DelaneyM

Cayman is absolutely thriving actually, our biggest political issue is currently whether we should throttle growth. (Projections have us growing by 10%/yr in population, which is a bit scary.).

Our biggest business here isn't tourism, it's finance and professional services. Our differentiator is being one of the only "legit" tax neutral locations with strong legal protections. If you want to be able to send large amounts of money anywhere in the world quickly and legitimately, without tripping a million anti-laundering provisions, this is almost your only choice.

There are very few Americans here because there's practically no corporate veil - a Cayman company is far more transparent than a Delaware company. This is a terrible place to hide funds.

There are more Canadians here because Canada doesn't tax overseas income for non-residents, but Canadian-resident individuals don't get much out of a Cayman shelter. There's a bit of a "loophole" if you own a property here through a shell company, in that you can rent that property and keep the funds here tax-free. But that only works if the rental is generating and using the majority of the funds, and it's totally transparent if CRA comes knocking, so it's pretty limited in utility.

It used to be a bigger thing in the 80s/90s, before the world started cracking down on "tax havens", but the biggest change has been in enforcement. I wouldn't be surprised if some "old money" on the island for decades is grandfathered in to better tax treatment, I've heard as much, but that's a CRA thing and not a Cayman thing. In general, Cayman has never been a place to "hide" funds, it's been a place to legitimately put funds if your country of tax residency privileges that. Tax loopholes aren't on the Cayman side, they're on the US/Canadian/UK side. Don't drag us into that mess.

Also Cayman rum beats Jamaican any day of the week. That's going too far.

It's quite easy, the biggest question is whether it's worthwhile.

Important: IANAL!!!

You can open what's called a "Cayman Islands exempt" company, which can exist here in Cayman jurisdiction but which cannot do business in Cayman (basically don't compete with Caymanians in Cayman). This is generally how holding and investment companies are structured. _However_, this doesn't shield you from either personal taxes or visibility. Cayman is much more transparent than, say, Delaware. And if the book value of investments grows and you're American the IRS will find you quickly (if you have any assets in Caymanian banks they'll report your activity to US authorities regularly, even without a warrant or request.). KYC here is no joke, it took me a month to open a bank account here and I'm a permanent resident with Cayman parents.

Since this is HN though, you may be interested in a "fully remote" company with no real home - that works quite well here. You can pay contractors anywhere without holdbacks or forms and let them be responsible for their taxes (be aware of Nexus rules though, it's not foolproof.) You'll generally be responsible for taxes in the countries where you book income from that country, but (consult a lawyer) not always for SaaS. The biggest advantage IMO is that you'll be able to cut your paperwork down enormously because Cayman just doesn't care about the flows of money (so long as it's documented for laundering/tax avoidance reasons). Nothing to file, nothing to pay.

Finally, let me plug the good folks at Cayman Enterprise City. https://www.caymanenterprisecity.com/. They will set you up to actually have an office and presence here (in a really nice building downtown!), they can give some light legal advice and guidance, and if you have employees anywhere in the world who want to relocate to paradise they can get them a visa in a day or two to move here.

So yeah, it's "easy", it's not terribly useful for tax mitigation directly, it's (in my admittedly biased opinion) one of the best places in the world to anchor a truly global startup.

If you can share more context I can try to be more helpful? But likely the next step is an actual professional accountant/lawyer.

Hey, Caymanian here! This is interesting reading, but I feel like it misses the point.

I know a lot of people in the finance & professional services here, and I think what's missing from this analysis is how Cayman bends over backwards to make it _easy_ to do business here (especial finance).

It's tax neutral but fully transparent to and compliant with UK, US, EU, and Singaporean (as well as many others). This means if you're operating a hedge fund (as an example) with high net worth clients and private investments globally you're generally able to hugely minimize the amount of paperwork to not be double-taxed. It also lets you run financial instruments which might be subject to tax while operating, rather than when earnings are captured and released. And yet, it does that without being on any global watch lists.

Financial courts here move _fast_, often ruling and concluding in weeks. And precedents are generally British Common Law (unless improved by Cayman). Starting a company is easy, and fees cover pretty good support. I have a Caymanian company, and when I had a question recently about identification regulations on non-voting shareholders I could call a number and get both a quick answer and great advice from a human being.

It's worth noting that Cayman has virtually no Crypto because of the above. We've actually tried, but no significant crypto company has been willing to subject itself to the relatively lightweight regulations. The biggest crypto startup on the island is a crypto regulatory compliance tooling company, which says a lot.

Anyhow, I'm not a lawyer or accountant, butt AMA I guess if anyone is curious about my home! :)

(It's also an amazing place to live, I love it here. Hard to recommend though because residency is notoriously hard to get if you're eligible through ancestry.)

I didn't think I was going to switch to Mastodon - I try to stay apolitical and I mostly used Twitter for news and influencers/disseminators with large followings who weren't moving.

And yet, here I am, primarily using Mastodon. Maybe it's just my server, but it's so much more _pleasant_ to be there. I don't need to wade through pages of insanity and irrelevant ads to get to the content I care about.

It's as if an annoying ambient buzzing slowly built up in my favorite coffee shop over a decade, and I never really noticed it, but now there's a crunchy alternative cafe next-door with fewer options which is blissfully silent. I just can't bring myself to go back.

Generally I agree, but unfortunately many newer, denser, cities can't be easily rezoned/rebuilt into residential/mixed use because the city infrastructure (usually plumbing) can't handle it. So major conversion projects need not only zoning approval but also major municipal investments.

It turns out zoning is not just an arbitrary categorization, but also a guidance for public works. This is a tough trap, because it's hard to convince a local gov to put up much more capacity than required for office use when an office building goes in (that would be a waste of taxpayer funds).

(I've tried to do this, even put up capital and hired an architect, but it hit this wall.)

Something not mentioned yet (at time of writing) is the importance of self-healing data.

You can always just hard-restart an app every minute or so to be resilient to nearly any failure condition in runtime (not that I've _ever_ done that before...), but if the data gets into an invalid state you're stuck.

The one time I needed extreme resiliency and recoverability I used a write-only DB with a materialized view which updated on change or startup, and every write in a transaction. I also tailed the DB updates to a file on disk which replicated regularly off-site. It could automatically recover from nearly anything, and was remarkably easy to set up. The hard part was the materialized view, but I "needed" that anyways as I wanted to keep a full audit log as the primary db.

What constitutes resilient data is going to be unique to your use case of course, but consider resiliency from the DB up.

Also I suggest investing heavily in grokkable and relevant runtime observability. (Don't just emit inline comments, put some thought into relevant data and alerts.). Often you'll see a failure coming days ahead of it causing a problem, and you won't need the app to self-heal.

When I read overwrought complaints like this, I can't help but wonder what heretical "revolutionary/exciting" thoughts they are "prohibited" from expressing?"

There are lots of courageous people out there challenging societal norms, but without fail it's reactionary conservatives complaining about being criticized for picking on them.

Trans kids in Texas? Unquestionably brave and very likely fascinating people. Conservative lawmakers trying to legislate them out of existence and upset about being criticized? Not so much on either count.

If the author wants to meet interesting people, they're out there. If he's looking for permission to express his inner monologue, he's not one of them.

It's self-sustaining at this point.

I wouldn't bother with an accelerator largely because I know I wouldn't find a social fit, and the informal connections are so much of the value prop. If YC had 25% women, they'd get to 40% pretty quickly. But so long as they're <5%, it's going to asymptotically approach 0%.

Also I'm confident that biases would factor into not only YC selection, but also (and more importantly) the investors who traditionally work with YC companies, since they just don't see women outside of "fem-tech" and fashion, in part because that's how YC selects.

My perspective may be as much a product of my pattern recognition of consistently having to deal with sexism as it is the valley being sexist, but either way I'm just done with it.

I have empathy here for the founders, going through all the overhead of finding a great candidate (you only saw the time invested in you, not the time invested in all the other candidates), then realizing you have to restructure your entire runway when conditions change or reality asserts.

> Perhaps they started hiring on the expectation of being able to raise money, but that seems unprofessional and disrespectful towards the candidates, no?

They were 100% doing this, and that's pretty much the base case for any VC-funded startup. If you believe this to be disrespectful than I advise you to stick with profitable/public employers.

If anything, appreciate that they didn't try to hire you in spite of their financial squeeze, then end up laying you off a few months later with minimal severance because they overran their runway.

It's much more impressive than that:

> Upon completing her transition in 1968, Conway took a new name and identity, and restarted her career in what she called "stealth-mode". (From https://en.m.wikipedia.org/wiki/Lynn_Conway)

She managed to have groundbreaking impact in two disconnected careers after restarting from scratch!

This is yet another factor which drives homogeneity in venture as well.

I have lots of friends and associates who I work well with and respect, but none are "tech people.". They're teachers, nurses, retail entrepreneurs, etc. I appreciate them because they are not like me, and after always being in a small minority in my education and career they're my people who keep me grounded. None could be a co-founder.

If I had a nickel for every time a VC suggested they could "help me find a business co-founder (CEO) with tech credentials" (all of whom were white straight Stanford dudes) I'd have 15¢, which isn't much, but it's depressing that it's happened thrice.

How could it?

So assume there's a normal distribution of price possibilities at each purchase point. You're going to end up with the _sum_ of those distributions, not the correlation or combination of them.

Presumably the deviations of those are growing more larger over time, but the are still the same underlying distribution curve as they sum up. The mean will trend steadily upwards.

The resulting price will be a normal distribution with a deviation of somewhere around the midpoint, and a mean of somewhere around the midpoint.

Now, with the mean increasing over time, your expected return will be decreasing the longer you wait. But what about the risk:return?

Unless you have outside knowledge about risk growing or lessening over time, it will remain constant over the DCA period, which means the risk factor of your investment (the standard deviation of the resulting DCA price) will be at exactly the midpoint of your purchase series.

So your expected return will be slightly lower, and your risk profile will be substantially larger, than just buying immediately.

DCA: math does not check out, not even close, _if you have all the money upfront_.

> If you invest at a few different times, whether fixed interval or random, is this not increasing the probability of approach an average value over the period you're investing?

It does indeed increase the probability that you will approach the average value over that period.

But there's no reason to believe that average will be lower than the current value.

I'm adding no assumptions, and my view is math.

The only thing we know is that we're choosing an asset which we believe will trend upwards.

Over the relatively short period of DCA, it will trend upwards.

If you're saying you know that the rising trend won't begin until a future date, then that's an assumption you're adding, and it probably indicates you should wait until the rising trend begins until increasing.

If you're just "not sure", buying puts wouldn't help. Running puts & long on a single equity is assuming a specific yield shape.

A good example would be an upcoming test result report for a pharmaceutical - it's either going strongly and gradually up (long) or suddenly and significantly down (put), but not gradually down (in which case you'd be out on both puts and longs).

But yeah, at this point you're a super-sophisticated investor and all of this discussion is meaningless. :)

The intuitive leap which is hard and important is how "not knowing" works.

Presumably you are choosing to invest in an asset because over the long term you believe it will go up. But you know nothing about what it will do in any defined timeframe.

Choosing to DCA with a fixed strategy is choosing x prices at which to enter, of which (x-1) are unknown. But they are fixed, and based on your above assumptions you know nothing about them except that they're generally trending upwards (and thus your entry price is averaging up by DCAing). Knowing nothing means knowing nothing, it's as likely to vary upwards as down.

You can express the above as a summation with a positive (but unknown) dv/dt and a canceling-out e if you think better in notation, but I can't figure out how to make that legible in a HN comment.

If you have any reason to believe that there is more downside risk than upside risk over the DCA period, then you should delay investing until that is no longer true, and go 100% at that time.

DCA is essentially the same intuitive leap as the Monty Hall problem, but backwards.

If you're committing to the strategy in advance, it delivers neither lower variance nor better risk-adjusted return.

> DCA takes a lot of that psychological pressure off...

Yes, that exactly. It's a psychological trick (if you have all the money upfront) and not a financially sound one.

If you commit to the strategy in advance, then you're picking an unknown price instead of a current price, and the unknown price is likely higher.

A financial hedge is, generally, something which reduces risk or improves on the risk:reward ratio in a mathematically demonstrable way. Generally this means bundling uncorrelated (or anticorrelated) assets. This concept won a Nobel for Econ in 1990(?), and is the foundation of modern portfolio theory.

Using "hedge" in a more colloquial way, it can mean "a way to protect yourself from an unexpected poor outcome". But by that definition this also fails, since you're just as vulnerable to outlier events, but the nature of those outlier events is different (and perhaps less intuitive).

It depends somewhat also on what you're DCAing into. If you're DCAing into a major index, there's essentially no chance of it going to zero (that's a society-ending event, hedge with farming equipment and doomsday prepping). And thus, no statistical or mathematical benefit to DCAing.

If you're expecting a non-continuous return function, such as a pending drug testing result or a major governments deal, then you're actively trading and a DCA strategy is almost certainly suboptimal.

It's very hard to construct a situation which is both plausible and favorable for DCA _if you have all the funds upfront_.

It may well seem to be de-risking, but mathematically it doesn't.

DCA'ing provides no mitigation of the risk of randomly timing the market poorly.

The only risk it mitigates is the risk of a sudden bankruptcy, or some other massive exogenous event which disrupts your future plans.

However even accounting for those events the expected value of DCA is still lower.

A single purchase at the weighted average price is the same as the DCA'd purchase. In both cases you buy X shares for Y$.

But it's not a hedge.

If you commit to the strategy (buy monthly for 10 months) then you're just choosing an unknown price over a known price.

And if you don't commit to the strategy, then you're actively trading and not DCA'ing.

Roku's best bull case (IMO) is as an acquisition. Which is not improbable!

And what if the prices go up during the 10 month period? You invested at a much higher price than needed.

The smoothing function of DCA will help mitigate FOMO and Buyer's Regret, but it won't (statistically) deliver higher returns.

> I guess he's betting on prices generally headed down over the next 10 months, so he significantly underpays if things go per plan.

Yes, exactly that! And if one is betting on prices generally going down over the next 10 months one should just not enter the market at all.

Dollar-cost averaging is still timing the market, if you have the full amount up front. You're betting that your future weighted average is less than the current price, that's timing.

There is absolutely expert consensus (among quants) that DCA _if you have the full lump sum up-front_ makes no sense. It's math.

> DCA makes mathematical sense anytime you have a long-term bullish thesis (otherwise, "do not invest" is a better strategy), but have a belief that there is a short-term noise function...

Math citation needed - the noise function you're hypothesizing could just as easily drive the average up as down, unless you have a reason to think it should go down, in which case you're timing the market and there's a better future time to go 100%.