The Missing Part That Makes or Breaks Most Product Decisions

This conversation reveals why 6-week ideas often become 6-month nightmares. Beyond that, it clarifies how you can break free from that.

This podcast isn’t just an informal chat; it’s pure gold for you. If you truly care about driving value beyond deploying frameworks. You’ve got to listen to this episode.

Ryan isn’t going to sell Shape Up for you, or try beating Scrum to its knees. This is a lesson nobody is talking about, and it can transform how you work.

Before we jump into the podcast, let me share a personal story with you.

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Beyond Frameworks

Last year in Cologne, I met Ryan, who fundamentally changed my perspective on product development. He’s the author of Shape Up and a former Head of Strategy at 37signals. Now, with such baggage, you might be surprised by how generous he is with his time and ideas; he openly shared many insights with everyone around him throughout the entire conference.

I'd been following 37signals for years, watching with high interest as they built profitable products with tiny teams while the rest of us struggled with endless meetings and dragging projects.

Meeting Ryan in person confirmed what I suspected: their success wasn't luck. It was a system.

After our conversation for Untrapping Product Teams, I walked away with insights you can't find in any book or blog post. Ryan shared the real mechanics behind their approach, including parts of the framework that never made it into Shape Up because they were so automatic at 37signals, they didn't even realize they were doing them.

If you've ever wondered why your projects quickly become a drag, or why alignment feels impossible despite constant communication, this conversation will reshape how you think about product development.

It’s roughly 50 minutes. After you watch it, I promise you, your thinking will be different. Write your take in the comments.

Find more about Ryan:

* LinkedIn

* Website

* Shape Up

10 Game-Changing Insights from Ryan Singer

1. The Real Problem with Scrum

"Scrum is okay if you have a lot of kind of smaller pieces of well understood work, because it's a little bit like a sausage machine. But if what you're trying to do is new product, new features, meaningfully different functionality... then for those kind of things, you need to have a lot more alignment."

2. Why Your Projects Keep Expanding

"You can write a few bullet points and think that this is clear direction, but it's not clear enough. And then it can also happen that you have like whole bunch of Figma files up front. And of course they look beautiful, but then as soon as you start trying to really build them, then again, the questions appear."

3. The Hidden Step Before Shaping

Ryan revealed "framing" - the crucial step that's implicit in Shape Up but never named.

"When somebody says dashboard, can I turn that into this is what's going wrong today and this is why this is an opportunity and this is what we're going to try to fix."

4. How Many Big Bets Do You Really Get?

"How many six weeks do you get in a year? Not that many, right? That is a major expense. It's a major investment."

This simple math reframes everything about prioritization and founder involvement.

5. The PM Hiring Trap

"If you think that you're gonna hire a PM who's gonna answer that for you, that PM shouldn't be a PM. That PM should have a C in front of their title."

Ryan explains why founders can't delegate strategic decisions to PMs.

6. Why Bigger Impact Needs Bigger Alignment

"The bigger the impact, the more alignment we need. You don't need a lot of alignment to go solve a ticket that you can solve in two hours. But as soon as it becomes into, I need multiple people to all be working on the same thing... for a period of weeks... then I need to have a lot more alignment and clarity."

7. The Figma-First Problem

"We are seeing amazing results when we do High Fidelity last. Last."

Ryan argues that starting with wiring and interactions, rather than pixel-perfect designs, unlocks massive speed gains.

8. How to Stay Involved Without Micromanaging

"What you want is to be able to be more involved in very important moments and less involved in the details of execution... Can I be really involved for three hours and then not involved for three weeks?"

9. The Dashboard Revelation

Ryan shared a story where a "dashboard improvement" request actually revealed a critical problem with failed subscription payments.

"What started as Dashboard turned into fixing payment recovery for failed subscription payments."

10. Creating True Project Clarity

"If from a leadership standpoint, I don't feel that I can have a conversation about what is important to the business and then get alignment... and then in six weeks later, see that thing actually working. If I can't do that today, then what I need to do is find a solution."

This conversation went deep into territory that most product development discussions never touch.

Ryan didn't just explain what to do; he showed why most approaches fail and how to think differently about the entire product development process.

The full conversation uncovers how to implement these concepts in organizations of any size, why the "small team" criticism of Shape Up misses the point, and practical steps for moving from endless meetings to focused execution.

What resonated most with you? Reply and let me know which insight hit hardest.

Are You Ready to De-bullshitize the Product World?

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Talk soon,

David Pereira100X PM Mastermind

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