All Episodes

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.

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.

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.

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.

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.

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.

2025 Travel Stories: What Happens When You Get Out There to Make Things Happen!

Ep40—Steve Subar—Business Model First, Product Second: Thirty Years of Building Smarter

Ep 39—Neal Miller-Decades of Financial Strategy Across 70 Companies and Still Going

Neil Miller, a partner emeritus at Tech CXO with 19 years at the firm, shares his journey from public accounting through CFO roles at multiple public companies to fractional executive work. He discusses his involvement with 70+ companies including Cloud Sherpas and Boomtown, offering insights on fundraising challenges, the fractional executive model's value during economic uncertainty, and how AI is compressing business cycles while changing capital requirements.

Ep38—Louis Gump-Innovation, Timing, and Leadership: Whether You're an Entrepreneur or Intrapreneur

Lewis Gump, a fractional CEO/COO and author of 'Gorilla Marketing Tactic,' discusses his career building mobile and digital businesses at CNN and The Weather Channel, the critical differences between entrepreneurs and intrapreneurs, and how founders can successfully transition into larger organizations post-acquisition. He emphasizes that innovation requires leadership commitment, cultural fit, and the ability to build bridges across diverse teams.

Ep37—Mike Martin: Big Tobacco to Government Contracts: Building Breakthrough Brand Campaigns

Mike Martin, fractional CMO at Tech CXO, discusses his career journey from landscape architecture to advertising, including breakthrough campaigns for the Truth anti-smoking initiative and Monster.com's Super Bowl ads. He shares insights on modern marketing challenges, the role of AI in creative work, and lessons learned from both toxic leadership and successful brand building across hospitality, e-commerce, and government sectors.

Ep36—Ted Stone: Decades of Financial Strategy — Still in the Game and Giving Back

Ted Stone, a 72-year-old career CFO, discusses his transition to fractional CFO work serving multiple clients across diverse industries. He shares detailed stories from three major private equity deals—Velocity Express (a last-mile delivery rollup), an office telephone company spin-out, and Solucent (a healthcare data integration)—while exploring current trends including the silver tsunami of retiring business owners, ESOP structures, and the value of executive peer networks like Executive Forum.

Ep35 — Virginie Glaenzer: Rewriting the Rules: Growth, AI, Community, and the Meaning of Wealth

Virginie Glaenzer, a fractional CMO and author, shares her journey from Paris to Silicon Valley in 1998 with four suitcases and no English, building tech companies through the dot-com era. She discusses AI's transformative impact on business, the shift from scarcity-based to abundance-based thinking, and why future-proof brands must build communities into their DNA rather than treating them as marketing tactics.

Ep 34 - Brantley Fry: Why Connecting People and Process Is Your Secret Weapon

Brantley Fry, partner at Tech CXO's human capital management practice, shares her unconventional career path from environmental lawyer to political state director to HR strategist. She discusses her work on major environmental cases including the TVA coal ash spill and BP oil spill, her role as state director for Senator Doug Jones, and her current focus on helping high-growth companies optimize people operations. The conversation explores M&A communication strategies, non-traditional hiring approaches, and Birmingham's emerging biotech ecosystem.

Ep 33 - Alex Gafford: The 5-Hour Formula for Maximum Productivity in Minimal Time

Alex Gafford, a corporate finance professional specializing in technology debt lending, discusses his company's pioneering five-hour workday model implemented since 2016. The conversation explores how condensed work schedules, strategic time blocking based on ultradian rhythms, and ruthless elimination of distractions have increased productivity by 30% while dramatically improving employee retention and quality of life.

SpeedRun Ep19 Marketing Plans with Virginie Glaenzer - Tales from the Sky Lounge

Todd and Virginie demonstrate live how to build a complete marketing plan using AI tools like ChatGPT and Claude. They identify lack of clarity as the biggest barrier to AI adoption among executives, design a five-step 'AI Value Blueprint' service offering targeting CMOs, CROs, and COOs in B2B SaaS, and develop persona-specific messaging and automation workflows—all within one hour using conversational AI.

SpeedRun Ep20 Canva with Mike Martin - Tales from the Sky Lounge

Ep32 Joe Gruca—From Pink Slip to Pivot: Predictable Sales in Unpredictable Markets

Joe Gruca shares his journey from corporate VP of Sales at Computer Associates to co-founding Higher IQ, an AI-powered interview automation platform, after being laid off in 2008. He discusses pivoting the business model, raising venture capital, successfully exiting, and now helping early-stage tech CEOs as a fractional revenue leader at Tech CXO. The conversation covers sales methodology evolution, startup lessons, and navigating economic uncertainty.

SpeedRun Ep18 wordpress Tales from the Sky Lounge

A developer attempts to use AI (Claude) to diagnose and fix WordPress SEO and indexing problems, including missing robots.txt, schema markup issues, and Google Search Console configuration. The experiment reveals important lessons about AI limitations, the need for human oversight at checkpoints, and the challenges of letting AI make bulk changes without incremental validation.

SpeedRun Ep12 Conference Attendee Email Lead Parsing Tales from the Sky Lounge

The host experiments with using Claude AI to automate conference attendee lead generation and marketing campaign creation. Starting with a PDF list of parking lot conference attendees, Claude autonomously researches the conference, segments prospects, writes email campaigns, and creates lead scoring frameworks—though it hits output limits when generating the final CSV export.

SpeedRun Ep13 Email Marketing Write an Agent Tales from the Sky Lounge

A demonstration of using Claude AI to automate email marketing workflow development from a single meeting recording. The host feeds meeting notes into Claude, which then designs a complete email marketing system including segmentation logic, HubSpot integration, Python code, file structures, and sample email sequences—all generated through conversational prompts without traditional coding.

SpeedRun Ep11 Medical Videos Ideation Tales from the Sky Lounge

The host demonstrates using Claude AI to develop a marketing strategy for a medical SaaS client with an AI diagnostic chatbot. Through iterative prompting, Claude generates platform-specific content strategies for LinkedIn, YouTube, and TikTok, analyzes what drives healthcare professional engagement, and proposes viral marketing concepts inspired by 'Will It Blend' and House MD's diagnostic approach.

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.

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.

SpeedRun Ep 10 audio engineer local bizdev p -Tales from the Sky Lounge

A father demonstrates how AI (Claude) helped his college-age son, an aspiring audio engineer, develop a comprehensive business development plan for launching a recording studio service in Atlanta's hip-hop scene. Using a $350 budget and access to two local studios, the AI generated detailed market analysis, pricing strategies, venue partnerships, social media tactics, and a 90-day action plan tailored to the local music ecosystem.

SpeedRun Ep 05 Projects with SOW from Notes and Emails -Tales from the Sky Lounge

A demonstration of using Claude Desktop with MCP integrations to automate proposal generation. The host connects Google Drive and Gmail, feeds meeting transcriptions and email threads into Claude, and generates a complete statement of work by synthesizing client requirements, meeting notes, and web research—all formatted to a template and saved automatically.

SpeedRun Ep 09 Resource Use for ICP + GTM Plan -Tales from the Sky Lounge

A fractional CTO demonstrates using Claude AI with deep research mode to generate a comprehensive business development and go-to-market plan for his consulting practice. By uploading PDFs of marketing materials, case studies, and service offerings, he prompts the AI to identify ideal customer profiles across four tiers, create multi-channel outreach strategies, and produce detailed execution plans including email templates and event recommendations—all refined through iterative conversation.

Ep31 Mike Biwer—The Hidden Engine of the Economy: Unpacking the Power of Distribution with Cavallo

Mike Biwer, CEO of Cavalo, discusses how his company helps wholesale distributors optimize profitability through technology that controls pricing and margins at the line-item level. Founded by a distributor who built software to solve his own business problems, Cavalo evolved from a Microsoft Dynamics add-on to a multi-platform solution serving the $10 trillion distribution industry. Biwer shares insights on navigating ERP migrations, maintaining product-market fit, and competing in a fragmented market where average pre-tax profit margins are under 5%.

Ep30 Bob Brogan—Road Warrior to Business Architect: 40 Years of Transforming Companies

Bob Brogan shares four decades of experience transforming companies across operations, IT consulting, and strategy. From early data warehousing in Canada to leading a $100M exit for a 43-year-old online ordering pioneer, he discusses business cycles, modular design principles, and the transition from tactical execution to strategic leadership. Now managing partner at Tech CXO Great Lakes, he emphasizes paying forward through mentorship, angel investing, and community work including founding the Legacy Guild scholarship program.

Ep29 Teja Yenamandra—Beyond Resumes-The Case for Talent-First, Human-Centered Hiring

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.

Ep27 Jeff Haynie—The Rise of Agentic Systems and AI-Driven Dev

Jeff Haynie, serial entrepreneur and founder of Appcelerator (Titanium), discusses his journey from pioneering JavaScript mobile development in 2006 to launching Agentuity, an AI agent cloud platform. He shares insights on Silicon Valley's unique ecosystem, the evolution of software development, and his belief that AI agents will fundamentally transform cloud infrastructure from human-centric to agent-optimized systems.

Ep26 Matt Oess -Coaching Elite Leaders, AI Productivity & The Need for Tech Diplomacy

Ep25 Lisa Calhoun—Earning Every Win: Grit, Innovation, and Knowing When to Venture!

Ep24 Alan Gold—Sales, Marketing, and AI: How to Survive, Scale, and Avoid Stagnation

Alan Gold, a fractional CMO and sales consultant with 30+ years in technology marketing, discusses the evolving landscape of sales and marketing in the AI era. He covers M&A market dynamics, hiring and developing sales talent, the critical importance of strategy over tactics in marketing, and how companies can break through growth plateaus by finding adjacent markets and refining their differentiation.

Ep22 Antonio Pagano—Phishing, AI Scams, and the Ever-Intensifying Cybersecurity War

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.

Travel Stories Compilation: Perspectives, Peeves, Perks, Profound Lessons and Priceless Stories

Ep21 James Rozich— Sales, Marketing, Sumerians and Avoiding Founder's Disease!

Jim Rozich, founder of Wheels Up Sales and Marketing, discusses helping early-stage startups build effective sales processes and avoid common founder mistakes. He emphasizes value-based messaging over feature lists, proper CRM implementation, and understanding buyer psychology. The conversation covers cold email strategy, multi-channel outreach, AI tools for sales, and the importance of discovery calls that prioritize listening over pitching.

Ep20 Adam Lehde — Family Values, Ukrainian Excellence: Creating the Ideal Workplace

Adam Lehde, co-founder of Happen Technologies, discusses building a hybrid software development company that partners US-based strategy with Ukrainian technical talent. He shares his journey from mobile developer to entrepreneur, the cultural strengths of Ukrainian developers, and his philosophy of building a family-first company culture while maintaining high performance through direct communication and ownership mentality.

Ep 19 Kathryn O'Day —Triathlons, Startups, and Success: A Playbook for Entrepreneurs

Ep18 Ghazenfer Mansoor — A Born Entrepreneur Talks Startups, Product Blueprints, and Global Scaling

Ghazenfer Mansoor, founder of Technology Divers, shares his journey from Pakistan to the US, building a mobile app development company that evolved into a product development consultancy. He discusses his 'blueprint methodology' for converting napkin sketches into production-ready software, managing distributed teams across multiple continents, and helping non-technical founders navigate the complexities of software development. The conversation covers entrepreneurial mindset, AI's impact on software development, and the importance of peer groups for founders.

Ep17 - Kirby Winters — Scout Skills, Leadership Hacks, and Smart Security in the Age of AI

Kirby Winters, fractional CISO at TechCXO, discusses his journey from telecom to cybersecurity consulting, emphasizing leadership lessons from Boy Scouts and entrepreneurship. He covers the evolving threat landscape, social engineering attacks, cyber insurance challenges, and compliance requirements like SOC 2 and CMMC. The conversation explores how AI is amplifying security risks and the growing need for fractional security leadership in small to mid-sized businesses.

Ep16 - Rich Makover—Leadership, Resilience, and Sales Mastery

Rich Makover, a fractional Chief Revenue Officer and executive coach at TechCXO, shares his journey from Penn State lacrosse player to CPA to sales leadership at Avon and beyond. He discusses the value of athletic resilience in sales, the evolution from individual contributor to C-suite executive, and his transition into fractional leadership and executive coaching. The conversation covers sales strategy, team building, leadership development, and helping professionals navigate career transitions.

Ep15 - IT Roundtable: Leadership and Cost Optimization in Challenging Times

Ep 14 - AI Roundtable— Where Do We Stand and What’s Next?

A panel discussion featuring AI and machine learning experts Joel Foreman (Airworks), Nick Vasilioglou (Relational AI), and Kevin (TechCXO) exploring the current state and future of AI technology. They discuss the distinction between AI and machine learning, practical applications of LLMs, concerns about AI hype versus reality, ethical considerations around training data, and emerging innovations in computer vision, semantic layers, and enterprise AI implementation.

Ep 13 - Marc McCarthy— Mastering Market Entry from Either Side of the Pond

Mark McCarthy, founder of Pro Consult IQ, discusses the complexities of cross-Atlantic business expansion for B2B software companies. He covers cultural differences in sales approaches, regulatory considerations across US states versus UK markets, and the critical importance of hiring locally and understanding regional business practices. McCarthy emphasizes that successful market entry requires more than language compatibility—it demands cultural adaptation, proper incorporation, local partnerships, and strategic timing for direct market presence.

Ep12 Katherine Hunter-Blyden: Tips on the Modern Marketing Landscape from a Seasoned Expert

Katherine Hunter-Blyden, a fractional CMO, discusses her career journey from Fortune 500 companies like Ford and Progressive to serving small businesses. She shares insights on modern marketing strategies, the importance of email marketing and content distribution, measuring business growth, and how AI tools are transforming marketing efficiency. The conversation covers practical approaches to brand building, direct response marketing, and the critical differences between marketing at scale versus scrappy startup environments.

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.

Ep 10 - Chris Caparon: Hard-Won Lessons from a Long and Successful Tech Journey

Chris Caparon shares his 20-year journey building Sephoria Software, an accounts receivable automation company that grew from a garage startup in 2001 to serving Fortune 500 companies across 110 countries before its private equity exit. He discusses navigating multiple economic crises, evolving technology platforms, and the critical importance of customer-centric product development and maintaining strong founder relationships throughout the company lifecycle.

Ep 09 - Bart Foster: Grit Becomes Growth, the Path from Pain to Transformation

Bart Foster shares his journey from corporate executive to founder of SoloHealth, a health screening kiosk company that scaled to 4,000 Walmart locations before he was forced out by his board. After moving to Boulder, Colorado, he founded Business Outside, which uses nature-based experiences to help corporate teams build authentic connections and develop intentional leadership approaches.

Ep 08 - David Morczinek: Machine Learning at MIT to Entrepreneurial Growth and Fundraising Success.

David Morczinek, CEO of Airworks, discusses his journey from aerospace engineering at Airbus to co-founding a geospatial AI company at MIT. He explains how Airworks uses computer vision to analyze aerial data from drones, satellites, and aircraft, pivoting from pure automation to a hybrid service model when customers struggled with AI adoption. The conversation covers fundraising progression from friends-and-family to private equity, balancing technical innovation with market readiness, and building a sustainable company culture.

Ep 07 - Christy Johnson - Cultivating Resilience Through Adaptation, Partnership and Growth

Christy Johnson, performance engineering lead at VIP Ventures, shares her unconventional path from international microfinance to steel manufacturing to venture capital. She discusses her seven-year tenure as interim-then-permanent CEO of a portfolio company, the firm's hands-on 'performance engineering' approach to supporting founders, and how COVID-19 transformed her company into a successful fully-remote operation.

TFTSL Excerpt—Episode 06 - To Patent or Not to Patent!

Two experienced entrepreneurs discuss the declining value of patents for venture-backed startups. They argue that spending $25-50K on patents makes little sense when those funds could accelerate market capture, patents take 5+ years to issue, and enforcement costs millions. Biotech remains an exception where patents are essential, but for most tech companies, market power through branding and network effects provides better protection than intellectual property.

TFTSL Excerpt—Episode 06 - Mike Blake's Trip to Russia

Mike Blake recounts his chaotic first trip to Russia in 1993 as a 23-year-old hired to run a USAID privatization program. After missing his flight in Frankfurt, he navigated visa complications, outdated Soviet aircraft, and ultimately accepted hospitality from self-proclaimed smugglers who helped reunite him with his contact in Minsk.

Ep 06 - Mike Blake: A Journey Through Valuations, Ventures, Visions and Vodka

Mike Blake, founder of High Score Strategies, discusses business valuation methodology, the changing landscape of patent protection, and his journey from venture capital to founding Atlanta's influential Startup Lounge networking series. He shares insights on when valuations help or hinder startup negotiations, the dramatic weakening of patent value through PTAB proceedings, and his recent relocation to Portugal.

Ep 05 - Jay Kleinman: Winning Strategies From Gridiron Grit to Healthcare Innovation

Jay Kleinman, a 30-year healthcare business development veteran, discusses his journey from playing D1 football at Auburn under Pat Dye to leading commercial strategy for early-stage healthcare companies. He shares frameworks for segmentation, discovery-based selling, and go-to-market planning, emphasizing relationship capital, authentic outreach, and the transformative potential of digital health for elder care populations.

Ep 04 - Mark Flickinger: From Rowing to Venture Capital - Lessons in Teamwork and Growth

Mark Flickinger, partner at BIP Ventures, discusses his journey from mechanical engineering and competitive rowing to venture capital. He explains BIP's platform-heavy approach with 50 employees supporting both investors and portfolio companies, their focus on high net worth LPs, and strategies for helping founders navigate the current market environment. Flickinger emphasizes the importance of solving real problems, building strong boards, and maintaining discipline during economic uncertainty.

Ep 03 - Jan Heybroek - From Startup to Successful Exit - Lessons from a Healthcare Entrepreneur

Jan Heybroek, partner at TechCXO's exec ops practice, shares his 17-year journey building and selling a medical market research company to a medical education firm in 2021. He discusses M&A negotiation tactics, the importance of transparency during due diligence, post-acquisition integration challenges, and healthcare industry trends including AI's role in diagnostics and the shift toward personalized medicine.

Ep 02 - Lewis Goldman: Mastering Marketing Evolution in the Digital Age

Lewis Goldman, a growth marketing executive at TechCXO, discusses his career evolution from advertising psychology to digital transformation across major companies like CNBC, Citigroup, and MetLife. He shares lessons from the dot-com era, explains modern marketing channel strategies including Google's lower-funnel and Meta's upper-funnel approaches, and explores how AI is reshaping both targeting capabilities and content authenticity in an influencer-saturated market.

Ep 01 - Maria Goldsholl: Building Authentic Leadership and Culture in Startups

Maria Goldsholl, fractional Chief People Officer at TXO, discusses authentic leadership, building trust-based cultures in startups, and the value of fractional executive services. She emphasizes humility over ego, the importance of going through hard things together to build team resilience, and how transparency and psychological safety drive organizational success.