Technology Forecasting | Tales From The Sky Lounge

December 31, 2025

Ep41 Bryan Dennstedt of AIWithBry—2026 Trends: Trust in AI, Healthcare, College, AGI & more

Todd and Bryan Dennstedt review their 2025 AI predictions and discuss 2026 trends including agentic AI workflows, SaaS pricing disruption, trust verification systems, and the transformation of software development through AI-powered rapid prototyping. They explore how AI is enabling low-capital entrepreneurship, challenging traditional venture models, and requiring fundamental shifts in business planning and execution.

December 31, 2025

Welcome to our live show!

Todd and Brian review their 2025 predictions about AI adoption, venture capital, and technology trends, then discuss 2026 forecasts. They explore how AI agents are transforming software development, the shift from SaaS models to custom automation, and emerging opportunities in local manufacturing and rapid business creation enabled by AI tools.

June 24, 2025

SpeedRun Ep14 Ask a Blue Shirt Tales from the Sky Lounge

A CTO demonstrates how to rapidly build a vector database search system using AI coding tools like Claude Desktop and Claude Code, contrasting professional implementation with amateur 'script kiddie' approaches. The episode walks through iterating on architecture decisions, generating infrastructure-as-code, and creating a full-stack solution including REST API, WordPress plugin, and MCP server in under two hours.

June 20, 2025

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

A technical exploration of converting Claude Desktop prototypes into production-ready AI agents. The host demonstrates how to extract MCP tool configurations and conversation patterns from Claude Desktop sessions, then transform them into deployable Python code using frameworks like Pydantic and LangGraph, enabling rapid agent development and deployment.

April 30, 2025

Ep28 Michael Weinstein—Tariffs and Economic Uncertainty - How We Got Here & What's Next

Michael Weinstein, a fractional CFO with extensive Wall Street experience, discusses the current economic uncertainty driven by tariff policies, Federal Reserve decisions, and structural market challenges. He explains how tariffs function as a massive tax increase, analyzes the compounding effects of policy uncertainty on corporate investment, and examines the clogged venture capital pipeline. Weinstein draws historical parallels to past economic cycles while noting this situation is unique—a self-inflicted late-cycle shock with no clear playbook.

January 9, 2025

Ep22 Bryan Dennstedt—2025 Trends: AI, Venture Capital, and the Future of Work!

Bryan Dennstedt, fractional CTO at Tech CXO and sustainable investing advocate, discusses 2025 technology and business trends with host Todd. They explore venture capital's post-SVB recovery, AI's practical applications and limitations, the evolution of marketing through influencer content and podcasts, and emerging shifts in crypto regulation, intellectual property, and remote work culture.

June 14, 2024

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

Rob Reesor shares his four-decade technology career journey from early AI expert systems at Intellicorp through pioneering e-commerce at Virtual Vineyards to executive leadership roles across multiple private equity-backed companies. He discusses the evolution of software development, the challenges of technical debt management, building trust with non-technical stakeholders, and navigating acquisitions while emphasizing transparency and team empowerment.

Want to go deeper?

Work With Me

Back to all topics