ON_Discourse

Andrew Rosen’s ESPN vs. NYT breakdown is generating headlines, not because it’s about sports or news, but because it’s about institutions facing disruption. This episode doesn’t just recap his argument, it asks a harder question: What does it look like when legacy brands adjust too slowly to seismic shifts in distribution, personalization, and participation? Details in the Show: * Why Rosen says N...

Toby, Dan, and Chmiel set out to decode vibe coding but end up in a more urgent conversation about thinking. What happens when our tools get smarter, but our minds get lazier? Who wins in the battle between machine automation and human inspiration? Details in the Show: * How vibe coding is amazing (and frustrating) * The rise of synthetic synthesis and what it’s doing to original thought * How AI...

Toby, Dan, and Chmiel dig into the implosion of Gartner’s market cap, and what it reveals about the future of knowledge work. The conversation starts with a provocative question: if the business of certifying value no longer creates value, what’s next? Details in the Show: Why Gartner lost half its value The crumbling authority of research firms in a world of AI-generated synthesis Why “knowledge...

Toby, Dan, and Chmiel examine LinkedIn’s strange grip on our professional lives. What starts as a confession, Toby admitting to opening the app 30 times a day, turns into a bigger question: is LinkedIn a tool, a feed, or just another dopamine trap? Together, they unpack why the platform feels indispensable yet indistinguishable from TikTok or Instagram, and what that says about the state of “profe...

Chmiel sits down with ON_Discourse members Natalie Monbiot and Craig Elimeliah for a sharp dive into AI’s hidden cost: the erosion of human cognition. Natalie, founder of Virtual Human Economy, shares research showing how over-reliance on LLMs can short-circuit learning, while Craig, Chief Creative Officer at Code and Theory, explores how design choices can either feed (or fight) that decline. Tog...

Toby and Chmiel continue last week’s conversation on human ingenuity with a founder who’s putting it to the test. Katherine von Jan (KVJ to those who know her) joins the pod to talk about her new venture,  Tough Day , and its mission to unlock the best of human potential in an AI-saturated workplace. As a longtime ON_Discourse member and former Salesforce exec turned startup founder, KVJ has...

Toby, Matt, and Dan wrestle with what it means to have a “voice” in an AI-mediated world, and what happens when that voice gets flattened, filtered, or faked. This episode digs into the paradox of human ingenuity in the age of synthetic output, the strange intimacy of talking to machines, and why friction, not fluency, might be the future of AI design. Details in the Show Why AI-generated content...

Toby, Dan, and guest Craig Hepburn step inside the AI browser wars, and ask if the future of the internet is being quietly rewritten not by models, but by interfaces. This episode zooms in on Perplexity’s new agentic browser Comet , the real promise (and limits) of context-aware assistants, and what gets lost when AI "helps" too much. Details in the Show Why “the browser” might be AI’s most import...

Toby, Dan, and Chmiel interrogate the quiet crisis hiding inside the AI boom: we’re offloading too much thinking and calling it strategy. This episode explores what gets lost when cognitive offloading becomes the norm, and why the future of leadership may depend on friction, not flow. Details in the Show Why “upstream of strategy” isn’t just a catchphrase—it’s a call to rethink how we think Cognit...

Dan, Toby, and Chmiel go behind the scenes of Cannes Lions to unpack the real programming, posturing, and potential shaping the creative industry’s biggest week. Is the future of advertising being written on the main stage or whispered behind closed doors? Details in the Show Why the most important conversations at Cannes don’t happen on stage How closed-door programming became the sharpest tool f...

In this episode, we’re joined by Taylor Halsted of Shamrock Capital to interrogate the illusion of AI efficiency. What if the mess we’re trying to automate out of work is actually where creativity, connection, and culture live? Details in the Show Why “Head of AI” might be the new “Webmaster”—and just as misguided The difference between performing productivity and producing outcomes Whether AI is...

Toby sits down with Henrik Werdelin and Nicholas Thorne, co-authors of Me, My Customer, and AI , to interrogate the optimistic thesis at the heart of their book, and the paradoxes it reveals. From donkeycorns to Dunbar numbers, this session explores what happens when everyone is an entrepreneur, and no one stands out. Details in the episode: Why founder–customer fit matters more than product–marke...

Toby and Dan track the decline of Google Search, the end of SEO, and what’s replacing it: group chats, agentic systems, and personalized internets built around behavior, not clicks. Details in the episode: Why search is collapsing (and what’s replacing it) How generative AI is reshaping discovery and intent What the “human internet” might look like Why the future isn’t conversational—it’s contextu...

We have been hosting closed-door, private Group Chats at ON_Discourse for 2 years. In this episode, Toby and Chmiel talk about the ON_Discourse version of group chats and how they are different than the contentious, political experience that was recently profiled by Ben Smith at Semafor . Details in the episode: How the pandemic inspired group chats How group chats are the future of media Why trus...

Toby and Dan turn a weekly meeting into an impromptu podcast recording about the future of digital strategy and why notifications suck. Details in the episode: Requirements are dead The design supply chain Fast vs Slow creativity Learn about ON_Discourse . About ON_Discourse ON_Discourse is a private community of C-suite leaders, investors, and innovators who come together to challenge assumptions...

Toby interviews a couple teenagers who are vibecoding their way through the modern internet. This conversation reveals an alternative perspective on the AI revolution, from a generation that never knew a world without the web. Details in the show: Will there be an internet in 5 years? Who do you trust online? What is your AI stack? A new acronym is coming: RLHF Learn more about ON_Discourse . Abou...

Toby interviews Suzy co-founder and CEO, Matt Britton, about his forthcoming book Generation AI: Why Generation Alpha and The Age Of AI Will Change Everything. This interview was conducted during a closed-door Member event. Detail in the show: The Goonies Expertise vs Knowledge How to prepare your kids for adulthood in AI era Learn more about ON_Discourse . About ON_Discourse ON_Discourse is a pri...

Dan, Toby, and Chmiel welcome (but don't introduce) Craig Hepburn to the conversation. Craig is the Chief Product Office at Art Basel who recently introduced a new AI-powered app. Dan opens the conversation with an anecdote about an AI agent that keeps delaying its work. It sparks a conversation about the unmet potential of AI (so far). Details in show: Surfing instagram Has AI changed anything? V...

Dan and Chmiel invite Henrik Werdelin, co-founder of Barkbox and PreHype, to talk about how unicorns are old news and how donkeycorns are the future. You’ll hear about how agentic AI can prompt wannabe entrepreneurs into actual founders. This is a small idea that can transform the economy. Details in show: Small ideas win Human creativity wins Agentic AI as a tool Learn about ON_Discourse . About...

Toby, Dan, and Chmiel officially announce The ON_Discourse Summit - Solve Small: AI Transformation for the C-Suite. This event will be held on March 26, 2025 in New York City. Request an invite. Details in show: Defining 'Solve Small' Bad friction in the workforce Details about the summit Learn more about ON_Discourse . About ON_Discourse ON_Discourse is a private community of C-suite leaders, inv...

Dan returns to the podcast to talk about the off-the-record conversations he had at Davos. Toby and Chmiel used the LinkedIn post he wrote about his trip to scrutinize the level of discourse about AI transformation. The key takeaway: no one knows what happens next. Details in the show: Innovation vs Integration The future of the workforce What is creativity Learn more about ON_Discourse . About ON...

Toby and Chmiel reflect on the future of managers. They ponder the value of the role and whether AI can enhance or replace it. All of the perspectives you will hear come from a recent Group Chat they hosted that was shaped and sharpened by ON_Discourse member Katherine von Jan, founder of tough.day , an employee resilience AI tool. Her exploration of the future of management is revealing a new set...

Toby, Dan, and Chmiel argue about Boardy, an AI-bot that crawls LinkedIn, calls you on the phone, asks you personal and probing questions, listens and interprets your answers, and then makes contextual introductions to similar strangers from different networks. Is this what we are talking about when we talk about the future of AI? Details in the Show: How do we define a good AI innovation? Is Boar...

Toby and Chmiel break down their trip to CES, where ON_Discourse hosted multiple tours of of the exhibition floor. They talk about the "Agentic Era" on display at the show and how a new audience of industry executives responded to their discourse method. Details in the show: AI Agents - the Agentic Era Small Language Models LG and agents at home Learn more about ON_Discourse About ON_Discourse ON_...

Toby and Dan talk about their trip to Lisbon for Web Summit, legal protections for agents, and why the internet sucks (and how it could be better). We talk about: AI Startups The Colorado AI Act Why the internet sucks Interested in becoming an ON_Discourse member? Learn about membership here . About ON_Discourse ON_Discourse is a private community of C-suite leaders, investors, and innovators who...