The Mid-Year CEO Tax Check-In: What You’re Responsible for (and Why It Matters) – Ep. 232

2025-07-22

Ready to stop scrambling come tax time and start planning like the business leader you are? Well, it starts with your mid-year financial game plan. In this episode, Danielle Hayden, CEO and founder of Kickstart Accounting, Inc., walks you through the steps you need to take to get your books in shape, plan for tax season (without stress), and build a business that's profitable and sustainable for the long haul. Let's make tax season feel like just another Tuesday. Key Takeaways: Know the Kind of Business You're Building: Are you running ...

Ready to stop scrambling come tax time and start planning like the business leader you are? Well, it starts with your mid-year financial game plan.

In this episode, Danielle Hayden, CEO and founder of Kickstart Accounting, Inc., walks you through the steps you need to take to get your books in shape, plan for tax season (without stress), and build a business that's profitable and sustainable for the long haul. Let's make tax season feel like just another Tuesday.

Key Takeaways:

Know the Kind of Business You're Building: Are you running a tax deduction-focused business or building long-term sustainability? Defining this upfront will shape your entire financial strategy and mindset.
Bookkeeping Is the Foundation of Everything: You can't make smart tax or financial decisions without accurate, up-to-date books. Get caught up and stay caught up.
Collect W-9s and Log Expenses Now, Not Later: Save yourself a year-end headache by organizing contractor paperwork and tracking home office, mileage, and reimbursable expenses today.
Review Your Entity Type and Compensation: Are you set up as the right business entity? S-Corps, in particular, need to pay close attention to reasonable compensation and accountable plans.
Don't Skip Estimated Tax Payments: Avoid penalties and cash flow surprises by paying what you owe and saving for taxes proactively—your future self will thank you.

⭐ Business Hack: Schedule a full "CEO Day" to knock all this off your plate!

Topics Discussed:

(00:31 – 01:15) Why Mid-Year Is the Best Time for Financial Planning

(01:16 – 04:53) Choosing the Kind of Business You Want to Run

(04:59 – 06:54) Bookkeeping Updates: What to Check and Why It Matters

(06:55 – 11:15) Must-Do Mid-Year Admin: W-9s, Home Expenses, Mileage Tracking

(11:24 – 16:00) Reviewing Entity Type, Reasonable Compensation, and Estimated Taxes

Resources:

Free Downloadable Template | Home Office Log & Accountable Plan

Episode Referenced | Entrepreneurs: Should You Go S-Corp? Pros & Cons + Expert Insight – Ep 115

Book a Call with Kickstart Accounting, Inc.:

https://kickstartaccountinginc.com/book-a-call/