A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)
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.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Shipping work that matters (Interview)
We’re revisiting Shape Up and product development thoughts with Ryan Singer, Head of Product Strategy at Basecamp. Last August we talked with Ryan when he first launched his book Shape Up and now we’re back to see how Shape Up is shaping up — “How are teams using the wisdom in this book to actually ship work that matters? How does Shape Up work in new versus existing products?” We also talk about the concept of longitudinal thinking and the way it’s impacting Ryan’s designs, plus a grab bag of topics in the last segment.
Join the discussion
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Featuring:
Ryan Singer – Website, GitHub, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
Jerod Santo – Website, GitHub, LinkedIn, Mastodon, X
Show Notes:
The Changelog #357: Shaping, betting, and building
Ryan’s new hobby podcast called Synthetic A Priori
Shape Up (book site)
“Good design requires thinking longitudinally.”
New versus existing products
Taguchi methods on Wikipedia
Salt. Fat. Acid. Heat. - If you can master these four elements, you can master the kitchen.
EconTalk podcast
The End of Average: How We Succeed in a World That Values Sameness
Dr Ole Peters
Time for a Change: Introducing irreversible time in economics by Dr Ole Peters
Something missing or broken? PRs welcome!
How To Ship Work That Matters with Basecamp’s Ryan Singer
On this episode Abadesi talks to Ryan Singer, head of Product Strategy at Basecamp, where he’s worked for 16 years, ever since 2003. He is the author of Shape Up: Stop Running in Circles and Ship Work That Matters. You can read the book for free online.
In this episode they talk about...
How Basecamp cultivates their unique company culture
“If you think something is going to work, then go make it and let’s look at what you made in two or three days or a week. If you can’t make anything yet that works, maybe it’s not real and not ready yet. Don’t make me a big document about how it’s going to work — let’s make a prototype and click on it and see if it’s going to work.”
Ryan says that he was initially a UI designer and got into programming after joining Basecamp. He was at what was then called 37signals when Ruby on Rails was being created. He talks about the culture of shipping at Basecamp and how the learnings from his sixteen years at the company have made it into the book.
Why wireframes and documents are overrated
“If we over-specify the design up front with a lot of wireframes, we make the most decisions when we have the least information.”
Ryan says that at Basecamp, they use breadboards and fat marker sketches to mock up potential products, rather than detailed documents or pixel-perfect wireframes. He explains why it’s important to allow for improvisation by the designers and developers of products, and why you shouldn’t make the key trade-offs in the design phase, but instead after you’ve seen and used a prototype. He says that you “need to find the right level of abstraction” in your designs.
Why betting is better than planning
“We acknowledge the reality, which is that we don’t know what’s going to happen, we don’t know how this is going to work out, we’re probably going to be wrong about some things, so we want to use the language of risk instead of the language of certainty.”
At Basecamp, instead of making plans, they make bets. Ryan explains why this provides a better framework for the work that they do. He points out that when you make bets, you bet a fixed amount. They do the same at Basecamp, “betting” a certain amount of time on a project to see if it will work. If at the end of that time, it didn’t work out, they don’t spend more time than they originally “bet” on it chasing sunk costs.
How to find balance at work, and why Basecamp doesn’t think about “maximizing capacity”
Ryan says that they don’t think about “maximizing capacity” from their employees. Instead, they want to make sure that their workers have a meaningful goal with good odds for success. He says that managing how many hours someone worked the day before or today means very little. His advice is to stop micromanaging employee time and to experiment with a more flexible approach at your company. He also points out that they try to think about strategy at a more macro level than in terms of days or hours.
How to separate strategic failure from execution failure
“I would much rather have a healthy team that’s good at shipping stuff and occasionally make a strategic mistake. Because our bets have a limited downside, we’re setting out how much it is worth at the beginning. We only lose however much time we set out initially.”
As part of their unique approach to strategy, they are able to manage their downside by setting out the amount of time they’re willing to spend on something in the beginning. They trust their teams to figure out the details of the work on their own, without prescribing every detail of the product in the beginning. He explains how this is important to morale and what the difference between “imagined work” and “discovered work” is.
Ryan also talks about his love for the Apple Pencil and the iPad, and how he uses them to get his work done.
Bonus Content: Aba and the community on personal branding
We have more bonus content for you this week! Aba recently hosted a Periscope session where she invited all of you in the community to call in and explain what sites you use for personal branding and why. They covered LinkedIn, Medium, Twitter, personal sites, mailing lists, and more. If you want to be part of the next session (and maybe even be part of the podcast!) be sure to follow us on social media.
We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. 😸
Companies and Products Mentioned In This Episode
iPad + Apple Pencil
The Economist’s Mobile App
Shaping, betting, and building (Interview)
Ryan Singer, head of Product Strategy at Basecamp, joined the show to talk about their newest book — Shape Up: Stop running in circles and ship work that matters. It’s written by Ryan himself and you can read it right now for free online at Basecamp.com/shapeup.
We talked about the back story of the book, how the methodology for Shape Up developed from within at Basecamp, the principles and methodologies of Shape Up, how teams of varying sizes can implement Shape Up. Ryan even shared a special invitation to our listeners near the end of the show to his live and in-person Shape Up workshop on August 28th in Detroit, Michigan.
Join the discussion
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Featuring:
Ryan Singer – Website, GitHub, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
Jerod Santo – Website, GitHub, LinkedIn, Mastodon, X
Show Notes:
Shape Up
Foreword by Jason Fried
Principles of shaping
Example pitches — “How we do it in Basecamp”
Bets, Not Backlogs
How to Begin to Shape Up
Summary of the Shape Up method
Shape Up glossary
Ryan’s tweet about the Shape Up workshop
If you have questions — email shapeup@basecamp.com
Getting Real
All of Basecamp’s books
Something missing or broken? PRs welcome!