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. 2D AGO

    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

  2. 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

  3. 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

  4. 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

  5. FEB 4

    1127 Why Creativity Is Undervalued | Taylin John Simmonds on Monetization, Niches, and AI

    See more: https://thinkfuture.substack.comConnect with Taylin: https://taylinsimmonds.substack.com---Why is creative work so emotionally powerful—and yet so hard to monetize?In this episode of thinkfuture, host Chris Kalaboukis speaks with Taylin John Simmonds, musician, educator, and online creator, about the real challenges creatives face when trying to turn passion into sustainable income.Taylin shares his personal journey—from struggling as a musician to building a more stable life through teaching and online business—and explains why society consistently undervalues creative labor compared to “practical” skills, even though art plays a huge role in shaping how we feel, think, and connect.The conversation dives into the tension between creativity and commerce, and how creators can better position, test, and communicate the value of their work.We cover:- Why creative work is emotionally impactful but economically undervalued- The mindset shift required to monetize creativity without “selling out”- How platforms like YouTube can be used to test ideas and build audiences- The pressure to “niche down”—and why it doesn’t work for everyone- Taylin’s framework for niching: people, transformation, and brand- The rise of multi-passionate creators in a digital-first world- How AI could both threaten and empower creatives over the next decade - Why a balanced, nuanced view of AI matters more than blanket rejectionTaylin argues that as tools get more powerful, clarity, positioning, and human connection will matter more than raw output. Creativity isn’t disappearing—but how it’s valued is changing fast.

    59 min

  6. JAN 28

    1126 AI Is Tearing Tech and Creativity Apart | JP Prince on Hype, Backlash, and the Future of Art

    See more: https://thinkfuture.substack.comConnect with Jordan: https://www.jpprince.com---AI is everywhere—but not everyone wants it. What happens when tech hype collides with creative backlash?In this episode of thinkfuture, host Chris Kalaboukis speaks with Jonathan Smith (JP Prince), a technologist working inside VC-backed startups and the author of the upcoming cyberpunk novel The Mess. Living in both worlds has given JP a rare vantage point on one of the biggest cultural fractures of our time: AI in tech vs. AI in creativity.On one side, venture-backed companies where having an “AI story” is no longer optional—it’s mandatory. On the other, creative communities that increasingly see AI as an existential threat to human artistry. JP explains how these two realities collide in practice, often in uncomfortable ways.We cover:- The growing schism between tech’s AI hype and creative backlash- Why VC expectations now demand AI-driven hypergrowth- The concept of “receptivity”—why messaging fails when you ignore audience identity- AI fatigue from poorly implemented features and forced automation- How AI exposes how much modern work is low-value and performative- The business realities of publishing and why many authors are turning to self-publishing- Exploitation of artists, unfair contracts, and why unions still matterJP’s new cyberpunk novel The Mess, set in a future where corporations replace a collapsed U.S. governmentJP argues that AI’s most disruptive power isn’t creativity—it’s revealing how much of our work and systems exist purely to look productive.If you’re interested in AI culture, creative labor, tech hype, or the future of human value, this conversation goes far beyond surface-level debate.

    48 min

  7. JAN 21

    1125 Why School Still Looks Like a Factory

    See more: https://thinkfuture.substack.comConnect with Jordan: https://www.linkedin.com/in/jordon-millward-13115600---Our education system was built for the industrial age—so why are we still using it in the age of AI?In this episode of thinkfuture, host Chris Kalaboukis speaks with Jordon, a PhD student at Imperial College London and founder of Ask Jordon Ltd, an education consultancy focused on making learning more accessible, engaging, and future-ready.Jordon argues that modern education is still optimized for standardization, compliance, and rapid workforce onboarding—not for creativity, adaptability, or lifelong learning. As AI reshapes how knowledge is accessed and applied, he believes the traditional lecture-and-exam model is increasingly out of sync with reality.We explore:- Why the current education system was designed for factories, not futures- How exam-based assessment suppresses independent thinking- The case for competency-based and project-based learning- How AI could provide personalized, asynchronous support for students- Why teachers should shift from lecturers to facilitators- The risk of schools banning or over-standardizing AI instead of embracing it- A future divide between innovative “maverick” institutions and resistant onesJordon’s vision is bold but grounded: education should help people learn how to learn, not just memorize information. AI, when used correctly, could finally make that possible at scale.If you’re interested in AI, education reform, lifelong learning, or the future of work, this episode will challenge many assumptions you may still be holding.

    35 min

  8. JAN 14

    1124 Why the Future Is Getting Harder to Predict | Steve Brown on AI, AGI, and What Comes Next

    See more: https://thinkfuture.substack.comConnect with Steve: https://stevebrown.ai---What happens when technology moves faster than our ability to forecast it?In this episode of thinkfuture, host Chris Kalaboukis speaks with Steve Brown, veteran technologist, former Intel futurist, and former member of Google DeepMind’s AI research lab. With over 35 years of experience across high-tech, digital transformation, and AI, Steve offers a rare long-view perspective on where we are—and why predicting what comes next has never been harder.Steve explains how long-term forecasting used to be feasible when technological progress followed clearer trajectories. Today, breakthroughs in AI—and soon quantum computing—are compressing decades of progress into just a few years. The result is a future that’s accelerating faster than our institutions, economic models, and assumptions can keep up with.We cover:- Why 10-year technology forecasts are now nearly impossible- How AI is already accelerating progress in math, physics, and science- Why the combination of AI and quantum computing could reshape material science, chemistry, and biology- The likelihood of Artificial General Intelligence (AGI) arriving within 5–10 years- How AGI could disrupt jobs and force a rethink of capitalism itself- Why labor may increasingly turn into capital-The need for new economic models, shorter workweeks, or earlier retirement- How humans find meaning when machines handle most productive workSteve argues we may see more progress in the next five years than in the last fifty—and that the biggest challenge won’t be technological, but human.If you’re interested in AI, AGI, the future of work, economic disruption, or the limits of forecasting, this conversation offers a grounded, thoughtful look at what may be coming sooner than we expect.

    39 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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