Money Matters Radio Show #11 - Hiring Help: When to Hire, Who to Hire, and How to Afford It

Money Matters Radio Show #11 - Hiring Help: When to Hire, Who to Hire, and How to Afford It

Radio Show Summary

This week on Money Matters, Kash dives into one of the biggest growth moments in any business: bringing someone else on board. These episodes break down how to know when it’s time to hire, what kind of help makes the most sense (employee vs. contractor), and how to handle the financial side of building your team. Plus, Kash gets real about the emotional side of delegation—like why it's so hard to let go and how to do it without blowing your budget or your boundaries.

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Key Takeaways

[Episode 41] Ready to Hire? The Financial Signs to Watch For

In this introductory discussion, we dive into why understanding the right time to hire is crucial for business owners. We cover the importance of stepping outside your accounting comfort zone to embrace hiring when your business needs it.


Key Takeaways:

  • Reconcile all accounts before year-end.
  • Review and categorize final expenses and income.
  • Backup your financial files for easy access.

[Episode 42] Get Help Where It Hurts: Know When It’s Time to Delegate

As we continue, I emphasize the personalized nature of hiring, unfurling how identifying tasks outside one's expertise can be a game-changer.


Key Takeaways:

  • Evaluate which activities take you away from revenue-generating work.
  • Hiring isn’t just for experts; it can streamline your focus on business growth.
  • Leverage both employees and contractors to delegate effectively.

[Episode 43] 1099 or W-2? Hiring Smart with Tax Strategy in Mind

We explore the nitty-gritty of using financial savvy to decide between hiring a 1099 contractor or a W-2 employee, blending strategic financial planning with employee engagement.


Key Takeaways:

  • The right choice between W-2 and 1099 impacts your long-term strategy and commitment.
  • Planning for taxes via payroll systems stabilizes financial health.
  • Ensure the value of hiring outweighs the costs through analysis and planning.

[Episode 44] Hiring Lessons from the Trenches: Real Talk on Team Growth

In the finale, we unravel delightful accounting tales, demonstrating hiring and growth through real-world examples peppered with wit and wisdom.


Key Takeaways:

  • Cash flow is a pivotal element when expanding your team.
  • Early HR investments save time and ensure quality hires as demand surges.
  • Pre-planned hiring, with a financial safety net, supports deliberate, predictable growth.

Meet Your Host

Kasfia “Kash” Rashid is the founder of Kash the Bookkeeper and host of the globally streamed Money Matters radio show. A bookkeeping expert and financial coach, Kash specializes in helping small business owners finish strong and start fresh with clarity and strategy—no judgment, just results.

Final Thoughts

Take an honest look at where your time is going. What tasks are draining your energy or falling through the cracks? Make a list and decide which ones need to stay on your plate and which could be handed off. From there, define the role you actually need—not just the job title. Then, run the numbers: what can your business truly afford right now? Whether it’s a part-time VA or a full-time hire, clarity up front keeps your growth smooth, sustainable, and aligned with your goals.


Ready to end strong? Subscribe to Money Matters and leave a review. Know a fellow business owner bracing for year-end chaos? Share this week’s episodes and help them close the books with confidence.

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