The First Hire: Why It’s a Gamble, Not a Guarantee

November 19, 2025

The First Hire: Why It’s a Gamble, Not a Guarantee

People often celebrate hiring their first employee as a major milestone in the entrepreneurial journey. It’s seen as a sign that your business is growing, that you’re “making it.” But as Jeremy Axel and Douglas Cox reveal in episode 39 of the "Never in Reverse" podcast, this moment is far more complex, and risky than most founders realize. The first hire is not a guaranteed win; it’s a strategic gamble that can either accelerate your business or set you back significantly.

In this comprehensive guide, we’ll break down the nuanced realities of making your first hire, drawing on the candid insights and hard-earned lessons shared by Jeremy Axel and Douglas Cox . We’ll explore the emotional and operational challenges, the importance of structure and clarity, and actionable strategies to help you navigate this pivotal decision with confidence.

The Myth of the First Hire as a Milestone

Douglas Cox opens the episode with a reality check: “Everyone dreams about that first hire, the moment when your business starts to grow. But what no one really tells you is that this milestone is actually a gamble. That first employee can either make or break your business.”

Key Insight:

The first hire is not a finish line; it’s the start of a new, riskier phase. The wrong hire can drain resources, damage morale, and even threaten the survival of your business.

Tip 1: Set Clear Expectations—What You Permit, You Promote

Why It Matters:

Without clear expectations, you create ambiguity. Employees will fill in the blanks themselves, often in ways that don’t align with your vision.

Actionable Steps:

Document Everything:
Write detailed job descriptions, including responsibilities, performance metrics, and reporting lines.
Define what success looks like in the role, both short-term and long-term.
Communicate Early and Often:
Don’t assume your new hire “gets it.” Spell out your expectations in onboarding and reinforce them regularly.
Use checklists, SOPs, and regular meetings to keep everyone aligned.
Enforce Consistently:
As Doug says, “What you permit, you promote.” If you let one person slide, others will notice, and standards will erode.
Set consequences for missed expectations and follow through.

Expert Advice:

“Without accountability, people just show up and go through the motions, which doesn’t get you anywhere.” — Douglas Cox

Tip 2: Don’t Hire Too Early—Preparation Is Everything

Why It Matters:

Hiring before you’re ready can be a costly mistake, financially and emotionally.

Actionable Steps:

Assess Your Readiness:
Do you have clear processes, documentation, and onboarding materials?
Are you prepared to lead, train, and support someone else?
Calculate the True Cost:
Onboarding a new employee can cost 30% or more of their salary.
Factor in the time and energy you’ll spend training and managing.
Be Brutally Honest:
Ask yourself: “If I hired myself into this role, would I succeed?”
If the answer is no, fix the gaps before bringing someone on.

Expert Advice:

“The excitement of bringing someone on can cloud judgment. You have to look beyond the resume and the past achievements and really assess if they fit your current needs and culture.” — Jeremy Axel

Tip 3: Structure, Accountability, and Regular Reviews

Why It Matters:

Startups often lack the structure of mature organizations, making it easy for roles and responsibilities to blur.

Actionable Steps:

Set Guardrails:
Define boundaries for each role. Avoid letting employees drift into areas where they can’t excel.
Implement Regular Reviews:
Use 30-, 60-, and 90-day check-ins to assess performance and fit.
Be ready to address issues head-on, don’t wait for problems to fester.
Spot-Check and Verify:
Trust your team, but verify results. Ask for proof of progress and outcomes.

Expert Advice:

“I’ve done instant spot checks with people, and if they can’t show me proof or results, it’s a red flag.” — Doug Cox

Tip 4: The Risks of Hiring Friends and Family

Why It Matters:

Mixing business with personal relationships can blur boundaries and create emotional landmines.

Actionable Steps:

Set Boundaries Upfront:
Clearly separate business and personal relationships.
Consider adding a clause in the employment contract about maintaining professional boundaries.
No Special Treatment:
Treat friends and family like any other employee, no exceptions.
Be Prepared for Tough Conversations:
If things go wrong, be ready to prioritize the business over the relationship.

Expert Advice:

“Inside the business, it’s business. Outside, it’s friendship. Mixing those lines without clarity can ruin both the business and the relationship.” — Jeremy Axel

Tip 5: Assessing Fit—Beyond the Resume

Why It Matters:

A great resume and interview performance don’t always translate to success in a startup environment.

Actionable Steps:

Look for Adaptability:
Can the candidate handle ambiguity and rapid change?
Are they willing to take on new challenges outside their comfort zone?
Test for Culture Fit:
Do their values align with yours?
Are they excited about your mission and vision?
Beware of “Big Company” Habits:
Candidates from large organizations may struggle with the lack of structure in a startup.

Expert Advice:

“In startups or small businesses without many layers of management or complex structures, it’s easier to see when someone is not fully delivering or when they’re relying too heavily on past experiences that don’t translate well to the current culture.” — Jeremy Axel

Tip 6: Foster Growth—For the Business and the Individual

Why It Matters:

As your business grows, your team must grow with it. Stagnation, personal or professional, can hold everyone back.

Actionable Steps:

Have Ongoing Conversations:
Regularly discuss your employees’ goals and aspirations.
Ask: “Is this vehicle (the job or company) going to get you to the lifestyle you want to live?”
Encourage Personal Development:
Support learning, training, and growth opportunities.
Look for signs of growth outside of work, self-awareness, relationship skills, etc.
Re-Interview for the Future:
Ensure your team remains aligned and adaptable as the company grows.

Expert Advice:

“Personal growth outside of work, such as in relationships and self-awareness often reflects an employee’s capacity to grow within the business.” — Jeremy Axel

Tip 7: Address Misalignment Quickly—Don’t Carry Dead Weight

Why It Matters:

One misaligned employee can drag down morale, productivity, and momentum.

Actionable Steps:

Listen to Your Team:
Frontline employees often have the clearest view of who is adding value and who isn’t.
Act Decisively:
If someone isn’t meeting expectations or aligning with your vision, address it quickly.
Don’t be afraid to let people go for the good of the team.
Part Ways Amicably:
If the role isn’t right for someone, support their transition out of the company.

Expert Advice:

“When ‌someone is holding the team back, it’s time to make a change for the good of the whole.” — Doug Cox