The Biggest Tax Planning Mistakes Business Owners Will Regret in 2026 with Mark J. Kohler

Dec 17, 2025

Mark J. Kohler, an attorney and tax strategy expert, dives into crucial tax planning insights for business owners. He highlights a common mistake: the gap between knowing tax strategies and actually applying them. Mark explains true self-direction in retirement accounts and the range of investments allowed, from real estate to crypto. He discusses the importance of quarterly planning sessions and warns about the risks of prohibited transactions. Listeners will gain valuable tips to enhance their tax savings before 2026.

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ADVICE

Quarterly Planning And Accountability

Hold quarterly planning sessions with your tax advisor and review implementation and bookkeeping together.
Fire advisors who resist implementing agreed strategies and take ownership as the business owner.

INSIGHT

True Meaning Of Self-Directed

'Self-directed' on Wall Street usually means trading within the broker's limited platform, not true alternative investing.
Real self-direction lets you move accounts to custodians that permit real assets like real estate, crypto, and private businesses.

ADVICE

How To Gain Self-Directed Control

Roll old 401(k)s into IRAs or use backdoor Roths to gain self-direction regardless of income.
Your current employer 401(k) typically locks you into the plan's broker until you leave or set up your own self-directable plan.

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Do you really have your tax planning handled? The thing is, many business owners are making a critical mistake that will become even more expensive by 2026.

In this episode, Mike Jesowshek, CPA, sits down with Mark J. Kohler to expose the biggest tax planning failure business owners make. Confusing knowing strategies with actually applying them. Mark explains why tax savings disappear at the implementation level, how poor execution creates long-term consequences, and why retirement accounts are one of the most overlooked areas where this mistake shows up.

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Chapters

(01:02) Why Most Tax Strategies Never Get Implemented
Many business owners think they are doing tax planning, but when you look at their tax return, the strategies are missing.

(03:05) Tax Strategy vs Tax Compliance
There is a major disconnect between tax advisors and tax preparers.

(05:18) What “Self-Directed” Really Means
Wall Street uses the term self-directed loosely. Mark explains the real definition and why traditional brokers do not promote it.

(07:04) What You Can Invest in With a Self-Directed IRA
Real estate, private businesses, lending, crypto, precious metals, and more. Mark walks through the types of investments retirement accounts are legally allowed to own.

(09:36) Prohibited Transactions and IRS Red Flags
It is not about prohibited assets. It is about prohibited people and personal benefit.

(12:02) Can You Be Active in Retirement-Owned Investments
You can make decisions, write checks, and structure deals, but you cannot personally perform labor or manage properties.

(14:01) Cost and Setup of a Self-Directed IRA
Many people assume self-directing requires hundreds of thousands of dollars.

(15:52) Employer 401ks vs Self-Directed Plans
Why most employer-sponsored 401ks restrict your options and how entrepreneurs can set up plans that allow true self-direction.

(18:06) When Self-Directed IRAs Are Not a Good Fit
Self-directing requires time, focus, and discipline. Mark explains when investors should wait or choose simpler options.

(19:33) How to Get Started the Right Way
Education comes first. Mark shares resources, podcasts, books, and next steps for learning before investing.

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🎙 ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.