Best Mike Jesowshek Podcasts (2025)

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How to Reimburse Yourself Tax-Free (The Accountable Plan Explained) 14:55

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2d ago14:55

14:55

Send us a text If you’ve ever paid for business expenses out of pocket, like your phone bill, internet, or home office, and wondered if you can get reimbursed without paying more tax, this episode is for you. In this episode, you’ll learn how an Accountable Plan lets business owners legally reimburse themselves and their employees tax-free. You’ll …

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How to Turn Medical Bills Into Tax Deductions (4 Ways to Deduct Health Costs) 17:26

9d ago17:26

17:26

Send us a text A single medical bill can wipe out your profits. But health expenses don’t have to drain your cash flow. In this episode, you’ll learn three powerful ways to turn your medical costs into legitimate tax deductions. From self-employed health insurance and Health Savings Accounts (HSAs) to Section 105 reimbursement plans and employee he…

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Why Every Family Needs a Trust & LLC (Not Just the Rich) 30:35

16d ago30:35

30:35

Send us a text 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 si…

1
Advanced Tax Strategies the Ultra-Wealthy Use (and How You Can Too) 17:21

23d ago17:21

17:21

Send us a text 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…

1
Turn Everyday Expenses Into Deductions (Max Out Your Tax Savings) 19:06

1M ago19:06

19:06

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 c…

1
Live Case Study: How We Cut $20K+ Off His Tax Bill (Step by Step) 44:22

1M ago44:22

44:22

Send us a text What happens when you take a real small business owner, put them in the hot seat, and break down their tax strategy live? That’s what we’re doing in this episode. Eric runs a successful appraisal business, pays himself through an S-Corp, and last year wrote a $50,000 check to the IRS. Did he really have to? Mike digs into Eric’s setu…

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Auto Deductions Explained: The 2025 Tax Rules You Need to Know 22:34

1M ago22:34

22:34

Send us a text Most business owners are driving right past thousands in tax savings without realizing it. In 2025, the IRS raised the standard mileage rate to 70 cents per mile, but that’s only the beginning. In this episode, Mike breaks down exactly how to structure your auto deductions, avoid costly mistakes, and choose between the mileage method…

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The Home Office Deduction Explained: How to Save Up to $1,500 a Year 22:27

2M ago22:27

22:27

Send us a text Do you have a home office? The desk you’re sitting at could save you up to $1,500 a year in taxes. Many business owners skip this deduction because they think they don’t qualify or fear an IRS audit. The truth is, most do qualify. One client of mine saved $1,100 in just 30 minutes by setting it up. In this episode, Mike Jesowshek, CP…

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Sell Your Company with $0 Taxes? QSBS Explained 32:18

2M ago32:18

32:18

Send us a text Some entrepreneurs sell their companies and walk away with zero federal taxes. How? This is thanks to a strategy called QSBS. In this episode, tax strategist Alessandro of Get Dynasty breaks down Qualified Small Business Stock, new changes from the “Big Beautiful Bill,” and how founders can use trusts to multiply tax-free exits. If y…

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Independent Contractor or Employee? Hiring Mistakes That Trigger an IRS Audit 22:35

2M ago22:35

22:35

Send us a text Misclassifying workers is one of the biggest mistakes a business owner can make. It might seem cheaper to pay someone as a 1099 contractor, but if the IRS says they should be a W-2 employee, you’re looking at back taxes, penalties, and possible audits that could cripple your business. In this episode, Mike breaks down the IRS framewo…

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Why the Wealthy Use Oil & Gas Investments to Cut Six Figures Off Their Taxes 26:53

2M ago26:53

26:53

Send us a text Most tax strategies give you either a write-off or long-term growth. Oil and gas gives you both. With IRS Code 263(c), you get massive upfront deductions and steady tax-advantaged cash flow. In this episode, Mike and Nick from US Energy unpack how drilling funds work, the unique tax benefits they provide, and how to use them strategi…

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Q&A: The Tax Strategy Hierarchy Every Small Business Owner Should Know 23:39

3M ago23:39

23:39

Send us a text 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, …

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How Section 831(b) Captive Insurance Protects Your Business and Saves You Taxes 34:02

3M ago34:02

34:02

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 Carl…

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The #1 Retirement Mistake Business Owners Make (And How to Fix It) 36:34

3M ago36:34

36:34

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. 🚀…

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Partnership vs. S Corp | How Basis Can Make or Break Your Tax Bill 15:08

3M ago15:08

15:08

Send us a text Taking money out of your business isn’t always tax-free. If you’re not tracking your basis, you could get hit with a surprise capital gains tax, even without selling anything. Let's break down what basis means, how it works differently for Partnerships and S Corps, and why overlooking it could cost you thousands. 🚀 Book your free dem…

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Don’t Mix Passive and Active Income! Your Entity Structure is Why You're Overpaying on Taxes 23:16

4M ago23:16

23:16

Send us a text Mixing active and passive income in one entity could be costing you thousands. In this episode, we break down why separating your income streams is essential. You’ll learn how to structure your business the right way using S Corps, LLCs, holding companies, and even C Corps to unlock advanced tax strategies. From hiring your kids to s…

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Trump’s ‘One Big Beautiful Bill’ Just Changed Your Taxes Forever – What’s Inside 21:00

4M ago21:00

21:00

Send us a text Trump’s Big Beautiful Bill just became law. What’s actually in it? On July 4th, the biggest tax overhaul since 2017 was signed, and it’s packed with big wins for business owners. 100% bonus depreciation, a permanent 20% QBI deduction, tax-free tips and overtime, and brand-new deductions most people haven’t even heard of. Let’s break …

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Why Loans Get Denied (Don't Apply for a Mortgage Until You Do This) 31:20

4M ago31:20

31:20

Send us a text When you're self-employed, getting approved for a mortgage isn't as straightforward as it is for W-2 employees. In this episode, Mike sits down with mortgage lender Bill Moeller to break down how tax-saving strategies can impact your mortgage application. 🚀Ready to stop overpaying the IRS? Sign up for my free webinar on July 15th! Cl…

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Don't Make These EXPENSIVE Mistakes | Mid-Year Tax Checkup 28:16

4M ago28:16

28:16

Send us a text 🚀Ready to stop overpaying the IRS? Sign up for my free webinar on July 15th! Click here or visit: https://www.taxsavingspodcast.com/webinar We’re halfway through the year, now’s the best time to check if you’re on track to pay less tax and avoid surprises. Mike explains why mid-year is the perfect time to review your entity setup, le…

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Q&A: Can I Deduct That? From Mileage to Meals, Your Tax Questions Answered 27:01

5M ago27:01

27:01

Send us a text 🚀 Ready to stop overpaying the IRS? Sign up for my free webinar on July 15th! Click here or visit: https://www.taxsavingspodcast.com/webinar Got a question about taxes, business expenses, or running your LLC? You’re not alone. In this Q&A episode, Mike tackles common questions from real business owners — covering topics like closing …

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Faith, Leadership, and Stewardship with Reggie Brooks 44:25

5M ago44:25

44:25

Love the show? Subscribe, rate, review, and share! Here’s How » Join the Capital Gains Tax Solutions Community today: capitalgainstaxsolutions.com Capital Gains Tax Solutions Facebook Capital Gains Tax Solutions Twitter Capital Gains Tax Solutions Linked In

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How to File a Late S Corporation Election and Still Save on Taxes 22:47

5M ago22:47

22:47

Send us a text Missed the S Corp deadline? Don’t panic. In this episode, Mike breaks down how to file a late S Corp election the right way so you can still unlock major tax savings. You’ll learn what an S Corp really is, who qualifies, how to calculate your savings, and what to watch out for when making the switch. Plus, the exact steps to file a l…

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Do You Need Tax Planning (Spoiler: You Might Be Missing Out) 21:41

5M ago21:41

21:41

Send us a text Most people think tax planning is only for big corporations. But it’s one of the most powerful tools any small business owner can use to save money. In this episode, Mike breaks down how tax planning is different from just filing your taxes, and why even brand-new business owners should be thinking about it. He also shares a real cas…

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Want Tax-Free Income in Retirement? Start with a Roth Conversion 19:13

5M ago19:13

19:13

Send us a text You’ve heard of Roth IRAs, but no one talks about when and how to convert. In this episode, Mike breaks down exactly how a Roth conversion works, when it makes sense, and how to use it to build tax-free income in retirement. He also unpacks the key differences between Traditional and Roth accounts, plus real-life stories of business …

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Wealth Preservation: Gold & Silver with Dana Samuelson 37:46

5M ago37:46

37:46

Love the show? Subscribe, rate, review, and share! Here’s How » Join the Capital Gains Tax Solutions Community today: capitalgainstaxsolutions.com Capital Gains Tax Solutions Facebook Capital Gains Tax Solutions Twitter Capital Gains Tax Solutions Linked In

1
Business Entity Compliance 101: What You MUST Know 38:25

5M ago38:25

38:25

Send us a text Are you 100% sure your business entity is compliant? In this episode, Mike is joined by Nellie Akalp, CEO of CorpNet, to break down what compliance really means for LLCs and corporations. They cover everything from annual reports, meeting minutes, and registered agents to BOI reporting and choosing the right state to form your entity…

Mike Jesowshek Podcasts

1
Small Business Tax Savings Podcast

Mike Jesowshek, CPA

1
Law Firm Accounting and Tax Podcast

Mike Jesowshek, CPA

1
Positive Input

Positive Input

1
Capital Gains Tax Solutions Podcast

Brett Swarts

1
How to Reimburse Yourself Tax-Free (The Accountable Plan Explained) 14:55

1
How to Turn Medical Bills Into Tax Deductions (4 Ways to Deduct Health Costs) 17:26

1
Why Every Family Needs a Trust & LLC (Not Just the Rich) 30:35

1
Advanced Tax Strategies the Ultra-Wealthy Use (and How You Can Too) 17:21

1
Turn Everyday Expenses Into Deductions (Max Out Your Tax Savings) 19:06

1
Live Case Study: How We Cut $20K+ Off His Tax Bill (Step by Step) 44:22

1
Auto Deductions Explained: The 2025 Tax Rules You Need to Know 22:34

1
The Home Office Deduction Explained: How to Save Up to $1,500 a Year 22:27

1
Sell Your Company with $0 Taxes? QSBS Explained 32:18

1
Independent Contractor or Employee? Hiring Mistakes That Trigger an IRS Audit 22:35

1
Why the Wealthy Use Oil & Gas Investments to Cut Six Figures Off Their Taxes 26:53

1
Q&A: The Tax Strategy Hierarchy Every Small Business Owner Should Know 23:39

1
How Section 831(b) Captive Insurance Protects Your Business and Saves You Taxes 34:02

1
The #1 Retirement Mistake Business Owners Make (And How to Fix It) 36:34

1
Partnership vs. S Corp | How Basis Can Make or Break Your Tax Bill 15:08

1
Don’t Mix Passive and Active Income! Your Entity Structure is Why You're Overpaying on Taxes 23:16

1
Trump’s ‘One Big Beautiful Bill’ Just Changed Your Taxes Forever – What’s Inside 21:00

1
Why Loans Get Denied (Don't Apply for a Mortgage Until You Do This) 31:20

1
Don't Make These EXPENSIVE Mistakes | Mid-Year Tax Checkup 28:16

1
Q&A: Can I Deduct That? From Mileage to Meals, Your Tax Questions Answered 27:01

1
Faith, Leadership, and Stewardship with Reggie Brooks 44:25

1
How to File a Late S Corporation Election and Still Save on Taxes 22:47

1
Do You Need Tax Planning (Spoiler: You Might Be Missing Out) 21:41

1
Want Tax-Free Income in Retirement? Start with a Roth Conversion 19:13

1
Wealth Preservation: Gold & Silver with Dana Samuelson 37:46

1
Business Entity Compliance 101: What You MUST Know 38:25