Building for Succession Part II: Four keys to a successful alignment of personal and business goals

Over the past thirteen years, I’ve reviewed thousands of pitch decks and met with nearly six hundred entrepreneurs. Only a few dozen truly stood out, and less than ten I'll never forget. One memorable pitch happened nearly a decade ago. When asked, "Where do you see yourself and the company in ten years?" the founder confidently replied, "I see myself taking this company public. It’s my dream to be the CEO of a publicly traded company."

Fast-forward eight years—after navigating the ups and downs of business, including the COVID-19 crisis—he was stepping down as CEO, bringing in someone to realize the goals he had set. He remembered his earlier statement but explained how the journey taught him about his strengths, passions, and personal life. While his vision for himself had adapted, his vision for the company remained unchanged, so he planned and executed to bring in new leadership to help realize it. However, without a plan that aligned with his personal and business goals, the transition required more effort than expected. This story ties into a broader truth about entrepreneurship. Mark Cuban, one of the most accomplished entrepreneurs of all time, has twelve rules for starting a business. His first rule is, "Don't start it unless it's an obsession and something you love." His second rule? "If you have an exit strategy, it's not an obsession!" These sage nuggets of advice are key things we identify before investing or supporting a company. That said, while you should be entirely obsessed with the business you’re building, you can—and should—still have a personal strategy for how growing the company and its prospective outcomes will impact you personally. Not doing so can severely limit your potential to realize the ultimate vision and obsession for the business. Continuing my first article on “Building for Succession”, here is a more in-depth examination for achieving its first element: Aligning personal and business goals early can ensure both thrive.

1. Financial Preparedness

When most entrepreneurs start a business, the focus is often on Product Market Fit, addressing target markets, and building a Minimum Viable Product (MVP) that will meet investor metrics. While these are crucial to business growth, an honest assessment of how personal goals align with the business's trajectory is often missing. Succession planning isn't just about preparing the business for new leadership; it's about ensuring that your business supports your ambitions from the outset. One often overlooked area is financial preparedness—not just for the business but also for the entrepreneurs themselves. Building and running a business often leads to income gaps, personal sacrifices, and the need to invest significantly in the company. It's essential to ask early: How financially prepared am I for this journey? Do you have the emotional resilience to handle periods of financial uncertainty or reinvestment? The ability to sustain personal financial goals while growing the business requires thoughtful planning and understanding of the trade-offs involved.

Entrepreneurs need to align both technically and emotionally with the financial realities of their business. By setting realistic personal financial goals early on—whether it's saving for retirement, maintaining a certain lifestyle, or planning for future liquidity—you can manage the balance between personal financial security and business growth. This alignment ensures you're not left scrambling when the business requires more resources.

2. Shape Your Business Strategy with Personal Vision and Obsession

While financial alignment is critical, it’s equally important to shape your business strategy around the personal vision that drives you—and the obsession that made you start the business in the first place. Mark Cuban’s rule of starting only if it's an obsession holds weight here. If you're obsessed with solving a specific problem and passionate about your product or service, that energy fuels your business strategy. This obsession can shape the culture, direction, and focus of the company in ways that differentiate it from competitors.

When your personal goals, values, and obsession with the problem the business is solving are integrated into your business strategy, they guide decisions—whether it’s product development, customer experience, or scaling. If the founder’s passion lies in innovating or making a lasting impact, the strategy can revolve around that, allowing the business to thrive aligning with the founder’s values. As the business grows, this alignment provides both motivation and clarity, ensuring that every step taken reinforces the founder’s original vision.

By anchoring your strategy in the obsession that got you started and aligning it with personal goals, you can build a business that not only thrives but continues to excite and fulfill you personally.

3. The Importance of Personal-Professional Balance

Obsession can be an incredible driving force, but like a powerful drug, it has its dangers. Without balance, obsession can consume you, separating you from other loves, needs, and priorities in your personal life. Many founders, driven by their passion, allow the business to eclipse everything else, leaving little room for personal fulfillment outside of work. This tunnel vision can lead to burnout, strained relationships, and an imbalanced life.

To avoid this, entrepreneurs must consciously balance their professional ambitions with their personal lives. Yes, be obsessed with solving the problem that drives your business—but don’t let that obsession erode your ability to experience joy, connection, or growth outside of work. Founders should regularly check in with themselves: Am I neglecting essential aspects of my life? Am I still aligned with my values and goals, or has my obsession taken over?

By aligning personal and business goals early, founders can create healthier relationships between work and life. This balance not only prevents burnout but also sustains long-term happiness and energy. Your obsession should fuel your success, not diminish other aspects of your life.

4. Flexibility in Adapting to Change

Having a personal succession strategy doesn’t mean you’re focusing on the exit. Instead, it’s about ensuring that you, the founder/owner, aren’t completely tethered to your business—the success of the company and any potential exit need to be separate from your identity. By having a plan in place early, you create a buffer that allows for adjustments.

When life changes or the business needs to evolve, you can tweak your plan rather than scramble to develop one from scratch. This proactive approach helps avoid emotional stress when a transition becomes necessary. It also keeps any personal stakeholders—like spouses or partners—engaged and supportive, knowing there’s a clear plan to manage personal and professional shifts. This alignment fosters stability and reduces friction when inevitable changes occur. By separating your identity from the company’s eventual outcome, you create flexibility that allows you to adapt without feeling like you’ve lost yourself. Succession becomes a natural evolution rather than a rushed, reactive decision.

In conclusion

Aligning personal and business goals early on creates a foundation for sustainable growth and personal fulfillment. Entrepreneurs can weather the inevitable income gaps and reinvestment periods without personal financial stress by ensuring financial preparedness from the start. Additionally, shaping your business strategy around your obsession with solving a problem ensures long-term motivation. Still, it must be balanced with personal well-being to avoid burnout and strained relationships. Having a personal succession strategy isn’t about focusing on the exit; it’s about maintaining flexibility, separating your identity from the company, and keeping personal stakeholders engaged. When these elements are aligned, succession becomes a natural evolution, and you and the business are set up for long-term success and fulfillment.