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I'm attempting to become an anchor.

Reading through https://www.stellar.org/developers/guides/anchor/ it goes into detail for anchors that use federation and memo fields but is thin on detail for maintaining a stellar account for each customer. Which is the approach I would like to take.

Do I always need to run a bridge and federation server regardless of approach?

It seems like I need at least a bridge server to provide a home for stellar.toml

I'm technically savvy, just learning the stellar ropes. Could anyone point me to some docs resources or kindly souls that could help me get up and running?

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The approach I take on https://debtmoney.xyz/ is basically to keep a list of users in the database, along with their addresses and seed keys.

The keys are created whenever the user signs up and prefunded whenever the user attempts to use his account for the first time, then the keys are stored as plaintext on Postgres.

The code for the entire app is on https://github.com/fiatjaf/debtmoney.xyz. It's very small.

Federation is not necessary for this approach to work (but you can easily hook-up a federation endpoint in your HTTP server and write a stellar.toml that points to it). Actually, federation is just that, an HTTP endpoint that turns addresses into usernames and vice-versa.

If you, unlike me, are expecting people to store lots of value in the accounts they keep within your platform, then you probably should store the seed keys in a more secure setup than mine.

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