Small tax mistakes can cost you thousands, even when you think you’re doing everything right.

From missing a filing deadline to misunderstanding how a deduction works, small errors can quickly turn into penalties, lost deductions, and a higher tax bill.

In this episode, Mike answers real tax questions from small business owners covering gambling losses, BOI reporting, moving an S corporation to another state, the Augusta Rule, HSAs, late 1099s, estimated tax penalties, startup expenses, vehicle write-offs, and more. He breaks down the rules, explains the available options, and shares practical steps to help you stay compliant and avoid costly tax mistakes.

👉 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

00:45 Gambling Losses, BOI Reporting, and Moving an S Corp
Mike explains gambling deductions, current BOI filing rules, and what happens when an S corporation moves states.

05:40 The Augusta Rule, HSAs, and Nonprofit Approval
Learn how to document Augusta Rule meetings, coordinate HSA contributions, and apply for 501(c)(3) status.

10:20 Health-Sharing Plans, Late 1099s, and Estimated Tax Penalties
Mike covers health-sharing deductions, missed 1099 deadlines, and penalties after a late-year property sale.

16:25 Seasonal Income, Inventory Credit, and Pre-Revenue Businesses
Find out how seasonal businesses handle estimated taxes, how much inventory to finance, and what to file before earning revenue.

20:15 Late Schedule C Filings, C Corp Owner Pay, and Vehicle Write-Offs
Mike explains prior-year Schedule C filings, how C corporation owners are paid, and choosing between mileage and actual vehicle expenses.

Resources Mentioned:

👉 www.FinCen.gov

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.

Your CPA isn’t saving you money… And it’s probably not their fault.

Many business owners expect their CPA to handle everything: bookkeeping, tax filing, tax strategy, and financial guidance.

In this episode, Mike breaks down the four financial roles every business owner needs to understand: bookkeeper, tax preparer, tax strategist, and CFO or advisor. He explains what each role does, what they do not do, and how building the right financial team can help you stay compliant, make better decisions, and legally lower your tax bill.

👉 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

01:45 The Four Financial Roles Every Business Owner Needs
A strong financial team is usually made up of multiple roles, not one person. The key roles are bookkeeper, tax preparer, tax strategist, and CFO or advisor.

02:00 The Bookkeeper: The Historian
Bookkeepers track income, expenses, transactions, and financial statements. They help create clean, accurate books, but they usually do not provide tax strategy or planning advice.

03:00 The Tax Preparer: The Reporter
Tax preparers file returns using completed books and past financial data. Their work focuses on compliance, not optimization, which is why tax filing alone usually does not create tax savings.

04:25 The Tax Strategist: The Architect
Tax strategists look forward and build a plan to legally reduce taxes. This may include timing income, maximizing deductions, reviewing entity structure, and implementing proactive tax strategies.

05:55 The CFO or Advisor: The Navigator
A CFO or advisor focuses on bigger financial decisions like cash flow, growth, profitability, and next steps. This role becomes more important as the business scales.

08:35 What a CPA Actually Is
A CPA is a credential, not a guaranteed service package. Some CPAs prepare tax returns, some provide planning, some focus on bookkeeping, and some do not work in tax at all.

11:35 Where TaxElm Fits Into the Financial Team
TaxElm focuses on the tax strategy layer. It does not replace bookkeepers or tax preparers, but helps business owners with proactive year-round planning and strategy implementation.

13:35 How to Know What Your Business Actually Needs
The starting point depends on the gap in your business. Messy books point to bookkeeping, recurring surprise tax bills point to tax planning, and growth challenges may point to CFO-level advisory.

16:00 A Simple Framework for Your Financial Team
Business owners need clean books, accurate filing, proactive planning, and strategic growth.

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.

Your bookkeeping changes everything from a tax standpoint.

If your books are messy, outdated, or based on guesswork, your tax planning is already working with bad information. You may miss deductions, misjudge your profit, make poor year-end decisions, or overpay the IRS without realizing it.

In this episode, Mike breaks down why bookkeeping is not just administrative work. It is the foundation of smart tax planning. He explains what bookkeeping actually is, how your profit and loss statement and balance sheet affect your taxes, and why clean, accurate books help business owners make better decisions, reduce tax-season stress, and uncover more opportunities to lower their tax bill.

👉 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

00:58 Why Business Owners Ignore Bookkeeping Early
Many new business owners focus on sales, growth, employees, and operations while treating bookkeeping as an afterthought. This creates problems later with taxes, stress, and missed opportunities.

03:15 Why Bookkeeping Is a Tax Strategy
Tax strategy starts with accurate data. Business owners can’t maximize deductions, time income, plan asset purchases, or make smart tax decisions if their numbers are wrong.

06:30 Understanding the Profit and Loss Statement
The profit and loss statement shows income, expenses, and profit. Since taxable income often starts with profit, this statement is where many tax-saving opportunities begin.

10:45 The Main Types of Bookkeeping Transactions
There are four main transaction types to track: bank and credit card transactions, non-cash transactions, invoices, and bills. Where each transaction lands affects the tax impact.

13:30 Common Bookkeeping Mistakes Business Owners Make
Common mistakes include inconsistent tracking, waiting until tax season, mixing business and personal expenses, and failing to keep clean records for 1099s.

15:00 What Accurate Books Actually Give You
Clean bookkeeping helps business owners stop overpaying taxes, see opportunities in real time, make better decisions, reduce tax-season stress, and move from reactive to proactive planning.

16:00 A Simple System for Better Bookkeeping
A simple bookkeeping system starts with cloud-based software, weekly transaction categorization, separate business and personal finances, and professional help when needed.

Resources Mentioned:

👉 Kick: https://refer.kick.co/mike-jesowshek-cpa

👉 Quickbooks: https://quickbooks.partnerlinks.io/4k3apzwyyyhf

👉 Xero: https://xero5440.partnerlinks.io/i98ammvf3g9h-nx0cim

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.