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Three things he handed off at Site Arrow: → 24/7 support and server admin, to an agency he found on Google → Sales tax compliance, to Paddle as merchant of record → Physical infrastructure, to four cloud providers, so a hosting company owns no servers

Kevin tested the support agency on smaller brands he had acquired rather than his flagship, so if quality slipped the tickets could move back in-house. Most outsourcing decisions are reversible, which is an argument for testing one earlier than feels comfortable.

The outsourcing that failed was development. A contractor with other clients gave him one or two days a week, and an outage once left a provisioning system down for 20 hours because he could not reach the guy. If you outsource engineering, hold your own code and servers.