Every time I've skipped one of these questions, it cost me money. Not "learning experience" money. Real money. So now I ask all five, every time, even when I'm excited about an idea and don't want to hear the answers.
1. Is anybody already paying for this?
I don't invent categories. I've watched too many smart people burn years trying to convince the world it has a problem. If people are already searching for something, already buying it, already filling out forms to get it, that demand is real and I can measure it. If they're not, no amount of clever marketing changes that.
This sounds obvious. It's the question people skip the most, because the honest answer kills exciting ideas.
2. Am I the customer?
The best businesses I've started came out of my own frustration. I needed a tool, went shopping for it, and everything out there was either wrong for the job or priced like a hostage negotiation. That frustration is information. If my own companies need something badly enough that I'd build it just for us, there are other operators out there stuck in the same spot.
When I'm not the customer, I'm guessing. I can still do it, but I know I'm guessing, and I size the bet accordingly.
3. Can it run without me standing in the room?
I learned this one the expensive way, running six physical call centers. A business that only works when you're personally there isn't a business. It's a job with extra liability. So before I start something now, I ask what it looks like at month eighteen. Who's running it day to day? Is the answer a system, or is the answer me?
If the answer is me, I either redesign it or I don't do it.
A business that only works when you're personally there isn't a business. It's a job with extra liability.
4. Do I want to own this or rent it?
For years I licensed whatever software my businesses needed and worked around the limits somebody else set. At some point the math flips. If a tool is load-bearing, if the business falls over without it, I'd rather own it than send someone a check forever and hope they don't change the rules. That one decision turned me from a software customer into a software company.
Not everything is worth owning. Plenty of things I happily rent. But I make it a decision instead of a default.
5. What happens if it works?
This is the question people never ask, because it feels like counting chickens. But it matters. Does this thing feed the rest of what I do, or is it a stray? The businesses that have paid me best are the ones that made my other businesses stronger. Lead generation feeds the software. The software makes the lead business run better. Winning in one place should make the next win cheaper.
A one-off can still be a fine business. It's just a harder way to live.
That's the whole system
No spreadsheet, no framework with a trademarked name. Five questions and the discipline to actually listen to the answers, especially when I don't like them. It's carried me since 1996, and it's the closest thing to a secret I've got.
If you want to see what came out of asking them a hundred-some times, the portfolio is at joedelfgauw.com.
Next read I Don't Sell Software I Don't Run