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
Preparedness

Day 277 and Supplies

I’ve been watching the supply chain cascade issues for several weeks. Ports are backed up across America, the cost of a shipping container from China has gone on average from $4000 to $19,000, and there is a national shortage of truckers to get goods moved even if they reach American shores. If you are interested in the topic and the possible impacts, my favorite site for preparedness The Prepared has a synopsis without the panic or bullshit.

I reached out to my mom suggesting to her if she had any major purchases or repairs to do so now. She’s been intending to get the shocks replaced on her husband’s truck and moved up the appointment to get it scheduled today. I went through my various preparations for emergencies and realized I was in very good shape. Maybe I could upgrade a pair of boots or consider a new winter parka to upgrade from Uniqlo to LL Bean.

But there just wasn’t much I needed to do. If we had food, fuel, or medication shortages or delays like Britain is experiencing, I am prepared for that. I’m not in a place where I can sustain a full civilization collapse (I haven’t convinced my husband to move to a homestead yet), but I’d definitely be fine if we had a month or two of cascade issues. I am thinking of scenarios like a big winter storm knocking out the power grid and impacting downstream systems like water treatment. Or I-70 gets blocked for a week or two and we have shortages at stores because truckers cannot get over the pass. I mention those two because both happened this year calendar year. These issues are it as rare as you think.

And it struck me how incredibly lucky I am that I can consider something like a supply chain crunch and rather than struggle to afford things like a car repair or a winter coat I can simply buy them. The privilege I have to be a prepper (or a doomer) is significant. And I really genuinely don’t think that should be the case.

America makes big claims to exceptionalism but we regularly have disasters that make us look like we’ve barely achieved a stable economy with functional infrastructure. So if you can prepare for a disaster please do so. The life you save may be your own. But in reality it’s probably more likely to be your neighbors. And we owe it to each other to take the strain off the system so when a disaster hits so we can do better together.

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
Finance Startups

Day 275 and Manifesting

I had a really terrific September. Everything just started going my way. Projects that I’d been pushing on had significant breakthroughs. My deals got hot. My focus and health improved. Even when I had setbacks and failures I was able to execute on quick recoveries. But mostly I didn’t give in to past bad habits. And all of that happened without any additional effort on my part.

I’ve been making a really conscious effort to stop pushing myself to always be doing more. Either I am able to find elegant solutions or I ask myself to take a step back till I can. Rather than brute forcing everything I am finding ways get where I am going without sacrificing myself to costly bad trades on my time and energy.

I asked for something really significant from one of my investments (an additional allocation for an special purpose vehicle). The second I asked for it I started to panic. I didn’t have an immediate or simple path to deliver on what I asked for from this founder. Even though I was confident I had the money for the deal it out I panicked that maybe I had bitten off more than I could chew. Immediately it started going through my head about how bad I’d feel if failed this founder. I relived the guilt, shame and punishment I had felt in previous failures to deliver for people that trusted me. I hated feeling like I’d failed people.

And I just decided stopped the cycle of worry then. Like turning off a switch. I told myself I could do it, I knew I could do it or I wouldn’t have asked, and that there was simply no way I was going to let down this founder. But this is where I felt the frown Instead of going into overdrive, I stuck by my schedule. I didn’t change anything. I didn’t push myself to a frenzy by adding in calls, pitches & emails. I just put down all the steps I could and would take to make the deal available to the right people and I began.

In the past I would have let that fear drive me. I would have gone into overwork and adding in additional tactics that I didn’t even need to insure I would reach my goal. But here I trusted myself to get the outcome. I didn’t exhaust myself. I took care of myself. And the allocation got filled quickly. I checked the commitments this morning and I’ve only got 15% of the deal left.

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
Emotional Work

Day 272 and Small Steps

I talk a lot about pacing and routines and rhythms but it’s mostly because I struggle with it so much. As soon as I notice something is going in a direction I dislike, rather than course correct a little bit, I love to run in the opposite direction as fast as I can. Why be steady when chaos begets creativity?

Silicon Valley success myths are tied heavily to people that go their own way. We’ve coined terms like contrarian and narrative violation to add a high gloss to the basic truth that we just don’t like having our hands forced. Not even by ourselves. We like being able to pick and chose our direction.

This isn’t just truth of institutions or common knowledge. I get pissed when I’m forced into something by my own body. Heck, I especially dislike having my hand forced by my own biology. There is no authority more unforgiving than my own flesh.

Which has sometimes meant if I can overcome a biological reality my ego finds painful I’m inclined to do it. I love imposing brute force on myself. Naturally this habit isn’t the sort of thing that makes for a comfortable or pleasant life. But it’s a huge comfort to know that if you simply apply a little willpower you can undo the sins you’ve spent too much time accumulating.

Just look at some of the habits that have gained popularity in startup culture from intermittent fasting to overnight work sprints. Those techniques work. Some are arguably even sustainable for people. But it’s important to remember no matter how much we like to make things happen quickly, decisively or in new directions that sometimes the reality of being human cannot be ignored. On those days remember it’s ok to take small steps.

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.

Categories
Emotional Work

Day 269 and Pacing

I’m very defensive of my time. While I work at curtailing reactivity in my emotional growth, it’s still easy for me to feel invaded by obligations to others. Taking video or meeting in person was among my least favorite activities even before the pandemic. That’s one reason I’ve written extensively on how to communicate with me asynchronously. But another deeper reason is my fear of misusing my time. And tempting as it may be to project it onto others, I know that this fear is entirely about me.

I am very fearful of anyone needing things from me. I don’t mean things like money, favors or advice; though it is harder to say no than you’d think. My fear is deeper. I’m afraid friends and family will start to count on me for their emotional needs when I’m still figuring out how to be present for my own. I’ll deliberately put distance between myself and others to avoid feeling needed.

So what does this have to do with pacing? I’m not very good at giving myself enough space to be challenged and recovery. And when every encounter with another person is an emotional challenge, I need to be careful about pacing myself.

Maybe there is some latent autistic spectrum issues or maybe I have more trauma than I can consciously dig up but it’s a rare human that doesn’t make me anxious about the energy required for maintaining my own boundaries. It’s not about other people to be clear. It’s about me and my fears of being emotionally invaded.

As I build up more systems and accommodations to allow me to work effectively I need to figure out better pacing. How do I connect with others without emotional fear while still respecting my needs for down time and rest? Giving myself enough recovery has been an ongoing challenge that I write about extensively. But putting it into writing also serves as a valuable reminder to course correct before a crisis emerges.