Readit NewsAt 10:25am ET, HN is more up-to-date than Wikipedia (article hasn't been updated yet to reflect his passing).
kenrose commented on Self-hosting a NAT Gateway awsistoohard.com/blog/sel... · Posted by u/veryrealsid
We did this at OpsLevel a few years back. Went from AWS managed NAT gateway to fck-nat (Option 1 in the article).
It’s a (small) moving part we now have to maintain. But it’s very much worth the massive cost savings in NATGateway-Bytes.
A big part of OpsLevel is we receive all kinds of event and payload data from prod systems, so as we grew, so did our network costs. fck-nat turned that growing variable cost into an adorably small fixed one.
When mosh came out back in 2013, it solved a pretty real problem of ssh crapping out when you changed networks (like moving from in-office to home). It solves it at the app layer and uses UDP and is designed to work in high loss / latency environments. Very cool.
At the same time, in recent years, I've found that ssh running on top of Wireguard / Tailscale is way more usable than 2013 days. Those latter tools address the roaming IP issues directly at the network layer.
So while there are still issues with ssh / TCP if you're on a really crappy network (heavy packet loss, satellite link, etc), those have been less common in my experience compared to IP changes.
The “killer use case” for Mosh feels a lot less killer now.
kenrose commented on Tailscale has raised $160M tailscale.com/blog/series... · Posted by u/louis-paul
> but it may mean building new standards on top of the duct-taped 1980s-era networking stack the modern Internet still runs on.
That’s a path directly into a money burning machine that goes nowhere. This has been tried so many times by far larger companies, academics, and research labs but it never works (see all proposals for things like content address networking, etc). You either get zero adoption or you just run it on IPv4/6 anyway and you give up most of the problems.
IPv6 is still struggling to kill IPv4 20 years after support existing in operating systems and routers. That’s a protocol with a clear upside, somewhat socket compatible, and was backed by the IETF and hundreds of networking companies.
But even today it’s struggling and no company got rich on IPv6.
Totally fair to bring up IPv6 vs. IPv4. However, I think Tailscale’s approach might sidestep some of that pain.
Avery (Tailscale CEO) has actually written about IPv6 in the past:
- https://apenwarr.ca/log/20170810 (2017)
- https://tailscale.com/blog/two-internets-both-flakey (2020)
Tailscale, on the other hand, doesn’t need to wait for the Internet to upgrade. Their model sits on top of the existing stack, works through NATs, and focuses on "identity-first networking". They could evolve at the transport or app layer rather than rip and replacing at the network layer. That gives them way more flexibility to innovate without requiring global consensus.
Again, I don’t know what their specific plans are, but if they’re chasing something at that layer, it’s not crazy to think of it more like building a new abstraction on top of TCP/IP vs. trying to replace it.
kenrose commented on Tailscale has raised $160M tailscale.com/blog/series... · Posted by u/louis-paul
kenrose commented on Tailscale has raised $160M tailscale.com/blog/series... · Posted by u/louis-paul
Hm OK well thinking out loud, $100M / 3 is $33M / year?
I don't know much about Tailscale, nor about how much it costs to run a company, but I thought it was mostly a software company?
I would imagine that salaries are the main cost, and revenue could cover salaries? (seems like they have a solid model - https://tailscale.com/pricing)
I'm sure they have some cloud fees, but I thought it was mostly "control plane" and not data plane, so it should be cheap?
I could be massively misunderstanding what Tailscale is ...
Did the product change a lot in the last 3 years?
You're not wrong to think Tailscale is primarily a software company, and yes, salaries are a big part of any software company's costs. But it's definitely more complex than just payroll.
A few other things:
1. Go-to-market costs
Even with Tailscale's amazing product-led growth, you eventually hit a ceiling. Scaling into enterprise means real sales and marketing spend—think field sales, events, paid acquisition, content, partnerships, etc. These aren't trivial line items.
2. Enterprise sales motion
Selling to large orgs is a different beast. Longer cycles, custom security reviews, procurement bureaucracy... it all requires dedicated teams. Those teams cost money and take time to ramp.
3. Product and infra
Though Tailscale uses a control-plane-only model (which helps with infra cost), there's still significant R&D investment. As the product footprint grows (ACLs, policy routing, audit logging, device management), you need more engineers, PMs, designers, QA, support. Growth adds complexity.
4. Strategic bets
Companies at this stage often use capital to fund moonshots (like rethinking what secure networking looks like when identity is the core primitive instead of IP addresses). I don't know how they're thinking about it, but it may mean building new standards on top of the duct-taped 1980s-era networking stack the modern Internet still runs on. It's not just product evolution, it's protocol-level reinvention. That kind of standardization and stewardship takes a lot of time and a lot of dollars.
$160M is a big number. But scaling a category-defining infrastructure company isn't cheap and it's about more than just paying engineers.
kenrose commented on Ask HN: Would you still choose Ruby on Rails for a startup in 2025? · Posted by u/dondraper36
I’m the CTO at OpsLevel, where we’ve been running a Rails monolith for ~6 years. We started on Rails 5, upgraded to 7, and are currently moving to 8. Before this, I worked on Rails at PagerDuty (including splitting a monolith into microservices) and on Shopify’s “majestic” monolith.
The best thing about Rails is its strong, opinionated defaults for building web applications. It handles HTTP request routing, data marshalling, SQL interactions, authentication/authorization, database migrations, job processing, and more. That means you can focus on business logic instead of wiring up the basics.
Rails isn’t as fast or lightweight as Go, but they solve different problems. For most web apps, the bottleneck is I/O, not CPU. Rails optimizes for developer productivity, not raw performance, and that tradeoff is often worth it, especially when speed of iteration matters more than squeezing out every last cycle.
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