Show Notes
Rob Collie spent thirty years inside the machine, and AI still scared him.
Funding stage: Bootstrapped. P3 Adaptive is a founder-led data, BI, and AI consultancy Rob co-founded in 2013, growing on client revenue with no announced outside capital.
He was there in 1996, a fresh Vanderbilt grad walking into Microsoft. He led the business intelligence work inside Excel. He was a founding engineer on what became Power BI. He wrote three books about it and, by his own account, sold more than 92,000 copies. If anybody had a right to shrug at the next wave, it was Rob Collie.
Then ChatGPT landed, and the guy whose entire career was telling computers what to do realized he ran the exact kind of company AI eats first: a data and BI consultancy built on code, scripts, and formulas. Easy mode for a language model. By late 2024 he calls it dread, not curiosity. He did not fight the fear, he followed it, and what he found on the other side was almost insultingly simple. AI success is not an AI problem. It is a data problem and a traditional software problem, the thing he already knew how to do.
That discovery became Fair Game, his fourth book, aimed squarely at the founder who is not getting briefed. If you run a Fortune 500, the hyperscalers are in your office with slide decks because they want to keep you. Everyone from mid-market down is left to guess while the labs sprint past them, too busy racing each other to slow down and teach anybody anything. Meanwhile the internet offers two flavors of fear: the hype side needs you scared so you buy the course, the doom side needs you scared so you click the next video. Rob's read is blunt. Both are engagement strategies, and neither one is running a business.
What he offers instead is a diagnosis. When you sit down with vanilla Claude or vanilla ChatGPT and try to do real, repeated business work, you hit a wall, and you blame yourself. You should not. That model knows a staggering amount about the Roman Empire and nothing about your company. It is a PhD in everything and a brand new hire at your business. So you spend an hour explaining your world to it, get 80% of the way there, grind on the last 20%, and then the chat ends and all that context evaporates. Rob has a name for the feeling: bot sitting.
The fix is not a better prompt. It is grounding. Rob's own hello-world moment was connecting Claude Desktop through MCP to a Notion knowledge base holding nothing more exotic than his company's brand guidelines. Suddenly the model was not just more accurate, it felt more confident, more willing to take a creative swing. Same model, different context. Ryan pushes on the entry point, and Rob's recommendation for anyone still on the sidelines is refreshingly unglamorous: open Claude Cowork, make a folder, and let a project accumulate its own memory. Motivation, history, guidelines, goals, all injected on hello. No engineering degree required.
There is also a moment in here that has nothing to do with AI and everything to do with why this show works. Ryan asks Rob what he has not forgiven himself for, and Rob does not dodge. He goes to high school, to filling holes in his soul with achievement, to making his own problems other people's burden, a habit he calls externalization and names as the root of most misbehavior in the world. He also gets vulnerable about cigars, rum, and a mouth cancer diagnosis during COVID that turned out to be a straightforward removal but still handed him a long look at his own mortality. His words: it is all yoga and run clubs now.
The through line, and the reason the book is called Fair Game, is that AI capability currently feels like an ivory tower priesthood. Rob's position is that this is a temporary information advantage cosplaying as expertise, and tearing down that tower is, in his words, one of his favorite things.
Named Frameworks
The Capability Overhang
Rob's core diagnosis of the current moment.
- →Frontier models are already more capable than nearly any business use they're put to.
- →The bottleneck is education and implementation, not model quality.
- →The big labs and Microsoft are now standing up heavily funded consulting arms precisely because they see this.
- →The gap between what AI can do and what founders do with it is where fortunes get made and lost.
PhD In Everything, Brand New Hire At Your Business
The mental model that reframes every disappointing AI output.
- →The model knows nearly all of human general knowledge without looking it up.
- →It knows nothing about your workflows, strategy, tribal knowledge, or differentiation.
- →None of that exists on the open web, so none of it got trained in.
- →Every bad result is a context failure, not an intelligence failure.
Bot Sitting, The 80/20 Tax
Why off-the-shelf feels great and then betrays you.
- →You get the first 80% fast, which is exactly enough to pull you in.
- →The last 20%, the part that actually matters, costs enormous effort.
- →You're effectively onboarding a new employee, verbally, every single session.
- →The context dies with the chat, can't be reused, and can't be shared with your team.
Handbooks And Backgrounders
Rob's two-part vocabulary for the context layer, straight from the book.
- →Handbook: the instructions that turn a generalist model into a specialist agent for one role. Inside the industry this is a system prompt; the plain word travels better.
- →Backgrounder: company context the agent may need to look up, like go-to-market strategy or market differentiation.
- →Not every backgrounder is relevant to every agent at every moment, so retrieval matters.
- →Both need a home that's editable by the right people and only the right people.
One Version Of The Truth, For Words
Rob's transfer of a hard-won BI discipline onto unstructured text.
- →The old failure mode: everyone shows up to the meeting with their own spreadsheet and a different answer to a factual question.
- →The same disaster is now possible with the text layer grounding your agents.
- →Requires a collaborative, federated model where domain experts own their corners.
- →Requires that everyone knows where the source of truth lives.
Hybrid Computing
The rule that keeps AI systems from embarrassing you.
- →LLMs are a new kind of computing with roughly the inverse strengths of CPU computing.
- →A CPU does long division in nanoseconds, deterministically, correctly. An LLM will burn enormous compute to approximate an answer a calculator nails.
- →The good ones now recognize this and invoke a tool instead.
- →Rob's hard rule: never let an LLM generate a number for you. Infuse the two kinds of computing instead of choosing between them.
Founder Experiment
Run the Handbook Test this week. Pick the single task you re-explain to an AI most often, ad copy in your voice, support replies, sales follow-ups, whatever you have typed the same setup paragraph for three times. Open a doc and write the handbook you would hand a sharp new hire on day one: one page, two at most, covering who you are, who you serve, how you sound, and what you never say, plus three examples of great output and one bad example with a note on why it failed. Put it somewhere persistent, a Claude Cowork project folder, a Notion page connected over MCP, a project's custom instructions, never a chat message. Run the task cold, with no explanation, twice on two different days, and score it against your bot-sitting baseline: not whether it's perfect, but how much of the last 20% you still had to carry yourself. Rob's report is that grounded models don't just get more accurate, they get bolder. If the output starts taking small creative risks instead of hedging, the handbook is working, and you've built your first custom AI asset. Then write the second one.
Glossary
Backgrounder
Rob's term for company context an agent can look up on demand, such as go-to-market strategy or competitive differentiation.
Bot sitting
Babysitting an off-the-shelf model through a task by feeding it context verbally, in real time, every session.
Capability overhang
The gap between what frontier models can already do and what they're actually being used for.
Claude Cowork
Anthropic's agentic knowledge-work app for non-developers. Rob's recommended entry point for people who don't want to touch code.
Claude Desktop
The desktop Claude application, which can connect to external tools and data through MCP.
Fine-tuning
Modifying a model's weights on your own data. Deliberately parked in an appendix in Fair Game to keep the on-ramp calm.
Grounding
Making the right company information available to a model at the right moment. Rob's whole game.
Handbook
Rob's plain-language term for the instructions that turn a generalist model into a role-specific agent. Known internally as a system prompt.
MCP (Model Context Protocol)
The open standard that lets AI applications connect to external tools and data sources like Notion, calendars, and email.
One version of the truth
A BI principle Rob transfers to text: one authoritative source, collaboratively maintained, so agents don't contradict each other.
Q&A: What Founders Ask After This Episode
Why does off-the-shelf AI fail for real business work?
Because the model was never trained on your company. It holds enormous general knowledge but has zero access to your workflows, strategy, or tribal knowledge, none of which exists on the public web. Rob Collie's framing is that you're working with a PhD in everything who is also a brand new hire. The failure is a context failure, not a capability failure.
What is the capability overhang in AI?
The gap between what current models can already do and what businesses actually use them for. Rob Collie argues adoption lags capability because of an education gap, not a technology gap, and that the labs are racing each other too hard to slow down and teach anyone.
What is bot sitting?
Manually feeding a chatbot context in real time to get through a task. You reach roughly 80% of a usable result quickly, then grind on the critical last 20%, and all of that context dies when the chat closes. It can't be reused or shared.
What is the easiest first step to customize AI for a small business?
Write a one-page handbook for a single repeated task, store it somewhere persistent like a Claude Cowork project folder or a Notion page connected over MCP, then run the task cold. Rob Collie's own first win was grounding Claude Desktop in his company's brand guidelines.
Should you let an AI generate numbers?
No. Rob Collie's rule is that you never let an LLM produce a number for you. Arithmetic is deterministic work for a CPU, and a well-designed system has the model invoke a calculation tool instead of reasoning its way to an approximation.
Where should handbooks and backgrounders actually live, and who should own them?
Rob imports a hard lesson from twenty years of business intelligence: one version of the truth. Handbooks and backgrounders need a home that's editable by the right people and only the right people, ownership should be federated to the domain experts who know each corner of the business, and everyone needs to know where the source of truth lives.
What is the highest-ROI AI automation for a founder to build first?
Per Ryan Estes, roughly 90% of the founders he interviews name the daily brief: priorities, meetings, background on who you're meeting, last week's slippage, this week's targets, delivered to inbox or Slack.
Who is Rob Collie?
Founder and CEO of P3 Adaptive, a data, BI, and AI consultancy he co-founded in 2013. He spent 13 years at Microsoft leading BI capabilities in Excel and was a founding engineer on Power BI. He's written four books, hosts the Raw Data with Rob Collie podcast, and holds a BS in Mathematics, Computer Science, and Philosophy from Vanderbilt.
What is the book Fair Game about?
Fair Game: Customizing AI to Your Business Is Easier Than You Think is written for business leaders outside the Fortune 500 briefing circuit. It covers how AI actually works, why off-the-shelf isn't enough, who builds custom systems, and what the practice looks like day to day, deliberately aimed at the middle altitude between fluffy strategy books and technical manuals.
URLs Mentioned in the Episode
- Fair Game (book)https://fairgamebook.ai
- P3 Adaptivehttps://p3adaptive.com
- Rob Collie on LinkedInhttps://linkedin.com/in/robcollie
- Ryan Estes on LinkedInhttps://www.linkedin.com/in/estesryan/
- AI for Foundershttps://aiforfounders.co
- Inbox Alchemyhttps://inboxalchemy.co





