Hiring Your First Person

First hire is high stakes. They see your workflows at their messiest, they double your people-cost, and they shape your culture from day one. Most first hires should be contractors, not employees, for both flexibility and tax simplicity. Most first hires should be for the work you're worst at, not the work you're best at.

Before you write a job listing, answer: what specifically would I spend 20 hours a week on if I weren't doing the thing I hire them to do? If you can't answer, you're not ready to hire. Hiring is buying back your hours — only worth it if you know exactly what you'd do with those hours.

Contractor vs. employee — almost always start with contractor

The job scope brief, written first

Before posting anywhere, write this:

Role: [title]
Type: [1099 contractor / part-time / full-time]
Hours: [X/week]
Rate / pay: [range]
Start: [when]
Location: [remote / timezone]

What they'll do, concretely (bulleted, 5-8 items):
- [each item is a specific ongoing task or goal]

How success is measured (first 30 days):
- [numeric or delivery-based]

Skills they must have:
- [2-4, specific]

Skills nice to have:
- [2-3, flexible]

What this role is NOT:
- [2-3 things — prevents scope creep in interviews]

If you can't fill this in cleanly, don't hire yet — you don't know what you want.

Where to find first hires

• Your existing community (Twitter, Discord, customer base) — highest signal
• Contra / MetroJobs / We Work Remotely for global remote contractors
• Upwork / Contra for task-based work
• Specific communities (Indie Hackers, maker Discords) for founder-adjacent roles
• Referrals from other founders — ask 3 people in your network

The working trial — before the hire

Before you commit to an ongoing hire, do a paid 4-10 hour test project. Pay fairly. Give them a real problem. Watch how they communicate, meet deadlines, respond to feedback. This $200-$500 invested saves you months of misfit. Any candidate unwilling to do a paid trial is a pass — good people welcome a chance to show their work.

The 30-day onboarding

1. 1Day 0: access to tools, brand voice prompt, intro doc with mission + wins + losses
2. 2Day 1-7: shadow you, pair on 1-2 real tasks, ask questions freely
3. 3Day 8-14: ownership of 1-2 recurring tasks with weekly checkin
4. 4Day 15-30: full ownership, measurable metric, async communication
5. 5Day 30: honest review — keep, adjust scope, or part ways

Teen-founder specifics

Hiring adults when you're 16 feels weird. The move: hire on results, not rapport. Let them do a paid trial. Be absolutely professional in writing. Pay on time, always. Competent people care less about your age than about your reliability. But if you're under 18, have a parent co-sign contractor agreements to avoid the 'minor can't contract' issue.

What 'good' looks like

A good first hire: carefully scoped role, paid trial done, clear 30-day metrics, onboarded into your tools and voice, delivering measurable value by day 30, and contracted cleanly through a real 1099 agreement. You've bought back 20+ hours a week. You spend those hours on sales or product, not more ops. That's leverage.