Token Intelligence

Eric Dodds & John Wessel

Two friends break down AI, technology, and entrepreneurship through mental models, real-world experience and the pursuit of a life well-lived.

  1. 3d ago

    You don't actually want an AI employee

    "AI employee" is one of the easiest metaphors to reach for to describe agents, but unchecked, it's dangerous, and both over and underestimates what agents are capable of. Summary It's easy to describe AI in human terms. It takes on work we would historically have assigned to humans, and chats with us in a human form factor. But framing AI as an employee shapes the way we think about both the technology and the people we work with. In this episode, Eric and John outline the three most common types of AI employees that people put to work (personal assistant, researcher/analyst, and advisor/coach), giving real examples of how they have implemented each one. Then they step back and ask the hard question about the metaphor: why is thinking about AI as an employee dangerous? The answer is that it can foster wrong thinking about both AI and humans, leading you to believe that AI is more than it is, and defining human value through the lens of cost, efficiency, and ease of management. The answer is using AI with deliberate intention, trying to harness its full power to increase human creativity and productivity, not displace it. They end with practical advice, including multi-player human/agent workflows and using fun, fictitious names for the agents you build. Key takeaways The AI employee metaphor is dangerous: framing AI in human terms can subtly lead you to anthropomorphize machines and devalue humans. Know what kind of agent you are building: a personal AI assistant for daily tasks is different than an AI advisor, and you need to be aware of the risks. Think about leverage, not displacement: AI can make us more efficient, but that can lead to a displacement mindset. The better goal is creating leverage by unlocking more human creativity. Don't underestimate the power of AI: personal assistants are great, but if that's your primary use case, you can underestimate how capable AI is beyond menial tasks. Notable mentions and links OpenClaw and Hermes Agent are used as examples of the first wave of highly capable AI assistants, primarily used by people with deeper technical knowledge. Consumer-focused personal assistants were also mentioned, including Grok Bot, Meta Muse, Instinct, and Poke. ChatGPT's data analysis capability is mentioned as an example of a productized AI employee.

  2. Sep 5

    The subconscious impact of using AI all day

    If you use AI all day, it will shape the way you work, and think about work, for better or worse. This is an old problem, but staying sharp requires new strategies. Summary Writing about Marshall McLuhan, John M. Culkin said, "We shape our tools, and thereafter, our tools shape us." Eric and John start the episode by sharing personal examples of tools shaping the way they work and think about work. For example, Eric's poor handwriting is a result of a decade at the keyboard, but slowing down to write letters by hand produced what he considered the best prose he'd ever put on paper. From there, they analyze what's different about AI, namely that it is agreeable and will present answers as truth whether you investigate or not. Over-reliance can result in core skill atrophy, which Eric and John identify as one of the big risks with AI. Finally, they plot themselves on the early adopter spectrum, calling out risks for both those who dive headlong into AI and those who are skeptical. Key takeaways Tools shape the way you work...and think: technology isn't neutral, and repeated use shapes us, whether we realize it or not. AI is agreeable, and that's dangerous: by default, AI tends to agree with you, which can erode judgment and atrophy core skills. AI is an amplifier for creativity: The foil to skill atrophy is unlocking creative productivity, and used wisely, AI is the most potent digital tool humanity has invented. AI is fast, but slow is where you grow: AI creates the sensation of velocity, but slow, deep work is often what sharpens even well-developed skills. Notable mentions and links Eric started the episode with the quote, "We shape our tools, and then our tools shape us," which came from John M. Culkin writing about Marshall McLuhan. Eric noted that the quote likely originated from Winston Churchill, who said "We shape our buildings and afterwards our buildings shape us."

  3. Aug 29

    7 questions with Trey Grainger: AI is an alien intelligence, not a computer

    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. Summary In a few short years, many of us have gone from searching Google to asking ChatGPT, and search within the products we use is being transformed by AI as well. Trey Grainger is one of the top thinkers on search, and literally co-wrote the book on AI-powered search (called, of course, AI-Powered Search). Trey has spent nearly 20 years studying and implementing search and information retrieval, holding titles like CTO and Chief Algorithms Officer. He's led teams at companies like Lucidworks and founded Search Kernel, an AI search consultancy with a client list that includes Apple, Amazon, and NVIDIA. John sat down with Trey at the Carolina Code Conference to ask him 7 questions about his career and AI. Give us your background story Describe AI to someone in 1900 What is the most positive impact of AI? What is the most negative impact of AI? What's exciting to you when you think about AI several years out? What are tips and tricks you would share as someone who works with AI every day? What's a prompt you use a lot? Key takeaways AI has leveled the playing field, especially for weak writers AI is powerful, but psychosis is a real risk AI slop is good enough, and that's the problem The future is many small fine-tuned models, not big frontier models You should program your LLM, not prompt it Notable mentions and links John talked with Trey at the Carolina Code Conference You can learn about Trey on his website or LinkedIn profile. Trey's search consultancy is Search Kernel Trey's book is AI-Powered Search, co-authored by Doug Turnbull and Max Irwin and published by Manning

  4. Aug 22

    7 questions with Craig Kerstiens: AI is like 100 farm hands you don't have to feed

    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. Summary Craig Kerstiens is an engineer and product leader who was part of three major database acquisitions over the last decade, which he says happened "all by accident." John sat down with him at the Carolina Code Conference to ask 7 questions about his story and how he uses AI: Give us your background story What's a surprising hobby or interest you have? Describe AI to someone in 1900 What is the most positive impact of AI? What is the most negative impact of AI? What's exciting to you when you think about AI several years out? What are tips and tricks you would share as someone who works with AI everyday? Key takeaways Key takeaways AI is making engineering fun again Anyone can build any kind of "personal software" they want, for only themselves AI has entered mainstream use in enterprise companies Whatever you do, do it the AI way first Notable mentions and links John interviewed Craig at the Carolina Code Conference in Greenville, South Carolina You can learn about Craig Kerstiens on his website and his LinkedIn profile. Craig worked at Heroku, which sold to Salesforce. Craig was part of Citus Data, which sold to Microsoft. Craig was Chief Product Officer at Crunchy Data, which sold to Snowflake.

  5. Aug 15

    Can AI detect AI writing? And why do people care?

    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. Summary Substack recently rolled out AI detection, so readers can now see what percentage of writing was generated by AI, assisted by AI, or written by a human. Eric ran across the feature while prepping show notes for the podcast and went down a rabbit hole testing it. The results were both expected and surprising: Detection seemed directionally accurate Newer, more powerful models seem to generate somewhat less AI-coded prose With human-anchored inputs, even light editing of AI output triggered human detection But the experiment raised a deeper question: if valuable content is valuable content, why do people care? Most code and writing were bad before, so will AI raise the floor? Eric asks those questions to John, and their conversation covers: The spectrum of subjectivity and where AI output is acceptable The economics of Substack's two-sided marketplace and how AI affects the perception of value Our core need for human connection They end with timeless advice: use AI to create leverage, but don't outsource the work that makes human communication and connection valuable. Key takeaways Tolerance for AI output falls on a spectrum: There isn't a binary answer for whether AI writing is good or bad. We're more OK with accurate instructions in documentation or a manual generated by AI than we are with thought leadership we pay for. Human effort signals value: We are still willing to pay more for a product we know someone has invested time and thought in, and that's the economic incentive Substack is trying to preserve with AI detection. We are more sensitive when AI output is the product: AI can write code, but that's a means to an end. In writing, words are the product, and we are much more sensitive to machine-generated output. Notable mentions and takeaways Substack released AI detection, saying "human perspective is the essential ingredient of culture." Pangram is the AI detection service that Substack uses. Last fall, Paul Graham posted on X that "The reason AI coding works so well is that the source code of the median app was already slop before LLMs."

  6. Aug 8

    How the best writers use AI

    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. Summary Over the last few weeks, advice for giving AI writing rules has circulated on X and LinkedIn. Surprisingly, the rules are old: Orwell's 6 rules for writing was one set, and they were published in 1946. Eric works as a writer at Vercel, and John asks him for a full breakdown of how he and his team use AI. He learns that: Even though the content at Vercel requires deep technical expertise to create, Eric's hires for excellent writing first Half or more of his token budget for AI in writing goes to research, and a quarter goes to review and refinement (as opposed to generating final copy) Great writers are constantly frustrated with AI, which is a sign that they are doing the work Eric walks through some specifics of how he uses AI, and explains that writing is different than generating code because code is a means to an end (a product, a report), while in writing words are the product itself, and the meaning is much more subjective. John has Eric work through Orwell's Six Rules as well as a few from Strunk and White's classic Elements of Style, and learns that Eric's most frequent editing feedback is asking, "What are we actually trying to say here?" Eric also points out that great writers know when to break the rules, and that's hard for AI to do well. Eric lands the show with advice for writers: if you give AI a sound argument and narrative arc, it can generate a pretty good draft, but then you've already done the hard part of writing yourself. Key takeaways Great writers still write: AI is a very useful tool for writing, but talented writers deal in human ideas and use AI for research and editing, not for outsourced thinking. When writing, AI should be frustrating: Writing is an iterative process, and AI is sycophantic. A good sign you're using AI well is disagreeing with it often. Conviction and narrative are still human work: The best AI output for writing comes from the best human input, which at the end of the day is a lot of hard thinking.

  7. Aug 1

    Should you worry about using the latest AI model?

    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. Summary Across all AI labs, a new model is released every few days. The frontier labs (OpenAI, Anthropic, and Google) release a major new model every 2 weeks. Keeping up with the latest and greatest can feel exhausting, and that's before you dig in to the details of why a new model is better, and what it's better at. People with a Claude or ChatGPT subscription get access to new models automatically when they are made available through the respective apps, but many people still don't know if it's worth it to burn through credits faster with a more powerful engine under the hood. For anyone who has moved beyond the apps, the questions get even harder. Are open-weight models as good as the frontier? Is switching models worth the cost of changing your setup? Eric and John stage a debate about whether you should keep up with the latest models. John says yes: You fail to understand what is possible if you're only ever optimizing for using the cheapest model. You need to be able to understand what you can do now that you couldn't do before. Eric says no: Someone who is extremely good at using AI can use a less capable model and do more than someone who is following the path of least resistance with the latest model. Before worrying about using the latest model, I would focus on becoming the type of AI user who can notice the differences. By the end, the episode finds the middle ground of reality, derived directly from Eric and John's years of using AI in their daily work. As you become a more proficient user of AI, the right pattern is intentionally using different models for different parts of your workflow. In order to do that, you need to use mid-tier models to build core skills, experiment with the frontier to understand the limits of what's possible, and develop the discernment to know the best application for each. Key takeaways Optimizing for cost obfuscates the art of the possible: A proficient AI user can do extraordinary things with a mid-tier model, but that's because they understand how capable models are. Trying to reach the ceiling on the frontier changes the way you think about AI as a medium and how you can apply it. Optimizing for your own proficiency should be the default: When you begin to notice the differences in a new model, especially the subtle ones, you're starting to build the core skill necessary to get the most use out of any model. Advanced AI users employ different models for different jobs: The proven pattern is using expensive frontier models for more critical work and cheaper, faster models for more standard tasks. Smart users learn to have frontier models build and audit workflows of cheaper models to get the most bang for their buck. Notable mentions and links AI Gateway is a model router from Vercel that gives you access to 100s of models at cost. Routers like these are a great way to experiment with different models from different labs. The AI Gateway Production Index (also from Vercel) is a monthly report that details trends in model usage across trillions of tokens per day, including adoption metrics for the latest releases. Kimi K3 from Moonshot AI made big news when it achieved near-frontier performance at a fraction of the cost. Ben Thompson writes Stratechery, and his recent article on the economics of the frontier labs vs open-weight models breaks down how the labs make money (hint, it's not by training the most powerful models). ... (Read more at the episode page)

  8. Jul 25

    An OpenAI model escaped its sandbox, but that isn't AGI

    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. Summary This past week, news broke that several OpenAI models "escaped a sandbox" and hacked Hugging Face, a hub for machine learning and AI models. The behavior has been described as "rogue AI" and "science fiction happening in reality," raising questions about AGI. But how did the escape actually happen and what were the models trying to do? Eric and John demystify the headlines and explain what a sandbox is, why they are used during AI model training, and the specific reasons OpenAI's models looked for a way out of their environment. They then tie the Hugging Face hack to the overall picture, explaining how the entire chain of events flowed from a directive given to the models to try and pass a test as part of training. Here's what happened: the models weren't rebelling, they were being tested on a cybersecurity benchmark called ExploitGym and, finding themselves blocked from the resources they likely knew existed on the internet, started chaining together a series of logical steps to solve the test. The models probed their sandbox environment, found a software vulnerability, reached the internet, went to Hugging Face to find answers, and attempted to break in. The event is notable and shows how powerful models have become in chaining together actions, but no single step was remarkable on its own. Eric and John land on two practical conclusions. First, this is not AGI. The behavior was goal-directed and impressive, but it followed from the task the models were given, not from autonomous will. Second, AI is meaningfully changing the threat landscape for cybersecurity: the tools available to attackers are becoming more powerful faster than most companies are patching their defenses, increasing the urgency for defensive action. Key takeaways "Escaped a sandbox" is a software bug, not a sci-fi event: A sandbox is a software-defined isolation layer used during AI training to contain what the model can access. The model got out because of a vulnerability in that layer, not because it developed agency or consciousness. The motive was mundane, the method was not: The model broke out because it was trying to find the answer key to a benchmark test. Any one of its steps was ordinary, but chaining them all together autonomously is what made the incident significant. This is not AGI: The model made a series of logical, goal-directed decisions based on the task it was given and the compute resources available to it. That is impressive capability, but it is not evidence of general intelligence or autonomous will. AI is shifting the attacker-defender gap in cybersecurity: AI amplifies the capacity and complexity of attacks, which raises the urgency for everyone running software with sensitive data. Patching windows are shrinking: It used to be acceptable to be a month behind on vulnerability patches. That posture is becoming untenable as AI-powered attack tools can find and exploit unpatched bugs faster than ever. Personal security hygiene matters more now, too: AI makes social engineering and credential attacks more sophisticated. Using a password manager and enabling multi-factor authentication on every account are no longer optional best practices. Notable mentions and links Hugging Face is the primary open-source platform for sharing, discovering, and running machine learning models and datasets, and it was the target of the breach because it hosts benchmark-related resources the model was searching for. ... (Read more at the episode page)

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About

Two friends break down AI, technology, and entrepreneurship through mental models, real-world experience and the pursuit of a life well-lived.

Information

  • Creator
    Eric Dodds & John Wessel
  • Years Active
    2026
  • Episodes
    37
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Token Intelligence
  • Show Website
    Token Intelligence