Tales From The Sky Lounge

Hosted by Todd Merrill

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO. He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

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March 24, 2026

Ep46-Rachel Zeller: Hiring Humans in an AI World

Rachel Zeller, Managing Director at Kitces.com, discusses how her company maintains human-centered hiring practices in an AI-saturated world. She shares strategies for identifying authentic candidates, including requiring AI transcripts with work samples, conducting process-focused interviews, and deliberately slowing down applications by turning off easy-apply features. The conversation explores balancing AI as a productivity tool while preserving genuine human connection in recruitment.

Merit-Based Hiring Remote Work Infrastructure

March 11, 2026

Ep45 John Church: Crypto Grows Up: Building at the Intersection of Blockchain and AI

John Church, lead product manager at Nethermind and adjunct professor at Duke University, discusses his journey from DAO leadership to institutional blockchain work. The conversation covers stablecoins, zero-knowledge cryptography, the intersection of AI and blockchain, and how crypto is maturing from speculative technology to institutional infrastructure. Church emphasizes the importance of fundamental understanding as AI transforms software development and entrepreneurship.

Conversational Software Development Low-Barrier AI Entrepreneurship

February 25, 2026

Ep44 Niral Shah: A Trauma Surgeon & Entrepreneur Talks Healthcare, AI and What’s Next

Niral Shah, a trauma surgeon and serial entrepreneur, discusses his journey from starting a search engine company during the dot-com boom to becoming a physician entrepreneur focused on healthcare innovation. He shares lessons from shutting down his first startup responsibly, explains why healthcare's structural inefficiencies are ripe for disruption, and identifies promising areas for AI and biotech innovation including at-home diagnostics, drug discovery using incomplete datasets, and real-time health monitoring.

Early E-commerce Innovation Healthcare Innovation Medical Market Research

February 4, 2026

Ep43 John Yates and Gregg Bedol—How Two Industry Veterans Are Solving Business Dev with TractionBD

John Yates, a tech attorney with 44 years of experience, and Greg Bedol, a serial entrepreneur and consultant, discuss their new venture Traction BD—a voice-enabled AI platform that automates business development for professionals. They explore how AI is revolutionizing relationship-based selling by making it easier to maintain consistent, personalized outreach without the emotional fatigue and time constraints that cause most professionals to abandon prospects after just 2-3 touches.

AI Workflow Automation Business Development CRM Implementation+2 more

January 21, 2026

Ep42 Chris Thomajan: Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners

Chris Thomajan, a CFO with 35 years of startup experience, discusses his career path from English major to finance leader across 100+ companies, primarily in Boston's biotech ecosystem. He shares frameworks for evaluating CEOs, navigating venture capital cycles, and managing founder transitions, emphasizing that betting on the right team matters more than the product itself.

Board Governance Fractional CFO Practice Professional Networking+2 more

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.

Agentic Framework Architecture AI Adoption Paradigm Shift Conversational Software Development+5 more

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