Episode 850 | How Not to Screw Up When Hiring Your first Developer and More Listener Questions (with Derrick Reimer)

How do you onboard a hire onto a codebase you built alone?

In this episode, Derrick Reimer joins Rob to tackle four listener questions. They cover hiring and onboarding your first developer as a bootstrapped founder, then move into the temptation to build features just because AI makes them cheap to ship, getting past social anxiety as a founder, and whether it's worth trademarking your product name.

Topics we cover:

(3:59) – How do you hire your first developer?

(5:14) – Qualities to look for in a first developer hire

(13:37) – Onboarding a new hire into your codebase with AI

(16:49) – Reducing hiring risk: pairing, reliability, recruiters

(22:50) – The temptation to build features just because AI makes it cheap

(30:43) – Getting over social anxiety as a founder

(35:25) – Is trademarking your product name worth it?

Links from the show:

TinySummit | December 5–7, 2026 · JW Marriott, Cancun