Estimated taxes should not feel like a guessing game, but for many business owners, they do. Underpay, and you face stress, penalties, and a big bill in April. Overpay, and you hand the IRS more cash than needed, limiting what you can reinvest in your business.

In this episode, we break down how estimated taxes actually work, why the U.S. tax system is pay-as-you-earn, and how to avoid both overpaying and underpaying. We cover the safe harbor rules, why accurate bookkeeping matters, and how to build a smarter system for quarterly payments that improves cash flow and reduces surprises.

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:
https://www.taxsavingspodcast.com/starterkit

🚀 Book your free demo call today. Click here or visit:
https://taxelm.com/demo/

Chapters

(02:15) Why Business Owners Fall Behind on Quarterly Taxes
Without an employer withholding taxes, business owners are responsible for making estimated payments themselves, and many ignore them until penalties and interest build up.

(03:45) Why Last Year’s Income Is Not Enough
Many business owners base estimated taxes on last year’s income or send in whatever feels safe, but income, deductions, entity structure, and tax law can all change.

(04:30) The Safe Harbor Rules You Need to Know
To generally avoid underpayment penalties, you need to pay 100% of last year’s tax liability, 110% for certain higher-income earners, or 90% of this year’s tax liability.

(06:30) The Cash Flow Cost of Overpaying and Underpaying
Overpaying estimated taxes can tie up money that could be used for marketing, debt reduction, equipment, or other business needs, only to result in a refund later, while underpaying creates pressure when tax time comes, especially if business profits rise and estimated payments were never adjusted upward during the year.

(08:40) How to Calculate Estimated Taxes More Strategically
The process starts with a quarterly profit analysis, then projecting the rest of the year forward, and finally adjusting payments intentionally based on current numbers.

(10:40) Estimated Tax Due Dates Every Business Owner Should Know
Quarterly estimated tax payments follow a set schedule throughout the year, and knowing those due dates is essential for staying compliant and avoiding surprises.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit: https://www.TaxSavingsPodcast.com

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

Are you worried a tax strategy could land you in trouble with the IRS?

In this episode, Mike Jesowshek sits down with tax attorney Ed Lyon to break down what tax risk actually means. They explain why most business owners do not get in trouble for smart tax planning, where the line between gray-area strategy and fraud really sits, and why proper implementation matters just as much as the strategy itself.

They cover audit risk, common red flags, what to ask before moving forward with an advanced strategy, and how business owners should think about their own risk tolerance when building a tax plan.

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:
https://www.taxsavingspodcast.com/starterkit

🚀 Book your free demo call today. Click here or visit:
https://taxelm.com/demo/

Chapters

(02:00) Why Business Owners Fear Tax Planning
People don't go to jail for legal tax planning. They go to jail for fraud, lying, and backdating documents.

(05:00) Why Tax Strategies Exist in the First Place
The tax code is designed to encourage certain behavior. Congress uses tax incentives to push homeownership, healthcare benefits, investing, and charitable giving.

(12:00) When a Legal Strategy Becomes Illegal
A strategy can be perfectly valid in theory, but fail when implemented poorly.

(24:00) How to Vet an Advanced Tax Strategy
When someone pitches an advanced strategy, transparency matters. Ed explains what questions to ask, what red flags to look for, and why business owners need to understand who they are dealing with before moving forward.

(27:00) How Business Owners Should Think About Risk
Tax risk is just another business risk. The real goal is to understand your own risk tolerance, know where your advisor falls on the conservative-to-aggressive spectrum, and make informed decisions.

(31:00) A Favorite Strategy for the Right Client
Ed closes by sharing one tax strategy he likes for the right candidate, the charitable lead trust, and explains why the best strategy always depends on the client’s goals, income, and long-term plan.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit: https://www.TaxSavingsPodcast.com

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

You’ve hired your first employee… Now what? Hiring your first employee introduces a new layer of tax responsibility, compliance, and systems that many business owners are not prepared for. You are now managing payroll taxes, filings, labor laws, and deadlines that carry real penalties if handled incorrectly.

In this episode, we break down exactly what happens after you hire your first employee so you can avoid costly mistakes and set your business up to scale the right way. We cover the difference between W2 employees and 1099 contractors, the real cost of payroll taxes, how to stay compliant with state and federal requirements, and why payroll software is a must.

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:
https://www.taxsavingspodcast.com/starterkit

🚀 Book your free demo call today. Click here or visit:
https://taxelm.com/demo/

Chapters

(01:00) Employee vs Contractor: What the IRS Looks At
Classification comes down to control. Who sets hours, pay, tools, and how the work gets done determines W2 vs 1099.

(04:00) The Payroll Tax Reality Business Owners Miss
Hiring an employee makes you a tax middleman responsible for withholding and paying multiple taxes.

(06:00) What You Need Before Running Payroll
You need an EIN, state withholding accounts, unemployment accounts, and workers’ compensation set up first.

(07:30) Why Payroll Software Is Non-Negotiable
Payroll software handles tax calculations, filings, deposits, and compliance to avoid penalties and costly mistakes.

(09:30) The Risk of Missing Payroll Tax Deadlines
Late payments trigger immediate penalties and interest, and payroll mistakes can shut down businesses.

(12:00) Benefits Without Breaking the Bank
Health reimbursement arrangements and simple retirement plans offer affordable ways to provide benefits.

(14:30) Hiring Employees in Other States
Out-of-state hires require additional registrations, tax accounts, and possible foreign entity filings.

(16:00) Key Takeaways
Hiring is a growth milestone. Set up systems correctly, use payroll software, and build processes that allow your business to run without you.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit: https://www.TaxSavingsPodcast.com

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.