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Trusts aren’t just for the rich. Every family can benefit from one. A revocable living trust can simplify estate planning, avoid probate, and create a foundation for generational wealth.

In this episode, Mike Jesowshek, CPA, sits down with Jack Fiveash, attorney and co-founder of The Co Letter, to talk about how families can use a simple trust and LLC structure to build long-term stability, protect assets, and involve their children in smart financial stewardship.

They cover how to start a revocable trust, the ideal timing, what it costs, and how it ties into a broader family office structure that preserves both wealth and values.

👉 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) Building a Family Office from the Ground Up
Why wealth preservation starts with structure, not income level.

(01:00) What a Family LLC Really Means
How families can use an LLC or corporation to start engaging the next generation.

(03:05) Why Every Family Needs a Revocable Living Trust
How a trust simplifies estate planning, avoids probate, and keeps family assets under control.

(05:00) When to Create a Trust for Your Kids
What age to involve children in trust planning and why earlier is better.

(06:20) The Real Cost and Complexity of Setting Up a Trust
How much you should expect to pay and what makes a “simple but solid” setup.

(10:35) Avoiding Probate and Protecting Assets
How funding your trust correctly prevents future court battles and delays.

(11:00) Involving Family Early and Teaching Financial Literacy
Turning allowances into tax-deductible payments and getting kids engaged in the business.

(16:00) Turning Family Vacations into Business Meetings
Legitimate ways to host family meetings and create structure while maintaining compliance.

(18:00) Starting Small with a Family LLC or Partnership
How to build an investment or education fund for your kids without high legal costs.

(20:00) Structuring Your Family Business for the Future
How to align trusts, wills, and share ownership to protect the next generation.

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.

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If you earn over $250,000 or plan to sell a highly appreciated asset, this episode could save you hundreds of thousands in taxes. Most business owners stop at basic deductions and retirement plans, but the wealthy use strategies that go far beyond that.

In this episode, we break down the five categories of advanced tax planning, when they apply, and how to use them the right way.

👉 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) When Advanced Tax Planning Matters
Why high-income earners and those selling appreciated assets should consider advanced strategies.

(01:00) Core vs. Advanced Strategies
The difference between foundational tax tactics available to everyone and advanced ones designed for high earners or large one-time gains.

(03:10) The Government Rewards Tax Planning
How tax incentives are built to encourage investment in business, housing, and energy projects.

(05:00) The Five Categories of Advanced Tax Strategies
An overview of the five areas where the wealthy focus their planning.

(05:23) Advanced Retirement Planning
Cash balance plans, mega backdoor Roths, non-qualified plans, and self-directed accounts for those already maxing out standard retirement limits.

(06:24) Asset Purchase Strategies
Using leverage and depreciation to create large year-one deductions. Example: turning a $10,000 down payment on a Turo car into a $100,000 deduction.

(08:00) Asset Donation Strategies
Buying assets at a discount and donating them at full fair market value to increase charitable deductions.

(09:00) Oil and Gas Investments
How investors receive 80 to 90 percent year one deductions through intangible drilling costs and depletion allowances.

(10:14) Captive Insurance Companies
Creating your own insurance company to protect your business while shifting income into a tax-advantaged structure.

(11:16) What to Consider Before Using Advanced Strategies
Material participation requirements, IRS scrutiny, vendor due diligence, and understanding investment or loan obligations.

(14:00) Finding the Right Fit
Why working with a tax strategist helps you find the combination of strategies that fits your goals.

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 you

Send us a text

Are you spending money the wrong way? Every dollar is either pre-tax or after-tax money. Knowing the difference is the key to thousands in tax savings.

In this episode, we cover how to turn everyday expenses into business deductions. From meals and travel to home office and even hiring your kids, you’ll learn the mindset shift that could save you thousands each year.

👉 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) Pre-Tax vs. After-Tax Spending
Why most business owners spend the wrong way and how to flip it.

(01:18) Ordinary and Necessary Expenses
What makes an expense deductible, and how to pass the audit test.

(04:00) Everyday Costs You Can Deduct
Home office, vehicle, meals, travel, tech, cell phone, and subscriptions.

(06:27) Hiring Your Kids
How shifting family costs into payroll creates big tax savings.

(08:24) Live Audit of a Credit Card Statement
Mike reviews personal spending line by line to uncover missed deductions.

(13:10) The Framework for Deductions
Rationale, recordkeeping, and reasonableness: How to defend expenses.

(14:45) Documentation Tips to Protect Yourself
How to prove expenses with receipts, notes, and an accountable plan.

(16:15) Action Steps to Maximize Tax Savings
Start small, pick categories, and track better to save thousands. $100 pre-tax is worth $100. $100 after-tax is only worth $65.

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.