Handbook
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Hiring & Team
Making Your First Hires
Your first hires shape everything. Here's how to think about who to hire first and how to find them.
First hires are the highest-stakes hiring decisions you’ll make. These people don’t just do work—they set the culture, establish standards, and hire everyone who comes after. Getting your first few hires right compounds. Getting them wrong creates problems that persist.
Why First Hires Matter So Much
They Define Culture
Culture comes from people:
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First employees establish norms
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Their behavior becomes “how we do things”
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They hire people like themselves
Choose carefully: You’re not just hiring skills. You’re choosing who shapes the company.
They Attract (or Repel) Future Hires
Great early people:
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Know other great people
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Attract quality candidates
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Raise the bar for everyone
Mediocre early people:
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Lower standards
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Drive away good candidates
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Create hiring debt
They Take Responsibility Off Founders
Early hires must be capable of:
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Working independently
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Making decisions
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Owning outcomes
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Not needing management
You can’t babysit your first hires.
When to Make First Hires
Not Before You Need To
Premature hiring is expensive:
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Burns cash
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Creates management overhead
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Dilutes equity
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Sometimes hides product problems
Ask first: Can founders do this work? Can it be contracted?
After You’ve Found Product-Market Fit (Usually)
Ideal timing:
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You’ve validated demand
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You know what to build
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Growth is outpacing capacity
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You need specific skills
Hiring before PMF is risky.
Hiring Triggers
Good reasons:
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Critical skill gap founders can’t fill
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Team is burning out
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Clear work that needs doing
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Growth requires it
Bad reasons:
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“We raised money”
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Vague sense of needing help
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Someone good is available
Who to Hire First
The Generalist Profile
Early hires need to be generalists:
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Comfortable with ambiguity
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Can do multiple things
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Adaptable as needs change
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Don’t need structure
Specialists come later.
The Startup Profile
Not everyone thrives in early-stage:
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Need self-starters
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Need problem-solvers
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Need people who build
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Need low-ego collaborators
Big company experience can be negative signal.
Common First Hire Patterns
Technical co-founder first:
If founding team lacks technical skills, this is often the first hire. Consider making them co-founder.
First engineer:
Building the product, shipping features.
First marketer/growth:
Once product exists, someone to get users.
First salesperson:
For B2B, someone to close deals.
First ops/admin:
Takes operational load off founders.
The “Do Everything” Role
Sometimes you need someone who just helps:
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Chief of Staff
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Operations generalist
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“Whatever needs doing”
This can be incredibly valuable early.
What to Look For
Track Record of Building
Ask:
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What have they built?
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What was their specific contribution?
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What happened to it?
Look for evidence of shipping things.
Independence
Indicators:
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Started things on their own
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Solved problems without being told
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Took initiative
You can’t manage first hires closely.
Missionary, Not Mercenary
Missionaries:
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Believe in the mission
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Motivated by the problem
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In it for the right reasons
Mercenaries:
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Motivated by money/title
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Less committed when hard
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Will leave for better offers
You want missionaries.
Culture Add
Don’t just hire for culture fit:
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What do they add to the team?
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What perspective do they bring?
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What gaps do they fill?
Comfortable With Chaos
Early startup life is chaotic:
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Plans change
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Priorities shift
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Nothing is established
Some people thrive in this. Most don’t.
Where to Find First Hires
Your Network
Best source by far:
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People you’ve worked with
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People your co-founders know
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Friends of friends
Trust is established. Quality is known.
Second-Degree Network
Ask your network:
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“Who’s the best [role] you’ve worked with?”
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“Who do you know who might be interested?”
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LinkedIn connections in common
Referrals are higher quality.
Communities
Where relevant people gather:
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Industry Slack groups
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Online communities
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Meetups and events
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Open source projects
Engagement before recruiting.
Direct Outreach
For specific people:
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LinkedIn messages
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Email if you can find it
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Warm intro if possible
Personalization matters.
What Doesn’t Work Well
For early hires:
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Job boards (too many unqualified)
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Recruiters (expensive, don’t understand early-stage)
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Generic postings (attract the wrong people)
Network-driven hiring is better for first hires.
Selling to First Hires
What You’re Asking
Early employees take enormous risk:
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Salary often below market
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Equity value uncertain
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Company might fail
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Lots of hard work
You’re asking them to bet on you.
What You’re Offering
The pitch:
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Mission and vision
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Equity upside
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Impact and ownership
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Growth opportunity
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Working with great people
Be honest about what it is.
Be Authentic
Don’t oversell:
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Be honest about the stage
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Share the risks
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Explain the trade-offs
People who join with eyes open are more committed.
The Founder Brand
Your reputation matters:
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Have you worked with them before?
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What do people say about you?
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Do you have credibility in the space?
Build reputation before you need to hire.
Evaluating First Hires
Weight Culture Heavily
For first hires, culture matters more than skills:
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Skills can be developed
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Culture is who they are
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They’ll define culture for everyone else
Look for Evidence, Not Potential
Don’t bet on potential alone:
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What have they actually done?
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What’s their track record?
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Have they shipped things?
At early stage, you need people who’ve proven they can do it.
Move Fast
Don’t over-process:
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Short interview cycles
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Quick decisions
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You need them now
But don’t compromise on quality.
References Matter More
Check references carefully:
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They’re betting on you
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You’re betting on them
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Get real information
Talk to people who’ve worked with them.
Structuring Compensation
Cash vs. Equity
Early hires typically take:
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Below-market salary (somewhat)
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Significant equity
Equity ranges for first employees:
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Employee 1-3: 1-2% each
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Employee 4-10: 0.5-1% each
These are rough guides.
Making It Work
Some candidates have financial needs:
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Be flexible where you can
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Signing bonus might help
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Understand their situation
Equity Matters
Early employees should understand:
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What they’re getting
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Why it matters
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What success looks like
Educate them on the value.
Common First Hire Mistakes
Hiring Friends
Friends aren’t always the right fit:
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Hard to give honest feedback
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Hard to fire if needed
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Relationship clouds judgment
Evaluate friends as rigorously as strangers.
Hiring for Now, Not Growth
Someone great for seed stage might not scale:
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Can they grow with the company?
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Are they learning fast?
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Do they have headroom?
Over-Hiring
Hiring multiple people before you need them:
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Burns cash
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Creates coordination overhead
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May hire wrong people before understanding needs
Hire one, learn, then hire next.
Compromise Hiring
Taking someone who’s “good enough”:
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The cost of wrong hires is high
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Better to wait than settle
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“Hell yes” or no
Not Selling
Assuming good people will just join:
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Everyone is selling you
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You need to sell them
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The founder pitch matters
Key Takeaways
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First hires define culture, attract future talent, and shape the company—highest stakes hiring
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Hire generalists who can work independently, handle ambiguity, and build
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Network is the best source: people you’ve worked with, referrals, trusted connections
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Look for evidence of building things, not just potential—track record matters
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You’re asking them to bet on you; sell the mission, equity upside, and impact
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Be honest about risks—people who join with eyes open are more committed
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For first hires, weight culture heavily—skills can develop, culture is who they are
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Don’t hire friends without rigorous evaluation; don’t compromise on quality
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Move fast but don’t over-hire—one at a time, learn, then hire next
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Check references carefully—you’re making a big bet on each other
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