In this episode of The Tech Trek, Amir talks with Keenan Wyrobek, co-founder and CTO of Zipline, about building one of the world’s largest autonomous logistics platforms. From delivering life-saving supplies in remote regions to scaling precision delivery in urban areas, Keenan shares how Zipline combines first-principles thinking, tight hardware-software integration, and customer obsession to create a mission-critical product that redefines what's possible.

🔑 Key Takeaways

Talk to the Customer, Not Just About Them: True product breakthroughs come from deeply understanding—not just listening to—customers.

Parallel Innovation: Zipline tackles hardware and software together, with dedicated teams focused on de-risking product-critical challenges.

Celebrate Speed of Learning: Zipline rewards the pace of iteration over polished perfection to maintain forward momentum.

Architect for Simplicity: Complexity is the enemy—every system must be ruthlessly simplified during the design process.

🧠 Standout Quote

“Shut up, get out, go understand what the customer needs… Every trade we make should be based on what matters to the customer.” – Keenan Wyrobek

⏱️ Timestamped Highlights

00:04 – Why engineering leaders spend a third of their time recruiting

01:50 – How Zipline evolved from medical supply drops to metro-area deliveries

04:51 – Field research before code: trips to Central America and Africa

08:18 – Prototyping from first principles and failed assumptions about drone availability

11:40 – Why Zipline had to build software reliability from scratch

14:32 – Keenan’s favorite interview technique to find first-principles thinkers

16:44 – “Bet the company” checkpoints and the conceptual/alpha/design phase breakdown

22:58 – Why risks, not domains, dictate Zipline’s team structure

25:58 – Organizing Zipline’s hardware/software teams around systems and simplicity

29:58 – How Zipline sustains motivation through customer connection and rapid learning