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AI with Bry Podcast

AI with Bry Podcast

By: Bryan Dennstedt
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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.

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Episodes
  • AI as a Leadership Lever: Driving Real Impact

    AI as a Leadership Lever: Driving Real Impact
    Jan 30 2026
    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 right controls, it can just as easily magnify confusion as it can performance.I am joined by Paul King, Principal at Tech CXO, where he works hands on with founders, CEOs, and executive teams to bring operational discipline, scalable systems, and execution clarity to growing organizations. Paul has spent his career helping companies move from ambition to reality, making him uniquely positioned to cut through AI hype and focus on what actually works inside real teams.Paul and I unpack what leaders often misunderstand about large language models, why AI is not “thinking” but still incredibly powerful, and why context and control matter more than speed. We explore real examples of hallucinations, fabricated features, and misleading outputs, not as reasons to avoid AI, but as reasons leaders must stay engaged and intentional. This conversation dives into how AI fits into product development, architecture decisions, testing, and quality assurance, and why the role of developers is shifting from writing code to guiding, validating, and structuring systems.We also discuss how effective AI leverage goes far beyond small productivity gains. From autonomous coding agents and parallel development to better visibility for executives and stronger accountability across teams, this episode shows how AI can transform how organizations operate when leaders rethink processes instead of just installing tools. Paul shares why companies that refuse to engage with AI will fall behind, and why those that only use it as a chatbot are leaving massive value on the table.Whether you are a founder, executive, or technology leader trying to navigate AI adoption without losing control, this episode will help you think more clearly about leverage, leadership, and how to build organizations that can move faster without breaking themselves in the process.What You Will Learn in This EpisodeWhy AI is not thinking and why that distinction mattersHow hallucinations happen and how leaders should manage themWhy context and framing determine AI output qualityHow AI is changing the role of developers and engineersWhy leverage is about systems, not shortcutsHow leaders can gain real visibility into product developmentWhy junior and senior talent must learn AI differentlyHow autonomous agents accelerate development cyclesWhy small productivity gains are not real AI leverageHow leadership decisions determine whether AI creates growth or chaosResources, Tools and Platforms MentionedAI Models and PlatformsChatGPT https://chat.openai.comClaude https://claude.aiGemini https://gemini.google.comDeveloper and Coding ToolsClaude Code https://www.anthropic.com/news/claude-codeGitHub Copilot https://github.com/features/copilotCursor https://www.cursor.shAdvisory and LeadershipTech CXO https://techcxo.comWatch and Follow AI with BryFull episodes and show notes https://bry.net/aiYouTube https://www.youtube.com/@aiwithbryInstagram https://www.instagram.com/aiwithbryFacebook https://www.facebook.com/profile.php?id=61575757332333TikTok https://www.tiktok.com/@aiwithbryRemember, the tools will keep changing. Strong leadership never goes out of style. Learn, leverage, and lead.
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    32 mins
  • Leverage Over Tools: How Product Leaders Actually Win with AI

    Leverage Over Tools: How Product Leaders Actually Win with AI
    Jan 24 2026
    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 how teams use AI to fundamentally change how work gets done.I am joined by Anu Ram, a fractional product leader and advisor working with organizations across industries to help them navigate AI driven change with intention. Anu brings deep experience spanning product strategy, execution, and organizational design, including her work with Crux Partners and Parsons AI. Her perspective is rooted in real operator challenges, not theory, and focuses on how leaders and teams actually build better products in practice.Anu and I unpack why AI should be invited into everything, but never left to run unchecked. We discuss why context is the real unlock for AI usefulness, why leaders must remain firmly in the human in the loop, and how trust is built by asking AI to show its work rather than blindly accepting outputs. From rapid prototyping and proof of concepts to workflow automation, security reviews, and internal decision making, this conversation highlights how AI creates true leverage when paired with strong product judgment.We also explore how AI is reshaping the role of product teams as development cycles shrink and vision, prioritization, and customer understanding become the new bottlenecks. Anu shares practical examples of how leaders can start small, codify tribal knowledge, and create space for experimentation without creating chaos. The episode reinforces why leverage should be rewarded as much as output, and why leadership in the AI era means modeling curiosity, restraint, and intentional adoption.Whether you are a product leader, founder, executive, or operator trying to move beyond surface level AI adoption, this episode will help you rethink AI as a force multiplier for strategy, not a replacement for thinking.What You Will Learn in This EpisodeWhy leverage matters more than tools in AI driven organizationsWhy context is the most important input leaders can give AIHow to stay human in the loop while still moving fasterWhy AI accelerates good product thinking and exposes weak strategyHow rapid prototyping changes product discovery and validationWhy workflows, not moonshots, are the best place to start with AIHow AI helps surface insights across sales, support, and customer dataWhy leaders must reward leverage, not just outputHow governance and experimentation must coexist in larger organizationsWhy inviting AI to everything starts with curiosity, not expertiseResources and Organizations MentionedCrux Partners https://cruxpartners.coParsanAI https://www.parsan.ai/AI Models and AssistantsChatGPT: https://chat.openai.comClaude: https://www.anthropic.com/claudePerplexity: https://www.perplexity.aiVibe Coding and Agentic DevelopmentAI-assisted prototyping: https://www.anthropic.com/researchAgentic workflows for product, research, and operations: https://www.microsoft.com/en-us/research/blog/ai-agents-explainedProduct and Leadership ConceptsHuman-in-the-loop systems: https://www.nist.gov/itl/ai-risk-management-frameworkContext-driven product discoveryLeverage over automationWatch and Follow AI with BryFull episodes and show notes https://bry.net/aiYouTube https://www.youtube.com/@aiwithbryInstagram https://www.instagram.com/aiwithbryFacebook https://www.facebook.com/profile.php?id=61575757332333TikTok https://www.tiktok.com/@aiwithbryRemember, the future does not wait. Learn, leverage, and lead.
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    28 mins
  • Lead with Trust: AI, Community, and Health Equity in Women’s Mental Health

    Lead with Trust: AI, Community, and Health Equity in Women’s Mental Health
    Jan 18 2026
    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 how AI can support outcomes without reinforcing bias or losing sight of the people it is meant to serve.I am joined by Sheila Pande, CEO of Tandem, a company focused on improving maternal mental health outcomes through trust, community, and culturally responsive care. Sheila brings a rare combination of public health training, systems thinking, and hands on leadership as she builds technology designed to reduce racial disparities while integrating responsibly into real healthcare workflows.Sheila and I unpack how AI is already shaping healthcare decisions and why leaders must understand the limits of data, especially in women’s health and communities that have historically been underrepresented in research. We discuss how bias shows up in AI outputs, why context and prompting matter, and how leaders can engage AI thoughtfully without assuming it is neutral or complete. From building complex healthcare platforms through agentic and vibe coding to rethinking how data, governance, and trust intersect, this episode offers a grounded look at what responsible AI adoption really looks like.We also explore how AI is compressing development timelines, lowering costs, and creating entirely new leadership and operational roles, while still requiring strong human judgment. Sheila shares how AI is being leveraged across product development, marketing, business development, and healthcare delivery, all while keeping equity and outcomes at the center.Whether you are a healthcare leader, founder, nonprofit executive, or builder navigating AI in high stakes environments, this episode will challenge you to rethink leadership as the ability to ask better questions, design better systems, and use AI in service of people rather than performance metrics alone.What You Will Learn in This EpisodeWhy AI reflects the gaps and biases of existing healthcare dataWhy trust and context matter more than automation in healthcare AIHow AI can reinforce or reduce inequity depending on leadership choicesWhy leaders must understand AI systems, not just delegate themHow agentic and vibe coding are compressing development timelines dramaticallyWhy healthcare AI requires governance, not just policyHow AI is changing hiring models and creating entirely new rolesWhy human judgment remains essential in AI driven health systemsHow AI can lower costs and unlock access to underserved populationsWhy ethical leadership starts with admitting what you do not yet understandResources, Tools and Platforms MentionedAI Models and PlatformsChatGPT https://chat.openai.comClaude https://claude.aiHealthcare and TechnologyTandem http://beintandem.coConnect with Sheila PandeTandem: https://beintandem.co/LinkedIn: https://www.linkedin.com/in/sheilapande/Watch and Follow AI with BryFull episodes and show notes https://bry.net/aiYouTube https://www.youtube.com/@aiwithbryInstagram https://www.instagram.com/aiwithbryFacebook https://www.facebook.com/profile.php?id=61575757332333TikTok https://www.tiktok.com/@aiwithbryRemember, the future does not wait. Learn, leverage, and lead.
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    34 mins
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