Episodes

  • The Marketplace That Time Forgot

    The Marketplace That Time Forgot
    Nov 13 2025
    SummaryWhat happens when two veteran systems thinkers take a forgotten marketplace, shake out the dust, and sketch a future that actually makes sense? Keith and Cameron dive into sneaker drama, live shopping chaos, community taste makers, and the strange emotional logic of teenage buyers. Then they roll up their sleeves and redesign eBay from the inside out. Their pitch is simple. Stop trying to own the shopping cart. Turn the platform into an open source style ecosystem that lets creators, agents, and every platform on earth push buyers straight into a purchase. Let the buy button travel across TikTok, YouTube, and whatever comes next. It becomes a world where eBay’s value is not in its old interface but in the data, the trust, and the pipes that move product. The result is funny, candid, and surprisingly practical.Chapters00:00 Tech glitches, trains, and the cosmic comedy of starting the day03:30 Astrology, economics, and the weird weather of collective systems05:40 Car trouble and the universal language of broken service10:15 Modern frustration and why nothing works like it should19:00 Early eBay and the brilliance of not owning inventory21:54 Auctions, trust, and the first era of online courage23:37 How simple UX once carried entire marketplaces28:10 Why legacy systems strangle modern retail30:55 The teenage sneaker story heard around the world35:17 Why kids think eBay feels cursed and risky38:40 How fear reshapes buyer behavior41:01 Live shopping confusion and digital carnival vibes44:30 Creator power and the real source of consumer influence47:55 Why brands should stop trying to control everything50:05 Customer service disasters and lost trust59:04 What shoppers actually experience during broken interactions01:00:30 The calm logic of letting platforms do the back end01:10:40 Open ecosystems, APIs, and the freedom of a roaming buy button01:18:25 Value delivery now and the painful cost of compute01:20:00 The future blueprint for a marketplace that could rise again01:22:10 Why companies fear risk and cling to outdated methods01:24:40 How first mover advantage distorts platform strategy01:27:55 Why brands overspend rebuilding what others already perfected01:30:03 Cameron’s take on bold thinking inside his current company01:31:02 How risk and opportunity analysis can accelerate innovation01:31:52 Keith’s final point on leadership courage and imagination01:32:36 Why companies hesitate to embrace exponential potential01:32:53 The role of financial clarity in strategy decisions01:33:09 How revenue targets shape decisions in legacy companiesTakeawaysInterfaces are distractions. The true value of a marketplace lives in its pipes, identifiers, and trust primitives, not in the visible surface.Owning the shopping cart is a sunk-cost illusion. Control of the transaction interface gives far less leverage than control of the underlying fulfillment and verification layer.Legacy systems fail not from age but from entrenchment. Every added feature reinforces the original architecture, which then blocks innovation through path dependence.User trust is not emotional. It is infrastructural. Reputation systems, verification steps, and dispute automation create trust far more effectively than branding or marketing.Creator led commerce outperforms platform led commerce because the distribution nodes already exist. Platforms should supply rails, not audiences.APIs are the new storefronts. As agents and LLMs mediate buying behavior, the winning marketplace will be the one most easily integrated, not the one most beautifully designed.Value compounds only when delivery is immediate. Fast proof of value creates organizational momentum, lowers political resistance, and protects teams from budget collapse.Compute cost is a strategic governor. Every experimental feature built on AI spend must justify itself quickly or it quietly sinks the company through operational drag.Modern retail collapses under its own identity crisis. Companies try to act like tech firms while still thinking like merchandisers, leading to conflicting incentives and slow decision loops.Fear based leadership hides inside “process.” The more rigid the workflow, the more it signals that executives are trying to avoid downside rather than create upside.Influencer ecosystems outperform centralized platforms because they distribute risk, diversify taste making, and reduce the burden of owning cultural relevance.Marketplaces do not fail from competition. They fail from internal friction. When the cost of coordinating teams exceeds the cost of serving customers, innovation halts and the platform becomes a relic.
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    1 hr and 34 mins
  • Rebooting The Machine: When Systems Get Weird

    Rebooting The Machine: When Systems Get Weird
    Nov 7 2025
    SummaryA recording glitch sparks a deeper question: what does it really mean to reboot a system? In this episode, The Monolith traces the parallels between technical restarts and human resets—when teams, tools, or minds fall out of sync. Keith and Cameron move from design thinking into systems awareness, exploring circular AI economies, nuclear-powered data centers, and the strange calm of Mercury retrograde as a metaphor for reflection. They discuss how neurodiverse perception fuels pattern recognition, why giving away IP can expand leverage, and how energy—not data—is becoming the real bottleneck of intelligence. Across stories from parenting to Macy’s innovation labs, they reveal why emergence, feedback, and timing matter more than control. The result is a conversation about resilience in an exponential age—and why the next frontier of strategy begins when systems get weird.Keith and Cameron kick off with a real-world audio snafu (Riverside glitch) and use it to riff on the “turn it off and on again” instinct—asking what a reboot would look like for a company. That leads into boundaries with tech (Cameron’s 13-year-old going phoneless for a few days), detox effects, and encoding household “rules as system” into devices.They then widen to AI in the enterprise: shifting work onto higher-paid teams, the risk of automating infra-ops, circular compute financing (credits vs. cash), Microsoft/OpenAI capital structure talk, and whether current AI investment loops echo Enron-style accounting games. Walmart’s public stance on preparing its workforce comes up, as does nuclear power for data centers (Hyundai micro-reactors), and the sci-fi anxiety of hardened, redundant server farms (Skynet vibes).From there, the episode pivots into the show’s new scope: systems thinking as the spine, with astrology used not as fortune-telling but as a timing/clock metaphor for cycles (e.g., Mercury retrogrades as “redo/reflect” periods). They explicitly invite listeners to submit anonymous corporate problems to be “red-teamed” on-air. The back half dives into the psychology of systems thinkers (often neurodivergent), “emergence,” and concrete war stories (Macy’s: giving IP away to move up-system, making analytics/innovation frameworks accessible). They close with “exponential age” framing—moving from atoms→bits and increasingly back to atoms (3D printers), plus a quick off-grid kit anecdote (Jamaica: sat phone + solar), and why systems literacy will be the differentiator going forward.Chapters00:00:00 – Cold open: Riverside glitch → “turn it off and on again” as metaphor.00:05:00 – Going analog: parenting without devices and digital detox as systems reset.00:10:00 – Workload misalignment and AI as a can-kicking exercise.00:15:00 – Circular compute loops; cloud credits vs. real capital.00:20:00 – Energy and AI infrastructure; Hyundai micro-reactors and Skynet anxieties.00:25:00 – Listener “red team” invite and the shift to cycles and systems.00:30:00 – Systems thinking as the spine of design; retrograde weirdness as signal.00:35:00 – Neurodiversity and systems cognition; feeling “crazy” in linear orgs.00:40:00 – Emergence explained; audience fit for complexity.00:45:00 – Making systems tools accessible; guardrails for AI and nuclear scale.00:50:00 – The exponential age; time compression from 2020 to 2030.00:55:00 – Reverse-engineering black boxes; car trouble as systems metaphor.01:00:00 – Digestibility and scaffolding; astrology’s stigma revisited.01:05:00 – Corporate systems, Kung-fu uploads, and Macy’s case setup.01:10:00 – Triple-win design; giving away IP to move up-system.01:15:00 – Commoditizing analytics; democratizing truth across functions.01:20:00 – Value exchange after the giveaway; staying draftable.01:25:00 – Updating mental models and expanding surface area.01:30:00 – Why “design” alone is too small; interfaces as commodities.01:35:00 – Untethering from screens; the web still in beta.01:40:00 – Clay Shirky and electricity analogy; tech gets boring → real change.01:45:00 – 3D printing, off-grid kits (Jamaica), and resilient infrastructure.01:50:00 – Control systems, feedback loops, and final reflections on systems literacy.TakeawaysThe episode’s cold open (a Riverside recording failure) becomes an unintended metaphor for systemic breakdown and the instinct to “turn it off and back on again.”A “reboot” can be both technical and psychological — sometimes systems (or people) need a reset to clear feedback loops.Short-term tech outages reveal hidden dependencies in our workflows, exposing how deeply we’re entangled with infrastructure.Going phoneless or offline (as in Cameron’s family experiment) acts as a mini-systems intervention, resetting the nervous system and revealing addiction loops.Design thinking has evolved into systems thinking — from crafting interfaces to shaping context...
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    1 hr and 51 mins
  • Something's Up

    Something's Up
    Nov 7 2025

    Summary
    In this conversation, Cameron and Keith explore the changing dynamics of neighborhoods, societal shifts, and the impact of technology and AI on human relationships. They discuss the importance of systems thinking and the influence of astrological cycles on personal and societal change. The dialogue emphasizes the need for reconnection in a disconnected world and the redefinition of value in the workplace. They also touch on the role of fear in decision-making and the hope for a better future amidst uncertainty. In this conversation, Keith and Cameron explore the themes of societal resilience in the face of strife, the importance of innovative education, and the need for systems thinking in addressing complex challenges. They discuss how technology and change are reshaping our world, emphasizing the necessity for adaptability and a proactive mindset. The dialogue also touches on environmental awareness and community action, illustrating how education can empower students to effect real change. Ultimately, they highlight the entrepreneurial mindset as essential for navigating the evolving landscape of business and society.


    Takeaways

    • Fewer horns and gunshots indicate changing neighborhood dynamics.
    • Social norms are breaking down, leading to increased petty crime.
    • The macro and micro perspectives help understand societal changes.
    • Astrological cycles influence societal shifts and personal experiences.
    • AI and technology are reshaping communication and society.
    • Navigating personal change is essential in a rapidly evolving world.
    • Systems thinking is crucial for understanding complex interactions.
    • Recognizing cycles and patterns can help in decision-making.
    • Reconnecting with others is vital in a disconnected world.
    • The future of work requires redefining relationships and value. Societal strife can lead to resilience and growth.
    • Change often requires a shift in mindset and approach.
    • Education should focus on innovative and conceptual learning.
    • Environmental awareness is crucial for community action.
    • Systems thinking is essential for effective change agents.
    • An entrepreneurial mindset is necessary in today's business landscape.
    • Technology is rapidly changing the pace of life and work.
    • Building resiliency is key to navigating uncertainty.
    • Delivering value quickly is vital for success.
    • Collaboration and community engagement can drive meaningful change.

    Titles
    Changing Neighborhood Dynamics
    Societal Shifts and Systemic Changes


    Sound bites
    "The system demands stasis."
    "Don't give up."
    "This is not right."


    Chapters
    00:00 Changing Neighborhood Dynamics
    02:45 Societal Shifts and Systemic Changes
    05:51 Macro and Micro Perspectives
    08:45 Cycles of Change and Innovation
    11:39 Astrological Influences on Society
    14:41 Understanding Patterns in Human Behavior
    17:24 The Impact of Technology on Humanity
    20:28 Navigating the Future of Work
    23:29 Reconnecting in a Post-COVID World
    36:49 The Impact of Low Interest Rates on Business Dynamics
    39:08 Media Influence and Public Perception
    41:07 Doublespeak and Political Discourse
    44:02 The Role of Systems Thinkers in Change
    47:55 Moral Compass in Business Practices
    50:52 The Future of Education and Learning
    54:48 Navigating Change in a Rapidly Evolving World
    01:14:48 Innovative Education and Systems Thinking
    01:22:17 The Role of Science in Understanding Systems
    01:27:35 Navigating Corporate Structures and Value Delivery
    01:36:56 The Entrepreneurial Mindset in Modern Business


    Keywords
    neighborhood dynamics, societal shifts, systems thinking, astrological influences, AI impact, personal change, macro micro perspectives, future of work, leadership, redefining value, societal strife, resilience, uncertainty, change, education, environmental awareness, systems thinking, change agents, entrepreneurial mindset, technology
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    1 hr and 48 mins
  • We're Vibe Designing

    We're Vibe Designing
    Sep 15 2025

    Summary

    In this conversation, Keith and Cameron discuss the evolution of design and development processes, emphasizing the integration of AI and systems thinking. They explore innovative approaches to design, the importance of real-time collaboration, and the need for effective communication in navigating complex projects. The discussion highlights the shift towards AI-driven tools that enhance efficiency and creativity, while also addressing the challenges and opportunities presented by these advancements. In this conversation, Cameron and Keith explore the multifaceted impacts of AI on employment, the current political climate, and the dynamics of social media. They discuss the importance of curiosity and adaptability in navigating change, the synthetic nature of modern life, and the need for innovative solutions in business. The dialogue emphasizes the significance of engaging with audiences and learning from past innovations while rethinking business models for the future.

    Chapters

    00:00 Introduction and Personal Updates

    01:28 Innovative Design Approaches

    04:50 AI-Driven Development Tools

    08:45 Rapid Prototyping and Real-Time Feedback

    12:50 Systems Thinking in Design

    18:05 Defining the Problem Space

    24:45 The Future of Design and Development

    28:12 Navigating Complex Systems

    32:12 The Importance of Human Connection

    36:29 Embracing Systems Thinking

    41:39 The Role of Collaboration in Innovation

    46:10 Understanding the Current Landscape

    51:09 Leveraging Technology for Personal Growth

    58:02 Navigating Corporate Politics in Innovation

    01:00:23 The Power of Experimentation and Customer Engagement

    01:02:19 Harnessing Demand: The Unexpected Success

    01:04:11 Leadership and Systems Thinking in Business

    01:05:58 Rethinking Risk and Long-Term Strategy

    01:07:47 The Role of Innovation in Modern Business

    01:09:09 Challenges in Technology Implementation

    01:12:10 The Complexity of Modern Systems

    01:13:35 The Importance of Storytelling in Business

    01:18:04 Embracing Change and Future Opportunities

    Takeaways

    • The integration of AI in design processes is revolutionizing the industry.
    • Real-time collaboration enhances customer engagement and feedback.
    • Systems thinking is crucial for effective problem-solving in design.
    • Defining the problem space is essential before diving into solutions.
    • AI tools can significantly reduce development time and effort.
    • Effective communication is key to successful project outcomes.
    • Designers are becoming more autonomous in their roles.
    • The future of design will increasingly rely on AI and innovative tools.
    • Understanding the entire system is vital to avoid deviations in development.
    • Experimentation and curiosity are essential for adapting to new technologies. AI is reshaping the job market, leading to potential layoffs.
    • Political and social media dynamics are influencing public perception.
    • Curiosity and adaptability are essential in times of change.
    • The synthetic nature of modern life can be leveraged for personal growth.
    • Learning to use new tools is crucial for survival in a changing landscape.
    • Innovative solutions can drive business success and customer engagement.
    • Engaging with audiences can provide valuable insights and feedback.
    • Past innovations offer lessons for future endeavors.
    • Rethinking business models is necessary for long-term success.
    • Staying curious is key to navigating the complexities of modern life.

    Keywords

    AI, design thinking, systems thinking, real-time collaboration, innovative tools, development, communication, problem-solving, technology, user experience, AI, employment, political climate, social media, curiosity, technology, innovation, business models, adaptability, audience engagement
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    1 hr and 22 mins
  • Systems Thinking

    Systems Thinking
    Aug 3 2025

    Summary

    In this conversation, Cameron and Keith explore the impact of AI on various industries, emphasizing the importance of systems thinking in adapting to change. They discuss the significance of understanding stocks, flows, and feedback loops in decision-making, and how designers must evolve with technology. The conversation highlights the need for human-centric systems and the role of mental models in shaping our understanding of complex systems. They also touch on the challenges of linear thinking and the necessity of innovation in a rapidly changing landscape.



    Chapters

    00:00 Introduction and Technical Setup

    03:02 Adapting to Change in Design and Business

    05:56 Understanding Systems Thinking

    09:02 The Role of Technology in Design

    11:54 Feedback Loops and Interconnected Systems

    15:00 The Evolution of Design Practices

    18:02 The Future of Human-Computer Interaction

    23:19 The Changing Landscape of Design and Business

    26:20 Systems Thinking: A New Approach to Problem Solving

    29:42 Mental Models and Their Impact on Decision Making

    30:49 Understanding Linear vs Nonlinear Relationships

    32:32 Innovation and the Role of Technology in Business

    35:50 The Human Element in Technological Change

    39:18 Navigating Complexity in Organizational Systems

    42:50 The Importance of Perspective in Leadership

    46:16 The Role of Detail in Systems Thinking

    49:09 AI and the Future of Human Potential

    54:26 The Human Element in Innovation

    57:09 Universal Basic Income and Economic Fragility

    01:00:28 Systems Thinking and Human-Centric Design

    01:06:10 The Ascent of Man and Systems Thinking

    01:15:05 Redefining Humanity in the Age of AI



    Takeaways


    AI is disrupting all industries, not just design.

    Systems thinking is crucial for adapting to change.

    Understanding stocks and flows helps in decision-making.

    Feedback loops are essential in assessing systems.

    Designers need to evolve with technology.

    Mental models shape our understanding of systems.

    Linear thinking limits our ability to adapt.

    The future of work requires a human-centric approach.

    Innovation is key to surviving in a changing landscape.

    Embracing change is necessary for growth.
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    1 hr and 22 mins
  • There Is No Interface

    There Is No Interface
    Jul 14 2025

    Summary

    In this conversation, Cameron and Keith discuss the challenges and opportunities in the intersection of technology, design, and user experience. They explore the impact of AI on design practices, the importance of resilience in adapting to change, and the evolving nature of retail and consumer behavior. The dialogue emphasizes the need for designers to focus on problem-solving and innovation rather than just traditional interfaces, highlighting the significance of understanding context in design. As they navigate through technical difficulties, they reflect on the future of commerce and the human experience in a rapidly changing world.



    Chapters

    00:00 Technical Difficulties and New Beginnings

    05:32 Challenges in Legal Tech and AI Integration

    11:20 The Evolution of Design Thinking

    16:59 The Future of Interfaces and User Experience

    21:11 Navigating Technology Challenges

    22:18 The Future of Work and Tech Monopolies

    24:16 Designers and the Hacker Mindset

    26:35 The Role of Designers in Problem Solving

    28:46 Understanding Complex Systems

    31:18 The Importance of Context in Design

    33:58 Human Interaction and System Design

    36:18 Redefining the Role of Designers

    39:14 The Future of Interfaces and User Experience

    44:00 The Human Element in Technology

    46:58 Personal Accessibility in Information Consumption

    49:43 Leveraging Technology for Enhanced Learning

    50:58 Innovative Shopping Experiences with AI

    53:49 The Future of Retail and AI Integration

    56:59 The Evolution of Design Mindsets

    01:01:22 Navigating Change in a Rapidly Evolving World

    01:06:55 Understanding Cycles and Patterns in Society

    01:11:53 The Importance of Adaptability and Resilience



    Takeaways

    • Technical difficulties can lead to new setups and improvements.
    • Legal tech faces challenges in automation and systematization.
    • Designers need to focus on problem-solving rather than just interfaces.
    • The future of design may involve less emphasis on traditional interfaces.
    • AI is transforming the way we approach design and user experience.
    • Personal resilience is crucial in adapting to rapid changes.
    • Designers should embrace innovation and not cling to ownership of products.
    • Understanding the context of design is essential for success.
    • The intersection of technology and human experience is evolving.
    • Retail behavior is changing with the advent of AI and new technologies.


    Keywords

    technology, design, AI, innovation, user experience, legal tech, resilience, retail, commerce, human experience
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    1 hr and 21 mins
  • Own The Innovation, Not The Product

    Own The Innovation, Not The Product
    Jul 14 2025

    Summary


    In this conversation, Cameron and Keith explore the intersection of design, automation, and AI, discussing how these elements are reshaping the landscape of work and creativity. They emphasize the importance of innovation over product ownership, the necessity of understanding organizational structures, and the role of systems thinking in navigating these changes. The discussion also highlights the potential of AI as a tool for enhancing creativity and problem-solving, while cautioning against complacency in a rapidly evolving environment.

    Chapters


    00:00 The Monolith Connection

    02:57 Navigating Chaos: Immigration and Technology

    05:50 Automating Design: A New Era

    08:49 The Future of Design in a Tech-Driven World

    11:44 Mindset Shifts: Embracing Change

    14:42 Creativity and Innovation in Design

    17:41 The Role of Designers in a Tech Landscape

    22:55 The Importance of Systems Thinking in Design

    29:42 Navigating Organizational Culture and Innovation

    38:35 The Role of Documentation and Prototyping in Design

    46:03 Embracing Change and Future Opportunities in Design

    53:44 Embracing AI in Design

    56:53 The Rapid Evolution of Technology

    59:13 OpenAI's Strategic Move

    01:01:15 The Power of AI in Problem Solving

    01:05:20 Riding the Wave of Innovation

    01:09:12 Owning Innovation, Not Products

    01:10:38 The Role of Storytelling in Design

    01:12:05 Systems Thinking and Future Directions

    Takeaways

    • Innovation is key; focus on owning the innovation, not the product.
    • Understanding organizational culture is crucial for effective design.
    • Systems thinking is essential for navigating complex environments.
    • AI can enhance creativity and streamline design processes.
    • Designers must adapt to the changing landscape of work.
    • Storytelling is a powerful tool for designers to communicate ideas.
    • Embracing change is necessary for growth and success.
    • The future of design lies in understanding human-computer interaction.
    • Prompt quality is vital for effective use of AI tools.
    • Collaboration and open-mindedness are essential in a tech-driven world.


    Sound Bites

    "We are Monolith."

    "It's time to embrace the change."

    "Own the innovation, not the product."


    Keywords

    monolith, automation, design, AI, innovation, systems thinking, creativity, human-computer interaction, storytelling, organizational culture
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    1 hr and 19 mins
  • The Right Mindset

    The Right Mindset
    Jun 30 2025

    In this conversation, Cameron Craig and Keith discuss the evolution of digital retail, the role of AI in modern business, and the importance of a design mindset in navigating corporate challenges. They explore how crises can create opportunities for innovation, the significance of collaboration, and the impact of fear in corporate culture. The discussion also touches on the need for ownership in the design process and the challenges faced by companies like Macy's in adapting to a rapidly changing landscape. In this conversation, Cameron Craig and Keith discuss the importance of navigating organizational realities, the evolving role of design in business innovation, and the need for designers to take ownership of their work. They emphasize the significance of mindset, collaboration, and finding support systems in a rapidly changing environment influenced by AI and other technological advancements. The dialogue highlights the necessity for designers to adapt, innovate, and actively engage in their organizations to thrive in their roles.



    Chapters
    00:00 Introduction and Setting the Scene

    02:14 Identifying Opportunities in Crisis

    05:56 The Evolution of Digital Retail

    10:08 AI's Role in Modern Business

    12:50 The Ghost Kitchen Analogy

    15:36 Design Mindset and Innovation

    21:30 Ownership and Collaboration in Design

    26:01 Navigating Fear in Corporate Culture

    30:59 Company-Wide Dilemmas and Solutions

    36:20 Navigating Organizational Realities

    39:35 The Role of Design in Business Innovation

    42:27 Evolving Design Practices

    47:39 Taking Ownership and Responsibility

    01:03:01 Mindset for Designers

    01:09:29 Finding Your Support System

    Takeaways

    • There is usually an event that drives people to action.
    • The call to action often involves becoming more efficient.
    • AI is seen as a solution to many operational challenges.
    • Design is a universal language of psychology.
    • Ownership in design should focus on the process, not the product.
    • Fear in corporate culture can stifle innovation.
    • Understanding company dilemmas is crucial for effective design.
    • Collaboration is key to overcoming corporate challenges.
    • The evolution of digital retail has changed consumer expectations.
    • AI can help personalize customer experiences. Be deliberate about the choices you make in business.
    • Understanding different realities within an organization is crucial.
    • Design can help think through problems in lower-risk ways.
    • Designers need to evolve beyond traditional interface design.
    • Taking ownership of your work enables others to succeed.
    • Understanding the framework of your organization is essential.
    • A hacking mindset can help navigate challenges.
    • Find a partner to bounce ideas off and validate your thoughts.
    • AI is coming for low-level tasks, not for designers' creativity.
    • Intentional decision-making is key in design and business.


    Keywords
    design, innovation, AI, digital retail, corporate culture, ownership, crisis management, opportunities, Macy's, technology, organizational dynamics, design innovation, design practices, ownership, mindset, support system, AI in design, business strategy, collaboration, design leadership


    Alternate Titles

    Navigating Opportunities in Crisis

    The Evolution of Digital Retail and AI

    Design Mindset: Innovation in Corporate Culture

    Ownership in Design: A New Perspective

    Fear and Innovation in Corporate Environments

    Company-Wide Dilemmas: Identifying and Solving

    The Ghost Kitchen Analogy in Business
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    1 hr and 15 mins