Might be better worded as "The more gambles I've taken, the better I've become at figuring out if my next gamble is going to work. But your mileage may vary."
I keep experiencing the Tim Ferris 4-hour work week idea of the thing that is hardest for you to do at any given time is the thing you need to do the most. Sounds like you have embraced this as well.
Seth Godin talks about it as doing the opposite of what your lizard brain is telling you to do.
Stephen Pressfield calls it the resistance and talks about how you conquer it.
But whatever you call it, I've found that I've made the huge leaps in my professional life when I've conquered the fear (of blogging, public speaking, podcasting, launching apps, etc) and succeeded at something that really scared me.
In my case, I will have customers who are new to email marketing. I don't want to write the equivalent of Drip myself (have code to comply with the CAN-SPAM Act, design campaigns, and so on), so I would have rebranded Drip and integrated it into my product via iframes or links or something. The purpose would be to present my users with a seamless experience and not get them wondering why they're now on someone else's domain.
Another possibility of whitelabeling would be to license the code behind Drip. There'd have to be some due-diligence, to see if their code-base is compatible with mine. And then there'd be the question of merging new versions of the Drip codebase into mine as they make changes (assuming the license gives me access to updates). And what happens if Drip decides to change direction in a way incompatible with how I want to use it.
In any case, I'm still months away from needing something like it, so the question was exploratory.
A whitelabel product is one that you can replace all the branding with your own. [e.g. Amazon's new Route 53 domain registration is really Gandi.net under the hood but it has the AWS branding, not Gandi.net branding]
This reeks of survivorship bias.