The Reasoning Show
Massive Studios
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
Episodes
Mentioned books
42 snips
Mar 4, 2026 • 26min
What is an AI Agent?
They dig into why agentic AI is taking off now and what changed since chatbots. Listeners hear a clear contrast between chat interfaces and autonomous agents with goals, memory, tools, and iterative loops. Design tradeoffs get attention, from task definition to human-in-the-loop choices. Frameworks, pricing approaches, and how agents will reshape enterprise work are also discussed.
45 snips
Feb 28, 2026 • 42min
AI & Cloud News of the Month - Feb 2026
Brandon Whichard, regular contributor from Software Defined Talk who covers cloud and AI trends. He discusses the show’s shift toward AI, the future of AI-generated code and Linux 7.0, Anthropic’s enterprise push versus OpenAI, the rise of agent-native assistants and OpenClaw, and how bottoms-up AI prototypes are changing teams and tooling.
52 snips
Feb 25, 2026 • 18min
How The Cloudcast is changing in 2026?
They announce a rebrand and format shift as AI overtakes cloud as the main focus. They outline new content buckets: AI technology, economics, trends, use cases, productivity, and regulation. Plans include audio plus video clips, varied episode lengths, a newsletter, and keeping monthly cloud coverage. Timeline and new website tooling are discussed.
19 snips
Feb 22, 2026 • 19min
What's Your Token Budget?
They dig into rising costs of AI agents and how token budgets compare to paying people. They debate centralized versus decentralized compute and what owning tokens could mean for companies. They explore translating token usage into business metrics and the shifting economics from training to operational costs.
20 snips
Feb 18, 2026 • 29min
Evaluating AI Models in 2026
They debate why constant AI model releases create numbness and how release timing affects adoption. They outline an initial evaluation checklist for enterprise suitability and integration. They scrutinize benchmarks, their limits, and independent benchmarking resources. They compare efficiency versus raw power and discuss versioning, vendor stability, and enterprise deployment challenges.
26 snips
Feb 15, 2026 • 13min
Three AI Rooms to be a Fly on the Wall in 2026
A peek into three high-stakes rooms shaping AI futures in 2026. Speculation on NVIDIA’s M&A playbook across chips, software, hosting and agentic tools. Curiosity about Anthropic’s agentic roadmap and how agents could reshape developer workflows and verticals. Deep dive into TSMC’s 2028–2030 planning, capacity risks and supply chain impacts.
32 snips
Feb 11, 2026 • 31min
What we wish we knew about the next 3 years of AI?
A lively look ahead at AI’s next three years, covering who will pay for frontier models and the CapEx race behind them. They debate winner-take-all dynamics, rising barriers for startups, and how pricing models like seats, tokens, and outcome billing might evolve. Political and regulatory risks get attention, along with shifts from LLMs to new architectures and the reshaping of jobs and usage patterns.
16 snips
Feb 8, 2026 • 16min
The Economics of Software Developers
Brandon Whichard, a cloud-native leader who advises on product strategy and developer workflows. He explores valuing software in 2026 amid AI and agents. He contrasts internal systems with customer-facing products. He discusses new in-house skills, vetting AI contributions, and using agents for rapid prototyping and product-led teams.
54 snips
Feb 4, 2026 • 27min
The Future of Enterprise Software?
A forward-looking look at how AI could upend legacy enterprise software and SaaS economics. Short takes on whether companies will build more custom software or stick with familiar big vendors. Questions about agentic tools enabling new collaborative software communities. Consideration of the hidden costs and organizational choices firms face as AI reshapes software ownership.
35 snips
Feb 1, 2026 • 33min
The Rise of Digital Sovereignty
A listener question sparks a deep dive into digital sovereignty, tariffs and European dependence on U.S. cloud providers. The show breaks down four sovereignty pillars: data, technical, operational and assurance. Legal responses, past sanctions that raised alarms, and how major vendors and governments are adapting are explored. Practical strategies for assessing sovereignty needs and building hedges are discussed.
