Careful Consideration and Analysis
Most organizations view business development opportunities as a threat.
A threat because a mistake could upset the status quo, could cost money or time, or even get someone in trouble.
After an initial screening, the typical bizdev proposal is given Careful Consideration and Analysis. Which means that lawyers work hard to make sure (among a hundred other things) that the trademark licensing deal is accurate and appropriate (SM instead of TM, please) and that they’ve done their job and that nothing bad can happen.
The problem, as you’ve already guessed, is that fashion is unpredictable. So, if the very point of the bizdev deal is to engage in a search for a hit, to do something new and inexpensive that may or may not work, then Careful Consideration and Analysis is probably completely inappropriate. Careful Consideration and Analysis leads to high overhead, slow turnaround and plenty of "no".
The alternative might be, What’s the Worst That Could Happen? Look at a deal. Decide if there’s enough upside possibility. Do the What’s the Worst That Could Happen test. Figure out how to avoid the most egregious outcomes. Then do it.
Repeat.
My guess is that Starbucks’ digital music efforts didn’t pass the Careful Consideration and Analysis test. But they did it anyway. And it failed. No big deal. Why? Because What’s the Worst That Could Happen was pretty low.