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Knuckle Up with Nakul · 3 min · Oct 13, 2026
Railway says no until the timing and need are clear
Jake Cooper
Founder & CEO, Railway

Nakul MandanHost · Host, Knuckle Up with Nakul
General partner at Audacious Ventures; his show goes deep with founder CEOs on how they build.
About this segment
Railway asks why an initiative matters now and scrutinizes proposals before quarterly planning. It starts new work manually, then builds systems once it understands the job.
From “How Railway says no to 90% of ideas and keeps winning | Jake Cooper (Founder, CEO)”, Oct 13, 2026. Watch the full episode
Thanks. We'll look at and fix what's off.
“The last line just says, why now? Like, why are we doing this now?”
Takeaways
- Every proposal ends with the question: why now?
- Repeated ideas can signal that the time has come to act.
- Do the work manually first to define the role and process.
In this episode
Full episode- 3:00Railway rebuilt its free tier around better infrastructure economics3:02
- 35:29Railway uses a six-week onboarding to build ownership7:02
22:30Railway says no until the timing and need are clear3:04
- 5 more moments in the full episode
Transcript
Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.
- 22:36
they're completely wrong or whatever. And so it's like just a lot of work, right? to like go in and get there, you know? When you say no to 90%, what makes the cut? What makes the cut? What's the hurdle that something has to clear for it to say, yeah, we are doing this. We are choosing to do this. Yeah, I think it has to be like almost the right time. I think like, you know, our founding marketer has this saying that I really like internally, which is disagreements of timing are my favorite to have because all disagreements are disagreements of timing.
- 23:02
And so if it's like, oh, why is it the right time for us to go in and do this? And so the way we do stuff internally is we like write a small abstract, right? And the last line in the abstract, right, you know, you've got a background, a little problem, you know, what problem are opportunities. The last line just says, why now? Like, why are we doing this now? Right. Like, you know, can it come slightly later?
- 23:20
Do we need to go in and do it now? Like all of those other things. Right. And then, you know, these things flow through like one channel where everybody kind of like watches them, et cetera. And then we plan quarterly into like going to roll them out. And those things end up, you know, like we talk about them. We spend an entire week like doing this planning thing, which is like crazy for like a, you know, early stage startup or like whatever.
- 23:39
But like we want to talk and we want to like, you know, scrutinize this thing and be like, hey, listen, should we do this now or should we do this later? You know, and so we just end up the default response to like say for a lot of these things is no, like we're just not going to go in and do that. Right. But then you hear the same thing again and again and again. Right. And like great ideas are inevitable.
- 23:57
You just can't escape them or whatever. Right. And so they will just keep coming up. Right. And then after a while, it's like we have to do this. We just have to do it. Right. Somebody gets fed up and they're like, we're doing this. Right. It's like, great. Awesome. So everything you just said, being very intentional on the initiatives, you take timing, everything. But is it also that you try to solve things more with systems and people?
- 24:16
Because, you know, like we work with so many companies and founders will feel like, hey, if we want to go down this initiative, we need this many people. Like you have one sales rep, one product marketer and two solutions engineer. Right. And a growth marketer. And then two DevRel folks. OK, so that's like a seven, eight people go to market team. Totally. 100%. The initiative is right, as in sales marketing needs to happen now at the company, but still it's lean.
- 24:42
So it's very lean. So is it a function of also like systems building that you've kind of incorporated at every aspect of the business? So I would say that like we don't want to do things manually. And so if we're doing something right, it should be like grit, process, repeat. Right. So start start by doing it manually. You have you actually have to do it manually initially just to like really understand what this thing is. Right. And even to this day for new roles, like we will ask that folks like go in and do this thing manually so that we know what we're going to go in and hire for. Right. We know what the jobs to be done are that like fit directly into that JD. And then we will go in and source specifically for those folks. And that's how we find exactly the right person for a lot of this stuff.
- 25:22
Is that part of your recruiting criteria that the person has to be a system sinker? Because often when execs join, and I don't know how big is your exec team,