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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.

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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.