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

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

Lenny's Podcast: Product | Career | Growth

March 30, 2025

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.
Speakers: Ryan Singer, Lenny Rachitsky
**Ryan Singer** (0:00)
I often use this analogy of like, if you're doing a home renovation, you can have like the most beautiful rendering of the new bedroom, and we're going to have these lamps on the side of the bed that are coming out from the wall. But if you haven't checked if there's electricity in that wall there or not, it's going to drastically change the cost and the time and everything. What we need to do in a shaping session is we come out with some kind of diagram where engineers, product and design, they're saying, we understand that. So the first thing is, we are not going to start something unless we can see the end from the beginning. We're not going to take a big concept and then say, what's the estimate for this thing? We're going to go the other way around and we're going to say, what is the maximum amount of time we're willing to go before we actually finish something? How do we come up with a idea that's going to work in the amount of time that the business is interested in spending?

**Lenny Rachitsky** (0:54)
Today, my guest is Ryan Singer. Ryan was one of the first few hires at 37signals, and through his experience of building Basecamp, and his 17 years of building products at 37signals, he wrote a book called Shape Up, which shares a very different approach to building software. Appetites instead of deadlines, a big focus on bringing design engine product together into a room to shape the plan, versus writing long PRDs or trying to finalize designs before you start building. I've noticed more and more teams adopting the Shape Up method, and especially with AI starting to change how we work and build product, there's a shift coming in how product teams will operate. And so I thought this was the perfect time to do a deep dive into the Shape Up method. This episode is basically going to give you everything you need to give Shape Up a shot on your team or at your company to see if it fixes the problems that you're having shipping great products. A big thank you to Des Traynor, Bob Moesta and Chris Speck for suggesting questions and topics for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also if you become a paid subscriber of my newsletter, you get an entire year free of Perplexity Pro, Notion, Superhuman, Linear and Granola. Check it out at Lenny's newsletter.com. With that, I bring you Ryan Singer. This episode is brought to you by Work OS. If you're building a SaaS app, at some point your customers will start asking for enterprise features, like SAML authentication and skim provisioning. That's where Work OS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by Work OS, including ones you probably know, like Vercell, Webflow and Loom. Work OS also recently acquired Warrant, the fine-grain authorization service. Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale, while maintaining a flexible model that can be adapted to even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features like single sign-on, skim or user management, you should consider Work OS. It's a drop-in replacement for Auth0 and supports up to 1 million monthly active users for free. Check it out at workos.com to learn more. That's workos.com. This episode is brought to you by Merge. Product leaders, yes, like you, cringe when they hear the word integration. They're not fun for you to scope, build, launch, or maintain, and integrations probably aren't what led you to product work in the first place. Lucky for you, the folks at Merge are obsessed with integrations. Their single API helps SaaS companies launch over 200 product integrations in weeks, not quarters. Think of Merge like Plaid, but for everything B2B SaaS. Organizations like Ramp, Dorada, and Electric use Merge to access their customer's accounting data to reconcile bill payments, file storage data to create searchable databases in their product, or HRIS data to auto-provision and deprovision access for their customer's employees. And yes, if you need AI-ready data for your SaaS product, then Merge is the fastest way to get it. So, want to solve your organization's integration dilemma once and for all? Book and attend a meeting at merge.dev slash Lenny and receive a $50 Amazon gift card. That's merge.dev slash Lenny.

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