PODCAST · technology
AI with Bry Podcast
by Bryan Dennstedt
AI with Bry – Scale Smarter with AI Tools & Strategies AI with Bry is the go-to podcast for business leaders who want to harness the power of artificial intelligence to drive real growth. Hosted by Bryan Dennstedt, a Fractional CTO at TechCXO who scaled 45+ companies and built MDLIVE into a multibillion-dollar health tech platform, this show cuts through the hype and focuses on practical, real-world AI applications. If you’re a founder, entrepreneur, or marketer (especially at a company between $1M–$50M in revenue) looking to scale smarter, this podcast is your roadmap. Bry shares his 25+ years of technology leadership and insights so you can leverage AI tools, agents, prompts, and workflows to work smarter, not harder. Each episode delivers clear, actionable ideas to integrate AI into your business. You’ll hear creative AI prompt ideas, step-by-step automation demos, and in-depth interviews with AI experts. Bry’s m
Episodes
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Why AI Rollouts Fail After Deployment and How to Keep Them Alive w/ Katrina McCullough
💡 Deploying AI is the easy part. Getting people to trust it, use it, and build it into how they actually work — that is where most rollouts fail. In this episode, Brian speaks with Katrina McCullough, founder of McCullough Management, whose work spans ERP consolidations, digital transformation,...
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AI, Financial Services, and the Real Bottlenecks in Building with AI with Elijah Gutman
💡 AI is moving fast enough that the biggest bottlenecks are no longer the technology — they are human decisions, compliance boundaries, and the judgment required to separate real leverage from AI slop. In this episode of AI with Bry, we explore where AI is actually creating value in regulated...
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Raising Human Leaders in an AI World with Aubrey Schmalley
💡 As AI becomes embedded in classrooms, homes, and the daily lives of children, a critical question demands our attention: what are we actually doing to the developing brains of the next generation — and how do we ensure technology serves their growth rather than undermining it? In this episode…
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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 responsible innovation. AI is not simply making healthcare more efficient. It is reshaping how care is...
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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 judgment. AI is enabling founders to build products faster, automate research, and accelerate...
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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 critical lesson: building a great product is not enough if customers do not have time to use it. AI...
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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 building AI-powered systems designed to solve one of the internet’s most overlooked problems:...
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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 where trust and compliance are essential. AI is changing how organizations operate, how workflows…
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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 a founder treating software like an industrial production system. AI is becoming the core engine...
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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 geriatric and behavioral health. AI is changing not just documentation and automation, but how...
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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 and medtech advocate. AI is transforming not just software, but how industries think about scale,...
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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 advantage. The real edge comes from proximity to real problems and the willingness to solve them....
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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 technology. It is about empowering the people closest to patients with the tools, systems, and leverage...
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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 creates chaos. The real work for leaders is not just adopting tools—it is defining processes,...
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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 intention creates fragility. The challenge for leaders is not adopting tools—it is defining values,...
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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 mergers and acquisitions. AI is no longer a novelty inside organizations. It is a force multiplier....
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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 happens when AI shifts from being an efficiency tool to becoming a true force multiplier. Organizations...
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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 are increasingly wrestling with a deeper question. Is moving faster actually making work better, or...
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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 teams work, the difference between success and chaos comes down to leadership, structure, and...
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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. As AI accelerates development cycles and lowers execution barriers, the real advantage is no…
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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 health. As AI accelerates innovation, the real challenge for leaders is not speed or scale…
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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 can afford to ignore or delegate away. The divide is growing between leaders who are actively...
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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 education, workflow design, leadership judgment, and human-centered execution. AI is not a silver...
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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, process, and clarity. AI is not just a shiny new tool. It is quickly becoming a core part of how...
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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 separation between “product” and “growth” is collapsing and the leaders who understand data and AI will…
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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 superintelligence and reshapes the global economy, we explore whether conscious machines could actually be the…
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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 agentic AI. I’m joined by Brooks Morrison, Principal Product Leader at TechCXO, who brings 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 without gutting their teams. Christine has spent two decades guiding leaders through change. Today,...
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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 and Stoic philosopher joins me for a conversation across time to explore how his timeless...
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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, fintech, telco, and insurance, Federico shows how leaders turn messy data and vague AI goals into...
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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 the force behind the Bureau of Creative Intelligence — to explore how leaders can “remaster fire”:...
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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 (Partner at TechCXO) to explore how his Revenue Growth Agent (RGA) uses AI to: ⚡ Automate pre-call...
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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 Results In this episode of AI with Bry, I sit down with Sarah Cornett — founder & CEO of Global AI Advisors — to unpack why 80–90% of AI projects fail, and how leaders can flip the script by turning AI strategy into measurable business...
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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 transforming real business operations, from cutting costs to scaling training. 🏢 How AI strengthens insurance training by...
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Can AI Make Us More Human? Creativity, Culture, and Collective Intelligence with Mason Youngblood
Collective Intelligence, Creativity & The New AI Renaissance In this episode of AI with Bry, I sit down with Mason Youngblood—researcher, musician, and co-lead of the Collective Creativity Lab at Stony Brook University—to explore how AI is reshaping creativity, collaboration, and cultural...
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AI Is Not Just a Tool: Why This Tech Wave Challenges Our Purpose
Human Purpose, Leadership & the Future of AI In 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 just how we work, but why. 🌍 The 3 groups reacting to AI → ethics, resistance, and planetary…
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The Future of Creativity: Pete Sena on AI and Branding
Creativity, Storytelling & the Future of AI In 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 think, create, and grow businesses: 🎨 How AI is changing the creative process ⚡ Why the pace of AI progress is...
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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 Reality Welcome back to AI with Bry, the show where I help founders, executives, and innovators learn, leverage, and lead with AI. In this episode, I sit down with Kevin Carlson, a four-time CTO, former...
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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 Ziemniak Welcome back to AI with Bry — the show where we help founders, executives, and innovators learn, leverage, and lead with AI. In this episode, host Bryan Dennstedt is joined by Terry Ziemniak, former Chief Risk Officer,...
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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 Merrill Welcome to the very first episode of AI with Bry — the show where we help founders, executives, and innovators learn, leverage, and lead with AI. In this kickoff conversation, Bryan Dennstedt is joined by long-time...
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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 productivity without doubling your headcount, why it's as essential as water for modern companies…
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ABOUT THIS SHOW
AI with Bry – Scale Smarter with AI Tools & Strategies
AI with Bry is the go-to podcast for business leaders who want to harness the power of artificial intelligence to drive real growth. Hosted by Bryan Dennstedt, a Fractional CTO at TechCXO who scaled 45+ companies and built MDLIVE into a multibillion-dollar health tech platform, this show cuts through the hype and focuses on practical, real-world AI applications. If you’re a founder, entrepreneur, or marketer (especially at a company between $1M–$50M in revenue) looking to scale smarter, this podcast is your roadmap. Bry shares his 25+ years of technology leadership and insights so you can leverage AI tools, agents, prompts, and workflows to work smarter, not harder.
Each episode delivers clear, actionable ideas to integrate AI into your business. You’ll hear creative AI prompt ideas, step-by-step automation demos, and in-depth interviews with AI experts. Bry’s m
HOSTED BY
Bryan Dennstedt
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How many episodes does AI with Bry Podcast have?
AI with Bry Podcast currently has 41 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is AI with Bry Podcast about?
AI with Bry – Scale Smarter with AI Tools & Strategies AI with Bry is the go-to podcast for business leaders who want to harness the power of artificial intelligence to drive real growth. Hosted by Bryan Dennstedt, a Fractional CTO at TechCXO who scaled 45+ companies and built MDLIVE into a...
How often does AI with Bry Podcast release new episodes?
AI with Bry Podcast has 41 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to AI with Bry Podcast?
You can listen to AI with Bry Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts AI with Bry Podcast?
AI with Bry Podcast is created and hosted by Bryan Dennstedt.
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