Keep Thinking
Back to Guides
Team14 min read

Hiring Your First Employees

How to attract, evaluate, and hire your founding team members.

Keep Thinking Team

1When to Hire

Hire when you're drowning, not when you're comfortable. Early hires are expensive in equity and attention.

Before hiring, ask: Can this be automated? Can this be outsourced? Can a founder do this for 3 more months?

The right time to hire is when not hiring is clearly costing you more than hiring would.

2Who to Hire First

Hire for your gaps. If you're technical, hire someone who can sell. If you're a salesperson, hire someone who can build.

Early employees need to be generalists who thrive in chaos. Specialists come later.

Culture fit matters more at this stage than at any other. One bad hire can poison your entire culture.

Pro Tips
  • First hires should be doers, not managers
  • Look for people who've done more with less before
  • Prioritize learning speed over current skills

3Where to Find Talent

Your network is your best source. First-degree connections and referrals convert at 10x the rate of job boards.

Be everywhere your potential hires are: Twitter, Discord communities, meetups, conferences.

Great talent often isn't looking. The best hires often come from someone you reach out to directly.

4The Interview Process

Interviews are terrible predictors of job performance. Supplement with work trials when possible.

Look for: intelligence, energy, and integrity. You can't train these.

Check references thoroughly. Ask: 'Would you hire them again?' The hesitation tells you everything.

Pro Tips
  • Use structured interviews—same questions for all candidates
  • Involve your team in interviews to check culture fit
  • Pay attention to how they treat everyone, not just decision-makers

5Compensation & Equity

Early employees trade salary for equity and upside. Be clear about what they're getting into.

Use standard vesting: 4 years with a 1-year cliff. This protects both sides.

Be transparent about your cap table and what their equity could be worth in different scenarios.

Key Takeaways

1Hire when it hurts, not when it's comfortable
2First hires must be generalists who thrive in ambiguity
3Your network is your best recruiting tool
4Work trials predict performance better than interviews
5Be transparent about compensation, equity, and what you're building

Put This Into Practice

Ready to apply what you've learned? Get your startup validated by experts.

Submit Your Startup