39,339 karma · joined July 8, 2008
Chief Security Officer for Evertas Insurance -- the world's first cryptoasset insurance carrier. https://evertas.com/
Previously, CEO and Co-Founder of CryptoSeal (YC S11), which was sold to CloudFlare on 2 June 2014. CISO/Board Member of Tezos Foundation 2018-2020.
Previous startup founder (HavenCo, a couple ecash projects, distributed colo, and DoD/Iraq contracting, new thing), too. Deeply interested in computer security, infrastructure, security, conflict zones, and making the world a better place.
Aside from living on a Caribbean island during crypto export controlled 1990s, I've lived on a tiny artificial platform in the North Sea, plus more reasonable places like London, Amsterdam, Iraq, Afghanistan, Kuwait, and spent 6 months diving in Thailand.
"I, the greengrocer XY, live here and I know what I must do. I behave in the manner expected of me. I can be depended upon and am beyond reproach. I am obedient and therefore I have the right to be left in peace."
Email: ryan@venona.com (etc) Twitter: @octal https://twitter.com/octal LinkedIn: http://www.linkedin.com/in/ryanlackey
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80' is absolutely full time paid captain, full time paid mate (potentially engineering or water toy support), and a steward/also mate-when-needed. If it's being used fully, probably need 2-3 other crew for rotation, and potentially would go 3+1 for a heavily chartered 80'. The paid captain at 80' is not merely for driving the boat but also the management of staff, maintenance scheduling, charter management, etc.
80'/24m is also where the commercial regs come into play (which I'd probably be trying to meet anyway), and 80' cat is already going to have a hard time with marinas in a lot of places (due to being wide, as well as long), but due to solar + good watermatermakers + excellent tenders, could probably operate at anchor far more than otherwise.
I'd probably do the "Boat DAO" model with the 80' and have 4-6 rentable cabins (not true retail, but within friend network, etc, and more particular when I'm using it). This is the specific boat I want: https://sunreef-yachts.com/en/launched/sunreef-80-eco-141/ (although by the time I'm in a position to order, and wait 2-3 years for production, there may be something better, and I'm hoping Starlink, lithium-ion batteries, etc. continue to improve -- mainly from a cost and maintainability perspective.)
Part of my motivation is that some of my friends are doing a lot of Seasteading related stuff and I'd want a boat to be able to visit/stay during some of those events using fixed platforms.
Would probably run Caribbean (where I live) from mid-NOV to mid-MAY (hurricane season avoidance), and then summer in Med, for at least a year or two, then do 2-3 year RTW journey once or twice. My plan would be to personally occupy it ~3 months out of the year at least, and to be able to charter entire boat or individual cabins for enough to defray most of the operating costs if successful. Spending the next couple years getting familiar with sailing around the Caribbean as well as obviously earning more money to be able to afford this ($3-10mm capex, 10-20%/yr of that also total operating budget, although some fraction comes back as earnings). I think I could realistically crowdfund/investment contract ~50-75% of this as well if the business model works out, maybe through prepaid/discounted use. I might get a ~30' powerboat here in Puerto Rico since <41.5' can be lifted out of the water and put into a warehouse rack during hurricane season, and powerboats are far more useful for day and 1-3 day trips around here due to currents/winds. Something able to get to Vieques/Culebra/Culebrita and maybe to USVI or even BVI.
Once you have a large enough following for some reason (and ideally a fairly committed one; IDK if "follows someone on YouTube, like MrBeast" is enough -- has to be more like "my favorite musician/artist" or "business idol" or something), the rest is comparatively easy. You could pay people for all the stuff.
Basically the five routes today are: 1) Network State (stuff less than a state at start, ground up) 2) Negotiating with an existing state (free trade zone with more autonomy) 3) Seasteading (mostly an engineering and capital problem) 4) Space (also an engineering and capital problem) 5) Military conquest. Over the past ~70 years the last option didn't really exist, but increasingly it probably could work in some very specific locations, especially if you can find a fig leaf of "this local guy actually needs to be in power, not the guy in power now".
I've discovered I can tolerate almost any local conditions (tiny dorm room, Sealand, sleeping in a car, trailer in Iraq, tent in Afghanistan, random tiny apartment, hotel, airport lounge, 5 star hotel suite, villa, etc. are all not that different) as long as I have Internet.
I'm currently looking at getting a (50-80', solar, nice) sailing catamaran in a few years and doing RTW trips on it.
The new "network state" theories are a lot more interesting overall, though -- creating new groups of people FIRST, then building out progressively more solid physical infrastructure (potentially in different places), then networking them.
Crypto gets a few things really right, and can do some things which can't be done by tradfi, but has a huge number of problems which need to be solved (some are "open problems" which don't really have solutions yet; some are taking what the top 0.1% of people or what people do some amount less than 100% of the time and making it universal, which is mostly what I am doing now as CSO at a crypto insurance company.)
(My favorite rental car option of all time was Silvercar -- they had a fleet of identical Audi A4 sedans, no-hassle app based rental, good for the time prices ($50-60/day), and zero hassle overall. Something happened and they became audiondemand and became vastly more expensive, though.)
What I dislike is that it applies to all devices in your iCloud profile, and is overall pretty intrusive/annoying. Best practice if you're going to use it is probably to have multiple iCloud accounts (maybe in a "family" for license sharing), and Lockdown Mode one of them for the more secure devices. I tried using it for all of my devices last year and it was pretty unusable.
(Main pain point was how it handles unsecure wifi networks; I consider ~all networks insecure regardless of wifi encryption, but not being able to save or otherwise autoconnect to a hotel network with an iPad with nothing on it, etc. was the last straw. With a decent travel router it's fine.)
Any of the big company "frequent renter" programs, like National Emerald Aisle/Executive, Hertz #1, etc., gives all the stuff you want. Usually I'm at airport locations (which do have extra taxes/fees), but it's "walk up to car, walk around one time just to make sure there's nothing obviously wrong, get in, adjust mirrors, configure usbc/carplay, stop at booth where they take my drivers license and credit card, drive off". With National I get my pick of any car on the lot (and with a corp discount code, usually around $30-40/day all-in).
The local branches suck a little more due to limited selection and lack of cannelized check out, but they're pretty close. Also way worse at most non-US locations (with the exception of big gateway airports).
I've returned cars and aside from one time where I drove over a concrete curb at CDG which I couldn't see (sigh, at the airport itself, returning the car), and had to pay for damages, it's always been painless. One time I returned a car where thieves at Stanford had broken the rear glass, and at SFO they just said "oh, another one", and checked a box on the return form; everything was handled via email after that.
There are also day-rate car rentals through Uber and some other programs like that where you use an app, find car, and drive off.
I would have no problem relying on rental for the last 5% of car needs (e.g. if I had a 2 seater or something, or didn't want to get snow tires to go into the mountains, etc. The "get to the rental location" is the biggest friction, and in true emergency cases where I absolutely need a car right then, which is why I usually rent for the whole trip.
I am going to try to buy a house in 2024-2026 so I can have a charging spot/garage so I can buy the EV, although not in a huge rush given the local real estate market (Puerto Rico), hassle of moving, etc (and relatively few miles/yr on my present car, although it's a 2006 and gets about 10-12mpg).
I wonder how many people are in similar situations. A PHEV would actually be the optimal new vehicle for me -- no need to charge, exempt from 40% import duty, and highly efficient in stop and go traffic -- but I want the Tesla. (I've also never owned a new vehicle, and kind of enjoy owning an old/cheap enough truck that if anything happened to it I'd be relatively unconcerned.)
If it's old or minor, I don't think I'd care as a hiring manager. It's annoying in some regulated industries since felony complicates checkbox compliance, but in "normal" industries enh.
This is one of the few things cryptocurrency gets right in one specific way better than most other applications -- in most cases, everything is explicitly about operations with a key, and you build up protections on both sides of that. Unfortunately those protections themselves are often inadequate (hence billions of dollars in losses), but it's at least conceptually simpler and potentially could be fixed.
Passwords are "legacy" security technology at this point (in the sense of being outdated and bordering on obsolete, and yet still needing to be supported) -- password managers are tools to manage that legacy technology.
There are ways to set passkeys as non-exportable from device I think but that is not the default.
But overall -- I work for an insurer. Having to document how something was done a year+ after it was done to convince auditors/insurers/large clients is a LOT easier if you can point to a specific piece of hardware vs. a bespoke process. The downside of not having tamper-evidence or tamper-response (ideally) at the hw level is you need to build a lot of other controls around it, and that is expensive, impractical, and difficult to document in a lot of environments. e.g. in a datacenter it's unlikely you can enforce "two man from security/senior executive team in the cage"; it's probably going to be (at best) two ops staff, often contractors, and two-man rule isn't actually that widely used outside CAs themselves. The use cases I'd like for this are application logic, not traditional CAs (who do need FIPS). Add to this lifecycle management of the hardware from production to pickup/delivery to provisioning, pre-deployment storage, deployment, operation, routine audit, replacement, audit, and decommissioning, and it's way easier to put protection into the module. Most of the time I've just seen hardware protection inherited from single-chip vs. module-level protection created, but if there's no certified IC available, module protection it is.
Actual FIPS certification would be nice (or a better standard), but challenging in deployment because almost every vendor FIPS certifies with a specific application load and as soon as you run custom applications (which is badly supported in the HSM world), you lose certification anyway. "FIPS rated hardware running a non-FIPS load, audited in appendix A" is insurable, but ideally there would be something better. 99+% of HSM deployments are just used as dumb key signers which are trivially exploitable when you pop the host, though, so I'd certainly take the non-FIPS option.
(Today, the state of the art is pretty much SGX or another TEE on the host running custom application logic to evaluate and instruct signing which talks to the FIPS HSM to do key control and actual signing, e.g. what Anchorage does.)
This is competing with $5-30K HSMs as well as $30-400 "hardware wallets" or second factor keys, as well as (free) embedded secure enclaves.
A screen and 2-3 buttons would be nice, though; also a tamper-evident/tamper-responding package. But my main desired use case for this is a lightweight app-specific HSM so I'd just need to validate integrity of device before connecting it to host. USB Armory II is the main alternative.
Obviously can prototype without this functionality, and can build out the toolchain/etc. I'm a lot more excited about Tropic Square than most alternatives, but this is shipping now.