jacob Brody. It doesn’t look anything like the funds of my childhood or even the seed stage funds of the last decade. Probably because we as founders and operators lived through the hard lessons of venture in multiple cycles and took a lot of lessons with us. Capital isn’t about control. It’s about collaboration now. Capital starts early. Capital is flexible to generate returns But we also aren’t n00bs.

Rather than spend a year raising in silence and announcing it once it’s all said and done we are building a rolling fund. That structure works for us and my general affinity for building in public. It signals founders we are building like them (even as our other constituents see it as being responsive to the demands of the market). The rolling fund is a kind of flexibility to build at the speed of the market while also understanding that the give and take of responsible deployment must also work at the pace of founders.

While we work on forming our proper fund, we’ve created an AngelList Syndicate for chaotic where we’ll be creating SPVs for our current deals (we already have our first two which feels crazy to me) as well as follow-on deals once the fund is created. If you’re an accredited investor and interested in joining our deals, head on over. Isn’t it cool how these structures morph and change over time? I guess having a couple decades of being an operator has some benefits. You’ve seen what works and hopefully have some capacity to change what needs to be changed.

Our LPs and co-investors are mostly our friends and former colleagues who have spent years working with us at companies as varied and diverse as Stack Overflow, Trello, Easypost, Triplelift, Goop, PopSugar and over 40 different angel investments. Alex Miller, Jacob Brody and I have invested over 4m over the years which seems sort of astonishing.

While we work on forming our proper fund, we’ve created an AngelList Syndicate for chaotic where we’ll be creating SPVs for our current deals (we already have our first two!) as well as follow-on deals once the fund is created. If you’re an accredited investor and interested in joining our deals, head on over.