#607 Open Forum — Tax Expert Answers Your Most Difficult Tax & Legal Questions! episode artwork

EPISODE · Jan 30, 2026 · 31 MIN

#607 Open Forum — Tax Expert Answers Your Most Difficult Tax & Legal Questions!

from Main Street Business · host Mark J Kohler and Mat Sorensen

Are you making smart tax and legal decisions, or leaving money on the table without realizing it? In this episode of the Main Street Business Podcast, Mark J. Kohler tackles your toughest questions and breaks down real-world tax strategies, asset protection myths, and retirement planning mistakes that business owners and investors face every day.From selling million-dollar collectibles and avoiding unnecessary taxes, to understanding how S Corporations can impact Social Security benefits later in life, Mark tackles listener questions with practical, no-nonsense advice. You’ll learn why LLCs don’t magically reduce taxes, how charitable remainder trusts really work, and when trusts actually make sense — and when they’re a complete waste of money.If you’re a small business owner, investor, or high-income professional looking to legally reduce taxes, protect assets, and build long-term wealth, this episode is packed with insights you can use right now!You’ll learn:Why setting up an LLC or corporation won’t help you avoid capital gains taxes when selling high-value collectiblesWhen trusts actually make sense for asset protection—and when they’re an expensive mistakeWhy Social Security has diminishing returns for high earners and how S Corporations change the mathThe rules around depreciated equipment and why you can’t “reset” depreciation with a new entityHow self-rental real estate strategies can unlock powerful deductions for business ownersWhat counts as a prohibited transaction inside IRAs and Solo 401(k)s—and what doesn’tGet a comprehensive tax consultation with one of our Main Street tax lawyers that can build a tax strategy plan with an affordable consultation that will leave you speechless!! Here’s the link - https://kkoslawyers.com/services/comprehensive-bus-tax-consult/?utm_source=buzzsprout&utm_medium=description-link&utm_campaign=main-street-business-podcast&utm_content=msbp607-open-forum-toughest-tax-and-legal-questionsReady to Take the Next Step?Work With Mat & Mark’s Law FirmGet strategic legal guidance for your business, taxes, asset protection, and estate planning with KKOS Lawyers.[Book a Call with KKOS Lawyers]Take Control of Your RetirementWant to invest your IRA or 401(k) in assets you actually understand? Check out our self-directed trust company Directed IRA.[Learn More About Directed IRA]Free ResourcesMat Sorensen’s Optimal Order of Investing GuideLearn how to prioritize where your money should go and build a smarter investing strategy.[Download the Free Guide]Mark J. Kohler’s 30-Point Tax GuideDiscover practical tax strategies and planning opportunities every business owner and investor should know.[Download the Free Guide]Get More From Mat & MarkWatch on YouTubeTax strategies, business planning, investing, asset protection, and more.[Visit the YouTube Channel...

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Are you making smart tax and legal decisions, or leaving money on the table without realizing it? In this episode of the Main Street Business Podcast, Mark J. Kohler tackles your toughest questions and breaks down real-world tax strategies, asset protection myths, and retirement planning mistakes that business owners and investors face every day. From selling million-dollar collectibles and avoiding unnecessary taxes, to understanding how S Corporations can impact Social Security benefits la...

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#607 Open Forum — Tax Expert Answers Your Most Difficult Tax & Legal Questions!

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