Technical Lessons from Startup CTO Life

Being a startup CTO taught me more about engineering than any other role. Not because the problems were harder, but because every decision had immediate, visible consequences.

Ship First, Optimize Later

Premature optimization isn't just about code. It's about architecture, tooling, processes.

We spent two weeks building a "scalable" message queue system before we had paying customers. We should have used a managed service and moved on.

Rule: If you're not embarrassed by your first version, you shipped too late.

Choose Boring Technology

Every new technology is a liability:

• Learning curve for the team
• Unknown failure modes
• Smaller talent pool
• Less documentation

PostgreSQL, Redis, and proven frameworks get you far. Save the experiments for problems that actually require them.

Debt is Real

Technical debt compounds. That "temporary" hack becomes permanent. That missing test becomes a production incident.

Budget time for cleanup. Not as a separate project—as part of every sprint.

Documentation Matters

"The code is self-documenting" is a lie we tell ourselves. Write:

• Architecture decisions (ADRs)
• API contracts
• Runbooks for common issues
• Onboarding guides

Future you (and your team) will be grateful.

Hire for Adaptability

In a startup, roles blur. The best engineers I worked with could:

• Debug production issues at 2am
• Write user-facing copy
• Talk to customers
• Question product decisions

Technical skill matters, but flexibility matters more.

Conclusion

Startups are chaos. Your job as a technical leader is to build systems—both technical and human—that can handle that chaos without breaking.