Navigating Business Exits and Wealth Management

Inspired by my recent conversation with Patrick Stroh on the M&A Masters Podcast

The $20 Million Question: Why Do Smart Business Owners Get Stuck in the Red Zone?

During my recent appearance on the M&A Masters Podcast, host Patrick Stroh and I explored something I've been wrestling with throughout my career: why do successful entrepreneurs—people who've built incredible businesses—often find themselves unprepared for the complexity of their exit?

The analogy that came to mind was football. You've masterfully driven your business down the field to the 20-yard line. But now, in the red zone, everything changes. The stakes are higher, the pressure is intense, and one wrong move can cost you dearly. This is where many business owners discover they need more than individual advisors—they need a coordinated team.

The Silo Problem: When Expert Advice Becomes Fragmented

Over the years, I've noticed the same pattern repeatedly: successful business owners work with highly qualified professionals—accountants, attorneys, financial advisors, insurance specialists—but these advisors operate in complete isolation from each other.

The result? Fragmented advice that often conflicts and creates dangerous gaps in planning, and misses opportunities to build wealth.

Here's what this looks like in practice:

• Your accountant recommends one tax strategy
• Your attorney flags legal issues with that same strategy
• Your financial advisor suggests investment approaches that don't align with either
• Your insurance agent operates without understanding your overall risk profile

I regularly ask business owners: "When was the last time all your key advisors sat around a table discussing you and your agenda—not their own individual expertise, but your unified path forward?"

The answer is almost always: "Never."

The Fractional Family Office Solution: Elite Planning Without the Elite Price Tag

Traditionally, coordinated wealth planning through family offices was reserved for the ultra-wealthy—those with hundreds of millions in assets. But what about successful business owners who have built substantial wealth but don't meet that threshold?

This gap led us to develop the fractional family office model. Instead of hiring a full-time team of specialists, you gain access to coordinated expertise when you need it, with someone who understands your complete picture.

The fractional family office approach provides:

• Unified Strategy: All advisors work from the same playbook
• Specialized Expertise: Access to best-in-class professionals without the overhead
• Coordinated Planning: Business strategy and personal wealth planning designed together
• Proactive Management: Identifying opportunities and risks before they become critical

The Sully Principle: Why Experience Matters When You've Never Done This Before

During our conversation, I shared the story of Captain Sully Sullenberger, who successfully landed a plane in the Hudson River. Here was arguably the best pilot to handle that crisis—military trained, decades of experience, at the peak of his career. Yet he had never landed a plane in the Hudson River before.

This perfectly illustrates the challenge facing exiting business owners. You may be the absolute best at running your company, but you've likely never sold a business before. The skills that made you successful in building your enterprise are different from those needed to exit successfully.

This is why the most successful exits I've witnessed share common characteristics:

• They start planning 2-3 years before the intended sale
• They work with advisors experienced in business transitions
• They address both business optimization and personal wealth planning together
• They coordinate all aspects of the exit strategy

The Forgotten Market: Why $5 million - $75 million Businesses Need Specialized Attention

The lower middle market represents a unique segment. Unlike ultra-high-net-worth individuals who have extensive resources and coordinated teams, and unlike smaller businesses that may have simpler planning needs, this segment faces complex challenges without proportional advisory support.

Characteristics of this market:

• Substantial wealth, but not enough to justify traditional family office costs
• Complex business structures requiring sophisticated planning
• Significant tax implications demanding advanced strategies
• Multi-generational wealth transfer considerations
• Risk management needs that extend beyond basic insurance

Taking Action: From Complexity to Clarity

The entrepreneurs who achieve successful exits don't necessarily have better businesses or more wealth—they simply refuse to navigate the complexity alone. They recognize that the same focus and strategic thinking that built their business must be applied to their exit.

Your next steps should include:

1. Assessment: Understand where you are today and where you want to go
2. Team Building: Assemble coordinated advisors, not siloed experts
3. Planning: Develop unified business and personal wealth strategies
4. Optimization: Implement improvements that maximize your exit value
5. Protection: Secure appropriate insurance and risk management tools

The Path Forward: Designing Your Exit, Not Defaulting Into It

As I emphasized to Patrick, the most successful business owners are proactive about their exit planning. They don't wait until they're ready to sell to start thinking about optimization, tax strategy, or wealth transfer.

The complexity of modern business exits—from regulatory requirements to tax implications to family dynamics—requires the same level of strategic thinking you've applied to building your business. The difference is that you can't do it alone, and you can't do it with advisors who don't communicate with each other.

The choice is yours: exit by design or exit by default. The outcomes are dramatically different.

Ready to start planning your optimal business exit?

Schedule a no-obligation, exploratory call with me. We'll delve into your business specifics and long-term goals, formulating strategies to build and protect your wealth as you prepare for your ideal business endgame.

Joseph LoPresti, leads ClearPoint Family Office and Arlington Wealth Management, and brings over 39 years of wealth management and business expertise to the table. Joseph is passionate about guiding fellow business owners  through a smooth and satisfying transition, and coordinating all aspects of their wealth toward a secure and prosperous life.

ClearPoint Family Office (CPFO) offers tax planning, consulting, and preparation, as well as estate and business consulting. CPFO does not offer investment advice. When appropriate, CPFO may refer clients to Arlington Wealth Management (AWM), an SEC registered investment adviser, for advisory services. Registration as an investment adviser does not imply a certain level of skill or training, and the content of this communication has not been approved or verified by the United States Securities and Exchange Commission or by any state securities authority. CPFO and AWM are affiliated entities under common ownership.