Tag: Venture Capital

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Emotional Work Startups

Day 655 and Accountability

Being accountable to myself is much harder than being accountable to someone else. I suspect this is true for most people. We all wish for ideal childhoods with parents who provided for all our emotional needs. And so we look to bosses, spouses and authority figures as substitute parents.

Most of our adult lives are spent trying to find some ideal mommy or daddy to soften the trauma and lack of our childhoods. We remember these issues far too vividly as adults through the perceptions of our inner child. It is a huge challenge to recognize that feelings are not facts but these feelings nevertheless run our lives.

The unfortunate truth is that the only ideal parent that can ever exist for our inner child is ourselves. We must comfort, protect and nurture that part of ourselves that still feels lacking because no one else can give it to us. No one is coming to save us. We are the parent to our inner child.

Which brings me back to my challenge with being accountable to myself. I struggle to care for myself the way I need as I too often perceive myself as not being good enough. If I just worked harder or spent more time preparing or if I just did one more pass on my pitch deck. You get the idea. I’ll push myself right over the edge of success into inaction and self torture.

One way I’ve been able to overcome this need to push myself into a fantasy of accountability is simply by building in public. If I’ve said what I plan to do then I’m no longer just cultivating it inside myself but I’ve let the idea come forth into reality. Once it is outside of my own tortured bubble of personal accountability it can gain momentum.

I am raising money for a venture fund and now that I’ve put that in public it’s not just about me. It’s about the thesis, the LPs, the founders, and the market. And it’s much easier to be accountable to a shared reality with other people than some fantasy version of perfection inside my head. If you’d like to be a part of it and are an accredited investor here is a link to my calendar. If you’d like to read more about the fund I’d be thrilled.

Categories
Finance Internet Culture

Day 651 and Best Guess

I’ve loved the discourse of indignation that has surrounded rich men doing deals via text messages. There was lot of hand waving about the death of genius and the meaning of it all. Isn’t it such a scandal our best and brightest are just saying shit on Twitter DM?

I suppose if you never worked in startups or finance it might come as a genuine shock that rich techie people are no better or smarter than anyone else. Why the fuck do these dorks control all the money and resources then? I’d say it is because they are willing to make their best guesses.

One of my favorite scenes in Star Trek is Spock struggling through a series of calculations and informing Captain Kirk that he may need to make a guess. Kirk’s response? That’s extraordinary! Spock is naturally confused. Dr McCoy or Bones has to do some translating.


Bones: He means that he feels safer about your guesses than most other people’s facts.
Spock: Then you’re saying… it is a compliment?
Bones: It is.
Spock: Ah. Then I will try to make the best guess I can.

Star Trek IV The Voyage Home (The Whale Movie)

Everyone is just muddling through and making their best guesses. Even the best and brightest among us are struggling to make it all work. I’m not suggesting the folks making the Twitter deal are as good as Spock but they are just making their best guesses too.

And for whatever reason they are willing to put a lot of money, time and reputation on the line to see where their best guess might go. That’s pretty courageous in its own right.

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Finance Startups

Day 649 and Build in Public

People love building in public. The universe loves a specific ask. Today for my 39th birthday, I am doing both.

I would like to raise $5m for chaotic.capital’s rolling fund before I turn 40 next year. #5Before40 has a nice ring as a hashtag right?

Chaotic is the first check into founders and companies that adapt humanity to complexity. Personal flexibility, organizational agility, and societal sustainability.

Our founders capitalize on chaos.

You may have noticed I’m a bit of a doomer. I keep close tabs on the opportunities presented by an increasingly unstable world.

Climate change, distrust of institutions, geopolitical unrest, resource scarcity, rising tides of populism. There are founders who can help us address and survive these pressing issues.

My goal is to raise $500K per quarter via a rolling fund. There is 155K per quarter committed from folk like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company.

With a base like that, I want to do the rest in public here on the blog and Twitter. You can read the fund overview here. Building in public has generally been my preference and it has felt weird doing any of this fund work quietly behind the scenes.

You can sign up on Angellist through the above link or get on a call with me and we can discuss the fund, our portfolio construction and my thesis.

I’ve got big ambitions for accelerating into maturity as I have no intention of letting entropy win.

Humanity deserves progress, and I demand growth for myself. I’d like to make us both money with that. 

______________________

FAQ TIMES

Haven’t you been investing through chaotic before? 

Yes but just with personal capital and an SPV. I want to scale it up as we believe our performance warrants it.

Go check out some of our best investments here. https://chaotic.capital/fund-overview

______________________

Why didn’t you raise more during good times? Why the fuck are you raising a rolling fund at the end of the world?

Did you miss the part where I am a Doomer? We are a bad times fund. This moment is where our thesis matters.

Good times return and you’ll appreciate having written a hedge check or two into weird companies that are designed for the power laws of institutional chaos.

Or if the fear of the moment feels overwhelming you can sit back and die the slow death of uncertainty. Trust me I’ve considered it as well.

But personally, I’d write me $10,000 check and come along for the climb back. Entropy only wins if we don’t fight back.

Categories
Startups

Day 645 and Progress

I was recounting a few pieces of work that have been ongoing to some family last night. Both items were the result of choices and trends I’d been following and cultivating for well over two years. One of the items was even set to debut next week. I had some demonstrable proof points that I was right and right long before anyone else took any notice.

I was extremely pleased to recount the long arc of work that had gone into these trend lines and how they were manifesting in successful investments and media attention now.

Usually when someone asks me what I do I have a tendency to stumble around a few more or less goofy bits. I am retired from working in propaganda. I am a house wife that manages the family budget (this works only with stay at home mom or high net work wealth managers). If I’m feeling chatty I explain the Thursday Styles Problem. If I’m not feeling chatty I’ll just say I’m an investor. Occasionally I will make an attempt to explain the founder to angel investor to venture capitalist career arc.

It’s not actually that easy explaining work that involves years of waiting. If you work for an established name brand venture capital firm it’s probably easier than being an angel investor with a small syndicate or seed fund. But even if you are Sequoia it still takes a decade on average to prove out your bets.

I’m thrilled to have concrete examples to point with any of my investment thesis points. I’m lucky that I have exposure to media so I occasionally get the chance to share what I work on online and in print. Not everyone has the skills to be as visible as I am. But it sure felt great to make some progress. And yes I promise I’ll share publicly when I can.

Categories
Preparedness Startups

Day 632 and The Yips

I think I might have a case of the yips. If you aren’t familiar with the term, it’s most commonly referred to as type of performance anxiety associated with experienced athletes. They suddenly find themselves unable follow through on techniques they otherwise know well.

Though as it turns out it’s not actually a form of anxiety at all, but rather a failure to consistently execute on muscle memory in experienced professionals which manifests as a loss of fine motor skills or a struggle to follow through on common chains of decision making, especially ones that are subconscious.

You might also associate it with analysis paralysis, a phenomenon in which someone has access to all relevant information but gets lost in decision making rather than simply acting on their reasonable informed instinct. One’s ability to simply execute what is in front of them is diminished not through lack of knowledge of experience but rather inaction.

I am an experienced startup operator. I am also a competent angel and early stage investor in private markets with a speciality in technology driven businesses. At this point, I’m not only well into my career with a number of concrete successes (I’ve built and sold companies) but I’ve also got generational memory from being the daughter of a startup operator. And yet I’m still nervous about swimming into the deep end of my investing career. I’ve got the the yips.

I hadn’t noticed that I had the yips till I came back from a wilderness medical incident technician certification course. I was doing a hands on course meant for front line first responders in rural and back country scenarios. It was heavy on scene and scenario execution so you could build muscle memory and quick response times.

In medical emergencies, especially in a wilderness context, you have limited resources and personnel. Acting swiftly with the knowledge and materials at hand is crucial. If you don’t take action, someone will die. Startups are famously resource constrained environments. Paul Graham of Y Combinator has an entire framework that assume you are default dead unless you take action to assure survival. This is as as applicable mindset for wilderness survival as it is for startups.

I had some sort of instinctual foresight that this wilderness medicine course would be useful not only practically in day to day life as someone who lives in Montana, but also as a mindset for my investing work on the chaotic thesis that the world is getting more complex. And that complexity has consequences for all of us.

The more chaotic the world, the harder it is to act with confidence as complexity builds.

Only by getting outside of my own skill set and professional world did I finally see how much I’m holding myself back from acting. Whether it is out of fear or analysis paralysis I do not know. But I do know that if one does not act the consequences can be dire. We are all default dead unless we make decisions to remain alive. There is no safety or progress to be found by staring at your problems and becoming overwhelmed by the challenge. If there is a cure for the yips it is to simply keep playing no matter how hard the game becomes.

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Startups

Day 501 and Do It Live

There must be some kind of residual high from making big decisions, as I’m feel powerful as hell coming out of Montana. I’ve committed to a life path and I am ready to do some thriving. Yes I’m referencing the meme.

unbothered. moisturized. happy. in my lane. focused. flourishing

I’ve got a deal I want to shop around even though it’s ice cold out there in venture land. I believe in the team and I believe in the market sector. It’s a bit of an unusual bet but I have total confidence in the problem space such that I am ready to spend some social capital. So hit me up if you want to get in on the deal. I feel like it’s a deal that’s absolutely in my lane and even if it’s a hard time to circle anyone to anything I may as well enjoy the thrive vibe. Let’s do some magic together yeah?

In another famous meme Fox News host Bill O’Reilly exclaims that “fuck it I’ll do it live!” And I have to say that is my current energy. None of us have a fucking clue about how things are going to go. But did we do our homework? Yes. I did the work. I ran my numbers. I’m good at what I do. I’ve got experience. I’ve got as good a shot as anyone.

So I’m going to say fuck it to a lot more. I’m confident. Because like Bill I’ve got the talent and why not fuck around and find out? This isn’t specifically about the deal I want to do (though I am excited) or the fact that I’m moving to Montana but rather that it’s time to express more confidence in general. I shouldn’t undermine myself. I’m good. Some people like me. And that’s enough to have some confidence to try some stuff and experiment. If you want to come and play with me feel free to say hi.

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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.

Categories
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.

Categories
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!

Categories
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.