LEARN. LEVERAGE. LEAD
Empowering you with AI
Business owners share how they’re using AI
to overcome challenges and build smarter,
scalable companies.
LEARN. LEVERAGE. LEAD
Empowering you to Learn, Leverage, and Lead with AI
— Fractional CTO’s for forward-moving companies.
Driven business owners share their transformational journey into the world of AI — how they’re leveraging emerging tech, overcoming
real-world challenges, and shaping the future of smart,
scalable companies.
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Podcast Episodes
S1:Ep26: AI Isn’t the Threat Leadership Is
On AI with Bry, I sat down with , founder of and Chief Philosophy Officer. Cristina has spent over 25 years in technology, digital strategy, and organizational leadership. She combines operational expertise with a deep grounding in philosophy, helping leaders embed moral reasoning and ethical frameworks into AI adoption. Her work centers on guiding teams through change, ensuring technology is leveraged responsibly, and translating AI’s capabilities into practical human-centered execution.
S1:Ep25: Grassroots AI: Why Top Down Rollouts Fail
On AI with Bry, I sat down with Greg Smith, Managing Partner of the Product and Technology Practice at TechCXO. Greg leads a team of fractional CTOs, CIOs, CPOs, CISOs, and senior technology operators who work directly with growth-stage companies and investors. With decades of experience across product, M&A, turnarounds, and deep technical diligence, Greg brings a grounded perspective to how AI is reshaping both company execution and investment risk assessment.
S1:Ep24: Escape Velocity: How AI Is Replacing Research and Reshaping Execution
On AI with Bry, I sat down with Danny Mendoza from Escape Velocity, alongside Michael Heiser and Elijah Gutman. Together, they are working at the intersection of innovation, capital, culture, and execution. Their mission is simple but powerful. Help early stage companies break free from the gravity of slow execution and bring real ideas to market faster.
S1:Ep23: From Strategy to Execution: Leading with AI Without Losing Judgment
On AI with Bry, I sat down with Michael Baer, a fractional Chief Marketing Officer and Chief Growth Officer with Tech CXO, to unpack what it really means to bridge strategy and execution in an AI enabled organization. Michael brings a grounded operator’s perspective. He does not see AI as a shiny sticker to slap on a product. He sees it as a tool that must serve outcomes, not ego.
S1:Ep22: AI as a Leadership Lever: Driving Real Impact
Learning how to lead with AI is no longer about understanding how large language models work under the hood. It is about knowing how to apply them with discipline, structure, and intent. In a world where AI can generate code, analyze systems, and accelerate execution at unprecedented speed, leadership has become the real constraint. The difference between success and failure is no longer access to tools. It is clarity of direction.
S1:Ep21: Stop Chasing AI Tools. Build Leverage, Context, and Faster Product Cycles
Learning to lead with AI is no longer about finding the next shiny tool or memorizing the perfect prompt. The real advantage comes from changing how you think about work itself. Context, clarity, and leverage matter far more than which model you are using this week. As AI compresses development cycles and accelerates execution, leadership in product and technology is being redefined in real time.
S1:Ep18: Lead with Trust: AI, Community, and Health Equity in Women’s Mental Health
Learning how to lead with AI in healthcare is not about chasing the newest model or automating everything in sight. The real work is understanding where technology helps, where it falls short, and how to design systems that protect trust, equity, and human dignity. In spaces like maternal mental health, leadership demands more than efficiency. It requires context, accountability, and care.
S1:Ep19: The AI Divide in 2025: Leaders Who Learn Fast vs. Those Who Fall Behind
AI is moving too fast for anyone to feel fully caught up, and that reality applies to everyone, from first time managers to seasoned executives. The leaders who are pulling ahead are not the ones who know the most about AI. They are the ones willing to learn continuously, apply it intentionally, and rethink how work actually gets done.
S1:Ep18: The Unsexy AI Revolution: Where Real Value Actually Comes From
The real AI revolution is not flashy. It is not about the newest model, the loudest headline, or the cleverest prompt. It is about work. Real work. The kind that happens inside teams, across processes, and within organizations that want to scale responsibly.
S1:Ep17: Lead by Example: AI as a Tool, Process, and Team Member
Learning how to lead with AI is no longer about knowing the newest tool or the most advanced prompt. The real shift is understanding how to think clearly about work, break it into steps, and design systems where AI can actually contribute.
S1:Ep16: Build, Grow, Repeat: Data-Literate Leadership in the Age of AI
Learning has changed forever. We no longer have to memorize every framework or master every tool by hand. Now the real skill is knowing what to ask, how to plan, and how to turn AI into arms and legs for your ideas.
S1:Ep15: Conscious Machines and the Future of Work: Calum Chace on AI, Meaning, and What Comes Next
For author, futurist, and AI safety leader Calum Chace, the path forward requires more than clever models and faster chips. It demands a clear-eyed look at the systems we’re building, the wealth they’ll create, and the humanity we risk losing or rediscovering in the process.
S1:Ep14: Ship in Days, Not Months: Agentic AI for Product Managers
What if product managers could ship in days, not months and keep up with developers who are now moving 5–10x faster with AI? In this episode of AI with Bry, I sit down with Brooks Morrison, Principal Product Leader at TechCXO, to explore how Agentic...
S1:Ep13: Scale with AI, Without Losing Your Team
AI is reshaping work, but not in the way most leaders think. This episode of AI with Bry dives into how organizations can scale faster, improve productivity, and build healthier cultures, without relying on layoffs. I’m joined by Christine SantaCross, a people-first leader...
S1:Ep12: Marcus Aurelius on AI & Modern Leadership
What would a Roman Emperor say about artificial intelligence? In this special episode of AI with Bry, I sit down with Marcus Aurelius, the Stoic philosopher and author of Meditations, to explore how ancient wisdom can guide modern leaders through the age...
S1:Ep11: Data Before Models: Turning AI into Business Outcomes
Up to 85% of AI projects never reach ROI — not because the models fail, but because the data and strategy behind them do. In this episode of AI with Bry, I sit down with Federico Nagy, Co-Founder of WayToGo Data, to explore how leaders...
S1:Ep10: Remastering Fire: Leading Creative Teams in the Age of AI
Up to 85% of AI projects stall before they ever deliver ROI. The gap isn’t just about technology—it’s about leadership, creativity, and guiding people through change.In this episode of AI with Bry, I talk with Vincent Hunt, Founder & CEO of...
S1:Ep9: Revenue Growth Agent: Pre-Call Research to Proposal in Minutes
Up to 85% of AI projects never hit ROI. The gap isn’t about models or hype—it’s about turning experimentation into measurable business outcomes. In this episode of AI with Bry, I talk with Matt Oess, Partner at TechCXO, about moving...
S1:Ep8: Why AI Projects Fail—and How Leaders Turn Strategy into Results
80–90% of AI projects fail to deliver value. Why? Because too many leaders chase shiny tools instead of aligning AI with strategy, governance, and people. In this episode of AI with Bry, I sit down with Sarah Cornett...
S1:Ep7: 3 Real Business Wins with AI (Insurance, SEO, Training) - with Justin Goodman
In this episode of AI with Bry, I sit down with Justin Goodman to explore three real-world business wins with AI across insurance, SEO, and employee training. Discover practical AI implementations...
S1:E6: Can AI Make Us More Human? Creativity, Culture, and Collective Intelligence
On AI with Bry, Mason shared how AI is sparking a new era in art and music, why attribution and ethics must evolve with technology, and how leaders, educators, and creators can embrace AI as a co-creator.
S1:E5: AI Is Not Just a Tool: Why This Tech Wave Challenges Our Purpose
In this episode of AI with Bry, I sit down with Virginie Glaenzer (Fractional CMO, advisor, author, and host of Pass the Mic) to unpack how AI is transforming business, leadership, and society.
S1:E4: The Future of Creativity: Pete Sena on AI and Branding
In this episode of AI with Bry, I sit down with Pete Sena — entrepreneur, strategist, and founder of Digital Surgeons — to explore how AI is transforming creativity and leadership.
S1:E3: AI & Cybersecurity: How Kevin Carlson is Guiding Leaders Through the Hype and the Reality
In this episode, host Bryan Dennstedt talks with Kevin Carlson — four-time CTO, former CISO, and Tech CXO advisor — about the real-world intersection of AI and cybersecurity, and how to separate value from hype.
S1:E2: AI Risk & Strategy: What Every Executive Must Know in 2025
In this episode, host Bryan Dennstedt sits down with Terry Ziemniak — former Chief Risk Officer, cybersecurity expert, and Tech CXO advisor — to unpack one of the most urgent but often overlooked challenges in AI: trust, governance, and responsible strategy.
S1:E1: Claude, MCP & The Future of Work: Deep Dive with Todd Merrill
In the first episode of AI with Bry, I talk with AI expert Todd Merrill about real-time AI evolution—from agent-based systems to Claude's capabilities and instant proposals. A must-listen for leaders ready to leverage AI.
Stop Guessing. Start Leading with AI – Welcome to AI with Bry
This kickoff episode of AI with Bry shows startup founders how to use AI to boost productivity, cut costs, and gain a competitive edge—no extra hires needed.
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Meet The Host
Bryan Dennstedt is a seasoned tech executive, AI strategist, and Fractional CTO helping mission-driven startups scale smarter. As the host of AI with Bry, he blends two decades of engineering leadership with a deep curiosity for emerging technology — especially AI's practical and ethical impact on business. With a background in building high-performing teams and digital platforms, Bryan now guides founders, investors, and operators through the rapidly evolving AI landscape. His mission: make advanced tech accessible, actionable, and aligned with values. Through his content and advisory work, he’s helping shape a future where innovation drives meaningful, measurable change.
Meet The Host
Bryan Dennstedt is a seasoned tech executive, AI strategist, and Fractional CTO helping mission-driven startups scale smarter. As the host of AI with Bry, he blends two decades of engineering leadership with a deep curiosity for emerging technology — especially AI's practical and ethical impact on business. With a background in building high-performing teams and digital platforms, Bryan now guides founders, investors, and operators through the rapidly evolving AI landscape. His mission: make advanced tech accessible, actionable, and aligned with values. Through his content and advisory work, he’s helping shape a future where innovation drives meaningful, measurable change.
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Learn. Leverage. Lead.
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GET IN TOUCH
Fractional CTO | AI Strategist | Sustainable Tech Advocate & Investor
Learn. Leverage. Lead.