How Founders Win in the AI Era — Madrona’s Matt McIlwain & AWS’s Jon Jones on Strategy That Scales

During Seattle Tech Week 2025, Madrona's Matt McIlwain joined ‪@amazonwebservices‬ Startups' Jon Jones for an in-depth conversation covering the early days of Amazon and Madrona’s pivotal investment, the behind-the-scenes story of AWS’s launch, and the ongoing revolution in AI and business models.

Matt shares unique insights from decades of experience in tech, venture capital, and entrepreneurship, offering advice for founders and a look at the future of reasoning machines.
Key topics:
Madrona’s early investment in Amazon
The first AWS launch event and its impact
The rise of AI, machine learning, and the “reasoning revolution”
Why business models matter as much as AI models
Actionable advice for founders and innovators
Audience Q&A with Matt and Jon

Chapters:
00:00 – Introduction
01:00– Building Community in Seattle
02:47 – Early Days of Amazon - 30 Years Ago
03:54 – Madrona's 1995 Investment in Amazon
06:14 – First Encounters with AWS Infrastructure
08:09 – The Launch of AWS Services and Early Events
10:22 – Evolution of AWS and Customer Success Stories
13:10 – The Journey into Machine Learning and AI
16:00 – The Reasoning Revolution: A New Economic Era
18:57 – Understanding Reasoning Flywheels and AI Moats
21:13 – Leadership Scaling and Andy Jassy's Impact
24:05 – The Importance of Business Models in AI
27:18 – Future Innovations and Emerging Technologies
29:34 – Advice for Entrepreneurs & Audience Q&A

‪@amazonwebservices‬