The Reasoning Show
The Reasoning Show AI moves fast. Thinking clearly matters more.
The Reasoning Show cuts through the hype to explore how the smartest people in enterprise AI actually make decisions — the strategy, the tradeoffs, and the hard lessons no press release mentions.
Every week, hosts Aaron Delp and Brian Gracely sit down with the founders building the tools, investors funding the shift, and operators running AI in the real world. Not hype. Not panic. Just clear-headed conversations with people who have to make actual decisions.
Because the AI revolution isn't just happening. It's being reasoned through.
New shows every Wednesday and Sunday.
Topics: Enterprise AI strategy · LLMs in production · AI leadership · Agentic AI · Digital Sovereignty · Machine Learning · AI startups · Cloud Computing
The Reasoning Show
The Cloudcast #287 - Venture Capital and the Cloud Native Landscape
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Show Links:
- Get a free eBook from O'Reilly media or use promo code PCBW for a discount - 40% off Print Books and 50% off eBooks and videos
- RedPoint Ventures website
- RedPoint “Memory Leak” Blog
- The Cloud Native Landscape (Project) (with CNCF)
- Topic 1 - Welcome to the show. We always love to get a Venture Capital perspective on the show from time to time. Tell us about yourself and maybe a little bit about your current areas of focus.
- Topic 2 - At the recent CNCF event (KubeCon, etc.), Dan Kohn introduced the Cloud Native Landscape, which was built in partnership with RedPoint Ventures. Help us understand the framework and how people are using it today.
- Topic 3 - Many of the things on that landscape are either open source projects or companies that are commercializing some aspect of those projects. We’ve heard various theories on what those business models look like, but I’m curious about how you advise your companies in this space.
- Topic 4 - Let’s talk for a second about the pace of change. Things are moving faster than ever. How do you advise companies to build their business, whether it’s long-term or IPO or M&A, or just survival techniques?
- Topic 5 - Twilio is one of your portfolio companies, and they were highlighted at AWS re:Invent last week. AWS often creates services that overlap companies that run on the platform. How much does someone like Twilio worry that there will be something like “AWS Telephone” being announced in 2017?
- Topic 6 - We just had an election here in the US and a certain amount of uncertainty and change is inevitable with any new administration. How does RedPoint think about this transition and how it impacts existing portfolio companies and your investment thesis for the future?
- Email:show at thecloudcast dot net
- Twitter:@thecloudcastnet or @serverlesscast
- YouTube:Cloudcast Channel
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