Lenny's Podcast: Product | Growth | Career

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

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Mar 30, 2025

Ryan Singer, former Head of Strategy at 37signals and author of "Shape Up," shares his innovative approach to product development. He critiques traditional Agile methods for leading to endless cycles and introduces an appetite-driven strategy that sets fixed timelines. Singer emphasizes effective collaboration through shaping sessions and flexible team structures to clarify project goals. He highlights techniques like fat marker sketching to enhance communication and align engineering with design, making product development more efficient and empowering teams to thrive.

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00:00 / 00:00

Basecamp's Early Days

Ryan Singer, Jason Fried, and David Heinemeier Hansson (DHH) built the first Basecamp with a small, intensely collaborative team.
DHH initially worked part-time, coding only 10 hours weekly, which shaped their efficient product development.

00:00 / 00:00

Constraints and Urgency

DHH only had 10 hours a week to code, which forced the team to maximize efficiency.
Jason Fried, already known for urgency, compounded this focus on shipping quickly and iterating.

00:00 / 00:00

Shaping Sessions' Origin

Early Basecamp used short, intense shaping sessions to define product ideas.
These sessions involved collaborative brainstorming and quick sketches to get David's buy-in and avoid wasted development time.

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Competing Against Luck

Clayton M. Christensen

David S. Duncan

Taddy Hall

Karen Dillon

In 'Competing Against Luck,' Clayton Christensen and co-authors introduce the 'Jobs to Be Done' theory, which posits that customers 'hire' products to solve specific problems. The book provides real-world examples and tools for entrepreneurs to innovate effectively and create products that customers are willing to pay premium prices for. It offers insights into how companies like Uber and Airbnb have successfully applied this approach.

Shape Up

Ryan Singer

Shape Up is a book by Ryan Singer that provides a practical framework for managing software development projects. It emphasizes the importance of shaping work to fit within fixed time constraints, rather than fixing the scope and letting the time vary. The book introduces a three-stage process: shaping, building, and batting, which helps teams focus on delivering valuable work efficiently. Shape Up promotes a more collaborative and autonomous approach, empowering teams to make decisions and solve problems independently. The book's principles have been adopted by numerous teams and organizations seeking to improve their product development processes.

Demand-Side Sales 101

Bob Moesta

Greg Engle

In 'Demand-Side Sales 101', Bob Moesta and Greg Engle introduce a new perspective on sales by shifting the focus from selling products to helping customers achieve their goals. This approach emphasizes understanding the customer's needs and creating solutions that align with their objectives, rather than pushing features and benefits. The book provides frameworks for understanding buyer motivations and creating pull rather than push in sales.

Job Moves: 9 Steps for Making Progress in Your Career

Bob Moesta

Ethan Bernstein

Michael B. Horn

Job Moves provides a universally applicable model based on the 'Jobs to Be Done' theory, which views jobs as positions we 'hire' to solve problems in our lives. The book offers a 9-step framework to help job seekers make more informed choices about their career moves, focusing on understanding priorities, desired experiences, and tradeoffs. It is designed to help create a happier and more fulfilling career by taking a holistic view beyond job titles or companies.

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 them 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.

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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/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

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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

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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/

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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

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

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Lenny may be an investor in the companies discussed.

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