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

Hosted byRob Walling

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
• MicroConf US | April 18–20, 2027 · Austin, TX
• Partnerships: sponsors@microconf.com
• Idea to Traction: Stop Building SaaS Nobody Wants (book wait list)
• Rob Walling Newsletter
• Remote First Recruiting
• SavvyCal
• Derrick Reimer | LinkedIn

If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you!

Subscribe & Review: iTunes | Spotify