I see a lot of opportunities. Most are not worth pursuing, and the discipline is in saying no quickly and well. Here is the framework I use, whether the opportunity is an airplane for the club fleet, a business acquisition, or a new brand.
Start with the unit
What is the unit of value, and what does it truly cost? For an aircraft that means fuel, oil, engine and propeller reserves, maintenance, inspections, insurance, hangar, and downtime, all per hour. For a brokerage it means the fully loaded cost of a closed loan. If the unit does not make money with all reserves included, no amount of volume will fix it.
Model the downside first
Every opportunity comes with an optimistic case attached. I build the worst case first: utilization twenty percent lower, a major repair in year one, a rate shock, a key person leaving. If the business survives that, the base and best cases are a bonus.
Price for the risk you can see
Due diligence is where opportunities are won or lost. In an aircraft purchase that means logbook forensics, borescope and compression data, and an independent pre-buy inspection that I control. In a business acquisition it means customer concentration, contracts, and what the seller is not volunteering. The price should reflect what the diligence found, not what the listing claimed.
Weigh the people
I have never regretted walking away from a good deal with the wrong partner, and I have occasionally regretted the reverse. Competence, honesty, and how someone behaves when the numbers go against them matter more than the spreadsheet.
The question nobody asks
Would I personally run this? Not own it, run it. If the answer is no, I either need an operator I trust completely or I need to pass. Capital is easier to find than someone who will care about the business every day.