We discuss rapid prototyping & how eng leaders can develop better product instincts with David Crawshaw, CTO & Co-Founder @ Tailscale! He shares his leadership journey from Google to Tailscale and how the early product development days at his startup lead to incorporating rapid prototyping principles within their eng org. We also cover strategies and recommendations for those who are new to rapid prototyping, how to work with design & product teams while quickly iterating, navigating the tension between speed & quality, and how to avoid common pitfalls while implementing the process.

ABOUT DAVID CRAWSHAW

David Crawshaw (@davidcrawshaw) is co-founder and CTO of Tailscale. Previously he was a staff engineer at Google, where he specialized in petabyte-scale logs processing. He implemented TCP/IP networking for Fuchsia, as well as ported the Go language platform to iOS and Android.

"If you're a pre-seed startup in the Bay Area and you are trying to ship something to your first few customers and you ship with 40-something languages, then you've made a mistake, but it's not necessarily true that a large company has made that mistake. For larger companies with more total requirements, I think the big question is can you construct environments where you can experiment without all of these requirements?”

- David Crawshaw   

Join us at ELC Annual 2023!

ELC Annual is our flagship conference for engineering leaders. You’ll learn from experts in engineering and leadership, gain mentorship and support from like-minded professionals, expand your perspectives, build relationships across the tech industry, and leave with practical prove strategies.

Join us this August 30-31 at the Fort Mason Center in San Francisco

For tickets, head to https://sfelc.com/annual2023SHOW NOTES:

• David’s background at Google & the transition to founding Tailscale (1:51)
• Early-day challenges at Tailscale w/ prototyping (4:03)
• How Tailscale discovered & employed rapid prototyping during its early days (6:41)
• Paradigm shifts around the product-building process & feedback loop (8:37)
• Recommendations for those new to rapid prototyping (11:20)
• Shifting your org’s culture toward accelerated iteration cycles w/ arbitrary limits (13:36)
• Frameworks for getting to a faster prototype (16:52)
• How to work w/ design & product throughout rapid prototyping process (19:26)
• Navigating the tension between doing things quickly vs. working well (21:51)
• Where large companies try to rapid prototype & things go wrong (26:29)
• Trains vs. EVs in the Bay area – a metaphor for rapid iteration (28:46)
• Bringing that metaphor to software development (31:37)
• David’s perspective on widespread adoption of OpenAI (34:31)
• Rapid fire questions (39:19)

LINKS AND RESOURCES

• Tomorrow, and Tomorrow, and Tomorrow - In this exhilarating novel from Gabrielle Zevin, two friends--often in love, but never lovers--come together as creative partners in the world of video game design, where success brings them fame, joy, tragedy, duplicity, and, ultimately, a kind of immortality.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/