Business Owner’s "Situation Room"
Your Strategic Command Center for Smarter Decisions.
The ''Situation Room'' is your command and control center as a business owner. A place to tackle complex decisions, access trusted tax and legal strategy, and collaborate with others as you navigate all stages of business from startup to exit.
Made for Real Business Owners
Mark has created an online portal to get quick answers to difficult questions and a bi-weekly Mastermind to get additional support:
- It's no longer impossible to get information from a real tax lawyer focused on small business.
- Get advice affordably before making a one-on-one appointment.
- Network with other like minded business owners
- And...IT'S AFFORDABLE!!!
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
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 to ensure compliance, and how do I determine which licenses and permits are required for my industry and location?
- What are the legal requirements and considerations when hiring employees versus independent contractors?
- Should I set up my business in Wyoming or another state?
- What are the steps involved in buying a business, and what important pitfalls should I avoid?
- From a tax perspective, what does start-up mode mean, which expenses are deductible, and how should I document them properly?
- How do I protect my privacy on company filings, and what should I consider regarding a registered agent, company address, and other official positions?
- Should I list my spouse or other family members as owners, and what role should they play in the business?
- How should I pay myself, which bookkeeping system should I use, and how do I properly build and manage 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.
- What are the easiest tax write-offs I should be taking advantage of?
- When should I convert to an S-Corporation, and how do I determine my salary level for years to come?
- How do I strategically pay family members such as my spouse, minor or adult children, parents, or even grandchildren?
- What are the top 10 business contracts I should be using, and how do I make sure they stay 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 asset protection procedures should I be using at this stage of the game?
- What are the critical steps in optimizing my business, and what are the most important Key Performance Indicators (KPIs) to track?
- 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?
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.
Learn more about us
Maximize Write-Offs & Stay Compliant
$2,995
- Includes 1 month of membership ($99 value)
- 7-Day Money-Back Guarantee
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
$2,995
$99/mo for Membership
Includes bi-weekly Masterminds with Mark Kohler, Community Forum, with Forms and Resources.
7-Day Money-Back Guarantee
Scale. Profit.
Thrive. Anywhere.
Download the Main Street Professionals app to hold expert coaching, high-level strategies, a supportive network in the palm of your hands.
