AI with Bry Podcast

Bryan Dennstedt
  • 5.0 (2)
  • Technology
  • Updated Weekly

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.

  1. The Smartest AI Infrastructure Idea Most Cities Are Missing

    May 29

    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: fragmented community information. AI is not just changing enterprise workflows or automating productivity. It is fundamentally changing how communities organize culture, distribute information, support local businesses, and help residents discover what is happening around them. But as this conversation reveals, the biggest challenge is not a lack of events, culture, or entrepreneurship—it is the absence of infrastructure capable of connecting and distributing that information effectively in the AI era. This episode reframes AI adoption through the realities of community fragmentation, digital infrastructure, local economic development, tourism ecosystems, cultural discovery, and the growing shift from traditional websites toward AI-driven information discovery systems. What You Will Learn in This EpisodeWhy many communities suffer from fragmented digital infrastructureThe difference between community activity and community discoverabilityHow AI-powered search is changing local information discoveryWhy traditional website traffic strategies are becoming less effectiveThe importance of structuring information for AI consumptionHow CivicLift functions as an “MLS for local culture”Why collaboration matters more than siloed digital systemsHow AI accelerates product development for lean teamsThe role of AI agents and research systems in community mappingHow AI-powered workflows reduce operational overheadWhy small teams can now build enterprise-level software systemsThe future of AI-driven local recommendations and itinerary systemsHow AI can surface cultural trends and economic insights automaticallyWhy infrastructure matters more than marketing aloneThe leadership lessons behind long-term customer-driven product developmentHow AI may reshape tourism, economic development, and civic engagementResources, Tools and Platforms MentionedCivicLift https://civiclift.com Get CivicLift https://get.civiclift.com Claude https://claude.ai ChatGPT https://chatgpt.com Gemini https://gemini.google.com Fireflies AI https://fireflies.ai Watch and Follow AI with BryFull episodes and show notes https://bry.net/ai YouTube https://www.youtube.com/@aiwithbry Instagram https://www.instagram.com/aiwithbry Facebook https://www.facebook.com/profile.php?id=61575757332333 TikTok https://www.tiktok.com/@aiwithbry The future of AI-driven communities will not belong to the towns or organizations that simply create more content. It will belong to the communities that build the infrastructure capable of organizing, distributing, and activating local culture at scale. Learn, leverage, and lead.

    33 min
  2. How Financial Services Leaders Can Adopt AI Without Creating Compliance Disasters

    Apr 29

    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 are designed, and how leaders think about expertise. The challenge is not access to AI tools, but implementing them responsibly in ways that solve real problems without introducing risk. This episode reframes AI adoption through compliance-heavy industries, operational complexity, and the gap between using AI and redesigning workflows around it. Guest: Elijah Gutman Elijah Gutman is Founder and CEO of Hartford AI Partners, an AI implementation consultancy serving financial services, insurance, venture capital, and wealth management. He also serves as AI Product Strategist at UEmergence, a FINRA-registered broker dealer, where he helped design compliant AI-driven due diligence systems for private markets. His approach is practical: AI should reduce friction, improve operations, and enhance human expertise—not replace leadership. We explore how AI adoption is moving from experimentation to operational transformation. Most companies are still in the early stage of using AI for simple tasks and have not redesigned workflows or systems around it. A key theme is layered adoption: organizations must first integrate AI into daily workflows like documentation, task management, and knowledge systems before scaling into automation and agents. AI is already compressing product development by automating interviews, requirements, task breakdowns, and engineering prep—reducing weeks of work into hours. Implementation is less a technical challenge and more an organizational one involving leadership, workflow design, and system thinking. We also discuss compliance in financial services. Many AI tools are not built for FINRA/SEC requirements like audit trails and traceability, creating real risk if deployed without expertise. A major theme is “trust as the product.” In regulated industries, the value of AI is safe, reliable execution—not just efficiency. We explore the future of work (“The Great Reshuffling”), where AI democratizes cognitive capability and shifts hiring toward adaptability, systems thinking, and collaboration with AI. Leadership takeaway: AI should amplify human judgment, not replace it. What You’ll Learn: • Why most companies are early in AI adoption • Difference between using AI and redesigning workflows • Why regulated industries are uniquely complex • How AI transforms financial services operations • Why governance and auditability matter • How AI compresses work from weeks to hours • Why workflow design matters more than tools • How AI agents reshape execution • Why knowledge systems matter • Why adoption must be staged • Why trust is becoming a core product • How workforce skills are shifting • Why AI democratizes cognitive capability • Why iteration matters in leadership • Future of AI-driven enterprise systems Resources: Hartford AI Partners https://hartfordaipartners.com Claude https://claude.ai OpenAI https://openai.com Obsidian https://obsidian.md WhisperFlow https://whisperflow.ai GetVictor https://www.getvictor.ai Watch & Follow AI with Bry: Full episodes https://bry.net/ai YouTube https://www.youtube.com/@aiwithbry Instagram https://www.instagram.com/aiwithbry Facebook https://www.facebook.com/profile.php?id=61575757332333 TikTok https://www.tiktok.com/@aiwithbry

    39 min
  3. Why Software is No Longer Written It's Produced Like a Factory

    Apr 15

    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 of how software is produced, scaled, and optimized. The shift is no longer just faster coding, but the move from handcrafted development to AI-driven software factories where systems and applications are generated and deployed at scale. This episode reframes enterprise software as a manufacturing system where ideas move through AI-powered pipelines and token economics reshape engineering value. Guest: Chris Strobl Chris Strobl is Founder and CEO of GitFlash, an AI deployment and adoption company helping enterprises become AI-native software factories. With a background in mathematics and economics from LSE and startup experience, he brings a systems approach to AI transformation. He is known for the software factory model: software is no longer manually written line by line but produced through AI pipelines that unify planning, design, development, and deployment. We explore how software development is shifting from traditional engineering to AI-native production systems. Chris describes this as an evolution of the industrial assembly line where ideas move through structured AI stages to produce software faster and at lower cost. A key shift is the breakdown of Agile and Scrum. These frameworks were designed for human coding, but AI systems shift the bottleneck from coding speed to system design and orchestration. AI is also changing cost structures. Work that once required large engineering teams can now be reduced by 90–99% in optimized workflows, changing staffing and ROI models. Chris introduces token economics, where AI usage becomes a measurable input like raw materials in manufacturing. Future engineering performance will be measured by how effectively tokens convert into business value. Incentives matter. Aligning compensation with AI usage—not just output—drives better adoption and efficiency. Many enterprises remain stuck in pilot mode. Real transformation requires moving from experimentation to full system redesign focused on growth, not just efficiency. Leadership now requires asking scale-level questions instead of incremental improvement questions. AI enables continuous production systems where software is generated, optimized, and evolved like a living factory. What You’ll Learn: • What a software factory is and why it replaces traditional dev • How AI turns software into production systems • Why Agile and Scrum are breaking down • How token economics changes engineering cost • Why software is shifting from labor to output systems • How AI reduces delivery cost by up to 90–99% • Why incentives drive enterprise AI adoption • How companies move beyond pilots • Why leadership must focus on scale • How AI enables end-to-end software pipelines • Why developers become system architects • How AI reshapes software economics • Why this shift is technical + cultural Resources: GitFlash https://gitflash.com | Software Factory Guy https://softwarefactoryguy.com Watch & Follow AI with Bry: Full episodes https://bry.net/ai | YouTube https://www.youtube.com/@aiwithbry | Instagram https://www.instagram.com/aiwithbry | Facebook https://www.facebook.com/profile.php?id=61575757332333 | TikTok https://www.tiktok.com/@aiwithbry The future of software is not how fast humans code, but how well organizations design AI production systems that turn ideas into scalable products. Learn, leverage, and lead.

    42 min
  4. How a Nurse Practitioner is Rebuilding Geriatric Care with AI from the Ground Up

    Apr 8

    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 care is delivered, how clinicians interact with patients, and how systems shift from reactive to proactive models. The challenge is not adoption—it is designing systems that reduce friction, improve outcomes, and keep patients and clinicians at the center. This episode reframes AI through geriatric care, caregiver strain, administrative burden, and the opportunity to close gaps in continuity and access. Guest: Joe Harrison Joseph Harrison is a nurse practitioner, clinician entrepreneur, and Founder & CEO of Avail Healthcare, a clinician-built medical group delivering proactive in-home and virtual care for seniors and underserved adults. He has experience in mobile care, Medicare Advantage, and geriatric mental health, leading teams supporting patients with dementia, depression, anxiety, and chronic conditions. He also serves as volunteer clinical faculty at UCSF. At Avail Healthcare, he builds care models focused on aging in place and caregiver support, grounded in the quintuple aim: patient experience, provider experience, outcomes, equity, and sustainability. We explore how AI is reshaping real-world healthcare delivery. Joe explains that geriatric systems are structurally reactive, requiring patients to come to care instead of care coming to them. This drives higher cost, fragmentation, and missed early intervention. AI enables a shift toward proactive care through remote monitoring, AI-assisted triage, and continuous communication, improving early detection and reducing emergency utilization. A major theme is administrative burden. AI scribes now document visits in real time, reducing charting, improving accuracy, and giving clinicians more time with patients. Joe notes that 15–20% of healthcare costs are administrative, creating major system-wide friction. AI reduces this load for both clinicians and patients. We also explore the caregiver crisis, with 1 in 4 adults acting as caregivers. AI helps generate care plans, coordinate resources, and reduce coordination burden. Another key insight is the rise of clinician entrepreneurs. AI tools now allow non-technical clinicians to design workflows, analyze data, and build systems using natural language interfaces. Joe emphasizes that governance, infrastructure, and privacy must scale alongside innovation to protect patients and providers. Core theme: AI should not only improve efficiency—it should improve human care. What You’ll Learn: • Why healthcare is reactive and how AI enables proactive care • How AI transforms geriatric and behavioral health delivery • Role of AI scribes in reducing burnout • Why 15–20% of healthcare costs are administrative • How AI improves documentation and billing accuracy • The caregiver crisis and AI support systems • How remote monitoring reduces ER visits • Why clinician experience affects outcomes • AI agents as virtual team members • Rise of clinician entrepreneurs using AI tools • Non-technical building via AI interfaces • Importance of governance and privacy • Alignment with the quintuple aim Resources: Avail Healthcare https://www.availhealthcare.co Watch & Follow AI with Bry: Full episodes https://bry.net/ai | YouTube https://www.youtube.com/@aiwithbry | Instagram https://www.instagram.com/aiwithbry | Facebook https://www.facebook.com/profile.php?id=61575757332333 | TikTok https://www.tiktok.com/@aiwithbry The future of healthcare AI will not be defined by automation alone, but by whether systems reduce friction, support clinicians, and bring care closer to those who need it most. Learn, leverage, and lead.

    33 min
  5. Why AI is Making Healthcare Faster But Not Better for Patients

    Apr 1

    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, resilience, and human experience. The real challenge is alignment between innovation, trust, and human need—not capability alone. This conversation reframes AI through decades of infrastructure leadership, personal medical recovery, and keeping humans at the center of advancement. Guest: David Jones David Jones is a veteran technology executive with 40+ years across telecommunications, regulatory systems, networking infrastructure, and large-scale data centers. He has built companies from startup stage to billion-dollar platforms through multiple private equity cycles and acquisitions. After surviving a life-threatening infection resulting in the loss of his right hand and part of his forearm, he shifted into medtech innovation, prosthetics, and patient-centered systems. He now supports early-stage founders through the Pearl Innovation Center in Charlotte, focused on healthcare, AI, and human recovery. His perspective connects enterprise infrastructure with lived patient experience in complex healthcare systems. We explore decades of technology evolution and connect it to healthcare transformation and prosthetic innovation. David emphasizes that leadership requires adaptability, trust, and aligning strategy with system design before scaling execution. A key theme is that AI is accelerating all layers of technology but not always improving outcomes. In healthcare, AI improves documentation, billing, and workflows but often shifts rather than reduces workload, increasing administrative burden. Without intentional design, AI can optimize metrics instead of patient experience. The conversation moves into prosthetics and medtech innovation. After losing his hand, David became deeply involved in prosthetic systems, sensor integration, and AI-enabled biomechanics. Modern prosthetics are increasingly AI-driven systems using sensors, machine learning, and feedback loops to translate muscle signals into movement. However, innovation is limited by cost, market size, and awareness of what is currently possible. Upper-limb prosthetics remain significantly underserved despite advances in robotics and wearables. Through the Pearl Innovation Center, David supports ecosystem development for medtech founders navigating high complexity. Core leadership insight: technology must serve human continuity, not replace it. Trust is built through listening, not automation. AI accelerates systems, but it cannot replace empathy, context, or human attention. What You’ll Learn: • AI accelerates infrastructure but doesn’t guarantee better outcomes • Leadership requires aligning strategy with system design • Data centers function as utility ecosystems • AI increases productivity but can increase clinical workload • System design determines patient outcomes • Prosthetics are becoming AI-driven biomechanical systems • Upper-limb prosthetics remain underdeveloped • Sensor fusion + ML reshape human-device interaction • Market size influences medtech innovation • Ecosystem support is critical for founders • Trust remains foundational Resources (full links available on show page): Pearl Innovation Center (Charlotte MedTech Ecosystem) Wexford Connect Labs Watch & Follow AI with Bry (all platforms available here): Full episodes: https://bry.net/ai The future of AI in healthcare and infrastructure will not be defined by speed alone, but by how well we keep humans at the center of increasingly intelligent systems. Learn, leverage, and lead.

    36 min
  6. How a Resident Physician Building AI to Fix Broken Healthcare Contracts

    Mar 25

    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. This conversation reframes AI in healthcare not as external disruption, but as innovation from within—when clinicians closest to the pain points become the builders. Guest: Daniela Dennis Daniela Dennis is an emergency medicine resident and Founder of Payscope MD, an AI platform that helps physicians understand and optimize employment contracts. She also hosts the Resident Founder podcast and is author of What Med School Didn’t Teach Me About Money. As a first-generation college graduate, she works at the intersection of medicine, entrepreneurship, and AI, focused on reducing information asymmetry and empowering physicians with tools they were never given in training. She is not theorizing about problems—she is building while living them. We explore a major shift in healthcare: builders emerging from inside the system. Daniela explains how Payscope MD originated from firsthand frustration with physician contracts—complex language, high legal costs, and lack of transparency at critical career moments. AI became the bridge to simplify and unlock understanding. A key insight: AI is only as strong as the data it learns from. In healthcare, much of that data is fragmented or locked in systems and contracts, creating opportunity for domain experts to build better tools through real-world exposure. We also discuss how AI is already transforming clinical workflows—documentation, dictation, radiology, and patient monitoring. While efficiency gains matter, the biggest impact is time: giving clinicians back attention for patients. Daniela emphasizes that AI is not replacing physicians—it is augmenting them. But it introduces new challenges as patients increasingly rely on AI-generated medical information, increasing the need for clinician interpretation and guidance. On the builder side, the barrier to entry has dropped significantly. With modern AI tools, clinicians without technical backgrounds can now prototype, validate, and launch products. This is enabling a new wave of physician entrepreneurs. We also explore how physicians must shift from passive adoption to active participation—building tools, shaping workflows, and educating patients. Leadership in healthcare is expanding beyond clinical care into creation and communication. AI in healthcare will not be defined only by institutions or external startups. It will be shaped by clinicians who choose to engage, build, and lead. What You’ll Learn: • AI lowers the barrier to building, not the need for insight • Clinicians are becoming builders within the system • Healthcare data gaps create opportunity for domain experts • AI improves workflows and returns time to patients • Patients are influenced by AI-generated medical information • Human oversight remains critical in medical decisions • Entrepreneurship is now more accessible to physicians • AI tools enable rapid prototyping (“vibe coding”) • Trust and credibility are evolving in healthcare • Leadership now includes building and educating with AI Resources: Payscope MD: https://www.getpacescope.com Resident Founder Podcast LinkedIn: https://www.linkedin.com Instagram: https://www.instagram.com Watch & Follow AI with Bry: Full episodes: https://bry.net/ai YouTube: https://www.youtube.com/@aiwithbry Instagram: https://www.instagram.com/aiwithbry Facebook: https://www.facebook.com/profile.php?id=61575757332333 TikTok: https://www.tiktok.com/@aiwithbry The future belongs to those who build from lived experience. Learn, leverage, and lead.

    31 min
  7. How AI is Empowering Nurse Practitioners to Rebuild Healthcare

    Mar 18

    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 needed to deliver better care. This conversation reframes AI as a grassroots transformation driven by practitioners building sustainable, patient-centered businesses. Guest: Lynn Rapsilber Lynn Rapsilber is Co-Founder and CEO of the National Nurse Practitioner Entrepreneur Network (NNPEN), a community that provides nurse practitioners with business education, advocacy, and resources often missing from clinical training. With extensive experience in patient care and healthcare leadership, Lynn helps NPs build, scale, and sustain independent practices. Her work bridges entrepreneurship, policy, and care delivery, helping clinicians step into ownership and reshape healthcare from within. We discuss a major challenge in healthcare today: the people closest to patients are often the least equipped with modern business tools. Lynn explains how nurse practitioners are becoming entrepreneurs without formal business training and how organizations like NNPEN help close that gap. AI is now accelerating that evolution. One of the biggest barriers to adoption is fear. Clinicians worry about complexity, cost, and losing the human connection with patients. Lynn reframes AI as a support system, not a replacement. We explore how AI is already improving healthcare through virtual assistants, front-desk automation, clinical decision support, documentation, billing workflows, and AI-powered medical scribes. These tools reduce administrative burdens and allow providers to focus more on patient care. Lynn also shares how AI supports personalized care through real-time protocols, remote monitoring, and data-driven insights that enable earlier intervention and better chronic disease management. On the business side, AI helps solo practitioners operate with the capabilities of larger organizations through automation, reporting, and operational efficiencies that support sustainable growth. We also discuss trust, privacy, data ownership, education, and leadership. Lynn highlights how NNPEN is creating a collaborative ecosystem where practitioners share resources, gain visibility, and increase collective influence. AI is not replacing healthcare providers. It is giving them the leverage to reclaim their role. What You'll Learn: • AI adoption starts with education and trust • NPs are building businesses without formal business training • AI reduces administrative burden and restores patient focus • Medical scribes provide rapid ROI • Personalized care improves through data and insights • Solo practices can scale with AI-powered systems • Cost barriers are decreasing • Data ownership and privacy matter • Ecosystem thinking creates leverage • Healthcare transformation will happen from the ground up Resources: NNPEN: https://www.nnpen.org NP Practice Directory: https://www.npdirectory.org Watch & Follow AI with Bry: https://bry.net/ai YouTube: https://www.youtube.com/@aiwithbry Instagram: https://www.instagram.com/aiwithbry Facebook: https://www.facebook.com/profile.php?id=61575757332333 TikTok: https://www.tiktok.com/@aiwithbry The future of healthcare will not be built solely in hospitals or boardrooms. It will be shaped by empowered practitioners using technology to deliver better, more human care. Learn, leverage, and lead.

    30 min
  8. Busy Sales Teams vs Real Revenue Engines

    Mar 11

    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, embedding repeatable systems, and ensuring that human judgment drives meaningful outcomes as machines multiply capacity. This conversation reframes AI adoption as a people and execution challenge, not just a technical one. Guest Introduction Rich Makover Full Name: Rich Makover Rich is a Fractional Chief Revenue Officer and Managing Partner at Tech CXO. He works with companies across consumer goods, beauty, jewelry, and technology to build scalable revenue engines. With decades of experience at KPMG, Avon, and Citizens Watch Group, Rich now embeds investor-grade repeatable execution into growth-stage and PE-backed companies. He is also a certified executive coach and former D1 Penn State lacrosse captain, translating high-performing team principles from the locker room to the boardroom. His perspective matters because he operates at the intersection of strategy, people, and process. Rich helps organizations turn founder intuition into disciplined, repeatable revenue execution while leveraging AI to multiply team effectiveness. Core Conversation Summary We unpacked a central tension facing revenue organizations today: speed versus adoption. Rich emphasized that AI is not about replacing relationships—it’s about enabling teams to perform at scale with clarity, preparation, and confidence. When adoption is structured into workflows, AI improves meeting prep, lead qualification, proposal creation, and handoffs to customer success. Without intentional integration, tools fail to stick. One of the biggest challenges in AI adoption is critical mass. Early adoption by a few key team members drives momentum, while isolated usage leads to stalled implementations. Leadership through example—walking the walk—drives adoption and builds trust. We explored repeatable systems versus accidental success. Embedding AI into defined processes increases usage, accountability, and measurable results. Rich shared real-world examples where AI increased meetings, streamlined proposals, and freed leaders to focus on coaching talent rather than manual tasks. On leadership, Rich highlighted that AI accelerates execution but does not replace judgment. Experienced leaders use AI to amplify their perspective, speed planning, and enhance team performance. Younger team members may over-rely on AI, so balancing automation with critical thinking is essential. Ultimately, AI adoption on the revenue side is about process, culture, and leadership, not just shiny tools. The leaders who succeed are those who structure systems that allow teams to perform repeatedly under pressure. What You Will Learn in This Episode AI Adoption Is A People And Execution ChallengeCritical Mass, Not Perfection, Drives AdoptionRepeatable Systems Outperform Accidental SuccessAI Enhances Preparation, Proposal, And Hand-Off ProcessesLeadership By Example Accelerates Tool IntegrationExperienced Judgment Multiplies AI’s ValueBalancing AI Usage With Critical Thinking Avoids RiskStructured Workflows Increase Stickiness And ROIAI Reveals and Reinforces Team Culture, It Doesn’t Replace ItCollaboration And Coaching Drive Sustainable Revenue GrowthResources, Tools and Platforms Mentioned Tech CXO https://www.techcxo.com LinkedIn https://www.linkedin.com/in/rich-makover Fractional Edge Newsletter Link in show notes Watch and Follow AI with Bry Full episodes and show notes https://bry.net/ai YouTube https://www.youtube.com/@aiwithbry Instagram https://www.instagram.com/aiwithbry Facebook https://www.facebook.com/profile.php?id=61575757332333 TikTok https://www.tiktok.com/@aiwithbry The future belongs to leaders who structure systems, multiply their team’s capacity, and embed execution into culture.

    34 min
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5
out of 5
2 Ratings

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 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.

Information

  • Creator
    Bryan Dennstedt
  • Years Active
    2025 - 2026
  • Episodes
    35
  • Rating
    Clean
  • Copyright
    © AI with Bry
  • Show Website
    AI with Bry Podcast