AI with Bry Podcast
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 modern CTO perspective means every topic is rooted in real business needs – no fluff, no hype. Whether he’s exploring an agentic AI use case (like an AI agent for customer service) or showcasing the latest audio, video, and image generation tools, Bry always ties it back to startup strategy and practical outcomes. AI with Bry doesn’t just talk about shiny AI trends; it shows you how to use them to get results. What You’ll Learn Tune in to AI with Bry and discover how to unlock AI’s full potential for your business. In this podcast, you’ll learn about the latest AI tools for business, how to use ChatGPT and other generative AI models in your daily operations, and time-saving automation workflows powered by AI. We dive into advanced prompt engineering techniques that can make AI outputs dramatically more effective. You’ll also hear how to build and deploy AI agents to automate tasks autonomously, boosting efficiency across your organization. Beyond the tools and tech, we explore big-picture applications: AI in marketing to boost campaign performance and personalize customer engagement, AI in healthcare drawn from Bry’s firsthand experience in health tech, and the latest trends in AI in tech startups. Whether you’re a tech founder or an operations lead, AI with Bry is one of the top AI podcasts for entrepreneurs looking to stay ahead of the curve. Each episode feels like a masterclass in AI for founders and innovators at small to mid-sized companies (AI for SMBs). It’s packed with insights on startup growth with AI, improving AI productivity, and forward-looking AI strategies to give your business a competitive edge. Sample Topics & Episodes Generative AI Demystified: How to use ChatGPT and other generative AI tools to create content and solve business problems. Automation & AI Agents: Building autonomous AI agents and workflows to handle tasks like customer support, scheduling, or data analysis. AI in Marketing: Boosting your marketing campaigns and customer engagement with AI-driven insights and personalization. AI in Healthcare: How AI is improving patient care, streamlining operations, and what these innovations mean for businesses beyond healthcare. Productivity Tools for SMBs: The best AI tools for business productivity, tailored for startups and small to mid-sized companies. Interviews with AI Innovators: Candid conversations revealing real-world success stories and actionable strategies for applying AI in startups. Modern CTO Insights: How to build an AI-ready tech stack and cultivate a team culture that embraces data and automation. Ready to elevate your business with AI? Follow AI with Bry now so you never miss an episode. For deeper engagement, visit AIwithBry.com to access bonus content, resources, and more – all to help you scale smarter.
Episodes
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 execution like never before. But while AI changes how businesses are built, it does not change why people choose to invest, buy, or trust. Every ...
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 is changing more than marketing it is changing how work gets done. Many small business owners are overwhelmed managing operations, employe...
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: fragmented community information.
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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 are designed, and how leaders think about expertise. The challenge is not access to AI tools, but implementing them responsibly in ways that ...
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 of how software is produced, scaled, and optimized. The shift is no longer just faster coding, but the move from handcrafted development t...
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 care is delivered, how clinicians interact with patients, and how systems shift from reactive to proactive models. The challenge is not adop...
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, resilience, and human experience. The real challenge is alignment between innovation, trust, and human need—not capability alone. Thi...
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. This conversation reframes AI in healthcare not as external disruption, but as innovation from within—when clinicians closest to the p...
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 needed to deliver better care. This conversation reframes AI as a grassroots transformation driven by practitioners building sustainable, p...
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 process...
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, building governance into systems, and ensuring human judgment remains central as machines gain leverage. This reframes AI adoption as a...
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....
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. Organization...
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 simply making everything louder, busier, and more disposable? This conv...
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 clarity. AI does not replace judgment. It amplifies it. And without the righ...
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 longer speed alone, but clarity around what to build, why it matters, and ho...
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 alone, but responsibility, equity, and empathy. This conversation centers on ...
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 del...
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 bullet or a replacement fo...
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 teams work, decisions get made, and businesses scale. Leaders who treat AI as a teammate rather than a...
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