Mondays with Matt

Hiring Your First Employee: Key Considerations for Entrepreneurs


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Hiring your first employee is one of the biggest decisions you'll make as a business owner. In this episode of Build Your Business, Matt and Chris Reynolds explore everything you need to know before making that first hire—from financial readiness to ensuring a strong cultural fit.

Are You Ready to Hire Your First Employee?

Hiring too soon—or without the right systems in place—can do more harm than good. Matt and Chris explain:

  • Why you should have 6 months of payroll saved
  • How to identify tasks you should delegate
  • The importance of onboarding systems and SOPs
  • Why time commitment—not just financial readiness—matters

Financial Readiness: Are You Prepared to Pay Your First Employee?

Hiring involves more than just writing a paycheck.

  • Understand the full cost: salary, taxes, benefits, admin expenses
  • Model how hiring affects your financial forecasts
  • Have a cushion for months when the hire isn't yet generating ROI
  • Avoid financial stress by staying prepared

Hiring for Skills and Cultural Fit

It's not just what they do—it's how they work with you.

  • Hire for skills and shared values
  • Be clear on the role and expected outcomes
  • Weigh the pros and cons of hiring someone you already know
  • Focus on long-term compatibility, especially in small teams

#Entrepreneurship #HiringTips #BuildYourBusiness

PS - Coach Smarter, Earn More: https://bit.ly/3X4ixOX Matt's Links Website: https://ryanmattreynolds.com/ Instagram: https://www.instagram.com/reynoldsstrong/?hl=en Chris's Links: LinkedIn: https://www.linkedin.com/in/chrismreynolds/

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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