We can ship the first version in two weeks on a managed service, or in six weeks on our own infrastructure. Which do we pick?

Option A is the stronger choice because the first version's biggest uncertainty is whether users want the product and what they actually need, and shipping in two weeks buys real-world learning four weeks earlier. That faster feedback loop reduces opportunity cost, avoids over-investing in infrastructure before demand or product-market fit is proven, and prevents building a system around assumptions that may change. The later migration is a known, bounded cost that can be planned and informed by actual usage data; it only becomes relevant if the product succeeds, and by then the team will know the real scale and feature needs, making the eventual own-infrastructure build better targeted. Option B's case for avoiding migration and keeping cost and data control from day one is valid in principle, especially if there is a hard compliance, regulatory, or data-sovereignty requirement, but no such constraint is stated. Absent that, early infrastructure ownership often means over-provisioning, diverted engineering time, and weaker cost control, while the certain benefit of earlier feedback is deferred to avoid a contingent, manageable cost. Waiting six weeks risks missing a market window and building the wrong features—a more severe failure mode than a schedulable migration. So ship on the managed service now, learn from real users, and migrate later with usage data.