Most business owners think tax season is about filing returns.
In reality, the biggest tax opportunities happen the other nine months of the year.

In this episode of the Empowering Healthy Business Podcast, Cal Wilder talks with Greg Reed about what your CPA should be telling you—especially if you want fewer surprises and better decisions year-round.

They discuss the difference between tax prep and tax planning, why not all tax savings are equal, how multi-year strategy works, and when paying more tax can actually support growth.

In this episode:

• Why filing early doesn’t mean you’re planning well
• The difference between deductions, credits, and deferrals
• Why income smoothing matters
• When higher taxable income helps with funding
• Why entity structure and owner pay need regular review
• The truth about extensions and safe harbor estimates
• Why tax planning must be proactive

If you’re only meeting your CPA once a year, this episode may change how you think about taxes.

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Sponsored by SmartBooks. To schedule a free consultation, visit smartbooks.com.

Thanks for listening!

Host Cal Wilder can be reached at:
cal@empoweringhealthybusiness.com
https://www.linkedin.com/in/calvinwilder/

Tax season doesn’t cause stress because of paperwork; it causes stress because business owners don’t know what’s coming.

In this episode of the Empowering Healthy Business Podcast, Cal Wilder talks with Greg Reed, Head of Tax at SmartBooks, about how business owners can prepare for tax season in January to avoid surprises and reduce anxiety.

They break down the difference between tax filing, projections, planning, and coaching, and explain what steps actually make tax season smoother.

In this episode, you’ll learn:

• Why uncertainty creates tax anxiety
• What to organize in January to stay ahead
• How clean bookkeeping impacts tax prep
• How to prepare for 1099s and estimated payments
• When itemized deductions may apply again
• Why proactive tax support matters

If tax season feels stressful every year, this episode will help you approach it with more clarity and control.

Send us a text

Thanks for listening!

Host Cal Wilder can be reached at:
cal@empoweringhealthybusiness.com
https://www.linkedin.com/in/calvinwilder/

Choosing the right retirement plan is one of the most important—and confusing, decisions a business owner makes.

In this episode of the Empowering Healthy Business Podcast, Calvin Wilder talks with Charles Reichelt about how small business owners can design retirement plans that work for both the owner and the team.

They cover the pros and cons of different plan types, how to manage costs and compliance, and how employee education plays a critical role in plan success.

In this episode, you’ll learn:

• How different retirement plans work for small businesses
• When to use a 401(k), SIMPLE IRA, SEP IRA, or solo 401(k)
• How to increase owner contributions while staying compliant
• How to keep plan fees transparent and competitive
• When it’s time to benchmark or redesign your plan

If you’re starting a retirement plan, or wondering whether your current plan still fits, this episode provides clear guidance to help you make confident decisions.
Charles Reichelt - FTG Squared
Direct phone: 301-466-9945

Send us a text

Sponsored by SmartBooks. To schedule a free consultation, visit smartbooks.com.

Thanks for listening!

Host Cal Wilder can be reached at:
cal@empoweringhealthybusiness.com
https://www.linkedin.com/in/calvinwilder/