I had almost nothing on my calendar today I didn’t want to do. I had small administrative things that took up maybe two hours and that’s excessive by my standards. It’s rare I ever have more than half an hour of genuine obligations. Mostly I just go where I feel like on any given day. I lay in bed on my phone and I move the world with strangers on the internet.
I’m not sure how I optimized for this kind of idyllic work life. I certainly didn’t used to live this way. When I was a founder I was constantly at the mercy of meetings I didn’t want and obligations I wanted to shirk. I always felt put upon. I never felt more like hustle culture owned my life than during my founding years. I was constantly optimizing and I felt like I never had any relief.
Maybe it’s the pandemic. Once we stopped with offices and workdays and all their attendant events and activities, life got a lot better. Everyone kind of settled into routines that made space for what mattered most to them. We no longer had cocktail parties or conferences. Thought leadership stopped being keynote speeches and started being shitposts on Twitter.
I don’t know what the fuck I did it exactly to free myself from that over scheduled fate. I’m so much happier and more efficient. I get shit done and I am less stressed and working fewer unnecessary hours.
Maybe part of it is that I might be a better investor than I was a founder. I could spend the whole day skipping through direct messages and sharing insights in Telegram group chats or having product breaksdowns in Notion. I’m actually good at what I do now. I bring more value and I do it more quickly. Maybe this is what real optimized work is like. You are so good it’s easy.
I’m so fucking happy right now. Over the last hour I’ve done more to advance my deals, connect my community and dig into shit that I genuinely passionately love than I thought I could do in an week. It’s like winning the lottery. I cannot believe I make money doing this.
I basically gossip all day with super smart people and then trade a bunch of densely coded social signals. Those all translate into money. I plot elaborate stories with fellow degenerates with deep aesthetics and then we send it into media zeitgeist. It’s like I work in fashion but the pay is much much better. So I guess it is true what they say. Do what you love and you never work a day I’m your life.
One of the unexpected benefits of writing every single day has been the accumulation of reference material. I can send folks a synopsis rather than retyping a topic that I get asked about a lot. So if you want to know how I get healthy, or how I invest, or even how I think about aesthetics this page will serve as a reference for year 1.
I’ve got a friend who is a world class talent in their field. I admire what they do. But their ability is fairly is specific to what they do at a startup and doesn’t transfer easily to different stages. They recently took a job at a different stage and I’m a little afraid for them. What if it breaks them? What if they get burnout? I am projecting a lot onto this friend at the moment as I am also a fairly specific kind of talent. I’m an early stage person.
The reason I’m so sensitive is I’ve been broken by being in the wrong roles or working on the wrong problems. I tried to change myself to fit something I was only a 7 at when I knew I could be working on something where I was a 10. I hurt myself to fit in.
The hardest part about startups is they are genuinely life altering. It’s hard to make something new. Every harder to nurture and grow and sustain it. Creativity is fucking hard. Every time I criticize a project I do it with a hitch in my heart. I know even the shitty failures were the honest best work of people who cared. And often when it’s a success it’s not because any of them were better than anyone else. We are all fighting our hardest battles. Sometimes by the grace of God our work gets lucky.
So in the meantime I think we should all be having fucking fun. I only commit to founders who so clearly want to solve the problems in front of them. That passion cannot be forged. Real interest and focus are such potent forces. You feel it in your bones. Doesn’t have to be a huge world changing problem either. You can just really love your little corner of the universe.
So don’t try to fit yourself into a role for money or status. Pick a startup because it’s going to be a blast with people you love. Make sure as much of the work will be your particular brand of fun. Maybe to someone else it would be hard work. But if you pick right it will be fun even if it takes all of you to do it to the standard of your passion. And if you are very lucky sometimes it works.
Gaming is what finally pilled me on crypto. When I took a medical leave a few years ago I felt isolated. I picked up a number of social games as a way to feel connected to other people. What started as fucking off ultimately transformed my perspective on investing. I didn’t know it yet but it was setting the stage for my fascination with web3.
I made friends. Real friendships despite none of us ever spending time together IRL. I made friends all over the world in completely different places, from wildly different social and economic classes, and we all easily collaborated to win together.
And while this sounds obvious I learned just how much talent and intelligence is evenly distributed to my fellow humans. The only difference between me and many of my fellow gamers was that I was born with a good passport. While everyone had the same access to internet as me, what they didn’t have was the same access to to global markets as I did. We could play together but we couldn’t invest together.
Their ambitions were cut short because of geopolitical decisions that had nothing to do with their ability to contribute and accumulate meaningful value. I had always known this intellectually, but never before had I been so deeply emotionally connected to so much human diversity as I was through gaming online.
Frankly it radicalized the fuck out of me. People in the West have no idea how good they’ve got it. And it’s a crime that we are not all actively working for all of our species to have equal access to markets. It’s just fucking time to drop the colonialism and the exceptionalism and combine our ambitions. We’ve got big problems to solve.
For me wagmi is some powerful solidarity shit. And I’m basically a foot soldier to the plutocracy. I am at the top of the food chain. I’ve get every reason to want to rent seek and act a protectionist to preserve my place. But thanks to something so simple as playing with others got me back to the golden rule. Do unto others.
Web3 offers a radical cultural position that everyone should own their work and everyone should compete with the same rules. When we say “we are all gonna make it” it’s an optimism about the kind of future we can build together. Sure the wealth is good. We need those incentives to come together. Markets operate on self interest. So let’s use that slay the beasts of collaboration and make stuff together. Wagmi.
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.
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 chaoticworld 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
I’ll be talking about all the areas we invest I’m sure but today’s post is about about how we might adapt to a more chaoticlabor market and what kinds of companies we’d like to see in the space to capitalize on the chaos of the future of work.
The pandemic has accelerated a lot in the labor markets. Hiring in developed economies has been getting harder. The great resignation has a large chunk of the skilled workforce in movement. But student debt is making it less appealing to pursue traditional credentials like a four year college degree. Skilled workers have at once never been more competitive in the labor market but it’s also never been more expensive to pursue those skills. Where there is tension there is opportunity.
So how do we get more people skilled and let those with existing skills deploy their labor more effectively? I think that web3, or if you prefer the decentralized web, presents a unique opportunity to decouple skills & compensation from identity and corporations. Flexibility drives innovation. Web3 let’s us step clear of concepts like one full time job per person.
Workers are seeking replacements for the centralized stores of skills & proof, socializing, and networking we’ve used in the past. The hodge podge of self reported credentials and certificates we put up on LinkedIn or a personal website is a mess and only allows us one centralized identity. That sucks for privacy and also for people with a diverse set of skills. Recruiters see what we present but that’s never the whole picture.
Some would argue that political polarization will require we either prove identity and in-group or lead us to pseudonyms (identity on/off switch) that let us be judged by work product and proof of skills rather than in group approvals and social validation. Regardless, regulatory capture and special interest groups are now being viewed negatively as younger workers see them as expensive obstacles to career progression. If Kim Kardashian can take the bar without ever going to law school why should you go to law school?
One reason that chaotic is particularly interested in is stores of identity, proof of skills and proof of work capacity is that Web3 and decentralization will pick up the slack in labor markets for younger people.
We won’t want to polish our entire lives in order to get one job with a single employer when we know corporations shows us little loyalty. We’d rather find ways to optimize for our preferred compensation package. That could be flexible contracts and hours, remote first work arrangements, healthcare subsidies, or maximum pay; whatever we chose there should be a recruiter that can find us a job and a workplace that will leverage our skills. If you want inspiration on how this might work I’ve got a list of crypto science fiction to read.
In order to avoid falling into low level service jobs we will need to pick up proof of work and proof of skill jobs. Automation is less of a threat than low level service jobs and dead end work for most young people. Finding ways to get get paid for learning is going to make the jump from play to earn video games to play to learn universities one day.
Portable and “fractional” identities will be required in a future where one person with one job isn’t the norm. So how do we build different identities that keep us safe from context collapse while still giving flexibility and portability on our achievements and documented skills?
All of the above is food for thought. If these problems interest you hit me up. I’ve got a request for startups below. If you want to talk about any of them find me on @AlmostMedia on Twitter.
Request for Startups
Skills repository Github for provable disciplines beyond coding
Web3 LinkedIn where we can turn on and off elements of our credentials
I was having an emotional conversation with a friend. They were giving me a piece of feedback that was truthful but hurt me. Because I feel psychologically safe with them, I was able to take the feedback in a receptive and open manner. I could incorporate it into my mental framework immediately because I trusted my friend. And I knew that their feedback was important and accurate.
One of the traits that I feel is most central to success in founding a company is the ability to process feedback effectively. Founders are constantly getting feedback. An average day might include angry customers with product complaints, a venture capitalist with heartfelt but partially useless advice, an unproductive strategy meeting where no one can seem to align, and a bunch of smart ass shitposters on social media with job advice for you.
A startup CEO gets a lot of feedback. Every day is a deluge of the stuff. And founders have to be gracious about it. Even when a lot of the feedback is useless, or even occasionally downright bad. You as a founder have to decide what to take and what to ignore. Because learning how to synthesize and integrate feedback; positive, negative or even profoundly unhelpful, is in fact your job. Being good at it matters. It’s the closest thing I have to a litmus test as an investor.
This is a trait I prioritize highly in founders. If you yourself are a founder that is working on improving your capacity for feedback processing, I want to hear from you. That mental flexibility is one of the core criteria I look for when I decide on an investment. Do I think you will be able to intake enough information about their market to get to product market fit? Will you be able to adjust your mindset and mental models quickly enough to outrun inertia? How emotionally strong are they that there can hear constant negative input and still hold their positive vision? But equally can you adjust that positive vision when negative feedback that actually matters presents itself.
So this is sort of cheating, but I did write the press release, so I am going to count it as my writing for the day. Today one of my favorite investments of the year Squads announced its seed round. Their vision is simple. Make starting a DAO as easy as making a new group chat.
I was the first yes on the round after meeting Stepan their cofounder and CEO through a cold DM on Twitter. I’ll write a whole post about it at some point I’m a little tuckered from the excitement. So I hope you enjoy the stylings of my extremely formal for normies press release. Any typos are my inability to copy pasta from mobile browser pdfs.
Squads, a DAO creation & management application that makes setting up a Decentralized Autonomous Organization as easy as starting a group chat, announces seed round with Collab+Currency
Squads, an application for Decentralized Autonomous Organization (DAOs) creation and management built on the Solana blockchain, is pleased to announce a $1.5m seed round led by Collab+Currency with participation from Reciprocal Ventures, Volt Capital, Chaotic Capital, 6thman Ventures, Republic Capital, 8186 Capital, Solana Capital, as well as angel investors Ryan Selkis, Ryon Nixon, Chris Hermidaand Julia Lipton.
DAOs have already profoundly changed social coordination and put pressure on traditional corporate vehicles by expanding within the wider DeFi and NFT ecosystems. However, existing solutions in the market are costly to deploy, have cumbersome management features, and are focused only on web 3.0 power users.
Squads is here to simplify the DAO framework and make it accessible to the majority of users who either already firmly exist in web 3.0 or are just discovering it.
“Squads wants to make starting a DAO as easy as starting a group chat,” said Stepan Simkin, Squads CEO & Co-Founder.
Squads combines all key DAO legos such as deployment, treasury / vault management, on-chain voting, and chat in one simple interface so anyone, anywhere can create and run a DAO. By combining these primitives under one platform and building it on a fast and scalable layer 1 blockchain like Solana, Squads will become a social hub for web 3.0 coordination.
Squads founding team consisting of Stepan Simkin (CEO), Deni Ershtukaev (COO) and Sean Ganser (technical lead) comes from diverse backgrounds of software development, law and finance.
While one of the biggest value propositions DAOs can offer is an experience of spinning up a “company” from a command line without any friction or intermediaries, the Squads team firmly believes that “complicated user interface implementations and high fees have made setting up and running a DAO prohibitive for the majority of even sophisticated crypto users. Squads is here to take DAOs to everyone by bringing accessibility to DAO set up and management.”
“Smart contracts are a significant evolution in human organization on par with the invention of the corporation. The recognition by the state of corporations as a single entity composed of multiple actors drove significant economic growth. DAOs are poised to initiate progress as important as the corporation once did,” said Julie Fredrickson, Managing Partner at Chaotic Capital.
“The fiction which we have called the corporation has relied on legal & judicial layers to enforce distribution of resources. With a DAO, the management and allocation of resources is enforced by code, not lawyers or judges. This frees individuals to put their trust in an entity regardless of its geographic jurisdiction. DAOs allow individuals to collectively form complex contracting relationships and operationalize the movement of resources between individuals and organizations for any number of collective pursuits. As Brian Armstrong the CEO of Coinbase noted “the new jurisdiction is online’” said Stepan Simkin, Squads CEO & Co-Founder. “As human collaboration moves online, so too will our organization and tools.”
While DAOs have shown their utility in early use cases in DeFi & emergent NFTs communities, Squads wants regular people to enjoy their benefits. Colloquially known as web 3.0, mainstreaming access to the benefits of blockchains or decentralized networks of many peer to peer nodes, has been slow as few apps provide simplicity and utility.
“Squads envisions a web3 for regular users. A group of freelancers can band together for contract work. A homeowners association can use a DAO to manage and disburse funds. Investment clubs can pool resources. A gaming guild can coordinate accounts. A group of creators can protect their earnings and intellectual property. A sports league can manage equipment and budgets. According to the Squads team vision: “A DAO should be an easy vehicle for groups of different sizes and budgets to easily organize to achieve common goals.”
Squad’s is at the forefront of web 3.0’s next iteration: social coordination. Squads is also positioned as the first mover of DAO tooling within the Solana ecosystem, giving Squads considerable growth potential. “Squads is the team to bridge the huge gap in the Solana DAO tooling ecosystem by building this critical infrastructure and we are delighted to support them” said Soona Amhaz, General Partner at Volt Capital.
“We’re excited to back the incredible vision of Squad’s founders,” said Stephen McKeon, Partner at Collab+Currency. “Squads sees a future where DAOs become a commonplace structure for organizing economic activity. We believe that rather than working for a corporation or nonprofit, many people will work for a protocol someday. So does the Squads team.”
The funding will be used for the beta release of the core product with a mainnet release to follow. Users can look forward to a Squads v2 release with advanced treasury functionality as well as a mobile application for both iOS and Android. Users of other layer 1s can look forward to multichain expansion in the future. The team will be hiring mobile developers, product managers, a network administrator and a designer.
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
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.
