Tag: Finance

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Internet Culture Politics

Day 326 and The Long Now

A culture lacking optimism is a culture without a future. Even before the pandemic, American youth had plenty of reasons to temper their optimism. Inequality, corporate dominance, rising debt particularly for school, unaffordable housing, lack of social support for family, the changing climate and the frequency of natural disasters all tend to weigh on you.

I’m a optimistic person so I always presumed I’d find a way around things. And I largely did. I got an education. I started my own company. I sold it. I found I had developed a valuable skill set. I met a man through one of my best friends and we got married. All was well in my American dream for many years.

But cracks had always been there. Little details that made me question common cultural, social and political assumptions. I discovered the limits of modern medicine with a chronic disease. I saw the disaster that financialization could wreck on families with a bankruptcy. I wasn’t naive about our systems and their inequalities.

But the knowledge that the future could be worse than today wears on you. Once you start living in a liminal state it gets worse. The pandemic made it harder for me to believe in the future because the present became a holding pattern. Ben Hunt at Epsilon Theory calls this The Long Now.

The more we put off investing in a future the more the long now stretches on. We borrow against all the things that could build us a better tomorrow. And we fall back. We put off doing things that would make our future better because it’s rational to do so. What if things get worse?

I’m tired of living in the long now. I’m investing in myself. I have been investing in my body and my health. And I’m ready to invest in a home. Not because I particularly want to own property but because I want to stop the long now and believe that my future is something I can build.

Categories
Preparedness

Day 323 and Fantasyland

I’m very open about being a prepper. I think it is a moral imperative to be resilient if you have the means to do so. When disaster strikes, which it inevitably does, being able to support yourself and your neighbors frees up first responders to care for the genuinely needy.

Because of this belief I’ve been investigating homesteading seriously for the past two years now. I’ve got concerns about the typical issues someone with exposure to finance has; worries about inflation, the social impact of labor being a poor store of value with currency debasement, & widening inequality. I am also deeply concerned about the rise in populism and the predatory graft of the far right. Add in supply chain worries and the effect of the pandemic on living standards and you can see how I’d prefer to have more control over my own basic needs.

But my plans to go off grid has always had a bit of a fantasyland element to them. While I would love to move to northern Montana and invest in a large property I didn’t expect I’d be able to do that immediately. I needed to get to know the towns, watch an illiquid market over months if not years, and also remain proximate to civilization as I still plan to maintain a career in startups and finance.

But yesterday my husband and I came across a property outside of Boulder Colorado that met many of our criteria for more prepared living. An unobtrusive property on an acre just outside of town that I jokingly called greyman as you’d never guess it was built out for resilience. It has 100% solar with insulation & a wood burning stove for backup, there is a working well that irrigates the garden & orchard, its got a hothouse & a chicken coop, it’s on a reservoir, it has a workshop & an artist studio, and well I could go on. Now I’ve got no idea if it will pass muster on an inspection but as you can see I’m already dreaming of the possibility. It’s not something I’ve absolutely got to do so we can very much walk away from a deal but I’m interested. Enough that I’m looking at mortgages and bringing in a contractor to take a look.

Now I don’t need all of those things right now. The reality of maintaining a vegetable garden and making it through a canning and preservation season isn’t lost on me. Actually building the muscles for true resilience is something that happens over years. But that’s also why I want to start now before it becomes a must have. Learning how to feed yourself when you’ve got no choice isn’t a situation I’d recommend.

We underestimate the work that goes into maintain a healthy, comfortable, warm and well fed life. Mostly because capitalism breeds specialized labor. Which is good in my book. We’ve achieved so much with it. But any complex system is less resilient. So you’ve got to acknowledge that the tail risks are there and real. So if I’ve got a chance to begin on 70% of my ideal preparation while still keeping within my budget and also staying within civilization for the time being then I’m going to consider it. It’s time to move out of fantasyland.

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Finance Preparedness Startups

Day 320 and Chaotic Families

I’m fundraising for a seed stage venture capital rolling fund chaotic.capital. Since this is a blog for my friends if you are an accredited investor I’d love for you wander on over to take a looksy. Or feel free to send me a DM on Twitter or slide into my email inbox which is julie AT chaotic dot capital. The TL:DR on the fund is that the world is getting exponentially more complex and that is making living life chaotic as fuck.

Humans don’t like chaotic. We like predictable. So we invest in seed stage technology startups that help individuals, families, organizations, and even whole communities, adapt to living with in a more chaotic world. I’m talking about all the areas we invest in on the blog. Yesterday I mused about chaotic labor markets and what kinds of companies are exciting to us there.

Today’s post is about about how families might adapt to a more chaotic world and who might capitalize on the future of adaptable families. Millenials aren’t having children. Maybe because they know our current systems aren’t set up to support working parents and their children they decided it wasn’t feasible. We need to fix this if we want to have a future.

Millennials lack the familial and community ties of previous generations and they dislike that they have been saddled with increased housing & education costs while having fewer resources to invest in having families and homes. I wouldn’t be surprised if we see a resurgence of planned communities and kibbutz style housing. HomesteadDAO or KibbutzDAO could emerge as collaborative non-corporate structures for new planned communities. Or get wild and maybe we see baby DAOs with multiple parents legally bound to one child. For all you Expanse fans I would be open to raising a Jim Holden on a Montana homestead with you. Only kinda joking.

Practically though the only way we solve for a better future for families is by giving individuals the flexibility they need across all facets of their life so we can adapt families to the future.

We need to support families where they live, where they educate themselves & their children, where they source & prepare food, where they need medicine & healthcare, and even where they find partners. There is a lot more private industry and startups can to support families profitably. The more flexibility we can grant people in building their ideal family unit the better. If one variable changes then every variable changes. That’s where startups excel generally. Software can expand the set of services available to people.

Because we’ve got a social structure problem with capitalism right now. Families aren’t affordable. Maybe we see alternative housing and family structures become increasingly appealing as the nuclear family structure cannot not afford a family. We may see living arrangements that let multiple families come together to provide childcare, food, education communal support. Whatever solutions come up we need to consider them.

Or we find ways to let families come back together. Increasing rural broadband and support for remote work could allow kids to move back to their hometowns to be near parents and grandparent to give us a chance to knit back together communities and combat urban isolation. The more we can improve opportunities in rural towns where existing family lives the more opportunities we create. That means we will need to provide all the services we expect in a city but remotely. Software businesses to the rescue! Here is an incomplete and in no particular order list of startups I would consider funding.

Request for Startups.

  • School contract swaps for private schools to allow easy mid year transitions or voucher searches for public schools
  • Teacher & childcare marketplaces, swaps or even parent run DAOs (bounty for 7th grade science teacher for homesteadDAO anyone?)
  • Home care shares & swaps or marketplaces (elder & children)
  • Remote healthcare providers & their tech stack particular support for specialties, pharmacy & data products
  • Fractional housing, co housing & house shares or other communal living for families
  • HomesteadDAO, KibbutzDAO, TownDAOs, Mobile & Van Life DAOs
  • Rural broadband services
  • Direct to consumer farm access to enable food supply outside of supermarkets & hubs
  • Any & all remote work & collaboration SaaS products & training to move more jobs out of urban hubs.
  • Fertility or birthing DAOs and co-parenting legal constructs for multiple parents
Categories
Finance Internet Culture Startups

Day 315 and Probably Nothing

The aesthetics of most crypto backlashes feel easy to dismiss if you have bought into the optimism that web3 might release the stranglehold of the Big Tech monopolies. Bomers & losers griping are just copium right?

Bitching about scams and grifters is fair. But every leap the tech industry has ever had has come with it’s share of idiotic opportunists. They usually get wiped out out. Well except the accidental millionaires. You kind of have to learn to live with that. Plenty of underserving fucknuts will be richer than you. NFT parties in New York isn’t inherently stupider than Comdex. Life is unfair. And yes it sucks. Go to therapy.

The reflexive criticism of crypto tends to break into more nuance when it goes from “but scammers” to “but utility!” But no one thought Twitter would be useful either and most of my social and actual capital has been derived from social media. The downside of web2 is that only a small portion of people benefited. And it’s true that the rewards weren’t terribly even. The accumulation of power and capital has been disastrous. But that should be more of an incentive to push for a decentralized future not less.

I had a lot more thoughts on this topic earlier in the day and I had planned on diving deeper with citations but I’m tired so I think I’ll leave it at that. If you are angry and defensive about something new it’s worth asking yourself why it scares or upsets you. Maybe the defense mechanism is hiding something important from you.

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Finance Media Startups

Day 299 and Hiring An Assistant

I’ve been thinking it is time to hire an assistant. Obviously I need help and the job would be working with me. But I want to train up someone who would like to acquire my unique set of skills. I’d like to mentor someone up on the startup ecosystem that I’ve spent the last fifteen years working through as a founder, operator and now venture investor so they too can take advantage of the incredible network of people that are building today.

I’m looking for someone that would like to get exposure to all the areas where I have expertise. You don’t have to know or even like all areas, obviously this would depend on the candidate, but what makes me an unusual player in startup and venture land is the weird mashup of specialties. So if you want to learn:

1. Angel & seed stage investing analyst skills
2. Media & hype (call it public relations if you must)
3. How one keeps your head on straight in a discourse laden zeitgeist chaos landscape

Then you might enjoy working with me. The goal of this assistant or analyst position would be within 2 years you’d go on to do what I do somewhere else & I’ll sensei you through that journey. I am where I am because of mentors and bosses that taught me the ropes.

As I work closely with my partner and husband Alex Miller you would get exposure to the operational and logistical side of investing as well as startup operations. He’s actually my inspiration for this job. His first job out of college was for Jason Calacanis. Without him none of the other jobs and connections would have been possible. And we owe him big time as without Jason we wouldn’t have Stack Overflow in our life.

I’ve only every met one person who has my particular weird blend of growth, media and investing. I do some traditional public relations and would love to pass that on to someone that could leverage it well for their own startups. But it is entirely in service to my investing and portfolio with the occasional other favor, so it’s much more portfolio services for our investments than a PR shop. But you’d learn our portfolio from the inside out as investment decisions and then figure out how to take these seed stage companies to market with the media. Which is a pretty unique thing so not a traditional gig.

Non traditional backgrounds are awesome. No degree requirements. No credentialism or social signaling. Disabled folks welcome. I’m also disabled so we do accommodations. There is no set schedule as I don’t work one so whenever you work best is great. Any location or geography is fine. Any time zone though I work on mountain. Degen anons with anime avis welcome (encouraged as I’d like someone fluent in crypto). If you are an anon avi who wants to get into crypto investing and figure out how to work the zeitgeist for your meme magic I am here to be your mentor. And then I’m an ideal world I’d be the first check into your startup as this is about the ecosystem. So if this sounds fun slide into my DMs on Twitter and tell me what the one thing you do better than anyone else.

Categories
Emotional Work Startups

Day 296 and Under Budget

One reason I’ve been comfortable working in startups my whole life is I’ve never been a big spender. My biggest expense is probably takeout, as I find cooking to be a waste of time. As long as I can afford medical insurance (I’d get a job somewhere with socialized medicine if it came to that) I’m pretty happy with a one bedroom and Chipotle for dinner. Some people get used to their lifestyle as they make more money. I just haven’t yet.

If I go bankrupt (and sadly I lived through that emotional roller coaster as a teenager with my family) I could find a way to live within new means again. I don’t have to be in the top 10% to have a good life. I only need that for health care costs and sorry America but there are other options. I’ve got skills that could earn me stability if I wanted to make that choice. Hear that Canada I’m recruitable!

But I do need to learn to live comfortably with my current means. It’s alright to live within your budget. Sometimes budgets bigger and you can easily spend more on disposable income. And this was a year where my means finally got comfortable. And I’m still sort of afraid to use it. I had to really talk myself into a chair that that was functionally a workplace accommodation. Instead of just jumping at a chair that lets me work comfortably for longer hours I spent several years just not working as many hours.

This tendency to live under budget comes everywhere. I wanted something I considered fairly lavish for dinner. But I thought how ridiculous to spend an extra $15 on dinner. I got a little worked up trying to think of other options that I wanted as much and my husband said “fifteen bucks isn’t going to make a difference get the damn thing.” And so I did and it was fantastic. I’m super happy about my evening and the spending will have no impact on my total budget. Anyone who tells you that money or privilege can’t buy you happiness are lying. Happiness is a choice and it’s an easier choice when you can make the choices you want.

I had mental upper bounds on what I think it is responsible to spend for years. I ran an Airbnb side hustle out of an underpriced two bedroom in Chintatown while I had a six figure salary, because I wanted to live so far under my means I could take risks if I wanted. That under budget mentality let me save up 70,000. It’s also how I met my husband but that’s a different story.

That kind of thinking let me enjoy startup failures for the priceless learning that they are. But now I realize I’m afraid to live on my budget. Unless I’m living massively under budget I’m a little uncomfortable. So I’m going to try to let that one go. I can just live on budget.

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
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
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
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.