Finance Startups

Day 348 and Empathic Investing

The best investor I know is Cyan Banister. When I was coming up in the web2 world I got to watch how Cyan handled early stage relationships. She brought total empathy to every interaction I witnessed. The kind of candor, kindness and willingness help her founders eventually set the template for how I wanted to work. I wanted to invest with my whole self like Cyan.

While I doubt it was the primary motivation or even expected outcome, Cyan’s angel investments are some of the best returning of the generation. If you subscribe to Alex Danco’s theory of social capital and angel investing this kind of investing is playing an infinite game. It clicked for me then that the real edge you can bring to the earliest stages of startups is an open heart. An open heart gives you an open mind. And everything else is a matter of tactics from there.

Creativity comes from seeing something in a completely new light. A change in metaphor can lead to tangible physical discoveries and complete cultural revolutions. Science fiction gave us the tricoder and the internet. Imagination literally helps forge the future. So it’s important if you want to spot the catalyzing “this changed everything” moments that you be open to seeing the world in an entirely new light.

While I obviously have an investment thesis on the macro level events shaping market demands, it’s not practically nearly as helpful in the day to day of investing as just being human. Creation is volatility. It’s not usual for a founder to bounce between terror and euphoria on the same day. Imagine how exhausting that can be when your entire life is always fight or flight and fear or famine.

My only job is to show up for a founder in that moment and accept them for who they are. They need to trust me enough to tell me if they are scared. Trust me enough to share their biggest wildest dreams. It’s a delicate and intimate thing to be there for someone no matter what. But I firmly believe that is what it takes to build something worthwhile. It’s never ever clear from the outset if it will succeed. The only thing we can truly have confidence in is our ability to solve the problems along the way. Chances we’ve seen the tactical playbook and can help you solve those more easily. Many of us come with baked-in operator skills like acquisition or operations. We can teach you that.

While this may all sound utopian, or if you are a bit cynical, even maudlin I assure you this is the most competitive way you can approach investing. If capital is simply a commodity you must infuse your work with real value to compete. If you have a lot of assets under management maybe you can add a lot of services. Large prestige funds with billions in AUM can offer that. But now you have to have bigger deals and surer outcomes so that impacts what you can invest in. Scale impacts outcome in all kinds of practical ways.

If it’s all about the capital then you can be beaten not just by a better term sheet (which just makes everything you do more expensive) but also by someone who brings intangibles to their place on the cap table. You know whose pro-rata doesn’t get cut? The person who showed up day in and day out before the round got competitive and every is kissing ass to get in. The founder remembers. And so does the empathetic capital. We win twice over because our deals are cheaper and we stay in them longer.

So founders and fellow investors ask yourself who you want in your corner from the start. You may find the smartest capital is actually the nicest capital as well.

Finance Preparedness Startups

Day 320 and Chaotic Families

I’m fundraising for a seed stage venture capital rolling fund 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
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.

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.

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.

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.

Finance Startups

Day 255 and Bias Towards Fuckround

There is a tendency to believe that startups have a bias against older people. While ageism is alive and well, I’d argue what appears to be a bias against older teams is actually a bias against teams with experience. No one wants to invest in a team who don’t fuck around. We want teams that will find out.

One of the reasons I work with early stage startups is because their trajectory is not yet set. Every conversation has a hint of “fuck around and find out” because your vision is far away. You need to experiment, test, throw spaghetti against the wall. Pick your metaphor. The bias towards action and the bias for momentum exist in investor minds because the alternative is death.

This has the second order effect of selecting against teams with experience. It isn’t ageism. It is a bias against a certain kind of professional that knows too much. It’s not that anyone thinks experience is bad. It’s harder to fund teams with no exposure to the industry they are working in. It means that some types of experience will function as negative signaling. We think you know too much to solve the big problems. We are afraid you aren’t flexible enough to do the work of throwing out all existing assumptions.

While being an expert in a field means you have a better sense of how you will get from point A to B, it also means you have a less flexible mindset. You have seen what hasn’t worked. You have opinions about can or cannot be done. Even worse, you have an idea of how things must be done. Simply put a certain kind of battle tested, “expert in their field” persona isn’t trusted to fuck around enough.

If you are one of these founders, you have to fight against this signaling issue. Show investors your commitment to fucking around and finding out. Telegraph that all your experience and knowledge from your past work could very well be bullshit. Show us you will be committed to testing even more rigorously every hypothesis of how your roadmap will unfold. Then your experience becomes an asset.

We will trust that you have more opportunities to fuck around and find out than a less experienced founder because you plan to test what you think you know. Which is a lot! Show that no truism of your space will be held sacred. While a neophyte team will need to discover all the truths of a space to even begin to test. you will be ahead of them running test after test. Jujitsu that shit. Use the energy of your experience to show that you will bring the maximum amount of flexibility to finding new outcomes. The unbiased but experienced mind has the best chance at achieving momentum.

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.

Emotional Work Finance

Day 233 and 927 Hours of Therapy

I’m motivated by media. If I’m in a bad headspace I can take time to read a book or watch a tv and shake myself out of it with a few hours. I’m a voracious consumer of all forms of narrative, it’s how I synthesize.

You’d have to be a professional to keep track of more stories than I do just by sheer numbers alone. Maybe journalists, authors or publicists read more than me, but even then I’d bet real money I’m still top decile. I never lose a “Wait Wait Don’t Tell Me” news quiz.

I’m working though some emotions on risk, punishment, hurt, and fear this week. So I’ve been watching a favorite show on all those emotions: Billions. It’s a show about a hedge fund manager feuding with the US Attorney for the Southern District. It’s a terrific portrayal of finance culture and elite consumption. But it’s real strength is it’s portrayal of therapy. Emotional capacity is the key to coming out ahead in Billions.

While I don’t want to give any spoilers, the second season gives us a character named Taylor who is a prodigy. Not only are they intellectually brilliant but they understand who they are. I’m rewatching the show so I’m noticing details I didn’t process the first go around. Taylor says they have had 927 hours of therapy.

The impression I had on the show was that Taylor was in their twenties as they frame the introduction of the character around an internship and graduate school. I wish I had started on therapy in my twenties. Imagine having over three years of intensive emotional work before you’ve started your career. Honestly I’m envious. When I was in my early twenties I didn’t understand jack shit about my emotions.

Maybe by the time I get 927 hours of therapy I’ll recognize my own traumas and motivations as well as Taylor. I’m getting up there in hours and I am admittedly sinking a lot more into understanding what motivates me now than I ever did when younger. It’s not exactly linear progress. Feelings aren’t facts. That makes it a lot harder to lock down what will or won’t work for you. But I’d rather be finding out who I am now. Some people never do. But still I wish I’d had the good sense to invest 927 hours into therapy when I was Taylor’s age.


Day 225 & Explaining DAOs to Moms

My mother is a sharp woman. She’s interested in economics but if you asked her to explain securities law she’d probably shrug. Not her expertise. She did survive our family bankruptcy during the tech IPO implosion she’s got a slight intuition of securities law in the context of consumer protection but that’s about it.

So I was impressed that she was able to sum up the recent infrastructure bill’s attempt to make crypto foot the bill very neatly.

So they are trying to convince us that people who program computers to run math problems are actually bankers?

That’s…actually not too far off. She seemed to grok that this was a misunderstanding of the basic technology, who builds it and it’s purpose. She was glad the amendment didn’t pass. Clearly people who build computer applications are not the same as the guy at Charles Schwab who looks after her retirement account.

We were discussing it, as I was trying to explaining PR DAO and why I wanted to help organize an activist group of folks whose purpose was execute public relations campaigns to tell stories about crypto. I explained to her that rather than having a bunch of executives who make decisions we would write a set of rules that automatically determine how we make decisions. Those rules would let all members of the organization vote on how we wanted to deploy our assets and pursue our agenda. She liked the tag line “rules not rulers” a lot. She’s pretty into freedom. A smart contract was pretty intuitive to my mom.

Where she got confused was the governance tokens. Not how they worked. Again it was intuitive to her that depending on what you contributed and how invested you were in the organization that you would a different say in what got done. Maybe each token represents one vote. Maybe some people have more votes because they are more invested. Presumably we figure that out in our smart contract. What she didn’t get was why the government thinks a voting mechanism is a security.

“So the government treats the way your group organizes decision making as if those little voting symbols were stock in IBM? That’s fucking stupid”

Now granted my mother probably can’t explain what a security is (she’s got the basic idea that they are like a type of money and Boomers like to own stocks). She gets why they are regulated the way they are in a general sense. She’s lost money on badly governed companies. So sure it’s fine that the government has some rules for that sort of thing.

But even to a lay person like my mom it seems pretty clear that something meant to represent ownership in a money making enterprise and something meant to help organize voting and decision making are separate ideas. She seemed to think maybe they ought to distinguish between the two ideas. Because you know the last time we came up with clever ideas like the corporation the whole world changed. Evolving them again to be autonomous could make for the same level of change. If my mom got that in a half an hour phone call seems like maybe the professionals at the SEC could work it out too.