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Should you take the tax deduction today… or build tax-free wealth for tomorrow? In this episode of the Main Street Business Podcast, Mark J. Kohler and Mat Sorensen break down the Roth vs. Traditional IRA debate and explain why the “lower tax bracket in retirement” argument doesn’t always hold up in the real world.
They walk through the math, the mindset, and the long-term strategy behind both options — including inheritance planning, self-directing for higher returns, tax rate uncertainty, flexibility in retirement, and why most entrepreneurs don’t actually earn less in retirement. You’ll also learn how the backdoor Roth IRA works for high-income earners and how to use creative tax strategies to offset Roth conversions.
If you’re rushing to make a last-minute IRA contribution before the tax deadline, this episode could change your decision. Make sure you understand the long-term consequences before chasing a short-term deduction!
You’ll learn:
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=msbp609-traditional-vs-roth-ira
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
We challenge the fear cycle around real estate and show why disciplined contrarian buying can work in 2026. We walk through real multifamily distress, market absorption, and why basis and debt terms now matter more than flashy rent growth.
• rates rising and bridge debt resets driving distress in capital stacks
• absorption trends in Phoenix versus oversupply in Austin and Dallas
• why coastal markets improved due to scarce new supply
• buying stabilized, well‑located multifamily at 30–40% discounts
• fixed agency debt and conservative leverage restoring cash flow
• where single‑family rentals struggle against concessions
• submarket selection and vintage risk to avoid capex traps
• office at deep discounts to replacement and reposition strategies
• timing the cycle with data, not emotion
• our plan to expand beyond Phoenix while staying selective
You can learn more about Jamison and Neighborhood Ventures Here - https://neighborhood.ventures/
Please make sure you are subscribed to the podcast or the YouTube channel where these interviews play as well. Give it thumbs up, five stars, whatever you can do to help spread the good word.
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
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:
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
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
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:
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
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
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:
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
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
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:
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
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
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:
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
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
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:
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
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
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!
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
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
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:
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
Ready to Take the Next Step?
Work With Mat & Mark’s Law Firm
Get 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 Retirement
Want 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 Resources
Mat Sorensen’s Optimal Order of Investing Guide
Learn 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 Guide
Discover practical tax strategies and planning opportunities every business owner and investor should know.
[Download the Free Guide]
Get More From Mat & Mark
Watch on YouTube
Tax strategies, business planning, investing, asset protection, and more.
[Visit the YouTube Channel...
From the publisher's feed
The Main Street Business Podcast, hosted by attorneys Mat Sorensen and Mark J. Kohler, is the go-to resource for entrepreneurs, investors, and business owners who want to build, protect,…
With decades of combined legal and tax experience Mark and Mat make complex financial topics understandable through charismatic discussions and practical education. Their goal is to empower listeners to make smarter legal and financial decisions by turning advanced concepts into clear, actionable strategies for LLCs, corporations, estate planning, tax reduction, raising capital, asset protection, and retirement planning.
Mark J. Kohler is a CPA, attorney, best-selling author of six books, and a nationally recognized authority on small business tax and legal strategies. Mark serves as a Senior Partner at KKOS Lawyers and Board Member at Directed IRA Trust Company, which manages over $3 billion in assets. As the founder of the Main Street Certified Tax Advisor Program, Mark has trained thousands of CPAs and Enrolled Agents nationwide, helping millions of small business owners better navigate tax and legal strategies. Mark also co-hosts The Main Street Business Podcast along with Mat Sorensen.
Mat Sorensen is an attorney, best-selling author of The Self-Directed IRA Handbook, and CEO of Directed IRA & Directed Trust Company, a leading self-directed IRA custodian with nearly $3 billion under administration. He is a national expert on self-directed retirement strategies and a Senior Partner at KKOS Lawyers. Mat also co-hosts The Main Street Business Podcast along with Mark J. Kohler.
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