TSUW - Your First ‘Not-You’: How to Hire the First Employees Without Breaking the Startup

Hello again, people-building founder. Welcome back to The Startup Wagon, where today’s issue tackles one of the most emotional and high-impact moments in a startup’s life: hiring your first employees. The first few hires don’t just help with workload—they shape culture, execution, and momentum in ways that last far longer than most founders expect.

Early hiring decisions are leverage points. Get them right, and everything accelerates. Get them wrong, and progress slows while stress skyrockets. The goal isn’t to build a big team—it’s to build the right one.

1. Hire to Solve Real Bottlenecks, Not Hypothetical Ones

The biggest mistake founders make is hiring based on what they think they’ll need later.

Strong founders hire when:

• A task consistently pulls them away from high-impact work

• A skill gap is blocking progress

• Growth is limited by capacity, not ideas

Your first hires should remove friction from the business today, not support plans that may change tomorrow.

2. Prioritize Range Over Specialization

Early employees must be comfortable wearing many hats.

Strong early hires typically:

• Learn quickly

• Take ownership without direction

• Operate well with ambiguity

• Care about outcomes, not titles

• Jump between tasks as needed

Deep specialists shine later. Early on, flexibility and problem-solving matter more than narrow expertise.

3. Look for Ownership Mentality, Not Just Talent

Skills matter—but mindset matters more.

Great early employees:

• Treat the company like it’s theirs

• Spot problems without being asked

• Care about customers

• Follow through consistently

• Hold themselves accountable

Ownership mindset is hard to teach and easy to spot if you ask the right questions.

4. Hire Slower Than You Want To

Pressure to hire quickly is real—but rushed hires are expensive.

Smart founders:

• Test candidates with real work

• Use trial projects or contract periods

• Involve co-founders in decisions

• Check references thoroughly

It’s better to wait than to hire someone who isn’t a strong fit for the stage.

5. Compensation Is More Than Salary

Early employees take risk, and compensation should reflect that.

Typical early packages include:

• Market-adjusted salary (not top of market)

• Equity aligned with impact

• Clear expectations

• Growth opportunities

Transparency matters. When people understand both the upside and the risk, trust grows.

6. Culture Is Set by the First Few Hires

Your first employees define how work gets done.

They influence:

• Communication style

• Decision-making

• Work ethic

• Conflict resolution

• Company values in action

Founders don’t “own” culture alone. The first hires amplify it—for better or worse.

7. Onboard With Intention

Early onboarding sets the tone for everything that follows.

Strong onboarding includes:

• Clear goals for the first 30, 60, and 90 days

• Context around why things exist

• Access to customers and product usage

• Frequent feedback

Early employees should feel empowered quickly, not left guessing.

8. Be Ready to Let Go

Not every hire works out—and that’s okay.

Founders must be willing to:

• Address issues early

• Give clear feedback

• Make tough calls when fit isn’t there

Delaying a necessary separation hurts morale, execution, and trust.

9. Hire for the Company You’re Becoming—Not the One You Were

The goal isn’t to recreate the founder.

Great first hires complement your strengths and challenge your blind spots. Diversity of thinking early on builds stronger foundations.

Final Takeaway

Hiring your first employees is one of the most important investments you’ll make. These hires shape how your startup works long before systems and policies exist. When founders hire intentionally, communicate clearly, and protect culture early, growth becomes smoother and far more sustainable.

Your first employees don’t just help build the product. They help build the company.

That’s All For Today

I hope you enjoyed today’s issue of The Wealth Wagon. If you have any questions regarding today’s issue or future issues feel free to reply to this email and we will get back to you as soon as possible. Come back tomorrow for another great post. I hope to see you. 🤙

— Ryan Rincon, CEO and Founder at The Wealth Wagon Inc.

Disclaimer: This newsletter is for informational and educational purposes only and reflects the opinions of its editors and contributors. The content provided, including but not limited to real estate tips, stock market insights, business marketing strategies, and startup advice, is shared for general guidance and does not constitute financial, investment, real estate, legal, or business advice. We do not guarantee the accuracy, completeness, or reliability of any information provided. Past performance is not indicative of future results. All investment, real estate, and business decisions involve inherent risks, and readers are encouraged to perform their own due diligence and consult with qualified professionals before taking any action. This newsletter does not establish a fiduciary, advisory, or professional relationship between the publishers and readers.