Tag: Venture Capital

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Startups

Day 490 and Startup People

One of the more transformative experiences of my young life was attending a founders only conference in 2010. I’d never been around that many other people who did the same thing as me before. I felt so seen.

The most unexpected thing was how relaxing it was to be among other people who understand the context of my life and my work. All of the weird and idiosyncratic elements of being the CEO of an early stage company are hard to translate to someone who has never had to live it. Startups are lonely work and being the CEO is the loneliest job in the company.

Obviously the last twelve years of bull market have greatly expanded the pool of people who have worked in startups. It’s gone from a niche to the driving force of American industry. Everyone grew up. Some of us made money. We’ve professionalized. We’ve developed best practices. What was once a scrappy singular experience is now a repeatable innovation.

And like that conference it is transformative to be seen. don’t feel so alone anymore. There are more people who can share in the context and specifics. I’m in Montana this week with friends who have a similar life path to myself and my husband. Our friends completely understand the context of our lives and we understand their context. We are all founders and executive team members and angel investors and LPs. And yes it’s relaxing. I highly recommend it.

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Startups

Day 484 and Steadfast

Someone who I have come to rely on had a set back this week that briefly threw me for a loop. I initially felt a bit upset, selfishly I felt angry about what the setback might mean for me. That feeling passed quickly. I wanted to jump in and help them overcome the issue. I felt an upwelling of loyalty and emotional empathy that I hadn’t completely anticipated.

In truth, I was honored they shared where they were at with me. Their transparency meant a lot to me. If anything it cemented my feelings for how much I wanted to continue working with them.

Loyalty and steadfastness are qualities that are crucial in startups. Feeling like you are safe enough to bring both the good and the bad to your team makes all of the difference. If you do not trust that your people will remain loyal to you even in times of turmoil you don’t have a team. It’s fine to hire mercenaries at established companies. But when something is new and nascent you are better served being surrounded by those that believe in you.

I emphasize psychological safety in my writing and on chaotic.capital’s website because I think it matters more than almost anything else. All things being equal, psychological safety is the differentiator in who survives in a startup. Having the confidence you can share your creative process matters a lot.

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Internet Culture Startups

Day 479 and High Agency

A corner of startup Twitter was discussing the relative ease of getting connected to power brokers in different industries today. The debate? Does good talent eventually finds its way to resources? The contention from Roon, otherwise known as Mr. Wordcel vs Shape Rotator, is that networking is less crucial in technology than in any other industry because it’s easier to find a way in.

While one can quibble with how true this is for all populations, it is truer than it’s ever been. A large swath of the startup ecosystem is readily available to anyone on social media. We are less constrained by geography and credentialism than we’ve ever been. This is partially because much of the wealth in the current generation came from building social networks or software that benefits from openness. An excellent overview of this is why good angel investing ecosystems prioritize welcoming newcomers by Alex Danco. Most investors want to be available.

But it’s still a challenge to find high agency and high talent people and there are far fewer of them than you’d imagine. And proving you are high agency and high talent isn’t always an intuitive process. Being able to assess if someone has the capacity to build is one of the hardest job a capital allocator will ever have. Judging markets and products and roadmaps is much easier than discerning if someone has the capacity to execute on their dream.

I personally use follow up as my first heuristic. This is partially because I maintain open DMs so literally anyone can and does reach out to me. If someone is able to regularly show up and engage with me and show progress they are better than 90% of people. Honestly go ahead and try! I really am here to help.

You’d be shocked at how often someone pitches me and then I never ever hear from them again. And it’s not because I missed the boat (this happened once to me this year). It’s generally because people are waiting for someone else to act. And this is where people fail. The first rule of startups is figuring out how to create momentum. If you are waiting for me to cut a check you’ve already lost.

I’d like to do a whole post on this topic but I’ve been struggling to get the bulk of it on paper as I’ve got a migraine coming on. But rather than put the post off, I organized an introduction of the subject and put down my first heuristic. Which is ironically exactly what I look for in founders and builders. Did you make some visible amount of progress no matter how bad? Did you put it out into the world? That’s better than most people!

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Preparedness Startups

Day 474 and Unsettled

I don’t own a home. It was never a financial reality before the pandemic. But then the world accelerated and suddenly we had options and money. But still it seemed impossible to commit to another asset with a long time horizon even recently. We were startup people so every other asset was a long hold.

I don’t feel that way anymore. I have written about how I would like to buy a home now. I feel like it’s time to find a place where we can build some stability. But of course the chaotic thesis haunts me.

The chaotic thesis is the one that undergirds all of my investing. The world is getting more complex. That breeds chaos. The biggest macro-level mega trend of the next decade will be adapting to the chaos.

And as it turns out adapting to chaos is really hard. Everything that allows you to cope with the chaos in high demand. A safe place to call your own? Sorry, it’s never been harder to become a homeowner.

I wish I could say that knowing this is our reality makes it easier to adapt. Knowing isn’t the battle as it turns out. Acting on the knowledge is the hard part. Making good decisions under pressure is what will separate out who thrives and who merely survives.

I don’t think it’s going to be pretty and I’m genuinely worried it’s either hit the singularity or a new dark age. There is a reason we think we need the metaverse and it’s not because reality is getting better. It’s because it’s getting worse. I allowed all the web3 kids working out there working on Plan B.

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Startups

Day 470 and Social Skills

Startups are just as much about social hacking as they are hacking something technical. We worship the archetypal “coding nerd” who is brilliant but awkward, but in reality building shit requires an awful lot of social finesse.

I meet with a pretty wide range of founders. A lot of them are clever but relatively normal people. But many founders are fucking beyond weird. I see a lot of neurodivergence. But it’s not all towards the awkwardly autistic. Plenty of founders, especially in web3, are almost supernaturally charismatic. No literally it’s magic.

And that magic is good for making something new. The ability to empathize and listen is hugely prized in leadership. Being present and able to socialize in any social context is key to bring diverse groups together. We are much more willing to throw in our resources behind a founder who can rally us together. And this is just objectively good for the startup. Of course investors want to back that kind of person.

I think some people are offended by this reality. We see endless pop culture depictions of narcissistic sociopaths raising shit tons of money and then destroying their companies. I’m honestly a little sick of it. It’s no secret that Silicon Valley, but capitalism on the whole, occasionally rewards charlatans. I don’t think it’s particularly indicative of anything but human nature. Like Fox Mulder I too want to believe.

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Startups

Day 468 and Small Moves

One of my favorite movies as a kid was Carl Sagan’s Contact. It’s not a great movie but it’s heart is in the right place. It’s a beautiful story about human curiosity and the long timeline of history. In one of the closing sequences the protagonist is told by alien intelligence as embodied by a representation of her dead father that all next steps are “small moves Ellie.”

I never feel like I’m moving fast enough. Every day presses against me. I long to slog through them with speed and alacrity. It’s almost embarrassing how inadequate I find my progress. But then I remember that I move fast. I live ahead of the mainstream. I get to sit in the future that William Gibson said was not evenly distributed. Even if I don’t think I’m particularly good it’s hard to deny just how much of my life is lived in a tiny sliver of humanity.

Someone recently asked me how I moved so fast when I’m dealing with a chronic illness. I found it to be such a shocking question. I feel like I’m glacial compared to the reach of my desires and imagination. But then I’m reminded that even in shorter hours I’m forced to hone my crafts. I can’t afford to waste energy or focus so I simply do not. I imagine this focusing out of need is similar to what parents of young children operate in. The subtle art of not giving a fuck.

And so what if I am slow on a day to day basis. Rome wasn’t built in a day. I’m not a market trader. I invest in ten year cycles. Everything in venture is actually small moves. But as time adds up so do the aggregate of the moves. Compounding interest is up there with gravity as a force. So even when I yearn for more and for it to arrive faster I have to trust the numbers.

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Internet Culture Startups

Day 461 and Remora

I saw a headline about how Trump’s social media site is failing. I’ve got no idea if that’s true but the media likes the story. This is playing out in the context of Elon Musk using corporate governance as a public relations stunt with his new Twitter board seat. Everyone wants to be an attention grabbing technology company even former presidents and aerospace billionaires. Because even the stupid stunt stuff in tech can be world changing.

I’m at the big Bitcoin conference in Miami. It’s a lot but it’s not fundamentally any gaudier than any other industry event I’ve attended in twenty years being adjacent to startups. Before my current stint as an investor I worked in fashion and beauty so I’ve seen a lot of excess. M I was raised in a boom time Web1 startup family. But also my family went bankrupt. I’ve seen the dark sides. I still work in tech. Like Trump and Elon I too just want a piece of the action.

It’s because startups change the world. Even stupid weird dopey absolutely cult adjacent shit can and does change the world. All these prestige television takes on frauds and crashes and the cult of personality nonsense miss that sometimes those freaks actually do it. Sometimes they change the world. Ok most of the time they don’t. See the current unraveling of Fast. 99% of the time shit goes bad. But to have even a little bit of the action of the 1%. It’s fucking dazzling. It’s worth being adjacent to all the bullshit.

I hold in high esteem the folks who work at the flameouts. Anyone who takes a chance and has it go bad has my admiration. I’ve been one of them. I’ve failed a lot. I’m lucky I don’t get punished for it. At least not much. I’ll never know how much shit like my gender or my ridiculous social media personality factor into that shit. Because I am always allowed to get right back into the action and make shit. Making shit is our currency.

I think this is why even the most powerful people gravitate towards startups. You actually get to make shit. At the earliest stages you get to be personally responsible for so much. Your actions have meaning. You contribute. You know how rare that feeling of community and camaraderie is in peacetime?

It’s a commodity so precious we let ourselves be led by girl bosses and fast talking celebrity thought leader venture capitalists. We tolerate a lot of assholes and psychopaths so we can be in a community of people that make things. It’s the American dream and the most basic human need all rolled up into one.

That ought to give you a sense of the cultural power and vitality of startups. That’s loyalty on par with religion. That’s move history big dick energy. And I think some people hate it I find the hate inscrutable but I’m sure it’s probably legible to those who feel left outside.

So yes boom time early energy big money hanger on remoras are part of any thriving ecosystem. And as far as I can tell Bitcoin has the manna to go the distance. Because everyone wants a piece of the action.

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Startups

Day 452 and A Short Guide on Cold Outreach for N00bs

I have an open Twitter DM policy for founders. I encourage outreach to me via all forms of asynchronous communication. I think the hour long pitch, either zoom or IRL, is a bad way to get to know someone. But that doesn’t mean there aren’t rules and social graces involved in cold outreach. I’ve outlined an FAQ on how to get to know me and what I look for in founders but it seems like people would benefit from more tips on how to ask for help and investment on social media.

1. Give Me A Synopsis

If you are sliding into my DMs remember that I’m probably just glancing at an alert. You want to get across just enough context to encourage me to pop in and take a look. And remember you don’t need to convince me with one paragraph. I want to develop a relationship with you and learn how you think. That’s not possible in a few sentences so remember that synopsis is just the beginning.

2 Use A Social Account With Shared Context

I’m always surprised by people who slide into my DMs with 15 followers and a blank Twitter profile and expect an answer. Use the shared social graph to show your interests and tastes. Follow and be followed by people in common with me. You’d be surprised how much meaning I take from seeing you follow and interact with people I respect. The social graph is now we vouch to each other we’d enjoy spending the next ten years working together.

3. Tell Me Who You Are

Make sure you’ve got a link to a personal website so I can learn more about you. It doesn’t have to be elaborate. I think LinkedIn is lame but it’s easy and shows your skills and career path. Hate that? Link your TikTok or Tumblr or blog. Are you anonymous? That’s totally fine. I’ve funded anons. Give me the portions of your identity that are on chain or under your pseudonym so I can learn more from there.

4. Rome Wasn’t Built In A Day

You don’t need to ask me for an hour long pitch or even my email right away. I don’t need perfection from the start. Just say you are working on something and want to talk to me about it. Say you will send me a white paper or a blog post and ask me to read it. Then follow up in a few days to see. Don’t get social anxiety about it either. I probably just forgot or got busy and I love being reminded. Truly.

5. Only Ask for Favors After You’ve Demonstrated Rapport & Competence

I cannot tell you how many times I’ve been asked to for advice, help or investment in DTC, CPG or retail type businesses which I have explicitly said I do not do. But what’s even wilder is that the question right after I say no is almost always “well can you introduce me to other investors that do?” This isn’t an inherently bad thing to ask me. I want to help. If you’ve shown me a great product and I’m engaged and impressed with you as a founder and we’ve had a few interactions ONLY THEN do we have enough of a relationship where it’s ok to ask me to spend my social capital to help you. I can’t help you till I’m sure you can help yourself and that means demonstrating you won’t waste the time of my network as well. Favors are big asks and I only want to use them on people who will reflect well on themselves and on me to my network.

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Finance Startups

Day 432 and Send Me Dealflow

The markets are struggling with the chaos of the Russian invasion of Ukraine. Nickel prices doubled. Gas is skyrocketing. Central banks are due for rate decisions but it’s anyone’s guess as to whether hikes will manifest. But in my neck of the woods uncertainty is our business. Chaotic.capital was founded on the belief that an increasingly complex world would present opportunities. And I’ve never felt more confident in our thesis.

With chaotic.capital we’re identifying, investing in, and supporting companies that adapt our lives and systems to the opportunities that chaos brings. We like companies that are adaptable. We like companies that help others become more adaptable. If you are still building in the chaos and want an early stage pre-seed or seed stage investor I’d like you to drop me a line this week.

I believe it’s possible to find leverage in chaos. As scary as this moment feels, it’s possible to profit off of the many ways the world may change. Geopolitical instability isn’t going away. That’s got downstream effects. Think supply chains remaining strained and snarled. Commodity prices continuing to be wonky. People on the move from immigrants to refuges. All of these problems will be opportunities for businesses to improve lives and make money. Everything from logistics software to temporary housing falls under the chaotic remind.

We are not scared of weird bets. We like unsolved problems. If it’s easy to model your growth and the exact trajectory to success, we may not be your partner (though we’ve got friends who will love you). But if you have a point of view on how chaos will enable your success, we don’t need a perfect plan, just a possible future.

Just to give you you an idea of how serious I am about finding weird shit let me tell you the deals I’m excited about this week. I’ve seen an occult marketplace, a real time DeFi data platform, a marketplace for vegetable gardens, logistics and 3PL software for influencer boutiques, and AI assisted direct to consumer abortions. No problem is too weird for us. So come on and slide into my DMs.

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Medical Preparedness Travel

Day 419 and Back to Normal

One of my friends texted to say “I’m shocked the hygiene theater at EthDenver failed as half my team has Covid-19!” Which is of course sarcasm. But we are all back in action. Consequences be damned! I’ve booked conferences through June. A venture fund that backs my husband just booked their CEO summit for an in person gathering. I have finally started eating at restaurants indoors again.

But for all this ridiculous talk of getting back to normal it’s just a lull. I’m happy to be out there as I’m confident in my immunity and my own risk tolerance based on having had an infection and being up to date vaccines. But it might not remain that way. And for plenty of people their risk calculus can’t be as liberal as mine. We’ve left behind the immune compromised. America doesn’t give a fuck about the disabled.

I hadn’t really meant this as a Covid post but rather it’s an introduction to this striving for normalcy. The pandemic is wrapping up and we can “Get Back to Normal” is more slogan than reality. If only because there is no going back. We’ve got the annoyance of all the second and third order effects of the pandemic to deal with now. And that is going to suck more than the pandemic

Faith in institutions is shaken and probably damaged for an entire generation. Health and medicine will make big strides as we finally address long virus issues. Maybe more chronically ill folks get better care. But for most people their trust in science is shaken. Not sure if the good will outweigh the bad yet.

We’ve also normalized a wide swath of government interventions we’d previously never tolerated. But it’s for our own good! Sure but who decides on the good going forward? What might else it get used for? And more people than I’d expected cheered on this kind of meddling in our daily lives. All for the greater good obviously. But I’m worried what happens when fascists get to decide on what is a greater good. And since we’ve normalized intervention it will be harder to push back.

I really do believe things are becoming more chaotic. We’ve accelerated a whole swath of changes that are going to shift our world. Some of it may be in good ways. I certainly plan to make a lot of money investing in the belief that we will adapt swiftly and positively. And either I’m right and we survive and so I make a lot of money. Or I’m wrong and it probably doesn’t matter. We’ve got to leap into the unknown to find out. But back to normal? Sorry buddy but we live in interesting times.