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 collectibles
• When trusts actually make sense for asset protection—and when they’re an expensive mistake
• Why Social Security has diminishing returns for high earners and how S Corporations change the math
• The rules around depreciated equipment and why you can’t “reset” depreciation with a new entity
• How self-rental real estate strategies can unlock powerful deductions for business owners
• What counts as a prohibited transaction inside IRAs and Solo 401(k)s—and what doesn’t

Get 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-questions

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In this Open Forum episode of the Main Street Business Podcast, Mark J. Kohler and Mat Sorensen tackle real-world tax, legal, and business questions straight from small business owners and investors. From S corporations and QBI deductions to rental real estate, asset protection myths, HSAs, and retirement account strategies, this episode cuts through bad advice and explains what actually works under current IRS rules.

The discussion covers common traps like trying to deduct personal investing as a business, relying on so-called “privacy trusts” for asset protection, and using AI or the IRS hotline for nuanced tax advice. Mark and Mat break down why some strategies are too good to be true, how to properly structure entities across states, and what business owners should focus on in 2026 to build wealth while staying compliant.

If you’re a business owner, investor, or high-income professional looking to understand tax strategies, retirement planning, and asset protection the right way, this episode is packed with practical guidance and hard truths. Subscribe for more expert breakdowns, drop your questions for future open forums, and check out the next episode to keep leveling up your tax and business strategy!

You’ll Learn:

• How S corporations and the QBI deduction really work for small business owners in 2026 — and when they don’t save you money.
• Why treating personal investing as a business deduction is a tax mistake and what you can deduct legitimately.
• The truth about asset protection strategies, “privacy trusts,” and when a holding company structure actually makes sense.
• How to legally pay family members (like your children) through your business and what the IRS expects.
• What the IRS Hot Topics are right now — from HSAs and retirement plans to rental real estate tax benefits.
• How to avoid common pitfalls with solo 401(k)s, HSAs, and mixed-income strategies that cost people real dollars.
• Practical, experience-based answers to real listener questions instead of theoretical or generic advice. 

Get 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=msbp606-open-forum-small-business-strategies-2026 

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Most entrepreneurs set goals every year… and most of them fail to follow through. In this episode of the Main Street Business Podcast, Mark J. Kohler and Mat Sorensen break down their proven, real-world process for building a strategic plan that actually works in 2026 and beyond.

You’ll learn how to think long-term without burning out short-term, why writing your plan down is non-negotiable, and how to reverse-engineer a 10-year vision into realistic one-year action steps. Mark and Mat walk through their exact eight-step framework, covering SMART goals, realistic capacity checks, quarterly execution, accountability, and why sharing your plan with your spouse or board can make or break your success.

If you’re a business owner, investor, or entrepreneur who wants clarity, focus, and momentum this year, this episode gives you a practical blueprint you can implement immediately. Subscribe for more Main Street business strategy, leave a comment with your 2026 goal, and check out future episodes for execution and scaling tactics!

You’ll learn:

• Why most entrepreneurs overestimate what they can do in one year and underestimate what’s possible in ten
• How to create a clear 10-year vision and reverse-engineer it into realistic 5-, 3-, and 1-year goals
• The importance of writing your strategic plan down and why pen-to-paper thinking changes execution
• How to use SMART goals to avoid vague plans that never get finished
• When taking a step back financially is the smartest move for long-term growth
• How to break big objectives into bite-sized, actionable steps you can actually complete
• Why quarterly planning and realistic scheduling matter more than motivation
• How accountability, board meetings, and sharing your plan with your spouse can dramatically improve results
• Why your strategic plan should be flexible, reviewed regularly, and adjusted without guilt

Get 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=msbp605-create-your-annual-strategic-plan

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• Looking to connect with a rock star law firm? KKOS is only a click away!
• Are you ready to get certified in EVERY strategy I teach? Start your journey with a FREE 15-minute discovery call to explore the Main Street Tax Pro Certification.
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Buying a new truck or piece of equipment before December 31 can feel like the ultimate year-end tax hack, but this episode breaks down why that decision can either save you thousands or create a painful tax bill you never saw coming. Mark J. Kohler and Mat Sorensen walk through the real math behind deductions, bonus depreciation, basis, and business-use percentages so you don’t fall into the traps many business owners hit when rushing into a purchase for the write-off. If you’ve ever wondered whether you should buy now, wait, or skip the purchase altogether, this conversation gives you the clarity you need.

You’ll learn how tax brackets, depreciation schedules, and financing choices impact your allowable deduction, why bonus depreciation isn’t always the smartest move, and how S-corp basis affects whether you can deduct anything at all. The guys also explain year-end timing strategies, the time value of money, and how to prioritize deductions that actually move the needle—while avoiding the mindset of treating tax planning like a last-minute school assignment.

If you want to make smart year-end decisions, hit like and subscribe for more practical tax and wealth-building strategies. Have a question about your specific situation? Drop it in the comments! And if you’re considering a major purchase before December 31, watch this episode before heading to the dealership or equipment lot.

You’ll learn:

• How to avoid the biggest year-end tax mistakes business owners make when rushing to buy equipment or a new truck
• Why “just because you can doesn’t mean you should” is the most important rule in year-end tax planning
• The difference between a tax deduction and a tax credit, and why confusing the two leads to expensive decisions
• How to calculate whether a year-end equipment purchase actually saves you money after factoring in your tax bracket
• Why business-use percentage determines whether your vehicle deduction is $100,000 or $30,000
• Why 100% bonus depreciation can become a trap if you finance equipment without having basis in your S corporation
• Why contractors, doctors, and other high-income earners should not automatically take bonus depreciation in one year

Get 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=msbp604-year-end-equipment-purchases

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• You don't want to miss this! Secure your tickets for the #1 Event For Small Business Owners On Main Street America: Main Street 360
• Looking to connect with a rock star law firm? KKOS is only a click away!
• Are you ready to get certified in EVERY strategy I teach? Start your journey with a FREE 15-minute discovery call to explore the Main Street Tax Pro Certification.
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• Craving more content? Check out my Instagram!

These three retirement deadlines before December 31, 2025, could literally double your money overnight, unlock up to $70,000 of Roth contributions, and turn your accounts into a tax-free ATM for your future! In this episode of the Main Street Business Podcast, Mat Sorensen and Mark J. Kohler break down powerful, little-known 401(k) and Roth strategies that most employees and small business owners are completely missing.

You’ll learn how to “match & out” your workplace 401(k) so you don’t leave free employer money on the table, how the Mega Backdoor Roth works using after-tax contributions inside your 401(k), and why high earners and oil rig workers were among the first to exploit it. The guys also cover critical year-end deadlines for setting up a solo 401(k), how to snag valuable small business tax credits, and smart ways to structure Roth conversions so you don’t accidentally bump yourself into a much higher tax bracket. They even touch on using your kids’ earned income to fund their own Roth IRAs and create generational tax-free wealth.

If you want to keep more of what you make, grow your retirement accounts faster, and stop relying on Wall Street or your employer to “save” you, this episode is your year-end checklist.

Listen to the end, then hit subscribe for more tax and wealth-building strategies, drop your questions in the comments, and share this with a friend or family member who needs to take control of their retirement before the year is over!

You’ll learn:

• How to avoid missing the three major retirement account deadlines coming up before December 31, 2025
• Why doing a “match & out” on your employer 401(k) can instantly increase your contributions using free employer funds
• How the Mega Backdoor Roth works inside a 401(k) and why it allows up to $70,000 in Roth contributions
• Why high-income earners, including oil rig workers, were early adopters of after-tax 401(k) strategies
• The exact deadlines and setup requirements for opening and funding a Solo 401(k) for small business owners
• How to use Roth conversions strategically without accidentally jumping into a higher tax bracket
• How to use earned income for your children to fund their own Roth IRAs and create long-term tax-free wealth

Get 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=msbp603-3-year-end-deadlines

• Grab my eBook 30 Unique Strategies Every Business Owner Should Know!
• You don't want to miss this! Secure your tickets for the #1 Event For Small Business Owners On Main Street America: Main Street 360
• Looking to connect with a rock star law firm? KKOS is only a click away!
• Are you ready to get certified in EVERY strategy I teach? Start your journey with a FREE 15-minute discovery call to explore the Main Street Tax Pro Certification.
• Check out our YOUTUBE Channel Here: https://www.youtube.com/markjkohler
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Are you missing out on one of the easiest 100 percent deductions available to business owners? In this episode of the Main Street Business Podcast, Mark J. Kohler and Mat Sorensen break down exactly how to structure a holiday party or company event so it becomes a fully deductible business expense. From the IRS rules under Section 274 to real examples of what qualifies, you’ll learn how to turn food, entertainment, awards, and even venue costs into a legitimate write-off.

Unlike generic tax tips online, this discussion dives into real-world application for small business owners — whether you have a growing team, a handful of employees, or a small staff running from your home office. Mark and Mat explain the three requirements every event must meet, the difference between 50 percent and 100 percent deductions, why culture and team-building matter for tax purposes, and the exact documentation you need to protect the deduction. They also walk through case law, common mistakes, and creative strategies like using the Augusta rule when hosting at your home.

Whether you’re planning a Christmas party, a summer barbecue, a team-building event, or an employee appreciation night, this episode will help you use the tax code to your advantage while still creating an event your team will love. By the end, you’ll know how to design an effective, compliant, and fully deductible company party that strengthens your culture and saves you money.

You’ll learn:

• How to structure a company holiday party or event so it qualifies for a full 100 percent tax deduction
• The three IRS requirements under Section 274 that determine whether meals and entertainment are fully deductible
• Real examples of deductible events, including award lunches, themed parties, off-site gatherings, and interactive team activities
• How to document business purpose properly and protect your deduction if the IRS ever asks for proof
• Creative strategies like using the Augusta rule when hosting at your home to increase deductions legally
• Common mistakes business owners make when planning events — and how to avoid losing the write-off
• How to maximize tax benefits while still creating a memorable, effective event your team actually enjoys

Get 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=msbp602-write-off-holiday-party

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• Looking to connect with a rock star law firm? KKOS is only a click away!
• Are you ready to get certified in EVERY strategy I teach? Start your journey with a FREE 15-minute discovery call to explore the Main Street Tax Pro Certification.
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Are you missing out on some of the most powerful year-end tax strategies available to small business owners and entrepreneurs? In this episode of the Main Street Business Podcast, Mark J. Kohler and Mat Sorensen break down 20 actionable moves you can still make before December 31 to save thousands on taxes and set yourself up for long-term financial success. From retroactive S-corp elections to HSAs, Solo 401(k)s, and smart income timing, this episode is your complete year-end playbook.

Unlike generic tax tips you’ll find online, these strategies are tailored for real entrepreneurs — whether you’re running an LLC, managing rentals, or building your side hustle. Mark and Mat explain how to pay your kids the right way, leverage 100% bonus depreciation on vehicles and equipment, and take advantage of HRAs, Roth conversions, self-rental rules, and tax-loss harvesting before the clock runs out. They also share which moves are still possible after year-end and which deadlines you can’t afford to miss.

Whether you’re just getting started or already running a profitable business, this episode will help you keep more of what you earn and make smarter tax decisions for 2025. By the end, you’ll know exactly how to finish the year strong — and start the next one with a strategy that builds wealth, not stress.

If you’re serious about saving money, staying compliant, and maximizing every deduction possible, this is an episode you can’t afford to skip!

• How to implement 20 year-end tax strategies that help business owners, investors, and the self-employed keep more of their money
• How to use S corporation elections, payroll planning, and paying your children legally to reduce self-employment tax
• Why HSAs, HRAs, and Solo 401(k)s are some of the most powerful tools for deductible medical and retirement planning
• How to unlock startup deductions with a first sale and maximize write-offs through year-end equipment and vehicle purchases
• Smart ways to shift income and expenses between tax years to optimize your tax bracket
• How Roth conversions, rental real estate strategies, and the self-rental rule build long-term tax-efficient wealth
• Why scheduling a personalized tax review ensures that these strategies are actually implemented before December 31

Get 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=msbp601-20-year-end-tax-strategies

• Grab my eBook 30 Unique Strategies Every Business Owner Should Know!
• You don't want to miss this! Secure your tickets for the #1 Event For Small Business Owners On Main Street America: Main Street 360
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• Are you ready to get certified in EVERY strategy I teach? Start your journey with a FREE 15-minute discovery call to explore the Main Street Tax Pro Certification.
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conversation with bestselling author and negotiation expert Rebecca Zung and attorney Mark J. Kohler. We break down what to do first, what to avoid, and how to protect your future — without playing dirty.

You’ll learn the five main areas courts consider in family law cases—property division, spousal support, custody and parenting decisions, child support, and attorney’s fees—and how each one affects the next. We cover business valuation timing, enterprise vs. personal goodwill, forensic accounting, lifestyle analysis, and “sudden income deficiency syndrome.” Plus, Rebecca explains her SLAY framework (Strategy, Leverage, Anticipate, You) for negotiating with narcissists and staying out of emotional sabotage.

If this helped, subscribe for weekly legal and tax strategy insights, drop your questions in the comments, and share with a friend who needs it.

You’ll learn:

• How to prepare financially before filing for divorce — and the first critical steps to protect your assets and credibility
• The five main areas every family law case covers: property division, spousal support, custody and parenting decisions, child support, and attorney’s fees
• How and when to value a business during divorce, including the difference between enterprise and personal goodwill
• Why forensic accounting, lifestyle analysis, and “sudden income deficiency syndrome” can make or break your case
• Smart strategies for both the moneyed and non-moneyed spouse to stay financially stable during proceedings
• How Rebecca Zung’s SLAY framework (Strategy, Leverage, Anticipate, You) helps you negotiate with a narcissist and avoid emotional traps

Get 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=msbp600-rebecca-zung-interview 

• Grab my eBook 30 Unique Strategies Every Business Owner Should Know!
• You don't want to miss this! Secure your tickets for the #1 Event For Small Business Owners On Main Street America: Main Street 360
• Looking to connect with a rock star law firm? KKOS is only a click away!
• Are you ready to get certified in EVERY strategy I teach? Start your journey with a FREE 15-minute discovery call to explore the Main Street Tax Pro Certification.
• Check out our YOUTUBE Channel Here: https://www.youtube.com/markjkohler
• Craving more content? Check out my Instagram!

Recorded live at the Alt Asset Summit in Phoenix, this episode of the Main Street Business Podcast brings you a high-energy, audience-fueled breakdown of the Top 10 Due Diligence Must-Dos Before You Put Money Anywhere.

Join hosts Mark J. Kohler and Mat Sorensen as they share stories from the trenches of asset protection, investing mistakes, client war stories, and lessons from 10,000+ hours advising entrepreneurs, investors, and small business owners. From understanding what you’re investing in, to the dangers of pressure tactics, to CRUTs and crypto, to structuring a Solo 401(k) the right way—they cover it all.

What You’ll Learn:

• The #1 rule Warren Buffett follows—and why you should too
• Why “I don’t buy hype, I sell it” could save your portfolio
• Legal pitfalls of raising money and kickback commissions
• How to use a CRUT (Charitable Remainder Unitrust) for crypto gains
• Real client horror stories involving napkin contracts and pressure to invest
• Solo 401(k) strategy stacking and the Side Door 401(k)
• The difference between building wealth and preserving it
• Why saying “No” is a power move for every investor

Plus: Live Q&A with audience members on Roth contributions, estate planning, and real-world investing scenarios.

• Grab my eBook 30 Unique Strategies Every Business Owner Should Know!
• You don't want to miss this! Secure your tickets for the #1 Event For Small Business Owners On Main Street America: Main Street 360
• Looking to connect with a rock star law firm? KKOS is only a click away!
• Are you ready to get certified in EVERY strategy I teach? Start your journey with a FREE 15-minute discovery call to explore the Main Street Tax Pro Certification.
• Check out our YOUTUBE Channel Here: https://www.youtube.com/markjkohler
• Craving more content? Check out my Instagram!

In this episode of the Main Street Business Podcast, Mark J. Kohler and Mat Sorensen break down why every small business owner should hold their annual Family Board Meeting before the end of the year. This powerful meeting isn’t just a formality — it’s a proven strategy to strengthen your business, protect your assets, and educate your family about wealth and responsibility.

 You’ll learn how to make your Family Board Meeting IRS-compliant, maximize write-offs, document your decisions properly, and create a legacy plan that keeps your business and family aligned for years to come. Mark and Mat share real examples, step-by-step guidance, and practical insights to help you get it done right before December 31st.

 Don’t wait until tax season to get organized — plan your Family Board Meeting now and take control of your financial future!

You’ll learn:

• How to structure and hold your Family Board Meeting before year-end to stay compliant and maximize tax benefits
• The 7 key reasons every business owner needs an annual Family Board Meeting — from asset protection to financial education
• How to properly document your meeting minutes so your business stays audit-proof with the IRS
• Smart ways to include your spouse and kids in your business legally — and teach them real-world wealth principles
• What expenses you can write off when holding your Family Board Meeting, including travel and meeting costs
• How this meeting supports your business continuity plan and legacy goals for future generations
• Simple steps to get your Family Board Meeting done before December 31st — and set your business up for long-term success

Get 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=msbp598-family-board-meeting-by-year-end

• Grab my eBook 30 Unique Strategies Every Business Owner Should Know!
• You don't want to miss this! Secure your tickets for the #1 Event For Small Business Owners On Main Street America: Main Street 360
• Looking to connect with a rock star law firm? KKOS is only a click away!
• Are you ready to get certified in EVERY strategy I teach? Start your journey with a FREE 15-minute discovery call to explore the Main Street Tax Pro Certification.
• Check out our YOUTUBE Channel Here: https://www.youtube.com/markjkohler
• Craving more content? Check out my Instagram!