Building ELEO v2 with full automation, getting Claude-pilled, and learning to ask the right questions Why have one coach, when you can have them all? In the physical world, that question seems preposterous. But with AI, it’s not only possible, it’s trivial. Thanks for reading A Trail Runner/Triathlete's Blog! Subscribe for free to receive new posts and support my work. And once that becomes true, something deeper shifts. You’re no longer optimizing answers, but instead focused on redefining the question itself. Asking an LLM to “build me a coach” or “build me a coaching system that incorporates all coaching advice the world has ever documented” is received as an equal problem. 1 As the window of context expands to the infinite, one has the power to ask all questions in absolutes. Herein lies the real power of AI - the ability to approach a problem with a magnitude that was previously impossible. AI is often described as an intern with 27 PhDs. But that analogy misses the point. This intern didn’t earn those PhDs sequentially, it learned them simultaneously, connecting ideas across disciplines and holding all of it in reach at once. That’s the real shift. Not better answers, but better questions. AI doesn’t fail because it lacks intelligence. It fails because we ask incomplete questions. The real skill isn’t prompting. It’s building a system that defines the boundaries, checks its own work, and stays aligned to the problem you actually care about. This is an “a-ha moment” that many miss. For example, you can’t ask an LLM “What are the benefits of K-Tape for athletic performance?” and then mock the LLM for not citing scientific studies 2 , when you could just have easily asked it “What are the scientifically proven benefits of K-Tape for athletic performance? Please cite your sources, and check your work for bias and accuracy”. The artistry of AI lies in not just in framing the question to fully tap the potential of AI, but in the ability to stay within the guardrails, double-check its own work, and thereby truly solve the problem at hand at in a whole new way with confidence. How does one do this? Some of you endurance nerds are curious like myself. For you, I present Part II of the exploration of using AI to create ELEO, a triathlon and running coach that can help you optimize training adaptation for your fitness goals . My goal with these articles is to (1) to help the digitally progressive among us get a deeper understanding of how to use AI, (2) explore the tools openly so you can build one for yourself, and (3) quite selfishly, build my own full-context AI coaching agent to nail my 2026 “A” race, Ironman Canada-Ottawa on August 2nd. For everyone else, you are welcome to skip this article. I am here to explore, not to defend the AI industry, or join in any pro- or anti-AI debate. 3 If you think AI is the Ragnarök of the middle class, you are more than welcome to your opinion. If you think I am anti-personal coach, do know that is 100% incorrect, and I still believe a personal coach is the single best investment you can make in your fitness journey. But I will also say that no one is more fascinated with ELEO than my personal coaches and doctors. The conversation is catalytic and efficient beyond anything previous, and has fundamentally changed how we work together. I bring ELEO to every appointment, and they often end up chatting with her directly as I work out. Recap Of Part I - ELEO v1, The CustomGPT In Part I, we built ELEO v1 as a CustomGPT . This was the first baby step from moving from simple prompts in ChatGPT, to a focused GPT that remembers who you are, all of your data, and the specific ways you would like it to be coached. What ELEO v1 unlocked in the ability to: Ask ELEO any coaching question, and get a reply with full context . She knows I am a 56-year-old endurance athlete, my race schedule and goals , my most recent labs and tests, and the tone I like for coaching. No reminders needed. Ask ELEO any coaching question, and get a reply with full context . She knows I am a 56-year-old endurance athlete, my race schedule and goals , my most recent labs and tests, and the tone I like for coaching. No reminders needed. Have ELEO build a custom training plan for one or more races , including mixing disciplines such as triathlon, running, ultrarunning, weight training, and more. All heart rate ranges and intensity are built from real labs and actual results in the field. Have ELEO build a custom training plan for one or more races , including mixing disciplines such as triathlon, running, ultrarunning, weight training, and more. All heart rate ranges and intensity are built from real labs and actual results in the field. Ask ELEO to adjust the training plan due to any real life interruptions , such as travel, sickness, family commitments, etc. You can also give it feedback from real life coaches or recent race results, and ask ELEO to adjust the plan, or just give an opinion. My swimming coach, Hillary, had some strong opinions on frequency of swim practice, and ELEO was happy to oblige. Ask ELEO to adjust the training plan due to any real life interruptions , such as travel, sickness, family commitments, etc. You can also give it feedback from real life coaches or recent race results, and ask ELEO to adjust the plan, or just give an opinion. My swimming coach, Hillary, had some strong opinions on frequency of swim practice, and ELEO was happy to oblige. Upload daily screenshots of your workouts (Strava, Garmin, etc.) and your sleep wearable (Oura, Whoop, etc.), and have it adjust your daily workout to optimize adaptation . For example, ELEO caught that my most recent vacation to Santa Fe, New Mexico was building fatigue outside of the training plan (hello, altitude!), and suggested shorter runs and hikes. More recently, she has moved me in the other direction, adding intensity and duration after seeing strong recovery from hard training days, particularly on the bike. Upload daily screenshots of your workouts (Strava, Garmin, etc.) and your sleep wearable (Oura, Whoop, etc.), and have it adjust your daily workout to optimize adaptation . For example, ELEO caught that my most recent vacation to Santa Fe, New Mexico was building fatigue outside of the training plan (hello, altitude!), and suggested shorter runs and hikes. More recently, she has moved me in the other direction, adding intensity and duration after seeing strong recovery from hard training days, particularly on the bike. Ask ELEO a thousand “why” questions . I am worse than a 6-year-old when it comes to asking “why” questions about training. Why that specific heart rate zone for that length of time? Why not longer? What science is that based on? How many sessions like this before we would see a noticeable change? Or is it more reasonable at my age to just hold steady? What would need to happen for me to break 10.5 hours in an Ironman, or is this out of reach? Is that fast enough to qualify for the Kona World Championships at IM Ottawa, based on all recent Ironman results from those in my age group in the last three years? Unlike a human coach, ELEO never gets tired of my questions, and I always get an immediate response, even at 3am. Ask ELEO a thousand “why” questions . I am worse than a 6-year-old when it comes to asking “why” questions about training. Why that specific heart rate zone for that length of time? Why not longer? What science is that based on? How many sessions like this before we would see a noticeable change? Or is it more reasonable at my age to just hold steady? What would need to happen for me to break 10.5 hours in an Ironman, or is this out of reach? Is that fast enough to qualify for the Kona World Championships at IM Ottawa, based on all recent Ironman results from those in my age group in the last three years? Unlike a human coach, ELEO never gets tired of my questions, and I always get an immediate response, even at 3am. Remove the need to ask “how am I doing”? ELEO starts every day with a recap of where we are, what the goals of the day/week/month/phase are, and how my progress is coming. I can just focus on the execution. Remove the need to ask “how am I doing”? ELEO starts every day with a recap of where we are, what the goals of the day/week/month/phase are, and how my progress is coming. I can just focus on the execution. Overall, I’ve been pretty happy with ELEO v1. But there are some issues. Where it breaks is when ELEO sometimes forgets what day it is, what changes we made to the plan and why, or she needs me to cut and paste conversations we have already had back into our chat. These are all memory problems, which is common when you put too much context and content into a single AI prompt. The “cut-and-paste screenshots from Strava and Whoop” process, albeit easy, also does become tedious. It would be much better to have the data imported automatically via an API. For ELEO v2, we primarily look to solve both the memory and the interface problems. Part II - Building ELEO v2 in Claude Cowork When looking to automate the pulling of data via API, there are multiple ways we can do this. The most incremental way is to extend our CustomGPT with “actions”. This would allow us to type in a command that says “refresh Strava”, and it would call the Strava API to get the data from the last 24 hours (once we built the logic). It’s definitely easier than pasting in a screenshot every day, but it is still a manual trigger. I built a few APIs to Strava and Whoop using Zapier as the API glue, and it worked pretty well. But it required coding knowledge, and I still have to type in the command when you want it refreshed. And Zapier doesn’t help with the memory problem. A better solution is to rebuild ELEO as an AI Agent. An AI agent is the next evolution beyond a CustomGPT. It sounds super fancy, but it’s not - you can think of an AI agent as a living prompt on your computer, that can manage files, and is triggered every hour to go look for new information. We can build an AI agent pretty easily, and using all of our existing logic, by installing Claude Code/Cowork . The good news here is that you can use all the work you did with the CustomGPT in Claude Cowork. The bad news is there is slightly more of a learning curve to get started with Claude Cowork, and you will start to get into a few nerdy tasks like “run this command in Terminal”. But I promise you, it is an investment of time that pays off very quickly. You will be stunned at what you can do once you have the basics of Claude Cowork at your fingertips. This is what “getting Claude-pilled” means in the AI circles…it’s very hard to unsee this once you get rolling. 4 To install Claude Cowork, you can follow the instructions on their web site, or just type in “how to install Claude Cowork” into Google for the many YouTube tutorials out there. Once it is installed, Claude will ask you to also install some libraries so that it can write code for you, such as Python, js, etc. Once those are installed, you are ready to create! Before you jump into your main AI coach project, it is best to try a little project first and get the hang of the interface. The Claude team has a great suggestion, which is to ask Claude to organize the downloads folder on your laptop and delete duplicates. Watch it work! Pretty amazing. This displays the other superpower of Claude Cowork - the ability to manipulate, create, and modify files directly on your laptop. This allows Claude to build memory, and always recall where you left off. Now start a “new task” (ELEO v2 in my case), and immediately drop in the exact same instructions you used to create your CustomGPT. Ask Claude to create a skill using this prompt. It will immediately start building files for you, and give you a directory where all the skill files will reside. Most of these files are in a markdown file format (*.md), something you can open in TextEditor to see. You’ll note that Claude is solving the memory problem this way - keeping as much logic and content as possible in these files to remember everything you do together. You can add all of your other files - labs, tests, race schedule, etc. - to these directories just by asking ELEO to put it in the right place. ELEO will suggest adding more files, such as a version change log, which will help. It will also start logging your preferences, and automatically making adjustments to how it reads the training plan and results (for example, how to compare an indoor bike training session to an outdoor one). You’ll stay in this “skill” to do all the ELEO work, but can build other skills for other purposes.

From within this skill, you can ask Claude directly to build API’s for Strava and Whoop. It will instruct you step-by-step on how to set up an API key, test the connection, and make sure it is working. 5 Then you just ask Claude to update the skill to do an hourly refresh, and it will build a service that runs on your computer to check hourly. Guess what…you have an AI agent now! If you run into any problems, you can just ask Claude itself - “why isn’t this working?” and paste in the error, and Claude will suggest solutions, and update the skill for you. There will be some troubleshooting here, and often Claude needs you to run commands for it, but all are just cut-and-paste. You’ll notice that Claude never overwrites or deletes anything without your specific permission. By the time you have this up and running, you should be fully Claude-pilled. Want ELEO to create a web page with your workouts for the week? Done. Want to track advanced metrics like TSS, CTL, and ATL ? Just ask Claude to expand ELEO’s capabilities, and it will update the code, the files, the logs, everything. Want it to slowly build the drawing of a pyramid as you complete your training? Build an app for you? Anything is possible now. What can you do with ELEO v2? How do you get all the coaches in the world to examine your training plan? With ELEO v2 built as an AI agent, it unlocks many new capabilities: Do a hands free check in . Each morning, my previous day workouts (Strava) and sleep analysis (Whoop) have already been uploaded, and ELEO can look at my workouts for the day and adjust as needed. If any new labs or test data is available, she brings in her “doctor” perspective, analyzing overall patterns and trends. For most days, the workout remains as scheduled, and I just get some additional context. I can also ask ELEO questions, such as “my recovery is in the green today, why aren’t we going harder?”, and get a solid, science-based response. Do a hands free check in . Each morning, my previous day workouts (Strava) and sleep analysis (Whoop) have already been uploaded, and ELEO can look at my workouts for the day and adjust as needed. If any new labs or test data is available, she brings in her “doctor” perspective, analyzing overall patterns and trends. For most days, the workout remains as scheduled, and I just get some additional context. I can also ask ELEO questions, such as “my recovery is in the green today, why aren’t we going harder?”, and get a solid, science-based response. Make personalized adjustments to the training plan . Now that ELEO has all the details of my training plan, all my medical records and tests, and a full log of everything we have adjusted and why, she can get very specific on the workout treatments. It blurs the line between coach and medical in ways I haven’t had before. For example, ELEO connected a number of dots in my data - (1) a tendency for my left knee to show signs of “runners knee” on heavy run weeks, (2) metatarsal swelling on my left foot on hot cycling days, and (3) a DEXA scan that showed my left leg is both 1.5 lbs smaller than my right, and about 1 inch shorter. In summary, my left leg is lacking in strength and stability due to a physical abnormality, something that swim/bike/run alone can’t address. With some single leg work, big toe strengthening, and new emphasis on the left side in full body exercises, all of these issues were remedied within a month. ELEO can also get very specific about training for a specific course (hilly, etc.), weather extremes, and accounting for travel. Make personalized adjustments to the training plan . Now that ELEO has all the details of my training plan, all my medical records and tests, and a full log of everything we have adjusted and why, she can get very specific on the workout treatments. It blurs the line between coach and medical in ways I haven’t had before. For example, ELEO connected a number of dots in my data - (1) a tendency for my left knee to show signs of “runners knee” on heavy run weeks, (2) metatarsal swelling on my left foot on hot cycling days, and (3) a DEXA scan that showed my left leg is both 1.5 lbs smaller than my right, and about 1 inch shorter. In summary, my left leg is lacking in strength and stability due to a physical abnormality, something that swim/bike/run alone can’t address. With some single leg work, big toe strengthening, and new emphasis on the left side in full body exercises, all of these issues were remedied within a month. ELEO can also get very specific about training for a specific course (hilly, etc.), weather extremes, and accounting for travel. Have ELEO find other factors affecting the training plan . ELEO is getting quite good at seeing things happening outside of the training plan. For example, she recently detected a consistent 10-15% drop in my resting HRV in the last week. It didn’t line up with the training or past results. One day, she showed me the pattern and asked a bunch of questions about any changes of behavior, or if I was seeing other symptoms. It turns out that a single origin chocolate that I had gotten as a gift (and was nibbling on each night) was really high in caffeine and theobromine, and I had basically been eating the equivalent of two cups of coffee right before bed. Whoops. Another insight - ELEO has shown that the breathing patterns I use in my sensory deprivation training is successful at lowering my heart rate 2-3 beats while running in Zone 1 and 2. I don’t think I have ever read anything about that before. Have ELEO find other factors affecting the training plan . ELEO is getting quite good at seeing things happening outside of the training plan. For example, she recently detected a consistent 10-15% drop in my resting HRV in the last week. It didn’t line up with the training or past results. One day, she showed me the pattern and asked a bunch of questions about any changes of behavior, or if I was seeing other symptoms. It turns out that a single origin chocolate that I had gotten as a gift (and was nibbling on each night) was really high in caffeine and theobromine, and I had basically been eating the equivalent of two cups of coffee right before bed. Whoops. Another insight - ELEO has shown that the breathing patterns I use in my sensory deprivation training is successful at lowering my heart rate 2-3 beats while running in Zone 1 and 2. I don’t think I have ever read anything about that before. Add labs and tests to my calendar . How often should I get my heart rate ranges checked? Should I do blood- or oxygen-based testing? On a treadmill or the bike? When should I do an FTP check for bike power output? ELEO schedules it for me (and can even book the appointment…more on this later), and also watches my daily workouts to determine if enough adaptation has occurred to test again. Add labs and tests to my calendar . How often should I get my heart rate ranges checked? Should I do blood- or oxygen-based testing? On a treadmill or the bike? When should I do an FTP check for bike power output? ELEO schedules it for me (and can even book the appointment…more on this later), and also watches my daily workouts to determine if enough adaptation has occurred to test again. Logically answer the time and money questions . ELEO can now answer the question of “if I have one more hour each week, what should I do?” or “if I have $500 to spend, where should it go?”. 6 It’s not always the answer I want, and it has definitely stopped me from a lot of unneeded purchases. Also, ELEO is a good sounding board for the “should I race next weekend, or should I keep training” question. Logically answer the time and money questions . ELEO can now answer the question of “if I have one more hour each week, what should I do?” or “if I have $500 to spend, where should it go?”. 6 It’s not always the answer I want, and it has definitely stopped me from a lot of unneeded purchases. Also, ELEO is a good sounding board for the “should I race next weekend, or should I keep training” question. Ask the opinion of any coach in the world . One of my favorite uses of ELEO v2 is to have any coach in the world critique my training plan. How would Matt Dixon of Purple Patch view my current training plan, and what might he suggest given I am a masters athlete? Where would the great cycling coach Sir David Brailsford look for marginal gains? How would Ironman legend Mark Allen look at my run plan to ensure I have maximized my endurance capacity? Is The Norwegian Method something I can use at my age, or will I just have a heart attack? I can even ask ELEO to “create a discussion between the following four coaches to critique my training plan, and rank order their suggestions based on common agreement for impact…”. In each case, ELEO runs a simulation 7 , examining my exact training plan, and asks if I would like to incorporate some or all of it. Ask the opinion of any coach in the world . One of my favorite uses of ELEO v2 is to have any coach in the world critique my training plan. How would Matt Dixon of Purple Patch view my current training plan, and what might he suggest given I am a masters athlete? Where would the great cycling coach Sir David Brailsford look for marginal gains? How would Ironman legend Mark Allen look at my run plan to ensure I have maximized my endurance capacity? Is The Norwegian Method something I can use at my age, or will I just have a heart attack? I can even ask ELEO to “create a discussion between the following four coaches to critique my training plan, and rank order their suggestions based on common agreement for impact…”. In each case, ELEO runs a simulation 7 , examining my exact training plan, and asks if I would like to incorporate some or all of it. Does ELEO v2 occasionally have bugs, or misfire in the morning? Well, yes. But it tells me how to fix itself, which is nice. Are my performance results better than a personal coach? It’s hard to say. I am happy with how my training is progressing, and it the best I have seen in the last two years. But in truth, I am likely seeing good personal results because I am sticking to the plan (and getting my labs and tests), as much as the quality of the plan or coaching. ELEO is not a time saver - I am certainly spending more time tweaking the code than I would be in working with a personal coach. But I find it very rewarding to build something cool. Conclusions…and what comes next In the end, ELEO isn’t really a coach. It’s a mirror with a longer memory than I have, and a wider field of view than I can hold. It doesn’t just answer my questions, but reframes the possibilities, and in doing so, quietly replaces my questions with better ones. This may be the real shift AI brings to endurance sport, and everything else: not that we finally have the answers, but that we’re finally asking the right questions. I’m already deeper in the AI rabbit hole, porting ELEOv3 to a full agentic AI system that has many parts working in parallel. Multiple coaches, a doctor, a travel agent, a personal assistant, a music and podcast DJ, an editor, and even a personal therapist. 8 The journey is, once again, proving to be less about the tools, and more about how you frame the problems to solve. It’s a whole new world. The latter taking far more “tokens” to answer, of course. The token is the atomic unit of AI usage, both in terms of what a model uses when you ask it a question (inference), and in how AI companies charge for usage. A token is a small chunk of text (part of a word, a whole word, or punctuation) that AI models process, where longer, more complex, or heavily formatted text uses more tokens, and simpler, concise language uses fewer. So bigger questions that involve more context take more tokens. A recent article from Nick Tiller in Ultrarunning Magazine called “ Should you use AI for your training plan? ”. It is well written, and worth a read. I particularly like all of the examples he gives on how impossible it is for AI to understand all the reality and nuances of running the Western States 100-mile Run. As a 2-time survivor of that race, I can attest he is 100% correct - there is nothing AI can do to prepare you for what happens in the last third of that race, hallucinations being one of the easier issues. But I also see this article as an example of a widespread Dunning-Kruger Effect with AI that is likely occurring due to the sheer simplicity of use of ChatGPT, Gemini, Meta, and Claude. Type in a question, and it is not hard to feel like you have built some base expertise, rather than admit that you are far from having usable AI skills. Only ~16% of the world’s population actively uses AI tools and services, so do know that if you aren’t using AI, you are still by far in the majority. Even if you count all the chatbots, voice assistants, and embedded AI, it’s likely no more than 25% of the globe. But if you said it was 80% of news headlines, I’d believe you. Ironically, the technology that is most likely to make all of our answers and stories more similar, is the perfect fuel for a divisive fear debate. 🙈 The wave of Claude-pilling is so big, Anthropic (the company that created Claude) has grown from 1 billion to 25 billion in revenue in one year. Nearly all of this is software engineers becoming exponentially better within days. 😳 If needed, I can also send you the skill files for the Strava or Whoop API. But I would recommend going through the process of building an API with Claude directly - once you succeed, you’ll see how easy it is to build an API to anything. Need a playlist from Spotify that matches your music tastes, your steps per minute on the run, and is the exact length of your workout? This can be done in 10 minutes. “Get a swim coach” or “get more time with your swim coach” is the most common answer when I ask about how best to spend money. AI agrees that there just is no substitute for in-person coaching, particularly for sports that are technique-driven. When asked what to do with “one more hour”, it usually tells me to trust the process and not feel the need to do more. 🙈 I think it is important to note the word “simulation” here. ELEO never gives me a quote from Matt Dixon, nor does she plagiarize directly from his books. When I ask ELEO for Matt’s opinion, she has to run a simulation. Because of Claude’s training on the text of the Internet, ELEO can summarize and simulate based on the patterns of what Matt has said in public articles and videos, what other coaches say about him, reviews on his coaching practice, and how he cites/critiques/uses other coaching methods. What Claude has is just a string of Matt-like patterns of text (tokens), not really a deep understanding. That being said, the simulated Matt gave two pieces of hard feedback - (1) more strength training based on my age and recent bike results, and (2) identified some days in the training plan that were “mid”, not quite recovery and not quite a workout, and said to just have more purpose here. All great advice that sounds a lot like him. 🤩 I built a personal therapist agent about a month ago, and have been embarrassingly floored by the results. Getting to my “why”, asking hard questions about my role as a parent, a spouse, a leader, what it takes to feel joy, fulfillment, satisfaction, purpose, and where I mix these up. And, oh yeah, calling BS on all the built-in doom loops in my head. 😈 My therapist agent now talks to my coaching agent, and gives me deep topics for long runs and rides. Still undecided if this is a good thing/bad thing. Discussion about this post Fantastic post. I have been playing with Claude to colect data from multiple sources in a dashboard, and started using Claude Code. If you can share your skills files to compare and see where I can learn it would be much appreciated. Scott, another stellar post, thank you! I was waiting for this one. One thing about my chats that absolutely floored me was the "therapist" aspect of it. Some insights gleaned from those "tell me more" questions have been absolutely mindblowing revelations. Dr. AI is scary good at getting inside your head. I'd love to hear more about how you're developing your "therapist". Ready for more?