thinkfuture: technology, philosophy and the future

chris kalaboukis
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Welcome to thinkfuture, where host Chris Kalaboukis explores the bold ideas shaping tomorrow. From AI-driven creativity and personal growth to leadership in remote work, this podcast delves into the intersection of innovation, technology, and human connection. With visionary guests and thought-provoking conversations, thinkfuture helps listeners unlock new possibilities, challenge the status quo, and create the future they want to see. Tune in for fresh insights, actionable strategies, and unexpected inspiration.

  1. 1D AGO

    1135 AI Won’t Replace You — But It Will Change What Matters | Peter Ashby-Smith on Stoic Futurism

    Subscribe for more: https://thinkfuture.comConnect with Peter: https://peterashbysmith.substack.com---What if the best way to survive technological chaos… is a 2,000-year-old philosophy?In this episode of thinkfuture, host Chris Kalaboukis speaks with Peter Ashby-Smith, Australian academic and author of The Stoic Futurist, about how Stoicism and futurism combine into a practical framework for navigating the AI era.Peter argues that most people are overwhelmed because they’re trying to control things they can’t. Stoicism offers a powerful reset: focus on what’s controllable, adapt to change proactively, and cultivate judgment over panic.And in the age of AI, that mindset may become essential.We explore:- What “Stoic Futurism” actually means- Why AI is automating execution—but increasing the value of judgment- The shift from “fiddlers” to “conductors” in the workplace- Why AI-proof skills are trust, clarity, and direction- How higher education risks becoming obsolete- Why universities must shift from content delivery to context-based learning- The rise of one-person AI-powered businesses- Why AI is a foundational technology—not magic AGIPeter believes we’re early in a hype cycle. The companies dominating AI today may disappear tomorrow—but the technology itself will become embedded everywhere.The real opportunity isn’t competing with AI.It’s learning how to direct it.

    39 min

  2. MAY 6

    1134 AI Is Killing Entry-Level Jobs | The “Messy Middle” No One Is Talking About

    subscribe here: https://thinkfuture.comconnect with mango aggro: https://techtensions.substack.com---In this episode of thinkfuture, host Chris Kalaboukis speaks with Mango Aggro (TechTensions Substack) about one of the most overlooked consequences of AI: the collapse of entry-level roles and the emergence of what he calls the “messy middle.”As AI automates junior-level tasks—like building presentations in minutes instead of days—companies are hiring fewer entry-level workers. That might look efficient today, but it creates a long-term problem:No pipeline of talent to replace tomorrow’s leaders.We explore:- Why AI is shrinking entry-level jobs across industries- The hidden risk of a future talent gap- How AI is being used (and misused) to justify layoffs- The rise of agentic AI—systems that act autonomously, not just respond- What “personal AI” could look like in the near future- Why job survival depends on shifting from process to outcome- The surprising rise in value of skilled trades vs. knowledge work- A possible future of post-scarcity and Universal Basic IncomeMango’s perspective is clear: AI isn’t just automating work—it’s restructuring how careers, value, and opportunity evolve.If you’re thinking about AI, jobs, career strategy, or the future of work, this conversation cuts through the noise and gets to the real implications.

    38 min

  3. APR 1

    1133 Why Success Isn’t Enough | Ashley Butler on Leaving It All Behind and Starting Over

    Read more: https://thinkfuture.comConnect with Ashley: https://notsorryashley.substack.comWhat if the life you built… isn’t actually yours?In this episode of thinkfuture, host Chris Kalaboukis speaks with Ashley Butler, entrepreneur, former physician, and founder of MySherry, about walking away from success—and what comes after.Ashley’s journey is anything but conventional. From growing up in poverty to building a career in medicine, then launching a fast-growing startup, she did everything “right.”And then she walked away.Not because it failed—but because it no longer aligned with who she was becoming.We explore:- The hidden cost of success and the “golden handcuffs” of high achievement- Why scaling a business can pull you away from your original mission- The decision to shut down a growing company instead of compromising values- A transformative moment in Sedona that reshaped Ashley’s perspective- The shift from achievement-driven living to authenticity- Her new venture, “Not Sorry”, focused on permission, power, and purpose- The future of technology vs. human reconnection- Why the next wave may be both more advanced AI and more human disconnection from techAshley’s story challenges a core assumption: that success is the goal.Instead, she asks a harder question—What if alignment matters more than achievement?If you’re navigating career shifts, identity, entrepreneurship, or personal reinvention, this conversation will resonate deeply.

    56 min

  4. MAR 18

    1132 AI Is Changing Business — But Trust Is Disappearing

    Every new technology disrupts business. From the fax machine to email to Slack, each wave of innovation has changed how organizations communicate, collaborate, and build relationships. Now AI is the next major shift. In this episode of thinkfuture, host Chris Kalaboukis speaks with Gal Borenstein about how artificial intelligence is reshaping marketing, sales, and leadership — and why the real challenge isn’t technology. It’s trust. Gal explains how digital communication has gradually replaced many of the human interactions that used to build trust between companies and customers. As automation increases, businesses must work even harder to create authentic brands and values-driven messaging. But many companies are rushing into AI adoption without a clear strategy. We discuss: Why every new technology initially faces resistance How digital communication has eroded trust in business The biggest mistakes companies are making with AI adoption Why AI should enhance human interaction, not replace it The generational divide in technology adoption What ethical, thoughtful AI integration looks like Gal believes the next 5–10 years will bring clearer governance, better data practices, and a more balanced relationship between humans and AI. But getting there requires something many organizations lack today: Intentional leadership. If you’re interested in AI, business strategy, marketing, leadership, and the future of trust in technology, this conversation explores the deeper implications behind the current AI wave.

    34 min

  5. MAR 4

    1131 We’re Entering a Post-Truth Internet | Lee on AI, Trust, and the Future of Content

    Read more: https://thinkfuture.comConnect with Lee: https://substack.com/@winterouroborosWhat happens when you can’t tell what’s real anymore?In this episode of thinkfuture, host Chris Kalaboukis speaks with writer Lee Winter (creator of Winter Ouroboros) about the erosion of trust online, the rise of AI-generated content, and whether “truth” will even matter in the next decade.Lee shares why he moved from X to Substack, citing the toxicity of algorithm-driven feeds and the decline of meaningful discourse. In contrast, he sees long-form platforms as a refuge for depth, nuance, and intellectual honesty.But the bigger conversation goes deeper.As AI-generated text, images, and video flood the internet, we may be entering a post-truth reality—where authenticity becomes nearly impossible to verify.We explore:- Why algorithmic feeds distort perception- The shift from short-form outrage to long-form thinking- The growing difficulty of verifying online content- Whether usefulness will replace truth as the dominant metric- The future of AI-generated media and digital anonymity- What privacy looks like in a world of total synthesisLooking ahead to 2036, Lee and Chris speculate about a world where AI content is the norm, not the exception—and where the ability to discern reality becomes a rare skill.If you care about AI, digital trust, social media, philosophy, or the future of online identity, this episode goes straight to the heart of it.

    35 min

  6. FEB 25

    1130 12 Failed Startups Before Success | Orel on WriteStack, Substack Tools, and Solopreneur Grit

    See more: https://thinkfuture.comConnect with Orel: https://writestack.io---What does it really take to build a product as a solo founder?In this episode of thinkfuture, host Chris Kalaboukis speaks with Orel, software developer and founder of WriteStack, a tool designed specifically for Substack creators to manage notes, content, and publishing workflows.Orel’s story isn’t overnight success. Before WriteStack, he built and shut down 12 failed startups. Instead of quitting, he used each failure as feedback—refining his understanding of product-market fit, marketing, and community-building.We cover:- Why most startups fail—and what you actually learn from them- The evolution of WriteStack from an AI outline tool to a full Substack productivity platform- The importance of listening to users and pivoting quickly- How community feedback shaped the product roadmap- What it’s like working 6 hours a day, 7 days a week as a solopreneur- Why marketing matters as much as code- The entrepreneurial mindset required to survive long-termOrel believes that even if AI eventually automates tools like WriteStack, the mindset of building, adapting, and serving a community will always matter.If you’re a Substack creator, indie hacker, solopreneur, or SaaS founder, this episode is a grounded look at persistence, iteration, and building tools for real users.

    31 min

  7. FEB 18

    1129 The Internet Is Over | Nick Richtsmeier on Trust, Techno-Feudalism, and A Humanist Alternative

    See more: https://thinkfuture.comConnect with Nick: https://www.trustmadegrowth.com---What if the open internet is already dead—and trust is the real battleground?In this episode of thinkfuture, host Chris Kalaboukis speaks with Nick Richtsmeier, founder of Trust Made Growth, about the collapse of digital trust and the rise of what he calls a techno-feudalist society.Nick argues that today’s digital world is dominated by rent-seeking platforms that neurologically overrun users with anxiety, exhaustion, and loneliness—the “Bermuda Triangle of the 21st-century human.” Businesses and creators face a stark choice:- Serve the platforms and become dependent on them- Or build a humanist alternative that restores agency and connectionWe cover:- Why trust is biological—a reptilian-brain function asking, “Will this person harm me?”- How digital platforms undermine that neurological trust signal- The concept of techno-feudalism and algorithmic control- Why AI is a “massive gift” that exposes the fraudulent nature of online interactions- The “dead internet” moment and the end of organic digital discovery- The “noticing meeting” method for rebuilding human connection- The search for the “3.5%” capable of driving social change- A 10-year vision for mercantile-style commerce beyond platform dependencyNick’s work is not about building another app. It’s about rebuilding trust at a human level—through deep listening, embodied leadership, and communities that prioritize connection over extraction.If you care about AI, digital trust, leadership, platform power, or the future of human connection, this episode will challenge how you see the internet—and your role in it.

    36 min

  8. FEB 11

    1128 Why “Move Fast and Break Things” Is Failing | Gaurab Bansal on Responsible Innovation

    See more: https://thinkfuture.comConnect with Gaurab: https://www.linkedin.com/in/gaurab-bansal/---What happens when technology moves faster than trust, regulation, and social systems?In this episode of thinkfuture, host Chris Kalaboukis speaks with Gaurab Bansal, founder of Responsible Innovation Labs, about why startups—especially those building AI and emerging technologies—can no longer afford to ignore responsibility, culture, and long-term impact.Gaurab explains that responsible innovation isn’t about slowing down progress—it’s about anticipating how technology will interact with people, communities, institutions, and power structures before friction and backlash emerge. As AI increasingly outpaces regulation, founders face growing tension with governments, civil society, and the public.We cover:- What “responsible innovation” actually means in practice- Why startups deploying AI often outpace regulation—and why that’s risky- How proactive engagement with regulators and stakeholders builds resilience- Why founders must think beyond product to systems-level impact- The role of company culture, mission, and values in attracting top talent- Why responsibility is becoming a competitive advantage—not a constraint- Gaurab’s vision for 2036, where AI and robotics enable human flourishingGaurab argues that responsibility won’t be optional in the future—it will be table stakes for companies that want to scale, survive, and earn trust.If you’re building in AI, emerging tech, startups, or innovation, this episode offers a rare, grounded look at how responsibility and progress can—and must—coexist.

    36 min
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About

Welcome to thinkfuture, where host Chris Kalaboukis explores the bold ideas shaping tomorrow. From AI-driven creativity and personal growth to leadership in remote work, this podcast delves into the intersection of innovation, technology, and human connection. With visionary guests and thought-provoking conversations, thinkfuture helps listeners unlock new possibilities, challenge the status quo, and create the future they want to see. Tune in for fresh insights, actionable strategies, and unexpected inspiration.

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