John S Schwalbach
John S. Schwalbach, CFP®, CLU, AIF®, CEPA
April 10, 2025

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The Entrepreneurial Journey: From Card Tables to Financial Freedom

Think back to when you first started your business. For us at Freedom Financial Partners, it was 12 years ago last month, beginning with a couple of computers, a few card tables, and endless optimism. We understand firsthand that as a business owner, your company is always on your mind—continuously anticipating potential challenges and striving to address issues before they arise.

The initial phase of entrepreneurship is primarily focused on survival—keeping the lights on and, if things go well, eventually upgrading from a card table to a real desk. During this period, long-term planning often takes a backseat to the weekly grind of maintaining stable cash flow and ensuring your business continues to exist. The statistics tell the sobering story: 20% of businesses fail in their first year, 50% within five years, and 65% within a decade. Building a sustainable enterprise in the face of these odds requires a certain kind of resilience—perhaps even a touch of madness.

The Missing Piece: Personal Financial Planning for Successful Business Owners

What we frequently observe when speaking with business owners who have overcome the sustainability challenge is a significant disconnect. While many have evolved to incorporate longer-term business forecasting into their operations, they often haven’t applied the same disciplined approach to their personal financial situations.

This imbalance is completely understandable. Even after 10-15 years, a sustainable business typically demands total commitment from leadership and ownership teams. This intense focus leaves little time to contemplate long-term personal financial projections or consider what happens when the business journey eventually concludes.

We’ve also noticed that many financial planners in our industry fail to recognize that business owners simply don’t have hours to spend contemplating these matters. As a business owner, you need financial planners who understand your unique challenges and time constraints. Just as you rely on trusted individuals to delegate business responsibilities, you need the same in your financial life—someone you can depend on to keep you organized and efficiently present appropriate topics for decision-making.

The EOS Connection: A System That Transformed Our Business and Our Approach

Our firm experienced remarkable growth when we implemented the Entrepreneurial Operating System (EOS) four years ago. This framework helped us become more intentional with our time and business operations, allowing us to take our company to new heights. We’ve been so impressed with the system that we’ve incorporated EOS principles into our business owner services.
We’ve discovered that many EOS principles directly translate to effective financial planning for business owners. Here’s how the parallels work:

1. Commitment to the Process

The first step in both EOS and effective financial planning is making a genuine commitment to the process. For busy business owners, this financial planning commitment often competes with countless other priorities. We’ve seen success when business owners designate personal financial planning as a quarterly “rock” in their business planning.

While our business owner services are specifically designed to minimize the time required for financial organization, the process still demands some time and dedication. Similar to implementing EOS, there will likely be blind spots and areas that don’t initially align with your expectations. This is a natural part of the journey toward financial clarity.

2. Establishing Your Financial Team

This is typically when business owners first approach us. They’re seeking a financial “integrator” to help implement their vision. Our role isn’t to impose our values on the financial planning process—it’s to help clarify your values and assist with implementation. We keep you on track toward your goals while saving you time and effort by serving as your financial partner.

Just as EOS emphasizes the importance of the right leadership team, your financial planning requires the right professionals who understand your business context and personal aspirations.

3. Clarifying Your Financial Vision

In EOS, companies work through the Vision/Traction Organizer (V/TO) to document core values, 10-year targets, and other essential elements. Our financial planning process begins similarly with our proprietary “Empowering Conversations” exercise, where we clarify goals and values with the entire household, including spouses when applicable.

We create a supportive environment where clients feel comfortable being vulnerable, which helps illuminate long-term vision and desired outcomes. We’ve encountered virtually every type of financial goal imaginable—and one of the most rewarding aspects of our work is uncovering unspoken goals and dreams, then demonstrating how they can become reality.

4. Implementing a Systematic Approach

As with EOS, an effective financial system can’t simply be established and then left unattended. Part of what makes EOS so powerful is its ongoing operating cadence—and we’ve adopted similar principles in our planning process.

Typically, we compile annual data into a comprehensive financial dashboard that guides decision-making and course corrections. We also discuss our version of quarterly and yearly “rocks” and provide accountability. Throughout this process, we continually evaluate long-term goals to ensure we’re tracking toward them appropriately.
A Financial System Built for Busy Business Owners

We didn’t intentionally set out to mirror EOS principles, but effective systems often share common elements. Our approach assembles the right team, establishes long-term goals aligned with your values and 10-year vision, and creates yearly and quarterly objectives that contribute to those broader goals.

Crucially, we’ve designed our entire system with the understanding that business owners are extraordinarily busy and don’t have time for inefficient processes. Our streamlined approach respects your limited time while still delivering comprehensive financial guidance.

Beyond the Balance Sheet: Understanding the Business Owner Mindset

What truly sets our approach apart is our deep understanding of the business owner mindset. We recognize that your business isn’t just a source of income—it’s an extension of your identity, a vehicle for creating impact, and often your largest asset.

This understanding influences every aspect of our planning process:

Business Value Integration

We help you determine how your business value integrates with your personal financial plan. What’s the exit strategy? How does business growth contribute to personal wealth? What’s the optimal ownership structure to support your goals?

Cash Flow Synchronization

Business owners often experience irregular income patterns. We develop strategies to synchronize business and personal cash flows, ensuring financial stability regardless of business cycles.

Tax-Efficient Strategies

The intersection of business and personal finances creates unique tax planning opportunities. We coordinate with your tax professionals to implement strategies that reduce your overall tax burden across both domains.

Risk Management

Business owners face distinct risks. We identify these vulnerabilities and implement protective measures that safeguard both your business and personal assets.

Legacy Planning

For many business owners, legacy extends beyond financial assets to include business continuity and values transmission. We help articulate and implement your vision for both family and business legacy.

Taking the Next Step

We’d love to introduce you to our process. Even if you aren’t ready to take immediate action, we enjoy connecting with fellow business owners to discuss the current business environment and explore how we might help in the future.

The day will come when you’re ready to add that quarterly “rock” to your plan and get your personal finances in order. When that happens, Freedom Financial Partners will be here, ready to help you apply the same disciplined approach to your personal finances that you’ve used to build your successful business.

John Schwalbach is Co-President of Freedom Financial Partners, specializing in financial planning and investment management for business owners. With extensive experience working with EOS-driven companies, John helps clients integrate business success with personal financial freedom.