Exit Planning Tools for Business Owners

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The 3% Problem in Advisory Work: A Guide for Business Owners

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As a business owner, you belong to a unique group that makes up only 3% of the population. Yet, many advisors treat you like any other client—using the same approaches they apply to executives, professionals, or retirees. This is a fundamental misunderstanding that can impact your business and personal goals.

Why You’re More Than Just an Asset

You are not simply a high-income individual with concentrated wealth. Your business is not just an investment; it’s an integral part of your identity, your livelihood, and your daily purpose. It is the source of your authority, reputation, and even your personal satisfaction.

Navigating Identity, Not Just Assets

When traditional clients seek advice, the focus tends to be on optimizing their assets. In contrast, advising business owners like you involves navigating a complex web of identity and emotional attachment. This distinction is crucial and affects how you engage with advisors.

Understanding the Owner’s Perspective

The Structure of Your Business

Unlike executives who operate within established frameworks, you are the architect of your business’s structure. If a senior executive makes a mistake, it usually impacts their bonus. But for you, a misstep could jeopardize payroll, credit lines, or even your family’s financial security.

This creates a protective and cautious mindset that many advisors fail to recognize. Your business is not just an income engine; it’s something you’ve built, defended, and refined over years. Every employee, system, and brand element bears your imprint.

The Impact of Structural Suggestions

When an advisor casually suggests changes, it can feel less like strategy and more like criticism. Understanding this emotional landscape is vital; without it, you may resist recommendations that could genuinely benefit your business.

The Challenge of Decision-Making

As a successful entrepreneur, you are wired for decision-making. The constant loop of “What if we tried this?” fuels your creativity and drive. However, many traditional advisory engagements can lead to implementation failures:

1. Data Analysis: The advisor reviews your business metrics.
2. Recommendations: They develop a plan based on their findings.
3. Owner Response: You agree with the plan—but then take no action.

This isn’t about disagreement; it’s about ownership. You’re more likely to implement decisions you help create. This is why coaching before advisory work is essential, especially in exit planning.

Identity: The Key Variable in Exit Planning

Advisors often zoom in on valuation, tax efficiency, and succession logistics. While these aspects are important, the critical question you must consider is:

“What will you do when you no longer own this business?”

If your answer is vague—like “I’ll figure it out later” or “I’ll travel” —then your exit plan is likely incomplete. Liquidity without purpose can lead to regrets.

The Realities of Post-Exit Life

Research shows that 75% of former business owners report dissatisfaction a year after exiting. This is rarely due to financial shortcomings; it’s often because they haven’t redefined their identity.

As a business owner, you are exiting more than just an asset—you are relinquishing your relevance. Recognizing this early in your planning can lead to far better outcomes.

Conclusion: A Call to Action for Business Owners

Navigating the complexities of your business and its impact on your identity requires a unique approach from advisors. By understanding the emotional and psychological aspects of ownership, you can foster more meaningful relationships with your advisors.

If you’re contemplating exit strategies or want to redefine your post-business identity, consider engaging with a coach or advisor who recognizes these unique dynamics. Your business is your legacy; make sure your exit plan honors that.

John F. Dini develops transition and succession strategies that allow business owners to exit their companies on their own schedule, with the proceeds they seek and complete control over the process. He takes a coaching approach to client engagements, focusing on helping owners of companies with $1M to $250M in revenue achieve both their desired lifestyles and legacies.

Manufacturer Stuck in the “Neutral Zone”

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Here is how exit planning helped a business owner out of the Neutral Zone.

This manufacturer reached out to an exit planning consultant after receiving a book on planning as a gift from a local professional. He was in no particular hurry to leave his business. In the preceding twenty years of ownership, he had grown it from a local vendor to home builders into a nationally known specialty house.

The company provided him with a good living, generating roughly $700,000 a year in free cash flow for each of the previous five years. He wanted to continue for at least a few more years but also was concerned that he do the right things to maximize his price when the time came to move on.

What’s the Problem?

The consultant pointed out several issues that could dramatically impact his eventual transition.

First, he was handling too many duties that should be delegated. These weren’t things that required his special expertise, but rather areas where he was comfortable in just “taking care of it.” These included troubleshooting IT problems. Although the company had a full-service contract for those services with an outside vendor, he felt it was just “faster” if he first tried to fix the issue himself. Owner centricity is a major value killer in a sale.

On large orders, he prepared the price quotes personally. There were several employees in the sales department who did the majority of quotes, but after one had made an expensive error, the owner took any order over a certain dollar amount as his personal responsibility.

The consultant also pointed out that the business was in the “Neutral Zone” regarding profitability as the principal factor in valuation. With $700,000 in cash flow, it was too big for most entrepreneurial owner-operators to afford.

On the other hand, it was too small to attract a private equity or strategic buyer. Professional acquirers typically pay higher multiples but are seldom interested in acquisitions with less than $1,000,000 in cash flow.

Longer-Term Preparation

The owner retained the consultant as a coach to keep him on track as he addressed the issues. In the next few years, the company made a small acquisition resulting in a second location and greater production capacity. They hired a sales manager who could handle major quotes. At the exit planner’s recommendation, the owner implemented EOS with a different consultant for greater accountability in the management team.

A key employee who, like the owner, had also been a “jack of all trades” enjoyed an incentive program based solely on the company’s gross profit over a fixed level. The consultant pointed out that the improvements driving growth would very quicky make this employee wealthy without any increase in responsibilities. Fortunately, the employee resigned for personal reasons before this became an issue.

For the other employees, they installed new incentive programs based more on increasing profitability. Key employees also received stay bonuses and long-term synthetic equity incentives. This initially caused some concern, (“Are you selling the business?”) but that quickly died down when it became plain that no changes were imminent.

Breaking Out of the Neutral Zone

The next five years brought ups and downs. COVID first reduced sales, then created a surge that couldn’t be duplicated. Eventually the company settled into a sustainable growth pattern, reaching well over $1,000,000 in EBITDA. Of course, there were multiple inquiries about selling during this period. However, the owner felt none of them satisfied his goals for a rewarding life after the business.

His efforts to change the value of his business were driven by the clear personal objectives developed with the planner, rather than just a pursuit of growth for growth’s sake. Eventually he agreed to sell the business to a strategic acquirer for roughly twice the value of an appraisal that was done at the beginning of the process.

None of the changes made were earth-shaking. Having a goal, the means to track it and a framework for moving towards it translated into millions of additional dollars in the owner’s pocket. He was comfortable with a transaction that also preserved his legacy and his employees’ futures.

Is your client ready for a transition? Have them take our 15 minute assessment.

John F. Dini develops transition and succession strategies that allow business owners to exit their companies on their own schedule, with the proceeds they seek and complete control over the process. He takes a coaching approach to client engagements, focusing on helping owners of companies with $1M to $250M in revenue achieve both their desired lifestyles and legacies.

The Exit Planning Fallacy – A Business Owner’s Perspective

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One of the most common sales pitches you might hear from someone claiming to help you “enhance value” goes something like this:

“I’ve reviewed your company and believe it’s worth $4.2 million today. With the right planning, it could be worth $7.7 million. Would you rather exit with $4.2 million or $7.7 million?”

That’s not really a question—it’s a setup. Of course, no business owner would willingly choose the smaller number. But the real issue isn’t which number you prefer. It’s what it actually takes to bridge that gap—and whether you’re being given a full picture.

Are You Falling for the Planning Fallacy?


There’s a psychological term for this overly optimistic way of thinking: the planning fallacy.

A private equity investors group I follow, Chenmark.com, once cited a study published in the Journal of Personality and Social Psychology that perfectly illustrates the concept:

From a psychological perspective, the planning fallacy can perhaps be studied most profitably at the level of daily activities. Consider one familiar example: Academics who carry home a stuffed briefcase full of work on Fridays, fully intending to complete every task, are often aware that they have never gone beyond the first one or two jobs on any previous weekend.

The intriguing aspect of this phenomenon is the ability of people to hold two seemingly contradictory beliefs: Although aware that most of their previous predictions were overly optimistic, they believe that their current forecasts are realistic. It seems that people can know the past and still be doomed to repeat it.

What’s fascinating is that they know this pattern. Yet, every weekend, they’re sure this time will be different. Business owners do something similar: despite knowing how long things usually take (and how unpredictable growth can be), we still believe “this time” will follow our best-case forecast.

You may hear that big valuation potential and think, “Yes, that’s what I’ve always wanted—to grow the company by 83%! I just needed a plan.”

But a plan alone isn’t enough. It’s a start—but not the whole story.

What Really Closes the Gap?


Let’s reframe that optimistic pitch with a more realistic one:

“To grow from $4.2 million to $7.7 million in five years, you’ll need proper planning, dedicated effort, some strategic hires, and reinvesting a significant portion of your profits. That requires growing the business 19% annually—starting immediately. That’s more than double your best year to date. If you spend a year building that foundation first, then you’d need to grow at least 25% annually over the next four years. If you keep growing at your best year’s rate of 7.5%, it will take over 12 years to reach that goal.”

Those are the facts. And the reality is that very few business owners hit those growth rates without serious changes—and trusted advisors to help them.

The Power of Perspective (and the Right Guide)


You may have a solid company. It supports your lifestyle, your employees, and your reputation. Maybe you’ve even dreamed of taking it further. But the risks, the effort, or the lack of a clear roadmap have held you back.

That’s exactly where experienced advisors come in—not to promise easy gains, but to help you map a realistic path to your goals. They help align what you want (your proceeds), with what you’re willing to do (your effort), in the time you have left (your exit timeline).

In our work, we use a Value Gap coaching model that considers four essential pieces:

1. Current business value
2. Your desired outcome—not just “more,” but a specific number
3. The timeframe in which you want to exit
4. The required growth rate to get there

Often, once those last two are on the table, the conversation changes. It’s not just about the money—it’s about what you’re willing and able to do to get there.

The real planning fallacy? Believing it’s just about hitting a number. The truth is, getting the outcome you want depends on understanding the full picture—and working with an advisor who helps you navigate it honestly, strategically, and with clarity.

John F. Dini develops transition and succession strategies that allow business owners to exit their companies on their own schedule, with the proceeds they seek and complete control over the process. He takes a coaching approach to client engagements, focusing on helping owners of companies with $1M to $250M in revenue achieve both their desired lifestyles and legacies.

Are You Financially Ready to Exit Your Business Even if it Happened Tomorrow?

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Does Your Current Situation Have You Financially Ready to Exit Your Business?

Setting the Scene: The Importance of Financial Preparedness for Exiting a Business

Exiting a business is a significant decision that requires careful consideration, particularly regarding financial readiness. Whether you’re considering retirement, pursuing new ventures, or simply ready to move on, being financially prepared is crucial for a smooth transition.

Understanding the Decision: Factors to Consider Before Exiting Your Business

Before making the leap, it’s essential to understand the various factors that influence your decision to exit your business. From personal goals to market conditions, several considerations can impact your readiness to move on from your business venture.

Assessing Your Financial Readiness:
Evaluating Your Current Financial Situation: Income, Expenses, and Assets

Start by taking stock of your current financial situation. Evaluate your income streams, including revenue from the business, personal investments, and other sources. Consider your monthly expenses and assess your assets, including both business and personal holdings.

Estimating Your Business’s Value: Determining Its Market Worth

Determining the value of your business is a critical step in assessing your financial readiness to exit. Consider consulting with a business valuation expert to get an accurate estimate based on various factors, including revenue, assets, market trends, and industry standards.

Analyzing Cash Flow: Ensuring Stability Post-Exit

Cash flow analysis is essential to ensure financial stability post-exit. Evaluate your business’s cash flow projections to understand how it will sustain your lifestyle and cover expenses after you’ve left the business. Consider factors such as ongoing revenue streams, debt obligations, and potential changes in expenses.

Understanding Exit Options:
Exploring Different Exit Strategies: Sale, Succession, or Closure

There are several exit strategies to consider, including selling the business, passing it on to family members or employees through succession, or simply closing the doors. Each option has its pros and cons, depending on your personal and financial goals, as well as the state of your business.

Pros and Cons of Each Option: Weighing the Benefits and Challenges

Take the time to weigh the advantages and disadvantages of each exit strategy. Selling the business may offer a significant financial windfall but requires finding the right buyer. Succession can preserve your legacy but may come with complexities in transition. Closure provides a clean break but may not maximize financial returns.

Considering Timing: Is Now the Right Time to Exit?

Timing is crucial when it comes to exiting your business. Consider factors such as market conditions, industry trends, personal readiness, and potential tax implications. Assess whether the current timing aligns with your financial goals and objectives.

Financial Planning for Exit:
Creating a Financial Exit Plan: Setting Clear Goals and Objectives

Develop a comprehensive financial exit plan that outlines your goals and objectives for exiting the business. Define what financial success looks like for you and establish clear milestones and timelines for achieving your objectives.

Building a Contingency Fund: Preparing for Unexpected Expenses

Prepare for unexpected expenses by building a contingency fund. Set aside a portion of your assets to cover unforeseen costs or emergencies that may arise during the exit process. Having a financial safety net in place can provide peace of mind and ensure a smoother transition.

Engaging Financial Advisors: Seeking Professional Guidance for Exit Planning

Consider seeking guidance from financial advisors who specialize in exit planning. An experienced advisor can help you navigate complex financial decisions, optimize tax strategies, and maximize the value of your business. Their expertise can provide valuable insights and support throughout the exit process.

Maximizing Business Value:
Increasing Profitability: Strategies to Boost Revenue and Reduce Costs

Take proactive steps to increase the profitability of your business before exiting. Implement strategies to boost revenue, such as expanding market reach, launching new products or services, or improving customer retention. Similarly, focus on reducing costs and improving operational efficiency to enhance overall profitability.

Enhancing Business Operations: Improving Efficiency and Productivity

Streamline business operations to maximize efficiency and productivity. Identify areas for improvement, such as workflow processes, technology integration, and resource allocation. By optimizing operations, you can increase the value of your business and make it more attractive to potential buyers or successors.

Investing in Growth Opportunities: Expanding Market Reach and Customer Base

Explore growth opportunities to expand your business’s market reach and customer base. Consider diversifying into new markets, partnering with complementary businesses, or investing in marketing and advertising efforts. By positioning your business for growth, you can enhance its value and appeal to potential buyers or successors.

Managing Debt and Liabilities:
Assessing Debt Obligations: Understanding Your Business’s Debt Structure

Assess your business’s debt obligations to understand its financial liabilities. Review outstanding loans, lines of credit, and other forms of debt, including repayment terms and interest rates. Understanding your debt structure is essential for developing a plan to manage or repay debts before exiting the business.

Developing a Debt Repayment Plan: Prioritizing Payments and Negotiating Terms

Develop a debt repayment plan to address outstanding obligations before exiting the business. Prioritize debt payments based on interest rates, maturity dates, and creditor requirements. Explore options for negotiating repayment terms or consolidating debts to improve your financial position.

Addressing Legal and Financial Liabilities: Mitigating Risks Before Exit

Identify and address any legal or financial liabilities that may pose risks to your business or personal assets. Review contracts, leases, and agreements to ensure compliance and mitigate potential liabilities. Seek legal advice to address any outstanding legal issues or liabilities before finalizing your exit plans.

Preparing Personal Finances:
Separating Personal and Business Finances: Organizing Accounts and Assets

Separate your personal and business finances to streamline your financial affairs. Organize accounts, assets, and expenses into distinct categories to simplify financial management and reporting. Establish clear boundaries between personal and business transactions to avoid confusion and potential legal or tax issues.

Building Personal Savings: Establishing a Safety Net for Post-Exit Life

Build personal savings to establish a financial safety net for post-exit life. Set aside funds in savings accounts, retirement plans, or investment portfolios to cover living expenses, healthcare costs, and other financial needs. Having a robust savings cushion can provide financial security and peace of mind during the transition period.

Planning for Retirement: Securing Financial Stability Beyond Business Ownership

Plan for retirement to ensure long-term financial stability beyond business ownership. Evaluate retirement savings options, such as IRAs, 401(k)s, or pensions, and consider how they fit into your overall financial plan. Develop a retirement income strategy that aligns with your lifestyle goals and objectives for retirement.

Tax Implications of Exit:
Understanding Tax Consequences: Capital Gains, Income Tax, and Other Considerations

Understand the tax implications of exiting your business, including capital gains tax, income tax, and other relevant taxes. Consult with tax professionals to assess your tax liability and explore strategies to minimize taxes legally. Consider timing your exit to optimize tax outcomes and maximize financial returns.

Utilizing Tax Strategies: Maximizing Deductions and Credits Before Exit

Explore tax strategies to maximize deductions and credits before exiting your business. Take advantage of available tax incentives, such as deductions for business expenses, retirement contributions, or capital investments. Implementing tax-efficient strategies can help reduce your overall tax burden and preserve more of your wealth.

Consulting Tax Professionals: Navigating Complex Tax Laws and Regulations

Seek guidance from tax professionals who specialize in business exits and transitions. A qualified tax advisor can help you navigate complex tax laws and regulations, interpret tax implications, and develop tax-efficient exit strategies. Their expertise can ensure compliance with tax requirements and optimize your financial outcomes.

Exiting with Confidence:
Finalizing Your Exit Plan: Documenting Agreements and Contracts

Finalize your exit plan by documenting agreements and contracts that outline the terms and conditions of your departure. Work with legal advisors to draft legally binding documents, such as sale agreements, succession plans, or dissolution agreements. Ensure all parties involved understand their rights and responsibilities.

Communicating with Stakeholders: Keeping Employees, Customers, and Partners Informed

Communicate openly and transparently with stakeholders about your exit plans. Keep employees, customers, suppliers, and partners informed about the transition process and how it may impact them. Address any concerns or questions promptly and reassure stakeholders of your commitment to a smooth transition.

Celebrating Achievements: Reflecting on Your Business Journey Before Moving On

Take time to reflect on your achievements and milestones before moving on from your business. Celebrate your successes and the hard work that went into building and growing your enterprise. Express gratitude to employees, customers, and supporters who contributed to your journey. Celebrating achievements can provide closure and pave the way for new beginnings.

Conclusion:
Taking the Leap: Are You Financially Ready to Exit Your Business?

Exiting a business is a significant decision that requires careful consideration and financial preparedness. By evaluating your financial readiness, understanding exit options, and planning strategically, you can confidently take the leap into the next chapter of your entrepreneurial journey.

Moving Forward with Confidence: Embracing the Next Chapter of Your Entrepreneurial Journey

As you embark on the journey of exiting your business, remember to move forward with confidence and optimism. Embrace the opportunities that lie ahead and leverage your experience and expertise to pursue new ventures or enjoy well-deserved retirement. With careful planning and preparation, you can navigate the transition successfully and embark on a new entrepreneurial adventure with confidence.

Reposted with permission of the author, Tara L. Groody, Executive Assistant/Operations Specialist for Brett Andrews and Fortress Business Advisory.

Brett Andrews, CWS, CExP, CEPA, is the President of Fortress Business Advisory. He has worked with individuals and businesses managing their assets since 1998. His mission is to help clients reach their goals while managing risk in their total financial situation. To accomplish this, Brett has combined modern financial planning techniques with technical, quantitative, and behavioral analysis to achieve a truly unique and dynamic approach to total wealth management.

How to Separate Yourself From Your Business – Why It’s So Important

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happy woman working at computer When you run your own business, oftentimes one of the most confusing aspects of the job, especially if you are new to the experience, is understanding how to separate yourself from your business. And this issue can show up in so many ways, from achieving a work/life balance and managing your time to how you get paid and even how much taxes you owe.

With this in mind, here we will offer a big-picture overview of this issue, and in future articles, we’ll drill down to some of the finer details of keeping your business and personal assets separate. Although it might not seem overly complicated or important, separating yourself from your business is a serious issue for every business owner.

You & Your Business Are Separate Entities

The first thing to keep in mind is this: you are not your business, you are not your heart project, your are not your work in the world or even the services you offer. Your business, heart project, work, service, and/or product may feel like it’s one and the same as you, or even as if it’s your baby. But one day, just like the little ones you give birth to, you may want your business to grow up and go on to live on its own without you. Or you may not want that—it’s all a matter of preference, and your decision on this point may even evolve over time.

Either way, this is a good thing to start thinking about now. Do you want what you are creating to live beyond you? If so, you’ll need to start thinking about it as an evolutionary entity that can grow separate from you. And whether you want it to live on beyond you or not, you want it to exist separately from you, because as you’ll learn, there are major tax and asset protection benefits for you by doing this properly.

Owning A Business vs. Being An Employee

To add perspective, let’s contrast what it’s like to run your own business with what happens when you are working as an employee.

The Employee Experience:

As an employee, you get paid via a paycheck, with taxes taken out and a W-2 issued to you at the end of the year. In this case, you and your money-earning vehicle are essentially one and the same.

You earn money, and you pay taxes on that money in the form of income taxes and payroll taxes. As an employee, what comes to you every pay period via your paycheck is yours to put into your personal financial accounts, so you can pay your bills, save, or invest. In that context, you are getting taxed on every dollar you earn.

There are some ways that you can save money tax free as an employee, such as by directing some of your pay into a 401(k), an IRA, or even a Health Savings Account, provided your employer offers such benefits. But for the most part, you are paying payroll taxes and income taxes—which are two separate types of taxes—on every dollar you make.

The Business Owner Experience:

In contrast, when you are earning money through a business entity that is under your control, money comes into your business, goes into your business accounts, and is first used to pay business expenses, which are deductible expenses to your business. When you deduct business expenses from the income of your business, you do not pay income taxes on that income. In this way, you can think of business expenses as a government-subsidized expenditure.

Here’s what I mean: if you can purchase a computer through your business and use it for business, you are paying for that computer with pre-tax dollars, which could save you up to 40% (or more depending on your state) on the cost of the computer, versus if you were to purchase that same computer with after-tax dollars. But this only works if you treat your business like a business, and properly separate your personal and business accounts.

To keep your business and personal expenses separate, your business entity needs its own bank account, its own credit cards, and it needs to pay you. You then always pay your personal expenses out of your personal accounts, never your business accounts. Whatever your business pays you will be subject to income tax and possibly payroll tax as well, though there are ways to significantly reduce your payroll tax obligation by choosing the right way to structure your business entity. Be sure to talk with us regarding how to structure your business for maximum tax savings, if you have not already gotten great guidance on that front.

To the extent that your business earns more money than what’s required to cover your basic needs, you may want to consider investing to hire experienced support staff (especially a skilled bookkeeper and administrative support) to free up your time and allow you to focus on generating more revenue, better serving your clients or customers, and growing your operation. Or you may choose to invest that money in additional education or training for yourself, so you can increase the value (and price) of your services. If you have excess cash flow, you’ll also want to know how to structure your profits, so you pay the smallest amount in taxes legally possible.

Don’t Mix Personal & Business Finances

Whatever you do, do not simply have one bank account that you pay both your personal and business expenses from, or you are going to get seriously confused, and you could even end up losing money or getting into legal or tax trouble, depending on your company’s entity structure.

If you have already paid business expenses out of a personal account, or by using personal credit cards, keep careful track and document exactly how much you paid out from those accounts to your business. This payment will either be an investment in your business that you will want to track for the future, or it will be a personal loan to your business that you will want to eventually have paid back.

Talk with your CPA regarding how best to structure investments in or as loans to your business, and then we can help you properly document your decisions. Or if you need strategic support on this issue, contact us, and ask about a LIFT Business Breakthrough Session, and we’ll look at all of your legal, insurance, financial, and tax strategic decisions together.

When you work with us, as your Family Business Lawyer™, we offer a number of systems and processes that make keeping your personal and business finances separate a snap. Not only that, but we offer additional services that make separating yourself from your business as easy and convenient as possible. Reach out to us to learn more.

Get Clear On Your Actual Financial Needs & Goals

One of the best ways to effectively manage your business and personal finances is to first get clear on what you need your business to pay you at a base level, so you can pay all of your bills and other personal expenses as well as meet your personal time and money goals. To get clear on this, we use a process called Money Mapping. If you haven’t worked with us on this yet, now is the time to finally get a solid understanding of how much money you actually need to reach your goals, rather than guessing or worrying about how much you need to earn to stay afloat.

We’ve Got Your Back

When it comes to separating yourself from your business and managing all of the different aspects involved with this process, you can count on us to provide you with the trusted support and guidance. With our help, you’ll learn how to do this in a way that not only ensures you are doing it right, but that actually adds value to your company and generates increased revenue. Sit down with us, your Family Business Lawyer™ to learn about all of the different ways we can support you in this area. Schedule your visit today.

This article is a service of Todd Jarvis, Family Business Lawyer™. We offer a complete spectrum of legal services for businesses and can help you make the wisest choices on how to deal with your business throughout life and in the event of your death. We also offer a LIFT Start-Up Session™ or a LIFT Audit for an ongoing business, which includes a review of all the legal, financial, and tax systems you need for your business.