The First 10 Employees: How to Hire People Who Will Build Your Empire

Did you know that 23% of startups fail because they don't have the right team? That's more than cash flow problems, more than competition, more than bad timing. Airbnb nearly died in 2009 because they hired the wrong people—their original engineers couldn't scale the platform, and Brian Chesky had to fire them all and start over. Meanwhile, Stripe's first 10 employees became the foundation of a $95 billion company.

Your first hires don't just execute your vision—they shape it, challenge it, and determine whether you become a success story or a cautionary tale. This isn't a guide about posting job listings and crossing your fingers. This is about finding the people who will build your empire with you.

Why Your First 10 Hires Matter More Than Your Business Plan

Here's the uncomfortable truth: your business plan will change. Your market might pivot. Your product will evolve. But your first hires? They become your company's DNA. They establish your culture, set your standards, and determine what's possible.

Look at the data: companies that make strategic first hires grow 3.5x faster than those that hire reactively. When you bring on generalists who can wear multiple hats versus specialists who need everything structured, you buy yourself flexibility. When you hire people who've worked at high-growth companies before, you borrow their playbook.

Consider this: Paul Graham of Y Combinator says the number one reason startups die is "founder problems," but the number two reason is "hiring the wrong people." Wrong early hires don't just slow you down—they actively destroy value. They create politics, lower the bar for future hires, and often need to be fired just when you need everyone rowing in the same direction.

The First 10 Framework: Who You Actually Need

Let's be specific about who your first 10 hires should be. This isn't theoretical—this is based on patterns from companies that made it:

| Hire # | Role | Why Critical | Timing | |--------|------|--------------|--------| | 1-2 | Engineers/Builders | Product doesn't exist without them | Day 1 | | 3 | Designer | Makes product usable and delightful | Month 1-2 | | 4 | Customer Success | Keeps early users from churning | Month 2-3 | | 5 | Sales/Growth | Brings in revenue so you don't die | Month 3-4 | | 6-7 | More Engineers | Scale what works | Month 4-6 | | 8 | Operations | Keeps chaos at bay as you grow | Month 6-8 | | 9 | Marketing | Amplifies what's working | Month 8-10 | | 10 | Specialist (varies) | Deep expertise in your key differentiator | Month 10-12 |

Notice what's missing? Middle management. Fancy titles. People who "supervise" but don't build. Your first 10 should be doers, not delegators.

The Airbnb Example: When Airbnb started hiring beyond the founders, they didn't look for hospitality experts. They hired engineers who believed in the mission. Their third employee, Nick Grandy, was a junior engineer who became CTO. Their first customer service hire, Varsha Rao (now CEO of Kindbody), started by personally responding to every host complaint at 2 AM. These weren't senior executives—they were scrappy builders.

The Stripe Pattern: Stripe's first hires were almost all former founders or early employees at other startups. They knew the chaos. Patrick Collison later said they optimized for "high slope"—people who weren't just good now, but would be exponentially better in 6 months. Their fifth hire, Greg Brockman, became the founding engineer of OpenAI.

The Three Traits That Matter (Forget Everything Else)

After analyzing hiring patterns at 50+ successful startups, three traits predict success in early hires:

1. Intellectual Honesty

Early employees must tell you when you're wrong. They must question assumptions. They must admit mistakes quickly. Intellectual dishonesty kills startups because problems fester until they're fatal.

How to test for it: During interviews, ask about a time they changed their mind about something important. Push back on their answer. See if they defend their position with curiosity or defensiveness. The best candidates will engage, consider your perspective, and maybe even concede points.

2. Bias for Action

You don't have time for people who need perfect conditions to work. You need people who will ship something imperfect at 3 PM rather than plan the perfect thing until 5 PM.

How to test for it: Give them a real problem in the interview. "Our signup flow is broken—users are dropping off at step 3. You have 20 minutes." See what they do. Do they ask clarifying questions and then start sketching solutions? Or do they freeze, wanting more data, more context, more time?

3. Resonance with the Mission

Early-stage companies die when employees treat it like a job. They survive when employees treat it like a calling. You can't fake this—you either care deeply about the problem, or you don't.

How to test for it: Ask why they want to work here. Then ask it again differently. Then have them talk to another team member and see if they mention the mission unprompted. At Stripe, Patrick Collison used to ask: "What would make you quit?" He wanted to hear answers tied to the mission—"If we stopped caring about developers," not "If the office moved too far away."

Where to Find These Unicorns (It's Not LinkedIn)

The best early hires rarely come from job postings. Here's where to actually look:

Your Network's Network: Don't just ask "Do you know anyone?" Ask "Who's the best engineer you know who might be bored at their current job?" Specificity gets results. When Brian Chesky needed engineers, he asked his design school friends who the best coders were—even if those coders had never considered startups.

Side Projects: The best hires are often working on interesting side projects. Look at GitHub, Dribbble, or even Twitter. The person building a weather app for fun on weekends has the skills and the drive you need.

Your Users: Your most passionate users often become your best employees. They already believe in the mission. They understand the product deeply. Airbnb's early customer service team was largely hired from their host community. Notion's first community manager was a power user who had built 50+ templates.

The "Almost Founders": Look for people who tried to start something and it didn't work out. They have founder-level grit but are now looking to join a rocket ship. They're often more valuable than people who've only worked at big companies because they understand the struggle.

The Interview Process That Actually Works

Traditional interviews fail for early-stage hiring. You need something different:

Stage 1: The Coffee Chat (30 minutes) Not an interview. A conversation. You're both evaluating fit. Be transparent about challenges. Share your fears about the company. See if they lean in or pull back.

Stage 2: The Work Sample (2-4 hours) Pay them to solve a real problem. This isn't a "take-home assignment"—it's actual work that needs to get done. Give them access to your product, your data, your team. See how they think, communicate, and execute. Stripe famously had candidates write real documentation.

Stage 3: The Culture Check (Multiple conversations) Have them meet at least three team members. Not just the founders—future peers. You're hiring someone your team will work with daily. Let the team decide. At Superhuman, Rahul Vohra won't hire anyone unless at least two existing team members give a "hell yes."

Stage 4: The Reference Deep Dive Don't just ask for references—choose them. Ask: "Who's the best person you ever worked with? Can I talk to them?" Then ask that person: "Who's the best person you ever worked with?" Keep going. You'll find incredible people this way.

Compensation: What to Pay Your First 10

You're competing against Google and Goldman Sachs for talent. You can't win on salary. So don't try.

The Formula:

• Pay enough that they can survive without stress (usually 70-80% of market rate)
• Give them meaningful equity (0.5% to 3% depending on seniority and timing)
• Sell the learning curve (they'll grow faster here than anywhere else)
• Offer autonomy (they'll own things that would take years to own at a big company)

The Equity Conversation: Be transparent about what the equity might be worth. Don't promise riches, but do the math. "If we hit $10M ARR, this equity is worth $X. If we hit $100M ARR, it's worth $Y." Help them understand the upside.

The Vesting Reality: 4-year vesting with a 1-year cliff is standard, but consider being flexible. Some companies do 3-year vesting. Some do monthly vesting after 6 months instead of a cliff. The goal is alignment, not handcuffs.

Red Flags: When to Walk Away

Even if someone looks perfect on paper, walk away if you see these:

• They need structure: "What's my exact role?" Early-stage means roles change weekly.
• They care about titles: "Will I be VP?" Titles mean nothing when you're 5 people.
• They won't get their hands dirty: "I don't do customer support." Everyone does everything.
• They interview you: "What's your exit strategy?" Wrong question. The right question is "What's our path to product-market fit?"
• They're waiting for more information: Early hires should be comfortable with ambiguity.

Real Case Study: How Notion Hired Their First 10

Notion's hiring story is remarkable because they did almost everything wrong, then fixed it.

The Disaster: Ivan Zhao, Notion's founder, originally hired a team of 15 in 2015. But he didn't have product-market fit yet, and he hired too fast. The product wasn't working, the team was too big, and they burned through cash. In early 2016, Ivan had to lay off everyone except himself and one engineer, Simon Last. They moved to Japan to reduce burn rate and rebuilt from scratch.

The Rebuild: When Notion started hiring again in 2017, they were ruthless about fit. Their third hire was a designer who had built Notion templates as a side project. Their fourth hire was a support specialist who had sent them 20 detailed bug reports. By 2018, they had 10 people. By 2023, they had 600—but those first 10 set the culture that scaled.

Lessons:

• Hire slow until you have product-market fit
• Hire people who already love the product
• One great hire is worth five good hires
• Culture compounds—get the first 10 right

Real Case Study: How Figma's First Hires Shaped a $20B Company

Dylan Field started Figma in 2012 with the audacious goal of building design tools in the browser. His first hires determined whether this was possible.

Hire #1: Evan Wallace (CTO) Evan was a friend from Brown University who had worked at Microsoft. He joined because he believed browser-based design was inevitable. Eight years later, he was still there, having built the rendering engine that made Figma possible.

Hire #3: Sho Kuwamoto (Product) Sho had been at Adobe and Microsoft. He brought enterprise software expertise to a startup building for designers. He questioned Dylan constantly—and that friction made the product better.

The Pattern: Figma's first 10 hires included three former founders, two designers who became product managers, and zero "big company executives." They optimized for learning velocity over credentials.

Action Steps: What to Do This Week

Monday: List the three most critical things your company needs to accomplish in the next 90 days. These determine who you hire next.

Tuesday: Reach out to 10 people in your network. Not to ask for candidates—to describe your challenges vividly. The right people will self-identify.

Wednesday: Create a "work sample" assignment for your next hire. Make it something you actually need done.

Thursday: Review your interview process. Are you testing for intellectual honesty, bias for action, and mission resonance? If not, redesign it.

Friday: Have honest conversations with your current team about what excellence looks like. Define your culture before you dilute it.

Conclusion: Your First 10 Become Your Foundation

The companies that become great don't stumble into great teams—they build them intentionally. Your first 10 hires will work harder, care more, and shape your culture more than anyone who comes after. Treat this with the seriousness it deserves.

Your Next Step: Schedule three coffee chats this week with people who might be your next hire. Don't post a job description. Don't write a requirements list. Just talk about what you're building and why it matters. The right people will lean in. And when they do, you'll know—you've found someone who can help you build an empire.

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Meta Description: Learn how to hire your first 10 employees using the same framework as Airbnb, Stripe, and Notion. Get specific tactics, compensation formulas, and interview processes that actually work.