Head of Engineering @ Railway. Prev. Epic Games, GitHub, Heroku, 37signals. Father of 4.
Apex, NC
Joined November 2007
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There's technical debt, then there's technical subprime mortgages with exploding balloon payments.
Apple should buy Superlogical and put them in charge of software.
Siri is still bad, like really really bad. I opened an email with my Uber Eats confirmation, there was a live activity on the screen with progress, and I pulled down and asked Siri "what did I order for lunch?" And it thought for like 2 minutes and then said it doesn't know. 🤦♂️
Okay so the harness and models are clearly bad. Well, then next I opened up the Siri GUI app on macOS and HOLY. It's the worst looking, beginner, basic bitch app I've ever seen. Did someone spend more than 5 minutes on this?
Whoever worked on this app along with the full chain of people who checked off on this needs to be terminated immediately. This is 0/10 terrible software, so embarrassed for Apple to ship this.
Sales email: We’re excited to once again be heading to AWS re:Invent in Las Vegas ...
Me: That's weird, I'm excited for exactly the opposite reason.
Mark Imbriaco retweeted
Railway started the year at $20M ARR. It’s now ~$100M. Solo founder. Fully remote. Only ~40 people.
The one trait that explains why Railway is breaking all the rules:
“It’s almost like cheating on your homework when you go and look at somebody else’s solution. If this is how Stripe does this or this is how Cursor does this, I don’t want to hear about it.”
Jake Cooper (@justjake). Founder and CEO of @Railway.
Knuckle Up ↓
--
In this conversation with Jake Cooper:
00:00 Who is Jake Cooper?
02:54 How did Railway survive losing $500K a month?
06:01 What made Railway’s growth chart go vertical?
09:45 Why won’t Jake look at how other companies solve problems?
14:34 Is two the worst number of co-founders?
20:04 How does a 40-person team hit $100M in ARR?
22:41 Why does Railway say no to 90% of ideas?
28:55 How do you compete for talent against the AI labs?
32:25 What does a technical interview look like after Opus 4.5?
35:34 Trust, clarity, judgment: how does Railway’s six-week onboarding work?
44:59 What does HARD stand for, and which value costs the most?
48:49 Why does Jake go dark from Friday night to Sunday?
54:54 What breaks first in a world with 10,000x more software?
59:49 Where does Railway play in two years?
1:01:37 How has Jake had to grow as a CEO?
1:09:29 Is burnout just an input-output mismatch?
1:12:27 Why does Jake think most startup advice is overrated?
Anyone who says anything other than "better late than never" about this is ngmi
I took this week off work to celebrate my 30th anniversary. Deleted Discord last Friday, have mostly ignored X except for hockey content, and have had a great week.
Next week I get to catch up on the 5 years of advancement that I assume happened this week.
Mark Imbriaco retweeted
When a nerd tells me they don't use agents "because I can write better code than any agent", I usually go "huh, sure buddy, you do you". When they tell they don't use agents for monitoring, I just laugh in their face.
Seriously. You can't monitor a production deploy better than an agent can. I dunno about AGI but this specific job is something that an LLM can already do better than every single human in the world. For me, as a systems engineer, having agents monitor my infra changes has been (no joke) more impactful in my day-to-day work than having agents write my code.
I started doing this many months ago by asking the agent to monitor explicitly after I triggered a deploy; soon after I moved to using a set of my own Skills. Now our Review Agents team has fully automated this workflow with delightful UX and obviously I'm not going back.
It's hard to overstate how powerful this is. All it takes, for me, in production:
- The Datadog MCP
- The PlanetScale MCP (for all our databases)
- Our custom MCP for deploys and internal tooling
That's it. Some carefully designed gradual deploy pipelines, and the agent just takes care of everything from there. You can't really deploy SEVs to production anymore.
Doing infra like this is pure joy. And the safety is just a tiny part of it. The Rollout agent also does the actually hard part of my job, which is _performance_.
When the changes you're deploying are a performance optimization, the agent prepares a monitoring plan that ensures the optimization is correct AND effective. I rarely prompt benchmarks for my optimizations anymore. Just fucking go to prod and the agent is gonna give me the best possible benchmark.
If you work on systems or infra for a living, you should be setting up your production environments so you can use Rollouts. Not doing so is actually reckless.
Mark Imbriaco retweeted
Wow, new model just dropped. Congrats on the new model. Looks like it scores higher on the benchmark than the old model. That’s good. The old model was state of the art but now it isn’t. That’s how it works. Can’t wait to see the next model, which will be bigger. I love the model business.
"Design a stand for my Logan Stankhoven autographed hockey puck. Use Blender."
Astra literally one shot this. Zero tweaks.
Dug out the old OG Dell XPS 13 Project Sputnik laptop that @barton808 hooked me up with way back when they came out.
Omarchy runs great, especially for a 2012 laptop.
It's me, I'm the 6 year old boy Rexy is marketed at. Mission accomplished @pjhyett.
