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If I were starting a business today, this is exactly how I’d approach tax planning from the ground up. In this episode, we're tackling tax strategy hierarchy every small business owner should follow.

From core strategies like hiring your kids and maximizing deductions, to advanced moves like asset purchases, oil and gas investments, and captive insurance, you’ll learn the right order to implement them for maximum savings. We also answer listener questions on short-term rental deductions, the Big Beautiful Bill, and how to structure partnerships for smarter tax planning.

👉 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:

(00:00) Starting From Scratch
Mike shares his “from scratch” game plan for small business tax planning and breaks down the difference between core and advanced tax strategies.

(04:04) Big Beautiful Bill Overview
What’s in the Big Beautiful Bill, how it impacts small businesses, and where to find the full breakdown.

(05:00) Planning for Income Phase-Outs
Strategies for lowering AGI to avoid phase-outs and AMT for high earners.

(08:00) Short-Term Rental Deductions
How to qualify, the 100-hour rule, and how bonus depreciation applies.

(12:15) 1099 Income Advantages
Why 1099 workers are treated as business owners and the deductions that come with it.

(14:00) Self-Rental and Asset Purchase Strategies
Using a self-rental strategy and advanced asset purchases to significantly reduce taxable income.

(15:53) Adjusting S Corp Salary
How to handle a reasonable salary when business revenue drops.

(17:00) Home Office Deduction Methods
Comparing the simplified and actual methods for the home office deduction.

(18:46) Structuring Partnerships for Tax Planning
Entity structures that allow partners with different tax needs to plan separately.

(20:58) Accessing S Corp Profits
How to take owner’s draws and keep your salary reasonable.

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.

Send us a text

Most business owners think of insurance as a necessary expense, but what if it could double as a tool to cut taxes? With a Section 831(b) captive insurance company, you can set aside pre-tax dollars to cover risks traditional insurance won’t touch… All while building a financial safety net for your business. In this episode, Van Carlson, founder of SRA 831(b), explains how captives work, the types of risks they can cover, when it makes sense to use one, and how to stay compliant under IRS rules.

👉 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:

(01:34) What Is a Captive Insurance Company?
Captive insurance companies let businesses self-insure specific risks using Section 831(b) for tax-deferred funding.

(02:55) Funding Uninsured Risks
Unfunded liabilities can drain after-tax cash, but 831(b) allows businesses to cover them with pre-tax dollars.

(06:00) Captive vs. 401(k) Comparison
A captive works like a 401(k) for risk, building tax-deferred reserves instead of retirement savings.

(10:41) What Captives Actually Cover
Captives can insure supply chain disruption, brand damage, cyber threats, and more through “halo coverage.”

(15:58) How Do You Set Up And Run a Captive?
Setting up a captive involves forming a C corporation, underwriting policies, pooling risks, and managing claims.

(25:48) IRS Scrutiny and Compliance
How to avoid common pitfalls by ensuring proper risk pooling, accurate underwriting, and full documentation.

👉Learn more about Captive Insurance and Section 831(b) at SRA 831(b): https://www.831b.com

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.

Send us a text

Retirement expert Matt Ruttenberg walks through 5 real-world business scenarios and how to choose the smartest retirement plan for each. Whether you're flying solo or managing a growing team, this episode breaks down IRA, SEP, SIMPLE, 401(k), and advanced options in a simple way… Plus, how to take advantage of powerful tax credits.

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

🚀 Build a smarter retirement strategy for your business. Visit: https://lifeincrs.com/tax-savings-podcast/

Chapters:

(00:00) Most Business Owners Are in the Wrong Plan
Most entrepreneurs are saving in the wrong retirement account—or missing out completely.

(01:42) Scenario 1: Solo Owner Saving Less Than $6K
If you're saving under $7,000/year, a traditional or Roth IRA is likely all you need.

(03:57) Scenario 2: Solo Owner Saving Around $12K
Explore SEP vs. SIMPLE IRA options based on your business type and how you pay yourself.

(07:51) Scenario 3: Solo Owner Saving $25K+
When your savings goals go up, consider a Solo 401(k) for higher limits and flexibility.

(16:02) Scenario 4: Business With Employees—Recruit & Retain
Use a SIMPLE or Traditional 401(k) to attract employees without overcommitting on costs.

(21:32) Scenario 5: Max Out Retirement With Employees
How to design a Safe Harbor 401(k), profit sharing, and defined benefit plan to maximize owner contributions while minimizing employee costs.

(26:57) Big Tax Credits That Cover Admin Costs & Matches
Secure 2.0 offers up to $50,000 in tax credits for new retirement plans—free money you shouldn’t miss.

(30:52) Setup Deadlines & What to Know for 2025
Important plan setup deadlines and why talking to a specialist can prevent costly mistakes.

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.