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Yes, you're right that if you opt for pseudonym, you have to start from scratch.
If you already have substantial amont of engagement with your clients in public, I would suggest you to continue this in part and also start with anonymous service provider. When you reach at a level where your service as anonymous become popular slowly shard your public image and be private forever.
This is the best way to opt in for annonymity.
There are also other ways to bring in your public image or money to annonymity. Consider making regular p2p transactions and bring your money to Bitcoin. Try creating an annonymous circle with clients you know publicly. Give them those offers which they won't get publicly. I mean market your annonymous services first, and when you're popular enough under a pseudonym, leave that public image.
The anonymous circle idea is an interesting one.
Your overall idea seems feasible, and this is also coming at a time when I'm shifting gears on what sort of services I provide. This seems like the perfect time to start fresh with some of these new ideas.
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