AI strategy that survives contact with reality
The frameworks for picking what to ship, what to ignore, and how to tell the difference when every vendor is pitching the same demo.
Podcast
AI with Bry
There's never been a better time to understand how AI shapes our world.
Stop guessing. Start leading with AI. Bryan Dennstedt sits down with founders, operators, and technologists working at the edge of AI to break down what's actually working, and what's just hype.
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Why listen
What you'll walk away with
Leadership patterns from the front lines
Founders, CTOs, and operators sharing what's working, and what's quietly burning cash, in healthcare, fintech, sustainability, and beyond.
The honest take on what AI changes
Beyond the productivity demos: what AI actually does to org structure, hiring, product roadmap, and the way teams make decisions together.
Latest episode
How AI Is Changing Entrepreneurship, Investing, and Decision-Making
🎙️ Welcome to AI with Bry – Learn. Leverage. Lead.You’re listening to the show that helps founders, operators, and marketers unlock the full potential of AI in real business settings. Hosted by Bry Dennstedt — Fractional CTO at TechCXO and founding technologist behind MDLIVE’s early growth — this podcast gives you ins…
All 39 episodes
Why AI Doctors Could Solve Healthcare’s Biggest Workforce Crisis
In this episode of AI with Bry, we explore how artificial intelligence is transforming healthcare through the lens of one of the industry's leading voices on digital health, health equity, and respons…
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How Financial Services Leaders Can Adopt AI Without Creating Compliance Disasters
In this episode of AI with Bry, we explore how artificial intelligence is transforming entrepreneurship, investing, and business strategy through one constant that technology cannot replace: human jud…
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How Missed Follow-Ups Are Costing Home Service Businesses Thousands Every Month
In this episode of AI with Bry, we explore how artificial intelligence is transforming small business growth, customer acquisition, and service delivery through the story of a founder who learned a cr…
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The Smartest AI Infrastructure Idea Most Cities Are Missing
In this episode of AI with Bry, we explore how artificial intelligence is reshaping community infrastructure, local discovery, civic engagement, and economic development through the lens of a founder …
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How Financial Services Leaders Can Adopt AI Without Creating Compliance Disasters
In this episode of AI with Bry, we explore how artificial intelligence is reshaping financial services, AI implementation strategy, and the future of white-collar work through regulated industries whe…
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Why Software is No Longer Written It's Produced Like a Factory
In this episode of AI with Bry, we explore how artificial intelligence is reshaping software development, enterprise delivery models, and the economics of building digital products through the lens of…
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How a Nurse Practitioner is Rebuilding Geriatric Care with AI from the Ground Up
In this episode of AI with Bry, we explore how artificial intelligence is reshaping healthcare delivery, clinician experience, and proactive care models through the lens of a clinician entrepreneur in…
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Why AI is Making Healthcare Faster But Not Better for Patients
In this episode of AI with Bry, we explore how artificial intelligence is reshaping healthcare, infrastructure thinking, and human-centered technology through the lens of a veteran technology leader a…
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How a Resident Physician Building AI to Fix Broken Healthcare Contracts
In this episode of AI with Bry, we explore what happens when clinical expertise meets entrepreneurial execution in the age of AI.AI is lowering the barrier to building, but access alone is not the adv…
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How AI is Empowering Nurse Practitioners to Rebuild Healthcare
In this episode of AI with Bry, we explore how artificial intelligence is reshaping healthcare through the lens of nurse practitioner entrepreneurs.AI adoption in healthcare is not just about technolo…
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Busy Sales Teams vs Real Revenue Engines
In this episode of AI with Bry, we explore leadership at the intersection of artificial intelligence and revenue growth.AI is accelerating execution across every function. But speed without structure …
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AI Isn’t the Threat Leadership Is
In this episode of AI with Bry, we explore leadership at the intersection of artificial intelligence and moral architecture.AI is accelerating execution across every function, but speed without intent…
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Is AI Replacing Developers Or Upgrading Them
In this episode of AI with Bry, we explore how leaders move beyond AI experimentation and into real execution, especially in high stakes environments like technology diligence, private equity, and mer…
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Escape Velocity: How AI Is Replacing Research and Reshaping Execution
In this episode of AI with Bry, we explore how AI is fundamentally reshaping research, product strategy, and execution. The conversation moves beyond surface level experimentation and into what happen…
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From Strategy to Execution: Leading with AI Without Losing Judgment
In this episode of AI with Bry, we explore the widening gap between strategy and execution as AI accelerates how work gets done across organizations. While AI promises speed and efficiency, leaders ar…
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AI as a Leadership Lever: Driving Real Impact
In this episode of AI with Bry, we explore how leaders can turn AI from a noisy buzzword into real operational leverage. As AI accelerates product development, compresses timelines, and reshapes how t…
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Leverage Over Tools: How Product Leaders Actually Win with AI
In this episode of AI with Bry, we explore why winning with AI has far less to do with chasing the latest tools and far more to do with how leaders think about leverage, systems, and decision making. …
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Lead with Trust: AI, Community, and Health Equity in Women’s Mental Health
In this episode of AI with Bry, we explore what it means to lead with trust in an era where AI is rapidly entering some of the most sensitive and human centered spaces, including healthcare and mental…
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The AI Divide in 2025: Leaders Who Learn Fast vs. Those Who Fall Behind
In this episode of AI with Bry, we explore what leadership really looks like in 2025 as AI rapidly reshapes how work gets done, teams operate, and businesses compete. AI is no longer something leaders…
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The Unsexy AI Revolution: Where Real Value Actually Comes From
In this episode of AI with Bry, we explore the unsexy but transformational reality of AI adoption and why real value does not come from hype, headlines, or flashy demos, but from fundamentals like edu…
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Lead by Example: AI as a Tool, Process, and Team Member
In this episode of AI with Bry, we explore what it really means to lead by example in the age of AI and why successful adoption has far less to do with age or titles and far more to do with curiosity,…
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Build, Grow, Repeat: Data-Literate Leadership in the Age of AI
In this episode of AI with Bry, we explore what happens when AI doesn’t just speed up your workflows, but completely rewires how you build products, grow your business, and lead your team. The separat…
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Conscious Machines, Safer Futures: Calum Chace on AI, Work, and What Comes Next
In this episode of AI with Bry, we wrestle with one of the biggest questions of our time: what happens when machines don’t just out-think us, but maybe even wake up? As AI races toward superintelligen…
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Ship in Days, Not Months: Agentic AI for Product Managers with Brooks Morrison
In this episode of AI with Bry, we explore a shift that’s happening faster than anyone expected: product teams are beginning to ship in days, not months. And the catalyst behind this acceleration is a…
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Beyond Headcount Cuts: Scale with AI and Keep Your People
Layoffs aren’t a strategy. In this episode of AI with Bry, I sit down with Christine Santacroce, a people-first leader and transformation expert, to show how companies can scale profitably with AI wit…
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Marcus Aurelius on AI: Ancient Wisdom for the Age of Algorithms
Two thousand years ago, Marcus Aurelius wrote Meditations. Reflections on wisdom, virtue, and leadership that still guide millions today. Now, in this special episode of AI with Bry, the Roman Emperor…
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Data Before Models: Turning AI into Business Outcomes
Most teams ask, “Which model should we use?” Federico Nagy (Co-founder, WayToGo Data) flips it: start with the problem, fix the data, then choose the tech. With 10+ years across healthcare, banking, f…
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Remastering Fire: Leading Creative Teams in the Age of AI
Most AI talks chase hype and tools. This one is about leadership, creativity, and change.In this episode of AI with Bry, I sit down with Vincent Hunt — Founder & CEO of Frontier Technologies and t…
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Revenue Growth Agent: Pre-Call Research to Proposal in Minutes - Matt Oess
Revenue Growth Agent: Pre-Call Research to Proposal in Minutes. Most sales teams spend 30–60 minutes prepping for a call… then wing it. In this episode of AI with Bry, I sit down with Matt Oess (Partn…
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Why AI Projects Fail—and How Leaders Turn Strategy into Results with Sarah Cornett
Why AI Projects Fail—and How Leaders Turn Strategy into ResultsIn this episode of AI with Bry, I sit down with Sarah Cornett — founder & CEO of Global AI Advisors — to unpack why 80…
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3 Real Business Wins with AI (Insurance, SEO, Training) with Justin Goodman
3 Real Business Wins with AI (Insurance, SEO, Training)In this episode of AI with Bry, I sit down with Justin Goodman — co-founder & CEO of Total CSR — to explore how AI is transfor…
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Can AI Make Us More Human? Creativity, Culture, and Collective Intelligence with Mason Youngblood
Collective Intelligence, Creativity & The New AI RenaissanceIn this episode of AI with Bry, I sit down with Mason Youngblood—researcher, musician, and co-lead of the Collective Creativit…
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AI Is Not Just a Tool: Why This Tech Wave Challenges Our Purpose
Human Purpose, Leadership & the Future of AIIn this episode of AI with Bry, I sit down with Virginie Glaenzer—fractional CMO, advisor, and host of Pass the Mic—to explore how AI is reshaping not j…
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The Future of Creativity: Pete Sena on AI and Branding
Creativity, Storytelling & the Future of AIIn this episode of AI with Bry, I sit down with entrepreneur and creative strategist Pete Sena to unpack how AI is transforming the way we…
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AI & Cybersecurity: How Kevin Carlson is Guiding Leaders Through the Hype and the Reality
🎙️ S1:E3 — AI & Cybersecurity: How Kevin Carlson is Guiding Leaders Through the Hype and the RealityWelcome back to AI with Bry, the show where I help founders, executives, and innovato…
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AI Risk & Strategy: What Every Executive Must Know in 2025
🎙️ S1:E2 — Trust, Risk & Responsible AI: A Strategy Guide with Terry ZiemniakWelcome back to AI with Bry — the show where we help founders, executives, and innovators learn, leverage, a…
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Claude, MCP & the Future of Work: Deep Dive with Todd Merrill
🎙️ S1:E1 — Claude, MCP & The Future of Work: Deep Dive with Todd MerrillWelcome to the very first episode of AI with Bry — the show where we help founders, executives, and innovators le…
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Stop Guessing. Start Leading with AI – Welcome to AI with Bry
Welcome to AI with Bry. The podcast where startup founders and CEOs learn how to actually use AI to grow their business. In this kickoff episode, host Bryan Dennstedt shares how AI can double your pro…
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Want on the show?
I book guests who've actually shipped something with AI, not just slides about it. Founders, CTOs, operators, clinicians, anyone who's wrestled a real outcome out of a real implementation.
Good fits:
- You've built or led an AI initiative in a real production environment
- You can talk about specific decisions and trade-offs, not just success stories
- You're operating in regulated or high-stakes industries (healthcare, fintech, sustainability)
- You have a concrete story about something that worked, or something that broke, and what you learned
Hosted by
Bryan Dennstedt
Fractional CTO, AI strategist, and 28-year veteran of shipping software in regulated industries. Bryan started AI with Bry to share what boardroom conversations about AI actually sound like when there's a customer on the line and a P&L on the table.
He works with founders and exec teams across healthtech, fintech, and sustainability, the same operators he interviews on the show.