Reducing Your Tax Burden When Selling Your Business With Crystal Stranger [Ep.148]
Dec 12, 2023
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Crystal Stranger, tax expert for business owners, shares savvy tricks entrepreneurs can use to shrink taxes and pump up profits when selling their businesses. She discusses common tax blunders, the importance of structuring your business to cut down on taxes, and the complexities of sales tax and nexus rules in e-commerce. Crystal also explores the benefits of the qualified small business stock (QSBS) deduction and the difference between stock sales and asset sales. The podcast emphasizes the significance of due diligence in business transactions and recognizing the need for help in growing a business.
Filing taxes annually is crucial for entrepreneurs to maintain compliance and minimize future complications, even for foreign owners of US businesses.
The podcast discusses the tax implications of different entity structures, such as C Corps and LLCs, and emphasizes the importance of considering factors like location and long-term goals when selecting the appropriate structure.
Understanding sales tax and income tax nexus is essential for entrepreneurs, as the varying rules set by different states can lead to complexities and risks for businesses, especially e-commerce ones.
Evaluating the tax implications of asset sales and stock sales is crucial, as asset sales can attract corporate income tax and subsequent dividend tax, while stock sales may offer potential tax advantages for non-US sellers.
Deep dives
Main Ideas and Key Points
The podcast episode discusses various aspects of taxation and how it can impact entrepreneurs. Crystal Stranger, a taxation expert, provides insights on optimizing tax positions and compliance for businesses. She highlights the importance of filing taxes and the potential consequences of not doing so. Crystal also shares information on different entity structures and their tax implications, such as C Corps and LLCs. Furthermore, she discusses hidden growth opportunities in the AI space and offers advice on navigating business taxes.
Importance of Filing Taxes
A key takeaway from the podcast is the significance of filing taxes for entrepreneurs. Crystal emphasizes the importance of filing taxes every year, regardless of income or deductions. She highlights the potential risks and penalties associated with not filing taxes, particularly for foreign owners of US businesses. By stressing the need to fulfill tax obligations, Crystal encourages entrepreneurs to maintain compliance and minimize future complications.
Entity Structures and Tax Considerations
The podcast delves into the different entity structures and their tax implications. Crystal discusses C Corps and LLCs, emphasizing the default treatment of C Corps and the advantages of electing S Corp status. She explains the tax benefits of LLCs for non-US individuals operating businesses outside the US. Crystal also highlights the potential tax advantages of utilizing a C Corp structure and the importance of considering factors like location, founders, and long-term goals when selecting the appropriate entity structure.
Sales Tax Nexus and Income Tax Nexus
Crystal provides insights into sales tax and income tax nexus for businesses. She explains the concept of nexus and the varying rules and thresholds set by different states. Crystal highlights the potential complexities and risks associated with sales tax nexus, particularly for e-commerce businesses. She also touches on income tax nexus and the importance of understanding the tax obligations based on the company's organization and location.
Asset Sales versus Stock Sales
The podcast explores the differences between asset sales and stock sales in terms of tax liabilities. Crystal explains how asset sales can attract corporate income tax and subsequent dividend tax, resulting in a reduced amount for the seller. On the other hand, stock sales can offer potential tax advantages for non-US sellers, as they may be exempt from US tax liability. Crystal highlights the importance of evaluating the tax implications of each type of sale and recommends consulting tax professionals for personalized advice.
Tips for Maximizing Tax Efficiency
The podcast provides tips for maximizing tax efficiency for entrepreneurs. Crystal recommends filing an 83(b) election for C Corps to protect against potential liabilities. She emphasizes the importance of accurate bookkeeping, particularly when it comes to tax preparation. Crystal also advises entrepreneurs to maintain an address in their incorporation state and consistently file all necessary taxes. Finally, she suggests considering reinvestment strategies and tax-friendly expenses, such as marketing, to optimize tax positions.
Conclusion
In conclusion, the podcast episode sheds light on the complexities of taxation for entrepreneurs and offers valuable insights for navigating tax considerations. Crystal Stranger's expertise and advice provide a foundation for understanding the importance of compliance, selecting the appropriate entity structure, and implementing tax-efficient strategies in business operations.
We're back with a brand new episode! ________________________________________
Nothing is certain except death and taxes.As a business owner, taxes are a double whammy—they affect both your personal and business life.
Imagine working hard to build a business that’s set to change your life when you sell it, only to watch taxes eat away at your profits.
Thankfully, there are savvy tricks entrepreneurs can use to shrink taxes and pump up profits when selling their businesses.
That’s where Crystal Stranger comes in. Crystal is the Partner & COO of Cleer Tax, a company that helps US businesses and entrepreneurs navigate their taxes.
In this episode, Crystal joins us to discuss the various strategies entrepreneurs can use to reduce the amount of tax incurred when building and selling their online business.
She unpacks the most common types of taxes that businesses encounter and how to structure your business to cut down on the taxes you have to pay.
Crystal also exposes the big tax blunders many business owners make—like skipping tax filings or setting up shop in high-tax states. According to Crystal,
“A big mistake I see entrepreneurs make is using state addresses for vanity reasons, like having a California or New York address to make their business look established or cool. Some entrepreneurs also sign up for mailing addresses without specifying the location. Putting these addresses on your website, invoices or communications can create large tax liabilities in those states.”
We also dissect the differences between an asset sale and a stock sale, with Crystal explaining how a stock sale can save non-US business owners massive amounts of money!
You might not dodge taxes completely, but armed with the insights from this episode, you can certainly trim your tax bill and safeguard your hard-earned profits!
Topics Discussed in This Episode:
Crystal’s background and how she ended up helping entrepreneurs with tax (02:23)
The most common types of taxes that businesses encounter (06:08)
The differences between LLC and C corp (09:45)
Structuring your exit as an e-commerce business owner (12:23)
How the Nexus tax system works for sales tax (19:26)
The common tax mistakes entrepreneurs make when selling their business (31:09)
Stock sale vs asset purchase (36:14)
The best way to use the proceeds of your sale to grow another business (45:49)
How tax applies to Hold Co businesses (51:14)
How sellers can make their business more attractive from a tax perspective (54:46)