Tag: Founders

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Startups

Day 1534 and Certitude

I’ve been busy with a founder who is running an astonishingly competitive seed round. Let’s just say I’m glad I wrote the first check.

I back founders long before it’s possible to have any certainty. I have accumulated enough signal and taste over twenty years to feel like I know when someone has what it takes to try their hand at a startup. It doesn’t mean it will work but I always believe in their capacity to do the work required.

Proving that out is probably the work of millions of pages of business school papers. No wonder we are complaining about the lack of builders. Wouldn’t it be better if we just put those resources into starting actual businesses instead of theorizing?

I’m a huge fan of always being a bit entrepreneurial. The much maligned “side hustle” that millenials and zoomers maintain out of necessity has its upside.

I like all scales and all kinds of business. Alex and started dating thanks to a swap on an Airbnb rent arbitrage. I’d let someone book dates for my apartment when I was supposed to be out of town. Trip dates change. Alex offered his apartment up if we split the profit. We’ve been in business ever since.

I’m working through a new local business plan we think will have community benefit (both in terms of job creation and service offering). Am I certain it will work?

Actually more certain than you’d expect this small scale that we can boot something up. Startups are much harder to judge than an existing business model with a new offering.

Incidentally if you are in Montana and looking for a medical grade hyperbaric chamber oxygen treatment we should have ours in a month or so.

Categories
Culture Startups

Day 1522 and Rollercoasters

Startups are such rollercoasters. It’s always been cliche but starting something from nothing really is a wild ride. You can experience the lowest of lows and the highest of highs in the space of a day.

If you enjoy adrenaline being a part of a startup is fun as it is equal parts terror and exhilaration. There are presumably other careers where this is also true. I imagine mothers and marines can tell you a lot about dealing with intensity.

I have had to remind myself quite a bit lately that nothing is permanent. As we push against a higher and higher variance future I feel equal parts exhilaration and dread. I don’t feel as safe as I’d like. But I doubt I could be more prepared.

The stress of a startup can kill you if you let the stress of the wider world weigh too heavily on you. We can enjoy the fun of the ride. The safety is an illusion anyway. Well maybe not on the rollercoaster. Those have seatbelts.

Categories
Emotional Work Startups

Day 1520 and Reflexively Negative

When I was younger I would try to demonstrate my cleverness by pointing out problems. Like many precocious youngsters, I was certain that this behavior provided value.

It’s exciting to feel the power that comes with understanding. It is especially intoxicating to students. No one is so fervent as a new convert.

Finding errors in reasoning, gaps in knowledge, poorly laid plans, and lapses in judgement can all be helpful when they are put to use in finding a path to success.

Being able to humbly accept corrections to one’s worldview or understanding when in error is crucial to being able to understand your reality. No one values that more than people who must succeed.

Alas, because finding and correcting misunderstanding is so important, it’s easy to slip into reflexive negativity as your only tactic. You mistake finding errors with being the only valuable contribution. It’s a classic problem with engineers. And unlike the young they rarely outgrow the habit.

Any founder who has had a pitch with a venture capitalist who can only focus on the problems and not the potential, understands why this it is unproductive to rely only on spotting issues. Being right about something being wrong doesn’t build anything.

Categories
Emotional Work Startups

Day 1515 and Hope in the Dark

Given the amount of illness that seems to be plaguing folks this winter I’m surprised we’ve not all decided to hide until Spring thaw.

Every event seems to be a super spreader. Our physical immune systems are shot and I doubt our emotional defenses are much better. Everyone is predicting informational dangers myself included.

It is hard out there and we all experience it in different ways. My medical improvement sprint is plagued with logistical issues, the mold situation in our basement is overwhelming, and yet I have hope that I’ll make it.

o many people are dedicated to building solutions to problems, big and small, that I can’t selfishly let my any of my problems stand in my way. We have to all pull forward together.

I spent a few hours with a portfolio founder working on their fundraise today and I felt my optimism. I enjoyed the flow of work even as the enormous task of raising capital is filled with risk.

I’d taken a risk on directional play earlier in the year. I believe in the founder. They are making their way through YC. I can see their path emerging with every step forward. And I see hope.

Categories
Internet Culture Startups

Day 1434 and Density

There is always a debate in startup life as to how the density of a given ecosystem impacts outcomes. A tight network of well connected communities and individuals helps founders, investors and talent connect.

Before the pandemic it was considered fairly normal to be within a major hub as the common knowledge was that “density” matters. You wanted to be in the action of a scene.

There are great startup cities. New York has an incredible scene. My hometown of Boulder has a great technical core. But as much as cities and companies compete over status the one with longevity is Silicon Valley. Heck it was a debate when that even encompassed San Francisco until Twitter moved in.

Then everyone spread to the four winds during the pandemic. I like to think of this as the era in which Silicon Valley got back to its digital roots. Being extremely online became a behavior that worked well for anyone if you communicated well with words. Being on the right coast was about being in the right online communities. The network state is online.

I’d say that was as pure a return to source culture as there ever was. Different people value signal across different networks and the open web of words has been home to software and hardware developers for generations.

The world that builds companies lives virtually as much as it does in the real world. We like to meet up but we also know it’s the tools that connects us that make the difference.

Every subculture that has emerged with a breakout hit did it through the digital commons we built together. I’ll always appreciate coming to the source culture to replenish but I know the density of the network is at its swiftest when our extremely online communities communicate.

Categories
Community Emotional Work

Day 1428 and Thanksgiving

It’s nice to have a record of multiple years of thanks to look back upon. In 2023 I was thankful for the serenity of acceptance. In 2022 I was grateful for regaining optimism. In 2021 I was grateful for the small measure of health I’d gained.

In 2024 I’m still optimistic (albeit cautiously) as I have the similar amounts of health and acceptance keeping me above the waterline of our chaotic reality.

I am thankful the incredible amount of progress I’ve made in my work this year. We’ve done so well with our first fund at chaotic I have little fear that we will continue building it even as the markets remain a challenge.

I’m thankful for our founders who made it possible for me to make a go of investing in weirdos.

I’m thankful for my marriage. Alex and I have made it to our second decade together. I highly recommend marriage if you get the chance.

I’m grateful for so much this year that listing it out seems a bit overwhelming at 8pm at the end of the day.

But if you have the chance to be grateful in writing it’s worth doing. Looking backwards on your gratitude enables you to look forward with optimism.

Categories
Startups Travel

Day 1424 and California Dreaming

We’ve just had a beautiful snowfall in Bozeman. If you are back up on the mountains at the edge of the valley you are enjoying a mystical winter wonderland.

Alas I am not long for cosplaying Frozen (blessed) as I am headed west. No, I am heading not to Seattle the most important city of the 90s. I am headed to Joan Dideon land. I’ll be in California.

I’ll be in Los Angeles for the week or so if you happen to be on the west side. I’ll then be headed up to San Francisco.

It will be a little whirlwind of family, friends and hopefully some useful business. I’ll be visiting start ups. Going to YC Demo day which I have not done in person. Meeting up with anyone who might want to be a node in our network.

I am game to meet up with folks working on weird shit and are looking to build it. I am also looking for LPs in our next fund so we can keep funding the weirdos who build things.

The virtuous cycle of techno capital starts long before an opportunity is clear. If you have something chaotic in your heart send me a DM

Categories
Internet Culture Startups

Day 1421 and Culture Clashes

I sit in between half a dozen different community nodes thanks to my interests in open source software, decentralization, crypto, and autonomous systems technology.

This set of interest covers a lot of ground from ecosystem level collaboration in financial organizations like DAOs and to player versus AI agents coordination to peripheral control of drones and machinery.

Many different demographics are attracted to these frontiers for different reasons. Hackers have a very different mentality than mercenary technologists looking for maximum margin.

Open source has traditionally struggled more from a lack of financialization than from an obsession with it. Which seems less true in the crypto era than in previous more academic and defense oriented eras.

There are classic open source business models and anyone with age and experience in startups has some opinions which I leave as an exercise to the reader. They occasionally fail and an open core loses more than they’d like to professional services. I am writing on WordPress.

One strange aspect of what drives these frontier spaces to interact is that depending on how much leverage you find in building a network you may have different incentives than other builders and users. Expanding out to scaled use may drive a lot more value than the resources required. How the surplus gets divided is always contentious.

For some, the most crucial cultural goals is expanding access to automation and ripping away as many of the services and middle men as is feasible.

Decentralized systems make it harder for middle men to maintain monopolies. Thats its own goal for true believers. For others the goal massive financialization that drives network connectivity is the benefit. Self interest driving common goals is perfectly acceptable.

As I watch the current season of hyper self interested memecoin cryptomania engage with the academic utopian open source artificial intelligence community, I am reminded of so many of the classic issues we have in financing and sharing in the spoils of common infrastructure. Who benefits is a question we should all be asking more regularly

Categories
Preparedness Startups

Day 1419 and Know A Guy

Running a startup, for all its supposed glamour, is mostly an exercise in learning how little you know.

Sure there are playbooks for some of what you will do. As the technology industry has grown and startups have become an appealing career choice we’ve filled out how-to guides for everything from fundraising to operations.

Alas all advice is specific to the giver’s experience and untangling biases to make advice relevant to your specific needs is quite hard. That’s where it helps to have more experienced operators on hand to call bullshit.

At chaotic.capital we pride ourselves on being investors who “have a guy” for even the most esoteric possible requests. Playbooks can only you so far when you need an expert.

Just in the last two days we’ve worked through how one hires a chief of staff, what to do when letting go of counsel who made a mistake, installing appropriate security procedures for digital footprints, and the resale brokers for a rare commodity.

We like to problem solve and the weirder the problem the more fun it can be. Removing obstacles and clearing bottlenecks is satisfying work. And knowing guy who knows a guy is a heck of a fun game of social geography.

Categories
Aesthetics Culture

Day 1418 and Winter Wonderland

I’m in a terrific mood. Maybe it is just the hormones cycling up. Maybe the red lights we installed in the bedroom are actually improving my sleep quality. Maybe it’s getting a foot of powdery snow over the weekend.

So much of life seems to boil down to manage my own circadian rhythms even as I plug myself into the hiveminds of my favorite corners of the internet dutifully everyday. And my body likes short days, long nights and the bitter cold.

Certainly success is contributing to my buoyant mode. All of my founders are soaring (which seems statistically rather unlikely given the choppy markets) and the vibes are good. My chaotic.capital clique is thriving.

It’s getting to the point where I think we should host a portfolio dinner or something. Though that would be challenging as we are a distributed group. Alex realized recently that we only met one of our portfolio founders in person before we invested. Can you even imagine that in a pre-pandemic world? Our deal flow comes from the virtual worlds I live in daily.

Being snugly ensconced inside several areas of with macroeconomic tailwinds doesn’t hurt but most of those choices were made two or three years ago so I’m simply directionally correct, well connected, and unafraid to commit once I’ve satisfied my own process. Everyone has a long way to go but it feels wonderful to enjoy their success.

Walking in a winter wonderland.