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Lenny's Podcast / episode intelligence

A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)

30 Mar 2025 20 published claims 2 attributable people
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Speakers in the public record

Ryan SingerLenny Rachitsky

Claim mix

recommendation 6belief 6evaluation 3commitment 2prediction 1observation 1preference 1

Evidence policy

Every row below preserves an exact excerpt. Identified speakers are linked; unresolved voices are labeled and excluded from people counts.

Claim ledger

The useful parts, with receipts.

20 published records

01 / recommendation

Recommends Demand-Side Sales 101.

“Actually, the one that I recommend the most is Demand-Side Sales 101 and it's funny because it's like sales. Especially for a product person, you're like, "I'm the product person, not the sales person." But it's such a good dive into, "What are people really trying to solve?" And getting into that mindset of, "What's the struggle? What's the problem?" I think that's a really good entry point for that.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

02 / belief

Where is really the place, the itch they're trying to scratch? And then, a lot of the Shape Up stuff is kind of when I have something where I think there's an opportunity or I think there's something meaningful there because of what we learned from customers or the job to be done, research, or whatever it was.

“Where is really the place, the itch they're trying to scratch? And then, a lot of the Shape Up stuff is kind of when I have something where I think there's an opportunity or I think there's something meaningful there because of what we learned from customers or the job to be done, research, or whatever it was.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

04 / prediction

There's just so many elements of this that just connect with the way humans work versus the theory of just like, "Yeah. Well, let's see how long this will take.

“There's just so many elements of this that just connect with the way humans work versus the theory of just like, "Yeah. Well, let's see how long this will take.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

05 / belief

What's interesting about it is that it's very, very pointy for like if you are trying to make progress on sales, then it's this other kind of sales, this demand side sales. So I think maybe it's more for us who are kind of using it for different purposes.

“What's interesting about it is that it's very, very pointy for like if you are trying to make progress on sales, then it's this other kind of sales, this demand side sales. So I think maybe it's more for us who are kind of using it for different purposes.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

07 / belief

I've had a lot of that. I think that your intuition is right. That the market for the last category is the biggest, but it's hard to reach them.

“I've had a lot of that. I think that your intuition is right. That the market for the last category is the biggest, but it's hard to reach them.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

08 / observation

The question is what problem are we trying to solve, because the shaping work is more what are our options for the solution? And if the problem is too fuzzy and big, if the problem is just calendar, then the shaping is going to be this ever-expanding, never-ending thing, and we're not going to be able to get anywhere.

“The question is what problem are we trying to solve, because the shaping work is more what are our options for the solution? And if the problem is too fuzzy and big, if the problem is just calendar, then the shaping is going to be this ever-expanding, never-ending thing, and we're not going to be able to get anywhere.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

09 / belief

I think what we see today, out of necessity in a lot of teams, is that the PMs spend a lot of time chasing around inside of the build phase, inside the time box, to try and make sure that people aren't stuck and getting lost in the weeds and try and keep things moving.

“I think what we see today, out of necessity in a lot of teams, is that the PMs spend a lot of time chasing around inside of the build phase, inside the time box, to try and make sure that people aren't stuck and getting lost in the weeds and try and keep things moving.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

10 / belief

If we're going to commit engineering time and it's like we believe there's some way to see empty spaces, but the way is a question mark, it's a really risky way to spend that time.

“If we're going to commit engineering time and it's like we believe there's some way to see empty spaces, but the way is a question mark, it's a really risky way to spend that time.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

12 / evaluation

There's a reality check that happens there and very often, there's a back to the drawing board. So, when there's a lot of solutioning all the way down to detail without engineering involved, usually, that's a painful recipe and then it's like, "No, we can't do that," or, "Actually, it doesn't work like that.

“There's a reality check that happens there and very often, there's a back to the drawing board. So, when there's a lot of solutioning all the way down to detail without engineering involved, usually, that's a painful recipe and then it's like, "No, we can't do that," or, "Actually, it doesn't work like that.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

13 / recommendation

We've even already churned through a new head of product, or we've got a different CTO in and we're still having the same problems, then there comes a point where it's like, I know that this is uncomfortable, and I don't know somebody who's done it, but I think we need to try something different because we can't continue this way.

“We've even already churned through a new head of product, or we've got a different CTO in and we're still having the same problems, then there comes a point where it's like, I know that this is uncomfortable, and I don't know somebody who's done it, but I think we need to try something different because we can't continue this way.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

15 / preference

Because I think I'll quote Bob Moesta, who's been on your show a couple times, "You can't put 10 pounds of crap in a five pound bag.

“Because I think I'll quote Bob Moesta, who's been on your show a couple times, "You can't put 10 pounds of crap in a five pound bag.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

16 / recommendation

There are so many unknowns, there are so many ticking time bombs of things that we didn't understand or couldn't foresee, but if we set a ceiling at six weeks, we have a much better chance of, I think that's the size of something where we can actually shape it and surface enough unknowns and reveal that complexity before we're in the middle of it.

“There are so many unknowns, there are so many ticking time bombs of things that we didn't understand or couldn't foresee, but if we set a ceiling at six weeks, we have a much better chance of, I think that's the size of something where we can actually shape it and surface enough unknowns and reveal that complexity before we're in the middle of it.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

17 / evaluation

I think the way it's different starts with 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, which was the flagship product of 37signals back in 2003.

“I think the way it's different starts with 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, which was the flagship product of 37signals back in 2003.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

18 / evaluation

Or the product person is going to be looking in and saying, "I get that that's really an easy way to do it technically, but I don't think that we're actually delivering the value if I play through the customer scenario here.

“Or the product person is going to be looking in and saying, "I get that that's really an easy way to do it technically, but I don't think that we're actually delivering the value if I play through the customer scenario here.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

19 / recommendation

" Or it's also a good moment where somebody who's more junior might describe their implementation approach, and then someone who's senior can review that and say, "Actually, we've done that before, and we'll run into this trouble if we don't use this other thing.

“" Or it's also a good moment where somebody who's more junior might describe their implementation approach, and then someone who's senior can review that and say, "Actually, we've done that before, and we'll run into this trouble if we don't use this other thing.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast

20 / recommendation

You bring that person together with the product person who deeply understands the backstory of why this is an opportunity and what we're trying to solve with this. And then a designer in the room and they're whiteboarding and wrestling with each other to get to what's a version of this thing that we believe in that's real that we can actually finish in that time.

“You bring that person together with the product person who deeply understands the backstory of why this is an opportunity and what we're trying to solve with this. And then a designer in the room and they're whiteboarding and wrestling with each other to get to what's a version of this thing that we believe in that's real that we can actually finish in that time.”
Speaker
Ryan Singer
Publisher
Lenny's Podcast
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