At my first startup, we hacked everything together.

We were racing against time, chasing PMF, and technical debt piled up fast. For a while, it worked - we shipped weekly and closed deals. But 18 months later, the shortcuts caught up.

- New features took weeks instead of days.

- Onboarding new engineers became painful.

- Customers felt the drag in product reliability.

The lesson? Technical debt isn’t inherently bad, it’s a bet.

Sometimes you win that bet: speed gets you to the next milestone, and you can clean up later. Sometimes you lose: the “later” never comes, and the debt compounds.

In my latest Tech Founder Stack post, I share a framework for answering the hardest question engineering teams face: When should you take the shortcut, and when is it time to slow down?

I’d love to hear from other founders & engineering leaders: How do you decide when to prioritize speed vs. sustainability?