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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October 14, 2026

Adoption Isn't Impact: Where Enterprise AI Coding Stalls | Nadeem Haider | Ep 54

Nadeem Haider, a software engineering leader with 20 years at Citrix, maps the five-stage maturity curve enterprises face when adopting AI coding agents—from individual experimentation through team standardization to full agentic development. He argues that adoption metrics don't equal transformation, explains why 'AI ergonomics' of legacy codebases determine agent effectiveness, and advocates for risk-stratified code review where humans focus on high-blast-radius changes while agents handle boilerplate.

Adoption Metrics vs Impact Agent Allocation Planning Agentic Framework Architecture+6 more

September 23, 2026

The Crawl-Walk-Run Playbook for Adopting AI | Jim Hasty, Ep 53

Jim Hasty, founder of Cogle Group, discusses his company's evolution from technology consulting to AI-powered software products. He shares lessons from building Plan Checkers, an AI tool that reduces municipal permit review time from weeks to minutes, and outlines a crawl-walk-run framework for enterprise AI adoption focused on automating emotionally draining tasks rather than chasing adoption metrics.

AI Adoption Paradigm Shift AI Consulting Workshops Conversational Software Development+5 more

September 9, 2026

Founders: These Are the Mistakes You Don't Know You're Going to Make | Steve Walsh, Ep 52

Steve Walsh, an angel investor and startup advisor, shares lessons from 25 years building multi-billion dollar B2B divisions at Cox and Comcast before transitioning to helping early-stage founders. He discusses common founder mistakes, when to raise capital, the importance of customer validation before building product, and how he filters 6,000 conversations down to 69 investments through rigorous vetting and founder education.

Angel Investing CEO as Primary Salesperson Content Marketing+10 more

August 12, 2026

If You're Not Making Money, You're Not Worth Money: 1,000 Valuations | Gregg Ficery, Ep 51

Gregg Ficery, founder of Integgra Advisory Services, discusses his 15-year career in business valuation, explaining when companies need valuations (fundraising, 409A compliance, M&A, litigation), how to maximize company value, and current trends in venture capital and AI investment. He shares his journey from dot-com survivor to Silicon Valley Bank to independent consultant, plus his side project: a book documenting pre-NFL professional football history.

409A Compliance AI Adoption Trends Business Valuation Methodology+5 more

July 22, 2026

Parallel Entrepreneurism: Shipping Startups Side by Side | Kirby Winters, Ep 50

Kirby Winters discusses launching multiple ventures simultaneously using AI-powered development, including Cyber Savi (a compliance automation platform), a vodka brand, and Unshucked (an oyster tracking app). He explains how agentic AI enables building production-ready software in weeks instead of years, the shift from consulting to outcome-based services, and strategies for selling cybersecurity compliance tools through MSP channel partners.

Agentic Framework Architecture AI Adoption Paradigm Shift AI Workflow Automation+5 more

June 24, 2026

The CEO Is the Salesperson: Why Founders Can't Hand Off the Pitch | Jen Bonnett, Ep 49

Jennifer Bonnett, a longtime tech entrepreneur and former ecosystem builder at ATDC and Invest Atlanta, discusses her transition back into technology through AI experimentation. She shares lessons from building a search engine in 1997, her current work vibe coding consumer apps with Claude, and her philosophy that CEOs must personally sell for at least the first year before delegating. The conversation explores how AI is lowering barriers to entrepreneurship while emphasizing that founders still need strong networks, customer discovery skills, and the discipline to market early.

AI Agent Development CEO as Primary Salesperson Conversational Software Development+7 more

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