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The Monolith

The Monolith

By: Keith Conway Cameron Craig
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About this listen

Explore the evolving world of design with Cameron Craig and Keith as they tackle the challenges of complex, monolithic products and the critical role of human-centered design. Each episode dives into topics like organizational change, the future of design in tech, and the emerging influence of agents on user experience. Perfect for designers, strategists, and leaders, this podcast offers insights on adaptability, communication, and the strategic thinking needed to thrive in a rapidly changing landscape.© 2025 Keith Conway, Cameron Craig Art Economics Management Management & Leadership
Episodes
  • Be Like Dave: Ride The Next Wave
    Jan 30 2026

    What if the Monolith was never a warning, but a training program?


    In the Season 2 premiere of The Monolith, Keith and Cameron use Arthur C. Clarke’s 2001: A Space Odyssey as a lens to explore the moment we’re living in now: a convergence of AI, ambient computing, geopolitics, economics, and human evolution. From banned AI shopping agents to sketchy hardware supply chains, to HAL’s conversational intelligence and today’s emerging human–computer symbiosis, they trace a pattern that’s been unfolding for decades. The conversation reframes AI not as a tool to be feared or mastered, but as an evolutionary pressure that rewards generalists, systems thinkers, and those willing to adapt. This episode sets the tone for a new season focused on navigating exponential change, by staying light, curious, and human.


    Timestamps

    • 00:00–05:00 Season reset, futurism framing, eBay vs AI agents
    • 05:00–10:00 Ambient intelligence and embedded systems
    • 10:00–16:00 Hardware, supply chains, and hidden vulnerabilities
    • 16:00–25:00 Introducing the Monolith (Arthur C. Clarke)
    • 25:00–31:00 Evolution, experimentation, and “adapt or die”
    • 31:00–40:00 HAL, HCI, and conversational intelligence
    • 40:00–46:00 Generalists, systems thinkers, and survival
    • 46:00–52:00 Centralization, control, and economic tradeoffs
    • 52:00–57:00 Lightening the load: skills, identity, detachment
    • 57:00–1:01:00 Becoming the Monolith, Season 2 thesis


    Key Takeaways

    1. The Monolith represents an evolutionary training mechanism, not a villain
    2. AI functions as ambient intelligence, not just a discrete tool
    3. Legacy marketplaces and systems are actively resisting adaptation
    4. Hardware and supply chains are now major vectors of risk and power
    5. Generalists outperform specialists during periods of rapid change
    6. Human–computer interaction is shifting toward conversational symbiosis
    7. Centralized intelligence creates economic and social tradeoffs
    8. Curiosity is a prerequisite for autonomy in an AI-driven world
    9. Letting go of outdated skills and identities is a survival strategy
    10. To change the system, you must understand and partially become it


    Keywords

    Arthur C. Clarke, The Monolith, 2001 A Space Odyssey, AI agents, ambient intelligence, systems thinking, generalist mindset, human computer interaction, hacking mindset, economics, astrology and cycles, exponential change, futurism, design as a verb

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    1 hr and 1 min
  • Season 1 Finale: Curiosity Leads to Faith
    Jan 30 2026

    Description

    What happens when the systems we trusted stop working, and curiosity becomes the only reliable strategy left? In this Season 1 Finale, Keith and Cameron reflect on a brutal year of technological acceleration, economic pressure, and cultural whiplash, and argue that we are far earlier in the story than we think. From AI collapsing traditional roles, to Saturn–Neptune marking a once-in-millennia reset, they explore why clinging to old identities, metrics, and hierarchies is now the riskiest move you can take. Drawing from lived experience inside Amazon, Macy’s, and high-stakes design environments, the conversation reframes curiosity not as a personality trait, but as a survival skill. When fear dissolves and attachment loosens, something unexpected appears: faith—not blind optimism, but confidence born from pattern recognition, systems thinking, and the courage to experiment. The episode closes the season by asking how we navigate profound change without losing our humanity.


    Timestamps

    • 00:00–07:00 End-of-year exhaustion, signal vs. noise
    • 07:00–15:00 AI acceleration and “we’re earlier than we think”
    • 15:00–24:00 Media narratives, simulation, and manufactured reality
    • 24:00–34:00 Escapism, analog longing, and human grounding
    • 34:00–46:00 Design, automation, and the collapse of role boundaries
    • 46:00–58:00 Power shifts, economics, and responsible disruption
    • 58:00–1:10:00 Letting go, lightening the load, non-attachment
    • 1:10:00–1:20:00 Curiosity, faith, and the Season 2 thesis


    Key Takeaways

    1. We are at the very beginning of a long technological cycle—not the end
    2. Curiosity is a strategy, not a personality trait
    3. Fear narrows options; curiosity expands systems awareness
    4. AI shifts power toward those who can frame problems, not just execute tasks
    5. Legacy metrics (KPIs, org charts) lag behind reality
    6. Letting go is a prerequisite for adaptation
    7. Design thinking becomes dangerous—in the best way—when paired with automation
    8. Human connection is resurfacing as a counterbalance to abstraction
    9. Faith emerges from pattern recognition, not blind belief
    10. The people who thrive next are cross-disciplinary, experimental, and ethically curious


    Keywords

    Design thinking, systems thinking, AI disruption, astrology and cycles, Saturn Neptune, hacker mindset, corporate culture change, exponential technology, curiosity, faith, economic transition, leadership, meaning, post-COVID systems

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    1 hr and 23 mins
  • 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
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