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Ryan Singer

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2025-03-30
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2025-03-30
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  1. “That makes sense. And now you're going to have freedom to figure out how to actually make this a reality. There's going to be a million things to solve in the implementation detail. And now you have a bunch of fun problems and you don't have to keep asking questions to other people to understand what this is or how do I make a trade-off or that kind of a thing.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “From a functionality standpoint, from a technical standpoint, doable and desirable, something that we can make happen in that amount of time, then we can give it to a team, and we don't have to do the sometimes called Scrum, the paper shredder. That's where you take an idea and then you split it into 100 tickets, and you hope that it all glues together still after you've done that step, you know, we don't want to do that. Instead, we want to have a whole idea give it to a team so they see the whole, they really understand it, right? And then they can come up with their tasks and they can figure out how to track that and break it into pieces so they can actually take more responsibility. And so what we see is way more engagement, you know, especially from the technical team, right? Because instead of like, here's your ticket, right? Or here's your user story, it's like, here's the thing you understand.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “So, this is those creative sessions that I was talking about where we're jumping all over the room in front of the whiteboard and getting to an idea. And there the really key thing is that we're getting to an idea where we can see the idea. You know, we understand why we're doing this. We're wrestling with the problem and we're wrestling with the solution until we have an idea that we can actually say this is what we want to go build. So it's not just calendar or dashboard or newsletter builder, but it's like this idea of how we're going to tackle this problem about the calendar request, right? So that's the shaping. And then the third piece is when we've actually carved out a fixed amount of time, when we've shaped a solution that is from an experienced standpoint,”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “How do we actually take this fixed amount of time that we've given ourselves and vary the scope? How do we come up with Idea, some version of this that's going to work in the amount of time that the business is interested in spending.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “So that's kind of the first piece working backward from the amount of time we actually want to spend on something and say, what can we do? What could we shape so that after that amount of time we've gotten to somewhere we want to be? You know, it's kind of like if you're going to buy a car or you're going to buy a house or you're going to rent a new flat or whatever, you have to have like a budget in mind, right? And the budget then is how you choose between all kinds of alternatives and make a lot of hard choices and trade-offs to figure out like, well, you know, I want the faster engine, you know, but I can't afford, but I have to give this up or, you know, I want it to be fun to drive, but we also need space for longer road trips. And, you know, you're making all these trade-offs, right? So this is kind of this second piece is this work that we call shaping. And the shaping work is...”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Basically, kind of like three, maybe big things. So the first thing is this notion of we are not going to start something unless we can see the end from the beginning. So we're not going to take a big concept and then say, what's the estimate for this thing? We're not going to say, oh, we need to build a calendar and then do a whole bunch of Figma files or write a whole bunch of requirements and then ask for an estimate. We're going to go the other way around and we're going to say, what is our appetite for this? What is the maximum amount of time we're willing to go before we actually finish something? And we have that startup moment that we talked about, that moment of like, ah, you know what I mean? It works. We got somewhere. At least this, if not the whole project, this meaningful piece we can literally walk away from. So then what we found was that there was a lot of experimentation. We found that six weeks is kind of the maximum that we could see into the future where we could actually say like, how do we work backward and figure out something we could build in that six weeks and really land it?”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “When we have as we're asking, and what we're starting to realize is like, oh, this is not only is this not going to ship, but we can't even see the end of this, you know. And that was like one of those moments where you're like, oh, this isn't going to automatically organically just keep spreading as we hire forever. You know what I mean? We did reach a point where it's like, oh, we're going to have to figure out when this goes well. Why does it go well and what do we do differently and how do we kind of formalize that? So it's reproducible as we keep onboarding more people. And that's actually when shape up as a framework started. That's when I really kind of started to lean in and I sort of took over that responsibility of, okay, how do I systematize this?”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “I mean, really, it was, I mean, of course, there were always ups and downs, but it was about 10 years later when we had the first project. I mean, I remember the project. I remember being at the end of it was at that time already kind of, it was maybe it had been like maybe six weeks or seven weeks. We hadn't yet completely locked the six-week thing that went into shape up. And I remember we had a review session and there was a fairly new person who was leading, who was doing half of the work on that team. Had the review session, and it was like instead of, oh, look, this is about ready to ship, it was like there are a lot of open questions here. And not only are there a lot of open questions here. We're not getting quick answers”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “That's exactly what kind of became shape up was how do we hold on to that as much as possible? I mean, one big ingredient, we had an advantage also, which was that Jason and David hired so deliberately slowly. And this is kind of like a fortunate side effect of the fact that they didn't take investment money. So there was kind of, there was never that moment of like, now's the moment when we grow. It was always like one person. And then kind of the organism adapts. One more person, you know? And so this natural way of working, it was organically spreading, there were, I think, maybe 10 years before we had the first kind of like, wait a minute, what just happened? Like that's not, like, that project didn't go well. That's not how things normally run.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “Making a beautiful figmophile to represent a concept that could maybe be a feature, you know, it was this like super intense, really exciting collaborative, like, what about this? What about that? Oh, maybe this, you know. So that was a really big part of how we worked also. Very intensely collaborative sessions to figure out what the idea is and getting it sharp enough and crispy enough that we could very confidently get a yes from David and that he would know exactly what it is and what it means and come back and it would be what we pictured and it would work the way that we hoped so that we would kind of keep going and we wouldn't have to reverse or go back to the drawing board.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “They were these short, very, very intense sessions where you're trying to crack the nut together. Like, where's the idea? What's the concept? Like how can we go, what's this thing that we're going to go and like 10 hours later? Right. David's going to come back and we're going to be like, this is awesome. This thing works and it does something we're excited about, right? That was really kind of the seedling. I mean, actually that continued over years and years and years, those sessions. That's the seedling of this word in the book shaping. What does it mean to do shaping? It wasn't sitting alone writing a document. It wasn't...”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Yeah, I mean, the other big piece of it was so Jason and I were like this kind of product. What do you call it? Like the two thirds, you know, and then there was, so I was doing UX at the time, and I was doing hands-on coding as well. So we're very, very integrated. Everybody kind of does a little bit of everything. All of us were coding. Like Jason was in the actual app templates as well, doing HTML and CSS to do the views. He's doing hands-on design. We're all very much connected with why are we building this? What is this? You know, David's doing the bulk of the programming. Jason and I were having these little sessions, these little sessions where we would really figure out what the idea was. And there would be this moment where you would have a few strokes of the Sharpie pen on a big pad of paper. And all of a sudden you'd be like, oh, yeah, like that's the idea. That's the thing we want to go try to build. And for me, like those sessions with Jason.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “Totally, totally. And that's why where I come back to you is the part of the story where I think so many companies would say, yeah, I know that experience, right? Because they think that's probably the seedling of a lot, as you said, of successful companies is that combination of urgency and also that those guys were so talented and that they had a clear vision of what they wanted to do and all of that is this amazing time actually these early days.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “Yeah, I mean, put that together. So David's constraint of 10 hours a week, and then Jason has this, I mean, I think many really successful founders and especially CEOs have this thing. It's like all they want to see is movement. You know what I mean? Like forward, forward, forward. So like, when do we get to see it? When do we get to try it? When do I get to put it into somebody's hands? So that combination, there was just so much urgency, even though there was no outside pressure. You know what I mean? It was completely just like, let's say, cultural energy of like, how do we kind of keep getting somewhere and getting to something that we can celebrate and get excited about?”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “I don't know what he was doing the rest of his time, you know. But he's always been like that. He's always doing something interesting. Like he's either racing or who knows what. You know what I mean? But all I knew was that we got 10 hours of that time.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “Well, Rails came out of the first, so he told Jason. Want to try building this in Ruby? And because before they had done some collaboration and David had done things in PHP before that, and he had this new idea he wanted to try Ruby, this language he fell in love with. And then the framework Ruby on Rails, he ended up releasing that after Basecamp was standing because it was kind of extracted from the things that were necessary to get V1 of Basecamp to stand up.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “The end soon. And on top of that, even when we were building V1, David wasn't actually full time as our only technical person. He was programming 10 hours a week. So we had this really intense pressure of like, how can we really use David's time well? You know, we don't want to ever kind of give something that this is the thing we want to build. And then it turns out not to be what we want. We have to throw it away and then come back again. Or, you know what I mean? Like those kind of bad cycles of waste.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “I think the way it's different starts with kind of how the way we were working was a little bit different. So I started working with Jason and David on the first version of Basecamp, you know, which was like the flagship product of 37 Signals back in 2003. And we were a team of three. And we were, I mean, I think it's for any really small team when you're just starting out, you don't need a process. You don't need a way of working. It just kind of happens organically because you're together. You don't have to explain it to other people. You know, it just kind of happens on its own, right? But there was always this really intense urgency from both Jason and David. Like, we've got to get to something we can ship. We have to finish this and move on. We have to get to something that's done. There was just no tolerance for kind of big things that got fuzzy and started to drag. There was always this sharpening to get to what is this thing really and when are we going to get to”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “Well, you know, my wife heard me saying the same thing over and over again on every phone call. And she's overhearing me. And she's like, you have to make a course. You have to do something. You always are saying the same thing. So then this led to this course that we made, which is called Shaping in Real Life. And, well, yeah, the idea is the real life part, right? How do I make this work if my designers don't code, if I have actually, it's very contentious to get engineering time. You know what I mean? When there's all these different pressures that Basecamp didn't have.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “Same time, there's also a lot of questions that are coming my way because honestly, there are so few teams that are structured just like Basecamp that there are a lot of gaps in the book of like, well, what about this and what about that? And how do we do that in our situation? So a lot of my focus today is actually kind of closing those gaps and helping people figure out how can I make this work for me or for our team.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “Well, I mean, that came as a surprise to me. I mean, when I wrote the book, I had. And I actually didn't even know the outside world. You know, I mean, it was Jason's idea to even write the book because he said, look, a lot of people are going to want to know about this. A lot of people are struggling. And I'm kind of like, well, okay, I knew our inside story of we had some growing pains and we had to be able to formalize the way that we were working in shipping so that as we brought new people in that they could participate in that and we could stay fast. So I knew our like internal struggles and I honestly didn't know anything about the outside world. And it was only after the book came out that it gave me this kind of excuse to start talking to people from all kinds of different companies. And it's been really interesting. There are some really amazing cases of companies of very different characteristics from Basecamp, like VC fundedly bigger, like very different pressures, different team structure, different skills who are doing it. And at the same time,”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “One of the things I've been hearing, it's like I hear, oh, we thought there was only Scrum or Kanban, and then we heard there was the Shape Up thing. Like, what's that?”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “Yeah, that's great. Yeah, because it's so hard to get to that, right? And it's not all just this golden path rosy where we're all shipping beautiful, meaningful things all day. It's a hard business. There's no perfect school either that kind of produces expert product managers and CPOs and CTOs and stuff like that. So we're all trying to figure this out and we don't have a lot of sources, you know. So there is a lot of struggle.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “It came out, I even tried to have an online forum to get everyone who's interested to talk together. And what I started to learn pretty early on is that people don't like to talk about their struggles shipping, especially CPOs and CTOs don't like to go in a public forum and say our company isn't shipping or our engineering team is stuck or our team is always lost in the weeds, you know. That's not an easy community topic on an online forum, you know? So I think there's also some reasons why it's been word of mouth kind of slowly gathering steam”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “Yeah, I think it's interesting that we're talking now. You know, I mean, the book came out in 2019. And it's just, I've been hearing more and more, like, oh, we know somebody who's trying it or we're hearing it when we go talk to other companies. So I think it's a wave that's slowly building. And it's funny, you know, like.”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “I often use this analogy of like if you're doing a home renovation, you can have the most beautiful rendering of the new bedroom and we're going to have these lamps on the side of the bed that are coming out from the wall. But if you haven't checked, if there's electricity in that wall there or not, it's going to drastically change the cost and the time and everything. What we need to do in a shaping session is we come out with some kind of diagram where engineers, product and design, they're saying we understand that. So the first thing is we are not going to start something unless we can see the end from the beginning. We're not going to take a big concept and then say, what's the estimate for this thing? We're going to go the other way around and we're going to say, what is the maximum amount of time we're willing to go before we actually finish something? How do we come up with an idea that's going to work in the amount of time that the business is interested in spending?”

    2025-03-30 · Lenny's Podcast · A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals) · IDENTIFIED FROM THE TRANSCRIPT · source