The Main Street Business Owner’s "Situation Room"

Your Strategic Command Center for Smarter Decisions.

Get real answers from the nation’s top tax and legal strategist—trusted by over 10,000 business owners nationwide. Your membership includes:

Biweekly live strategy sessions with Mark to tackle your toughest business, tax, and legal questions in real time.
A self-paced business course designed to guide you step-by-step through the foundations of smart business ownership—from structure to scaling.

Finally, the clarity, confidence, and expert support you need to grow and protect your business—all in one place.

Where Do You Go When Your Business Hits a Critical Moment?

Every leader needs a command center—and business owners are no exception. The Business Owner "Situation Room" is your virtual HQ for navigating tough decisions, solving complex problems, and planning your next move. Just like the president of the United States has a situation room and captains of ships have a bridge as a command center, you need a trusted space to access expert insights, collaborate with peers, and get answers fast—especially when the stakes are high. Whether you’re in growth mode or preparing your exit, this is where clarity begins.

Made for Real Business Owners

From first-time founders navigating unknowns to growth-stage entrepreneurs wanting to scale and seasoned business owners preparing to exit...this path is designed for anyone who has experienced the following:

Your lawyer says, “Ask your accountant.”
Your accountant says, “Ask your lawyer.”
You don’t even know what questions to ask—or who to trust.

This is your go-to source for real-time answers—without the runaround, confusion or outside noise.

The 4 Phases of Every Business Owner’s Journey

40 Essential Questions Every Business Owner Should Know

Whether you’re launching, growing, or preparing to exit, the Business Owner Situation Room equips you with 40 must-ask questions - 10 for each stage of the business lifecycle. These are the legal, tax, and strategic questions most business owners don’t even know they should be asking—until it’s too late.

Stay ahead. Make smarter decisions. Build with confidence.

Phase 1: Start-Up & Structure, with the Foundation to Launch

You’re in the "Start-Up phase", equal parts fear, excitement, and uncertainty. One minute you’re thinking, “What have I done?” and the next, “This is a freaking awesome idea.” You’re wrestling with big questions: Is this viable? What entity should I choose? How do I raise capital and structure it correctly? Who do I need on my team? And how long will I stay in this phase? It’s messy and emotional — but it’s exactly where every successful business begins.

What type of entity should I set-up and use for my business?
Should I bring on partners or investors, and what are my options for raising capital and structuring it properly?
How do I properly register my business and ensure I meet all legal requirements, including any necessary licenses and permits for my industry and location?
What are the options and legal requirements for hiring employees versus independent contractors?
Should I set-up in Wyoming or some other State?
What are the steps in buying a business and any important pitfalls?
What does “start-up mode” mean from a tax perspective, and how do I know which expenses are deductible and how to document them properly?
How can I protect my privacy on company filings, and what are the best practices for choosing a registered agent, company address, and other official positions?
Should I list my spouse or other family members as an owner of the business and what role should or can they play in the business?
How do I pay myself and which bookkeeping system should I use, and what about business credit?

Phase 2: Operate and Optimize: Saving Taxes and Reducing Legal Exposure

You’re making some money now, but you’re not sure you’re doing it right. You’re juggling everything and trying to systemize the business because there’s only one of you. How do you keep taxes, your biggest expense, under control? How do you pay yourself and involve your family the right way? With asset protection and contracts to manage, it can feel like it’s all bearing down at once. This phase is about gaining control, building smarter systems, and creating a business that works for you rather than running your life.

What are the easiest tax write-offs I should be taking advantage of?
Explain more about when to convert to an S-Corporation and how do I determine my salary level for years to come?
How do I strategically pay my family members, such as my spouse, my minor or adult children, even my parents, or grandchildren?
What are the top 10 business contracts I should be using and make sure they are up to date?
Should I own or rent a business location?
What are my options to write off medical expenses and keep my costs down at the same time?
What are the asset protection procedures I should be using and do I need an Estate Plan?
What financial data, statements, and ratios should I be gathering and tracking, and which Key Performance Indicators are the most important for my business?
What retirement account should I be starting with if any at this stage of my business?
If I have debt that’s holding me back, what are my options and how does the Debt Snowball strategy work?

Phase 3: Grow and Scale: Saving, Investing, & Building Real Wealth

“Developing people, creating vision, and becoming a leader.” Things are working. Revenue is strong, the business has momentum, and now the questions shift. Where should I invest the profits? How do I protect what I’ve built? How do I scale without breaking what’s working? You have the drive and the opportunity to push hard while the window is open, but you’re experienced enough to know one bad move can be costly. This is the phase where you step into real leadership, implement advanced tax strategies, and turn income into long-term wealth.

What are some advanced tax write-offs I should be aware of, and when do I use them?
How much of my profits should I be reinvesting back into my business, and what are the risks and rewards of redeploying that money elsewhere?
What are the benefits and most common strategies for investing in rental real estate, and should I do that instead of a retirement account?
What does retirement plan optimization consist of if I’m ready to really put away some money, and how do I structure it properly if I have full-time employees?
What is self-directing, why doesn’t my investment advisor talk about it, and what can my retirement plan truly invest in?
What is an estate plan, and can I get away with a simple will?
What are the best college savings strategies, and how can I help my older children launch?
What are the best ways to scale my business and develop people?
What role should life insurance play in my overall investment and asset protection strategy, or even my retirement plan?
If I’m getting divorced, what practical tax advice should I know when working with divorce attorneys?

Phase 4: Exit and Legacy: Preparing for Sale and Business Continuation Plans

“Replacing yourself and creating a sustainable business that doesn’t require you.” You’ve built something real, but you know you can’t or don’t want to keep this pace forever. Now the questions get bigger. Will I have enough for retirement? How do I exit without losing what I’ve worked so hard to build? What will it cost me in taxes? How do I protect my business, assets, and property, and make sure my estate plan reflects the legacy I want to leave? This phase is about creating options, securing your future, and building a transition plan that protects both your wealth and your family.

How do I prepare my business for sale and valuation, and what is EBITDA and why is it so important?
What are the steps involved in selling a business, and what legal issues do I need to consider?
What are the five best tax strategies when selling a business, and what’s the difference between a stock sale and an asset sale (QSBS, installment sale, CRT, 1031 exchange, opportunity zones)?
What practical issues should I consider if I want to sell or transfer my business to family members, key employees, or both?
What is a business continuation plan or buy-sell agreement, and how do I integrate it into my estate plan?
What are some practical strategies for navigating Social Security and Medicare while building wealth?
Should I pay off my personal residence, and how do I protect it from a lawsuit?
What state tax planning ideas should I consider if I plan to retire and domicile in a different state?
What’s your final advice on building wealth, managing it, and protecting it?
What are the 5 best ways to leave a legacy and impact future generations?

A Complete System to Build a Better Business

The training gives you tools, education, and a trusted network to help you:

Lower your taxes legally and proactively
Protect your assets with smart entity structuring
Organize your finances for maximum profitability
Get access to the pros Mark J. Kohler personally endorses
Plug into a growing community of high-achieving owners

Join the Program

America's #1 Tax & Legal Expert

Mark J. Kohler is a CPA, attorney, national speaker, and YouTube educator with over 35,000,000+ views. For over 25 years, he’s trained professionals and business owners to work smarter — instead of harder.

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Strong community of driven professionals sharing clients, referrals, and big wins—together.

$ 1 B

Saved in taxes by business owners through real-world strategy and smarter structure.

Maximize Write-Offs & Stay Compliant

$2,995 $995

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Includes 1 month of membership ($99 value)
7-Day Money-Back Guarantee

More Than a Course — It's a Movement

As a Main Street Business Owner, you gain access to exclusive events and coaching designed to help you connect with other high-level entrepreneurs, get direct insights from Mark and his team, and stay focused on the next big goal for your business.

40+ Expert Video Answers
2x Monthly LIVE Firesides with Mark J. Kohler
Private Business Owner Community Access

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Success Stories From
the Main Street Community

“Before becoming certified, I felt lost and overworked. Now, I’m saving thousands in taxes and growing with confidence.”

Peter F. CPA

“Mark’s training helped me restructure everything. It changed my mindset — and my bottom line.”

Craig M. Small Business Owner

“The masterminds alone are worth the price. I finally feel like a real CEO.”

Tiffany C. Entrepreneur

Real Training for Real Business Growth

Inside the training, you’ll learn how to:

Structure your business the right way from day one—LLC, S-Corp, or C-Corp
Maximize write-offs, build a smart tax strategy, and budget for growth
Maintain legal protection with privacy tools, minutes, and compliance practices
Hire, market, and scale with confidence using advanced business strategies
Exit your business profitably—reduce taxes, preserve wealth, and plan your legacy

Key Benefits

Trusted answers from a seasoned CPA/Attorney
Two (2) Business Owner Mastermind Sessions EVERY month LIVE with Mark Kohler in REAL TIME, as he answers pre-vetted questions from the business owners in the Program
Confidence at every stage of your business journey
Community Forum of business owners who are current monthly members of the program
Resource library
Affordable, actionable, and designed for YOU

Ready to Scale Your Business?

16+ Hours of Expert-Led Training
A dashboard and space with 40 of the most frequently asked questions answered, organized in 4 phases of a business’s lifecycle.
Live Mastermind Sessions (Biweekly)
Business Owner Mastermind Sessions LIVE with Mark Kohler, as he answers pre-vetted questions from the business owners in the Program.
Full Access to Past Trainings + Replays
Explore a growing library of real-life strategies and implementation tips.
Downloadable Tools & Templates
Includes payroll matrix, debt snowball calculator, and more.
Welcome Box + 3 Books
Get Mark J. Kohler’s best-selling guides delivered to your door.
Community Forum
Resource library and community of business owners