Choosing the right business entity is one of the most important tax planning decisions self-employed clients and small business owners will make. The difference between operating as a sole proprietor, LLC, S corporation, or C corporation can significantly impact self-employment taxes, deductions, payroll requirements, retirement planning opportunities, and overall tax liability.

In this practical and example-driven webinar, Jason Dinesen explains how entity selection decisions affect real-world tax outcomes. Through detailed case studies and income-based comparisons, participants will explore how different entity structures may create planning opportunities or unexpected tax consequences, depending on the client’s financial situation.

This webinar is designed specifically for tax professionals who advise self-employed individuals, independent contractors, freelancers, consultants, and small business owners. Participants will gain a clearer understanding of how entity taxation works, when S corporation elections may make sense, and why a C corporation may occasionally provide advantages for certain clients.

The webinar also explains the role of LLCs in tax planning and addresses one of the most common misconceptions among business owners: forming an LLC does not automatically reduce taxes. Attendees will learn how LLCs are treated for federal tax purposes and how entity elections can change taxation outcomes.

In addition to tax planning considerations, Jason discusses why entity selection should often involve collaboration with attorneys and legal professionals. While tax advisors can analyze the tax implications of entity choice, liability protection, and legal structure decisions may require separate legal guidance.

Using real-world examples, this webinar helps tax professionals improve client conversations, identify planning opportunities, and better evaluate entity strategies for the 2026 tax season and beyond.

This webinar counts for 2 Hours of Federal Tax Law for IRS Continuing Education. 

Learning Objectives

By attending this webinar, participants will be able to:

• Understand what “entity selection” means in tax planning
• Identify the major types of business entities and how they are taxed
• Explain how LLCs fit into entity planning strategies
• Compare tax outcomes between sole proprietorships, LLCs, S corporations, and C corporations
• Evaluate how income levels affect entity planning decisions
• Identify when S corporation elections may provide tax advantages
• Recognize situations where a C corporation may make sense
• Understand the importance of legal considerations in entity selection planning

Frequently Asked Questions

What is entity selection in tax planning?

Entity selection refers to choosing the legal and tax structure a business operates under, such as a sole proprietorship, LLC, S corporation, or C corporation. The structure chosen can affect taxation, self-employment taxes, deductions, liability considerations, and long-term planning opportunities.

What is the difference between an LLC and an S corporation?

An LLC is a legal entity created under state law, while an S corporation is a federal tax election. An LLC can choose to be taxed as a sole proprietorship, partnership, S corporation, or C corporation, depending on the situation.

When does an S corporation make sense?

An S corporation may provide tax savings for certain profitable businesses by potentially reducing self-employment taxes. However, the benefits depend on income level, payroll requirements, administrative costs, and the client’s overall financial situation.

Is a C corporation ever a good choice for small business owners?

In some situations, yes. A C corporation may provide advantages involving retained earnings, fringe benefits, or future business growth strategies. This webinar explores examples where a C corporation could make sense.

Does forming an LLC automatically lower taxes?

No. Many business owners misunderstand this concept. An LLC alone does not automatically change federal taxation. Tax treatment depends on how the entity is classified or elected for tax purposes.

Who should attend this webinar?

This webinar is designed for tax professionals, tax preparers, enrolled agents, CPAs, and advisors who work with self-employed individuals and small business owners.

Will this webinar include real-world examples?

Yes. Much of the webinar is built around case studies and numerical comparisons that demonstrate how tax outcomes vary based on entity type and business income.

Why is entity selection important for self-employed clients?

The wrong entity choice can increase taxes, reduce planning flexibility, or create unnecessary administrative burdens. Understanding entity selection helps tax professionals better guide clients through important financial decisions.

 About the presenter:

Jason Dinesen (EA, LPA) is a tax nerd, entrepreneur, tax expert, and a well-known presenter of continuing education courses. 

Known for his sharp tax interpretations, he is one of the quickest to bring the analysis of the latest tax updates and IRS guidance to the professional community. Jason has coached over 200,000 accounting, tax, and HR professionals on various topics of accounting, individual taxation, corporate taxation, professional ethics, and much more. 

He has presented dozens of webinars on Form 1099 (for 10 years on this subject!), marriage in the tax code, tax updates, the new Form W-4, payroll updates, filing status, tax credits, corporation and partnership taxation, and other issues relating to the modern-day setting.