Technology Forecasting | Tales From The Sky Lounge

December 31, 2025

2026 Trends: Trust in AI, Healthcare, College, AGI & More | Bryan Dennstedt, Ep 41

Todd and Bryan Dennstedt review their 2025 AI predictions, finding they accurately forecasted the AI trough of disillusionment, agentic AI emergence, and VC conservatism. They predict 2026 will be defined by organizational absorption of AI capabilities rather than new breakthroughs, with agentic workflows becoming default, SaaS pricing models compressing, and trust verification emerging as a critical business category. They emphasize that rapid AI-powered software development is fundamentally changing startup economics and making previously marginal business ideas viable.

June 24, 2025

SpeedRun Ep14 Ask a Blue Shirt Tales from the Sky Lounge

A CTO demonstrates building a vector database search system in one evening using Claude Code, outpacing weekend projects built with no-code tools. He contrasts Claude Desktop's planning capabilities with Claude Code's implementation power, showing how AI enables rapid development of production-grade infrastructure including AWS deployment, MCP servers, and WordPress plugins.

June 20, 2025

SpeedRun Ep 06 Durable Agent Writing -Tales from the Sky Lounge

A CTO demonstrates how to convert Claude Desktop prototypes into production-ready AI agents using Python, Pydantic, and LangGraph. The episode walks through extracting MCP tool configurations and system prompts from chat sessions, then generating deployable code that can run on schedules or respond to events—illustrating how agent development costs are approaching zero.

April 30, 2025

Tariffs and Economic Uncertainty: How We Got Here and What's Next | Michael Weinstein, Ep 28

Michael Weinstein, a fractional CFO with decades of Wall Street and corporate finance experience, analyzes the current economic uncertainty driven by tariff policy, Federal Reserve decisions, and structural market challenges. He explains how tariffs function as a massive tax increase, why venture capital liquidity has frozen, and how uncertainty prevents corporate investment—while arguing that entrepreneurship and new business formation will ultimately lead the economy out of stagnation.

January 9, 2025

2025 Trends: AI, Venture Capital, and the Future of Work | Bryan Dennstedt, Ep 22

Bryan Dennstedt, fractional CTO at Tech CXO and sustainable investing advocate, discusses 2025 trends with host Todd. They cover venture capital's conservative shift post-SVB, AI's permeation across business (from agents to trust frameworks), the rise of niche podcasts and influencer marketing, and crypto's regulatory thaw under new US leadership. Core insight: AI and blockchain will become as fundamental as electricity, but organizations must navigate trust, compliance, and the trough of disillusionment before realizing transformative value.

June 14, 2024

Insights, Tips, Tricks and Wisdom from a Tech Veteran | Rob Reesor, Ep 11

Rob Reesor shares his journey from early AI expert systems development at Intellicorp through pioneering e-commerce at Virtual Vineyards to executive technology leadership across multiple private equity-backed companies. He discusses the evolution of software development practices, the challenges of technical debt management, and the critical importance of trust-based leadership in building high-performing engineering teams.

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