Published on May 30, 2025

The journey of life takes some strange turns and one of mine has been my multi decade relationship with my former father-in-law, Raph. For years after my divorce was finalized, he and I would travel across the country to watch my elder son play baseball. In those years, Raph and I shared a hotel room, ate meals together, and assiduously avoided discussing his daughter.

We did not suffer from a lack of topics though. The wisdom Raph shared with me through our baseball journeys holds profound lessons for entrepreneurs. These insights may have been framed in the context of baseball, but their application reaches far beyond the ballpark.

For the last ten years, we have traveled together to watch my son play baseball, from his high school days through his college career. These trips have not just been about baseball — they have become opportunities for conversation, reflection, and learning. Raph, with his quiet, thoughtful observations, often shared pieces of wisdom as we sat in the stands together or recapped games after those had ended.

These lessons, while offered in the context of baseball, have deeper applications for life and business. Specifically, three of Raph’s Rules have stayed with me even though my son’s collegiate baseball career has now ended. Each of those Rules is seemingly simple, but they also resonate far beyond the ballpark, to my day job as a strategic business consultant. Raph’s advice to “make sure the player has a cold drink,” “always have a good haircut,” and “ensure there is someone rooting for you in the stands,” when applied to the challenges of running a business, offers both practical and emotional support on the entrepreneurial journey.

Taking Care of Yourself: The Cold Drink

Raph’s first Rule, “make sure the player has a cold drink,” is, on the surface, about taking care of a baseball player’s physical needs. In business, it is a reminder that entrepreneurs must take care of themselves if they want to be at their best. Success requires not only hard work but also self-care.

Too often, entrepreneurs push themselves relentlessly, believing that more work will always equal more success. But just like a player needs rest and hydration, a business owner needs to step away and refresh from time to time. Scheduling regular breaks throughout the day or taking a vacation might seem like a luxury, but it is essential for maintaining long-term productivity. Without these moments of rest, burnout becomes inevitable.

Similarly, preparing for challenges is key. Just as a player needs to stay hydrated to maintain performance, entrepreneurs must be prepared with the resources they need to navigate difficulties. Whether it is an emergency fund, a backup plan, or a mental health routine, being proactive can make all the difference when unexpected challenges arise.

In my work with small business owners, I have seen many people sacrifice their well-being for the sake of their company, only to find themselves overwhelmed and exhausted. Raph’s Rules reminds us that taking care of yourself is essential to taking care of your business.

The Importance of a Good Haircut

Raph’s second Rule, to “always have a good haircut,” seems like a straightforward comment on appearance. However, it holds a deeper meaning about the importance of presentation in both personal and professional life.

In business, a “good haircut” means presenting yourself and your company in the best possible light. It is not just about looking neat — it is about attention to detail and ensuring that every aspect of your business reflects professionalism. Whether it is the way you respond to emails or the layout of your office, these small details form lasting impressions on clients and partners.

Consistency is key here. Just as a good haircut leaves a lasting first impression, your brand needs to be cohesive and well-maintained across all platforms, from your website to your customer service. Your business should always look sharp and well-prepared.

This advice also extends beyond appearance to the idea of ongoing development. A “good haircut” in business means staying current. Entrepreneurs must continually update their skills, stay on top of industry trends, and be ready to adapt. Just as you would not let your appearance become unkempt, you should not allow your business to grow stale or outdated.

In light of this, business owners should regularly review their operations, looking for areas where they can improve how they present their brand to the world. Keeping things fresh and professional is not just about image — it helps maintain confidence in the marketplace.

Someone in the Stands

Raph’s third Rule has perhaps the most weight. “Everyone needs someone specifically rooting for them in the stands,” he would often say, and I have come to understand how important this is, not only in sports but in business as well.

Being an entrepreneur can be a lonely road. The responsibility of making decisions, managing teams, and shouldering the financial burden can feel overwhelming at times. This is why having support is so critical. Just as a player performs better when they know someone is cheering for them, entrepreneurs need the encouragement and backing of others to thrive.

This can come in many forms. It may be a mentor who offers guidance, a coach who helps refine skills, or simply a close friend or family member who provides emotional encouragement. In business, it could also mean building a network of fellow entrepreneurs who understand the unique challenges of running a company. Having someone “in your corner” can make the difference between persevering through tough times and giving up under pressure.

Raph’s simple reminder highlights a profound truth: success in business is rarely achieved alone. The presence of a trusted support system is essential, offering both practical advice and emotional strength. It is a reminder that, no matter how independent we strive to be, we all need someone cheering us on from the sidelines.

Raph’s Rules of Entrepreneurship

First, entrepreneurs must take care of themselves. In the same way that a baseball player needs hydration to perform well, business owners need to prioritize their well-being. Taking breaks, managing energy levels, and preparing for challenges are not signs of weakness — they are essential for long-term success.

Second, the way a business presents itself matters. Raph’s advice was to always have a good haircut, a reminder to keep the business looking sharp, consistent, and professional. From branding to personal development, every detail contributes to the image your business projects.

Finally, no entrepreneur should face the challenges of business alone. Just as every player needs someone rooting for them in the stands, business owners need a support system. Whether it is a mentor, a coach, or a network of peers, having people in your corner provides the encouragement and strength to keep moving forward.

The wisdom Raph shared with me through our baseball journeys holds profound lessons for entrepreneurs. These insights may have been framed in the context of baseball, but their application reaches far beyond the ballpark.

Looking back on the years I have spent with Raph, I am reminded of how these simple yet profound pieces of wisdom have shaped my understanding of both life and business. The lessons from our time spent at the ballpark serve as a powerful reminder that entrepreneurship is not just about hard work and skill. It is also about self-care, presentation, and the support of others.

Raph’s Rules — shared over countless innings and road trips — offers a timeless framework for approaching the challenges of business with balance, professionalism, and an appreciation for the importance of support. As entrepreneurs, we can all benefit from taking a moment to ask ourselves: Have we had our cold drink today? Is our haircut looking sharp? And most importantly, who is rooting for us in our entrepreneurial journey?

In the game of business, just like in baseball, success is about more than just playing the game. It is about how you prepare, how you present yourself, and the people who stand by your side, cheering you on.

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