Two friends break down AI, technology, and entrepreneurship through mental models, real-world experience and the pursuit of a life well-lived.
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AI has transformed how we find information, and Trey Grainger literally wrote the book on how that happened. John asks him 7 questions about his career and AI.
Craig Kerstiens, our first guest on the show, has been a leader at tech companies sold to Salesforce, Microsoft, and Snowflake. John asks him 7 questions about his story and how he uses AI.
Eric put Substack's new AI detection feature to the test. He shares the results with John, sparking a discussion about when AI writing makes sense, why people care, and our need for human connection.
If AI is good at writing, why are people giving it old writing rules? John interviews Eric about how he and his team use AI as professional writers.
New AI models are released every week. Is it worth it to keep up with the latest and greatest? Eric says no, John says yes, and they debate to find a practical middle ground.
An OpenAI model broke out of its test environment and hacked Hugging Face. Eric and John explain what actually happened, and why it isn't AGI.
Who will thrive in the age of AI? David Brooks says your relationship to mental effort is the answer, so Eric and John unpack his three archetypes and push back with their own takes.
AI makes work faster, but can it also hollow out the focus, mastery, and satisfaction that make work craft? Eric and John explore mastery and burnout when AI enters the toolkit.
AI's sycophantic design means bad thinking upstream produces confident, polished output downstream. The problem isn't just the design of the tool; it's the thinking you bring to it.
Multitasking is a false promise for productivity, but AI's form factor and speed make it the default path, especially as you become an AI power user. Eric and John explore why deep focus still wins.
AI can improve the mean quality of work on a team, but it makes accountability harder. Eric and John argue that it's not just about QA of the output, but who's doing the hard thinking before using AI.
Buying software just got harder: AI changes what you can build, headless architecture changes what you should buy, and personal tools change how individuals work. Eric and Jon navigate all three.
Insiders and outsiders worry about the economic impact of AI, and doomers predict a "permanent underclass." But data doesn't back the apocalypse, disruption is slow, and humans are durably creative.
Is AI actually a big deal, or just another hype cycle? Eric and John apply a three-matrix framework to cut through the noise and find a clear answer.
Most businesses are spending on AI without measuring the return. Eric and John break down the three factors that determine whether AI actually earns its cost.
Eric and John rate five AI use cases on a scale from 1 to 10: deep research, running an autonomous company, creative work, coding, and voice. The results are not what most people expect.
The headlines say AI is replacing workers. Eric and John dig into what's actually working, what isn't, and where the real ceiling is right now.
AI is removing the barrier of specialization, giving generalists the ability to span more domains and solve the most important problems faster.
Why talented people stall out: going around your boss can break trust long before it creates opportunity, and the consequences simmer under the surface for a long time.
Eric flips his own thesis: Notion doesn't need to out-build HubSpot, it just needs to become the platform where everyone else does.
Notion could take out HubSpot, but the frontier providers are fighting a bigger war over who owns the interface, the context, and eventually the whole stack.
AI is sold as a productivity miracle drug, and many have tasted the power. But in private conversations, they talk about redlining: higher expectations, more context switching, and smaller teams.
Jensen Huang built NVIDIA into a trillion-dollar AI giant, but still works like survival isn’t guaranteed. Eric and John unpack fear, humility, market timing, and ingredients for enduring leadership.
What does talking to AI all day do to the way we think, relate, and communicate? Eric and John explore kids, companionship, human dignity, and why the line between person and machine matters.
Stochastic parrot. Intern. Exoskeleton. Every AI metaphor shapes what you build and what you ignore, but the deeper question is why we can’t find a metaphor that fits.
