The inverse is the same.

Losing $1mil can either mean: a) losing 10000 customers b) losing 1 customer. What do you pick?

There are more customers who can afford 100$ than 1mil. That's the important factor, not the way you want to present the numbers.

Not really. Small customers are sensitive to fads and trends, while enterprise customers (particularly in the field of software, as we all know!) will stick with a product well past its sell-by date as long as it "works." You have a lot more time to pivot when you start losing enterprise customers than small customers.

I think he meant with inverse. a) winning 10000 customers b) winning 1 customer.