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Ryan Singer is one of the earliest employees and the former Head of Strategy at 37signals (the makers of Basecamp), where he spent nearly two decades refining a product development approach that helped the company build super-successful products with small teams. Based on these lessons, he wrote "Shape Up: Stop Running in Circles and Ship Work that Matters," and Ryan now works with companies of all sizes to help them escape the cycle of endless sprints, missed deadlines, and dragging projects.

What you’ll learn:

1. Why traditional Agile and Scrum methods often lead teams into endless cycles of work without meaningful shipping milestones.

2. The “appetite-driven” approach to product development where teams set fixed timeboxes (usually six weeks maximum) and vary the scope instead of expanding timelines.

3. The exact process for running effective “shaping” sessions that collaboratively define projects before committing resources.

4. Why most teams struggle with too little detail in their planning, not too much.

5. Why a 30-to-50-person team size is the critical breaking point when growing startups need to adopt more structured processes.

6. Practical techniques for bridging the engineering-design divide by bringing technical and product perspectives together earlier in the process.

7. The powerful “breadboarding” and “fat marker sketching” techniques that help teams align on solutions without getting lost in high-fidelity details.

8. The clear warning signs that your current development process is failing before it’s too late to change course.

9. Proven strategies to implement Shape Up methods, whether you’re working in a startup or enterprise environment.

10. A step-by-step approach to transitioning from Scrum to Shape Up by piloting the methodology with a single team before broader implementation.

11. Why the PM role shifts upstream in Shape Up, focusing more on problem definition than project management.

12. How to adapt Shape Up principles to your company’s unique context, even if it’s nothing like Basecamp.

Some takeaways:

1. Stop asking “How long will this take?” and start with “How much time is this worth?” Let your time budget drive scope decisions, not the other way around.

2. Invest time in collaborative “shaping sessions” with product, design, and engineering together to define solutions that are technically feasible before committing resources.

3. Work in six-week cycles (or less), as the maximum time frame in which you can effectively see into the future and deliver meaningful results.

4. If a project won’t ship in the allocated time, don’t extend—bring it back to shaping rather than continuing to invest in something you don’t fully understand.

5. Stop breaking projects into tiny tickets created by someone who doesn’t understand the implementation—give teams the whole picture so they own the solution.

6. After project kickoff, have the build team identify just nine major implementation chunks—if they can’t fit the work into nine boxes, it’s not shaped well enough.

7. Shape Up provides the most value when companies reach 30 to 50 people in product and engineering, especially when the founders can no longer be directly involved in everything.

8. The method helps preserve the urgency and clarity of startup-style development while accommodating growth, maintaining a meaningful shipping cadence as teams expand.

Where to find Ryan Singer:

• X: https://x.com/rjs

• LinkedIn: https://www.linkedin.com/in/feltpresence/

• Website: https://www.ryansinger.co/

• Course: https://www.ryansinger.co/srl/

In this episode, we cover:

(00:00) Ryan’s background

(04:38) The origins of Shape Up

(07:40) Implementing Shape Up in different companies

(09:56) How Shape Up is different

(19:02) The core elements of Shape Up

(26:29) Shaping sessions and timeboxing

(37:23) Flexible sprint planning

(38:56) The output of a shaping session

(46:57) Balancing detail and flexibility

(53:50) A deep dive into shaping sessions

(01:01:32) Fat marker sketches

(01:02:48) Getting started using Shape Up

(01:13:20) Signs it's time to try the Shape Up method

(01:18:25) Feature factories

(01:25:59) The role of the PM in Shape Up

(01:28:26) What makes Basecamp unique

(01:35:55) The second edition of the book

(01:38:30) Linking product strategy and shaping

(01:41:53) Conclusion and final thoughts

Referenced:

• Basecamp: https://basecamp.com/

• David Heinemeier Hansson on LinkedIn: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/

• Jason Fried on LinkedIn: https://www.linkedin.com/in/jason-fried/

• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking

• Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/

• Intercom: https://www.intercom.com/

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of “Job Moves”): https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta

• Scrum: https://www.scrum.org/

• 37signals: https://37signals.com/

• Jobs to Be Done Theory: https://www.christenseninstitute.org/theory/jobs-to-be-done/

Recommended books:

• Shape Up: Stop Running in Circles and Ship Work That Matters: https://basecamp.com/shapeup

• Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress: https://www.amazon.com/Demand-Side-Sales-101-Customers-Progress/dp/1544509987/

• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612/

• Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.