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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 you’re building or investing in startups, this could be the single most powerful tax break you’ll ever use.

🚀 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) How Founders Pay $0 in Taxes With QSBS

The “greatest tax exemption that exists” and why startup founders need to know it.

(00:48) What is QSBS and Who Qualifies

Key rules, industries that benefit, and those excluded (law firms, banks, services).

(03:30) Can LLCs and S Corps Still Benefit?

How to flip into a C Corp, restart the clock, and unlock bigger gains.

(06:05) Real Example: $126M of QSBS Eligibility

How flipping from LLC to C Corp can multiply your tax-free exclusion.

(08:10) New Rules From the Big Beautiful Bill and Why States Matter

Exclusion raised to $15M, partial exclusions after 3–4 years, and $75M asset threshold, plus, which states recognize QSBS?

(15:00) Don’t Be Too Early, Don’t Be Too Late

The timing mistakes founders make when setting up QSBS.

(18:30) Stacking QSBS With Trusts

How Get Dynasty helps founders create trusts for $40M+ in tax-free gains.

(23:00) Avoiding Common Mistakes

Why planning early is critical and why TikTok tax tips miss the bigger picture.

(27:30) Success Stories: Roblox and Beyond

How founders have shielded $40M–$120M from taxes using QSBS trusts.

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

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 framework for worker classification, the red flags that trigger audits, and the tax differences between employees and contractors. You’ll learn how to protect your business, avoid costly penalties, and even find tax strategies that benefit both employers and contractors.

👉 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:
(00:16) Why Misclassification Is a Major IRS Red Flag
When workers are incorrectly classified as contractors instead of employees, the employer becomes responsible for unpaid payroll taxes, Social Security, Medicare, unemployment taxes, plus penalties and interest.

(04:01) What Triggers an IRS Audit
Unemployment claims and disgruntled workers are the two most common red flags.

(05:43) The IRS 3-Factor Test
Worker status is based on behavioral control, financial control, and the overall relationship.

(09:47) Signs of an Employee vs Contractor
Clear examples that distinguish W-2 employees from 1099 contractors.

(12:29) Tax Treatment of Each Worker Type
How payroll taxes, reporting, and deductions differ between W-2s and 1099s.

(15:22) Practical Tips for Staying Compliant
Contracts, scope of work, and how to defend your classification in an audit.

(16:31) Tax Strategies for Employers
How hiring employees changes access to tools like the Solo 401(k).

(17:08) Tax Strategies for Contractors
Turning a 1099 gig into a business with deductions, retirement plans, and S Corp elections.

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 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 strategically in your business 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:

(01:34) What Is US Energy and Their Focus
US Energy’s 45+ year history in oil and gas, working with partners like Exxon and Shell, and why the Permian Basin is the hottest U.S. play.

(04:01) The Tax Benefits of Drilling Funds
IRS Code 263(c) allows investors to deduct 85–90% of their investment upfront through intangible drilling costs.

(06:07) Tangible Costs and Depletion Allowances
Using depreciation and depletion to shelter future income from wells and create long-term tax efficiency.

(08:12) Why Oil and Gas Beats the “Buy a Truck” Strategy
Instead of wasting money on deductions you don’t need, oil and gas offers upfront write-offs and produces an appreciating income-generating asset.

(09:24) Sample Investment Return Breakdown
How a $100,000 investment could produce $45,000 in tax savings and cash flow returns of 1.5–2x over 10 years.

(13:06) Understanding Tax Risk
Audit concerns, excess business loss limitations, and AMT caps, plus how unused deductions can be carried forward.

(18:28) Investment Risks and Hedging Commodity Prices
The difference between exploratory, step-out, and developmental drilling, and how hedging protects against oil price drops.

(22:06) Oil and Gas for QBI Planning
How investments can lower AGI and re-open the Qualified Business Income deduction, creating stacked tax savings.

👉 Learn more about Oil and Gas Investing at US Energy: https://www.usenergyco.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

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.

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 demo call today! Click here or visit: https://taxelm.com/demo/

Chapters:

(01:06) What Is Basis and Why It Matters
Your basis determines how much you can take out of your business tax-free and how much loss you can deduct.

(01:44) Client Story: The $7K Surprise Tax Bill
A business owner thought their S Corp distributions were tax-free—until a capital gains bill showed up.

(02:23) Calculating Basis: Partnership vs. S Corp
Mike walks through the formula for both. Spoiler: only partnerships include debt in basis.

(06:20) Real-Life Example: Same Business, Different Outcome
Two identical businesses. One pays capital gains, the other doesn’t. The difference? Entity type.

(07:44) Why Basis Gets Miscalculated
Loans, poor bookkeeping, and switching accountants are common culprits behind basis errors.

(09:25) Planning Tips to Avoid Basis Mistakes
Track your basis annually, keep clean books, adjust distributions, or structure shareholder loans when needed.

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

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 slashing self-employment tax, this is the blueprint smart business owners use to keep more of what they earn.

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

Chapters:

(01:04) Active vs. Passive Income (Why separation matters)
Why it's important to keep your active business and passive investments in separate entities.

(04:06) Choosing the Right Entity Type
Mike explains when to use sole proprietorships, LLCs, S corps, and C corps, depending on your needs.

(10:55) The S Corp Holding Company Setup
How to simplify taxes and planning by running your active businesses through one S-Corp holding company.

(14:36) Special Structures for Tax Strategies
When to use a sole proprietorship or C corp for things like hiring kids or unlocking health reimbursements.

(15:16) Real-Life Use Cases and Examples
Mike walks through examples for coaches, rental properties, and software businesses using strategic entities.

(21:16) When to Create a New Entity
Key questions to ask when deciding whether to form a new LLC, DBA, or use an existing structure.

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.