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In 1996-2003: running a payment service provider for dot-coms who wanted to actually do B2C sales on the internet. Rewind to 1996 and Paypal and similar didn't
by cstross 8y ago
In 1996-2003: running a payment service provider for dot-coms who wanted to actually do B2C sales on the internet. Rewind to 1996 and Paypal and similar didn't exist, getting permission to do cardholder-not-present transactions was a black art, and most companies used EPOS terminals talking to Visa/Mastercard or a local franchisee (depends on the country) via modem over POTS, with about 10-30 second latency to make an authorisation check (and only one auth check per phone call).
In 2019: look for something that disintermediates supply and demand (or, much rarer and harder, something wholly new that nobody can supply yet and which has vast potential demand).