A very interesting thread.

My tuppence worth

One day workshop, four themes, 2 hours per theme, in each using bicycling as a metaphor for commercial decisions involving risk

1 Calculation. R+ and R-, risk and reward, making a decision to operate only in the zone of potential gain. Don't do anything you can't do. Don't ride bikes unlit in Manhattan, don't do a ride in Arizona summer without planned water stops, understand your present strength and fitness, don't borrow at 8% to open 5% roi businesses. Do the sums, honestly and accurately.

2 Anticipation. Understand traffic patterns on your route, don't ride on the school run or commuter traffic, don't ride (here in August in Bahrain) after 8.00 am, don't ride at sundown into the sun when traffic from behind will be dazzled by low sun in front. The Motorcycle Safety Foundation advises "Think 6 seconds ahead - and think six seconds ahead for everyone you can see, who aren't thinking 6 seconds ahead". Avoid routes (or commercial ventures) where the biggest risks (semi trucks, cash rich competitors) might prowl.

These two themes are about "Is it worth it". The next two are about "How to do it".

3 Mitigation. Tool kit and the ability to use it? Water stops, food stops, power bars, cell phones, loved ones warned and agreeing to be a sag wagon? Planned "quit" decision points? Go/no go points within the commercial project plan? Sponsor agreement to each of these "Continue/Quit" milestones?

4 Preparation. Have you gained the required levels of skill, commitment and fitness? Have your companions (staff)? Are you planning something that your necessary collaborators (staff, financial backers, technical and financial collaborators) consider daft? Does your sag wagon driver have a liking for a frothy one after 5.00 pm, when you're going to be out after 8.00? Have you done this before? Have you benchmarked the skills and endurance required against others who have?

Hey, sorry but I got interested!