Hiring.
The first ten hires decide the next ten years.
Hiring is not recruitment. It is the slow construction of a culture that will outlive any single decision. Every hire changes the room. Some change the company. The work of this chapter is learning to tell the difference before you sign.
Is this person the right cofounder, or just the right friend?
Explore the problem →How do I let someone go with dignity, and still protect the company?
Explore the problem →When and how do I hire my first salesperson?
Explore the problem →When and how do I make my first hire?
Explore the problem →How do I build trust and pace across distance?
Explore the problem →The pieces to read first.
Practical material for doing the work.
Contractor vs Employee: How to Choose Your First Hire Responsibly
Choose a work arrangement based on the real relationship, business need, continuity, and local classification rules—not just headline cost.
How to Hire Your First Operations Employee Without Creating More Work
Hire for a measurable operating bottleneck, define decision rights, and document the system before expecting a new person to make the business run itself.
Remote Work Needs Decision Rules, Not More Meetings
Distributed teams lose time when ambiguity is routed into meetings instead of clear ownership.
How to Structure a First Salesperson's Compensation Without Making the Plan the Strategy
Design first-sales compensation around the learning stage of the company, the sales cycle, quality of revenue and what the salesperson can actually control.
What Should Success for a First Employee Look Like in 30, 60, and 90 Days?
A strong first-employee plan defines outcomes, ownership and learning milestones rather than a long task list.
How to Tell Whether a Performance Problem Is Coaching, Role Mismatch, or Termination
First diagnose whether expectations, capability, role design and support are aligned. The response may be coaching, redesign, reassignment or termination.
What Should Cofounders Agree on Before Splitting Equity?
Agree on roles, decision rights, time commitments, contributions, vesting assumptions, departures and deadlock handling before treating the equity split as settled.
How Remote Teams Keep Pace When Decisions Cannot Wait for a Meeting
Remote trust is easier to maintain when people know who decides, where decisions are recorded, and when escalation is necessary.
How to Hire the First Employee Without Lowering the Bar
The first hire should remove a real bottleneck rather than simply make the company feel bigger.
Do Not Hire Your First Salesperson to Discover Your Sales Process
When and how do I hire my first salesperson?
Firing Someone Kindly Starts Before the Firing Conversation
A humane termination is not a softer version of an unclear decision. It is a clear process that protects dignity, consistency, documentation, and the business.
How Do I Know If This Person Is the Right Cofounder?
Do not choose a cofounder from chemistry alone. Test how you align on ambition, commitment, decisions, conflict, and ownership before you make the relationship permanent.
First Sales Hire: What Must Be Documented Before Delegating Sales
A first sales hire should scale a sales motion you understand, not invent one while carrying a quota.
Do Not Split Equity Until You Have Seen How You Disagree
Cofounder fit is easier to evaluate through real work and hard decisions than through chemistry alone.
When a First Sales Hire Should Be a Learning System, Not a Quota Machine
The first salesperson has to learn the market as well as create pipeline. Hiring before the sales motion is understood can increase cost without transferring the founder’s knowledge.
How to Make a Remote Team Work Without Adding More Meetings
Remote teams often struggle less from distance itself than from unclear ownership, slow decisions, and missing context.
Thinking structures for the decisions ahead.
What other builders actually experienced.
The questions that sharpen the problem.
When Should I Make My First Hire?
A first hire makes sense when the work is persistent, the role is clear, and the business can carry the full cost.
Cofounder Fit: Test the Working Relationship Before Equity
A cofounder is not a friend with a job title. It is a professional relationship that needs the honesty of a friendship and the structure of a contract.
How do I build a remote team that works?
A remote team is not a distributed office. It is a different kind of trust.
How do I fire someone kindly?
Letting someone go is the most honest thing a founder does. The dishonesty is the delay.
When should I hire my first salesperson?
Prove the sale is repeatable, then hire.
Working material you can adapt.
Interview Scorecard
A simple scorecard for evaluating candidates on what matters.
First 90 Days Plan
A working document for turning the first 90 days into evidence, priorities, tests, and decisions.
Role Design Template
A template for writing a role description that attracts the right person.