Interviews with ChatGPT
Ideas (and crazy proposals) that get away from me
TLDR: I’ve adopted a new approach to ChatGPT. “Interview me, one question at a time, until you have everything you need to complete the task.”
Have you ever had an idea that felt brilliant in the moment—only to remember later that you had a great idea, but not the idea itself?
Ideas are fleeting. They slip away if you don’t capture them.
So I’ve built a new habit with ChatGPT. A simple "Interview Me" prompt that keeps my trains of thought running:
I just had an idea. (Brief context in a sentence or two.) Ask me as many questions as you need to fully explore this. The output should be (proposal, table, project plan, etc.).
This does three things:
1. It captures ideas asynchronously.
I can drop a prompt, leave the chat, and come back later—without breaking focus on whatever I’m doing at the moment.
Founder interview? Internal meeting? Mid-workout realization? No problem. The idea is stored, ready to pick up where I left off.
2. It forces deeper thinking.
Instead of giving me answers, ChatGPT asks me questions—forcing me to clarify, refine, and expand my thinking.
Sometimes, the best ideas emerge because of the questions I didn’t initially think to ask. This format turns my thought process into a back-and-forth that’s actually enjoyable, like having a brainstorming partner who never zones out.
3. It delivers ridiculous (and useful) outputs.
Want proof? Here’s an extreme example:
The other day, I randomly thought:
"How do we not know if Bigfoot is real or not?"
So I went to the Interview Me prompt:
"How could we figure out with 100% certainty if Bigfoot exists? Ask me as many questions as you need to make this an investable project."
We went back and forth for 20 minutes on a flight—actually a pretty fun way to pass the time.
It turns out, there are actual ways we could attempt to answer this:
Drones + AI for tracking remote areas
Environmental DNA sampling (eDNA) to detect unknown species
Bioacoustics monitoring for unheard wildlife sounds
Reality TV + Data Licensing to monetize the search
After some discussion, the estimated investment required would be about $33M, and we identified ways to make it profitable through data sales and media rights too.
So, if you’re interested in searching for Bigfoot with me, click here to view the high-level proposal and research:
Of course, while I probably won’t be launching a multi-year Bigfoot expedition, the process was the real win.
The Interview Me Prompt in Action
I now use this approach constantly:
When I see great feedback resonating with a founder
When structuring a Monday Morning Meeting post
When designing a fat loss plan focused on habit stacking
When outlining a vibe coding session at work
When fleshing out big, crazy ideas—like opening a breakfast & après bar in Big Sky
It’s become a thinking tool as much as a writing one.
So next time you have an idea—before it gets away—drop it into ChatGPT. Ask it to interview you. Leave it for later.
You might be surprised by what happens next.
See you Monday.
My guess - "bigfoot" are really just sightings of bears on their hindlegs, from a distance, through the woods. The simplest answer is usually the right one.